Lithocarols A-F, six tenellone derivatives from the deep-sea derived fungus Phomopsis lithocarpus FS508

Jianlin Xu; Zhaoming Liu; Yuchan Chen; Haibo Tan; Haohua Li; Saini Li; Heng Guo; Zilei Huang; Xiaoxia Gao; Hongxin Liu; Weimin Zhang

doi:10.1016/j.bioorg.2019.03.078

Lithocarols A-F, six tenellone derivatives from the deep-sea derived fungus Phomopsis lithocarpus FS508

Bioorg Chem. 2019 Jun:87:728-735. doi: 10.1016/j.bioorg.2019.03.078. Epub 2019 Apr 1.

Authors

Jianlin Xu¹, Zhaoming Liu², Yuchan Chen², Haibo Tan³, Haohua Li², Saini Li², Heng Guo¹, Zilei Huang², Xiaoxia Gao⁴, Hongxin Liu⁵, Weimin Zhang⁶

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; College of Pharmacy, 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 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China.
⁴ College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China.
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: liuhx@gdim.cn.
⁶ 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: 30954837
DOI: 10.1016/j.bioorg.2019.03.078

Abstract

Lithocarols A-F (1-6) possessing novel highly-oxygenated isobenzofuran core, together with a related known compound isoprenylisobenzofuran A (7) were isolated from the marine-derived fungus Phomopsis lithocarpus FS508. Among them, lithocarols A-E (1-5) represent the first examples of poly-ketal derivatives in tenellone family. The structures for all these compounds were fully elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism calculations. Their cytotoxic assay disclosed that compounds 1-4 displayed moderate growth inhibitory effect against four human tumor cell lines with the IC₅₀ values ranging from 10.5 to 38.7 μM.

Keywords: Cytotoxicity; Deep-sea derived fungus; Lithocarols; Phomopsis lithocarpus; Tenellone derivatives.

Publication types

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

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Ascomycota / chemistry*
Benzofurans / chemistry
Benzofurans / isolation & purification
Benzofurans / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Crystallography, X-Ray
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Models, Molecular
Molecular Structure
Structure-Activity Relationship

Substances

Antineoplastic Agents
Benzofurans
benzofuran