Isochromophilones A-F, Cytotoxic Chloroazaphilones from the Marine Mangrove Endophytic Fungus Diaporthe sp. SCSIO 41011

  • J Nat Prod. 2018 Apr 27;81(4):934-941. doi: 10.1021/acs.jnatprod.7b01053.
Xiaowei Luo  1  2 ,  Xiuping Lin  1 ,  Huaming Tao  3 ,  Junfeng Wang  1 ,  Jiayi Li  1  3 ,  Bin Yang  1 ,  Xuefeng Zhou  1 ,  Yonghong Liu  1  2
Affiliations
  • 1. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica , South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301 , People's Republic of China.
  • 2. University of Chinese Academy of Sciences , Beijing 100049 , People's Republic of China.
  • 3. School of Traditional Chinese Medicine , Southern Medical University , Guangzhou 510515 , People's Republic of China.
PMID: 29517908 DOI: 10.1021/acs.jnatprod.7b01053
Abstract

Six new highly oxygenated chloroazaphilone derivatives, isochromophilones A-F (1-6), were obtained from the mangrove-derived fungus Diaporthe sp. SCSIO 41011, together with six known analogues (7-12). The structures of 1-6 including absolute configurations were determined by detailed NMR, MS spectroscopic analyses, and electronic circular dichroism spectra. Compounds 1 and 2 represent the first reported azaphilones lacking a carbonyl group at C-6. Compound 8 exhibited cytotoxic activities against three renal carcinoma cell lines, ACHN, OS-RC-2, and 786-O cells, with IC50 values ranging from 3.0 to 4.4 μM, and 4 showed activity against 786-O cells with an IC50 of 8.9 μM. Further studies indicated that 4 induced Apoptosis in 786-O cells in a dose- and time-dependent manner.