Description and references

A group of tetracyclic triterpenes, commonly referred to as “bitter principles of cucurbits”, which have antineoplastic and anti-gibberellin activity. They are isolated from various spp of cucurbitaceous plants known since antiquity for their beneficial and toxic properties. The plants have been used as vermifuges, emetics, narcotics, and antimalarials and have been implicated in sporadic livestock poisoning in S. Africa. Seventeen cucurbitacins have been isolated, most from plants of the Cucurbitaceae family, but also from Begoniaceae, Cruciferae, Datisceae, Euphorbiaceae, and Scrophulariaceae. Cucurbitacins B and E are the most commonly identified. Isoln of cucurbitacins A, B, C, D, F: P. R. Enslin, J. Sci. Food Agric. 5, 410 (1954); of G, H, J, K, L: idem, ibid. 8, 673 (1957); of E and I: D. Lavie, S. J. Szinai, J. Am. Chem. Soc. 80, 707 (1958); of O, P, Q and antitumor activity: S. Kupchan et al., J. Org. Chem. 35, 2891 (1970). Structures of A, B, C, D, E, I: W. T. DeKock et al., J. Chem. Soc. 1963, 3828; of B, D, F: D. Lavie et al., Chem. Ind. (London) 1959, 951; of G, H: C. W. Holzapfel, P. R. Enslin, J. S. Afr. Chem. Inst. 17, 142 (1964), C.A. 62, 10467c (1965); of J, K, L: P. R. Enslin, K. B. Norton, J. Chem. Soc. 1964, 529. Stereochemistry of B, D, E, F, I: D. Lavie et al., J. Org. Chem. 28, 1790 (1963). ¹³C-NMR study of cucurbitacins: V. V. Velde, D. Lavie, Tetrahedron 39, 317 (1983). Use as plant growth regulators: J. Guha, S. P. Sen, Nature New Biol. 244, 273 (1973). Toxicity studies: J. LeMen et al., Chim. Ther. 4, 459 (1969); D. Albert et al., Chim. Ther. 5, 205 (1970). Reviews: D. Lavie, E. Glotter, Fortschr. Chem. Org. Naturst. 29, 308-357 (1971); J. Guha, S. P. Sen, Plant Biochem. J. 2, 12-28 (1975); A. Shrotria, Botanica 26, 28-31 (1976).

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