Planta Med 2003; 69(4): 361-366
DOI: 10.1055/s-2003-38875
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Three New Jatrophane-Type Diterpenes from Euphorbia pubescens

Cláudia Valente1 , Maria José U. Ferreira1 , Pedro M. Abreu2 , Madalena Pedro3 , Fátima Cerqueira3 , Maria São José Nascimento3
  • 1Centro de Estudos de Ciências Farmacêuticas, Faculdade de Farmácia da Universidade de Lisboa, Lisboa, Portugal
  • 2CQFB/REQUIMTE, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, Caparica, Portugal
  • 3Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia da Universidade do Porto, Faculdade de Farmácia, Porto, Portugal
Further Information

Publication History

Received: August 5, 2002

Accepted: November 23, 2002

Publication Date:
23 April 2003 (online)

Abstract

Three new macrocyclic jatrophane diterpene polyesters, named pubescenes A (1), B (2), and C (3), and the known compounds indole-3-aldehyde and scopoletin have been isolated and characterised from the whole dried plant of Euphorbia pubescens. The structures of the new compounds were established by spectroscopic means including 2D-NMR techniques such as COSY, HMQC, HMBC and NOESY experiments. Compounds 1 - 3 were evaluated for their in vitro effect on the growth of three human cancer cell lines MCF-7 (breast), NCI-H460 (lung) and SF-268 (CNS) as well as for their capacity to interfere with the proliferation of human peripheral blood lymphocytes. They exhibited a moderate growth inhibitory effect on the cancer cell line NCI-H460. No effect was observed on the mitogenic response of human lymphocytes to PHA.

References

  • 1 Hartwell J L. Plants used against cancer. A survey.  Lloydia. 1969;  62 153-205
  • 2 Seip E H, Hecker E. Derivatives of characiol, macrocyclic diterpene esters of the jatrophane type from Euphorbia characias .  Phytochemistry. 1984;  23 1689-94
  • 3 Yamamura S, Kosemura S, Ohba S, Ito M, Saito Y. The isolation and structures of euphoscopins A and B.  Tetrahedron Lett. 1981;  22 5315-8
  • 4 Kupchan S M, Siegel C W, Matz M J, Gilmore C J, Bryan R F. Structure and stereochemistry of jatrophone, a novel macrocyclic diterpenoid tumor inhibitor.  J Am Chem Soc. 1976;  98 2295-300
  • 5 Zheng W F, Cui Z, Zhu Q. Cytotoxic and antiviral activity of the compounds from Euphorbia kansui .  Planta Med. 1998;  64 754-6
  • 6 Hohmann J, Molnár J, Rédei D, Evanics F, Forgo F, Kálmán A, Argay G, Szabó P. Discovery and biological evaluation of a new family of potent modulators of multidrug resistance: reversal of multidrug resistance of mouse lymphoma cells by new natural jatrophane diterpenoids isolated from Euphorbia species .  J Med Chem. 2002;  45 2425-31
  • 7 Hohmann J, Vasas A, Günther G, Máthé I, Evanics F, Dombi G, Jerkovitch G. Macrocyclic diterpene polyesters of the jatrophane type from Euphorbia esula .  J Nat Prod. 1997;  60 331-35 and related references cited therein
  • 8 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines.  J Natl Cancer Inst. 1990;  82 1107-12
  • 9 Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro-Wolff A, Gray-Goodrich M, Campbell H, Mayo J, Boyd M. New colorimetric cytotoxicity assay for anticancer-drug screening.  J Natl Cancer I. 1991;  83 757-66
  • 10 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assay.  J Immunol Methods. 1983;  65 55-63
  • 11 Gonzalez M J, Nascimento M SJ, Cidade H M, Pinto M MM, Kijjoa A, Anantachoke C, Silva AM S, Herz W. Immunomodulatory activity of xanthones from Calophyllum teysmannii var. inuphylloide .  Planta Med. 1999;  65 368-71
  • 12 Appendino G, Jakupovic S, Tron G C, Jakupovic J, Milon V, Ballero M. Macrocyclic diterpenoids from Euphorbia semiperfoliata .  J Nat Prod. 1998;  61 749-56
  • 13 Lieu L G, Tan R X. New jatrophane diterpenoid esters from Euphorbia turczaninowii .  J Nat Prod. 2001;  64 1064-68 and related references cited therein
  • 14 Ferreira M JU, Madureira A M, Ascenso J R. A tetracyclic diterpene and triterpenes from Euphorbia segetalis .  Phytochemistry. 1998;  49 179-83
  • 15 Stothers J B. Carbon-13 NMR spectroscopy. In: Blomquist AT, Wasserman H, editors Academic Press Vol. 24 New York; 1972: pp. 150-1, 442 - 3
  • 16 Yamamura S, Yoshikazu S, Kosemura S, Ohtsuka J, Tayama T, Ohba S, Ito M, Saito Y, Terada Y. Diterpenes from Euphorbia helioscopia .  Phytochemistry. 1989;  28 3421-36
  • 17 Bohlmann F, Jakupovic J. 8-Oxo-α-selinen und neue Scopoletin-Derivate aus Conya Arten.  Phytochemistry. 1979;  18 1367-79
  • 18 Evidente A. Isolation of indole-3-aldehyde from Pseudomonas syringae pv. Savastanoi .  J Nat Prod. 1986;  49 938-9

Prof. Maria José Umbelino Ferreira

Centro de Estudos de Ciências Farmacêuticas

Faculdade de Farmácia da Universidade de Lisboa

Av. das Forças Armadas

1600-083 Lisboa

Portugal

Email: mjuferreira@ff.ul.pt

Fax: +351-21-7946470