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Journal articles on the topic 'Flavanol derivatives'

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Author: Grafiati
Published: 10 December 2022
Last updated: 28 January 2023

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1

Gómez-Juaristi, Miren, Beatriz Sarria, Sara Martínez-López, Laura Bravo Clemente, and Raquel Mateos. "Flavanol Bioavailability in Two Cocoa Products with Different Phenolic Content. A Comparative Study in Humans." Nutrients 11, no. 7 (June 26, 2019): 1441. http://dx.doi.org/10.3390/nu11071441.

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Cocoa has beneficial health effects partly due to its high flavanol content. This study was aimed at assessing the absorption and metabolism of polyphenols in two soluble cocoa products: a conventional (CC) and a flavanol-rich product (CC-PP). A crossover, randomized, blind study was performed in 13 healthy men and women. On two different days, after an overnight fast, volunteers consumed one serving of CC (15 g) or CC-PP (25 g) in 200 mL of semi-skimmed milk containing 19.80 mg and 68.25 mg of flavanols, respectively. Blood and urine samples were taken, before and after CC and CC-PP consumption, and analyzed by high-performance liquid chromatography coupled to electrospray ionisation and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QToF-MS). Up to 10 and 30 metabolites were identified in plasma and urine, respectively. Phase II derivatives of epicatechin were identified with kinetics compatible with small intestine absorption, although the most abundant groups of metabolites were phase II derivatives of phenyl-γ-valerolactone and phenylvaleric acid, formed at colonic level. 5-(4′-Hydroxyphenyl)-γ-valerolactone-sulfate could be a sensitive biomarker of cocoa flavanol intake. CC and CC-PP flavanols showed a dose-dependent absorption with a recovery of 35%. In conclusion, cocoa flavanols are moderately bioavailable and extensively metabolized, mainly by the colonic microbiota.
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2

Fan, Peihong, Hongxiang Lou, Wentao Yu, Dongmei Ren, Bin Ma, and Mei Ji. "Novel flavanol derivatives from grape seeds." Tetrahedron Letters 45, no. 15 (April 2004): 3163–66. http://dx.doi.org/10.1016/j.tetlet.2004.02.054.

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3

Yang, Minghui, Le Cai, Xiaojing Shen, Mian Zhao, Tianpeng Yin, and Zhongtao Ding. "Two Unusual Flavanol Derivatives from Brainea insignis." Chinese Journal of Chemistry 30, no. 6 (June 2012): 1323–26. http://dx.doi.org/10.1002/cjoc.201200158.

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4

Федосеева (Fedoseeva), Людмила (Ljudmila) Михайловна (Mihajlovna), and Георгий (Georgij) Родионович (Rodionovich) Кутателадзе (Kutateladze). "STUDY OF SOME PHENOLIC COMPOUNDS OF THE COMMON SORREL AERAL PART, GROWING IN THE AL-TAI TERRITORY." chemistry of plant raw material, no. 4 (April 18, 2017): 91–96. http://dx.doi.org/10.14258/jcprm.2017041861.

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Common sorrel (Rumex acetosa L.), Polygonaceae family, two-year herbaceous plant, contains a complex of biologically active compounds, based on phenolic compounds (flavonoids, coumarins, anthracene derivatives, tannins). Since ancient times it has been used in folk medicine as an anti-inflammatory, hemostatic, astringent. The purpose of this work is to study the composition of phenolic compounds of the aerial part of common sorrel, which grows on the territory of the Altai Territory. To achieve this goal, it is necessary to solve the following tasks: performe of qualitative reactions on phenolic compounds different groups, separation and identification of phenolic compounds by high-performance liquid chromatography.The results of qualitative reactions allow to suggest the presence of flavonoids flavone and flavanol groups, anthracene derivatives of the chrysacin group, coumarins and condensed tannins in aerial part.High-performance liquid chromatography of common sorrel aerial part ethanol extract (extrctant – 70% ethanol) were used to identify the flavonoids of the flavanol group: kaempferol and quercetin derivatives, anthracene derivatives of the chrysacin group.The studies are aimed at studying the possibility of using the aeral part of common sorrel in medicine. Based on the conducted studies, the development of normative documentation for medicinal plant raw materials is being carried out.
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5

Mottaghipisheh, Javad, and Marcello Iriti. "Sephadex® LH-20, Isolation, and Purification of Flavonoids from Plant Species: A Comprehensive Review." Molecules 25, no. 18 (September 10, 2020): 4146. http://dx.doi.org/10.3390/molecules25184146.

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Flavonoids are considered one of the most diverse phenolic compounds possessing several valuable health benefits. The present study aimed at gathering all correlated reports, in which Sephadex® LH-20 (SLH) has been utilized as the final step to isolate or purify of flavonoid derivatives among all plant families. Overall, 189 flavonoids have been documented, while the majority were identified from the Asteraceae, Moraceae, and Poaceae families. Application of SLH has led to isolate 79 flavonols, 63 flavones, and 18 flavanones. Homoisoflavanoids, and proanthocyanidins have only been isolated from the Asparagaceae and Lauraceae families, respectively, while the Asteraceae was the richest in flavones possessing 22 derivatives. Six flavones, four flavonols, three homoisoflavonoids, one flavanone, a flavanol, and an isoflavanol have been isolated as the new secondary metabolites. This technique has been able to isolate quercetin from 19 plant species, along with its 31 derivatives. Pure methanol and in combination with water, chloroform, and dichloromethane have generally been used as eluents. This comprehensive review provides significant information regarding to remarkably use of SLH in isolation and purification of flavonoids from all the plant families; thus, it might be considered an appreciable guideline for further phytochemical investigation of these compounds.
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6

Vidal-Casanella, Oscar, Oscar Nuñez, and Javier Saurina. "Liquid Chromatographic Fingerprints for the Characterization of Flavanol-Rich Nutraceuticals Based on 4-Dimethylaminocinnamaldehyde Precolumn Derivatization." Scientia Pharmaceutica 89, no. 2 (May 6, 2021): 18. http://dx.doi.org/10.3390/scipharm89020018.

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Flavanols consist of a great family of bioactive molecules displaying a wide range of health-promoting attributes for humans, including antioxidant, antimicrobial or anti-inflammatory effects. As a result, botanical species rich in this type of compound are often used to develop nutraceutical products or dietary supplements with recognized healthy attributes. This paper aims at characterizing nutraceutical products using liquid chromatographic fingerprints related to flavanol composition. Catechins and their oligomers were exploited to characterize and authenticate various commercial products prepared with extracts of red berries and medicinal plants. These compounds resulted in interesting descriptors of some fruits and vegetables, thus providing an additional perspective for the study of nutraceuticals. For such a purpose, a new method based on liquid chromatography with UV/Vis detection (HPLC–UV/Vis) with precolumn derivatization with 4-dimethylaminocinnamaldehyde was developed. Results indicated that the separation of flavanols was very complex due to the degradation of procyanidin derivatives. The resulting data sets were analyzed using chemometric methods such as principal component analysis and partial least square–discriminant analysis. Despite the complexity of chromatographic fingerprints, nutraceutical samples could be discriminated according to their main ingredients. In general, catechin and epicatechin were the most abundant compounds in the different samples, and procyanidin A2 was highly specific to cranberry.
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7

SÁNCHEZ-ILÁRDUYA, M. B., C. SÁNCHEZ-FERNÁNDEZ, M. VILORIA-BERNAL, D. M. LÓPEZ-MÁRQUEZ, L. A. BERRUETA, B. GALLO, and F. VICENTE. "Mass spectrometry fragmentation pattern of coloured flavanol-anthocyanin and anthocyanin-flavanol derivatives in aged red wines of Rioja." Australian Journal of Grape and Wine Research 18, no. 2 (May 25, 2012): 203–14. http://dx.doi.org/10.1111/j.1755-0238.2012.00190.x.

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8

Li, Dong-Li, Xiao-Ming Li, Ze-Yu Peng, and Bin-Gui Wang. "Flavanol Derivatives from Rhizophora stylosa and Their DPPH Radical Scavenging Activity." Molecules 12, no. 5 (May 26, 2007): 1163–69. http://dx.doi.org/10.3390/12051163.

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9

Aldrich, Leslie, Qiwen Gao, Lianyan Xu, Vincent Parise, and Yash Mehta. "Enantioselective Synthesis of 4-Amino-3-hydroxybenzopyran Flavanol Derivatives from Chalcones." Synthesis 50, no. 24 (November 21, 2018): 4796–808. http://dx.doi.org/10.1055/s-0037-161114.

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A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.
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10

Nawrot-Hadzik, Izabela, Adam Matkowski, Jakub Hadzik, Barbara Dobrowolska-Czopor, Cyprian Olchowy, Marzena Dominiak, and Paweł Kubasiewicz-Ross. "Proanthocyanidins and Flavan-3-Ols in the Prevention and Treatment of Periodontitis—Antibacterial Effects." Nutrients 13, no. 1 (January 7, 2021): 165. http://dx.doi.org/10.3390/nu13010165.

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Flavan-3-ols and their oligomeric forms called proanthocyanidins are polyphenolic compounds occurring in several foodstuffs and in many medicinal herbs. Their consumption is associated with numerous health benefits. They exhibit antioxidant, anti-inflammatory, cytoprotective, as well as antimicrobial activity. The latter property is important in the prevention and treatment of periodontal diseases. Periodontitis is a multifactorial polymicrobial infection characterized by a destructive inflammatory process affecting the periodontium. Using non-toxic and efficient natural products such as flavanol derivatives can significantly contribute to alleviating periodontitis symptoms and preventing the disease’s progress. Therefore, a comprehensive systematic review of proanthocyanidins and flavan-3-ols in the prevention and treatment of periodontitis was performed. The present paper reviews the direct antibacterial effects of these compounds against periodontic pathogens. The immunomodulatory effects, including animal and clinical studies, are included in a separate, parallel article. There is significant evidence supporting the importance of the antibacterial action exerted by proanthocyanidins from edible fruits, tea, and medicinal herbs in the inhibition of periodontitis-causing pathogens.
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11

Nawrot-Hadzik, Izabela, Adam Matkowski, Jakub Hadzik, Barbara Dobrowolska-Czopor, Cyprian Olchowy, Marzena Dominiak, and Paweł Kubasiewicz-Ross. "Proanthocyanidins and Flavan-3-Ols in the Prevention and Treatment of Periodontitis—Antibacterial Effects." Nutrients 13, no. 1 (January 7, 2021): 165. http://dx.doi.org/10.3390/nu13010165.

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Flavan-3-ols and their oligomeric forms called proanthocyanidins are polyphenolic compounds occurring in several foodstuffs and in many medicinal herbs. Their consumption is associated with numerous health benefits. They exhibit antioxidant, anti-inflammatory, cytoprotective, as well as antimicrobial activity. The latter property is important in the prevention and treatment of periodontal diseases. Periodontitis is a multifactorial polymicrobial infection characterized by a destructive inflammatory process affecting the periodontium. Using non-toxic and efficient natural products such as flavanol derivatives can significantly contribute to alleviating periodontitis symptoms and preventing the disease’s progress. Therefore, a comprehensive systematic review of proanthocyanidins and flavan-3-ols in the prevention and treatment of periodontitis was performed. The present paper reviews the direct antibacterial effects of these compounds against periodontic pathogens. The immunomodulatory effects, including animal and clinical studies, are included in a separate, parallel article. There is significant evidence supporting the importance of the antibacterial action exerted by proanthocyanidins from edible fruits, tea, and medicinal herbs in the inhibition of periodontitis-causing pathogens.
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12

Torres, J. L., and R. Bobet. "New Flavanol Derivatives from Grape (Vitis vinifera) Byproducts. Antioxidant Aminoethylthio−Flavan-3-ol Conjugates from a Polymeric Waste Fraction Used as a Source of Flavanols." Journal of Agricultural and Food Chemistry 49, no. 10 (October 2001): 4627–34. http://dx.doi.org/10.1021/jf010368v.

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13

Li, Feng, Suresh Awale, Yasuhiro Tezuka, and Shigetoshi Kadota. "Cytotoxicity of Constituents from Mexican Propolis against a Panel of Six Different Cancer Cell Lines." Natural Product Communications 5, no. 10 (October 2010): 1934578X1000501. http://dx.doi.org/10.1177/1934578x1000501018.

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The cytotoxicity of 39 compounds, including eighteen flavonoids (flavanones, 1–10; flavones, 11–17; flavanol, 18), sixteen phenolic acid derivatives (aromatic acids, 19–24; aldehyde, 25; esters, 26–34) and five glycerides (35–39), isolated from Mexican propolis, were evaluated against a panel of six different cancer cell lines; murine colon 26-L5 carcinoma, murine B16-BL6 melanoma, murine Lewis lung carcinoma, human lung A549 adenocarcinoma, human cervix HeLa adenocarcinoma and human HT-1080 fibrosarcoma. A phenylpropanoid-substituted flavanol, (2 R,3 S)-8-[4-phenylprop-2-en-1-one]-4’,7-dihydroxy-3’,5-dimethoxyflavan-3-ol (18), showed the most potent cytotoxicity against A549 cells (IC50, 6.2 μM) and HT-1080 cells (IC50, 3.9 μM), stronger than those of the clinically used anticancer drug, 5-fluorouracil (IC50, 7.5 μM and 5.4 μM, respectively). Based on the observed results, the structure–activity relationships are discussed.
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14

Huang, Deng-Ming, Hui-Jing Li, Yan Zhao, and Yan-Chao Wu. "Synthesis of Bisflavanol-Type Natural Products and Their Analogues­ via Self-Coupling of C8-Methylol Catechin Derivatives." Synthesis 51, no. 16 (April 24, 2019): 3127–41. http://dx.doi.org/10.1055/s-0037-1610707.

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A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and oolonghomobisflavan A. The novel self-coupling mechanism sheds new light on the classical Friedel–Crafts alkylation mechanism in acid-catalyzed catechin–formaldehyde condensation.
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15

Prat-García, Samanta, Joana Oliveira, Maria del Alamo-Sanza, Victor de Freitas, Ignacio Nevares, and Nuno Mateus. "Characterization of Anthocyanins and Anthocyanin-Derivatives in Red Wines during Ageing in Custom Oxygenation Oak Wood Barrels." Molecules 26, no. 1 (December 25, 2020): 64. http://dx.doi.org/10.3390/molecules26010064.

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The ageing of wines in oak barrels is a key stage in the production of high-quality red wines, with the type of oak chosen and the amount of oxygen received by the wine being the determining factors of the process. This work analyses the effect of ageing the same red wine in barrels with different oxygenation rates for one year (OTR), specifically the effect on the evolution of anthocyanins, their derivatives and the appearance of new pigments according to the oxygen dosage in barrels. Results show that wines aged in High-Wood-OTR barrels have a large quantity of monomeric anthocyanins and wine aged in Low-Wood-OTR barrels presents a major intensity of colour. Moreover, using LC-MS analysis, it was possible to detect and identify different families of anthocyanin derivatives, including the tentative identification of two new aldehyde-flavanol-methylpyranoanthocyanin pigments.
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16

Río Segade, Susana, Ignacio Orriols, Vincenzo Gerbi, and Luca Rolle. "Phenolic characterization of thirteen red grape cultivars from Galicia by anthocyanin profile and flavanol composition." OENO One 43, no. 4 (December 31, 2009): 189. http://dx.doi.org/10.20870/oeno-one.2009.43.4.791.

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<p><strong>Aims</strong>: Phenolic compounds, extractable from grape skins and seeds, have a notable influence on the quality of red wines. Therefore, in this work the phenolic composition of 13 red grape cultivars, grown in one of the most traditional Spanish vine zones, was studied in order to identify significant varietal differences.</p><p><strong>Methods and results</strong>: Anthocyanin concentration and profile, total proanthocyanidin and flavanol contents in berry skins and seeds were determined by spectrophotometric and HPLC methods. The highest concentrations of total anthocyanins was found in the Loureira Tinta, Sousón and Ferrol varieties, while Ferrol was rich in proanthocyanidins in berry skin and Caíño Bravo was rich in proanthocyanidins and flavanols in berry seeds. Malvidin-3-monoglucoside was usually the major anthocyanin. Nevertheless, the anthocyanin profile was characterized mainly of di-substituted molecules for Albarello, Brancellao and Caíño da Terra grapes. Ferrol, Loureira Tinta and Sousón grapes showed the highest values of primitive anthocyanins (delphinidin and petunidin derivatives).</p><p><strong>Conclusion</strong>: Many differences in the phenolic composition of the cultivars studied were found. The results of the phenolic characterization can be utilized in winery in order to apply the most appropriate maceration and winemaking techniques to the processed grapes.</p><p><strong>Significance and impact of study</strong>: Knowledge of the biodiversity of the grape varieties of Galicia (North-West Spain) is still scarce. This study, on phenolic composition, provides oenological information that can be useful to improve the quality of the wines produced.</p>
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17

Orabi, Mohamed A. A., Omaish Salman Alqahtani, Bandar A. Alyami, Ahmed Abdullah Al Awadh, El-Shaymaa Abdel-Sattar, Katsuyoshi Matsunami, Dalia I. Hamdan, and Mohamed E. Abouelela. "Human Lung Cancer (A549) Cell Line Cytotoxicity and Anti-Leishmania major Activity of Carissa macrocarpa Leaves: A Study Supported by UPLC-ESI-MS/MS Metabolites Profiling and Molecular Docking." Pharmaceuticals 15, no. 12 (December 14, 2022): 1561. http://dx.doi.org/10.3390/ph15121561.

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Lung cancer and cutaneous leishmaniasis are critical diseases with a relatively higher incidence in developing countries. In this research, the activity of Carissa macrocarpa leaf hydromethanolic extract and its solvent-fractions (n-hexane, EtOAc, n-butanol, and MeOH) against the lung adenocarcinoma cell line (A549) and Leishmania major was investigated. The MeOH fraction exhibited higher cytotoxic activity (IC50 1.57 ± 0.04 μg/mL) than the standard drug, etoposide (IC50 50.8 ± 3.16 μg/mL). The anti-L. major results revealed strong growth inhibitory effects of the EtOAc fraction against L. major promastigotes (IC50 27.52 ± 0.7 μg/mL) and axenic amastigotes (29.33 ± 4.86% growth inhibition at 100 μg/mL), while the butanol fraction exerted moderate activity against promastigotes (IC50 73.17 ± 1.62), as compared with miltefosine against promastigotes (IC50 6.39 ± 0.29 μg/mL) and sodium stibogluconate against axenic amastigotes (IC50 22.45 ± 2.22 μg/mL). A total of 102 compounds were tentatively identified using UPLC-ESI-MS/MS analysis of the total extract and its fractions. The MeOH fraction was found to contain several flavonoids and flavan-3-ol derivatives with known cytotoxic properties, whereas the EtOAc fractions contained triterpene, hydroxycinnamoyl, sterol, and flavanol derivatives with known antileishmanial activity. Molecular docking of various polyphenolics of the MeOH fraction with HDAC6 and PDK3 enzymes demonstrates high binding affinity of the epicatechin 3-O-β-D-glucopyranoside and catechin-7-O-β-D-glucopyranoside toward HDAC6, and procyanidin C2, procyanidin B5 toward PDK3. These results are promising and encourage the pursuit of preclinical research using C. macrocarpa’s MeOH fraction as anti-lung cancer and the EtOAc fraction as an anti-L. major drug candidates.
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18

Luo, Yu, Yuqing Jian, Yingkai Liu, Sai Jiang, Daniyal Muhammad, and Wei Wang. "Flavanols from Nature: A Phytochemistry and Biological Activity Review." Molecules 27, no. 3 (January 22, 2022): 719. http://dx.doi.org/10.3390/molecules27030719.

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Flavanols, a common class of secondary plant metabolites, exhibit several beneficial health properties by acting as antioxidant, anticarcinogen, cardioprotective, anti-microbial, anti-viral, and neuroprotective agents. Furthermore, some flavanols are considered functional ingredients in dairy products. Based on their structural features and health-promoting functions, flavanols have gained the attention of pharmacologists and botanists worldwide. This review collects and summarizes 121 flavanols comprising four categories: flavan-3-ols, flavan-4-ols, isoflavan-4-ols, and flavan-3,4-ols. The research of the various structural features and pharmacological activities of flavanols and their derivatives aims to lay the groundwork for subsequent research and expect to provide mentality and inspiration for the research. The current study provides a starting point for further research and development.
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19

AFIFY, Abd El-Moneim M. R., Emad A. SHALABY, and Hossam Saad EL-BELTAGI. "Antioxidant Activity of Aqueous Extracts of Different Caffeine Products." Notulae Botanicae Horti Agrobotanici Cluj-Napoca 39, no. 2 (November 21, 2011): 117. http://dx.doi.org/10.15835/nbha3926254.

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The antioxidant activity of water extracts (cold and hot) of six caffeine products were carried out. The extracts were screened for total polyphenol contents and antioxidant activity using DPPH, ABTS methods and reducing power method at 50 and 100 μg/ml after 15 min and 30 min using DPPH, ABTS BHA and Caffeine as standard compounds. The results indicated that, the hot water extracts for different caffeine products showed higher antioxidant activity than those of cold extracts and this activity was time and concentration dependent. In addition, the activity was higher against ABTS radical more than DPPH and reducing power methods. Also, there is a positive correlation between the antioxidant and reducing compounds presented in water extracts of different caffeine products. The results of HPLC showed that fresh tea leaves are rich in flavanol monomers known as catechins. The most abundant catechin derivatives in green tea are EGC, EGCG and GC. On the other hand EGCG and GC are major catechin derivative in different caffeine product except El-Fakher tea and Cacao. Generally, these beverages had high antioxidant capacities and total phenolic contents, and could be important dietary sources of antioxidant phenolic for prevention of diseases caused by oxidative stress.
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20

Sánchez-Ilárduya, María Belén, Cristina Sánchez-Fernández, Sergio Garmón-Lobato, Beatriz Abad-García, Luis Angel Berrueta, Blanca Gallo, and Francisca Vicente. "Detection of non-coloured anthocyanin–flavanol derivatives in Rioja aged red wines by liquid chromatography–mass spectrometry." Talanta 121 (April 2014): 81–88. http://dx.doi.org/10.1016/j.talanta.2013.12.066.

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21

DESRUES, OLIVIER, CHRISTOS FRYGANAS, HONORATA M. ROPIAK, IRENE MUELLER-HARVEY, HEIDI L. ENEMARK, and STIG M. THAMSBORG. "Impact of chemical structure of flavanol monomers and condensed tannins on in vitro anthelmintic activity against bovine nematodes." Parasitology 143, no. 4 (February 18, 2016): 444–54. http://dx.doi.org/10.1017/s0031182015001912.

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SUMMARYPlants containing condensed tannins (CT) may have potential to control gastrointestinal nematodes (GIN) of cattle. The aim was to investigate the anthelmintic activities of four flavan-3-ols, two galloyl derivatives and 14 purified CT fractions, and to define which structural features of CT determine the anti-parasitic effects against the main cattle nematodes. We used in vitro tests targeting L1 larvae (feeding inhibition assay) and adults (motility assay) of Ostertagia ostertagi and Cooperia oncophora. In the larval feeding inhibition assay, O. ostertagi L1 were significantly more susceptible to all CT fractions than C. oncophora L1. The mean degree of polymerization of CT (i.e. average size) was the most important structural parameter: large CT reduced larval feeding more than small CT. The flavan-3-ols of prodelphinidin (PD)-type tannins had a stronger negative influence on parasite activity than the stereochemistry, i.e. cis- vs trans-configurations, or the presence of a gallate group. In contrast, for C. oncophora high reductions in the motility of larvae and adult worms were strongly related with a higher percentage of PDs within the CT fractions while there was no effect of size. Overall, the size and the percentage of PDs within CT seemed to be the most important parameters that influence anti-parasitic activity.
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22

Itnawita, Itnawita, Zamri Adel, Ganis Fia Kartika, Sofia Anita, T. Abu Hanifah, G. A. Guntur, and U. Shyfaa. "Use of the compound (2-(4-chlorophenyl)-3-hydroxy-4H-chromene-4-one) as a ligand complex formation by copper (II)." Current Chemistry Letters 11, no. 4 (2022): 353–58. http://dx.doi.org/10.5267/j.ccl.2022.6.002.

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Flavanol compounds are chalcone derivatives, generally found in hydroxy substituted forms that can act as ligands. Hydroxy-substituted flavonols are found in many plants but in very small amounts. In order to enrich and expand the use of this compound as a ligand, the synthetic methods were carried out through structural variations, one of which was by substitution using chloride and then the compound (2-(4-chlorophenyl)-3-hydroxy-4H-chromene-4-one) was obtained. In this research, the study was conducted using the compound (2-(4-chlorophenyl)-3-hydroxy-4H-chromene-4-one) as a ligand for complex formation with copper (II). From the results of the study, the mole ratio of the ligand with copper (II) metal was 2:1, pH 7.01 with a complex stability time of 15-25 minutes. The complex formed is bright yellow in color and soluble in chloroform. From the characterization of the resulted complex, it was appeared that Cu-flavonol chloride with UV-Vis spectrophotometer showed maximum absorption at wavelengths 273 and 429 indicating the presence of benzoyl and cinnamoyl peaks, with FT-IR showing the wave number 1545cm-1 indicating the presence of Cu=O-Cu bonds and absorption at 682 cm-1 indicating the presence of Cu-O bonds.
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23

Lutfian, Lutfian, Aris Munandar, Rismawan Adi Yunanto, and Ahmad Rizki Nur Hakiki. "Effectiveness of Yoga, Fast of Dawood, Green Tea and Apple Juice as Suppressors of PPAR-γ, C/EBP-α, and SREBP-c for Management of Obesity on Adolescents." Nursing and Health Sciences Journal (NHSJ) 1, no. 3 (December 29, 2021): 223–30. http://dx.doi.org/10.53713/nhs.v1i3.79.

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Obesity is a condition that can increase the risk of some diseases such as reduced brain capacity, dyspnea, skin irritation, hypertension, and diabetes. Proper treatment is needed to overcome the problems of obesity. The objective of this study was to investigate the effectiveness of Yoga, fast of Dawood, Green Tea, and Apple juice to suppressor PPAR-γ gene activity, C / EBPα, and SREBP-c to manage obesity in adolescents. The method used in this study was a literature review from journal publications through the database ScienceDirect, PUBMED, and google scholar, and the criteria were Indonesian and English with a range of publication years 2014-2019. Nine main articles were used as references in this study. These articles proved that yoga therapy could maintain the balance and health of the physical, emotional, and spiritual dimensions, and Fast of Dawood can limit the amount of calorie intake at a particular time. Moreover, by consuming green tea as a source of polyphenol derivatives and apples with high of flavanol, anthocyanidin, dihydrochalcones, and hydroxycinnamic acid could decrease adolescents' body weight. Yoga and Fast of Dawood exercise can reduce adipogenesis and induce reverse cholesterol transport, cellular cholesterol released, reduced pro-inflammatory cytokines dan decreased the incidence of obesity.
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Oktavianawati, Ika, Sattya Arimurti, and Suharjono Suharjono. "The Impacts of Traditional Fermentation Method on the Chemical Characteristics of Arabica Coffee Beans from Bondowoso District, East Java." Journal of Pure and Applied Chemistry Research 9, no. 2 (August 31, 2020): 133–41. http://dx.doi.org/10.21776/ub.jpacr.2020.009.02.526.

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Bondowoso district is the predominant supplier of coffee beans, and also known as Republik Kopi. However, there was still insufficient data about the chemical characteristics of coffee from Bondowoso. This research has main aims to characterize the chemical characteristic of Coffea Arabica L. from Bondowoso, and determine the impact of traditional fermentation on them. Coffee beans were naturally-fermented through soaking in water for less than 12 hours. Unfermented coffee beans were used as a control. Both unfermented and fermented coffee beans were subjected to chemical analysis. Results show that total nitrogen and lipid contents of both fermented and unfermented beans decreased after fermentation into 0.19%±0.03 and 10.03%±0.14, respectively. LCMS analysis of coffee beans revealed that the majority of amino acid contents in fermented beans were higher than that found in unfermented beans, while caffeine and derivatives to be lower in fermented coffee beans than in unfermented beans. One exception for this was 7-methylxanthine, which was found only in fermented beans. Other metabolites, including procyanidines A and B, were found to decrease through fermentation. Interestingly, 3-flavanol was found only in fermented coffee beans. This research results would benefit on improving the quality of coffee through fermentation step.
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Ismiyarto, Ismiyarto, Sabirin Matsjeh, and Chairil Anwar. "Synthesis of Chalcone and Flavanone Compound Using Raw Material of Acetophenone and Benzaldehyde Derivative." Indonesian Journal of Chemistry 1, no. 2 (June 3, 2010): 81–89. http://dx.doi.org/10.22146/ijc.21948.

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Synthesis of flavanoid compounds of chalcone and flavanone groups have been conducted. Flavanoid Is one of the group natural products which is mostly found in plants and have been proved to have physiological activity as drug. In this research, chalcone proup compounds that being synthesized are: chalcone, 3,4-dimethoxychalcone, 2'-hidroxy-3,4-dimethoxychalcone where as compound of flavanone group that being synthesized is 3',4'-dimethoxyflavanone. The synthesis of chalcone group are carried out based on Claisen-Schmidt reaction by using raw material of aromatic aldehydes and aromatic ketones. The synthesis in carried out by stirring at the room temperature using alkali solution as catalyst and ethanol as solvent. The synthesis of 3',4'-dimethoxyflanone is made based on the nucleophilic 1,4 addition of the unsaturated α,β ketone. The synthesis is made by refluxing 2'-hydroxy-3,4-dimethoxychalcone in alkali condition for 12 hours. The identification of flavanoid compound is carried out by using spectroscopic IR, GC-MS and 1H-NMR methods. The result of each synthesis chalcone group are follows: chalcone as yellowish solid with m.p= 50 °C and the yield is 83.39%; 3,4-dimethoxychalcone as yellow solid with m.p= 57°C and the yield is 76.00% ; 2'-hydroxy-3,4-dimethoxychalcone as orange solid with m.p= 90 °C and the yield is 74.29%, for 3',4'-dimethoxyflavanone as pale yellow solid with m.p= 80 °C and the yield is 72.00%.
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Urpi-Sarda, Mireia, Emma Ramiro-Puig, Nasiruddin Khan, Sara Ramos-Romero, Rafael Llorach, Margarida Castell, Susana Gonzalez-Manzano, Celestino Santos-Buelga, and Cristina Andres-Lacueva. "Distribution of epicatechin metabolites in lymphoid tissues and testes of young rats with a cocoa-enriched diet." British Journal of Nutrition 103, no. 10 (January 26, 2010): 1393–97. http://dx.doi.org/10.1017/s0007114509993473.

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An increasing number of scientific studies support that flavanol-rich foods and beverages such as cocoa can promote human health, and are beneficial agents for the prevention of some diseases. Our previous studies showed that long-term cocoa intake enhances the antioxidant status in lymphoid organs and also modulates lymphocyte functionality in healthy young rats. Cocoa polyphenolic antioxidants seem to be the best candidates for those effects. However, data regarding polyphenol metabolites in tissues after a long-term cocoa intake are scarce. In the present study we mainly focus on the uptake and accumulation of epicatechin metabolites in lymphoid organs, including the thymus, spleen and mesenteric lymphoid nodes, as well as in the liver and testes after a diet rich in cocoa. Ten young weaned Wistar rats were fed randomly with a 10 % (w/w) cocoa diet or a control diet for 3 weeks, corresponding to their infancy and youth. Tissues were treated with a solid-phase extraction and analysed by liquid chromatography–tandem MS. The major compounds recovered in these tissues were glucuronide derivatives of epicatechin and methylepicatechin. The highest concentration of these metabolites was found in the thymus, testicles and liver, followed by lymphatic nodes and spleen. The high amount of epicatechin metabolites found in the thymus supports our previous findings showing its high antioxidant capacity compared with other tissues such as the spleen. Moreover, this is the first time that epicatechin metabolites have been found in high concentrations in the testes, confirming other studies that have suggested the testes as an important site of oxidation.
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Tistechok, Stepan, Marc Stierhof, Anna Kachor, Maksym Myronovskyi, Oleksandr Gromyko, and Andriy Luzhetskyy. "Flavacol and Its Novel Derivative 3-β-Hydroxy Flavacol from Streptomyces sp. Pv 4-95 after the Expression of Heterologous AdpA." Microorganisms 10, no. 12 (November 25, 2022): 2335. http://dx.doi.org/10.3390/microorganisms10122335.

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Actinomycetes are one of the main producers of biologically active compounds. However, their capabilities have not been fully evaluated due to the presence of many unexpressed silent clusters; moreover, actinomycetes can probably produce new or previously discovered natural products under certain conditions. Overexpressing the adpA gene into streptomycetes strains can unlock silent biosynthetic gene clusters. Herein, we showed that by applying this approach to Streptomyces sp. Pv 4-95 isolated from Phyllostachys viridiglaucescens rhizosphere soil, two new mass peaks were identified. NMR structure analysis identified these compounds as flavacol and a new 3-β-hydroxy flavacol derivative. We suggest that the presence of heterologous AdpA has no direct effect on the synthesis of flavacol and its derivatives in the Pv 4-95 strain. However, AdpA affects the synthesis of precursors by increasing their quantity, which then condenses into the resulting compounds.
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28

Vargas-Arana, Gabriel, Claudia Merino-Zegarra, Ángel Martín Rodríguez del-Castillo, Cristina Quispe, Ezequiel Viveros-Valdez, and Mario J. Simirgiotis. "Antioxidant, Antiproliferative and Anti-Enzymatic Capacities, Nutritional Analysis and UHPLC-PDA-MS Characterization of Ungurahui Palm Fruits (Oenocarpus bataua Mart) from the Peruvian Amazon." Antioxidants 11, no. 8 (August 18, 2022): 1598. http://dx.doi.org/10.3390/antiox11081598.

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Ungurahui, or Patawa, fruits are a popular fruit and medicinal food used in the Amazon. Here, we have studied nine natural populations of ungurahui from the Peruvian Amazon regarding their nutritional and biological activities, including metal composition, proximal analyses, cytotoxic, antioxidant and cholinesterase inhibition activities. Twenty-four compounds have been detected in these Peruvian natural populations by UHPLC-MS, including nine phenolic acids (peaks 1–6, 8, 9 and 11), four C-glycosyl flavonoids (peaks 12, 16, 17 and 18), two flavonols (peaks 7 and 10), one flavanol (peak 15), three anthocyanins (peaks 13, 14 and 22) and five resveratrol derivatives (peaks 19–21, 23 and 24). Sample 9, Tunaants, showed the highest DPPH clearing capacity regarding the content of Trolox equivalents (2208.79 μmol Trolox/g), but an ORAC test of the sample collected in San Lorenzo showed the highest clearing activity (1222.28 μmol Trolox/g) and the sample collected in Allpahuayo Mishana showed the most powerful ABTS (1803.72 μmol Trolox/g). The sample from Jenaro Herrera was the most powerful in AChe inhibition (IC50 2.05 ± 0.03 μg/mL), followed by the sample from Contamana (IC50 2.43 ± 0.12 μg/mL). In BChE inhibition, the sample from Palestina was the most active (4.42 ± 0.06 μg/mL), followed by samples from Tunaants and San Lorenzo. The differences among bioactivities can be related to the different growing conditions of the populations of ungurahui. The palm tree fruit proved to be a good source of natural antioxidants and dietary fatty acids, and their consumption represents an alternative for the prevention of neurodegenerative or related non-chronic transmittable diseases.
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Mardjan, Muhammad Idham Darussalam, Retno Ambarwati, Sabirin Matsjeh, Tutik Dwi Wahyuningsih, and Winarto Haryadi. "SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE." Indonesian Journal of Chemistry 12, no. 1 (February 14, 2012): 70–76. http://dx.doi.org/10.22146/ijc.21374.

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Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.
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Valkovska, Valda, and Liāna Orola. "Characterization of Pigments from <i>Malus domestica</i> Leaves for Wool Dyeing." Key Engineering Materials 903 (November 10, 2021): 63–68. http://dx.doi.org/10.4028/www.scientific.net/kem.903.63.

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The study will present results of chemical analysis of mass spectrometry, evaluating the content of pigments in M. domestica leaves dyeing solution and in dyed woollen yarn nowadays. Yarn was dyed with fresh leaves of M. domestica tree. Before dyeing the yarn was treated with potassium aluminium sulphate mordant. Dyestuffs from the yarn were extracted in compliance with modified hydrochloric method of hydrolysis. Extracts were analysed by ultra high-performance liquid chromatography coupled with a diode array detector and mass spectrometry (UHPLC-DAD-MS) for identification of the pigments. Phytochemical screening of dyeing solution of the M. domestica leaves showed presence of dihydrochalcones (phloretin, phlorizin), flavan-3-ols (dimeric B type proanthocyanidin, catechin, epicatechin, gallocatehin, epigallocatechin), flavanols (quercetin derivatives: hyperoside, rutin, quercetrin), phenolic acids and other compounds.
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Kobori, Ryo, Syuichi Yakami, Takashi Kawasaki, and Akiko Saito. "Changes in the Polyphenol Content of Red Raspberry Fruits during Ripening." Horticulturae 7, no. 12 (December 10, 2021): 569. http://dx.doi.org/10.3390/horticulturae7120569.

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Berry fruits that contain large amounts of polyphenol compounds are expected to exhibit health and anti-aging effects due to the antioxidant activities of these components. Among the various polyphenols, flavan-3-ol derivatives are known to have a particularly high functionality. In this study, the maturity of red raspberry fruits is classified into eight stages based on the polyphenol content at each stage. Quantification of the various compounds and investigation of the DPPH and ABTS radical scavenging activities were carried out. The total polyphenol content, including that of the flavan-3-ol derivatives, was the highest in immature fruits, gradually decreasing during fruit maturation, during which the radical scavenging activity also decreased. Based on our quantitative results, it was considered that the decrease in the flavan-3-ol derivative content due to fruit ripening was largely related to the increase in the amount of anthocyanin derivatives. Considering that the decreased contents of these compounds were related to the expression levels of polyphenol biosynthetic enzymes, quantification was performed using the semi-quantitative polymerase chain reaction, but the only change observed was the increased expression of the enzyme that synthesizes anthocyanins during maturation. Therefore, it was suggested that it is necessary to inhibit anthocyanin synthesis to increase the contents of highly functional flavan-3-ol derivatives in the mature fruit.
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Šuković, Danijela, Bojana Knežević, Uroš Gašić, Milica Sredojević, Ivanka Ćirić, Slavica Todić, Jelena Mutić, and Živoslav Tešić. "Phenolic Profiles of Leaves, Grapes and Wine of Grapevine Variety Vranac (Vitis vinifera L.) from Montenegro." Foods 9, no. 2 (January 28, 2020): 138. http://dx.doi.org/10.3390/foods9020138.

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Vranac, an old autochthonous red grapevine variety of Montenegro, was first mentioned in a historical document published in the 15th century. As currently the study of indigenous varieties is of particular importance, the subject of this work was detailed characterization of phenolic compounds in the autochthonous grapevine variety Vranac, from the Montenegrin Podgorica subregion. Phenolic profiles of leaves, berries (skin, seeds, and pulp were examined separately) and young monovarietal wine were determined using ultra-high performance liquid chromatography (UHPLC) with linear trap quadrupole (LTQ)—Orbitrap XL mass spectrometry (MS). Total phenolic content (TPC) and radical scavenging activity (RSA) were higher for the grape seeds extracts, followed by extracts of grape skins and pulps. As expected, the total anthocyanin content (TAC) was higher in grape skin than in wine. A total of one hundred twenty nine compounds (forty two phenolic acids and their derivatives, twenty three flavan-3-ols, twenty one flavanols, five stilbenes and thirty eight anthocyanins) were identified in the investigated extracts. To our best knowledge, this is the first report of tentative identification of (epi)catechin 3-O-coumarate in grape seed and chalcan-flavan 3-ol dimers in wine and grape seed.
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Song, Lijun, Jie Zheng, Li Zhang, Shijuan Yan, Wenjie Huang, Jun He, and Pengzhan Liu. "Phytochemical Profiling and Fingerprint Analysis of Chinese Jujube (Ziziphus jujuba Mill.) Leaves of 66 Cultivars from Xinjiang Province." Molecules 24, no. 24 (December 11, 2019): 4528. http://dx.doi.org/10.3390/molecules24244528.

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Foliage of jujube (Ziziphus jujuba Mill.) as a byproduct of agriculture, is a traditional nutraceutical material in China. Previous studies have shown that it is a rich resource of polyphenols. However, information on its complete phenolic profile and the difference between cultivars is still limited. This study investigated and compared phytochemical profiles of leaves of 66 Chinese jujube cultivars. Forty-two compounds, including 22 flavonols, two flavanols, one flavanone, 13 derivatives of phenolic acids, three simple acids, and one unknown hexoside were identified/tentatively identified using high-performance liquid chromatography (HPLC) coupled with high-resolution mass spectrometry. Eight major flavonols were quantified by HPLC coupled with an ultraviolet (UV) detector. The contents of total flavonoids ranged from 2.6–25.1 mg/g dry weight (DW). Differences between cultivars were analyzed by hierarchical cluster analysis (HCA) and principal component analysis (PCA). This study presents a systematic study on the phenolic compounds in Chinese jujube leaves of different cultivars.
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34

Offor, Benedict C., Msizi I. Mhlongo, Paul A. Steenkamp, Ian A. Dubery, and Lizelle A. Piater. "Untargeted Metabolomics Profiling of Arabidopsis WT, lbr-2-2 and bak1-4 Mutants Following Treatment with Two LPS Chemotypes." Metabolites 12, no. 5 (April 22, 2022): 379. http://dx.doi.org/10.3390/metabo12050379.

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Plants perceive pathogenic threats from the environment that have evaded preformed barriers through pattern recognition receptors (PRRs) that recognise microbe-associated molecular patterns (MAMPs). The perception of and triggered defence to lipopolysaccharides (LPSs) as a MAMP is well-studied in mammals, but little is known in plants, including the PRR(s). Understanding LPS-induced secondary metabolites and perturbed metabolic pathways in Arabidopsis will be key to generating disease-resistant plants and improving global plant crop yield. Recently, Arabidopsis LPS-binding protein (LBP) and bactericidal/permeability-increasing protein (BPI)-related proteins (LBP/BPI related-1) and (LBP/BPI related-2) were shown to perceive LPS from Pseudomonas aeruginosa and trigger defence responses. In turn, brassinosteroid insensitive 1 (BRI1)-associated receptor kinase 1 (BAK1) is a well-established co-receptor for several defence-related PRRs in plants. Due to the lack of knowledge pertaining to LPS perception in plants and given the involvement of the afore-mentioned proteins in MAMPs recognition, in this study, Arabidopsis wild type (WT) and mutant (lbr2-2 and bak1-4) plants were pressure-infiltrated with LPSs purified from Pseudomonas syringae pv. tomato DC3000 (Pst) and Xanthomonas campestris pv. campestris 8004 (Xcc). Metabolites were extracted from the leaves at four time points over a 24 h period and analysed by UHPLC-MS, generating distinct metabolite profiles. Data analysed using unsupervised and supervised multivariate data analysis (MVDA) tools generated results that reflected time- and treatment-related variations after both LPS chemotypes treatments. Forty-five significant metabolites were putatively annotated and belong to the following groups: glucosinolates, hydroxycinnamic acid derivatives, flavonoids, lignans, lipids, oxylipins, arabidopsides and phytohormones, while metabolic pathway analysis (MetPA) showed enrichment of flavone and flavanol biosynthesis, phenylpropanoid biosynthesis, alpha-linolenic acid metabolism and glucosinolate biosynthesis. Distinct metabolite accumulations depended on the LPS chemotype and the genetic background of the lbr2-2 and bak1-4 mutants. This study highlights the role of LPSs in the reprogramming Arabidopsis metabolism into a defensive state, and the possible role of LBR and BAK1 proteins in LPSs perception and thus plant defence against pathogenic bacteria.
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Oganesyan, Eduard T., and Stanislav S. Shatokhin. "USING QUANTUM-CHEMICAL PARAMETERS FOR PREDICTING ANTI-RADICAL (НО∙) ACTIVITY OF RELATED STRUCTURES CONTAINING A CINNAMOYL FRAGMENT II. DERIVATIVES OF 2’,4’-DIHYDROXYCHALCONE, FLAVANONE AND FLAVONE, CONTAINING A HYDROXY GROUP IN POSITION 7." Pharmacy & Pharmacology 8, no. 2 (October 14, 2020): 112–23. http://dx.doi.org/10.19163/2307-9266-2020-8-2-112-123.

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42 derivatives of 2’,4’-dihydroxychalcone, flavanone and flavone, containing the hydroxy group in position 7 (ring "A"), as well as substituents in the ring "B", have been studied.The aim is to study the quantum-chemical parameters of 2',4'-dihydroxychalcone, flavanone and flavone derivatives containing a hydroxy group in position 7, in order to identify the effect of substituents on Mulliken charges (a.e) in the aromatic core "A", bond numbers (Nµ), the unsaturation index (IUA) and the electron density of the carbon atoms of the cinnamoyl fragment.Materials and methods. The listed above parameters have been calculated by the semi-empirical method PM7 (WinMopac 2016 program) on the workstation with an Intel Xeon E5-1620 3.5 GHz processor, 20 GB of RAM.Results. The analysis of the values of quantum-chemical parameters, as well as their comparison with the corresponding indicators presented in Report I, revealed a number of important features associated with the influence of the hydroxy group in position 7 (ring "A") on the studied quantum-chemical parameters of molecules. It has been established that the hydroxy group in the ring “A” does not significantly affect the Mulliken charge and the electron density of the carbon atoms of the propenone unit C-7→C-8→C-9. On atom C-9 (carbonyl carbon), the Mulliken charge always has a positive value, and the electron density is about 3.4670-3.4840 for all three groups of compounds. The transition from 2’,4’-dihydroxychalcone to flavanone and flavone by the formation of the pyrone heterocycle, is accompanied by an increase in the negative charge on C-8, which can be explained by the involvement of the oxygen heteroatom in the transmission of electronic effects. The hydroxy group in the ring “A”, has practically no effect on the charge and electron density of atoms. An analysis of the values of bond numbers and unsaturation indices suggests that atoms C-1 of 2’,4’-dihydroxychalcone and 7-hydroxyflavanone derivatives, are characterized by the lowest Nµ value; the lowest bond numbers are characteristic for atom C-8 derivatives of 7-hydroxyflavone. Consequently, the primary attack of the HO·radical will be directed at C-1 (in chalcones and flavanones) and at C-8 in flavones.Conclusion. The performed quantum-chemical calculations make it possible to analyze the effect on the main quantum-chemical parameters of the molecule, which can be useful in predicting the biological activity of flavanoid compounds due to their antiradical effect on reactive oxygen intermediate species (ROIs).
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Yan-Nan, He, Ning Peng-Fei, Yue Tai-Xin, and Zhang Zhen-Wen. "Comparing phenolic composition of Cabernet Gernischet wines between rain-shelter cultivation and open-field cultivation." Czech Journal of Food Sciences 34, No. 3 (June 17, 2016): 254–70. http://dx.doi.org/10.17221/429/2015-cjfs.

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The phenolic compounds of Vitis vinifera cv. Cabernet Gernischet wine in 2010 and 2011 vintage from rain-shelter cultivation and open-field cultivation were detected and compared by high performance liquid chromatography coupled with diode array detector and electrospray ionisation mass spectrometry. The results showed that rain-shelter cultivation increased the total anthocyanin and non-anthocyanin phenolic compound concentration. For the compositions, ratios of peonidin-derivative and malvidin-derivative pigments were similar in the two vintages, rain-shelter cultivation increased the proportion of these derivatives; ratios of delphinidin-derivative and petunidin-derivative pigments were different in the two vintages. In the wine of rain-shelter cultivation, the ratio of flavan-3-ol and hydroxybenzoic acids was increased, the ratio of flavonol was decreased and the composition of other compounds varied between the two vintages. To most of the phenolic compounds identified, their content in wine under rain-shelter cultivation was higher compared to those under open-field cultivation.
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Maciel Diogo, Gabriela, Josimara Souza Andrade, Policarpo Ademar Sales Junior, Silvane Maria Fonseca Murta, Viviane Martins Rebello Dos Santos, and Jason Guy Taylor. "Trypanocidal Activity of Flavanone Derivatives." Molecules 25, no. 2 (January 17, 2020): 397. http://dx.doi.org/10.3390/molecules25020397.

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Chagas disease, also known as American trypanosomiasis, is classified as a neglected disease by the World Health Organization. For clinical treatment, only two drugs have been on the market, Benznidazole and Nifurtimox, both of which are recommended for use in the acute phase but present low cure rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology was utilized that allowed for the simultaneous use of both parasite forms responsible for human infection. The majority of the tested compounds displayed promising anti-Trypanosoma cruzi activity and the most potent flavanone bearing a nitrofuran moiety was more potent than the reference drug, Benznidazole.
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38

Syah, Yana M., and Emilio L. Ghisalberti. "Flavanone derivatives from Macaranga tanarius." Biochemical Systematics and Ecology 62 (October 2015): 151–54. http://dx.doi.org/10.1016/j.bse.2015.08.009.

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39

Stec, Katarzyna, Joanna Kozłowska, Anna Wróblewska-Kurdyk, Bożena Kordan, Mirosław Anioł, and Beata Gabryś. "Effect of Naringenin and Its Derivatives on the Probing Behavior of Myzus persicae (Sulz.)." Molecules 25, no. 14 (July 13, 2020): 3185. http://dx.doi.org/10.3390/molecules25143185.

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Substances that alter insect behavior have attracted a lot of attention as potential crop protection agents. Naringenin (5,7,4′-trihydroxyflavanone) is a naturally occurring bioactive flavanone. We evaluated the influence of naringenin on aphid activities during individual phases of probing and feeding and the effect of structural modifications of naringenin on its activity towards aphids. We monitored the probing behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) using the Electrical Penetration Graph (EPG) technique. The chemical modifications were the substitution of hydrogen atoms with methyl, ethyl or pentyl groups and the replacement of the carbonyl group in naringenin and its derivatives with an oxime moiety. Depending on the substituents, the activity of naringenin-derived compounds varied in potency and mode of action. Naringenin was an attractant of moderate activity, which enhanced sap ingestion. The naringenin derivative with two methyl groups—7,4′-di-O-methylnaringenin—was a deterrent, which hindered aphid probing in non-phloem tissues. Naringenin oxime derivatives with methyl substituents—7,4′-di-O-methylnaringenin oxime, 7-O-methylnaringenin oxime, and 5,7,4′-tri-O-methylnaringenin oxime—and the derivative with a pentyl substituent—7-O-pentylnaringenin oxime—were strong attractants which stimulated aphid probing in non-phloem tissues and the ingestion of phloem sap.
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40

Chand, Karam, Amir Nasrolahi Shirazi, Preeti Yadav, Rakesh K. Tiwari, Meena Kumari, Keykavous Parang, and Sunil K. Sharma. "Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl- and pyranochromen-2-one derivatives." Canadian Journal of Chemistry 91, no. 8 (August 2013): 741–54. http://dx.doi.org/10.1139/cjc-2013-0053.

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A series of 6- and 8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with 6-cinnamoyl analogues. Among all of the hybrid chromen-2-one − chalcone/flavanone compounds, a 7-hydroxy-8-cinnamoylchromen-2-one derivative 35 was found to be consistently active against all the cancer cell lines and inhibited the cell proliferation of SK-OV-3, CCRF-CEM, and MCF-7 by 63%, 50%, and 43%, respectively, at a concentration of 50 μmol/L after 72 h of incubation. This compound also exhibited the highest Src kinase inhibition (IC50 = 14.5 μmol/L). Structure−activity relationship studies provided insights for designing the next generation of chromen-2-one − chalcone hybrid prototypes and the development of new leads as anticancer agents and (or) Src kinase inhibitors.
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41

Sykuła, Anna, Agnieszka Kowalska-Baron, Krystian Gałęcki, Paulina Błazińska, and Elżbieta Łodyga-Chruścińska. "Structural and Spectral Investigation of a Series of Flavanone Derivatives." Molecules 26, no. 5 (February 28, 2021): 1298. http://dx.doi.org/10.3390/molecules26051298.

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Four flavanone Schiff bases (E)-1-(2-phenylchroman-4-ylidene)thiosemicarbazide (FTSC) (1), N′,2-bis((E)-2-phenylchroman-4-ylidene)hydrazine-1-carbothiohydrazide (FTCH) (2), (E)-N’-(2-phenylchroman-4-ylidene)benzohydrazide (FHSB) (3) and (E)-N′-(2-phenylchroman-4-ylidene)isonicotinohydrazide (FIN) (4) were synthesized and evaluated for their electronic and physicochemical properties using experimental and theoretical methods. One of them, (2), consists of two flavanone moieties and one substituent, the rest of the compounds (1, 3, 4) comprises of a flavanone-substituent system in relation to 1:1. To uncover the structural and electronic properties of flavanone Schiff bases, computational simulations and absorption spectroscopy were applied. Additionally, binding efficiencies of the studied compounds to serum albumins were evaluated using fluorescence spectroscopy. Spectral profiles of flavanone Schiff bases showed differences related to the presence of substituent groups in system B of the Schiff base molecules. Based on the theoretically predicted chemical descriptors, FTSC is the most chemically reactive among the studied compounds. Binding regions within human and bovine serum albumins of the ligands studied are in the vicinity of the Trp residue and a static mechanism dominates in fluorescence quenching.
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42

Hsu, Feng-Lin, Yan-Jyu Tsai, Mei-Chuan Kao, and Chieh-Fu Chen. "Antihepatotoxic Activity of Phenolic Flavan-3-ols and Their Derivatives." American Journal of Chinese Medicine 21, no. 01 (January 1993): 45–50. http://dx.doi.org/10.1142/s0192415x93000066.

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The protective activity against carbon tetrachloride induced hepatotoxicity of several phenolic flavan-3-ols and their derivatives has been assessed. Our research showed that monomers possessing a pyrogallol moiety as the B-ring had greater activity and this was not directly related to the stereo-chemistry of the hydroxyl group at C-3 in the flavan unit. However, when a galloyl group was linked to the hydroxyl group to form a gallate, this product exhibited markedly more activity than other analogs. These results suggest that the antihepatotoxic activity of phenolic flavan-3-ols and their derivatives seem to be related to the galloylation at the C-3 hydroxyl group in the flavan skeleton rather than the structure of another moiety or the degree of condensation.
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43

Wang, Enhua, Lishou Yang, Qian Yang, Fanghong Yang, Ji Luo, Menglan Gan, Xue Wang, Shanmin Song, Yang Lei, and Xiaosheng Yang. "Polyphosphoric acid-promoted one-pot synthesis and neuroprotective effects of flavanones against NMDA-induced injury in PC12 cells." RSC Advances 12, no. 43 (2022): 28098–103. http://dx.doi.org/10.1039/d2ra03562f.

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44

Conidi, Egea-Corbacho, and Cassano. "A Combination of Aqueous Extraction and Polymeric Membranes as a Sustainable Process for the Recovery of Polyphenols from Olive Mill Solid Wastes." Polymers 11, no. 11 (November 12, 2019): 1868. http://dx.doi.org/10.3390/polym11111868.

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Polyamide commercial membranes in flat-sheet configuration and with molecular weight cut-off (MWCO) in the range of ultrafiltration (UF) to nanofiltration (NF) were tested for the recovery of phenolic compounds from clarified olive mill solid waste (OMSW) aqueous extracts. The performance of selected membranes was evaluated in terms of productivity (permeate flux) and selectivity towards biologically active compounds (such as phenolic compounds, flavanols, and hydroxycinnamic acids derivatives) and total antioxidant activity (TAA) as a function of transmembrane pressure (TMP). NF membranes produced higher permeate fluxes and a lower fouling index in comparison with UF membranes. Retention of bioactive compounds was also significantly higher for NF membranes than for UF membranes. In particular, membranes with MWCO in the range 150–500 Da showed rejection towards flavanols and hydroxycinnamic acid derivatives of about 100%. On the other hand, the rejection towards TAA and total polyphenols was of about 90% and 72%, respectively. Therefore, NF retentate fractions appear of practical interest for the production of food additives and food supplements due to their high antioxidant activity.
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Chen, R. C., G. B. Sun, J. Wang, H. J. Zhang, and X. B. Sun. "Naringin protects against anoxia/reoxygenation-induced apoptosis in H9c2 cells via the Nrf2 signaling pathway." Food & Function 6, no. 4 (2015): 1331–44. http://dx.doi.org/10.1039/c4fo01164c.

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46

Sinyeue, Cynthia, Mariko Matsui, Michael Oelgemöller, Frédérique Bregier, Vincent Chaleix, Vincent Sol, and Nicolas Lebouvier. "Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents." Molecules 27, no. 6 (March 9, 2022): 1781. http://dx.doi.org/10.3390/molecules27061781.

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Flavonoids are polyphenols with broad known pharmacological properties. A series of 2,3-dihydroflavanone derivatives were thus synthesized and investigated for their anti-inflammatory activities. The target flavanones were prepared through cyclization of 2′-hydroxychalcone derivatives, the later obtained by Claisen–Schmidt condensation. Since nitric oxide (NO) represents an important inflammatory mediator, the effects of various flavanones on the NO production in the LPS-induced RAW 264.7 macrophage were assessed in vitro using the Griess test. The most active compounds were flavanone (4G), 2′-carboxy-5,7-dimethoxy-flavanone (4F), 4′-bromo-5,7-dimethoxy-flavanone (4D), and 2′-carboxyflavanone (4J), with IC50 values of 0.603, 0.906, 1.030, and 1.830 µg/mL, respectively. In comparison, pinocembrin achieved an IC50 value of 203.60 µg/mL. Thus, the derivatives synthesized in this work had a higher NO inhibition capacity compared to pinocembrin, demonstrating the importance of pharmacomodulation to improve the biological potential of natural molecules. SARs suggested that the use of a carboxyl-group in the meta-position of the B-ring increases biological activity, whereas compounds carrying halogen substituents in the para-position were less active. The addition of methoxy-groups in the meta-position of the A-ring somewhat decreased the activity. This study successfully identified new bioactive flavanones as promising candidates for the development of new anti-inflammatory agents.
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Fu, X., T. Sévenet, F. Remy, M. Païs, A. Hamid A. Hadi, and L. M. Zeng. "Flavanone and Chalcone Derivatives from Cryptocarya kurzii." Journal of Natural Products 56, no. 7 (July 1993): 1153–63. http://dx.doi.org/10.1021/np50097a021.

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48

Shi, Lei, Xiu E. Feng, Jing Rong Cui, Lian Hua Fang, Guan Hua Du, and Qing Shan Li. "Synthesis and biological activity of flavanone derivatives." Bioorganic & Medicinal Chemistry Letters 20, no. 18 (September 2010): 5466–68. http://dx.doi.org/10.1016/j.bmcl.2010.07.090.

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Zheng, Xu Xu, Jing Jing Xie, Zhong Yi Yin, and Jia Jia Jing. "A Simple Method of Cyclization of the 2'-Hydroxychalcone with Polystyrene-Pyridine Resine under Mild Conditions." Advanced Materials Research 295-297 (July 2011): 1156–59. http://dx.doi.org/10.4028/www.scientific.net/amr.295-297.1156.

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The satisfying cyclization of 2’-hydroxy chalcone to flavanone using polystyrene-pyridine resine as catalyst and methanol as solvent under mild conditions is reported here. The method is appropriate for 2’-hydroxy chalcone derivatives with electron group in B-ring.
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Mphahlele, Malose J. "ChemInform Abstract: Schmidt Reaction of Flavanone Derivatives: Synthesis of Benzoheterazepine Derivatives." ChemInform 42, no. 21 (April 28, 2011): no. http://dx.doi.org/10.1002/chin.201121212.

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