青霉 DJJ-1 中具有抗菌活性的聚酮化合物。

Polyketides with antimicrobial activities from Penicillium canescens DJJ-1.

机构信息

Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China; Yunnan Provincial Key Laboratory of Entomological Biopharmaceutical R&D, College of Pharmacy, Dali University, Dali, Yunnan, China.

出版信息

Phytochemistry. 2023 Feb;206:113554. doi: 10.1016/j.phytochem.2022.113554. Epub 2022 Dec 7.

DOI:10.1016/j.phytochem.2022.113554

PMID:36496005

Abstract

Two undescribed polyketides canecines A-B, one unreported cyclopentenone canecine C, together with 12 known compounds were isolated from an extract of the fungus Penicillium canescens DJJ-1. Their structures were elucidated by detailed analysis of spectroscopic data, NMR calculations with dJ-DP4 or DP4+, and their absolute configurations were further determined by quantum chemical calculations of ECD spectra or X-crystallography. Canecine A was a grisan polyketide featuring a dimethyltetrahydro-4H-furo[2,3-b]pyran. Canecine A exhibited significant inhibitory activity against Candida albicans with an MIC value of 1 μg/mL and showed inhibitory effect on nitric oxide production in LPS-activated RAW264.7 macrophages. These results enrich the structural diversities of polyketides from endophytic fungi.

摘要

从真菌青霉菌 DJJ-1 的提取物中分离得到两种未描述的聚酮类化合物 canecines A-B、一种未报道的环戊烯酮 canecine C 以及 12 种已知化合物。通过详细的光谱数据分析、NMR 计算（包括 dJ-DP4 或 DP4+），以及通过量子化学计算 ECD 光谱或 X 晶体学确定它们的绝对构型，阐明了它们的结构。Canecine A 是一种 grisan 聚酮类化合物，具有二甲基四氢-4H-呋喃[2,3-b]吡喃。Canecine A 对白色念珠菌具有显著的抑制活性，MIC 值为 1μg/mL，并对 LPS 激活的 RAW264.7 巨噬细胞中的一氧化氮生成具有抑制作用。这些结果丰富了内生真菌来源的聚酮类化合物的结构多样性。