Planta Med 2005; 71(3): 208-213
DOI: 10.1055/s-2005-837818
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Activity of Lupane-Type Triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum Two of which Induce Apoptosis

Prapawadee Puapairoj1 , Waree Naengchomnong2 , Anake Kijjoa3 , Madalena M. Pinto4 , Madalena Pedro5 , Maria São José Nascimento5 , Artur M. S. Silva6 , Werner Herz7
  • 1Department of Pharmacology, Faculty of Medicine, Khonkhaen University, Khonkhaen, Thailand
  • 2Department of Chemistry, Faculty of Sciences, Burapha University, Bangsaen, Chonburi, Thailand
  • 3ICBAS-Instituto de Ciências Biomédicas de Abel Salazar-CIIMAR, Universidade do Porto, Porto, Portugal
  • 4Laboratório de Química Orgânica, Faculdade de Farmácia-Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia de Universidade do Porto, Faculdade de Farmácia (CEQOFFUP), Porto, Portugal
  • 5Laboratório de Microbiologia, Faculdade de Farmácia-Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia de Universidade do Porto, (CEQOFFUP), Port, Portugal
  • 6Departamento de Química, Universidade de Aveiro, Aveiro, Portugal
  • 7Department of Chemistry and Biochemistry, The Florida State University, Tallahassee, FL, USA
Further Information

Publication History

Received: May 4, 2004

Accepted: October 8, 2004

Publication Date:
15 March 2005 (online)

Abstract

Six known lupanes lupenone (1), 3-epi-lupeol (2), glochidone (4), glochidonol (5), glochidiol (6) and lup-20(29)-ene-1β,3β-diol (7) were isolated from the roots and stem wood of Glochidion eriocarpum and three, 5, 6 and lup-20(29)ene-3α,23-diol (3), were isolated from the roots and stem wood of Glochidion sphaerogynum. Compounds were identified by 1H- and 13C-NMR techniques. Triterpenes 2 - 7 were tested against the growth of three human tumor cell lines, MCF-7, NCI-H-460 and SF-268. Lupanes 3, 5, and 6 exhibited strong inhibitory effects against all three; thus GI50 values for 3 were 12.7 ± 3.7, 17.9 ± 1.1 and 17.9 ± 0.5, for 5 9.0 ± 3.7, 4.9 ± 0.2 and 9.8 ± 0.5, and for 6 6.63 ± 0.7, 7.5 ± 0.5 and 9.7 ± 0.3.3. Epilupeol was less active, with GI50 values of 75.6 ± 11.7, 86.1 ± 12.4 and 80.9 ± 2.6 while 7 was moderately active only against MCF-7 (GI50 = 79.2 ± 2.4). Additional studies indicated that triterpenes 5 and 6 exerted their antiproliferative activity through the involvement of apoptosis while triterpene 3 did not.

References

Werner Herz

Department of Chemistry and Biochemistry

The Florida State University

Tallahassee

FL 32306-4390

USA

Phone: +1-850-644-2770

Fax: +1-850-644-8281

Email: jdulin@chem.fsu.edu