A Quantitative Structure-Activity Relationship for Antitumor Activity of Long-Chain Phenols from Ginkgo biloba L.

Hideji ITOKAWA; Nobuo TOTSUKA; Keisuke NAKAHARA; Manaby MAEZURU; Koichi TAKEYA; Miyuki KONDO; Mutsumi INAMATSU; Hiroshi MORITA

doi:10.1248/cpb.37.1619

Hideji ITOKAWA, Nobuo TOTSUKA, Keisuke NAKAHARA, Manaby MAEZURU, Koichi TAKEYA, Miyuki KONDO, Mutsumi INAMATSU, Hiroshi MORITA

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Keywords: structure-activity relationship, quantitative structure-activity relationship, long-chain phenol, Ginkgo biloba, antitumor activity, Sarcoma 180A, P-388, V-79, log P, lowest unoccuplied molecular orbital energy, highest occupied molecular orbital energy, modified neglect of differential overlap method

JOURNAL FREE ACCESS

1989 Volume 37 Issue 6 Pages 1619-1621

DOI https://doi.org/10.1248/cpb.37.1619

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Abstract

With the aim of obtaining compounds with strong antitumor activity, a quantitative structure-activity relationship (QSAR) of antitumor phenolic compounds (long-chain phenols) was derived using the Hansch-Fujita equation. The ED₅₀ values against Chinese hamster V-79 cells were analyzed in terms of log P as the hydrophobic parameter and the energy of the lowest unoccupied molecular orbital (E_LUMO) calculated by using the modified neglect of differential overlap (MNDO) method as the electronic parameter, by means of multiple regression analysis. It was found that the activities mainly depended on log P (an optimum log P of 8.3) and a low-lying E_LUMO value. 4-Undecylcatechol, selected on the basis of the above results, exhibited strong antitumor activity against Sarcoma 180 ascites and P-388 lymphocytic leukemia.

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