Abstract
In order to determine the structure-activity relationships for antioxidative effects of gagaminine, a steroidal alkaloid isolated from the roots ofCynanchum wilfordi (Asclepiadaceae), two derivatives identified as sarcostin and penupogenin were prepared from gagaminine by hydrolysis and reduction. These compounds were evaluated for the inhibitory effects on the aldehyde oxidase activity and on lipid peroxidationin vitro. Furthermore, their effects were compared with those of gagaminine and the related compounds, cinnamic acid and nicotinic acid. The results of this study prove that the cinnamoyl group in the structure of gagaminine is critical in inhibition of the aldehyde oxidase activity while the nicotinoyl group may be necessary for anti-lipid peroxidation of the compound.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References Cited
Branzoli U., Massey V., Preparation of aldehyde oxidase in its native and deflavo forms.J. Biol. Chem., 249, 4339–4345 (1974).
Fukuoka, M. and Mitsuhashi, H., Studies on the constituents of Asclepiadaceae plants. XXIV. Structure of stephanol.Chem. Pharm. Bull., 17, 2448–2454 (1969).
Halliwell, B., Antioxidant characterization. Methodology and mechanism.Biochem. Pharmacol., 49, 1341–1348 (1995).
Harman, D.,J. Am. Geriat. Soc., 17, 721 (1969).
Lee, D.U., Shin, U.S., Yi, S.J. and Huh, K., Effect of alkaloidal fraction from Cynanchi radix on lipid peroxidation.Yakhak Hoeji, 38, 786–790 (1994).
Lee, D.U., Antioxidative effects of the crude alkaloid fraction from Cynanchum wilfordi.Dongguk Journal, 14, 83–92 (1995).
Lee, D.U., Shin, U.S. and Huh, K., Inhibitory effects of gagaminine, a steroidal alkaloid fromCynanchum wilfordi, on lipid peroxidation and aldehyde oxidase activity.Planta Med., 62, 485–487 (1996).
Lowry, O. H., Rosebrough, N. J., Farr, A. L. and Randall, R. J., Protein measurement with the folin phenol reagent.J. Biol. Chem., 193, 265–275 (1951).
Mitsuhashi, H. and Shimizu, Y., Studies on the components of Asclepiadaceae plants V. The isolation and structures of penupogenin.Chem. Pharm. Bull., 10, 725–727 (1962).
Muller, K., Freie Radikale.Deutsche Apotheker Zeitung, 132, 1473–1482 (1992).
Ohkawa, H., Ohishi, N. and Yagi, K., Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction.Anal. Biochem., 95, 351–358 (1979).
Shimizu, Y. and Mitsuhashi, H., Studies on the components of Asclepiadaceae plants-XXII. Structures of cynanchogenin and sarcostin.Tetrahedron, 24, 4143–4151 (1968).
Stirpe, F. and Corte, E.D., The regulation of rat liver xanthine oxidase.J. Biol. Chem., 244, 3855–3863 (1969).
Warashina, T. and Noro T., Steroidal glycosides from the roots ofCynanchum caudatum M.Chem. Pharm. Bull., 43, 977–982 (1995).
Yamagishi, T., Hayashi, K. and Mitsuhashi, H., The structure and internal migration of gagaminine.Chem. Pharm. Bull., 20, 2289–2291 (1972).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lee, D.U., Shin, U.S. & Huh, K. Structure-activity relationships of gagaminine and its derivatives on the inhibition of hepatic aldehyde oxidase activity and lipid peroxidation. Arch. Pharm. Res. 21, 273–277 (1998). https://doi.org/10.1007/BF02975287
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02975287