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[PMID]: | 27237303 | [Au] Autor: | Fan HX; Zhou ZQ; Peng J; Wu BJ; Chen HR; Bao XF; Mu ZQ; Jiao WH; Yao XS; Gao H |
[Ad] Address: | a Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou , P.R. China. | [Ti] Title: | A microbial model of mammalian metabolism: biotransformation of 4,5-dimethoxyl-canthin-6-one using Cunninghamella blakesleeana CGMCC 3.970. | [So] Source: | Xenobiotica;47(4):284-289, 2017 Apr. | [Is] ISSN: | 1366-5928 | [Cp] Country of publication: | England | [La] Language: | eng | [Ab] Abstract: | 1. A filamentous fungus, Cunninghamella blakesleeana CGMCC 3.970, was applied as a microbial system to mimic mammalian metabolism of 4,5-dimethoxyl-canthin-6-one (1). Compound 1 belongs to canthin-6-one type alkaloids, which is a major bioactive constituent of a traditional Chinese medicine (the stems of Picrasma quassioides). 2. After 72 h of incubation in potato dextrose broth, 1 was metabolized to seven metabolites as follows: 4-methoxyl-5-hydroxyl-canthin-6-one (M1), 4-hydroxyl-5-methoxyl-canthin-6-one (M2), canthin-6-one (M3), canthin-6-one N-oxide (M4), 10-hydroxyl-4,5-dimethoxyl-canthin-6-one (M5), 1-methoxycarbonl-ß-carboline (M6), and 4-methoxyl-5-O-ß-D-glucopyranosyl-canthin-6-one (M7). 3. The structures of metabolites were determined using spectroscopic analyses, chemical methods, and comparison of NMR data with those of known compounds. Among them, M7 was a new compound. 4. The metabolic pathways of 1 were proposed, and the metabolic processes involved phase I (O-demethylation, dehydroxylation, demethoxylation, N-oxidation, hydroxylation, and oxidative ring cleavage) and phase II (glycosylation) reactions. 5. This was the first research on microbial transformation of canthin-6-one alkaloid, which could be a useful microbial model for producing the mammalian phase I and phase II metabolites of canthin-6-one alkaloids. 6. 1, M1-M5, and M7 are canthin-6-one alkaloids, whereas M6 belongs to ß-carboline type alkaloids. The strain of Cunninghamella blakesleeana can supply an approach to transform canthin-6-one type alkaloids into ß-carboline type alkaloids. |
[Mh] MeSH terms primary: |
Biotransformation Carbolines/metabolism Cunninghamella/metabolism Indole Alkaloids/metabolism
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[Pt] Publication type: | JOURNAL ARTICLE | [Nm] Name of substance: | 0 (Carbolines); 0 (Indole Alkaloids); 3FK17S759N (canthin-6-one) | [Em] Entry month: | 1707 | [Cu] Class update date: |
171116 | [Lr] Last revision date: | 171116 | [Js] Journal subset: | IM | [Da] Date of entry for processing: | 160531 | [St] Status: | MEDLINE |
[do] DOI: | 10.1080/00498254.2016.1184774 |
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