Journal Article

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

Luo, Lian-Xiang, Qi, Shu-Hua, Zhong, Lin-Fang, Yang, Chang-Nian, Liang, Xiao, Ling, Juan

2023

Overview

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.

• Publisher: MDPI AG
• Subject: Adenocarcinoma / Alkaloids / antibacterial / Antibacterial activity / antibacterial properties / Antibiotics / cell lines / Circular dichroism / circular dichroism spectroscopy / Cytotoxicity / Dichroism / Fungi / Lecanicillium / Lecanicillium kalimantanense / Lung cancer / lungs / mangrove sediment-derived fungus / Mangroves / neoplasm cells / Oxidation / Pathogens / Pesticides / Quantum chemistry / quantum mechanics / Sediment / Single crystals / spectral analysis / structure-activity relationships / thiodiketopiperazine-class alkaloid / X-ray diffraction / X-ray diffraction analysis