Three new diterpenes and two new sesquiterpenoids from the endophytic fungus Trichoderma koningiopsis A729

Shanchong Chen; Haohua Li; Yuchan Chen; Saini Li; Jianlin Xu; Heng Guo; Zhaoming Liu; Shuang Zhu; Hongxin Liu; Weimin Zhang

doi:10.1016/j.bioorg.2019.02.005

Three new diterpenes and two new sesquiterpenoids from the endophytic fungus Trichoderma koningiopsis A729

Bioorg Chem. 2019 May:86:368-374. doi: 10.1016/j.bioorg.2019.02.005. Epub 2019 Feb 5.

Authors

Shanchong Chen¹, Haohua Li², Yuchan Chen², Saini Li², Jianlin Xu¹, Heng Guo¹, Zhaoming Liu², Shuang Zhu³, Hongxin Liu⁴, Weimin Zhang⁵

Affiliations

¹ State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China; School of Biosciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, China.
² State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.
³ School of Biosciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, China.
⁴ State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China. Electronic address: liuhx@gdim.cn.
⁵ State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China. Electronic address: wmzhang@gdim.cn.

PMID: 30759407
DOI: 10.1016/j.bioorg.2019.02.005

Abstract

Three new diterpenes koninginols A-C (1-3) and two new sesquiterpenoids 11-hydroxy-15-drimeneoic acid (4), koninginol D (5), together with twelve known compounds (6-17) were isolated from the endophytic fungus Trichoderma koningiopsis A729 derived from Morinda officinalis. Their structures were fully assigned with the aid of extensive spectroscopic analysis and reported data from the previous literatures. Koninginols A and B were disclosed as intriguing diterpene alkaloids, whereas the koninginol C was disclosed as one of the two examples of harziandione diterpene. All the isolates were evaluated for their antitumor activity, and compounds 1-2, 4-6, 11-13, 16-17 were evaluated for their antibacterial activity, wherein the new compounds 1 and 2 exhibited significant antibacterial activity against Bacillus subtilis with MIC values of 10 and 2 μg/mL, respectively.

Keywords: Antibacterial activity; Diterpenes; Sesquiterpenoids; Trichoderma koningiopsis.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Bacillus subtilis / drug effects*
Cell Proliferation / drug effects
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Microbial Sensitivity Tests
Molecular Structure
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Structure-Activity Relationship
Trichoderma / chemistry*
Tumor Cells, Cultured

Substances

Anti-Bacterial Agents
Antineoplastic Agents
Diterpenes
Sesquiterpenes