来自植物内生真菌污色拟盘多毛孢的抗真菌单萜衍生物

Antifungal Monoterpene Derivatives from the Plant Endophytic Fungus Pestalotiopsis foedan.

作者信息

Xu Dan, Zhang Bing-Yang, Yang Xiao-Long

机构信息

Innovative Drug Research Centre, Chongqing University (Huxi Campus), Chongqing, 401331, P. R. China.

College of Pharmaceutical Science, Hebei University, Baoding, 071002, P. R. China.

出版信息

Chem Biodivers. 2016 Oct;13(10):1422-1425. doi: 10.1002/cbdv.201600114.

DOI:10.1002/cbdv.201600114

PMID:27448166

Abstract

A new monoterpene lactone, (1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (1), along with one related known compound, (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propanoic acid (2), were isolated from the liquid culture of the plant endophytic fungus Pestalotiopsis foedan obtained from the branch of Bruguiera sexangula. The structure and absolute configuration of 1 were determined on the basis of extensive analysis of NMR spectra combined with computational methods via calculation of the optical rotation (OR) and C-NMR. Both compounds exhibited strong antifungal activities against Botrytis cinerea and Phytophthora nicotianae with MIC values of 3.1 and 6.3 μg/ml, respectively, which are comparable to those of the known antifungal drug ketoconazole. Compound 2 also showed modest antifungal activity against Candida albicans with a MIC value of 50 μg/ml.

摘要

从采自木榄枝条的植物内生真菌污色拟盘多毛孢（Pestalotiopsis foedan）的液体培养物中分离得到一个新的单萜内酯，即(1R,4R,5R,8S)-8-羟基-4,8-二甲基-2-氧杂双环[3.3.1]壬烷-3-酮（1），以及一个相关已知化合物，即(2R)-2-[(1R)-4-甲基环己-3-烯-1-基]丙酸（2）。通过对核磁共振谱进行广泛分析，并结合计算方法，经旋光（OR）计算和碳核磁共振确定了1的结构和绝对构型。这两种化合物对灰葡萄孢（Botrytis cinerea）和烟草疫霉（Phytophthora nicotianae）均表现出较强的抗真菌活性，其最低抑菌浓度（MIC）值分别为3.1和6.3 μg/ml，与已知抗真菌药物酮康唑相当。化合物2对白色念珠菌（Candida albicans）也表现出一定的抗真菌活性，MIC值为50 μg/ml。