The chemical diversity, the attractant, anti-acetylcholinesterase, and antifungal activities of metabolites from biocontrol Trichoderma harzianum uncovered by OSMAC strategy

Xue-Yin Wang; Ting-Ting Xu; Li-Jingfei Sun; Rong-Huan Cen; Shuang Su; Xue-Qiong Yang; Ya-Bin Yang; Zhong-Tao Ding

doi:10.1016/j.bioorg.2021.105148

The chemical diversity, the attractant, anti-acetylcholinesterase, and antifungal activities of metabolites from biocontrol Trichoderma harzianum uncovered by OSMAC strategy

Bioorg Chem. 2021 Sep:114:105148. doi: 10.1016/j.bioorg.2021.105148. Epub 2021 Jul 6.

Authors

Xue-Yin Wang¹, Ting-Ting Xu¹, Li-Jingfei Sun¹, Rong-Huan Cen¹, Shuang Su¹, Xue-Qiong Yang¹, Ya-Bin Yang², Zhong-Tao Ding³

Affiliations

¹ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, 2nd Cuihu North Road, Kunming 650091, China.
² Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, 2nd Cuihu North Road, Kunming 650091, China. Electronic address: ybyang@ynu.edu.cn.
³ Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, 2nd Cuihu North Road, Kunming 650091, China. Electronic address: ztding@ynu.edu.cn.

PMID: 34246973
DOI: 10.1016/j.bioorg.2021.105148

Abstract

Eight new compounds (1-8) were discovered from Trichoderma harzianum associated with edible mushroom by the one strain many compounds (OSMAC) strategy. Triharzianin A (1) is the first naturally scaffold characterized by a C₁₃-prostaglandin skeleton. The configurations of 1-3, and 5 were determined by the Mosher's method, experimental and calculated ECD spectra, and plausible biosynthesis of stereospecific epoxidation. Most compounds indicated obvious feeding attractant activities to silkworm with attraction rates at 30-90%. Compound 7 showed anti-acetylcholinesterase (anti-AChE) activity with a ratio of 29% at a concentration of 50 μM for insecticidal potential. So 2,3-dialkylchromone (7) had potential of chemical entrapment and killing of insects. Compounds 2, 3 and 7-11 showed antifungal activities against Aspergillus fumigates, and Trichoderma sp. from mushroom with MICs ≤ 300 μM. The four fermentation extracts also indicated obvious feeding attractant activities to silkworm for the activities brought by active metabolites from T. harzianum. The material base of biocontrol induced by the interaction of host-fungal symbiont can be investigated by the antifungal metabolites against pathogen fungi.

Keywords: Anti-acetylcholinesterase activity; Antifungal activity; Entrapment and kill; Feeding attractant; Metabolite; OSMAC; Trichoderma harzianum.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / metabolism*
Animals
Antifungal Agents / chemistry
Antifungal Agents / metabolism
Antifungal Agents / pharmacology*
Aspergillus fumigatus / drug effects*
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / metabolism
Cholinesterase Inhibitors / pharmacology*
Density Functional Theory
Dose-Response Relationship, Drug
Microbial Sensitivity Tests
Molecular Structure
Structure-Activity Relationship
Trichoderma / chemistry*
Trichoderma / drug effects*

Substances

Antifungal Agents
Cholinesterase Inhibitors
Acetylcholinesterase