Planta Med 2006; 72(9): 830-834
DOI: 10.1055/s-2006-946683
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Macrocyclic Diterpenoid Esters from Euphorbia cornigera

Imam Bakhsh Baloch1 , Musa Kaleem Baloch1 , Qazi Najam us Saqib2
  • 1Department of Chemistry, Gomal University, Dera Ismail Khan, Pakistan
  • 2Department of Pharmacognosy, Faculty of Pharmacy, Gomal University, Dera Ismail Khan, Pakistan
Further Information

Publication History

Received: December 27, 2005

Accepted: May 16, 2006

Publication Date:
17 July 2006 (online)

Abstract

Root extract of Euphorbia cornigera Boiss. (Euphorbiaceae) was separated into seven (compound 1 - 7) isolates through multiple Craig’s distributions and preparative HPLC. The structures and relative configuration of theses compounds were established via spectral analyses as 7,8,12-O-triacetyl-3-O-(2-methylbutanoyl)-ingol (1), 3,8,12-O-triacetyl-7-O-(2-methylbutanoyl = -ingol (2), 3,7,12-O-triacetyl-8-O-(2-methylbutanoyl)-ingol (3), 3,7,8-O-triacetyl-12-O-(2-methylbutanoyl)-ingol (4), 7,12-O-diacetyl-3-O-(2-methylbutanoyl)-8-O-methylingol (5), 3,12-O-diacetyl-7-O-(2-methylbutanoyl)-8-O-methylingol (6) and 3,7-O-diacetyl-12-O-(2-methylbutanoyl)-8-O-methylingol (7). All these compounds, except for 2, are novel metabolites and have not been reported earlier. It has further been demonstrated that all the compounds (1 - 7) are cytotoxic.

References

  • 1 Abo K, Evans F J. Macrocyclic diterpene esters of the cytotoxic fraction from Euphorbia kamerunica .  Phytochemistry. 1981;  20 2535-7
  • 2 Abo K, Evans F J. The composition of a mixture of ingol esters from Euphorbia kamerunica .  Planta Med. 1981;  43 392-5
  • 3 Arisawa M, Nimura M, Ikeda A, Hayashi T, Morita N, Momose Y. et al . Biologically active macrocyclic diterpenoids from Chinese drug ”Fang Feng Cao” I. Isolation and structure.  Planta Med. 1986;  48 38-41
  • 4 Abo K, Evans F J. Tri-ester of ingol from the latex of Euphorbia kamerunica .  J Nat Prod. 1981;  45 365-6
  • 5 Schroeder G, Rohmer M, Beck J P, Anton R. Cytotoxic activity of 6,20-epoxylathrol and its aliphatic diesters.  Planta Med. 1979;  35 235-41
  • 6 Adolf W, Hecker E. Further new diterpene esters from the irritant and co-carcinogenic seed oil and latex of the Caper spurge (Euphorbia lathyris L).  Experientia. 1971;  27 1393-4
  • 7 Conally J D, Fakunle C O, Rycroft D S. Five ingol esters and 17-hydroxyingenol esters from the latex of Euphorbia kamerunica .  Tetrahedron Lett. 1984;  25 3773-6
  • 8 Khan A Q, Malik A. A new macrocyclic diterpenes ester from the latex of Euphorbia tirucalli .  J Nat Prod. 1990;  53 728-31
  • 9 Morgenstern T, Bittner M, Silva M, Aquueveque P, Jakupovic J. Diterpenes and phloroacetophenones from Euphorbia portulacoides.  Phytochemistry. 1996;  41 1149-53
  • 10 Lin L -J, Kinghorn A D. 8-Methoxyingol esters from the latex of E. hermentiana .  Phytochemistry. 1983;  22 2795-9
  • 11 Dymock W W. Pharmacographia Indica. Karachi; Zain Packing Industries 1972
  • 12 Miana G A, Ahmad B, Evans F J. Isolation of prostratin from Euphorbia cornigera .  Planta Med. 1985;  51 353-4
  • 13 Baloch I B, Baloch M K, Saqib Q N. Tumor-promoting diterpene esters from latex of E. cauducifolia L.  Helv Chim Acta. 2005;  88 3541-50
  • 14 Baloch I B, Baloch M K, Saqib Q N, Mansoor A. 16-Hydroxyingeol diterpene ester from the latex of E. cauducifolia L. Int.  J Med Pharm Chem. 2004;  1 107-11
  • 15 Mosmann T. Rapid colorimetric assay for cellular growth and survival; application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  16 55-63

Musa Kaleem Baloch

Department of Chemistry

Gomal University

Dera Ismail Khan

Pakistan

Phone: +92-966-750-424

Fax: +92-966-750-255

Email: musakaleem2001@yahoo.com

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