Baphicacanthcusines A-E, Bisindole Alkaloids from the Leaves of Baphicacanthus cusia (Nees) Bremek

  • J Org Chem. 2020 Jul 2;85(13):8580-8587. doi: 10.1021/acs.joc.0c00949.
Ling-Juan Zhu  1 ,  Fei Cao  2 ,  Xiang-Xin Su  1 ,  Chun-Yu Li  1 ,  Bin Lin  1 ,  Hai-Feng Wang  1 ,  Xin-Sheng Yao  1 ,  Xue Zhang  1 ,  Jing-Ming Jia  1 ,  Hong-Wei Liu  1  3
Affiliations
  • 1. Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
  • 2. College of Pharmaceutical Sciences, Hebei University, Baoding 071002, China.
  • 3. State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.
PMID: 32501005 DOI: 10.1021/acs.joc.0c00949
Abstract

Four pairs of stereoisomeric Indole Alkaloids, (±)-baphicacanthcusines A-D (1-4), and one new indole alkaloid, baphicacanthcusine E (5), together with nine known compounds were identified from the leaves of Baphicacanthus cusia. (±)-1 and -2 possess an unprecedented skeleton in which two indole moieties are bridged by a phenylpropane unit. (±)-3 represents the first natural dispiro-oxazolidinone bisoxindoles. The absolute configurations in 1-5 were assigned based on quantum chemical calculations, including the calculated chemical shift with DP4plus analysis, the calculated optical rotation values, and the calculated electronic circular dichroism spectra. A plausible biosynthetic pathway for 1-5 was proposed. Compounds (±)-1, (-)-2, and 11 exhibited cytotoxicity against MCF-7 cells with IC50 values of 20.0-78.5 μM.

Products