Journal articles: 'Anthraquinone'

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Drummond, Christopher A., Maria Teresa Molina, Sandra Taliansky, Carl R. Breidenbach, and Carmen F. Fioravanti. "Effects of Quinizarin and Five Synthesized Derivatives on Fifth Larval Instar Midgut Ecdysone 20-Monooxygenase Activity of the Tobacco HornwormManduca sexta." International Journal of Zoology 2014 (2014): 1–8. http://dx.doi.org/10.1155/2014/261512.

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The plant allelochemical, quinizarin (1,4-dihydroxy-9,10-anthraquinone), and five anthraquinones that were synthesized from quinizarin, namely, 1,4-anthraquinone; 2-hydroxy-1,4-anthraquinone; 2-methoxy-1,4-anthraquinone; 9-hydroxy-1,4-anthraquinone; and 9-methoxy-1,4-anthraquinone, were assessed as to their effects on the essential, P450-dependent ecdysone 20-monooxygenase system of the insect modelManduca sexta(tobacco hornworm). This steroid hydroxylase converts the arthropod molting hormone, ecdysone, to the physiologically required 20-hydroxyecdysone form.M. sextafifth larval instar midgut homogenates were incubated with increasing concentrations (10−8to 10−3 M) of each of the six anthraquinones followed by ecdysone 20-monooxygenase assessments using a radioenzymological assay. Four of the five anthraquinones exhibitedI50’s of about4×10-6to6×10-2 M. The most effective inhibitors were 2-methoxy-1,4-anthraquinone and 1,4-anthraquinone followed by 9-hydroxy-1,4 anthraquinone and 9-methoxy-1,4-anthraquinone. At lower concentrations the latter anthraquinone stimulated E20M activity. Quinizarin was less inhibitory and 2-hydroxy-1,4-anthraquinone was essentially without effect. Significantly, these studies make evident for the first time that anthraquinones can affect insect E20M activity, and thus insect endocrine regulation and development, and that a relationship between anthraquinone structure and effectiveness is apparent. These studies represent the first demonstrations of anthraquinones affecting any steroid hydroxylase system.

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Malak, Lourin G., Daoud W. Bishay, Afaf M. Abdel-Baky, Ahmed M. Moharram, Stephen J. Cutler, and Samir A. Ross. "New Anthraquinone Derivatives from Geosmithia lavendula." Natural Product Communications 8, no. 2 (February 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800215.

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A phytochemical study of Geosmithia lavendula Pitt led to the isolation of three new anthraquinones: 1-acetyl-2,4,6,8-tetrahydroxy-9,10-anthraquinone (1), 2-acetyl-1,4,5,7-tetrahydroxy-9,10-anthraquinone (2), and 1-acetyl-2,4,5,6,7-pentahydroxy-9,10-anthraquinone (3), as well as another new compound named didodecyl thiodipropionate (propionic acid, 3,3-sulfinyl di-1,1′-didodecyl ester) (4), along with ten known compounds: 1-acetyl-2,4,5,7-tetrahydroxy-9,10- anthraquinone (rhodolamprometrin) (5), 1-acetyl-2,4,5,7,8-pentahydroxy-9,10-anthraquinone (6), (22E)-ergosta-6,22-diene-3β,5α,8α-triol, p-hydroxybenzyl alcohol, oleic acid, D-mannitol, palmitic acid, stearic acid, cis-vaccenic acid and 2-decenal. The structures of the isolated metabolites were elucidated based on NMR spectroscopic and mass spectrometric data. Compound 1 exhibited moderate activity against methicillin resistant Staphylococcus aureus with an IC50 value of 16.1 μg/mL.

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Gao, Huiyu, Jianbo Yang, Xueting Wang, Yunfei Song, Xianlong Cheng, Feng Wei, Ying Wang, Donglin Gu, Hua Sun, and Shuangcheng Ma. "Exploratory Quality Control Study for Polygonum multiflorum Thunb. Using Dinuclear Anthraquinones with Potential Hepatotoxicity." Molecules 27, no. 19 (October 10, 2022): 6760. http://dx.doi.org/10.3390/molecules27196760.

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In recent years, the hepatotoxicity of Polygoni Multiflora Radix (PMR) has attracted increased research interest. Some studies suggest that anthraquinone may be the main hepatotoxic component. Most of the relevant studies have focused on the mononuclear anthraquinone component rather than binuclear anthraquinones. The hepatotoxicity of dinuclear anthraquinone (dianthrone) was investigated in a cell-based model. Next, a method for the determination of six free and total dianthonones in PMR and PMR Praeparata (PMRP) was established using ultra-high-performance liquid chromatography triple quadrupole mass spectrometry (UPLC-QQQ-MS/MS), which was then used to analyze the collected samples. The data show that four binuclear anthraquinone compounds were hepatotoxic and may be potential toxicity indicators for the safety evaluation of PMR and PMRP. Herein, we provide a theoretical basis for the improvement of PMRP quality standards.

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Branco, Alexsandro, Angelo C. Pinto, Jan Schripsema, and Raimundo Braz-Filho. "Anthraquinones from the bark of Senna macranthera." Anais da Academia Brasileira de Ciências 83, no. 4 (December 2011): 1159–64. http://dx.doi.org/10.1590/s0001-37652011000400003.

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2-acetyl physcion (2-acetyl-1,8-dihydroxy-6-methoxy-3-methyl-9,10-anthraquinone, 2), a rare anthraquinone, was isolated from Senna macranthera var. nervosa (Vogel) H.S. Irwin & Barneby (Fabaceae). The chemical structure was elucidated and all ¹H and 13C NMR chemical shifts were assigned by NMR one- (¹HNMR, {¹H}-13CNMR, and APT-13CNMR) and two (COSY, NOESY, HMQC and HMBC) dimensional of this natural compound. Furthermore, the minor anthraquinones chrysophanol (3), chrysophanol-8-methyl ether (4) and physcion (5) were characterized by GC-MS analysis. The occurrence of the anthraquinones 3-5 confirms that S. macranthera is a typical representative of the genus Senna.

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Zhang, Rongfei, Yuanyuan Miao, Lingyun Chen, Shanyong Yi, and Ninghua Tan. "De Novo Transcriptome Analysis Reveals Putative Genes Involved in Anthraquinone Biosynthesis in Rubia yunnanensis." Genes 13, no. 3 (March 16, 2022): 521. http://dx.doi.org/10.3390/genes13030521.

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Rubia yunnanensis Diels (R. yunnanensis), a Chinese perennial plant, is well-known for its medicinal values such as rheumatism, contusion, and anemia. It is rich in bioactive anthraquinones, but the biosynthetic pathways of anthraquinones in R. yunnanensis remain unknown. To investigate genes involved in anthraquinone biosynthesis in R. yunnanensis, we generated a de novo transcriptome of R. yunnanensis using the Illumina HiSeq 2500 sequencing platform. A total of 636,198 transcripts were obtained, in which 140,078 transcripts were successfully annotated. A differential gene expression analysis identified 15 putative genes involved in anthraquinone biosynthesis. Additionally, the hairy roots of R. yunnanensis were treated with 200 µM Methyl Jasmonate (MeJA). The contents of six bioactive anthraquinones and gene expression levels of 15 putative genes were measured using ultra performance liquid chromatography coupled with mass spectrometry (UPLC-MS/MS) and real-time quantitative polymerase chain reaction (RT-qPCR), respectively. The results showed that the expressions levels for 11 of the 15 genes and the contents of two of six anthraquinones significantly increased by MeJA treatment. Pearson’s correlation analyses indicated that the expressions of 4 of the 15 putative genes were positively correlated with the contents of rubiquinone (Q3) and rubiquinone-3-O-β-d-xylopranosyl-(1→6)-β-d-glucopyranoside (Q20). This study reported the first de novo transcriptome of R. yunnanensis and shed light on the anthraquinone biosynthesis and genetic information for R. yunnanensis.

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Ullah, Hossain, Junhyeong Kim, Naveed Rehman, Hye-Jin Kim, Mi-Jeong Ahn, and Hye Chung. "A Simple and Sensitive Liquid Chromatography with Tandem Mass Spectrometric Method for the Simultaneous Determination of Anthraquinone Glycosides and Their Aglycones in Rat Plasma: Application to a Pharmacokinetic Study of Rumex acetosa Extract." Pharmaceutics 10, no. 3 (July 20, 2018): 100. http://dx.doi.org/10.3390/pharmaceutics10030100.

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Rumex acetosa (R. acetosa) has been used in folk remedies for gastrointestinal disorders and cutaneous diseases. Rumex species, in particular, contain abundant anthraquinones. Anthraquinone glycosides and aglycones show different bioactive effects. However, information on the pharmacokinetics of anthraquinone glycosides is limited, and methods to quantify anthraquinone glycosides in plasma are rarely available. A simple and sensitive liquid chromatography-tandem mass spectrometric bioanalytical method for the simultaneous determination of both anthraquinone glycosides and their aglycones, including emodin, emodin-8-O-β-d-glucoside, chrysophanol, chrysophanol-8-O-β-d-glucoside, physcion, and physcion-8-O-β-d-glucoside , in a low volume of rat plasma (20 µL) was established. A simple and rapid sample preparation was employed using methanol as a precipitating agent with appropriate sensitivity. Chromatographic separation was performed on HPLC by using a biphenyl column with a gradient elution using 2 mM ammonium formate (pH 6) in water and 2 mM ammonium formate (pH 6) in methanol within a run time of 13 min. The anthraquinones were detected on triple-quadrupole mass spectrometer in negative ionization mode using multiple-reaction monitoring. The method was validated in terms of selectivity, linearity, accuracy, precision, recovery, and stability. The values of the lower limit of quantitation of anthraquinones were 1–20 ng/mL. The intra-batch and inter-batch accuracies were 96.7–111.9% and the precision was within the acceptable limits. The method was applied to a pharmacokinetic study after oral administration of R. acetosa 70% ethanol extract to rats at a dose of 2 g/kg.

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7

Yang, Yong, Qiao-Xia Wu, and Min Xue. "Bifurcated hydrogen bonding mediated planar 9,10-anthraquinone dyes: synthesis, structure and properties." RSC Advances 5, no. 37 (2015): 28932–37. http://dx.doi.org/10.1039/c5ra01682g.

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By acylation of mono- and diamino-9,10-anthraquinones with o-alkoxylbenzene carbonyl chloride or o-alkoxylnaphthalene carbonyl chloride, a series of planar 9,10-anthraquinone dyes were designed and synthesized.

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8

Manojlovic, N. T., S. Solujic, S. Sukdolak, and Lj Krstic. "Isolation and antimicrobial activity of anthraquinones from some species of the lichen genus Xanthoria." Journal of the Serbian Chemical Society 65, no. 8 (2000): 555–60. http://dx.doi.org/10.2298/jsc0008555m.

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The isolation of six anthraquinones, erythroglaucin, physcion, xanthorin, emodin, fallacinal and teloschistin, from three species of the lichen genus Xanthoria (X. fallax, X. eleg?ns and A. policarpa) is reported. Physcion is the dominant anthraquinone in all species. The anthraquinones showed broad-spectrum antifungal activity and selective activity against some phytopathogenic bacterial species.

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Ammar Rushdan, Nur Afiqah Nadhiah, Nurunajah Ab Ghani, and Nurulfazlina Edayah Rasol. "Review on Anthraquinones Isolated from Rubiaceae Family." Journal of Science and Mathematics Letters 11, Special (November 9, 2023): 163–74. http://dx.doi.org/10.37134/jsml.vol11.sp.18.2023.

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A current economic trend is to highlight natural resources and many plant species are rich sources of anthraquinones. Anthraquinones are a diverse group of natural compounds extensively studied in various articles. Commonly used for dyes with 30% of it contributed to textile industry. Anthraquinone plays an important chromophore in cancer chemotherapy. They are widely distributed in Rubiaceae family and exhibit various biological activities. Malaysian Rubiaceae, especially plants from Morinda, Rennellia, Psychotria, and Prismatomeris genera, have been known to be rich in anthraquinone content, especially in the roots. The current review aims to provide a comprehensive update on the isolation of anthraquinones from Rubiaceae family in Malaysia. It also discussed the taxonomy, chemistry, and pharmacology studies of the genus. Through the years, 45 anthraquinones have been reported from various species of Rubiaceae demonstrating promising pharmacological activities. The information presented in this review can provide a scientific foundation for future research on the possible therapeutic applications of the species. Enhancing the links between plant biological effects and traditional uses with their chemical characterization.

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Hafez Ghoran, Salar, Fatemeh Taktaz, Seyed Abdulmajid Ayatollahi, and Anake Kijjoa. "Anthraquinones and Their Analogues from Marine-Derived Fungi: Chemistry and Biological Activities." Marine Drugs 20, no. 8 (July 25, 2022): 474. http://dx.doi.org/10.3390/md20080474.

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Anthraquinones are an interesting chemical class of polyketides since they not only exhibit a myriad of biological activities but also contribute to managing ecological roles. In this review article, we provide a current knowledge on the anthraquinoids reported from marine-derived fungi, isolated from various resources in both shallow waters such as mangrove plants and sediments of the mangrove habitat, coral reef, algae, sponges, and deep sea. This review also tentatively categorizes anthraquinone metabolites from the simplest to the most complicated scaffolds such as conjugated xanthone–anthraquinone derivatives and bianthraquinones, which have been isolated from marine-derived fungi, especially from the genera Apergillus, Penicillium, Eurotium, Altenaria, Fusarium, Stemphylium, Trichoderma, Acremonium, and other fungal strains. The present review, covering a range from 2000 to 2021, was elaborated through a comprehensive literature search using the following databases: ACS publications, Elsevier, Taylor and Francis, Wiley Online Library, MDPI, Springer, and Thieme. Thereupon, we have summarized and categorized 296 anthraquinones and their derivatives, some of which showed a variety of biological properties such as enzyme inhibition, antibacterial, antifungal, antiviral, antitubercular (against Mycobacterium tuberculosis), cytotoxic, anti-inflammatory, antifouling, and antioxidant activities. In addition, proposed biogenetic pathways of some anthraquinone derivatives are also discussed.

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11

Griffiths, Scott, Carl H. Mesarich, Benedetta Saccomanno, Abraham Vaisberg, Pierre J. G. M. De Wit, Russell Cox, and Jérôme Collemare. "Elucidation of cladofulvin biosynthesis reveals a cytochrome P450 monooxygenase required for anthraquinone dimerization." Proceedings of the National Academy of Sciences 113, no. 25 (June 6, 2016): 6851–56. http://dx.doi.org/10.1073/pnas.1603528113.

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Anthraquinones are a large family of secondary metabolites (SMs) that are extensively studied for their diverse biological activities. These activities are determined by functional group decorations and the formation of dimers from anthraquinone monomers. Despite their numerous medicinal qualities, very few anthraquinone biosynthetic pathways have been elucidated so far, including the enzymatic dimerization steps. In this study, we report the elucidation of the biosynthesis of cladofulvin, an asymmetrical homodimer of nataloe-emodin produced by the fungusCladosporium fulvum. A gene cluster of 10 genes controls cladofulvin biosynthesis, which begins with the production of atrochrysone carboxylic acid by the polyketide synthase ClaG and the β-lactamase ClaF. This compound is decarboxylated by ClaH to yield emodin, which is then converted to chrysophanol hydroquinone by the reductase ClaC and the dehydratase ClaB. We show that the predicted cytochrome P450 ClaM catalyzes the dimerization of nataloe-emodin to cladofulvin. Remarkably, such dimerization dramatically increases nataloe-emodin cytotoxicity against mammalian cell lines. These findings shed light on the enzymatic mechanisms involved in anthraquinone dimerization. Future characterization of the ClaM enzyme should facilitate engineering the biosynthesis of novel, potent, dimeric anthraquinones and structurally related compound families.

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Hynninen, Paavo H., Riikka Räisänen, Pia Elovaara, and Eila Nokelainen. "Preparative Isolation of Anthraquinones from the Fungus Dermocybe sanguined Using Enzymatic Hydrolysis by the Endogenous β-Glucosidase." Zeitschrift für Naturforschung C 55, no. 7-8 (August 1, 2000): 600–610. http://dx.doi.org/10.1515/znc-2000-7-820.

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Abstract A new and simple enzymatic method was developed for preparative isolation of anthraquinone pigments from Dermocybe sanguined. The endogenous β-glucosidase of the fungus was used to catalyze the hydrolysis of the O-glycosyl linkage in emodin- and dermocybin-1-β-ᴅ-glucopyranosides. The developed enzymatic method was found to be effective for the pigment isolation, as the hydrolysis occurred virtually completely, thus leading to a high pigment yield. Two fractions were obtained by the method: Fraction 1 (94% of the total pigment amount), containing almost exclusively the main pigments emodin and dermocybin, and Fraction 2 (6% ), containing the anthraquinone carboxylic acids. A 10.5 kg amount of fresh fungi yielded 56 g of Fraction 1 and 3.3 g of Fraction 2 anthraquinones. The anthraquinones in each fraction were separated by thin-layer chromatography using toluene-ethyl acetateethanol- formic acid (10:8:1:2, v/v/v/v) as eluent. The components on the chromatograms were detected and characterized by measurements on a densitometer-spectrophotometer. Combined gas chromatography-mass spectrometry was applied to determine the anthraquinone derivatives of Fraction 1 after methylation and acetylation.

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Anderson, Benjamin R., and Mark G. Kuzyk. "Imaging studies of photodegradation and self-healing in anthraquinone derivative dye-doped PMMA." Physical Chemistry Chemical Physics 22, no. 48 (2020): 28154–64. http://dx.doi.org/10.1039/d0cp05426g.

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We compare the photodegradation and self-healing properties of nine anthraquinone derivatives doped into PMMA using transmission imaging. The results suggests “rules-of-thumb” to predict enhanced photostability and self-healing for anthraquinones.

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Park, Jae Gwang, Seung Cheol Kim, Yun Hwan Kim, Woo Seok Yang, Yong Kim, Sungyoul Hong, Kyung-Hee Kim, et al. "Anti-Inflammatory and Antinociceptive Activities of Anthraquinone-2-Carboxylic Acid." Mediators of Inflammation 2016 (2016): 1–12. http://dx.doi.org/10.1155/2016/1903849.

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Anthraquinone compounds are one of the abundant polyphenols found in fruits, vegetables, and herbs. However, thein vivoanti-inflammatory activity and molecular mechanisms of anthraquinones have not been fully elucidated. We investigated the activity of anthraquinones using acute inflammatory and nociceptive experimental conditions. Anthraquinone-2-carboxylic acid (9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid, AQCA), one of the major anthraquinones identified from Brazilian taheebo, ameliorated various inflammatory and algesic symptoms in EtOH/HCl- and acetylsalicylic acid- (ASA-) induced gastritis, arachidonic acid-induced edema, and acetic acid-induced abdominal writhing without displaying toxic profiles in body and organ weight, gastric irritation, or serum parameters. In addition, AQCA suppressed the expression of inflammatory genes such as cyclooxygenase- (COX-) 2 in stomach tissues and lipopolysaccharide- (LPS-) treated RAW264.7 cells. According to reporter gene assay and immunoblotting analyses, AQCA inhibited activation of the nuclear factor- (NF-)κB and activator protein- (AP-) 1 pathways by suppression of upstream signaling involving interleukin-1 receptor-associated kinase 4 (IRAK1), p38, Src, and spleen tyrosine kinase (Syk). Our data strongly suggest that anthraquinones such as AQCA act as potent anti-inflammatory and antinociceptive componentsin vivo, thus contributing to the immune regulatory role of fruits and herbs.

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Sadiq, Uzma, Fatima Shahid, Harsharn Gill, and Jayani Chandrapala. "The Release Behavior of Anthraquinones Encapsulated into Casein Micelles during In Vitro Digestion." Foods 12, no. 15 (July 27, 2023): 2844. http://dx.doi.org/10.3390/foods12152844.

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The degradation of anthraquinones extracted from aloe vera plants can be prevented by encapsulating them in casein micelles (CMs). The oral, gastric, and intestinal digestion behavior of spray-dried microcapsules of casein micelles loaded with aloe vera-extracted anthraquinone powder (CMAQP), freeze-dried powder (CMFDP), and whole-leaf aloe vera gel (CMWLAG) obtained through ultrasonication was investigated. The results found that CMAQP and CMFDP dissolved slowly and coagulated into large curds during gastric digestion, improving the retention of anthraquinones in the digestive tract. In contrast, CMWLAG structure was destroyed and increased amounts of anthraquinones were released during oral and gastric digestion phases, indicating increased amounts of surface anthraquinones instead of the encapsulation of anthraquinones in the interior of CMs. The strong hydrophobic interactions protected anthraquinones within the core of CM for CMAQP and delayed diffusion. However, during SIF digestion, both CMAQP and CMFDP released significant amounts of anthraquinones, although CMAQP showed a much more controlled release for both aloin and aloe-emodin over SIF digestion time. The release behavior of anthraquinones from CM microcapsules was a function of the type of anthraquinone that was used to encapsulate. The present study provides insight into the release behavior of loaded bioactive compounds using food-grade CMs as the wall material during in vitro digestion and highlights the importance of the type of bioactive component form that will be encapsulated.

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Lyčka, Antonín, Libuše Havlíčková, Alois Koloničný, and Josef Jirman. "15N NMR study of amino-imino tautomerism in derivatives of 1,4-bis(substituted amino)-9,10-anthraquinones and 1,4-bis(substituted amino)-2,3-dihydro-9,10-anthraquinones." Collection of Czechoslovak Chemical Communications 52, no. 3 (1987): 736–41. http://dx.doi.org/10.1135/cccc19870736.

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The 15N chemical shifts and 1J(15N, H) coupling constants of 1,4-bis(substituted amino)-9,10-anthraquinones and 1,4-bis(substituted amino)-2,3-dihydro-9,10-anthraquinones indicate that these derivatives exist as true aminoderivatives except for 1,4-bis(phenylamino)-2,3-dihydro-9,10-anthraquinone which forms a tautomeric mixture of the amino and imino forms in deuteriochloroform and hexadeuteriodimethyl sulphoxide.

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Boniface, PJ, RC Cambie, C. Higgs, PS Rutledge, and PD Woodgate. "Experiments Directed Towards the Synthesis of Anthracyclinones. XXVII. Transformations of 2,3-Bisalkynyl and 2,3-Bisalkenyl Anthraquinones." Australian Journal of Chemistry 48, no. 6 (1995): 1089. http://dx.doi.org/10.1071/ch9951089.

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2,3-Bisalkynyl anthraquinones have been synthesized and their behaviour under Bergman-type cyclization conditions has been studied. Cyclization reactions of 2,3-bis(propenyl)anthraquinones yield a number of products, mechanisms for the formation of which are proposed. An attempt to elaborate an A-ring from the 2,3-allyl side chains of the bisallylated anthraquinone (32) is reported.

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Laub, Annegret, Ann-Katrin Sendatzki, Götz Palfner, Ludger A. Wessjohann, Jürgen Schmidt, and Norbert Arnold. "HPTLC-DESI-HRMS-Based Profiling of Anthraquinones in Complex Mixtures—A Proof-of-Concept Study Using Crude Extracts of Chilean Mushrooms." Foods 9, no. 2 (February 6, 2020): 156. http://dx.doi.org/10.3390/foods9020156.

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High-performance thin-layer chromatography (HPTLC) coupled with negative ion desorption electrospray ionization high-resolution mass spectrometry (DESI-HRMS) was used for the analysis of anthraquinones in complex crude extracts of Chilean dermocyboid Cortinarii. For this proof-of-concept study, the known anthraquinones emodin, physcion, endocrocin, dermolutein, hypericin, and skyrin were identified by their elemental composition. HRMS also allowed the differentiation of the investigated anthraquinones from accompanying compounds with the same nominal mass in the crude extracts. An investigation of the characteristic fragmentation pattern of skyrin in comparison with a reference compound showed, exemplarily, the feasibility of the method for the determination of these coloring, bioactive and chemotaxonomically important marker compounds. Accordingly, we demonstrate that the coupling of HPTLC with DESI-HRMS represents an advanced and efficient technique for the detection of anthraquinones in complex matrices. This analytical approach may be applied in the field of anthraquinone-containing food and plants such as Rheum spp. (rhubarb), Aloe spp., Morinda spp., Cassia spp. and others. Furthermore, the described method can be suitable for the analysis of anthraquinone-based colorants and dyes, which are used in the food, cosmetic, and pharmaceutical industry.

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Bussmann, Rainer W., Lothar Hennig, Athanassios Giannis, Jutta Ortwein, Toni M. Kutchan, and Xi Feng. "Anthraquinone Content in Noni (Morinda citrifoliaL.)." Evidence-Based Complementary and Alternative Medicine 2013 (2013): 1–5. http://dx.doi.org/10.1155/2013/208378.

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Noni has been used in traditional medicine and as food for thousands of years. While the fruits serve as food and internal medicine, leaves were traditionally used only topically. In recent years, concern regarding the possible content of anthraquinones in noni has led to scrutiny by the European Food Safety Authority. Little research existed on the content of anthraquinones in different noni preparations, with no information about the potential effect of harvest and preparation methods. Our research focused on lucidin, alizarin, and rubiadin, the most important anthraquinones from a health perspective. We found that the production process (fermentation/juice production versus drying/lyophilization) has no effect on the anthraquinone content. The source product, however, does have implications: noni fruit puree from which seeds had been removed as well as consumer products produced from such puree had no detectable amounts of any anthraquinones. Products that did contain seed or leaf material in all cases did contain partly significant amounts of anthraquinones. To alleviate safety concerns, we suggest that noni products, whether fermented or unfermented juice or powder, should be derived only from fully ripe noni fruits, and that any seed material needs to be removed during the production process.

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Li, Rong-Rong, Xue-Fang Liu, Su-Xiang Feng, Sheng-Nan Shu, Pei-Yang Wang, Na Zhang, Jian-Sheng Li, and Ling-Bo Qu. "Pharmacodynamics of Five Anthraquinones (Aloe-emodin, Emodin, Rhein, Chysophanol, and Physcion) and Reciprocal Pharmacokinetic Interaction in Rats with Cerebral Ischemia." Molecules 24, no. 10 (May 17, 2019): 1898. http://dx.doi.org/10.3390/molecules24101898.

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(1) Background: Rhubarb anthraquinones—a class of components with neuroprotective function—can be used to alleviate cerebral ischemia reperfusion injury. (2) Methods: The three pharmacodynamic indicators are neurological function score, brain water content, and cerebral infarction area; UPLC-MS/MS was used in pharmacokinetic studies to detect plasma concentrations at different time points, and DAS software was used to calculate pharmacokinetic parameters in a noncompartmental model. (3) Results: The results showed that the pharmacodynamics and pharmacokinetics of one of the five anthraquinone aglycones could be modified by the other four anthraquinones, and the degree of interaction between different anthraquinones was different. The chrysophanol group showed the greatest reduction in pharmacodynamic indicators comparing with other four groups where the rats were administered one of the five anthraquinones, and there was no significant difference between the nimodipine group. While the Aloe-emodin + Physcion group showed the most obvious anti-ischemic effect among the groups where the subjects were administered two of the five anthraquinones simultaneously. Emodin, rhein, chrysophanol, and physcion all increase plasma exposure levels of aloe-emodin, while aloe-emodin lower their plasma exposure levels. (4) Conclusions: This experiment provides a certain preclinical basis for the study of anthraquinone aglycones against cerebral ischemia and a theoretical basis for the study of the mechanism of interaction between anthraquinones.

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Osman, Che Puteh, and Nor Hadiani Ismail. "A REVIEW ON THE CHEMISTRY AND PHARMACOLOGY OF Rennellia elliptica Korth." Indonesian Journal of Tropical and Infectious Disease 6, no. 6 (December 21, 2017): 131. http://dx.doi.org/10.20473/ijtid.v6i6.6642.

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Rennellia elliptica, popularly dubbed as Malaysian Ginseng, is widely used in traditional medicine among the local Jakun community in Endau-Rompin State Park, Pahang, Malaysia. The decoction of the roots is traditionally taken for treatment of body aches, as postpartum tonic, as aphrodisiac and for the treatment of jaundice. In the effort of searching new botanical drugs and drug candidates from tropical rainforest, the team from this laboratory had conducted a sizeable phytochemical and biological screening program of tropical plant at Endau Rompin State Park, Pahang with the help from the indigenous people. R. elliptica showed strong antiplasmodial activity in vitro with the IC50 value of 4.04µg/mL. The comprehensive study on the root extract of R. elliptica in this laboratory yielded seventeen compounds from four different classes, including 2 new pyranoanthraquinones, one new anthraquinone, eleven known anthraquinones, one lactone triterpenoid, one coumarin and one phenolic acid. The chemical profile of the root extract was established using HPLC and the selected marker compounds were used as external standards and quantified using standard calibration curve. Nordamnacanthal 5, damnacanthal 7, 2-formyl-3-hydroxy-9,10-anthraquinone 6, 2-methyl-3-hydroxy-9,10-anthraquinone 11 and 1,2-dimethoxy-6-methyl-9,10-anthraquinone 3 were determined at 3.57, 10.32, 4.47, 12.18 and 4.09 µg/g, respectively. Owing to the toxicity of dichloromethane, the extraction of the desired marker compounds was attempted using accelerated solvent extraction and soxhlet extraction using ethanol and water at different compositions. R. elliptica root extract and the isolated anthraquinones showed potential antiplasmodial activity, and the active compounds were probed for their mode of action. In addition, the dichloromethane root extract of R. elliptica and the selected anthraquinones were screened for anticancer, antioxidant, and α-glucosidase inhibitory activities as well as toxicity study in vitro. The review summarizes the findings on Rennellia elliptica which includes phytochemistry, toxicity and its biological activities. The chemotaxonomic significance of Rennellia elliptica is also discussed

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Chee, Cheok Wui, Nor Hisam Zamakshshari, Vannajan Sanghiran Lee, Iskandar Abdullah, Rozana Othman, Yean Kee Lee, Najihah Mohd Hashim, and Nurshamimi Nor Rashid. "Morindone from Morinda citrifolia as a potential antiproliferative agent against colorectal cancer cell lines." PLOS ONE 17, no. 7 (July 12, 2022): e0270970. http://dx.doi.org/10.1371/journal.pone.0270970.

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There is an increasing demand in developing new, effective, and affordable anti-cancer against colon and rectal. In this study, our aim is to identify the potential anthraquinone compounds from the root bark of Morinda citrifolia to be tested in vitro against colorectal cancer cell lines. Eight potential anthraquinone compounds were successfully isolated, purified and tested for both in-silico and in-vitro analyses. Based on the in-silico prediction, two anthraquinones, morindone and rubiadin, exhibit a comparable binding affinity towards multitargets of β-catenin, MDM2-p53 and KRAS. Subsequently, we constructed a 2D interaction analysis based on the above results and it suggests that the predicted anthraquinones from Morinda citrifolia offer an attractive starting point for potential antiproliferative agents against colorectal cancer. In vitro analyses further indicated that morindone and damnacanthal have significant cytotoxicity effect and selectivity activity against colorectal cancer cell lines.

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Hung, Hsin-Yi, Kun-Ching Cheng, Ping-Chung Kuo, I.-Tsen Chen, Yue-Chiun Li, Tsong-Long Hwang, Sio-Hong Lam, and Tian-Shung Wu. "Chemical Constituents of Hedyotis diffusa and Their Anti-Inflammatory Bioactivities." Antioxidants 11, no. 2 (February 9, 2022): 335. http://dx.doi.org/10.3390/antiox11020335.

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Seven new anthraquinones with rare 2-isopropyldihydrofuran (1–3) and 2,2-dimethylpyrano (4–7) moieties together with thirty-four known compounds were isolated from the extracts of whole Hedyotis diffusa plants. Their structures were elucidated and established by various spectroscopic and spectrometric analytical methods. Among these isolates, selected compounds were examined for their anti-inflammatory activity. The results showed that rare substituted anthraquinones displayed potent inhibitory activity with IC50 values ranging from 0.15 ± 0.01 to 5.52 ± 1.59 µM on the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release cellular models. Meanwhile, the proposed drug target of the active anthraquinone was studied by computer modeling. The binding affinity between the anti-inflammatory anthraquinone and elastase was evaluated by molecular docking. These results provided the scientific insight into the medicinal values of Hedyotis diffusa and vision of development as lead compounds.

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Kunze, Arno, Ludger Witte, Manuel Aregullin, Eloy Rodriguez, and Peter Proksch. "Anthraquinones in the Leaf Beetle Trirhabda geminata (Chrysomelidae)." Zeitschrift für Naturforschung C 51, no. 3-4 (April 1, 1996): 249–52. http://dx.doi.org/10.1515/znc-1996-3-417.

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Abstract Hydroxylated anthraquinones have been found to accumulate in different developmental stages of the chrysomelid beetle Trirhabda geminata. Eggs, larvae and adults were analyzed by HPLC and GC-MS. Each developmental stage analyzed contained 1,8-dihydroxy-3-methyl-anthraquinone (chrysophanol) and 1,8-dihydroxyanthraquinone (chrysazin). No anthraquinones were detected in the faeces of T. geminata. The level of stored anthraqui nones did not change during starvation. In the host plant of this specialist herbivore, the brittlebush Encelia farinosa (Asteraceae), anthraquinones were not detected. Possible biological functions of anthraquinones stored in T. geminata are discussed.

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25

Sadiq, Uzma, Harsharn Gill, Jayani Chandrapala, and Fatima Shahid. "Influence of Spray Drying on Encapsulation Efficiencies and Structure of Casein Micelles Loaded with Anthraquinones Extracted from Aloe vera Plant." Applied Sciences 13, no. 1 (December 22, 2022): 110. http://dx.doi.org/10.3390/app13010110.

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The encapsulation efficiency (EE%) and structural changes within the Anthraquinones-encapsulated casein micelles (CM) powders were evaluated in this study. For this purpose, the anthraquinone powder extracted from Aloevera, its freeze-dried powder (FDP) and whole leaf Aloe vera gel (WLAG) has been encapsulated in CM through ultrasonication prior to spray dying to produce nanocapsules: CM encapsulated anthraquinone powder (CMAQP), CM encapsulated freeze-dried powder (CMFDP) and CM encapsulated Whole leaf aloe vera gel (CMWLAG). Based on the pH of the solution before drying, CMAQP had the highest EE% following spray drying. However, due to air-interface-related dehydration stresses, SD resulted in a slight decrease in the EE% of anthraquinones (aloin, aloe-emodin, and rhein) in CMAQP. Meanwhile, a significant increase in EE% of CMFDP was observed compared to the aqueous state. According to SEM findings, the particle size of CMAQP was 2.39 µm and ξ-potential of ~−17mV. The CMFDP had a rough fractal surface with large particle sizes and potential of 3.49 µm and ~−11mV respectively. CM deformed, having the least EE% and lowest ξ-potential (−4.5 mV). Spray drying enhances melanoidin formation in CMWLAG, as evidenced by the highest chroma values. The results suggested that EE%, stability, and degree of Maillard reaction are closely linked to the type of anthraquinone encapsulated, the pH of the solution, and the nanostructure of casein micelles during spray drying.

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26

Seitimova, Gulnaz A., Aksholpan K. Shokan, Tatyana G. Tolstikova, Nataliya A. Zhukova, Dmitriy Yu Korulkin, Nataliya O. Kudrina, Yuliya A. Litvinenko, Nataliya D. Meduntseva, Nina V. Terletskaya, and Timur E. Kulmanov. "Antiulcer Activity of Anthraquinone–Flavonoid Complex of Rumex tianschanicus Losinsk." Molecules 28, no. 5 (March 3, 2023): 2347. http://dx.doi.org/10.3390/molecules28052347.

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The composition of an ethanol extract from the roots of Rumex tianschanicus Losinsk of the Trans-Ili Alatau wild flora was studied in order to determine its antiulcer activity. The phytochemical composition of the anthraquinone–flavonoid complex from (AFC) R. tianschanicus revealed the presence of numerous polyphenolic compounds, the most abundant of which are anthraquinones (1.77%), flavonoids (6.95%), and tannins (13.39%). The use of column chromatography (CC) and thin-layer chromatography (TLC) in conjunction with UV, IR, NMR spectroscopy, and mass spectrometry data allowed the researchers to isolate and identify the major components of the anthraquinone–flavonoid complex’s polyphenol fraction: physcion, chrysophanol, emodin, isorhamnetin, quercetin, and myricetin. The gastroprotective effect of the polyphenolic fraction of the anthraquinone–flavonoid complex (AFC) of R. tianschanicus roots was examined in an experimental model of rat gastric ulcer induced by indomethacin. The preventive and therapeutic effect of the anthraquinone–flavonoid complex at a dose of 100 mg/kg was analyzed using intragastric administration per day for 1 to 10 days, followed by a histological examination of stomach tissues. It has been demonstrated that prophylactic and prolonged use of the AFC R. tianschanicus in laboratory animals resulted in significantly less pronounced hemodynamic and desquamative changes in the epithelium of gastric tissues. The acquired results thus offer fresh insight into the anthraquinone and flavonoid metabolite component composition of R. tianschanicus roots, and they imply that the examined extract can be used to develop herbal medicines with antiulcer activity.

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27

Kharlamova, T. V. "Anti-fungal activity of anthraquinone derivatives (Part 1)." Chemical Journal of Kazakhstan 78, no. 2 (June 15, 2022): 26–47. http://dx.doi.org/10.51580/2022-2/2710-1185.63.

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The problems of treatment and prevention of infectious diseases, due to the diversity of biological forms of pathogens, the constant emergence of multi-resistant forms, the emergence of new types of dangerous pathogens, determine the relevance of the problem of creating new antimicrobial agents. Over the past few decades, there has been an increase in the incidence of fungal infections worldwide, as well as an increase in the resistance of some types of fungi to various antifungal drugs used in medical practice. The purpose of the review is to provide information on the current state of fungal diseases and the search for new antifungal structures among natural compounds, in particular anthraquinone derivatives. Objects. Derivatives of 9,10-anthraquinone: chrysophanol, emodin, physсion, rhein, aloe-emodin). Results. Currently, special attention has been paid to natural sources of antimicrobial agents, which can be considered as an alternative to traditionally used drugs. Nature is a valuable source of new compounds and a rich arsenal of biologically active metabolites for the search for new drugs. Chemistry of anthraquinone derivatives is an independent and extensive field of organic and bioorganic chemistry with a wide range of practical applications. Quite a large number of compounds of the anthraquinone series have been found in plants, animals, and microorganisms. Many natural and synthetic derivatives of anthraquinones exhibit a variety of pharmacological activities, among which compounds with antitumor, cytostatic, anti-inflammatory, hormonal, antiviral, and other activities have been identified. The review analyzes the antifungal effects of various types of natural anthraquinone molecules (chrysophanol, emodin, physсion, rhein, aloe-emodin), as well as some structurally related derivatives, to assess the effect of structural parameters of molecules on their activity. Conclusion. Natural objects contain a variety of biologically active derivatives of 9,10-anthraquinone. They can be considered as promising structures for the search for new antifungal agents.

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Sadiq, Uzma, Harsharn Gill, and Jayani Chandrapala. "Ultrasound-Assisted Encapsulation of Anthraquinones Extracted from Aloe-Vera Plant into Casein Micelles." Gels 8, no. 9 (September 17, 2022): 597. http://dx.doi.org/10.3390/gels8090597.

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Aloe-vera extracted anthraquinones (aloin, aloe-emodin, rhein) possess a wide range of biological activities, have poor solubility and are sensitive to processing conditions. This work investigated the ultrasound-assisted encapsulation of these extracted anthraquinones (AQ) into casein micelles (CM). The particle size and zeta potential of casein micelles loaded with aloin (CMA), aloe-emodin (CMAE), rhein (CMR) and anthraquinone powder (CMAQ) ranged between 171–179 nm and −23 to −17 mV. The AQ powder had the maximum encapsulation efficiency (EE%) (aloin 99%, aloe-emodin 98% and rhein 100%) and encapsulation yield, while the whole leaf Aloe vera gel (WLAG) had the least encapsulation efficiency. Spray-dried powder (SDP) and freeze-dried powder (FDP) of Aloe vera showed a significant increase in size and zeta potential related to superficial coating instead of encapsulation. The significant variability in size, zeta potential and EE% were related to anthraquinone type, its binding affinity, and its ratio to CM. FTIR spectra confirmed that the structure of the casein micelle remained unchanged with the binding of anthraquinones except in casein micelles loaded with whole-leaf aloe vera gel (CMWLAG), where the structure was deformed. Based on our findings, Aloe vera extracted anthraquinones powder (AQ) possessed the best encapsulation efficiency within casein micelles without affecting its structure. Overall, this study provides new insights into developing new product formulations through better utilization of exceptional properties of casein micelles.

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29

Roy, Joyeeta, Tanushree Mal, Supriti Jana, and Dipakranjan Mal. "Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins." Beilstein Journal of Organic Chemistry 12 (March 16, 2016): 531–36. http://dx.doi.org/10.3762/bjoc.12.52.

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Dibromobenzoisofuranone 12, synthesized in six steps, was regiospecifically annulated with 5-substituted cyclohexenones 13/36 in the presence of LiOt-Bu to give brominated anthraquinones 14/38 in good yields. Darzens condensation of 30 was shown to give chain-elongated anthraquinone 32. Alkaline hydrolysis of 38 furnished 39 representing desulfoproisocrinin F.

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30

Gupta, Richa K., Ganesh M. S. Thakuri, Gan B. Bajracharya, and Ram Narayan Jha. "Synthesis of antioxidative anthraquinones as potential anticancer agents." BIBECHANA 18, no. 2 (June 9, 2021): 143–53. http://dx.doi.org/10.3126/bibechana.v18i2.31234.

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Antioxidant and antibacterial activities of natural anthraquinones namely chrysophanol (1) and emodin (2), and synthesized anthraquinones viz. 2-methylanthraquinone (3), anthraquinone (4), 2-bromoanthraquinone (5), rubiadin (6), chrysophanol diacetate (7), rubiadin diacetate (8) and 1,8-dimethoxy-3-methylanthraquinone (9) were investigated. Anthraquinones 9, 3, 6, 5 and 2 exhibited a high DPPH• radical scavenging capacity (IC50 = <500 μg/mL) showing their therapeutic potentiality for the treatment of cancers. These anthraquinones 1-9 have also displayed a weak to moderate antibacterial activity against Bacillus subtilis. Chrysophanol diacetate (7) including emodin (2) have been appeared as the valuable antibacterials. BIBECHANA 18 (2) (2021) 143-153

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31

Chakiri, Abdel B., and Philip Hodge. "Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups." Royal Society Open Science 4, no. 8 (August 2017): 170451. http://dx.doi.org/10.1098/rsos.170451.

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Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some cases the isopropyl groups migrate cleanly to other ring positions; in other cases they are lost.

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32

Su, Guang-Yao, Ming-Long Chen, and Kui-Wu Wang. "Natural New Bioactive Anthraquinones from Rubiaceae." Mini-Reviews in Organic Chemistry 17, no. 7 (October 9, 2020): 872–83. http://dx.doi.org/10.2174/1570193x17666200107092510.

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Rubiaceae family belongs to the Gentianales, it contains 650 genera and 13,000 species and its worldwide distribution makes it the fourth largest angiosperms. Rubiaceae contains a large amount of anthraquinone compounds, especially in the roots. Anthraquinones are very important natural products with various bioactivities, including antibacterial, antiviral, cytotoxic and antitumor, which make it play an important role in recent research. In the previous study, many researchers have reported anthraquinones from Rubiaceae in different aspects. The present paper provides an overview of the bioactive properties of new naturally occurring anthraquinones and its structural diversity that have been isolated from the Rubiaceae family in recent years. The article covers the literature from 2007 to 2018, overall 95 new anthraquinones.

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33

Shukla, Nivedita, Manmeet Kumar, Akanksha, Ghufran Ahmad, Neha Rahuja, Amar B. Singh, Arvind K. Srivastava, Siron M. Rajendran, and Rakesh Maurya. "Tectone, a New Antihyperglycemic Anthraquinone from Tectona grandis Leaves." Natural Product Communications 5, no. 3 (March 2010): 1934578X1000500. http://dx.doi.org/10.1177/1934578x1000500318.

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A new anthraquinone (3,8-dihydroxy-2-methyl anthraquinone), named tectone (1), along with fourteen known compounds (2-15) comprised of five terpenoids (2-5, 15), four flavonoids (6-9), three flavone glycosides (10-12), and two phenolic glycosides (13-14) were isolated from the chloroform and n-butanol fractions of the ethanol extract of Tectona grandis leaves. Attempts were made to synthesize compound 1. This resulted in the synthesis of three additional anthraquinones (16-18), out of which compound 16 is new. The structures of all compounds were established by spectral analysis. The isolated and synthesized compounds were evaluated for their antihyperglycemic activity. Compounds 1, 2, 4 and 14 showed significant antihyperglycemic activity in streptozotocin-induced diabetic rats at a dose of 100 mg/kg body weight, which is comparable to the standard drug metformin.

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34

Wood, S., J. Huffman, N. Weber, D. Andersen, J. North, B. Murray, R. Sidwell, and B. Hughes. "Antiviral Activity of Naturally Occurring Anthraquinones and Anthraquinone Derivatives." Planta Medica 56, no. 06 (December 1990): 651–52. http://dx.doi.org/10.1055/s-2006-961304.

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35

Zhuravleva, Olesya I., Ekaterina A. Chingizova, Galina K. Oleinikova, Sofya S. Starnovskaya, Alexandr S. Antonov, Natalia N. Kirichuk, Alexander S. Menshov, et al. "Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus." Marine Drugs 21, no. 8 (July 29, 2023): 431. http://dx.doi.org/10.3390/md21080431.

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New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds 1–4 and 6–13 showed a significant antimicrobial effects against Staphylococcus aureus growth, and acruciquinone A (1), dendryol B (4), coniothyrinone B (7), and ω-hydroxypachybasin (9) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding 4, inhibited urease activity. We studied the effects of anthraquinones 1, 4, 7, and 9 and coniothyrinone D (6) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with S. aureus. Anthraquinones significantly reduce the negative impact of S. aureus on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (1) revealed the most pronounced effect.

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Yuan, Jiaqi, Qian He, Shanshan Song, Xiaofei Zhang, Zehong Miao, and Chunhao Yang. "One Pot and Metal-Free Approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones." Molecules 24, no. 16 (August 20, 2019): 3017. http://dx.doi.org/10.3390/molecules24163017.

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Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency, mild conditions, and benign functional group compatibility was reported. A variety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.

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Ha, Nguyen Xuan, Hoang Thi Ngoc Anh, Pham Ngoc Khanh, Vu Thi Ha, Nguyen Viet Ha, Tran Thu Huong, and Nguyen Manh Cuong. "In silico and ADMET study of Morinda longissima phytochemicals against TNF‐α for treatment of inflammation‐mediated diseases." Vietnam Journal of Chemistry 61, S1 (July 2023): 57–63. http://dx.doi.org/10.1002/vjch.202200214.

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AbstractMorinda longissima Y. Z. Ruan (“Nhó đông") belongs to the Rubiaceae family. In Vietnam, the stems and roots of this plant are commonly used to treat liver diseases, such as viral hepatitis and acute and chronic cirrhosis. A phytochemical study of this hepatoprotective plant revealed the presence of 21 natural compounds of different classes, including iridoids, naphthalene glycosides, and especially anthraquinones and anthraquinone glycosides. The primary goal of this study was to investigate the anti‐inflammatory potential of bioactive molecules from M. longissima targeted against TNF‐α using a molecular docking approach. The results revealed that two anthraquinone glycosides, morindone‐6‐O‐β‐gentiobioside (1) and lucidin‐3‐O‐β‐primeveroside (2), had good binding affinities (∆G values of ‐9.21 and ‐8.75 kcal/mol, respectively), better than that of the TNF‐α inhibitor, SPD‐304 (‐8.71 kcal/mol). The in silico ADME parameters of (1) and (2) and other compounds showed good bioavailability based on their absorption, distribution, metabolism, and excretion parameters. In addition, the oral toxicity of these compounds was determined to be low and safe. All this evidence showed it is worth further study and the development of potential anthraquinone glycosides from M. longissima roots as TNF‐α natural inhibitors for the treatment of inflammatory diseases such as rheumatoid arthritis, sclerosis, and hepatitis.

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38

Shupeniuk, Vasyl. "Synthesis and Antimicrobial Activity Of Nitrogen-Containing Anthraquinone Derivatives." Iraqi Journal of Pharmaceutical Sciences ( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512) 31, no. 2 (December 24, 2022): 193–201. http://dx.doi.org/10.31351/vol31iss2pp193-201.

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New substituted anthraquinones with amino derivations fragments were synthesized through the substitution of bromine atom by different amines using the Ullmann coupling reaction. Obtained compounds based on anthraquinone used for experimental antimicrobial studies. The structure of the synthesized compounds was confirmed by LC-MS and 1H, 13C NMR spectroscopy. Studies on planktonic microorganisms have shown that the first synthesized anthraquinone derivatives have an inhibitory effect against bacteria and fungi. The triazene 1-(3-(benzoic acid(triaz-1-en-1-ol(-4-(1H-imidazol-1-yl(-9,10-dioxo-9,10-dihydroanthracene -2-sulfonic acid, have wide spectrum of activity, growth retardation zones against gram-positive microorganisms in the range of 8.41-11.5 mm, gram-negative bacteria 5.87-8.18 mm, fungi of the genus Candida 5.81-7.48 mm. The high antimicrobial activity of this compound is probably due to the presence of benzoic acid in its molecule.

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Friedman, Mendel, Alexander Xu, Rani Lee, Daniel N. Nguyen, Tina A. Phan, Sabrina M. Hamada, Rima Panchel, et al. "The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure." Molecules 25, no. 13 (July 7, 2020): 3101. http://dx.doi.org/10.3390/molecules25133101.

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Plant-derived anthraquinones were evaluated in cell assays for their inhibitory activities against the parasitic protozoa Trichomonas vaginalis human strain G3 that causes the sexually transmitted disease trichomoniasis in women, Tritrichomonas foetus bovine strain D1 that causes sexually transmitted diseases in farm animals (bulls, cows, and pigs), Tritrichomonas foetus-like strain C1 that causes diarrhea in domestic animals (cats and dogs), and bacteria and fungi. The anthraquinones assessed for their inhibitory activity were anthraquinone, aloe-emodin (1,8-dihydroxy-3-hydroxymethylanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), chrysazin (1,8-dihydroxyanthraquinone), emodin (1,3,8-trihydroxy-6-methylanthraquinone), purpurin (1,2,4-trihydroxyanthraquinone), and rhein (1,8-dihydroxy-3-carboxyanthraquinone). Their activities were determined in terms of IC50 values, defined as the concentration that inhibits 50% of the cells under the test conditions and calculated from linear dose response plots for the parasitic protozoa, and zone of inhibition for bacteria and fungi, respectively. The results show that the different substituents on the anthraquinone ring seem to influence the relative potency. Analysis of the structure–activity relationships in protozoa indicates that the aloe-emodin and chrysazin with the highest biological activities merit further study for their potential to help treat the diseases in women and domestic and farm animals. Emodin also exhibited antifungal activity against Candida albicans. The suggested mechanism of action and the additional reported beneficial biological properties of anthraquinones suggest that they have the potential to ameliorate a broad spectrum of human diseases.

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Glavnik, Vesna, and Irena Vovk. "Extraction of Anthraquinones from Japanese Knotweed Rhizomes and Their Analyses by High Performance Thin-Layer Chromatography and Mass Spectrometry." Plants 9, no. 12 (December 11, 2020): 1753. http://dx.doi.org/10.3390/plants9121753.

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Anthraquinones (yellow dyes) were extracted from Japanese knotweed rhizomes with twelve extraction solvents (water; ethanol(aq) (20%, 40%, 60%, 70% and 80%), ethanol, 70% methanol(aq), methanol, 70% acetone(aq), acetone and dichloromethane). The obtained sample test solutions (STSs) were analyzed using high-performance thin-layer chromatography (HPTLC) coupled to densitometry and mass spectrometry (HPTLC–MS/MS) on HPTLC silica gel plates. Identical qualitative densitometric profiles (with anthraquinone aglycones and glycosylated anthraquinones) were obtained for STSs in all the solvents except for the STS in dichloromethane, which enabled the most selective extractions of anthraquinone aglycones emodin and physcion. The highest extraction efficiency, evaluated by comparison of the total peak areas in the densitograms of all STSs scanned at 442 nm, was achieved for 70% acetone(aq). In STS prepared with 70% acetone(aq), the separation of non-glycosylated and glycosylated anthraquinones was achieved with developing solvents toluene–acetone–formic acid (6:6:1, 3:6:1 and 3:3:1 v/v) and dichloromethane–acetone–formic acid (1:1:0.1, v/v). Non-glycosylated anthraquinones were separated only with toluene–acetone–formic acid, among which the best resolution between emodin and physcion gave the ratio 6:6:1 (v/v). This solvent and dichloromethane–acetone–formic acid (1:1:0.1, v/v) enabled the best separation of glycosylated anthraquinones. Four HPTLC-MS/MS methods enabled the identification of emodin and tentative identification of its three glycosylated analogs (emodin-8-O-hexoside, emodin-O-acetyl-hexoside and emodin-O-malonyl-hexoside), while only the HPTLC-MS/MS method with toluene-acetone-formic acid (6:6:1, v/v) enabled the identification of physcion. Changes of the shapes and the absorption maxima (bathochromic shifts) in the absorption spectra after post-chromatographic derivatization provided additional proof for the detection of physcion and rejection of the presence of chrysophanol in STS.

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Cameron, Donald W., Peter G. Griffiths, and Andrew G. Riches. "Synthesis of 2,3-Dioxy-1,4-anthraquinones Related to Tetracenomycins C and X." Australian Journal of Chemistry 52, no. 12 (1999): 1173. http://dx.doi.org/10.1071/ch99181.

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The 2,3-dioxy-1,4-anthraquinones (6) and (7) have been synthesized from the 9,10-anthraquinone (19), through the anthrone (18). Quinones (6) and (7) respectively possess substituents appropriate for three of the four rings of tetracenomycins C (2) and X (3) but they did not show dienophilic properties towards the reactive diene (5). Interaction with the diene was complicated by transsilylation, as was also observed for the model quinone (25).

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Li, Xin, Xiao-Ming Li, and Bin-Gui Wang. "Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis." Marine Drugs 17, no. 1 (December 24, 2018): 8. http://dx.doi.org/10.3390/md17010008.

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Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b,e]oxepine-6,11-dione, 1) by 1D and 2D NMR experiments. However, the minor differences of the chemical shifts between xanthones and anthraquinones were queried, leading to the structure of 1 to be revised as a xanthone analog (8-hydroxy-6-(hydroxymethyl)-3-methoxy-9-oxo-9H-xanthene-1-carboxylic acid, 2) on the basis of a methylation and subsequent NMR measurements, and was confirmed by X-ray crystallographic analysis. The method established in this paper could be applied to the structural re-examination or revision for some of the reported seco-anthraquinone derivatives.

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Andersen, Douglas O., Norbert D. Weber, Steven G. Wood, Bronwyn G. Hughes, Byron K. Murray, and James A. North. "In vitro virucidal activity of selected anthraquinones and anthraquinone derivatives." Antiviral Research 16, no. 2 (September 1991): 185–96. http://dx.doi.org/10.1016/0166-3542(91)90024-l.

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Shen, Ming-Yi, Yu-Ping Lin, Bei-Chang Yang, Yu-Song Jang, Chih-Kang Chiang, Clément Mettling, Zeng-Weng Chen, et al. "Catenarin Prevents Type 1 Diabetes in Nonobese Diabetic Mice via Inhibition of Leukocyte Migration Involving the MEK6/p38 and MEK7/JNK Pathways." Evidence-Based Complementary and Alternative Medicine 2012 (2012): 1–13. http://dx.doi.org/10.1155/2012/982396.

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Inflammation contributes to leukocyte migration, termed insulitis, andβ-cell loss in type 1 diabetes (T1D). Naturally occurring anthraquinones are claimed as anti-inflammatory compounds; however, their actions are not clear. This study aimed to investigate the effect and mechanism of catenarin on the inflammatory disease, T1D. Catenarin and/or its anthraquinone analogs dose-dependently suppressed C-X-C chemokine receptor type 4 (CXCR4)- and C-C chemokine receptor type 5 (CCR5)-implicated chemotaxis in leukocytes. Catenarin, the most potent anthraquinone tested in the study, prevented T1D in nonobese diabetic mice. Mechanistic study showed that catenarin did not act on the expression of CCR5 and CXCR4. On the contrary, catenarin inhibited CCR5- and CXCR4-mediated chemotaxis via the reduction of the phosphorylation of mitogen-activated protein kinases (p38 and JNK) and their upstream kinases (MKK6 and MKK7), and calcium mobilization. Overall, the data demonstrate the preventive effect and molecular mechanism of action of catenarin on T1D, suggesting its novel use as a prophylactic agent in T1D.

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ARININGSIH, IKA, SOLICHATUN SOLICHATUN, and ENDANG ANGGARWULAN. "Callus growth and anthraquinones production of Indian mulberry (Morinda citrifolia L.) in Murashige-Skoogâ€™s medium (MS) supplemented with Ca2+ and Cu2+." Biofarmasi Journal of Natural Product Biochemistry 1, no. 2 (August 7, 2003): 39–43. http://dx.doi.org/10.13057/biofar/f010201.

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The objectives of the research were to study the effect of Ca2+ and Cu2+ ions in Murashige-Skoogâ€™s medium on callus growth and anthraquinones production from Morinda citrifolia callus. The outline of the research was that the callus growth and secondary metabolite production from plantâ€™s body could be triggered by the occurrence of elicitor that is added to cultureâ€™s medium, as biotic or abiotic elicitors. The addition of Ca2+ and Cu2+ ions in cultureâ€™s medium as abiotic elicitor would cause the occurrence of metalâ€™s ion competition and interaction toward cells that being cultured, furthermore, it would influence ion transport from or to cell cytoplasm. Finally, cytoplasm pH would be influenced, so that both of callus growth and secondary metabolite from the cell that being cultured will also affected. In this research, in vitro callus culture method to obtain callus from explant (Morinda citrifolia leaf) and to induced anthraquinone production was used. In vitro culture used in this research consisted of 3 stages. First stage was the basal medium for sterilant object, second stage was the callus initiation medium to induce callus, and third stage was the treatment medium to induce anthraquinone production from callus. The research used factorial completely randomized design with 2 factors (Ca2+ ions: 0 mgl-1, 440 mgl-1, 880 mgl-1 and Cu2+ ions 0 mgl-1, 2,5 mgl-1, 5 mgl-1), with 3 replicates. Data collected were qualitative data (explant sterilization and callus morphology) and quantitative data (callus growth rate, callus dry weight, and anthraquinone content). The data were analyzed using ANOVA, followed by DMRT with 5% confidence level. The result of the research indicated that the treatment with addition of Ca2+ and Cu2+ ions on MS medium did not have any significant effect on callus growth and anthraquinone production.

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VONDRÁK, Jan, Jaroslav ŠOUN, Olga VONDRÁKOVແ, Alan M. FRYDAY, Alexander KHODOSOVTSEV, and Evgeny A. DAVYDOV. "Absence of anthraquinone pigments is paraphyletic and a phylogenetically unreliable character in the Teloschistaceae." Lichenologist 44, no. 3 (March 29, 2012): 401–18. http://dx.doi.org/10.1017/s0024282911000843.

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AbstractIt has been suggested that the absence of anthraquinones is not a synapomorphic character, but appears independently in unrelated lineages of Teloschistaceae. We analyzed ITS nrDNA regions in species of the genus Caloplaca and present evidence for five such examples: the Caloplaca cerina group, C. obscurella, the C. servitiana group, the C. xerica group and the C. variabilis group (Pyrenodesmia). In some cases, loss of anthraquinones is observed only in individuals within ordinarily pigmented populations, but sometimes the loss covers whole lineages containing one or more species. Both situations are observed in the C. servitiana group. Loss of anthraquinones is always followed by the synthesis of ‘alternative’ pigments (often Sedifolia-grey). In the specimens with anthraquinone-containing apothecia studied, these pigments are not visible in apothecial sections after dissolving anthraquinones in K. Fully unpigmented apothecia have not been observed.The Caloplaca xerica group is a newly established, infraspecific grouping of species related to, and similar to, C. xerica. The Caloplaca servitiana group is also newly established and represents an isolated lineage covering two rather different, but related species. Caloplaca neotaurica is described here as a new species with apothecia of two colour variants; orange-red (with anthraquinones) and grey (with Sedifolia-grey).The genus Huea represents another taxon lacking anthraquinones within Teloschistaceae. The genera Apatoplaca and Cephalophysis, which lack anthraquinones, are tentatively placed in Teloschistaceae, but their phylogenetic identity has not been recognized. Hueidea is reported to have no anthraquinones, but its secondary metabolites should be studied further and its possible placement in Teloschistaceae assessed.We suggest that Caloplaca abbreviata var. lecideoides and C. celata represent variants of C. stillicidiorum lacking anthraquinones.

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Zhang, Guoying, and Xiaofeng Chi. "A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water." Open Chemistry 18, no. 1 (June 23, 2020): 702–10. http://dx.doi.org/10.1515/chem-2020-0079.

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AbstractRheum tanguticum is a traditional Chinese herbal medicine, which contains abundant anthraquinones. In this study, anthraquinones were efficiently extracted from Rheum tanguticum by subcritical water extraction (SWE). The parameters of extraction time (33–67 min), temperature (100–200°C), and SW flow rate (1.4–4.6 mL/min) were optimized so as to achieve a high yield of the target product. A high yield of the total anthraquinones was achieved under the optimized SWE conditions of extraction time 54 min, extraction temperature 170°C, and the flow rate 2.0 mL/min. The comparison between the SWE and traditional extraction techniques implied that the SWE is an efficient and green alternative method for the extraction of anthraquinones. Four anthraquinone glycosides were purified from the SWE extract by high-speed counter-current chromatography and identified as emodin-1-O-β-D-glucoside, physcion-8-O-β-D-glucopyranoside, chrysophanol-1-O-β-D-glucoside, and chrysophanol-8-O-β-D-glucoside.

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Wong, Yee Ching, and Haziqah A. Razak. "EXTRACTION OF CRUDE ESSENTIAL FROM SENNA ALATA (POKOK GELENGGANG)." JOURNAL OF ADVANCES IN CHEMISTRY 11, no. 10 (December 17, 2016): 3794–806. http://dx.doi.org/10.24297/jac.v11i10.2179.

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Senna alata was one of the herbs plants that can be used to treat the ringworm in traditional method. In this study, the senna alata was scientifically tested to prove the traditional medicinal used. Six forms of extract were extracted by using soxhlet apparatus and continued with the appropriate methods that can extract the chemical compound of anthraquinone. The six forms of extraction included anthraquinone aglycone, anthraquinone glycoside, anthraquinone aglycone from glycoside, anthraquinone from crude absolute ethanol, anthraqunone from crude n-hexane and anthraquinone from crude ethanol 70%. The extraction of six forms of anthraquinone extract as antifungal was observed by tested with two types of fungi; Tricophyton rubrum and Microsporum gypseum. The extraction from crude absolute ethanol and crude n-hexane to inhibit these fungi were compared to determine which type of solvent was the best to use for inhibition. This test was implemented by using well-diffusion and broth microdilution method to determine the minimum inhibitory concentration (MIC). The present of six forms of anthraquinone was examined by using Thin-Layer Chromatography (TLC).

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Guin, Partha Sarathi, Piyal Das, Saurabh Das, and Parikshit Chandra Mandal. "Interaction of Calf Thymus DNA with the Ni(II) Complex of Sodium 1,4-Dihydroxy-9,10-Anthraquinone-2-Sulphonate: A Novel Method of Analysis Using Cyclic Voltammetry." International Journal of Electrochemistry 2012 (2012): 1–10. http://dx.doi.org/10.1155/2012/183745.

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Hydroxy-9,10-anthraquinones are cheaper alternatives to anthracycline drugs. They closely resemble anthracycline drugs both from a structural and functional viewpoint. Electrochemical behavior of the Ni(II) complex (Na2[Ni(NaLH)2Cl2]⋅2H2O) of sodium 1,4-dihydroxy-9,10-anthraquinone-2-sulphonate (NaLH2), analogue of the core unit of anthracycline anticancer drugs, was studied at physiological pH using cyclic voltammetry. The Ni(II) complex of sodium 1,4-dihydroxy-9,10-anthraquinone-2-sulphonate undergoes diffusion-controlled one-electron reduction that enables performing an electrochemical study on the interaction of the complex with calf thymus DNA. The complex was titrated with increasing concentrations of DNA, and the reduction peak for the unbound complex helped in evaluating binding parameters. Analysis of binding data using nonlinear curve fit in a cyclic voltammetry experiment is the first such attempt. The paper evaluates site size of interaction that also serves as a means to determine stoichiometry of complex formation, between a metal ion and ligand from a DNA interaction study, probably a first of its kind.

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50

Yang, Wen-Chin, Ming-Yi Shen, Yu-Song Jang, Zeng-Weng Chen, and Cicero Chang. "Catenarin, an anthraquinone compound, inhibits CXCR4 and CCR5 pathways to protect against type 1 diabetes in NOD mice (72.1)." Journal of Immunology 188, no. 1_Supplement (May 1, 2012): 72.1. http://dx.doi.org/10.4049/jimmunol.188.supp.72.1.

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Abstract Inflammation contributes to leukocyte migration, termed insulitis, and β cell loss in type 1 diabetes (T1D). Naturally occurring anthraquinones are claimed as anti-inflammatory compounds; however, their actions are not clear. This study aimed to investigate the effect and mechanism of catenarin on the inflammatory disease, T1D. Catenarin and/or its anthraquinone analogs dose-dependently suppressed C-X-C chemokine receptor type 4 (CXCR4)- and C-C chemokine receptor type 5 (CCR5)-implicated chemotaxis in leukocytes. Catenarin, the most potent anthraquinone tested in the study, prevented T1D in non-obese diabetic mice. Mechanistic study showed that catenarin did not act on the expression of CCR5 and CXCR4. On the contrary, catenarin inhibited CCR5- and CXCR4-mediated chemotaxis via the reduction of the phosphorylation of mitogen-activated protein kinases (p38 and JNK) and their upstream kinases (MKK6 and MKK7) and calcium mobilization. Overall, this study demonstrates the preventive effect and molecular mechanism of action of catenarin on T1D, suggesting its novel use as a prophylactic agent in T1D.

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Journal articles on the topic 'Anthraquinone'

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