Journal articles: 'Anthraquinones'

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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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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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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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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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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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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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7

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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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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10

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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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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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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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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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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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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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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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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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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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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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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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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23

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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24

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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25

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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26

Sadiq, Uzma, Harsharn Gill, and Jayani Chandrapala. "Temperature and pH Stability of Anthraquinones from Native Aloe vera Gel, Spray-Dried and Freeze-Dried Aloe vera Powders during Storage." Foods 11, no. 11 (May 30, 2022): 1613. http://dx.doi.org/10.3390/foods11111613.

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The present study explored the stability of extracted anthraquinones (aloin, aloe-emodin and rhein) from whole-leaf Aloe vera gel (WLAG), its freeze-dried powder (FDP) and spray-dried powder (SDP) under varying pH and temperature conditions during storage. Each anthraquinone behaved differently under different processing parameters. The amount of anthraquinones present in the gel was higher than in FDP and SDP. The aloin contents decreased by more than 50% at 50 °C and 70 °C, while at 25 °C and 4 °C, the decrease was moderate. A substantial reduction in aloin concentration was noticed at pH 6.7, whereas it remained unaffected at pH 3.5. The temperature and pH had no significant effect on the stability of aloe-emodin. Interestingly, a small quantity of rhein was detected during storage due to the oxidative degradation of aloin into aloe-emodin and rhein. These findings can provide significant insight into retaining anthraquinones during processing while developing functional foods and nutraceuticals to obtain maximum health benefits.

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27

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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28

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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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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30

Aladejana, Elizabeth Bosede, and Collen Musara. "Kniphofia foliosa Hochst, (Asphodelaceae)." Journal of Pharmacy and Nutrition Sciences 11 (June 2, 2021): 13–19. http://dx.doi.org/10.29169/1927-5951.2021.11.02.

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This review gives the first comprehensive appraisal of Kniphofia foliosa Hochst, from the plant family Asphodelaceae: its botany, ethnomedicinal (with particular emphasis on the African communities), phytochemistry, and pharmacological potential. Particular emphasis is given to the biological and chemical properties. Peer review and literature search were done by conducting a logical and inclusive review. Indigenous cultures have used the plant among different ethnic groups in tropical Africa for medicinal and other purposes. The chemical compounds that have been isolated from K. foliosa include monomeric anthraquinones such as chrysophanol, islandicin, laccaic acid, aloe-emodin, and aloe-emodin acetate, which contain antileukaemic properties; dimeric anthraquinones such as asphodelin, knipholone, and chryslandicin; phenyl anthraquinones and anthrones, including knipholone anthrone, isoknipholone anthrone, knipholone, phenylanthrone knipholone anthrone and anthraquinone isoknipholone; oxanthrones such as isofoliosone and foliosone; and rare dimeric phenylanthraqunones joziknipholones A and B. The pharmacological studies on K. foliosa exhibited antimalarial, antioxidant, antibacterial, anti-HIV-1, and anti-leukotriene activities. From the above, it can be deduced that K. foliosa contains chemical constituents of pharmacological importance, contributing significantly to the development of new medicines.

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31

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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32

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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33

Li, Xun, Shifeng Chu, Yinjiao Liu, and Naihong Chen. "Neuroprotective Effects of Anthraquinones from Rhubarb in Central Nervous System Diseases." Evidence-Based Complementary and Alternative Medicine 2019 (May 16, 2019): 1–12. http://dx.doi.org/10.1155/2019/3790728.

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Rhubarb is a well-known traditional Chinese medicine; it has been used in China for thousands of years. Rhubarb anthraquinones are the major medicinal ingredients derived from rhubarb including emodin, aloe-emodin, chrysophanol, rhein, physcion, and danthron. These different anthraquinone derivatives alone or in combination play a therapeutic role in central nervous system diseases (CNSD), such as cerebral ischemic stroke, intracerebral hemorrhage, traumatic brain injury, brain tumor, Alzheimer’s disease, depression, and others. We review the experimental studies on these six anthraquinones in the treatment of CNSD by consulting literature published in the last 20 years in PubMed and then give a future perspective on it. In the end of this paper some deficiencies related to these studies also have been pointed out.

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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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35

Oktavia, Listiana, Evana Evana, Reza Fahardita, and Andria Agusta. "Optimization of Bis-anthraquinones Production from Endophytic Fungi Diaporthe sp. GNBP-10." Iraqi Journal of Pharmaceutical Sciences ( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512) 32, no. 1 (June 16, 2023): 160–66. http://dx.doi.org/10.31351/vol32iss1pp160-166.

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Bis-anthraquinones with a unique molecular backbone, (+)-2,2’-epicytoskyrin A (epi) and (+)-1,1′-bislunatin (bis), was produced by endophytic fungi Diaporthe sp GNBP-10 associated with Gambir plant (Uncaria gambier). Epi and bis possess robust antimicrobial activity toward various pathogens. This study focus on knowing the optimum condition of epi and bis production from Diaporthe sp GNBP-10. A series of culture media with various nutrient compositions was investigated in epi and bis production. The content of epi and bis was determined by measuring the area under the curve from TLC-densitometric (scanner) experiment. The linear regression analysis was then applied to obtain the results. The optimized epi and bis production was observed in liquid media 3 containing potato starch and dextrose with the amount of epi produced is 0.484mg while bis content is 0.163mg. The presence of carbohydrates, whether simple sugar or carbohydrate complex, plays an essential role in the bis-anthraquinones production from Diaphorthe sp culture. The presence of minerals and excessive protein sources did not significantly affect bis-anthraquinones production. Keywords: bis-anthraquinone, Diaporthe sp, culture media, regression, TLC scanner

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36

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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37

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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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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39

Fain, V. Ya, B. E. Zaitsev, and M. A. Ryabov. "Anthraquinones tautomerism: VII. Hydroxy-substituted anthraquinones." Russian Journal of Organic Chemistry 43, no. 10 (October 2007): 1460–65. http://dx.doi.org/10.1134/s1070428007100089.

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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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41

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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Sottorff, Ignacio, Sven Künzel, Jutta Wiese, Matthias Lipfert, Nils Preußke, Frank Sönnichsen, and Johannes Imhoff. "Antitumor Anthraquinones from an Easter Island Sea Anemone: Animal or Bacterial Origin?" Marine Drugs 17, no. 3 (March 5, 2019): 154. http://dx.doi.org/10.3390/md17030154.

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The presence of two known anthraquinones, Lupinacidin A and Galvaquinone B, which have antitumor activity, has been identified in the sea anemone (Gyractis sesere) from Easter Island. So far, these anthraquinones have been characterized from terrestrial and marine Actinobacteria only. In order to identify the anthraquinones producer, we isolated Actinobacteria associated with the sea anemone and obtained representatives of seven actinobacterial genera. Studies of cultures of these bacteria by HPLC, NMR, and HRLCMS analyses showed that the producer of Lupinacidin A and Galvaquinone B indeed was one of the isolated Actinobacteria. The producer strain, SN26_14.1, was identified as a representative of the genus Verrucosispora. Genome analysis supported the biosynthetic potential to the production of these compounds by this strain. This study adds Verrucosispora as a new genus to the anthraquinone producers, in addition to well-known species of Streptomyces and Micromonospora. By a cultivation-based approach, the responsibility of symbionts of a marine invertebrate for the production of complex natural products found within the animal’s extracts could be demonstrated. This finding re-opens the debate about the producers of secondary metabolites in sea animals. Finally, it provides valuable information about the chemistry of bacteria harbored in the geographically-isolated and almost unstudied, Easter Island.

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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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Berenbeim, J. A., S. Boldissar, S. Owens, M. R. Haggmark, G. Gate, F. M. Siouri, T. Cohen, M. F. Rode, C. Schmidt Patterson, and M. S. de Vries. "Excited state intramolecular proton transfer in hydroxyanthraquinones: Toward predicting fading of organic red colorants in art." Science Advances 5, no. 9 (September 2019): eaaw5227. http://dx.doi.org/10.1126/sciadv.aaw5227.

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Compositionally similar organic red colorants in the anthraquinone family, whose photodegradation can cause irreversible color and stability changes, have long been used in works of art. Different organic reds, and their multiple chromophores, suffer degradation disparately. Understanding the details of these molecules’ degradation therefore provides a window into their behavior in works of art and may assist the development of improved conservation methods. According to one proposed model of photodegradation dynamics, intramolecular proton transfer provides a kinetically favored decay pathway in some photoexcited chromophores, preventing degradation-promoting electron transfer (ET). To further test this model, we measured excited state lifetimes of substituted gas-phase anthraquinones using high-level theory to explain the experimental results. The data show a general structural trend: Anthraquinones with 1,4-OH substitution are long-lived and prone to damaging ET, while excited state intramolecular proton transfers promote efficient quenching for hydroxyanthraquinones that lack this motif.

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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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Reyes-Chilpa, Ricardo, Rocío Gómez-Cansino, Silvia Laura Guzmán-Gutiérrez, Simón Hernández-Ortega, María Campos-Lara, Elisa Vega-Avila, and Antonio Nieto-Camacho. "Anthraquinones from Vismia mexicana." Zeitschrift für Naturforschung C 69, no. 1-2 (February 1, 2014): 29–34. http://dx.doi.org/10.5560/znc.2013-0038.

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Vismia mexicana (Clusiaceae) is a small tropical tree found from Mexico to Honduras. The CH2Cl2=MeOH extract from the leaves has been reported to have inhibitory properties against reverse transcriptase of human immunodeficiency virus type 1 (HIV-1 RT). In order to characterize some of its chemical constituents, the EtOAc-soluble fraction of this extract was subjected to column chromatography. A new natural product was isolated and designated vismiaquinone D [1-hydroxy-6- methoxy-7,8-(3',3'-dimethyl-pyrano) anthraquinone]. In addition, vismiaquinone was obtained. The structures of vismiaquinone and vismiaquinone D were determined by 1H and 13C NMR spectroscopy, unambiguous assignments were achieved with DEPT, HSQC, and HMBC experiments, and corroborated by X-ray diffraction studies. The isolated anthraquinones were tested against HIV-1 RT. However, none showed relevant activity, suggesting that other compounds in this extract may be responsible for its HIV-1 RT inhibitory properties.

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Amorim, Juliana, Viviana Vásquez, Andrea Cabrera, Maritza Martínez, and Juan Carpio. "In Silico and In Vitro Identification of 1,8-Dihydroxy-4,5-dinitroanthraquinone as a New Antibacterial Agent against Staphylococcus aureus and Enterococcus faecalis." Molecules 29, no. 1 (December 29, 2023): 203. http://dx.doi.org/10.3390/molecules29010203.

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Increasing rates of bacterial resistance to antibiotics are a growing concern worldwide. The search for potential new antibiotics has included several natural products such as anthraquinones. However, comparatively less attention has been given to anthraquinones that exhibit functional groups that are uncommon in nature. In this work, 114 anthraquinones were evaluated using in silico methods to identify inhibitors of the enzyme phosphopantetheine adenylyltransferase (PPAT) of Staphylococcus aureus, Enterococcus faecalis, and Escherichia coli. Virtual screenings based on molecular docking and the pharmacophore model, molecular dynamics simulations, and free energy calculations pointed to 1,8-dihydroxy-4,5-dinitroanthraquinone (DHDNA) as the most promising inhibitor. In addition, these analyses highlighted the contribution of the nitro group to the affinity of this anthraquinone for the nucleotide-binding site of PPAT. Furthermore, DHDNA was active in vitro towards Gram-positive bacteria with minimum inhibitory concentration (MIC) values of 31.25 µg/mL for S. aureus and 62.5 µg/mL for E. faecalis against both antibiotic-resistant isolates and reference strains but was ineffective against E. coli. Experiments on kill-time kinetics indicated that, at the tested concentrations, DHDNA produced bacteriostatic effects on both Gram-positive bacteria. Overall, our results present DHDNA as a potential PPAT inhibitor, showing antibacterial activity against antibiotic-resistant isolates of S. aureus and E. faecalis, findings that point to nitro groups as key to explaining these results.

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Tadesse, Asnakew Amare, Negera Abdissa Ayana, and Dele Abdissa Keneni. "Anthraquinones from the Roots of Kniphofia insignis and Evaluation of Their Antimicrobial Activities." Journal of Chemistry 2021 (April 14, 2021): 1–5. http://dx.doi.org/10.1155/2021/6661116.

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Sequential extraction using a cold maceration method and column chromatographic separation of the roots Kniphofia insignis headed to the isolation of three anthraquinones: one monomeric anthraquinone (1) and two dimeric anthraquinones (2 and 3). It was further purified by Sephadex LH-20 and recrystallized. The structures of these compounds were established based on the spectroscopic analyses including NMR (1H-NMR and 13C-NMR and infrared) and comparison with reported literatures. In an in vitro antimicrobial assay of the crude extracts, the isolated compounds were made against four bacterial strains (S. aureus ATCC 25923, B. subtilis ATCC 6633, E. coli ATCC 35218, and P. aeruginosa ATCC 27853) and Fusarium spp. fungal strain. In the crude extracts of chloroform, substantial antimicrobial activity was seen with the highest activity against B. subtilis (16 mm) and E. coli (22 mm). Meanwhile, compound 1 has a better zone of inhibition with 14 mm against P. aeruginosa, whereas compound 2 showed better activity (13 mm) against Fusarium spp. fungal strain.

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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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Greco, Giulia, Eleonora Turrini, Elena Catanzaro, and Carmela Fimognari. "Marine Anthraquinones: Pharmacological and Toxicological Issues." Marine Drugs 19, no. 5 (May 13, 2021): 272. http://dx.doi.org/10.3390/md19050272.

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The marine ecosystem, populated by a myriad of animals, plants, and microorganisms, is an inexhaustible reservoir of pharmacologically active molecules. Among the multiple secondary metabolites produced by marine sources, there are anthraquinones and their derivatives. Besides being mainly known to be produced by terrestrial species, even marine organisms and the uncountable kingdom of marine microorganisms biosynthesize anthraquinones. Anthraquinones possess many different biological activities, including a remarkable antitumor activity. However, due to their peculiar chemical structures, anthraquinones are often associated with toxicological issues, even relevant, such as genotoxicity and mutagenicity. The aim of this review is to critically describe the anticancer potential of anthraquinones derived from marine sources and their genotoxic and mutagenic potential. Marine-derived anthraquinones show a promising anticancer potential, although clinical studies are missing. Additionally, an in-depth investigation of their toxicological profile is needed before advocating anthraquinones as a therapeutic armamentarium in the oncological area.

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Journal articles on the topic 'Anthraquinones'

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