Seven drimane-type sesquiterpenoids from an earwig-associated Aspergillus sp

Khan Salman; Hongjie Zhu; Ziqian Sun; Yilin Li; Lan Wang; Rong Wang; Zhikai Guo; Ruihua Jiao

doi:10.1016/S1875-5364(23)60385-1

Seven drimane-type sesquiterpenoids from an earwig-associated Aspergillus sp

Chin J Nat Med. 2023 Jan;21(1):58-64. doi: 10.1016/S1875-5364(23)60385-1.

Authors

Khan Salman¹, Hongjie Zhu¹, Ziqian Sun¹, Yilin Li², Lan Wang¹, Rong Wang³, Zhikai Guo⁴, Ruihua Jiao⁵

Affiliations

¹ State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, School of Life Sciences, Nanjing University, Nanjing 210093, China.
² Key Laboratory for Biology and Genetic Resources of Tropical Crops of Hainan Province, Hainan Institute for Tropical Agricultural Resources, Haikou 571101, China; Hainan Academy of Ocean and Fisheries Sciences, Hainan Tropical Ocean University, Haikou 571126, China.
³ Hainan Academy of Ocean and Fisheries Sciences, Hainan Tropical Ocean University, Haikou 571126, China.
⁴ Hainan Key Laboratory of Tropical Microbe Resources, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China; Key Laboratory for Biology and Genetic Resources of Tropical Crops of Hainan Province, Hainan Institute for Tropical Agricultural Resources, Haikou 571101, China. Electronic address: guozhikai@itbb.org.cn.
⁵ State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, School of Life Sciences, Nanjing University, Nanjing 210093, China. Electronic address: rhjiao@nju.edu.cn.

PMID: 36641233
DOI: 10.1016/S1875-5364(23)60385-1

Abstract

Drimane-type sesquiterpenoids are widely distributed in fungi. From the ethyl acetate extract of the earwig-derived Aspergillus sp. NF2396, seven new drimane-type sesquiterpenoids, named drimanenoids A-G (1-7), were isolated. Their structures were elucidated by diverse spectroscopic analysis including high-resolution ESI-MS, one- and two-dimensional NMR spectroscopy. Drimanenoids A-F (1-6) are new members of drimane-type sesquiterpenoid esterified with unsaturated fatty acid side chain at C-6. Drimanenoids C (3), D (4) and F (6) showed antibacterial activity against five types of bacteria with different inhibition diameters. Drimanenoid D (4) exhibited moderate cytotoxicity against human myelogenous leukemia cell line K562 with an IC₅₀ value of 12.88 ± 0.11 μmol·L^-1.

Keywords: Antibacterial; Aspergillus sp.; Cytotoxic; Drimane-type; Fungus; Sesquiterpenoids.

MeSH terms

Aspergillus / chemistry
Humans
Magnetic Resonance Spectroscopy
Molecular Structure
Polycyclic Sesquiterpenes
Sesquiterpenes* / chemistry

Substances

drimane
Polycyclic Sesquiterpenes
Sesquiterpenes