Chemical Modification of Glycyrrhetinic Acid in Relation to the Biological Activities(Medicinal Chemistry,Chemical)

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18β-Olean-12-ene-3β,30-diol (deoxoglycyrrhetol) (4a) was prepared with a view to eliminating pseudoaldosteronism, a side-effect of glycyrrhetinic acid (Ib), which is the sapogenin of Licorice saponin, glyeyrrhizin (1a), while maintaining or enhancing the therapeutic activities. On reduction of the 11-keto and 30-carboxyl groups of 1b with NaAlH_2-(OCH_2CH_2OCH_3)_2, olean-12-ene-3β,11β,30-triol (9) and clean-12-ene-3β,11α,30-triol (10) were obtained. On catalytic hydrogenation of 9 and 10 with Pd-C as a catalyst, 4a was formed in an overall yield of 80%. On treatment with conc. HCl, 9 yielded 18β-olean-9(11),12-diene-3β,30-diol (11a), while 10 yielded clean-11,13(18)-diene-3β,30-diol (12a). Mono- and di-β-carboxy-propionyl and mono- and di-o-phthaloyl esters of 4a, 11a and 12a were prepared to increase the hydrophilic character. The competitive inhibition of 5β,Δ^4-reductase of corticosteroids in the liver which is caused by 1b to induce pseudoaldosteronism was not observed in the case of 4a. Compounds 4a, 11a and 12a and their β-carboxypropionyl and o-phthaloyl esters were studied pharmacologically, and showed antiulcerogenic, antiallergic and antiinflammatory activities.

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  • Chem. Pharm. Bull.

    Chem. Pharm. Bull. 35 1910-1918, 1987

    公益社団法人日本薬学会

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