2. Academic Validation
  3. Baphicacanthcusines A-E, Bisindole Alkaloids from the Leaves of Baphicacanthus cusia (Nees) Bremek

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

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.

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