Planta Med 2016; 82 - PC70
DOI: 10.1055/s-0036-1578772

Cytotoxic Triterpenoids From The Leaves And Twigs Of Syzygium Corticosum

Y Ren 1, C Yuan 2, TN Ninh 3, HB Chai 1, EJ Carcache de Blanco 1, 4, DD Soejarto 5, 6, AD Kinghorn 1
  • 1Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, United States
  • 2Campus Chemical Instrument Center, The Ohio State University, Columbus, Ohio 43210, United States
  • 3Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
  • 4Division of Pharmacy Practice and Administration, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States
  • 5Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, United States
  • 6Science and Education, Field Museum of Natural History, Chicago, IL 60605, United States

A large amount of a known triterpene, ursolic acid (6 g from 6 kg of the dried plant sample, with a yield of 0.6% w/w), and a known natural phenol, trimethylellagic acid, were isolated and identified from the leaves and twigs of Syzygium corticosum (Lour.) Merr. & L.M. Perry (Myrtaceae) collected in Vietnam. The structures of both compounds were determined by analysis of their ECD, IR, UV, NMR, and mass spectra and by comparison of these spectroscopic data with literature values, and the cytotoxicity was tested against the HT-29 human colon cancer cell line. The known compound, ursolic acid, was found to show activity, and it was regarded as the major cytotoxic principle of Syzygium corticosum. Several new analogues have been synthesized and evaluated, and it was found that both the C-3 hydroxy and the C-28 carboxyl groups play a key role in mediation of cytotoxicity of ursolic acid against HT-29 cells.

Fig. 1: ursolic acid