Terpenoids from the endophytic fungus Microdiplodia sp. and their anti-inflammatory activities

Yufang Bi; Yihu Yu; Houzong Yao; Tao Yuan

doi:10.1016/j.fitote.2023.105711

Terpenoids from the endophytic fungus Microdiplodia sp. and their anti-inflammatory activities

Fitoterapia. 2023 Dec:171:105711. doi: 10.1016/j.fitote.2023.105711. Epub 2023 Oct 20.

Authors

Yufang Bi¹, Yihu Yu², Houzong Yao³, Tao Yuan⁴

Affiliations

¹ The Laboratory of Effective Substances of Jiangxi Genuine Medicinal Materials, College of Life Sciences, Jiangxi Normal University, Nanchang 330022, China; College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.
² The Laboratory of Effective Substances of Jiangxi Genuine Medicinal Materials, College of Life Sciences, Jiangxi Normal University, Nanchang 330022, China.
³ School of Health, Jiangxi Normal University, Nanchang 330022, China.
⁴ The Laboratory of Effective Substances of Jiangxi Genuine Medicinal Materials, College of Life Sciences, Jiangxi Normal University, Nanchang 330022, China; School of Health, Jiangxi Normal University, Nanchang 330022, China. Electronic address: tyuan@jxnu.edu.cn.

PMID: 37866425
DOI: 10.1016/j.fitote.2023.105711

Abstract

Motivated by the potential anti-inflammatory effect of the crude extract of endophytic fungus Microdiplodia sp. CJ01 derived from Camellia sinensis, chemical investigation of the extract of Microdiplodia sp. CJ01 led to the isolation and identification of sixteen terpenoids, including five undescribed eremophilane sesquiterpenoids named microdiplodins A-E (1-5), one undescribed meroterpenoid 13-carboxymacrophorin A (13), seven known eremophilane sesquiterpenoids (6-12), and three known meroterpenoids (14-16). The structures of these compounds were elucidated based on extensive spectroscopic analysis, including nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. Their absolute configurations were determined by calculational and experimental electronic circular dichroism (ECD) data. Anti-inflammatory activity assays revealed that compounds 3, 4, 14-16 exhibited moderate inhibitory effects on the production of nitric oxide (NO) in the lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells.

Keywords: Eremophilane sesquiterpenoid; Meroterpenoid; Microdiplodia sp.; Microdiplodins; Nitric oxide production.

MeSH terms

Anti-Inflammatory Agents
Ascomycota* / chemistry
Circular Dichroism
Molecular Structure
Polycyclic Sesquiterpenes
Sesquiterpenes*
Terpenes / chemistry
Terpenes / pharmacology

Substances

Terpenes
Sesquiterpenes
Polycyclic Sesquiterpenes
Anti-Inflammatory Agents