Reverse‐phase high pressure liquid chromatographic analysis of hydroxycoumarins in plant extracts. Quantitative determination of hydroxycoumarins in <i>Fraxinus ornus</i>

Nykolov, Nykolay; Iossifova, Tanya; Vassileva, Elka; Kostova, I.; Stoev, G.

doi:10.1002/pca.2800040207

Cited by 22 publications

(8 citation statements)

References 3 publications

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“…2) due to loss of a hexose unit (AM, 162.2), thus confirming the proposed structure from 'H-NMR data. Until now, 7-methyl esculin had only been detected in Fraxinus ornus (ash tree, Oleaceae) where it is one of the minor constituents of the bark (Nykolov et al 1993).…”

Section: Resultsmentioning

confidence: 99%

Patterns of phenolic compounds in leafy galls of tobacco

Vereecke

Messens

Klarskov

et al. 1997

Planta

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The chemical composition of ethanolic and aqueous extracts from leafy galls produced after infection of Nicotiana tabacum L. plants with Rhodococcus fascians was drastically changed compared to uninfected controls. Chlorogenic acid was abundant both in uninfected and infected plants, but caffeic acid and another cinnamoyl analogue were new in leafy galls. The most pronounced product induced in leafy galls was identified as 7-O-methyl-6-O-beta-D-glucopyranosyl coumarin (7-methyl esculin). This is the first report of the presence of this coumarin derivative in tobacco. Interestingly, 7-methyl esculin did not accumulate in the presence of avirulent R. fascians strains nor was it found in leafy galls on other plant species. However, it did appear in crown galls induced by Agrobacterium tumefaciens on tobacco plants. Intriguingly, none of the phenolics known to accumulate in Solanaceae under pathogen attack were found in leafy galls. 7-Methyl esculin barely affected growth of R. fascians nor was it catabolized. Microscopical analysis showed that autofluorescent compounds were located mainly in the abundant meristematic regions of the leafy galls. We postulate that 7-methyl esculin might locally influence plant cell division.

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Section: Resultsmentioning

confidence: 99%

Patterns of phenolic compounds in leafy galls of tobacco

Vereecke

Messens

Klarskov

et al. 1997

Planta

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“…The amount of fraxin is much higher than that of fraxetin, usually by an order of magnitude. 5) A previous study reported that fraxin (fraxetin-7-O-¢glucosidase) could be primarily hydrolyzed to fraxetin by intestinal microflora extensively, after oral administration of fraxin in rats. This finding suggested that the aglycone of fraxin (fraxetin) rather than fraxin itself was the major constituent in the circulating system after administration of fraxin-containing herbals, and also implied that the in vivo pharmaceutical effects of fraxin might be attributable to fraxetin or its constitutive metabolite(s).…”

Section: Introductionmentioning

confidence: 99%

Identification and Characterization of Human UDP-glucuronosyltransferases Responsible for the Glucuronidation of Fraxetin

Xia

Liang

Zhu

et al. 2014

Drug Metabolism and Pharmacokinetics

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Fraxetin, a major constituent of the traditional medicine plant Fraxinus rhynchophylla Hance (Oleaceae), has been found to possess multiple bioactivities. However, the metabolic pathway(s) of fraxetin in human tissues has not been reported yet. This study aimed to characterize the glucuronidation pathway(s) of fraxetin in human tissues. Fraxetin could be metabolized to two glucuronides in human liver microsomes (HLMs). These two glucuronides were biosynthesized and characterized as 7-O-glucuronide (7-O-G) and 8-O-glucuronide (8-O-G). UGT1A1, -1A6, -1A7, -1A8, -1A9 and -1A10 participated in the formation of 7-O-G, while the formation of 8-O-G was catalyzed selectively by UGT1A6 and UGT1A9. UGT1A9 showed the highest catalytic activities in the formation of 7-O-G and 8-O-G. Both kinetic characterization and inhibition assays demonstrated that UGT1A9 played important roles in fraxetin glucuronidations in HLMs, especially in the formation of the major metabolite 8-O-G. Furthermore, the intrinsic clearance of fraxetin in both human liver microsomes and UGT1A9 was greater than that of 7,8-dihydroxylcoumarin, revealing that the addition of a C-6 methoxy group led to the higher metabolic clearance. In summary, the glucuronidation pathways of fraxetin in human liver microsomes were well-characterized, and UGT1A9 was the major isoform responsible for the glucuronidations of fraxetin.

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“…SU, Fraxinus japonica BLUME ex K. KOCH, Fraxinus floribunda WALL, Fraxinus mandshurica RUPR., Fraxinus ornus L., and Fraxinus rhynchophylla. [5][6][7]9,[16][17][18][19][20][21][22] By reverse-phase high-performance liquid chromatography (RP-HPLC) analysis, fraxetin was identified to account for 0.04%-0.07% in Bulgarian Fraxinus ornus barks. [6] The peak area of fraxetin in the RP-HPLC profile of Aesculus hippocastanum L. bark methanol extract was 8.28%.…”

Section: Natural Occurrencementioning

confidence: 99%

Health benefits of fraxetin: From chemistry to medicine

Ha,

Son

2024

Archiv der Pharmazie

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Fraxetin is a bioactive molecule present in various natural plants, especially Cortex Fraxini. Evidenced outcomes in phytochemical and biological analyses for this agent are now available in the literature, but an insightful review is yet unknown. The goal of the current research is to offer a panoramic illustration of natural observation, biosynthesis, synthesis, pharmacology, and pharmacokinetics for fraxetin. Esculetin and ferulic acid acted as precursors in the enzymatic biosynthetic route, whereas fraxetin could be easily synthesized from simple phenols. A great deal of interest was obtained in using this molecule for pharmacological targets. Herein, its pharmacological value included anticancer, antioxidative, anti‐inflammatory, antidiabetic, antiobesity, and antimicrobial activities, as well as the protection of the liver, neurons, heart, bone, lung, kidney, and others. Anticancer activity may involve the inhibition of proliferation, invasion, and migration, together with apoptotic induction. Health benefits from this molecule were deduced from its ability to suppress cytokines and protect the immune syndrome. Various signaling pathways, such as Janus kinase 2 (JAK2)/signal transducer and activator of transcription 3 (STAT3), phosphoinositide 3 kinase (PI3K)/protein kinase B (Akt), nuclear factor kappa B (NF‐κB)/NLRP3, Akt/AMPK, have been proposed for in vitro and in vivo mechanisms of action. Fraxetin is highly distributed to rat plasma and several organs. However, more pharmacokinetic studies to improve its bioavailability are needed since its solubility in water is still limited.

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Reverse‐phase high pressure liquid chromatographic analysis of hydroxycoumarins in plant extracts. Quantitative determination of hydroxycoumarins in Fraxinus ornus

Cited by 22 publications

References 3 publications

Patterns of phenolic compounds in leafy galls of tobacco

Patterns of phenolic compounds in leafy galls of tobacco

Identification and Characterization of Human UDP-glucuronosyltransferases Responsible for the Glucuronidation of Fraxetin

Health benefits of fraxetin: From chemistry to medicine

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