Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum.
A novel chaetoglobosin named penochalasin I (1) with a unprecedented six-cyclic 6/5/6/5/6/13 fused ring system, and another new chaetoglobosin named penochalasin J (2), along with chaetoglobosins G, F, C, A, E, armochaetoglobosin I, and cytoglobosin C (3-9) were isolated from the culture ofPenicillium chrysogenumV11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds1and2were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound1was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2' of the chaetoglobosin class. Compounds5-8remarkably inhibited the plant pathogenic fungusR. solani(minimum inhibitory concentrations (MICs) = 11.79-23.66 μM), and compounds2,6, and7greatly inhibitedC. gloeosporioides(MICs = 23.58-47.35 μM), showing an antifungal activity higher than that of carbendazim. Compound1exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC50< 10 μM), and compounds6and9showed potent cytotoxicity against SGC-7901 and A549 cells (IC50< 10 μM).
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. singsongpine@sina.cn.
Song
S
Huang
School of Chemistry and Chemical Engineering, Guangxi University, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Nanning 530004, China. czyzsu@gxu.edu.cn.
Haiyan
H
Chen
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. wsliscau@sina.com.
Wensheng
W
Li
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. zhuxw2580@sina.com.
Xinwei
X
Zhu
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. dwjzsu@scau.edu.cn.
Weijia
W
Ding
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. chunyuanli@scau.edu.cn.
Chunyuan
C
Li
Penicillium chrysogenum; antifungal activity; chaetoglobosin; cytotoxicity; marine mangrove fungus
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