Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

  • Mar Drugs. 2016 Sep 27;14(10):172. doi: 10.3390/md14100172.
Song Huang  1 ,  Haiyan Chen  2 ,  Wensheng Li  3 ,  Xinwei Zhu  4 ,  Weijia Ding  5 ,  Chunyuan Li  6
Affiliations
  • 1. College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. [email protected].
  • 2. School of Chemistry and Chemical Engineering, Guangxi University, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Nanning 530004, China. [email protected].
  • 3. College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. [email protected].
  • 4. College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. [email protected].
  • 5. College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. [email protected].
  • 6. College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. [email protected].
PMID: 27690061 DOI: 10.3390/md14100172
Abstract

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 of Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound 1 was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2' of the chaetoglobosin class. Compounds 5-8 remarkably inhibited the plant pathogenic fungus R. solani (minimum inhibitory concentrations (MICs) = 11.79-23.66 μM), and compounds 2, 6, and 7 greatly inhibited C. gloeosporioides (MICs = 23.58-47.35 μM), showing an Antifungal activity higher than that of carbendazim. Compound 1 exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC50 < 10 μM), and compounds 6 and 9 showed potent cytotoxicity against SGC-7901 and A549 cells (IC50 < 10 μM).

Keywords
Penicillium chrysogenum; antifungal activity; chaetoglobosin; cytotoxicity; marine mangrove fungus.
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