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Main Authors:	Ren, Shuya, Yan, Yan, Zhou, Yuran, Han, Yanhong, Yuan, Siwen, Chen, Junjie, Guo, Heng, Lin, Zhenjian, Lin, Qifeng, Chen, Senhua, Liu, Lan, Qiao, Yongkang, Gao, Zhizeng
Format:	Artículo científico
Language:	en
Published:	Bioorganic chemistry 2025
Subjects:	Animals Molecular Structure Indolequinones Urochordata Humans Ascomycota Dose-Response Relationship, Drug Structure-Activity Relationship Aspergillus oryzae Biological Products
Online Access:	https://pubmed.ncbi.nlm.nih.gov/39742673/
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author	Ren, Shuya Yan, Yan Zhou, Yuran Han, Yanhong Yuan, Siwen Chen, Junjie Guo, Heng Lin, Zhenjian Lin, Qifeng Chen, Senhua Liu, Lan Qiao, Yongkang Gao, Zhizeng
author_facet	Ren, Shuya Yan, Yan Zhou, Yuran Han, Yanhong Yuan, Siwen Chen, Junjie Guo, Heng Lin, Zhenjian Lin, Qifeng Chen, Senhua Liu, Lan Qiao, Yongkang Gao, Zhizeng Ren, Shuya Yan, Yan Zhou, Yuran Han, Yanhong Yuan, Siwen Chen, Junjie Guo, Heng Lin, Zhenjian Lin, Qifeng Chen, Senhua Liu, Lan Qiao, Yongkang Gao, Zhizeng
collection	PubMed - marine biology
contents	Genome mining of nonenzymatic ortho-quinone methide-based pseudonatural products from ascidian-derived fungus Diaporthe sp.SYSU-MS4722. Ren, Shuya Yan, Yan Zhou, Yuran Han, Yanhong Yuan, Siwen Chen, Junjie Guo, Heng Lin, Zhenjian Lin, Qifeng Chen, Senhua Liu, Lan Qiao, Yongkang Gao, Zhizeng Animals Molecular Structure Indolequinones Urochordata Humans Ascomycota Dose-Response Relationship, Drug Structure-Activity Relationship Aspergillus oryzae Biological Products Ortho-quinone methides (o-QMs), generated by oxidative dehydration of clavatol, are highly reactive intermediates in biosynthesis that give rise to a variety of clavatol-containing pseudonatural products (PNPs) in fungi through intra- and intermolecular nonenzymatic cyclization/addition reaction, and some compounds have significant biological activities. Here we report our genome mining efforts on a cryptic clavatol biosynthetic gene cluster (BGC) from an ascidian-derived fungus Diaporthe sp. SYSU-MS4722. The core genes NR-PKS (DiaG), Esterase (DiaF) derived from the fungus Diaporthe sp. SYSU-MS4722 clavatol BGC and the known α-ketoglutarate-dependent nonheme iron enzymes (ClaD) were heterologously expressed in the Aspergillus oryzae NSAR1 (A. oryzae NSAR1). Thirteen new monomeric, dimeric, and trimeric clavatol-based PNPs (7-19), together with three known compounds (20-22) were isolated from the above transformant. Their structures including absolute configurations were elucidated by spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR data), complemented with the X-ray crystallography, the comparison of the experimental and calculated ECD spectra, and gauge-independent atomic orbital (GIAO) NMR calculations. Based on the structural characteristics, their plausible biosynthetic pathways were proposed. Notably, Compounds 8, 9, 14 and 16 exhibited potent anti-fibrotic activity with EC values of 28.9, 10.0, 3.5 and 30.1 μM, respectively.
format	Artículo científico
id	pubmed_39742673
institution	PubMed
language	en
publishDate	2025
publisher	Bioorganic chemistry
record_format	pubmed
spellingShingle	Genome mining of nonenzymatic ortho-quinone methide-based pseudonatural products from ascidian-derived fungus Diaporthe sp.SYSU-MS4722. Ren, Shuya Yan, Yan Zhou, Yuran Han, Yanhong Yuan, Siwen Chen, Junjie Guo, Heng Lin, Zhenjian Lin, Qifeng Chen, Senhua Liu, Lan Qiao, Yongkang Gao, Zhizeng Animals Molecular Structure Indolequinones Urochordata Humans Ascomycota Dose-Response Relationship, Drug Structure-Activity Relationship Aspergillus oryzae Biological Products Genome mining of nonenzymatic ortho-quinone methide-based pseudonatural products from ascidian-derived fungus Diaporthe sp.SYSU-MS4722. Ren, Shuya Yan, Yan Zhou, Yuran Han, Yanhong Yuan, Siwen Chen, Junjie Guo, Heng Lin, Zhenjian Lin, Qifeng Chen, Senhua Liu, Lan Qiao, Yongkang Gao, Zhizeng Animals Molecular Structure Indolequinones Urochordata Humans Ascomycota Dose-Response Relationship, Drug Structure-Activity Relationship Aspergillus oryzae Biological Products Ortho-quinone methides (o-QMs), generated by oxidative dehydration of clavatol, are highly reactive intermediates in biosynthesis that give rise to a variety of clavatol-containing pseudonatural products (PNPs) in fungi through intra- and intermolecular nonenzymatic cyclization/addition reaction, and some compounds have significant biological activities. Here we report our genome mining efforts on a cryptic clavatol biosynthetic gene cluster (BGC) from an ascidian-derived fungus Diaporthe sp. SYSU-MS4722. The core genes NR-PKS (DiaG), Esterase (DiaF) derived from the fungus Diaporthe sp. SYSU-MS4722 clavatol BGC and the known α-ketoglutarate-dependent nonheme iron enzymes (ClaD) were heterologously expressed in the Aspergillus oryzae NSAR1 (A. oryzae NSAR1). Thirteen new monomeric, dimeric, and trimeric clavatol-based PNPs (7-19), together with three known compounds (20-22) were isolated from the above transformant. Their structures including absolute configurations were elucidated by spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR data), complemented with the X-ray crystallography, the comparison of the experimental and calculated ECD spectra, and gauge-independent atomic orbital (GIAO) NMR calculations. Based on the structural characteristics, their plausible biosynthetic pathways were proposed. Notably, Compounds 8, 9, 14 and 16 exhibited potent anti-fibrotic activity with EC values of 28.9, 10.0, 3.5 and 30.1 μM, respectively.
title	Genome mining of nonenzymatic ortho-quinone methide-based pseudonatural products from ascidian-derived fungus Diaporthe sp.SYSU-MS4722.
topic	Animals Molecular Structure Indolequinones Urochordata Humans Ascomycota Dose-Response Relationship, Drug Structure-Activity Relationship Aspergillus oryzae Biological Products
url	https://pubmed.ncbi.nlm.nih.gov/39742673/

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