Ajmaline, Oxindole, and Cytotoxic Macroline-Akuammiline Bisindole Alkaloids from Alstonia penangiana

  • J Nat Prod. 2018 May 25;81(5):1266-1277. doi: 10.1021/acs.jnatprod.8b00170.
Joanne Soon-Yee Yeap ,  Suerialoasan Navanesan ,  Kae-Shin Sim ,  Kien-Thai Yong ,  Subramaniam Gurusamy  1 ,  Siew-Huah Lim ,  Yun-Yee Low ,  Toh-Seok Kam
Affiliations
  • 1. School of Chemical and Life Sciences , Nanyang Polytechnic , 180 Ang Mo Kio Avenue 8 , Singapore 569830 , Singapore.
PMID: 29746134 DOI: 10.1021/acs.jnatprod.8b00170
Abstract

Examination of the EtOH extract of the Malayan Alstonia penangiana resulted in the isolation of 10 new Alkaloids, comprising two ajmaline (1, 2), four macroline oxindole (3-6), and four macroline-akuammiline bisindole Alkaloids (7-10). The structures of these Alkaloids were determined based on analysis of the spectroscopic data and, in the case of the oxindole 6 and the bisindole alkaloid 7, also confirmed by X-ray diffraction analysis. The bisindole Alkaloids 7 and 8 showed pronounced in vitro growth inhibitory activity against an array of human Cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, HCT 116, and A549 cells with IC50 values in the 0.3-8.3 μM range.