Статті в журналах: "Dicaffeoylquinic acid"

1

Prakash, N. S., Devendra Reddy, R. Sundaram, U. V. Babu, L. Sharath, I. Bindu, and Chennu Surendra. "Identification and quantification of cinnamic acid derivatives in Cichorium intybus seed and its extract by High- Performance Liquid Chromatography with Diode-Array Detector (HPLC-DAD) and Electrospray Ionization Mass Spectrophotometry (LC-MS/MS)." Universities' Journal of Phytochemistry and Ayurvedic Heights I, no. 34 (June 24, 2023): 1–16. http://dx.doi.org/10.51129/ujpah-2022-34-1(1).

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A sensitive method coupling high-performance liquid chromatography (HPLC) with diode –array detector (DAD) and electrospray ionization mass spectrometry (MS) was optimized for separation, identification, and quantification of cinnamic acid derivatives in Cichorium intybus seed and its extract. Cinnamic acid derivatives such as chlorogenic acid, caffeic acid and Chicoric acid were quantified using respective standards. Apart from 4-o-Caffeoylqunic acid, other cinnamic acid derivative such as 3-o-caffeoylquinic acid was also identified and quantified by UV and MS/MS spectra and calculated as total caffeoylquinic acids using 4-o-caffeoylqunic acid as standard in the seed and its extract. Other cinnamic acid derivatives such as 1,3-dicaffeoylqunic acid, 1,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, dicaffeoylquinic acid-1 and dicaffeoylquinic acid-2 (two unknown) were identified and quantified by UV and MS spectra and calculated as total dicaffeoylquinic acids using chlorogenic acid standard in the seed and its extract. The total cinnamic acids were quantified by calculating the sum of chlorogenic acid, caffeic acid, chicoric acid, total caffeoylquinic acids(4-o-caffeoylquinic acid and 3-o-caffeoylqunic acid) and total dicaffeoyl-quinic acids(1,3-dicaffeoylqunic acid, 1,4-dicaffeoylquinic acid, 3,5-dicaffeoyl-quinic acid, 3, 4-dicaffeoylquinic acid, dicaffeoylquinic acid-1 and dicaffeoyl-quinic acid-2). The Phytochemical screening of C. intybus seed and its extract revealed that this plant is a rich source of cinnamic acid derivatives so, these markers (cinnamic acid derivatives) can used for routine quality control of Cichorium intybus seed and its extract.

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Kamarauskaite, Justina, Rasa Baniene, Lina Raudone, Gabriele Vilkickyte, Rimanta Vainoriene, Vida Motiekaityte, and Sonata Trumbeckaite. "Antioxidant and Mitochondria-Targeted Activity of Caffeoylquinic-Acid-Rich Fractions of Wormwood (Artemisia absinthium L.) and Silver Wormwood (Artemisia ludoviciana Nutt.)." Antioxidants 10, no. 9 (September 1, 2021): 1405. http://dx.doi.org/10.3390/antiox10091405.

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Caffeoylquinic acids are some of the chemophenetically significant specialized metabolites found in plants of the family Asteraceae Dumort., possessing a broad spectrum of biological activities. As they might be potential mitochondria-targeted antioxidants, effective preparation methods—including extraction, isolation, and purification of caffeoylquinic acids from plant sources—are in great demand. The aim of this study was to fractionate the caffeoylquinic acids from cultivated wormwood (Artemisia absinthium L.) and silver wormwood (Artemisia ludoviciana Nutt.) herb acetone extracts and evaluate their phytochemical profiles, antioxidant activity (radical scavenging and reducing activities), effects on kidney mitochondrial functions, and cytochrome-c-reducing properties. The main findings of our study are as follows: (1) Aqueous fractions purified from wormwood and silver wormwood herb acetone extracts are rich in monocaffeoylquinic acids (chlorogenic acid, neochlorogenic acid, 4-O-caffeoylquinic acid), while methanolic fractions purified from wormwood and silver wormwood herb acetone extracts are rich in dicaffeoylquinic acids (4,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid). Aqueous fractions purified from wormwood and silver wormwood herb acetone extracts were solely composed of monocaffeoylquinic acids. Methanolic fractions purified from wormwood and silver wormwood herb acetone extracts contained only dicaffeoylquinic acids. (2) Fractions purified from silver wormwood herb acetone extracts stood out as having the greatest content of caffeoylquinic acids. (3) The greatest radical scavenging activity was determined in the dicaffeoylquinic-acid-rich fraction purified from silver wormwood herb acetone extract; the greatest reducing activity was determined in the dicaffeoylquinic-acid-rich fraction purified from wormwood herb acetone extract. (4) The effect of both fractions on mitochondrial functions was dose-dependent; lower concentrations of caffeoylquinic-acid-rich fractions had no effect on mitochondrial functions, whereas higher concentrations of caffeoylquinic-acid-rich fractions reduced the state 3 respiration rate (with the complex-I-dependent substrate glutamate/malate). (5) Both monocaffeoylquinic- and dicaffeoylquinic-acid-rich fractions possessed cytochrome-c-reducing properties; the greatest cytochrome c reduction properties were determined in the dicaffeoylquinic-acid-rich fraction purified from wormwood herb acetone extract. In summary, these findings show that caffeoylquinic acids might be beneficial as promising antioxidant and cytochrome-c-reducing agents for the modulation of mitochondria and treatment of various mitochondrial-pathway-associated pathologies.

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3

Wang, Li, and Douglas H. Sweet. "Interaction of Natural Dietary and Herbal Anionic Compounds and Flavonoids with Human Organic Anion Transporters 1 (SLC22A6), 3 (SLC22A8), and 4 (SLC22A11)." Evidence-Based Complementary and Alternative Medicine 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/612527.

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Active components of complementary/alternative medicines and natural supplements are often anionic compounds and flavonoids. As such, organic anion transporters (OATs) may play a key role in their pharmacokinetic and pharmacological profiles, and represent sites for adverse drug-drug interactions. Therefore, we assessed the inhibitory effects of nine natural products, including flavonoids (catechin and epicatechin), chlorogenic acids (1,3- and 1,5-dicaffeoylquinic acid), phenolic acids (ginkgolic acids (13 : 0), (15 : 1), and (17 : 1)), and the organic acids ursolic acid and 18β-glycyrrhetinic acid, on the transport activity of the human OATs, hOAT1 (SLC22A6), hOAT3 (SLC22A8), and hOAT4 (SLC22A11). Four compounds, 1,3- and 1,5-dicaffeoylquinic acid, ginkgolic acid (17 : 1), and 18β-glycyrrhetinic acid, significantly inhibited hOAT1-mediated transport (50 μM inhibitor versus 1 μM substrate). Five compounds, 1,3- and 1,5-dicaffeoylquinic acid, ginkgolic acids (15 : 1) and (17 : 1), and epicatechin, significantly inhibited hOAT3 transport under similar conditions. Only catechin inhibited hOAT4. Dose-dependency studies were conducted for 1,3-dicaffeoylquinic acid and 18β-glycyrrhetinic acid on hOAT1, and IC50values were estimated as 1.2 ± 0.4 μM and 2.7 ± 0.2 μM, respectively. These data suggest that 1,3-dicaffeoylquinic acid and 18β-glycyrrhetinic acid may cause significant hOAT1-mediated DDIsin vivo; potential should be considered for safety issues during use and in future drug development.

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4

Konczak, Izabela, Shigenori Okuno, Makoto Yoshimoto, and Osamu Yamakawa. "Caffeoylquinic Acids Generated In Vitro in a High-Anthocyanin-Accumulating Sweet potato Cell Line." Journal of Biomedicine and Biotechnology 2004, no. 5 (2004): 287–92. http://dx.doi.org/10.1155/s1110724304404069.

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Accumulation of phenolic compounds has been monitored in a suspension culture of anthocyanin-accumulating sweet potato cell line grown under the conditions of modified Murashige and Skoog high-anthocyanin production medium (APM) over a period of 24 days. Tissue samples extracted with 15% acetic acid were analysed using HPLC at a detection wavelength of 326 nm. Among others, the following derivatives of caffeoylquinic acids were detected: 4,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, and 3,4,5-tricaffeoylquinic acid. Their total amount reached a maximum of 110 mg/gFW between the 4th and the 15th day of culture growth on APM. The major compound of the phenolic mixture was 3,5-dicaffeoylquinic acid with maximum accumulation level of 80 mg/100 gFW. The potential effects of targeted phenolic compounds on the nutraceutical qualities ofin vitroproduced anthocyanin-rich extracts are discussed.

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5

Chen, Fujia, Xiaohua Long, Zhaopu Liu, Hongbo Shao, and Ling Liu. "Analysis of Phenolic Acids of Jerusalem Artichoke (Helianthus tuberosusL.) Responding to Salt-Stress by Liquid Chromatography/Tandem Mass Spectrometry." Scientific World Journal 2014 (2014): 1–8. http://dx.doi.org/10.1155/2014/568043.

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Plant phenolics can have applications in pharmaceutical and other industries. To identify and quantify the phenolic compounds inHelianthus tuberosusleaves, qualitative analysis was performed by a reversed phase high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) and quantitative analysis by HPLC. Ten chlorogenic acids (CGAs) were identified (3-o-caffeoylquinic acid, two isomers of caffeoylquinic acid, caffeic acid,p-coumaroyl-quinic acid, feruloylquinic acid, 3,4-dicaffeoyquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid) by comparing their retention times, UV-Vis absorption spectra, and MS/MS spectra with standards. In addition, four other phenolic compounds, including caffeoyl glucopyranose, isorhamnetin glucoside, kaempferol glucuronide, and kaempferol-3-o-glucoside, were tentatively identified inHelianthus tuberosusleaves for the first time. The 3-o-caffeoylquinic acid (7.752 mg/g DW), 4,5-dicaffeoylquinic acid (5.633 mg/g DW), and 3,5-dicaffeoylquinic acid (4.900 mg/g DW) were the major phenolic compounds in leaves ofHelianthus tuberosuscultivar NanYu in maturity. The variations in phenolic concentrations and proportions inHelianthus tuberosusleaves were influenced by genotype and plant growth stage. Cultivar NanYu had the highest concentration of phenolic compounds, in particular 3-o-caffeoylquinic acid and 4,5-dicaffeoylquinic acid compared with the other genotypes (wild accession and QingYu). Considering various growth stages, the concentration of total phenolics in cultivar NanYu was higher at flowering stage (5.270 mg/g DW) than at budding and tuber swelling stages. Cultivar NanYu ofHelianthus tuberosusis a potential source of natural phenolics that may play an important role in the development of pharmaceuticals.

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6

Tian, Fang, Qun-Jia Ruan, Ying Zhang, Hui Cao, Zhi-Guo Ma, Gai-Lian Zhou, and Meng-Hua Wu. "Quantitative Analysis of Six Phenolic Acids in Artemisia capillaris (Yinchen) by HPLC-DAD and Their Transformation Pathways in Decoction Preparation Process." Journal of Analytical Methods in Chemistry 2020 (April 23, 2020): 1–8. http://dx.doi.org/10.1155/2020/8950324.

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We aimed to establish a quantitative analysis method of six constituents (5-caffeoylquinic acid, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 1,3-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid) in Artemisia capillaris (Yinchen) and its decoction by using HPLC coupled with DAD. Besides, the transformation paths of the six constituents were analyzed in decoction preparation processing. The analytical method was fully validated in terms of linearity, sensitivity, precision, repeatability, and recovery and applied to assess the transformation trend and quantitative analysis of the six constituents in Yinchen decoction. The contents of six constituents varied greatly in Yinchen herb and Yinchen decoction, and there were inextricable internal relationships between them. Presumably 3-caffeoylquinic acid was isomerized to generate 5-caffeoylquinic acid and 4-caffeoylquinic acid. Similarly, 1,3-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid were produced by isomerization of 4,5-dicaffeoylquinic acid. In conclusion, this study provides a chemical basis for quality control of Yinchen decoction, and the changes of selected markers in decoction could give us some novel perspectives to study the relationship between substances and drug efficacy.

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7

Padda, Malkeet S., and David H. Picha. "(184) Phenolic Composition and Antioxidant Activity of Sweetpotato Cultivars Marketed in the European Union." HortScience 41, no. 4 (July 2006): 1017D—1018. http://dx.doi.org/10.21273/hortsci.41.4.1017d.

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Phenolic compounds and antioxidant activity were quantified in the principal sweetpotato cultivars marketed in the European Union. Total phenolic content, individual phenolic acids, and antioxidant activity in each cultivar were determined using Folin-Denis reagent, reversed-phase HPLC, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) methods, respectively. Significant differences in phenolic composition and antioxidant activity were found between cultivars. A Jamaican-grown, white-fleshed cultivar had the highest total phenolic content [4.11 mg·g-1 chlorogenic acid (dry tissue weight)], while the highest antioxidant activity [3.60 mg·g-1 Trolox (dry tissue weight)] was observed in the orange-fleshed California-grown cultivar Diane. Chlorogenic acid and 3,5-dicaffeoylquinic acid were the predominant phenolic acids, while caffeic acid was the least abundant in most cultivars. The highest content of chlorogenic acid (0.42 mg·g-1 dry tissue weight); 3,5-dicaffeoylquinic acid (0.43 mg·g-1 dry tissue weight); and 3,4-dicaffeoylquinic acid (0.25 mg·g-1 dry tissue weight) was present in the white-fleshed Jamaican cultivar. The orange-fleshed cultivars Diane and Beauregard had the highest content of caffeic acid (0.13 mg·g-1 dry tissue weight) and 4,5-dicaffeoylquinic acid (0.32 mg·g-1 dry tissue weight), respectively.

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Nemzer, Boris, Diganta Kalita, and Nebiyu Abshiru. "Quantification of Major Bioactive Constituents, Antioxidant Activity, and Enzyme Inhibitory Effects of Whole Coffee Cherries (Coffea arabica) and Their Extracts." Molecules 26, no. 14 (July 16, 2021): 4306. http://dx.doi.org/10.3390/molecules26144306.

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Coffee cherry is a rich source of chlorogenic acids (CGAs) and caffeine. In this study we examined the potential antioxidant activity and enzyme inhibitory effects of whole coffee cherries (WCC) and their two extracts on α-amylase, α-glucosidase and acetylcholinesterase (AChE) activities, which are targets for the control of diabetes and Alzheimer’s diseases. Whole coffee cherry extract 40% (WCCE1) is rich in chlorogenic acid compounds, consisting of a minimum of 40% major isomers, namely 3-caffeoylquinic acids, 4-caffeoylquinic acids, 5-caffeoylquinic acids, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, 4-feruloylquinc acid, and 5-feruloylquinc acid. Whole coffee cherry extract 70% (WCCE2) is rich in caffeine, with a minimum of 70%. WCCE1 inhibited the activities of digestive enzymes α-amylase and α-glucosidase, and WCCE2 inhibited acetylcholinesterase activities with their IC50 values of 1.74, 2.42, and 0.09 mg/mL, respectively. Multiple antioxidant assays—including DPPH, ABTS, FRAP, ORAC, HORAC, NORAC, and SORAC—demonstrated that WCCE1 has strong antioxidant activity.

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9

El-Askary, Hesham, Heba H. Salem, and Amira Abdel Motaal. "Potential Mechanisms Involved in the Protective Effect of Dicaffeoylquinic Acids from Artemisia annua L. Leaves against Diabetes and Its Complications." Molecules 27, no. 3 (January 27, 2022): 857. http://dx.doi.org/10.3390/molecules27030857.

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Diabetes mellitus is a chronic disease affecting the globe and its incidence is increasing pandemically. The use of plant-derived natural products for diabetes management is of great interest. Polar fraction of Artemisia annua L. leaves has shown antidiabetic activity in vivo. In the present study, three major compounds were isolated from this polar fraction; namely, 3,5-dicaffeoylquinic acid (1); 4,5-dicaffeoylquinic acid (2), and 3,4- dicaffeoylquinic acid methyl ester (3), using VLC-RP-18 and HPLC techniques. The potential protective effects of these compounds against diabetes and its complications were investigated by employing various in vitro enzyme inhibition assays. Furthermore, their antioxidant and wound healing effectiveness were evaluated. Results declared that these dicaffeoylquinic acids greatly inhibited DPPIV enzyme while moderately inhibited α-glucosidase enzyme, where compounds 1 and 3 displayed the most prominent effects. In addition, compound 3 showed pronounced inhibition of α-amylase enzyme. Moreover, these compounds markedly inhibited aldose reductase enzyme and exerted powerful antioxidant effects, among which compound 3 exhibited the highest activity implying a notable potentiality in impeding diabetes complications. Interestingly, compounds 2 and 3 moderately accelerated scratch wound healing. Our findings suggest that these dicaffeoylquinic acids can be promising therapeutic agents for managing diabetes and its complications.

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Hordiei, Karyna, Tetiana Gontova, Sonata Trumbeckaite, Maksym Yaremenko, and Lina Raudone. "Phenolic Composition and Antioxidant Activity of Tanacetum parthenium Cultivated in Different Regions of Ukraine: Insights into the Flavonoids and Hydroxycinnamic Acids Profile." Plants 12, no. 16 (August 14, 2023): 2940. http://dx.doi.org/10.3390/plants12162940.

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Tanacetum parthenium, also known as feverfew, is rich in bioactive compounds, namely sesquiterpene lactones, flavonoids, and volatile oils. Sesquiterpene lactones possess anti-migraine activity, while phenolic compounds possess anti-inflammatory and antioxidant action. Phytochemical composition determines the pharmacological activity and so profiling is essential in quality assessment. The study aimed to evaluate cultivated feverfew plants’ phenolic profiles and antioxidant activity. Eleven phenolic compounds were identified in the samples of feverfew in Ukraine. Hydroxycinnamic acids predominate in the quantitative content of all the samples, namely chlorogenic acid, 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid. The total content of flavonoids ranged from 0.8 to 2.6%; the content of hydroxycinnamic acids varied from 3.3 to 6.5%. The obtained data testify to the prospects of using Ukrainian feverfew as a raw material with a significant content of phenolic substances to develop new herbal medicines.

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Tabassum, Nadia, Ji-Hyung Lee, Soon-Ho Yim, Galzad Javzan Batkhuu, Da-Woon Jung, and Darren R. Williams. "Isolation of 4,5-O-Dicaffeoylquinic Acid as a Pigmentation Inhibitor Occurring inArtemisia capillarisThunberg and Its ValidationIn Vivo." Evidence-Based Complementary and Alternative Medicine 2016 (2016): 1–11. http://dx.doi.org/10.1155/2016/7823541.

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There is a continual need to develop novel and effective melanogenesis inhibitors for the prevention of hyperpigmentation disorders. The plantArtemisia capillarisThunberg (Oriental Wormwood) was screened for antipigmentation activity using murine cultured cells (B16-F10 malignant melanocytes). Activity-based fractionation using HPLC and NMR analyses identified the compound 4,5-O-dicaffeoylquinic acid as an active component in this plant. 4,5-O-Dicaffeoylquinic acid significantly reduced melanin synthesis and tyrosinase activity in a dose-dependent manner in the melanocytes. In addition, 4,5-O-dicaffeoylquinic acid treatment reduced the expression of tyrosinase-related protein-1. Significantly, we could validate the antipigmentation activity of this compoundin vivo, using a zebrafish model. Moreover, 4,5-O-dicaffeoylquinic acid did not show toxicity in this animal model. Our discovery of 4,5-O-dicaffeoylquinic acid as an inhibitor of pigmentation that is activein vivoshows that this compound can be developed as an active component for formulations to treat pigmentation disorders.

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12

Nowak, Jadwiga, Anna K. Kiss, Charles Wambebe, Esther Katuura, and Łukasz Kuźma. "Phytochemical Analysis of Polyphenols in Leaf Extract from Vernonia amygdalina Delile Plant Growing in Uganda." Applied Sciences 12, no. 2 (January 17, 2022): 912. http://dx.doi.org/10.3390/app12020912.

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Due to the presence of phytochemicals, plants have been known to be used in the treatment and management of various diseases. Vernonia amygdalina, belonging to the Asteraceae family, is a plant known for its many applications in traditional medicine for various purposes. Previous studies on the methanolic leaf extract of this plant have proved the antibacterial, cytotoxic, anticancer and antioxidant effects indicative of promising therapeutic potentials. In this work, chromatographic and spectroscopic techniques along with high-performance liquid chromatography quantitative analysis were adopted to isolate, identify and quantify polyphenolic compounds in V. amygdalina leaf extract. UHPLC-DAD-ESI-MS/MS and UHPLC-DAD methods were adopted for qualitative and quantitative analysis, respectively. In the case of polyphenol separation, some reference substances were isolated by preparative HPLC. Seven polyphenols were identified and quantified in this study: 5-O-caffeoylquinic acid, luteolin hexoside, 3,4-O-dicaffeoylquinic acid, 1,5-O-dicaffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, 4,5-O-dicaffeoylquinic acid and luteolin dihexoside, with 3,5-O-dicaffeoylquinic acid being isolated in the highest quantity of 27.49 mg g−1 extract.

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Dai, Ying, Zhihua Dou, Rongrong Zhou, Lin Luo, Li Bian, Yufeng Chen, Jinhua Tao, and Zhixian Chen. "Quality Evaluation of Artemisia capillaris Thunb. Based on Qualitative Analysis of the HPLC Fingerprint and UFLC-Q-TOF-MS/MS Combined with Quantitative Analysis of Multicomponents." Journal of Analytical Methods in Chemistry 2021 (April 21, 2021): 1–13. http://dx.doi.org/10.1155/2021/5546446.

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In this study, a new method was developed for the comprehensive quality evaluation (QE) of Artemisia capillaris Thunb. (A. capillaris, named Yinchenhao in Chinese), which is one of the most commonly used herbal medicines (HMs). First, fingerprints of 31 batch samples of A. capillaris were determined by HPLC, the reference fingerprint was established, and the common peaks were assigned. Second, the components of common peaks in the HPLC fingerprints were identified by ultrafast liquid chromatography- (UFLC-) Q-TOF-MS/MS. Finally, the contents of the components unambiguously confirmed by reference substances were determined, and the correlation between the contents of chlorogenic acid and the contents of others was analyzed. The results showed that there were 20 common peaks in the HPLC fingerprints of 31 batch samples. The components of these 20 common peaks were identified as ten organic acids, eight flavonoids, and two others. Among nine organic acids such as 1-caffeoylquinic acid, neochlorogenic acid, chlorogenic acid, caffeic acid, cryptochlorogenic acid, 1,3-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid, three flavonoids such as rutin, hyperoside, and isoquercetin, and one other p-hydroxyacetophenone, a total of 13 ones were unambiguously identified by comparison with reference substances; one caffeoylquinic acid glucoside and one flavone di-C-glucoside were detected in A. capillaris for the first time. There were some differences in the contents of 13 components in different samples; chlorogenic acid could be regarded as the quality marker of A. capillaris. The current established method in this study can be used for the comprehensive QE of A. capillaris and can also provide reference for the QE of the other HMs.

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Choi, Jun-Hui, Ki-Man Kim, Se-Eun Park, Myung-Kon Kim, and Seung Kim. "Short-Term Effects of PJE Administration on Metabolic Parameters in Diet-Induced Obesity Mice." Foods 12, no. 8 (April 17, 2023): 1675. http://dx.doi.org/10.3390/foods12081675.

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The study investigated the effects of Petasites japonicus (Siebold & Zucc.) Maxim. extract (PJE) and fenofibrate on diet-induced obesity (DIO) in mice. PJE was found to contain various bio-active polyphenolic compounds, including kaempferol, p-hydroxybenzoic acid, ferulic acid, gallic acid, chlorogenic acid, 3,4-dicaffeoylquinic acid, caffeic acid, quercetin, rutin, protocatechuic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, p-coumaric acid, apigenin, and 1,3-dicaffeoylquinic acid. The results showed that PJE treatment up to 1000 μg/mL did not affect the viability of 3T3-L1 cell line, and it reduced the feed efficiency ratio in DIO mice. PJE administration also resulted in a significant reduction in body weight gain and fat accumulation in the liver compared to the DIO control group. Additionally, PJE administration improved the levels of lipid and related parameters, including total cholesterol, triacylglycerol, low-density lipoprotein, very low-density lipoprotein, glucose, insulin, insulin resistance, leptin, and atherogenic or cardiac indexes compared to the DIO control group. The study suggested that PJE may have a beneficial effect on insulin resistance, lipid profiles, atherogenesis, adipokines, and cardiac risk associated with diet-induced obesity.

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Tsevegsuren, N., P. Proksch, Y. Wang, and G. Davaakhuu. "Bioactive phenolic acids from Scorzonera radiata Fisch." Mongolian Journal of Chemistry 12 (September 24, 2014): 78–84. http://dx.doi.org/10.5564/mjc.v12i0.177.

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Chromatographic separation of the crude extract obtained from the aerial parts of the Mongolian medicinal plant Scorzonera radiata yielded five new dihydrostilbenes [4], two new flavonoids, one new quinic acid derivative, as well as twenty known compounds including eight quinic acid derivatives, four flavonoids, two coumarins, five simple benzoic acids, and one monoterpene glycoside. We present here results on isolation and structural identification some active phenolic compounds from the Scorzonera radiata - eight quinic acid derivatives (quinic acid, 4,5-dicaffeoylquinic acid, 4,5-dicaffeoyl-epi-quinic acid, 3,5-dicaffeoylquinic acid, 3,5-dicaffeoyl-epi-quinic acid, chlorogenic acid, 5-p-coumaroylquinic acid (trans), 5-p-coumaroylquinic acid (cis)). Quinic acid derivatives exhibited antioxidative activity.DOI: http://dx.doi.org/10.5564/mjc.v12i0.177 Mongolian Journal of Chemistry Vol.12 2011: 78-84

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Xia, Zhengyan, Yiming Sun, Chengyong Cai, Yong He, and Pengcheng Nie. "Rapid Determination of Chlorogenic Acid, Luteoloside and 3,5-O-dicaffeoylquinic Acid in Chrysanthemum Using Near-Infrared Spectroscopy." Sensors 19, no. 9 (April 28, 2019): 1981. http://dx.doi.org/10.3390/s19091981.

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The feasibility of near-infrared spectroscopy (NIR) to detect chlorogenic acid, luteoloside and 3,5-O-dicaffeoylquinic acid in Chrysanthemum was investigated. An NIR spectroradiometer was applied for data acquisition. The reference values of chlorogenic acid, luteoloside, and 3,5-O-dicaffeoylquinic acid of the samples were determined by high-performance liquid chromatography (HPLC) and were used for model calibration. The results of six preprocessing methods were compared. To reduce input variables and collinearity problems, three methods for variable selection were compared, including successive projections algorithm (SPA), genetic algorithm-partial least squares regression (GA-PLS), and competitive adaptive reweighted sampling (CARS). The selected variables were employed as the inputs of partial least square (PLS), back propagation-artificial neural networks (BP-ANN), and extreme learning machine (ELM) models. The best performance was achieved by BP-ANN models based on variables selected by CARS for all three chemical constituents. The values of rp2 (correlation coefficient of prediction) were 0.924, 0.927, 0.933, the values of RMSEP were 0.033, 0.018, 0.064 and the values of RPD were 3.667, 3.667, 2.891 for chlorogenic acid, luteoloside, and 3,5-O-dicaffeoylquinic acid, respectively. The results indicated that NIR spectroscopy combined with variables selection and multivariate calibration methods could be considered as a useful tool for rapid determination of chlorogenic acid, luteoloside, and 3,5-O-dicaffeoylquinic acid in Chrysanthemum.

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Li, Yonghui, Peixiang Wang, Wei Xiao, Li Zhao, Zhenzhong Wang, and Li Yu. "Screening and Analyzing the Potential Bioactive Components from Reduning Injection, Using Macrophage Cell Extraction and Ultra-High Performance Liquid Chromatography Coupled with Mass Spectrometry." American Journal of Chinese Medicine 41, no. 01 (January 2013): 221–29. http://dx.doi.org/10.1142/s0192415x1350016x.

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In this paper, a useful method for screening and analyzing the potential bioactive components from Reduning Injection was developed using macrophage cell extraction and ultra-high performance liquid chromatography coupled with Q-TOF/MS spectrometry. In addition, the protective effects on macrophage cell damage induced by LPS in vitro were also investigated. The results showed that chlorogenic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid and 4, 5-dicaffeoylquinic acid significantly inhibited the prostaglandin E2 (PGE2) release and reversed the interleukin-6 (IL-6) secretion of macrophages (p < 0.05). These data indicated that the method of macrophage cell extraction coupled with UPLC-MS technology is feasible, rapid and useful for screening and analyzing potential bioactive components from TCM injection.

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Uranishi, Rei, Raju Aedla, Doaa H. M. Alsaadi, Dongxing Wang, Ken Kusakari, Hirotaka Osaki, Koji Sugimura, and Takashi Watanabe. "Evaluation of Environmental Factor Effects on the Polyphenol and Flavonoid Content in the Leaves of Chrysanthemum indicum L. and Its Habitat Suitability Prediction Mapping." Molecules 29, no. 5 (February 20, 2024): 927. http://dx.doi.org/10.3390/molecules29050927.

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The leaves of Chrysanthemum indicum L. are known to have various bioactive compounds; however, industrial use is extremely limited. To overcome this situation by producing high-quality leaves with high bioactive content, this study examined the environmental factors affecting the phytochemical content and antioxidant activity using C. indicum leaves collected from 22 sites in Kochi Prefecture, Japan. Total phenolic and flavonoid content in the dry leaves ranged between 15.0 and 64.1 (mg gallic acid g−1) and 2.3 and 11.4 (mg quercetin g−1), while the antioxidant activity (EC50) of the 50% ethanol extracts ranged between 28.0 and 123.2 (µg mL−1) in 1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay. Among the identified compounds, chlorogenic acid and 1,5-dicaffeoylquinic acid were the main constituents in C. indicum leaves. The antioxidant activity demonstrated a positive correlation with 1,5-dicaffeoylquinic acid (R2 = 0.62) and 3,5-dicaffeoylquinic acid (R2 = 0.77). The content of chlorogenic acid and dicaffeoylquinic acid isomers varied significantly according to the effects of exchangeable magnesium, cation exchange capacity, annual temperature, and precipitation, based on analysis of variance. The habitat suitability map using the geographical information system and the MaxEnt model predicted very high and high regions, comprising 3.2% and 10.1% of the total area, respectively. These findings could be used in future cultivation to produce high-quality leaves of C. indicum.

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Ayrapetyan, E. E., M. V. Larsky, and D. A. Konovalov. "Identification of phenolic compounds in Artemisia scoparia." Farmaciya (Pharmacy) 73, no. 3 (July 7, 2024): 14–17. http://dx.doi.org/10.29296/25419218-2024-04-02.

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Анотація:

Introduction. Artemisia scoparia herba is a valuable source of biologically active compounds. Due to its rich chemical composition, the raw material has wide pharmacological effects. Purpose of the study. Identification of some phenolic compounds and the quantitative determination of scoparone, scopoletin, umbelliferonein Artemisia scoparia herba by high performance liquid chromatography (HPLC). Material and methods. The investigated object is Artemisia scoparia herba, collected during the flowering phase in the Nikitsky Botanical Garden in 2018–2019. Qualitative determination of phenolic compounds was provided by HPLC with mass-spectrometry detection (HPLC-MS). Results. The following phenolic compounds were identified by HPLC-MS: scopoletin, rutin, hyperoside, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, luteolin. Conclusion. The possibility of qualitative and quantitative determination of phenolic compounds from plant raw materials by HPLC is shown.

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Chiu, Chun-Hui, Kuan-Hung Lin, Hsin-Hung Lin, Wen-Xin Chu, Yung-Chang Lai, and Pi-Yu Chao. "Analysis of Chlorogenic Acid in Sweet Potato Leaf Extracts." Plants 11, no. 15 (August 7, 2022): 2063. http://dx.doi.org/10.3390/plants11152063.

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Sweet potato (Ipomoea batatas L.) is one of the most important food crops worldwide, with leaves of different varieties showing purple, green and yellow, and these leaves provide a dietary source of nutrients and various bioactive compounds. The objective of this study was to identify the active constituents of chlorogenic acids (CGAs) in different methanolic extract of leaves of three varieties of sweet potato (purple CYY 98-59, green Taoyuan 2, and yellow CN 1927-16) using liquid chromatography–tandem mass spectrometry. Genotype-specific metabolite variations were observed; CGAs and three isomeric peaks were detected in sweet potato leaf extracts (SPLEs). Among them, the yellow SPLE contained the highest contents of 3,5-dicaffeoylquinic acid (3,5-di-CQA) and 3,4-dicaffeoylquinic acid (3,4-di-CQA), followed by the green SPLE, whereas the purple SPLE retained lower 3,5-di-CQA content compared to yellow and green SPLEs. All three SPLEs contained lower 4,5-dicaffeoylquinic acid (4,5-di-CQA) and CGA contents compared to 3,5-di-CQA and 3,4-di-CQA, although CGA constituents were not significantly different in genotypes, whereas purple SPLE contained higher 4,5-di-CQA content compared to yellow and green SPLEs. This study indicates that SPLs marketed in Taiwan vary widely in their biological potentials and may impart different health benefits to consumers.

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Ilina, Tetiana, Natalia Kashpur, Sebastian Granica, Agnieszka Bazylko, Igor Shinkovenko, Alla Kovalyova, Olga Goryacha, and Oleh Koshovyi. "Phytochemical Profiles and In Vitro Immunomodulatory Activity of Ethanolic Extracts from Galium aparine L." Plants 8, no. 12 (November 25, 2019): 541. http://dx.doi.org/10.3390/plants8120541.

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Galium aparine L., family Rubiaceae, is a widely spread species in the Galium genus. The herb of G. aparine is part of folk remedies and dietary supplements. In this study, we analyzed the chemical composition and immunomodulatory activities of G. aparine herb ethanolic extracts obtained from the plant material by maceration with 20%, 60% or 96% ethanol. The contents of hydroxycinnamic acid derivatives, flavonoids and polyphenols were determined spectrophotometrically, with extractives and polysaccharides quantified gravimetrically. The qualitative composition was studied using UHPLC-DAD-MS/MS analysis; isolation not previously described in G. aparine quercetin rhamnoglucoside was carried out through column chromatography, and the immunomodulatory activity of extracts was determined in the reaction of lymphocyte blast transformation. Major constitutes of extracts were iridoids, i.e., monotropein, 10-desacetylasperulosidic acid and asperulosidic acid; p-hydroxybenzoic acid; hydroxycinnamic acid derivatives, i.e., 3-O-caffeoylquinic, 5-O-caffeoylquinic, 3,4-O-dicaffeoylquinic, 3,5-O-dicaffeoylquinic, 4,5-O-dicaffeoylquinic acids and caffeic acid derivatives; flavonoids, i.e., rutin, quercetin 3-O-rhamnoglucoside-7-O-glucoside, and isorhamnetin 3-O-glucorhamnoside. Significantly, quercetin 3-O-rhamnoglucoside-7-O-glucoside was first isolated and identified in Galium species so far investigated. All G. aparine herb ethanolic extracts stimulate the transformational activity of immunocompetent blood cells, with 96% ethanolic extract being the most active. The data obtained necessitate further research into the mechanisms of immunomodulatory activity of extracts from G. aparine herb.

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Moldoch, Jaroslaw, Barbara Szajwaj, Milena Masullo, Lukasz Pecio, Wieslaw Oleszek, Sonia Piacente, and Anna Stochmal. "Phenolic Constituents of Knautia arvensis Aerial Parts." Natural Product Communications 6, no. 11 (November 2011): 1934578X1100601. http://dx.doi.org/10.1177/1934578x1100601117.

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A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

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Wu, Yi-Hang, Bing-Jie Hao, Hong-Cui Cao, Wei Xu, Yong-Jun Li, and Lan-Juan Li. "Anti-Hepatitis B Virus Effect and Possible Mechanism of Action of 3,4-O-Dicaffeoylquinic AcidIn VitroandIn Vivo." Evidence-Based Complementary and Alternative Medicine 2012 (2012): 1–9. http://dx.doi.org/10.1155/2012/356806.

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The anti-hepatitis B activity of 3,4-O-dicaffeoylquinic acid isolated fromLaggera alatawas studied using theD-galactosamine- (D-GalN-) induced hepatocyte damage model, HepG2.2.15 cells, and with HBV transgenic mice.In vitroresults showed that 3,4-O-dicaffeoylquinic acid improved HL-7702 hepatocyte viability and markedly inhibited the production of HBsAg and HBeAg. At a concentration of 100 μg/mL, its inhibitory rates on the expression levels of HBsAg and HBeAg were 89.96% and 81.01%, respectively. The content of hepatitis B virus covalently closed circular DNA (HBV cccDNA) in HepG2.2.15 cells was significantly decreased after the cells were treated with the test compound. In addition, 3,4-O-dicaffeoylquinic acid significantly increased the expression of heme oxygenase-1 (HO-1) in HepG2.2.15 cells.In vivoresults indicated that the test compound at concentrations of 100 μg/mL significantly inhibited HBsAg production and increased HO-1 expression in HBV transgenic mice. In conclusion, this study verifies the anti-hepatitis B activity of 3,4-O-dicaffeoylquinic acid. The upregulation of HO-1 may contribute to the anti-HBV effect of this compound by reducing the stability of the HBV core protein, which blocks the refill of nuclear HBV cccDNA. Furthermore, the hepatoprotective effect of this compound may be mediated through its antioxidative/anti-inflammatory properties and by the induction of HO-1 expression.

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Grunennvaldt, Renata Lucia, Juliana Degenhardt-Goldbach, Jessica de Cassia Tomasi, Fabricio Augusto Hansel, Bruno Portela Brasileiro, Peter Brooks, Erik Nunes Gomes, Uberson Boaretto Rossa, and Cicero Deschamps. "Ilex paraguariensis: the effect of genotypes and growth phase on biomass, secondary metabolism and antioxidant activity of in vitro cultivated calli." Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas 21, no. 4 (July 30, 2022): 548–60. http://dx.doi.org/10.37360/blacpma.22.21.4.33.

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Yerba mate (Ilex paraguariensis) produces several secondary metabolites of interest to the pharmaceutical industry, such as chlorogenic acids and methylxanthines. These compounds have been produced in vitro by callus culture from different species. However, for I. paraguariensis, no studies upon the production of these compounds in vitro have been performed to date. In this work, we show that the concentration of secondary metabolites from I. paraguariensis callus is possible and highly dependent on the callus growth phase. We observed that the best phase for the production of secondary compounds in calli of yerba mate is the stationary growth phase on both genotypes tested. In this phase, higher levels of phenolic compounds, chlorogenic acid and 3,5-dicaffeoylquinic acid and greater antioxidant activity were observed. Chlorogenic acid and 3,5-dicaffeoylquinic acid presented positive correlation with antioxidant activity. For the first time, secondary compounds were reported in yerba mate calli cultivated in vitro.

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Fontanel, D., C. Galtier, C. Viel, and A. Gueiffier. "Caffeoyl Quinic and Tartaric Acids and Flavonoids from Lapsana communis L. subsp. communis (Asteraceae)." Zeitschrift für Naturforschung C 53, no. 11-12 (December 1, 1998): 1090–92. http://dx.doi.org/10.1515/znc-1998-11-1224.

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Abstract Six hydroxycinnamic acids : caffeic acid, chlorogenic acid, 3,5-O-dicaffeoylquinic acid 2-O-caffeoyltartaric acid (caftaric acid) and 2,3-O-dicaffeoyltartaric acid (chicoric acid) have been isolated from Lapsana communis L. subsp. communis aerial parts. Among flavonoids, only isoquercitrin, luteolin and luteolin-7-O-β-glucuronide were identified. Except for chlorogenic acid, these com pounds represent the first report in Lapsana communis. Chicoric acid is the major phenylpropanoic constituent in this plant.

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He, Juan, Susu Zhu, Bingquan Chu, Xiulin Bai, Qinlin Xiao, Chu Zhang, and Jinyan Gong. "Nondestructive Determination and Visualization of Quality Attributes in Fresh and Dry Chrysanthemum morifolium Using Near-Infrared Hyperspectral Imaging." Applied Sciences 9, no. 9 (May 13, 2019): 1959. http://dx.doi.org/10.3390/app9091959.

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Rapid and nondestructive determination of quality attributes in fresh and dry Chrysanthemum morifolium is of great importance for quality sorting and monitoring during harvest and trade. Near-infrared hyperspectral imaging covering the spectral range of 874–1734 nm was used to detect chlorogenic acid, luteolin-7-O-glucoside, and 3,5-O-dicaffeoylquinic acid content in Chrysanthemum morifolium. Fresh and dry Chrysanthemum morifolium flowers were studied for harvest and trade. Pixelwise spectra were preprocessed by wavelet transform (WT) and area normalization, and calculated as average spectrum. Successive projections algorithm (SPA) was used to select optimal wavelengths. Partial least squares (PLS), extreme learning machine (ELM), and least-squares support vector machine (LS-SVM) were used to build calibration models based on full spectra and optimal wavelengths. Calibration models of fresh and dry flowers obtained good results. Calibration models for chlorogenic acid in fresh flowers obtained best performances, with coefficient of determination (R2) over 0.85 and residual predictive deviation (RPD) over 2.50. Visualization maps of chlorogenic acid, luteolin-7-O-glucoside, and 3,5-O-dicaffeoylquinic acid in single fresh and dry flowers were obtained. The overall results showed that hyperspectral imaging was feasible to determine chlorogenic acid, luteolin-7-O-glucoside, and 3,5-O-dicaffeoylquinic acid. Much more work should be done in the future to improve the prediction performance.

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Roh, Kyung-Baeg, Youngsu Jang, Eunae Cho, Deokhoon Park, Dae-Hyuk Kweon, and Eunsun Jung. "Chlorogenic Acid Isomers Isolated from Artemisia lavandulaefolia Exhibit Anti-Rosacea Effects In Vitro." Biomedicines 10, no. 2 (February 16, 2022): 463. http://dx.doi.org/10.3390/biomedicines10020463.

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Rosacea is a chronic inflammatory disease affecting facial skin. It is associated with immune and vascular dysfunction mediated via increased expression and activity of cathelicidin and kallikrein 5 (KLK5), a serine protease of stratum corneum. Therefore, KLK5 inhibitors are considered as therapeutic agents for improving the underlying pathophysiology and clinical manifestation of rosacea. Here, we isolated the active constituents of Artemisia lavandulaefolia (A. lavandulaefolia) and investigated their inhibitory effect on KLK5 protease activity. Using bioassay-guided isolation, two bioactive compounds including chlorogenic acid isomers, 3,5-dicaffeoylquinic acid (isochlorogenic acid A) (1), and 4,5-dicaffeoylquinic acid (isochlorogenic acid C) (2) were isolated from A. lavandulaefolia. In this study, we evaluated the effects of isochlorogenic acids A and C on dysregulation of vascular and immune responses to rosacea, and elucidated their molecular mechanisms of action. The two chlorogenic acid isomers inhibit KLK5 protease activity, leading to reduced conversion of inactive cathelicidin into active LL-37. This inhibition of LL-37 production by isochlorogenic acids A and C reveals the efficacy of suppressing the expression of inflammatory mediators induced by LL-37 in immune cells such as macrophages and mast cells. In addition, both isomers of chlorogenic acid directly inhibited the proliferation and migration of vascular endothelial cells induced by LL-37.

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Zhang, Chengcheng, Daqun Liu, Liehong Wu, Jianming Zhang, Xiaoqiong Li, and Weicheng Wu. "Chemical Characterization and Antioxidant Properties of Ethanolic Extract and Its Fractions from Sweet Potato (Ipomoea batatas L.) Leaves." Foods 9, no. 1 (December 23, 2019): 15. http://dx.doi.org/10.3390/foods9010015.

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Sweet potato (Ipomoea batatas L.) leaf is a natural source of phenolic compounds with strong antioxidant activity and potential utility as an antioxidant. The aim of this study was to evaluate the polyphenol composition and antioxidant activities of ethanol extracts and their various solvent-partitioned fractions (petroleum ether, ethyl acetate, and aqueous fraction) from sweet potato leaves and petioles. Seven caffeoylquinic acid (CQA) derivatives and four flavonoids were detected in sweet potato leaves by HPLC-ESI-MS. The total phenolic content (TPC) and total flavonoid content (TFC) in leaf (112.98 ± 4.14 mg gallic acid equivalent (GAE)/g of dried extract, 56.87 ± 5.69 mg rutin equivalent (RE)/g of dried extract) was more than ten times higher than in petiole (9.22 ± 2.67 mg GAE/g of dried extract, 3.81 ± 0.52 mg RE/g of dried extract). The antioxidant contents of ethyl acetate fractions increased dramatically relative to those of crude extracts for both leaves and petioles. Purification using solvent partition with ethyl acetate increased TPC and TFC of crude extracts, especially the CQA derivatives including 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and 3,4,5-tricaffeoylquinic acid. Meanwhile, the ethyl acetate fractions with the highest CQA content were associated with the highest scavenging activities towards 2,2-diphenyl-1-picrylhydrazyl (DPPH) and higher ferric ion reducing antioxidant power (FRAP)-reducing power.

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Moyo, Siphosanele Mafa, June C. Serem, Megan J. Bester, Vuyo Mavumengwana, and Eugenie Kayitesi. "Hydrothermal Processing and In Vitro Simulated Human Digestion Affects the Bioaccessibility and Bioactivity of Phenolic Compounds in African Pumpkin (Momordica balsamina) Leaves." Molecules 26, no. 17 (August 27, 2021): 5201. http://dx.doi.org/10.3390/molecules26175201.

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The African pumpkin (Momordica balsamina) contains bioactive phenolic compounds that may assist in reducing oxidative stress in the human body. The leaves are mainly consumed after boiling in water for a specific time; this hydrothermal process and conditions of the gastrointestinal tract may affect the presence and bioactivity of phenolics either positively or negatively. In this study, the effects of hydrothermal processing (boiling) and in vitro simulated human digestion on the phenolic composition, bioaccessibility and bioactivity in African pumpkin were investigated in comparison with those of spinach (Spinacia oleracea). A high-resolution ultra-performance liquid chromatography, coupled with diode array detection, quadrupole time-of-flight and mass spectrometer (UPLC-DAD-QTOF-MS) was used to profile phenolic metabolites. Metabolites such as 3-caffeoylquinic acid, 5-caffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid were highly concentrated in the boiled vegetable extracts compared to the raw undigested and all digested samples. The majority of African pumpkin and spinach extracts (non-digested and digested) protected Deoxyribonucleic acid (DNA), (mouse fibroblast) L929 and human epithelial colorectal adenocarcinoma (Caco-2) cells from 2,2′-Azobis(2-methylpropionamidine) dihydrochloride (AAPH)-induced oxidative damage. From these results, the consumption of boiled African pumpkin leaves, as well as spinach, could be encouraged, as bioactive metabolites present may reduce oxidative stress in the body.

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Nguyễn, Thị Ánh Nguyệt, Đại Thạnh Thi, Tấn Phát Nguyễn, Minh Tài Lê та Thị Kim Chi Lữ. "Phân lập một số hợp chất acid dicaffeoylquinic từ cao ethyl acetat của rễ Sài hồ nam (Pluchea pteropoda Hemsl.)". Y HOC TP. HO CHI MINH 27, № 3 (28 вересня 2024): 19–26. http://dx.doi.org/10.32895/hcjm.p.2024.03.03.

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Đặt vấn đề: Sài hồ nam còn gọi là Lức (Pluchea pteropoda Hemsl., Asteraceae) là cây thuốc được dùng để chữa nóng sốt, cảm cúm, nhức đầu. Sài hồ nam thường mọc tự nhiên và phát triển ở môi trường sống ven biển. Các nghiên cứu hóa học của rễ Sài hồ nam chưa có nhiều hiện nay. Các tiêu chuẩn chất lượng của lá và rễ Sài hồ nam của Dược điển Việt Nam V còn khá đơn giản; chưa có phương pháp định tính và định lượng thành phần chính. Mục tiêu: Mục tiêu của đề tài là chiết xuất, phân lập các thành phần chính của rễ Sài hồ nam nhằm phục vụ cho việc tiêu chuẩn hóa dược liệu. Đối tượng - Phương pháp nghiên cứu: Từ 5 kg bột rễ Sài hồ nam được chiết ngấm kiệt với ethanol 96% và dịch chiết đậm đặc sau đó được lắc phân bố với dicloromethan, ethyl acetat và n-butanol. Phân lập các chất được thực hiện trên cao ethyl acetat (26,14 g) bằng các kĩ thuật sắc ký cột (VLC, Sephadex và sắc ký lỏng bán điều chế). Cấu trúc hóa học của các chất phân lập được xác định bằng phổ HRMS và NMR kết hợp so sánh với tài liệu tham khảo. Kết quả: Ba hợp chất đã phân lập và xác định gồm (1) acid 3,4-dicaffeoylquinic (161,47 mg); (2) acid 3,5-dicaffeoylquinic (18,93 mg) và (3) acid 4,5-dicaffeoylquinic (87,86 mg). Kết luận: Cả 3 hợp chất này lần đầu được phân lập ở loài Pluchea pteropoda. Từ khoá: acid dicaffeoylquinic, Pluchea pteropoda, Sài hồ nam, Lức

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Gocmanac-Ignjatovic, Marija, Dusanka Kitic, Mirjana Radenkovic, Milica Kostic, Milica Milutinovic, Gorana Nedin-Rankovic, and Suzana Brankovic. "The effect of the aqueous and methanol fennel stem extracts (Foeniculum vulgare Miller) on isolated rat ileum contractility." Vojnosanitetski pregled 75, no. 8 (2018): 809–14. http://dx.doi.org/10.2298/vsp161001391g.

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Background/Aim. The fennel (Foeniculum vulgare Miller, Apiaceae) has a long history of use as traditional herb medicine due to its carminative properties. The study was aimed to investigate the effects of aqueous and methanol fennel stem extracts on intestinal activity. Methods. Relaxant activity of aqueous and methanol fennel stem extracts was evaluated in vitro in three experimental models: spontaneous contraction, acetylcholine and potassium chloride (KCl)-induced contraction of an isolated rat ileum. The composition of aqueous and methanol fennel stem extracts was qualitatively analyzed using the high performance liquid chromatographic (HPLC) analysis. Results. In the presence of an aqueous fennel stem extract at a concentration of 3 mg/mL, the inhibition of the spontaneous contractions of isolated rat ileum was 35.05% ? 3.57%. In presence of a methanol fennel stem extract at the same concentration, the maximum reduction of the spontaneous contractions was 48.91% ? 6.31%. The extracts in a concentration- dependent manner significantly inhibited the acetylcholine and KCl induced contractions of the isolated rat ileum (p < 0.01). The following components were identified in fennel methanol stem extract: 3-caffeoylquinic acid, chlorogenic acid, 4-caffeoylquinic acid, 1,3-dicaffeoylquinic acid, rutin, miquelianin, quercetin heterosides, 1,5-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, apigenin and rosmarinic acid. In an aqueous extract, their presence is found in trace amounts. Conclusion. The results of this study showed that the aqueous and methanol fennel stem extracts have spasmolytic effects on the intestinal smooth muscle and may be used for the control of intestinal motility.

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Polakova, Katarina, Alica Bobková, Marek Bobko, Ľubomír Belej, and Andrea Mesárošová. "ANALYSIS OF CHEMICAL ATTRIBUTES BASED ON IDENTIFICATON MARKERS TO DIFFERENTIATE MEDIUM ROASTED COFFEA ARABICA REGARDING DIFFERENT GEOGRAPHICAL ORIGIN." Journal of microbiology, biotechnology and food sciences 13, no. 5 (January 24, 2024): e10540. http://dx.doi.org/10.55251/jmbfs.10540.

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Traceability in the coffee supply chain is crucial for ensuring transparency and authenticity. It helps safeguard the interests of both producers and consumers by minimizing the risk of fraudulent practices and ensuring fair trade. Different geographical origins can lead to variances in coffee taste, quality of product and economic value. Just because controlling the authenticity of the geographical origin of coffee beans is of great importance for producers and consumers worldwide. This study determined parameters (caffeine, chlorogenic acids, total antioxidant capacity (TAC), total polyphenols content (TPC) volatile compounds, pH, water activity aw and dry matter) based on which was testing classification of geographical origin of coffee beans. For this research, six samples of 100% Coffea arabica medium roasting coffee beans, from the two major growing country of America and Africa were studied. As part of the research, variability in chemical composition based on geographical origin was confirmed. For America samples were significant parameters TAC, 4.5-dicaffeoylquinic acid, 3.5-dicaffeoylquinic acid, caffeine and chlorogenic acids. Second group was sample from Africa. For these samples was determine parameter like TPC, cryptochlorogenic acid, neochlorogenic acid and pH. Volatile substances, caffeine, pH, chlorogenic acids were considered the most important parameters that can help to identify the geographical origin.

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Antognoni, Fabiana, Nicoletta Crespi Perellino, Sergio Crippa, Roberto Dal Toso, Bruno Danieli, Anacleto Minghetti, Ferruccio Poli, and Giovanna Pressi. "Irbic acid, a dicaffeoylquinic acid derivative from Centella asiatica cell cultures." Fitoterapia 82, no. 7 (October 2011): 950–54. http://dx.doi.org/10.1016/j.fitote.2011.05.008.

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Tezuka, Yasuhiro, Keiichi Yamamoto, Suresh Awale, Feng Li, Satoshi Yomoda, and Shigetoshi Kadota. "Anti-austeric Activity of Phenolic Constituents of Seeds of Arctium lappa." Natural Product Communications 8, no. 4 (April 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800414.

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From seeds of Arctium lappa L. (Asteraceae) we obtained arctigenin (1), arctiin (2), chlorogenic acid (3), 4,5-dicaffeoylquinic acid (4), 3,5-dicaffeoylquinic acid (5), 3,4-dicaffeoylquinic acid (6), matairesinol (11), isolappaol A (12), lappaol F (14), and lappaol B (15), together with 1:1 mixtures of isolappaol C (7) and lappaol C (8), arctignan E (9) and arctignan D (10), and 12 and lappaol A (13), while 3,3′,4′-tri- O-demethylarctigenin (16), 3,3′-di- O-demethyl-4′-dehydroxyarctigenin (17), and 3- O-demethylarctigenin (18) were obtained by anaerobic microbiological metabolism of 1. Then, we evaluated the in vitro preferential cytotoxic activity of these pure compounds and 1:1 mixtures, together with enterodiol (19) and enterolactone (20), against human pancreatic cancer PANC-1 cells in nutrient-deprived medium (NDM). Among them, 1 and 18 showed potent activity, with PC50 values of 1.75 and 4.38 μ M, respectively, while 11, 15, and 17 showed mild activity with PC50 values of 31.1, 30.9, and 38.7 μ/M, respectively. By comparing their structures and PC50 values, the following structural moieties could be concluded to be important for the preferential cytotoxicity of 1: 1) the 3-hydroxy-4-methoxyphenyl group at the 2-position on the γ-butyrolactone ring, 2) the less polar substituent at the 3-position on the γ-butyrolactone ring, and 3) the γ-butyrolactone ring.

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Li, Fangliang, Leyan Xiao, Xue Lin, Jincheng Dai, Jiale Hou, and Lu Wang. "Deep Eutectic Solvents-Based Ultrasound-Assisted Extraction of Antioxidants from Kudingcha (llex kudingcha C.J. Tseng): Process Optimization and Comparison with Other Methods." Foods 12, no. 9 (April 30, 2023): 1872. http://dx.doi.org/10.3390/foods12091872.

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Kudingcha (KDC) is an important tea substitute containing abundant antioxidants. Herein, a ultrasonic-assisted extraction (UAE) technique based on deep eutectic solvents (DESs) was applied to optimize the total phenolic/total flavonoid content (TPC/TFC) from the KDC extracts. Results indicated that DES composed of L-proline and glycerol (Pro-Gly) had excellent extraction performance for TPC, TFC, ABTS•+ and FRAP, which were significantly better than other solvents. Response surface methodology (RSM) was used to obtain optimal extraction parameters for simultaneously maximizing the TPC, TFC and antioxidant activity. Results revealed that water content in Pro-Gly, liquid to solid ratio (L/S), ultrasonic temperature and extraction time were the major influence factors of the TPC, TFC, ABTS•+ and FRAP of the KDC extracts. The optimal conditions included water content in Pro-Gly of 46.4%, L/S of 25:1 (mL/g), ultrasonic temperature of 55 °C and extraction time of 50 min. Meanwhile, HPLC-MS/MS was adopted to identify the KDC extracts, which revealed the presence of major phytochemicals, including 5-chlorogenic acid, 4,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, kaempferol 3-rutinoside, myricetin and isorhamnetin. Moreover, UAE–Pro-Gly achieved further higher individual phenolics contents, TPC, TFC, ABTS•+ and FRAP than other methods. In conclusion, UAE–Pro-Gly is a highly efficient method for extraction of phenolic antioxidants from KDC.

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36

Kim, Jung-Hoon, Hye-Sun Lim, Hyekyung Ha, Chang-Seob Seo та Hyeun-Kyoo Shin. "Inulae Flos and Its Compounds Inhibit TNF-α- and IFN-γ-Induced Chemokine Production in HaCaT Human Keratinocytes". Evidence-Based Complementary and Alternative Medicine 2012 (2012): 1–11. http://dx.doi.org/10.1155/2012/280351.

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The present study is to investigate which kinds of solvent extracts of Inulae Flos inhibit the chemokine productions in HaCaT cell and whether the inhibitory capacity of Inulae Flos is related with constitutional compounds. The 70% methanol extract showed comparatively higher inhibition of thymus and activation-regulated chemokine (TARC/CCL17) in HaCaT cells, therefore this extract was further partitioned with n-hexane, chloroform, ethyl acetate, butanol, and water. The ethyl acetate fraction inhibited TARC, macrophage-derived chemokine (MDC/CCL22), and regulated on activation of normal T-cell-expressed and -secreted (RANTES/CCL5) production in HaCaT cells better than the other fractions. The compounds of Inulae Flos, such as 1,5-dicaffeoylquinic acid and luteolin, inhibited TARC, MDC, and RANTES production in HaCaT cells. 1,5-Dicaffeoylquinic acid was contained at the highest concentrations both in the 70% methanol extract and ethyl acetate fraction and inhibited the secretion of chemokines dose-dependently more than the other compounds. Luteolin also represented dose-dependent inhibition on chemokine productions although it was contained at lower levels in 70% methanol extract and solvent fractions. These results suggest that the inhibitory effects of Inulae Flos on chemokine production in HaCaT cell could be related with constituent compounds contained, especially 1,5-dicaffeoylquinic acid and luteolin.

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Im, Na Ri, Hae Soo Kim, Ji Hoon Ha, Geun Young Noh, and Soo Nam Park. "Antioxidant and Tyrosinase Inhibitory Activities of Dicaffeoylquinic Acid Derivatives Isolated from Gnaphalium Affine D. DON." Applied Chemistry for Engineering 26, no. 4 (August 10, 2015): 470–76. http://dx.doi.org/10.14478/ace.2015.1058.

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38

Helilusiatiningsih, Nunuk, and Edy Soenyoto Soenyoto. "ANALISA SENYAWA BIOAKTIF ANTIOKSIDAN DAN ZAT GIZI TERHADAP BUAH TERUNG POKAK (Solanum torvum) SEBAGAI BAHAN PANGAN FUNGSIONAL." BUANA SAINS 20, no. 1 (June 30, 2020): 7–19. http://dx.doi.org/10.33366/bs.v20i1.1892.

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Solanum torvum has potential as a functional food ingredient because it contains bioactive antioxidant compounds which are quite high and are proven as herbal medicines in China and are a popular food in Florida, Alabama, West India, Malaysia, Thailand, Mexico, Central America, South America, Brazil. The study aims to analyze the components of bioactive antioxidant compounds and nutrients in qualitative and quantitative methods and functional groups in fresh Solanum torvum. The research method used phytochemical screening, quantitative tests, chemical identification with LCMS, FTIR, AAS. The results of phytochemical screening studies, the Solanum torvum contains few alkaloids, while it contains a great number of saponins, steroids, glycosides. The quantitative test showed that the fruit contains 36.31 mg /g phenol, 0.62 mg/g tannin content, 2.76 mg/g flavonoid content and antioxidant activity (% DPPH inhibition) of 84.55%, 82.77% water content, 1.63% ash content, 2.73% fat content, 9.78% protein, 3.69% carbohydrates, 3.77% vitamin C, 0.97% phosphorus, 0.13% potassium, Ca 36.64 ppm, Mg 79.1 ppm, Fe 2.34 ppm. Chemical tests with LCMS contain 13 types of components namely (1) chlorogenic acid, (2) 4-O-caffeoylquinic, (3) 3-O-caffeoylquinic, (4) 4-O-caffeoylquinic, (5) 3-O-feruloylquinic acid, (6) 5-O-feruloylquinic acid, (7) 3-O-dicaffeoylquinic acid, (8) 4-O-dicaffeoylquinic acid, (9) 3-5-O-dicaffeoylquinic acid, (10) 3-O -feruloylquinic acid, (11) 5-O-feruloquinic acid, (12) putative dicaffeoylquiniacid, (13) putativedicaffeoylquinic acid. The functional groups of Solanum torvum have seven types namely phenol (OH), Alkane (C-H), Alkene (C = C), aromatic ring, Nitro (NO2), Amine and Amide (C-N), Alcohol (C-O). Thus, fresh Solanum torvum contains potential antioxidant compounds and nutrients that function for health and functional food.

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39

Bäumer, Dietrich, and Hans Georg Ruppel. "Phenolic Constituents of Galactites tomentosa (Asteraceae)." Zeitschrift für Naturforschung C 51, no. 9-10 (October 1, 1996): 623–26. http://dx.doi.org/10.1515/znc-1996-9-1003.

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The Asteracea Galactites tomentosa. known as a plant causing allergic contact reactions, was investigated for new constituents in leaves and stems. Chlorogenic acid and 3,5-dicaffeoylquinic acid could be detected by HPLC in tissues and trichome preparations as well

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40

Kłeczek, Natalia, Janusz Malarz, Barbara Gierlikowska, Anna K. Kiss, and Anna Stojakowska. "Constituents of Xerolekia speciosissima (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate." Molecules 25, no. 21 (October 23, 2020): 4913. http://dx.doi.org/10.3390/molecules25214913.

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Xerolekia speciosissima (L.) Anderb., a rare plant from the north of Italy, is a member of the Inuleae-Inulinae subtribe of the Asteraceae. Despite its close taxonomic relationship with many species possessing medicinal properties, the chemical composition of the plant has remained unknown until now. A hydroalcoholic extract from the aerial parts of X. speciosissima was analyzed by HPLC-DAD-MSn, revealing the presence of caffeic acid derivatives and flavonoids. In all, 19 compounds, including commonly found chlorogenic acids and less frequently occurring butyryl and methylbutyryl conjugates of dicaffeoylquinic and tricaffeoylhexaric acids, plus two flavonoids, were tentatively identified. Chromatographic separation of a hydroalcoholic extract from the capitula of the plant led to the isolation of (+)-dehydrodiconiferyl alcohol 4-O-β-glucopyranoside, quercimeritrin, astragalin, isoquercitrin, 6-hydroxykaempferol-7-O-β-glucoside, quercetagitrin, methyl caffeate, caffeic acid, protocatechuic acid, chlorogenic acid and 1,5-dicaffeoylquinic acid. Composition of a nonpolar extract from the aerial parts of the plant was analyzed by chromatographic methods supported with 1H-NMR spectroscopy. The analysis revealed the presence of loliolide, reynosin, samtamarine, 2,3-dihydroaromaticin, 2-deoxy-4-epi-pulchellin and thymol derivatives as terpenoid constituents of the plant. One of the latter compounds—7,10-diisobutyryloxy-8,9-epoxythymyl isobutyrate—at concentrations 0.5, 1.0 and 2.5 μM, significantly reduced IL-8, IL-1β and CCL2 excretion by LPS-stimulated human neutrophils.

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Chen, Long, and Li. "Evaluation of Antifungal Phenolics from Helianthus tuberosus L. Leaves against Phytophthora capsici Leonian by Chemometric Analysis." Molecules 24, no. 23 (November 25, 2019): 4300. http://dx.doi.org/10.3390/molecules24234300.

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Phytophthora capsici Leonian causes destructive economical losses in pepper production，and a promising source of natural fungicides- Helianthus tuberosus leaves was reported. The antifungal activities of different extracts and compounds from H. tuberosus leaves against the phytopathogen, P. capsici Leonian, were examined by chemometric analysis, including HPLC-MS/MS and multivariate data analyses. Principal component analysis and orthogonal partial least squares-discriminate analysis were applied to examine the four groups of H. tuberosus leaves samples, including crude extracts obtained by different methods, including refluxing, macerating, and refluxing under vacuum; four fractions, namely, petroleum ether（PE）, chloroform (Chl), ethyl acetate（EA）, and n-butanol (NB) fractions; the samples of three H. tuberosus cultivars; and the samples at three growth stages of cultivar Nan Yu. The phenolics contents were categorized based on 3,5-Dicaffeoylquinic acid (3,5-DiCQA), 1,5-Dicaffeoylquinic acid (1,5-DiCQA), 3-O-Caffeoylquinic acid (3-CQA), and 4,5-Dicaffeoylquinic acid (4,5-DiCQA), which were predominant in all the samples. Antifungal activity assay revealed that Chl and NB fractions were more active against P. capsici Leonian with lower IC50(half of maximal inhibitory concentration) values, whereas partial least squares-discriminate analysis suggested caffeoylquinic acid isomer(4-CQA), methyl-quercetin glycoside(MQG), and caffeic acid(CA) might be the main active components in H. tuberosus leaves against P. capsici Leonian. Furthermore, microscopic evaluation demonstrated structural deformities in P. capsici Leonian treated with Chl and NB fractions, indicating the antifungal effects of H. tuberosus leaves. These results imply that H. tuberosus leaves with a high concentration of phenolics might be a promising source of natural fungicides.

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Chen, Yu-Jie, Guo-Yong Xie, Guang-Kai Xu, Yi-Qun Dai, Lu Shi, and Min-Jian Qin. "Chemical Constituents of Pyrrosia calvata." Natural Product Communications 10, no. 7 (July 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000714.

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A novel flavanone glycoside, 3′,5′,5,7-tetrahydroxy-6- C- β-D-glucopyranosyl-flavanone (1), along with 16 known compounds, ( R/ S)-eriodictyol-8- C- β-D-glucopyranoside (2), quercetin-3- O- α-D-rhamnosyl (1′”→3′”)- β-D-glucopyranoside (3), hemipholin (4), 4 β-carboxymethyl-(-)-epicatechin methyl ester (5), kaempferol (6), quercetin (7), mangiferin (8), chlorogenic acid (9), 1,5- O-dicaffeoylquinic acid (10), 3,5- O-dicaffeoylquinic acid (11), 3- O-caffeoylquinic acid methyl ester (12), 1- O-caffeoyl glycoside (13), 4- O- β-D-glucopyranosyl-caffeic acid (14), 3′- O-methyleplcatechin-7- O- β-D-glucopyranoside (15), hop-22(29)-en-30-ol (16) and diploptene (17), were isolated from the whole plant of Pyrrosia calvata (Backer) Ching. Among them, compounds 2, 3, 4, 10, 11, 13 and 14 were isolated from the family Polypodiaceae for the first time, and compound 5 has not been recorded previously from the genus Pyrrosia.

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Um, Byung H., Merve Polat, Annelise Lobstein, Bernard Weniger, Raul Aragón, Lieve Declercq, and Robert Anton. "A new dicaffeoylquinic acid butyl ester from Isertia pittieri." Fitoterapia 73, no. 6 (October 2002): 550–52. http://dx.doi.org/10.1016/s0367-326x(02)00181-8.

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44

Wald, Burkard, Victor Wray, Rudolf Galensa, and Karl Herrmann. "Malonated flavonol glycosides and 3,5-dicaffeoylquinic acid from pears." Phytochemistry 28, no. 2 (January 1989): 663–64. http://dx.doi.org/10.1016/0031-9422(89)80083-4.

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45

Lee, Sunny Chung, Jongmin Ahn, Jina Kim, Joo-Yeon Lee, Juhae Kim, Md Salah Uddin, Sang Woo Lee, and Choon Young Kim. "The Antioxidant and Anti-Inflammatory Properties of Merremia umbellata Extract." Antioxidants 12, no. 12 (November 23, 2023): 2037. http://dx.doi.org/10.3390/antiox12122037.

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Merremia umbellata Hallier f. (MU) has been used as an anti-inflammatory agent to treat burns and scales. However, the potential anti-inflammatory mechanisms of action of this plant have not been elucidated. This study aimed to assess the antioxidant and anti-inflammatory effects of the leaf and shoot of MU grown in Bangladesh. The MU extract exhibited antioxidant activities as demonstrated by DPPH and ABTS free-radical-scavenging activities and the total polyphenol and total flavonoid contents. MU extract significantly reduced the lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW264.7 macrophage. Accordingly, the gene levels of inducible NO synthase and cyclooxygenase-2 were suppressed. The MU extract alleviated the LPS-induced expression of TLR4, NF-κB, and inflammatory cytokines (TNF-α, IL-6, and IL-1β). The constituents of a MU extract were tentatively identified using UHPLC-PDA-QTOF/MS techniques. The main compounds were identified as 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, quercitrin, and 4,5-dicaffeoylquinic acid. Molecular docking analysis revealed that these compounds interact with TLR4 protein, with quercitrin showing the highest binding affinity among them. Overall, our findings demonstrate the antioxidant and in vitro anti-inflammatory activities of MU and its potential compounds to target the TLR4-NF-κB signaling pathway. These findings are potentially used to further explore promising natural food ingredients that are effective in regulating inflammation.

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Santos, Michel David dos, Guanjie Chen, Maria Camila Almeida, Denis Melo Soares, Glória Emília Petto de Souza, Norberto Peporine Lopes, and R. Clark Lantz. "Effects of Caffeoylquinic Acid Derivatives and C-Flavonoid from Lychnophora ericoides on in vitro Inflammatory Mediator Production." Natural Product Communications 5, no. 5 (May 2010): 1934578X1000500. http://dx.doi.org/10.1177/1934578x1000500512.

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In this study we aimed at evaluating the effect of the major polar constituents of the medicinal plant Lychnophora ericoides on the production of inflammatory mediators produced by LPS-stimulated U-937 cells. The 6,8-di- C-β-glucosylapigenin (vicenin-2) presented no effect on tumor necrosis factor (TNF)-α production, but inhibited, in a dose-dependent manner, the production of prostaglandin (PG) E2 without altering the expression of cyclooxygenase (COX) -2 protein. 3,5-Dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid, at lower concentrations, had small but significant effects on reducing PGE2 levels; at higher doses these compounds stimulated PGE2 and also TNF-α production by the cells. All the caffeoylquinic acid derivatives, in a dose-dependent fashion, were able to inhibit monocyte chemoattractant protein-3 synthesis/release, with 4,5-DCQ being the most potent at the highest tested concentration. These results add important information on the effects of plant natural polyphenols, namely vicenin-2 and caffeoylquinic acid derivatives, on the production of inflammatory mediators by cultured cells.

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Strzępek-Gomółka, Marcelina, Katarzyna Gaweł-Bęben, Apostolis Angelis, Beata Antosiewicz, Zuriyadda Sakipova, Kaldanay Kozhanova, Kazimierz Głowniak, and Wirginia Kukula-Koch. "Identification of Mushroom and Murine Tyrosinase Inhibitors from Achillea biebersteinii Afan. Extract." Molecules 26, no. 4 (February 11, 2021): 964. http://dx.doi.org/10.3390/molecules26040964.

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Growing scientific evidence indicates that Achillea biebersteinii is a valuable source of active ingredients with potential cosmetic applications. However, the data on its composition and pharmacological properties are still insufficient. This study aims to optimize the extraction procedure of the plant material, evaluate its phytochemical composition, and compare anti-tyrosinase potential of A. biebersteinii extracts obtained by various methods. In order to identify compounds responsible for the tyrosinase inhibitory activity of A. biebersteinii, the most active anti-tyrosinase extract was fractionated by column chromatography. The fractions were examined for their skin lightening potential by mushroom and murine tyrosinase inhibitory assays and melanin release assay. HPLC-ESI-Q-TOF-MS/MS analysis of the total extract revealed the presence of several phenolic acids, flavonoids, flavonoid glucosides, and carboxylic acid. Among them, fraxetin-8-O-glucoside, quercetin-O-glucopyranose, schaftoside/isoschaftoside, gmelinin B, 1,3-dicaffeoylquinic acid (1,3-DCQA), and ferulic acid were found in the fractions with the highest skin lightening potential. Based on obtained qualitative and quantitative analysis of the fractions, it was assumed that the caffeoylquinic acid derivatives and dicaffeoylquinic acid derivatives are more likely responsible for mushroom tyrosinase inhibitory activity of A. biebersteinii extracts and fractions. Ferulic acid was proposed as the most active murine tyrosinase inhibitor, responsible also for the reduced melanin release from B16F10 murine melanoma cells.

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Sirichaiwetchakoon, Kittipot, Gordon Matthew Lowe, and Griangsak Eumkeb. "The Free Radical Scavenging and Anti-Isolated Human LDL Oxidation Activities of Pluchea indica (L.) Less. Tea Compared to Green Tea (Camellia sinensis)." BioMed Research International 2020 (September 25, 2020): 1–12. http://dx.doi.org/10.1155/2020/4183643.

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Tea is one of the most popular beverages in the world. Camellia sinensis tea (CST) or green tea is widely regarded as a potent antioxidant. In Thailand, Pluchea indica (L.) Less. tea (PIT) has been commercially available as a health-promoting drink. This study focused on free radical scavenging activities of PIT, and its ability to protect isolated human low-density lipoproteins (LDL) from oxidation by chemical agents. A preliminary study to investigate the antioxidant nature of PIT was undertaken. These included common antioxidant assays involving 2,2-Diphenyl-1-picrylhydrazyl (DPPH), 2,2-azinobis-(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS), hypochlorous acid (HOCl), and its potential to scavenge peroxynitrite. In separated experiments, isolated human LDL was challenged with either 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH), copper (Cu2+), or 3-Morpholinosydnonimine hydrochloride (SIN-1) to induce LDL oxidation. PIT exhibited antioxidant activity in all test systems and performed significantly better than CST in both DPPH (P<0.05; IC50PIT=245.85±15.83 and CST=315.41±24.18 μg/ml) and peroxynitrite scavenging assays. PIT at 75 μg/ml almost fully prevented the peroxynitrite over a 5 h period. Moreover, it displayed similar properties to CST during the antioxidation of isolated human LDL using AAPH, Cu2+, SIN-1, and hypochlorous acid scavenging assays. However, it revealed a significantly lower ABTS scavenging activity than CST (P<0.05; IC50PIT=30.47±2.20 and CST=21.59±0.67 μg/ml). The main constituents of the PIT were identified using LC-MS/MS. It contained 4-O-caffeoylquinic acid (4-CQ), 5-O-caffeoylquinic acid (5-CQ), 3,4-O-dicaffeoylquinic acid (3,4-CQ), 3,5-O-dicaffeoylquinic acid (3,5-CQ), and 4,5-O-dicaffeoylquinic acid (4,5-CQ). In conclusion, caffeoyl derivatives in PIT could play an important role in potent antioxidant properties. So, it may be further developed to be antioxidant beverages for preventing atherosclerosis and cardiovascular diseases associated with oxidative stress.

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Liu, Yujin, Minhao Xie, Peng Wan, Guijie Chen, Chunxu Chen, Dan Chen, Shijie Yu, Xiaoxiong Zeng, and Yi Sun. "Purification, characterization and molecular cloning of a dicaffeoylquinic acid-hydrolyzing esterase from human-derived Lactobacillus fermentum LF-12." Food & Function 11, no. 4 (2020): 3235–44. http://dx.doi.org/10.1039/d0fo00029a.

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Jing-Lei, Xiao, Zhang Yan-Xin, Jia Cheng-Guo, Zhang Ming-Zhe, Chen Wei, Zhang Yu-Bin, Li Bin, et al. "Bioactivity of allelochemicals isolated from the roots of Echinacea purpurea L. Moench on Amaranthus viridis L., Portulaca oleracea L. and Microcystis aeruginosa." Allelopathy Journal 52, no. 1 (January 2021): 119–30. http://dx.doi.org/10.26651/allelo.j/2021-52-1-1311.

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Based on the bioassay-guided strategy, we isolated 6-six allelochemicals [cichoric acid (I), 1,3-dicaffeoylquinic acid (II), 4,5-dicaffeoylquinic acid (III), chlorogenic acid (IV), 1-hydroxy-2-phthoic acid (V), echinacoside (VI)] from the roots of Echinacea purpurea (L.) Moench. Their structures were identified by nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS) spectroscopic data. The bioassays studies included allelopathic and algicidal activities to test the effects of extracts and isolated fractions against the test weeds (Amaranthus viridis L., Portulaca oleracea L. and Microcystis aeruginosa Kutzing). At 100 µg/mL, compound (II) inhibited the shoot length and germination of A. viridis and P. oleracea weeds with the germination RI of -0.95±0.04 and -0.95±0.02, respectively. Furthermore, compound (III) showed the strongest inhibition of root length of P. oleracea L. We also found that compounds I-VI have algicidal activity. The compound (I) at low inoculum (5.0×102 cells mL-1) and high inoculum (1.0×104 cells mL-1), showed the highest algicidal activity of 78 % and 87.67 % 6 h after the treatment at 5 µg mL-1 respectively.

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