Quinones, Flavans, and Other Nonnitrogenous Higher Plant Products
All of the miscellaneous plant products ranging from hydrocarbons to the highly oxygenated polysaccharides have been grouped into this chapter. In general they have shown only marginal cytotoxic and/or in vivo antitumor properties. The gallic acid that we found to be the cytotoxic constituent of two Utah plants, Rhus trilobata (Anacardiaceae) and Oenothera caespitosa (Onagraceae), seems to be the smallest molecular-weight natural product so far isolated with those properties.323 A substance of comparable size with in vivo anticancer activity is crotepoxide (95), reported by Kupchan218 to be the antineoplastic agent of Croton macrostachys Höchst, ex. A. Rich (Euphorbiaceae). Cyclohexane diepoxide 95 was found to have activity against the LL system at a toxic dose and also to show inhibition of the WM tumor system. From a biogenetic viewpoint, crotepoxide seems related to shikimic acid. Ichihara and co-workers288 have completed a total synthesis of (±) crotepoxide.
KeywordsGallic Acid Antineoplastic Agent Shikimic Acid Total Synthesis Aristolochic Acid
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