Planta Med 2003; 69(2): 167-170
DOI: 10.1055/s-2003-37708
Letter
© Georg Thieme Verlag Stuttgart · New York

Cytotoxic Activity of Natural Labdanes and their Semi-Synthetic Modified Derivatives from Croton oblongifolius

Damrong Sommit1 , Amorn Petsom1 , Tsutomu Ishikawa2 , Sophon Roengsumran1
  • 1Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand
  • 2Faculty of Pharmaceutical Science, Chiba University, Inage, Chiba, Japan
Further Information

Publication History

Received: May 14, 2002

Accepted: October 3, 2002

Publication Date:
07 March 2003 (online)

Abstract

Labda-7,12(E),14-triene-17-oic acid, previously isolated from Croton oblongifolius, and its derivatives were investigated for cytotoxicity against five human tumor cell lines. Six of these compounds, labda-7,12(E),14-triene-17-al, 17-hydroxylabda-7,12(E),14-triene, 17-acetoxylabda-7,12(E),14-triene, 15-hydroxylabda-7,13(E)-diene-17,12-olide, labda-7,13(E)-diene-17,12-olide, and 12,17-dihydroxylabda-7,13(E)-diene showed non-specific, moderate, cytotoxicity against all cell lines, whereas the other compounds were inactive.

References

  • 1 Roengsumran S, Achayindee S, Petsom A, Pudhom K, Singtothong P, Surachetapan C,. et al . Two cembranoids from Croton oblongifolius .  J Nat Prod. 1998;  61 652-4
  • 2 Roengsumran S, Singtothong P, Pudhom K, Ngamrojnavanich N, Petsom A, Chaichantipayuth C. Neocrotocembranal from Croton oblongifolius .  J Nat Prod. 1999;  62 1163-4
  • 3 Roengsumran S, Petsom A, Kuptiyanuwat N, Vilaivan T, Ngamrojnavanich N, Chaichantipyuth C. et al . Cytotoxic labdane diterpenoids from Croton oblongifolius .  Phytochemistry. 2001;  56 103-7
  • 4 Roengsumran S, Musikul K, Petsom A, Vilaivan T, Sangvanich P, Pornpakakul S. et al . Croblongifolin, a new anti-cancer clerodane from Croton oblongifolius .  Planta Med. 2002;  68 271-4
  • 5 Roengsumran S, Petsom A, Sommit D, Vilaivan T. Labdane diterpenoids from Croton oblongifolius .  Phytochemistry. 1999;  50 449-53
  • 6 Singh M, Pal M, Sharma R P. Biological activity of the labdane diterpenes.  Planta Med. 1999;  65 2-8
  • 7 Demetzos C, Mitaku S, Couladis M, Harvala C, Kokkinopoulos D. Natural metabolites of ent-13-epi-manoyl oxide and other cytotoxic diterpenes from the resin ”LADANO” of Cistus creticus .  Planta Med. 1994;  60 590-1
  • 8 Dimas K, Demetzos C, Marsellos M, Sotiriadou R, Malamas M, Kokkinopoulos D. Cytotoxic activity of labdane type diterpenes against human leukemic cell lines in vitro .  Planta Med. 1998;  64 208-11
  • 9 Zhou B -N, Baj N J, Glass T E, Malone S, Werkhoven M CM, van Troon F. et al . Bioactive labdane diterpenoids from Renealmia alpinia collected in the Suriname rainforest.  J Nat Prod. 1997;  60 1287-93
  • 10 Martin S F, Josey J A, Wong Y L, Dean D W. General method for the synthesis of phospholipid derivatives of 1,2-O-diacyl-sn-glycerols.  J Org Chem. 1994;  59 4805-20
  • 11 Paquette L A, Sun L Q, Fridrich D, Savage P B. Total synthesis of (+)-epoxydictymene. Application of alkoxy-directed cyclization to diterpenoid construction.  J Am Chem Soc. 1997;  119 8438-50
  • 12 Marcos I S, Moro R F, Santiago C M, Urones J G. Synthesis of (+)-limonidilactone: Absolute configuration of (-)-limonodilactone.  Tetrahedron Lett. 1999;  40 2615-8
  • 13 Herlem D, Khuong-Huu F, Kende A S. Studies toward the total synthesis of diterpenes in the labdane series 3: Synthesis of 2 epimeric 6,7,8-trihydroxylabdadienes.  Tetrahedron. 1994;  50 2055-70
  • 14 Twentyman P R, Luscombe M. A study of some variables in a tetrazolium dye (MTT) based assay for cell growth and chemosensitivity.  Brit J Cancer. 1987;  56 279-85

Dr. Sophon Roengsumran

Department of Chemistry

Faculty of Science

Chulalongkorn University

Phayathai Rd.

Pathumwan

Bangkok 10330

Thailand

Fax: +66-2-253-0321

Email: amorn.p@chula.ac.th

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