Protoilludane-type sesquiterpenoids from Armillaria sp. by co-culture with the endophytic fungus Epicoccumsp. associated with Gastrodia elata

Hong-Tao Li; Lin-Huan Tang; Tao Liu; Rui-Ning Yang; Ya-Bin Yang; Hao Zhou; Zhong-Tao Ding

doi:10.1016/j.bioorg.2019.103503

Protoilludane-type sesquiterpenoids from Armillaria sp. by co-culture with the endophytic fungus Epicoccumsp. associated with Gastrodia elata

Bioorg Chem. 2020 Jan:95:103503. doi: 10.1016/j.bioorg.2019.103503. Epub 2019 Dec 10.

Authors

Hong-Tao Li¹, Lin-Huan Tang¹, Tao Liu¹, Rui-Ning Yang¹, Ya-Bin Yang¹, Hao Zhou², Zhong-Tao Ding³

Affiliations

¹ Key Laboratory of Functional Molecules Analysis and Biotransformation 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, China.
² Key Laboratory of Functional Molecules Analysis and Biotransformation 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, China. Electronic address: haozhou@ynu.edu.cn.
³ Key Laboratory of Functional Molecules Analysis and Biotransformation 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, China. Electronic address: ztding@ynu.edu.cn.

PMID: 31855825
DOI: 10.1016/j.bioorg.2019.103503

Abstract

An investigation of a co-culture of the Armillaria sp. and endophytic fungus Epicoccum sp. YUD17002 associated with Gastrodia elata led to the isolation of eight new compounds, including five protoilludane-type sesquiterpenes (1-5) and three aryl esters (6-8), together with six known analogues (9-14). The assignments of their structures were conducted via extensive analyses of the spectroscopic data and comparison of experimental and calculatedelectronic circular dichroism(ECD)data. Notably, these new compounds were not present in the pure culture controls and were only detected in the co-cultures. Compound 4 is the first example of an ent-protoilludane sesquiterpenoid scaffold bearing a five-membered lactone. Compound 6 exhibited moderate in vitro cytotoxic activities against five human cancer cell lines (HL-60, A549, MCF-7, SMMC-7721, and SW480) with IC₅₀ values ranging from 15.80 to 23.03 μM. Moreover, 6 showed weak acetylcholinesterase inhibitory activity (IC₅₀ value of 23.85 μM).

Keywords: Armillaria sp.; Co-culture; Cytotoxicity; Epicoccum sp.; Secondary metabolite; Sesquiterpenoid.

Publication types

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

MeSH terms

Acetylcholinesterase / metabolism
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Armillaria / chemistry*
Ascomycota / chemistry*
Cell Proliferation / drug effects
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / isolation & purification
Cholinesterase Inhibitors / pharmacology*
Coculture Techniques*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Gastrodia / chemistry*
Humans
Molecular Structure
Polycyclic Sesquiterpenes / chemistry
Polycyclic Sesquiterpenes / isolation & purification
Polycyclic Sesquiterpenes / pharmacology*
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Antineoplastic Agents, Phytogenic
Cholinesterase Inhibitors
Polycyclic Sesquiterpenes
protoilludane
Acetylcholinesterase