Investigations of specialised metabolites of endophyte Diaporthe destruens hosted in Illigera orbiculata C. Y. Wu

Sheng-Qi Zhang; Jia-Peng Wang; Feng-Mei Zhang; Lin-Lin Yao; Bing-Xian Li; Ya-Ni Li; Dong Gan; Rui-Feng Mei; Le Cai; Zhong-Tao Ding

doi:10.1016/j.phytochem.2022.113357

Investigations of specialised metabolites of endophyte Diaporthe destruens hosted in Illigera orbiculata C. Y. Wu

Phytochemistry. 2022 Nov:203:113357. doi: 10.1016/j.phytochem.2022.113357. Epub 2022 Aug 13.

Authors

Affiliations

¹ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China.
² College of Pharmacy, Dali University, Dali, 671003, People's Republic of China.
³ R&D Center of China Tobacco Yunnan Industry Co., Ltd., Kunming, 650231, People's Republic of China.
⁴ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China. Electronic address: caile@ynu.edu.cn.
⁵ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China; College of Pharmacy, Dali University, Dali, 671003, People's Republic of China. Electronic address: ztding@ynu.edu.cn.

PMID: 35970436
DOI: 10.1016/j.phytochem.2022.113357

Abstract

A chemical investigation of the endophytic fungus Diaporthe destruens from the Hernandiaceae plant Illigera orbiculata C. Y. Wu collected from southern Yunnan Province, China, led to the isolation of six undescribed compounds, including two azaphilone analogs, which are a pair of epimers (13R-hydroxy-chermesinone A and 13S-hydroxy-chermesinone A); a pyrrole derivative (1-(4-(methoxymethyl)-1H-pyrrol-3-yl)ethan-1-one); an isoindolone derivative (4-hydroxy-6-methoxyisoindolin-1-one); a benzylbenzene derivative (destruensine A) and a conjectural fragment of polyketide ((2R,4R)-2-(methoxymethyl)pentane-1,4-diol) along with nine known compounds. Their structures were elucidated by spectroscopic methods and HRESIMS, and the absolute configurations were further confirmed by electronic circular dichroism (ECD) and chemical derivatization. The antimicrobial activities, anti-acetylcholinesterase activities, antiproliferation, and NO production inhibitory effects of compounds 1-15 were evaluated.

Keywords: Diaporthaceae; Diaporthe destruens; Hernandiaceae; Illigera orbiculata C. Y. Wu; endophyte; specialised metabolites.

MeSH terms

Anti-Infective Agents* / metabolism
China
Endophytes
Hernandiaceae* / chemistry
Molecular Structure
Pentanes / metabolism
Polyketides*
Pyrroles / metabolism

Substances

Anti-Infective Agents
Pentanes
Polyketides
Pyrroles