Cytotoxic Bromine- and Iodine-Containing Cytochalasins Produced by the Mangrove Endophytic Fungus Phomopsis sp. QYM-13 Using the OSMAC Approach

  • J Nat Prod. 2022 May 27;85(5):1229-1238. doi: 10.1021/acs.jnatprod.1c01115.
Yan Chen  1  2 ,  Wencong Yang  1 ,  Ge Zou  1 ,  Guisheng Wang  2 ,  Wenyi Kang  2 ,  Jie Yuan  3 ,  Zhigang She  1
Affiliations
  • 1. School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China.
  • 2. National R & D Center for Edible Fungus Processing Technology, Henan University, Kaifeng 475004, China.
  • 3. Key Laboratory of Tropical Disease Control, Sun Yat-sen University, Ministry of Education, Guangzhou 510080, China.
PMID: 35473314 DOI: 10.1021/acs.jnatprod.1c01115
Abstract

Twelve new cytochalasins, phomopchalasins D-O (1-3, 5-12, and 14), including one brominated (2) and two iodinated cytochalasins (3 and 6), together with six known analogues (4, 13, and 15-18) were isolated from the mangrove-derived fungus Phomopsis sp. QYM-13 treated with 3% NaBr or 3% KI in potato liquid medium. Their structures and absolute configurations were established by extensive spectroscopic analysis (1D and 2D NMR, HRESIMS), electronic circular dichroism calculations, and a single-crystal X-ray diffraction experiment. Compounds 3 and 6 represent the first iodinated cytochalasins. Compounds 2, 15, 17, and 18 exhibited significant cytotoxicity against human Cancer cell line MDA-MB-435 with IC50 values ranging from 0.2 to 8.2 μM.