Cryptochinones from Cryptocarya chinensis act as farnesoid X receptor agonists

Lin, Hsiang‐Ru; Chou, Tsung-Hsien; Huang, Din-Wen; Chen, Ih-Sheng

doi:10.1016/j.bmcl.2014.07.045

Cited by 14 publications

(15 citation statements)

References 23 publications

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“…is an endemic famous for its antioxidant, immunological, and antitumor effects in southern China, Japan, and Taiwan. Four naturally occurring tetrahydroflavanone cryptochinones A–D (179–182), obtained from this plant, transactivated FXR dose dependently in a transient transfection reporter assay, semblable to CDCA ( Lin et al, 2014 ). Xanthohumol (124) is not only a counteractor of LXRs activation, but also an FXR modulator.…”

Section: Natural Products Targeting Farnesoid X Receptormentioning

confidence: 99%

Natural Products Targeting Liver X Receptors or Farnesoid X Receptor

She

Pang

et al. 2022

Front. Pharmacol.

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Nuclear receptors (NRs) are a superfamily of transcription factors induced by ligands and also function as integrators of hormonal and nutritional signals. Among NRs, the liver X receptors (LXRs) and farnesoid X receptor (FXR) have been of significance as targets for the treatment of metabolic syndrome-related diseases. In recent years, natural products targeting LXRs and FXR have received remarkable interests as a valuable source of novel ligands encompassing diverse chemical structures and bioactive properties. This review aims to survey natural products, originating from terrestrial plants and microorganisms, marine organisms, and marine-derived microorganisms, which could influence LXRs and FXR. In the recent two decades (2000–2020), 261 natural products were discovered from natural resources such as LXRs/FXR modulators, 109 agonists and 38 antagonists targeting LXRs, and 72 agonists and 55 antagonists targeting FXR. The docking evaluation of desired natural products targeted LXRs/FXR is finally discussed. This comprehensive overview will provide a reference for future study of novel LXRs and FXR agonists and antagonists to target human diseases, and attract an increasing number of professional scholars majoring in pharmacy and biology with more in-depth discussion.

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Section: Natural Products Targeting Farnesoid X Receptormentioning

confidence: 99%

Natural Products Targeting Liver X Receptors or Farnesoid X Receptor

She

Pang

et al. 2022

Front. Pharmacol.

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“…Its aglycone naringenin has been shown to be a partial agonist of LXRα in cells transfected with a reporter construct [74]. In contrast, using computer modelling of tetrahydro-flavanones (cryptochinones A–D), it was shown that flavanones may behave as FXR agonists to decrease CYP7A1 mRNA expression [76]. The only one study that investigated the effects of flavones from a leaf extract of Xanthosoma sagittifolium showed no effects on total Bas, but reduced secondary BAs in rats [77,78].…”

Section: Current Status Of Knowledge: Polyphenols That Regulate Bimentioning

confidence: 99%

Polyphenol Effects on Cholesterol Metabolism via Bile Acid Biosynthesis, CYP7A1: A Review

et al. 2019

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Atherosclerosis, the main contributor to coronary heart disease, is characterised by an accumulation of lipids such as cholesterol in the arterial wall. Reverse cholesterol transport (RCT) reduces cholesterol via its conversion into bile acids (BAs). During RCT in non-hepatic peripheral tissues, cholesterol is transferred to high-density lipoprotein (HDL) particles and returned to the liver for conversion into BAs predominantly via the rate-limiting enzyme, cholesterol 7 α-hydroxylase (CYP7A1). Numerous reports have described that polyphenol induced increases in BA excretion and corresponding reductions in total and LDL cholesterol in animal and in-vitro studies, but the process whereby this occurs has not been extensively reviewed. There are three main mechanisms by which BA excretion can be augmented: (1) increased expression of CYP7A1; (2) reduced expression of intestinal BA transporters; and (3) changes in the gut microbiota. Here we summarise the BA metabolic pathways focusing on CYP7A1, how its gene is regulated via transcription factors, diurnal rhythms, and microRNAs. Importantly, we will address the following questions: (1) Can polyphenols enhance BA secretion by modulating the CYP7A1 biosynthetic pathway? (2) Can polyphenols alter the BA pool via changes in the gut microbiota? (3) Which polyphenols are the most promising candidates for future research? We conclude that while in rodents some polyphenols induce CYP7A1 expression predominantly by the LXRα pathway, in human cells, this may occur through FXR, NF-KB, and ERK signalling. Additionally, gut microbiota is important for the de-conjugation and excretion of BAs. Puerarin, resveratrol, and quercetin are promising candidates for further research in this area.

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“…As a part of the Madagascar International Cooperative Biodiversity Group (ICBG) program, 3 an EtOH extract of the root wood of Cryptocarya rigidifolia (Lauraceae) was selected for bioassay-directed fractionation because of its reproducible activity against Plasmodium falciparum Dd2 (IC 50 ∼5 μg/mL). The genus Cryptocarya is distributed throughout the tropic, subtropic, and temperate regions of the world, and its members produce an array of secondary metabolites including flavonoids such as cryptochinones, 4 which have recently been shown to act as farnesoid X receptor agonists, 5 alkaloids, 6 and a variety of 5,6-dihydro-α-pyrones, 7 − 12 some of which have the ability to stabilize the tumor suppressor PDCD4. 13 Other Cryptocarya -derived α-pyrones display antiparasitic, 14 antimycobacterial, 14 antitumor, 15 and anticancer activities.…”

mentioning

confidence: 99%

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1

et al. 2015

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Antimalarial bioassay-guided fractionation of an EtOH extract of the root wood of Cryptocarya rigidifolia (Lauraceae) led to the isolation of the five new 5,6-dihydro-α-pyrones cryptorigidifoliols A–E (1–5) and the six bicyclic tetrahydro-α-pyrone derivatives cryptorigidifoliols F–K (6–11). The structure elucidations of all compounds were made on the basis of the interpretation of spectroscopic data and chemical derivatization, and the relative and absolute configurations were determined by NOESY, electronic circular dichroism (ECD), and 1H NMR analysis of α-methoxyphenylacetyl (MPA) derivatives. The bicyclic tetrahydro-α-pyrone derivatives were identified as products of acid-catalyzed intramolecular Michael addition of the 5,6-dihydro-α-pyrones in the presence of silica gel. A structure–activity relationship study suggested that the presence of an α,β-unsaturated carbonyl moiety is not essential for potent antimalarial activity.

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Cryptochinones from Cryptocarya chinensis act as farnesoid X receptor agonists

Cited by 14 publications

References 23 publications

Natural Products Targeting Liver X Receptors or Farnesoid X Receptor

Natural Products Targeting Liver X Receptors or Farnesoid X Receptor

Polyphenol Effects on Cholesterol Metabolism via Bile Acid Biosynthesis, CYP7A1: A Review

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1

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