Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

  • J Nat Prod. 2002 Jun;65(6):902-8. doi: 10.1021/np0200257.
Yu Zhao  1 ,  Xiaojiang Hao ,  Wei Lu ,  Junchao Cai ,  Hong Yu ,  Thierry Sevénet ,  Françoise Guéritte
Affiliations
  • 1. Department of Traditional Chinese Medicine and Natural Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310031, People's Republic of China. [email protected]
PMID: 12088436 DOI: 10.1021/np0200257
Abstract

Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB Cancer cell lines.