Cytotoxic Diterpenoids from Euphorbia pekinensis

Abstract

A new diterpenoid, named euphpekinensin, along with three known diterpenoids, was isolated from the roots of Euphorbia pekinensis for the first time and the structures were elucidated by spectral analysis. The 2D-NMR techniques such as ¹H-¹H COSY, HMQC, HMBC and NOESY spectra were mainly applied to determine the structure of the new diterpenoid. The four diterpenoids showed cytotoxic activity against human KB cells in vitro.

Key words

Euphorbia pekinensis - Euphorbiaceae - euphpekinensin - diterpenoids - cytotoxic activity

References

• 1 Jiangsu College of New M edicine. The Dictionary of the Traditional Chinese Medicine. Shanghai Press of Science & Technology Shanghai; 1977: 108-10
• 2 Giovanni A, Sven J, Gian C T, Jasmin J, Veronique M, Mauro B. Macrocyclic diterpenoids from Euphorbia semiperfoliata .  Journal of Natural Products. 1998;  61 749-56
• 3 Adolf W, Hecker E, Becker H. Macrocyclic lathyrane type diterpene esters (Jolkinols) from callus cultures and roots of Euphorbia lathyris .  Planta Medica. 1984;  50 259-61
• 4 Yoshikazu S, Jiro O, Seiji K, Yukimasa T, Shosuke Y. Biomimetic reactions of some macrocyclic diterpenes.  Tetrahedron Letters. 1984;  25 5547-50
• 5 Jiao Y, Liu J H, Liu G F, Yuan C L. Advances research on the main chemical constituents of Euphorbia .  Zhongcaoyao. 1990;  21 87-92
• 6 Oksuz S, Gurek F, Yang S W, Lin L Z, Cordell G A, Pezzuto J M, Wagner H, Lotter H. Paralinones A and B, novel diterpene esters from Euphorbia paralias .  Tetrahedron. 1997;  53 3215-22
• 7 Kong L Y, Min Z D. Studies on chemical constituents of roots of Euphorbia pekinensis .  Acta Pharmaceutica Sinica. 1996;  31 524-9
• 8 Robinson D R, West C A. Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis. I. Identification of diterpene hydrocarbons formed from mevalonate.  Biochemistry. 1970;  9 70-9
• 9 Robinson D R, West C A. Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis. I. Conversion of geranyl-geranyl pyrophosphate into diterpene hydrocarbons and partial purification of the cyclization enzymes.  Biochemistry. 1970;  9 80-9
• 10 Burke B A, Chan B A, Pascoe K O, Blount J F, Manchard P S. The structure of crotonitenone, a novel casbane diterpene from Croton nitens Sw. (Euphorbiaceae).  Journal of the Chemical Society Perkin Transactions. 1981;  I 2666-9
• 11 Commisiong M A, Pascoe K. The absolute stereochemistry of crotonitenone.  Tetrahedron Letters. 1984;  25 711-2
• 12 Choi Y H, Kim J, Pezzuto J M, Kinghorn A D, Farnsworth N R. Agrostistachin, a novel cytotoxic macrocyclic diterpene from Agrostistachys hookeri .  Tetrahedron Letters. 1986;  27 5795-8
• 13 Choi Y H, Pezzuto J M, Kinghorn A D, Farnsworth N R. Plant anticancer agents, cytotoxic casbane-type constituents of Agrostistachys hookeri .  Journal of Natural Products. 1988;  51 110-6
• 14 Xu Z H, Sun J, Xu R S, Qin G W. Casbane diterpenoids from Euphorbia ebracteolata .  Phytochemistry. 1998;  49 149-51
• 15 Lin L J, Kinghorn A D. 8-Methoxyingol esters from the latex of Euphorbia hermentiana .  Phytochemistry. 1983;  22 2795-9
• 16 Rizk A M, Hammouda F M, El-Missiry M M, Radwan H M, Evans F J. Macrocyclic diterpene esters from Euphorbia royleana .  Phytochemistry. 1984;  23 2377-9
• 17 Abo K, Evans F J. The composition of a mixture of ingol esters from Euphorbia kamerunica .  Planta Medica. 1981;  43 392-5
• 18 Opferkuch H J, Hecker E. Ingol - a new macrocyclic diterpene alcohol from Euphorbia ingens . Tetrahedron Letters 1973: 3611-4