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Lecanicilliums A–F, Thiodiketopiperazine-Class Alkaloids from a Mangrove Sediment-Derived Fungus Lecanicillium kalimantanense

Authors :
Lin-Fang Zhong
Juan Ling
Lian-Xiang Luo
Chang-Nian Yang
Xiao Liang
Shu-Hua Qi
Source :
Marine Drugs, Vol 21, Iss 11, p 575 (2023)
Publication Year :
2023
Publisher :
MDPI AG, 2023.

Abstract

Six new thiodiketopiperazine-class alkaloids lecanicilliums A–F were isolated from the mangrove sediment-derived fungus Lecanicillium kalimantanense SCSIO41702, together with thirteen known analogues. Their structures were determined by spectroscopic analysis. The absolute configurations were determined by quantum chemical calculations. Electronic circular dichroism (ECD) spectra and the structure of Lecanicillium C were further confirmed by a single-crystal X-ray diffraction analysis. Lecanicillium A contained an unprecedented 6/5/6/5/7/6 cyclic system with a spirocyclic center at C-2′. Biologically, lecanicillium E, emethacin B, and versicolor A displayed significant cytotoxicity against human lung adenocarcinoma cell line H1975, with IC50 values of 7.2~16.9 μM, and lecanicillium E also showed antibacterial activity against four pathogens with MIC values of 10~40 μg/mL. Their structure–activity relationship is also discussed.

Details

Language :
English
ISSN :
16603397
Volume :
21
Issue :
11
Database :
Directory of Open Access Journals
Journal :
Marine Drugs
Publication Type :
Academic Journal
Accession number :
edsdoj.0ff99814223b472da22ed4a18c8508d8
Document Type :
article
Full Text :
https://doi.org/10.3390/md21110575