Cyophiobiolins A-D, ophiobolin sestertepenoids from Cytospora rhizophorae

Yanjiang Zhang; Hongxin Liu; Yuchan Chen; Xiuxiang Lu; Zhaoming Liu; Haibo Tan; Weimin Zhang

doi:10.1016/j.phytochem.2022.113352

Cyophiobiolins A-D, ophiobolin sestertepenoids from Cytospora rhizophorae

Phytochemistry. 2022 Nov:203:113352. doi: 10.1016/j.phytochem.2022.113352. Epub 2022 Aug 18.

Authors

Yanjiang Zhang¹, Hongxin Liu², Yuchan Chen², Xiuxiang Lu¹, Zhaoming Liu², Haibo Tan³, Weimin Zhang²

Affiliations

¹ Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, 510650, China; University of Chinese Academy of Sciences, Beijing, 100049, China.
² State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou, 510070, China.
³ Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, 510650, China; University of Chinese Academy of Sciences, Beijing, 100049, China. Electronic address: tanhaibo@scbg.ac.cn.

PMID: 35988743
DOI: 10.1016/j.phytochem.2022.113352

Abstract

Cyophiobiolins A-D, four unreported ophiobolin-type sesterterpenoids, were isolated from Cytospora rhizophorae A761, an endophytic fungus from Gynochthodes officinalis. The structures of these undescribed compounds were fully characterized on the basis of extensively spectroscopic data (1D, 2D NMR and HRESIMS) and single-crystal X-ray diffraction analyses. Moreover, cyophiobiolins A-D were evaluated for in vitro cytotoxic, anti-inflammatory, and antibacterial activities. Cyophiobiolins A-B showed inhibitory potency against lipopolysaccharide (LPS)-induced oxide production with IC₅₀ values of 66.3 μM and 53.3 μM, respectively.

Keywords: Anti-inflammatory activity; Cyophiobiolins; Cytospora rhizophorae; Endophytic fungus; Gynochthodes officinalis; Rubiaceae; Valsaceae.

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology
Anti-Inflammatory Agents / chemistry
Ascomycota* / chemistry
Lipopolysaccharides* / pharmacology
Molecular Structure
Oxides
Sesterterpenes

Substances

Anti-Bacterial Agents
Anti-Inflammatory Agents
Lipopolysaccharides
Oxides
Sesterterpenes
ophiobolins

Supplementary concepts

Cytospora rhizophorae