Molecular networking-guided isolation of undescribed antifungal odoriferous sesquiterpenoids from a marine mesophotic zone sponge-associated Streptomyces sp. NBU3428

Huimin Wen; Dashuai Zhang; Hang Zhao; Yawen Zhang; Xiaojun Yan; Wenhan Lin; Shan He; Lijian Ding

doi:10.1016/j.phytochem.2023.113779

Molecular networking-guided isolation of undescribed antifungal odoriferous sesquiterpenoids from a marine mesophotic zone sponge-associated Streptomyces sp. NBU3428

Phytochemistry. 2023 Sep:213:113779. doi: 10.1016/j.phytochem.2023.113779. Epub 2023 Jun 25.

Authors

Huimin Wen¹, Dashuai Zhang², Hang Zhao², Yawen Zhang², Xiaojun Yan², Wenhan Lin³, Shan He⁴, Lijian Ding⁵

Affiliations

¹ Department of Marine Pharmacy, Ningbo University, Ningbo, 315211, China; Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Health Science Center, Ningbo University, Ningbo, 315211, China.
² Department of Marine Pharmacy, Ningbo University, Ningbo, 315211, China.
³ Ningbo Institute of Marine Medicine, Peking University, Ningbo, 315800, China.
⁴ Department of Marine Pharmacy, Ningbo University, Ningbo, 315211, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo, 315800, China. Electronic address: heshan@nbu.edu.cn.
⁵ Department of Marine Pharmacy, Ningbo University, Ningbo, 315211, China; Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Health Science Center, Ningbo University, Ningbo, 315211, China. Electronic address: dinglijian@nbu.edu.cn.

PMID: 37364708
DOI: 10.1016/j.phytochem.2023.113779

Abstract

Under the guidance of MS/MS-based molecular networking, eight odoriferous sesquiterpenes including two undescribed geosmin-type sesquiterpenoid degradations, odoripenoid A (1) and odoripenoid B (2), and two undescribed germacrane-type sesquiterpenoids, odoripenoid C (3) and odoripenoid (4), together with four known related compounds (5-8) were isolated from the EtOAc extract of the marine mesophotic zone sponge-associated Streptomyces sp. NBU3428. All chemical structures including absolute configurations of these compounds were elucidated by means of HRESIMS, NMR, ECD calculations and single-crystal X-ray diffraction experiments. Compounds 1 and 2 represent the rarely geosmin-related metabolites directly as natural products from actinomycetes. The isolated compounds (1-8) were assayed in a range of biological activities. Compounds 1 and 2 showed anti-Candida albicans activity with MIC values of 16 and 32 μg/mL, respectively, representing potential antifungal agents.

Keywords: Antifungal agents; Geosmin-type; Germacrane-type; Molecular networking; Sesquiterpenoid; Sponge-associated; Streptomyces.

MeSH terms

Antifungal Agents
Molecular Structure
Sesquiterpenes* / chemistry
Streptomyces* / chemistry
Streptomyces* / metabolism
Tandem Mass Spectrometry

Substances

Antifungal Agents
geosmin
Sesquiterpenes