A novel polycyclic quinazoline and three quinolines alkaloids from marine-derived fungus trichoderma longibrachiatum QD01 with anti-bacterial and anti-quorum sensing activities

紫红色杆菌 群体感应 喹啉 立体化学 化学 生物碱 喹唑啉 有机化学 生物化学 毒力 基因
作者
Chaoyi Lv,Zhizhou Li,Shaohua Sun,Jiaying Ma,Hui Wang,Hu Zhu,Shiwei Sun,Wei Wang
出处
期刊:Natural Product Research [Informa]
卷期号:: 1-10
标识
DOI:10.1080/14786419.2024.2341277
摘要

A novel polycyclic quinazoline alkaloid (1) along with one new natural quinoline alkaloid (2) and two known quinoline alkaloids (3,4) were isolated from the marine-derived fungus Trichoderma longibrachiatum QD01. Structural determinations of those isolates were established by comprehensive spectroscopic analyses and literature comparison. Single-crystal X-ray diffraction analysis of novel compound verified its structure and stereochemistry, representing the first characterised crystal structure of a trimeric-type of tetrahydroquinazoline. Compound 4 exhibited potential antibacterial and anti-quorum sensing activity against C. violaceum and C. violaceum CV026. The sub-MIC of 4 observably decreased the violacein production in C. violaceum CV026 by 55% on 15 μg/mL. Furthermore, molecular docking results revealed that 4 has stronger binding interactions with CviR receptor than ligand C6-HSL with lower binding energy of −8.68 kcal/mol. Hydrogen bond and π–π interactions formed by Trp84, Tyr88, Trp111, and Phe126 were predicted to play an important role in the inhibition against C. violaceum CV026.
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