Dataset Information

Thiodiketopiperazines Produced by Penicillium crustosum and Their Activities to Promote Gastrointestinal Motility.

ABSTRACT: Three new thiodiketopiperazines (1?3), along with two known analogues (4 and 5), were isolated from the fermentation broth of Penicillium crustosum. Their structures were elucidated through extensive spectroscopic analysis and the absolute configurations of new compounds were determined by Mosher ester analysis and calculated ECD spectra. Compound 4 and 5 have the activity to promote the gastrointestinal motility of zebrafish via acting on the cholinergic nervous system.

SUBMITTER: He X

PROVIDER: S-EPMC6359346 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Thiodiketopiperazines Produced by Penicillium crustosum and Their Activities to Promote Gastrointestinal Motility.

He Xin X Yang Jing J Qiu Ling L Feng Dan D Ju Feng F Tan Lu L Li Yu-Zhi YZ Gu Yu-Cheng YC Zhang Zhen Z Guo Da-Le DL Deng Yun Y

Molecules (Basel, Switzerland) 20190115 2

Three new thiodiketopiperazines (1⁻3), along with two known analogues (4 and 5), were isolated from the fermentation broth of Penicillium crustosum. Their structures were elucidated through extensive spectroscopic analysis and the absolute configurations of new compounds were determined by Mosher ester analysis and calculated ECD spectra. Compound 4 and 5 have the activity to promote the gastrointestinal motility of zebrafish via acting on the cho ...[more]

PMID: 30650614

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Project description:Endophytic fungi are symbiotic with plants and possess multienzyme systems showing promising metabolite potency with region selectivity and stereoselectivity. The aim of this study was to use these special microorganisms as an in vitro model to mimic the potential mammalian metabolites of a natural iridoid gentiopicroside (GPS, compound 1). The fungi isolated from a medicinal plant, Dendrobium candidum Wall. ex Lindl., were screened for their biotransformation abilities with GPS as the substrate, and one strain with high converting potency was identified as Penicillium crustosum 2T01Y01 on the basis of the sequence of the internal transcribed spacer of the ribosomal DNA region. Upon the optimized incubation of P. crustosum 2T01Y01 with the substrate, seven deglycosylated metabolites were detected by ultraperformance liquid chromatography/quadrupole time of flight mass spectrometry (UPLC/Q-TOF MS). Preparative-scale biotransformation with whole cells of the endophytic fungus resulted in the production of five metabolites, including three novel ones, 5α-(hydroxymethyl)-6β-methyl-3,4,5,6-tetrahydropyrano[3,4-c]pyran-1(8H)-one (compound 2), (Z)-4-(1-hydroxybut-3-en-2-yl)-5,6-dihydropyran-2-one (compound 3), and (E)-4-(1-hydroxybut-3-en-2-yl)-5,6-dihydropyran-2-one (compound 4), along with two known ones, 5α-(hydroxymethyl)-6β-methyl-1H,3H-5,6-dihydropyrano[3,4-c]pyran-1(3H)-one (compound 5) and 5α-(hydroxymethyl)-6α-methyl-5,6-dihydropyrano[3,4-c]pyran-1(3H)-one (compound 6), aided by nuclear magnetic resonance and high-resolution mass spectral analyses. The other two metabolites were tentatively identified by online UPLC/Q-TOF MS as 5-hydroxymethyl-5,6-dihydroisochromen-1-one (compound 7) and 5-hydroxymethyl-3,4,5,6-tetrahydroisochromen-1-one (compound 8), and compound 8 is a new metabolite. To test the metabolic mechanism, the β-glucosidase activity of the fungus P. crustosum 2T01Y01 was assayed with ρ-nitrophenyl-β-d-glucopyranoside as a probe substrate, and the pathway of GPS biotransformation by strain 2T01Y01 is proposed. In addition, the hepatoprotective activities of GPS and metabolite compounds 2, 5, and 6 against human hepatocyte line HL-7702 injury induced by hydrogen peroxide were evaluated.

Dataset Information

Thiodiketopiperazines Produced by Penicillium crustosum and Their Activities to Promote Gastrointestinal Motility.

Publications

Thiodiketopiperazines Produced by <i>Penicillium crustosum</i> and Their Activities to Promote Gastrointestinal Motility.

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