Abstract
The methanol extract from roots of Salacia hainanensis Chun et How afforded three new compounds, 24,26-dihydroxy-25-methoxy-tirucall-9-en-3-one (1), 2β,3β,22α-trihydroxy-lup-20(29)-ene (2) and 3β-hydroxy-2-carbonyl-lupan-29-oic acid (3), along with six known triterpenoids (4–9). Their structures were established on the basis of spectral analysis, in particular according to the data obtained by two-dimensional-NMR and high-resolution mass spectra experiments. Some of them showed much stronger inhibitory activity towards α-glucosidase than the positive control (acarbose, IC50 10.2 μM).
This is a preview of subscription content, log in via an institution to check access.
References
Ross SA, Gulve EA, Wang M (2004) Chemistry and biochemistry of type 2 diabetes. Chem Rev 104:1255–1282
Dong W, Jespersen T, Bols M, Skrydstrup T, Sierks MR (1996) Evaluation of isofagomine and its derivatives as potent glycosidase inhibitors. Biochemistry 35:2788–2795
Brownlee M (2001) Biochemistry and molecular cell biology of diabetic complications. Nature 414:813–820
State Chinese Medicine Administration Bureau (1999) Chinese Materia Medica, Shanghai Science Press, Shanghai, China, 13(5):219
Yuan G-J, Tian Y-W, Wang Z-Q (2005) Hypoglycemic effect of the alcohol extract from the roots of Salacia hainanensis. Trad Chin Drug Res Clin Pharm 16:253–256
Huang J, Guo Z-G, Cheng P, Sun B-H, Gao H-Y (2012) Three new triterpenoids from Salacia hainanensis Chun et How showed effective anti-α-glucosidase activity. Phytochem Lett 5:432–437
Wayne DI, Michael JR, Menlo P (1997) U.S. Patent, No. 5691386
Shashi BM, Asish PK (1994) 13C NMR spectra of pentacyclic triterpenoids––a compilation and some salient features. Phytochemistry 37:1517–1575
Minh TT, Anh NTH, Thang VD, Sung TV (2010) Study on chemical constituents and cytotoxic activities of Salacia chinensis growing in Vietnam. Z Naturforsch Sect B J Chem Sci 65:1284–1288
Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M (2003) Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis. J Nat Prod 66:1191–1196
Mulholland DA, Kotsos M, Mahomed HA, Taylor DAH (1998) Triterpenoids from Owenia cepiodora. Phytochemistry 49:2457–2460
Zhang J, Guo H-Z, Tian Y, Liu P, Li N, Zhou J-P, Guo D-A (2007) Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products. Phytochemistry 68:2523–2530
Kanji I, Hiroshi S, Motoyoshi S, Koichiro S (1990) Phenyl glucosides from a hairy root culture of Swertia japonica. Phytochemistry 29:3823–3825
Endová M, Klinotová E, Sejbal J, Máca B, Klinot J, Protiva J (1994) Preparation of 2,3-secodiacids of the lupane series. Collect Czech Chem Comm 59:1420–1429
Ma H-Y, Gao H-Y, Sun L, Huang J, Xu X-M, Wu L-J (2011) Constituents with α-glucosidase and advanced glycation end-product formation inhibitory activities from Salvia miltiorrhiza Bge. J Nat Med 65:37–42
Matsui T, Ueda T, Oki T, Sugita K, Terahara N, Matsumoto K (2001) α-Glucosidase inhibitory action of natural acylated anthocyanins. 1. Survey of natural pigments with potent inhibitory activity. J Agric Food Chem 49:1948–1951
Acknowledgments
We thank Mrs. Wen Li and Mr. Yi Sha of the Analytical Center of the Shenyang Pharmaceutical University for recording NMR spectra, Prof. Qishi Sun for identification of plant material, and Shenyang Pharmaceutical University for technical assistance. This work was supported by the National Natural Science Foundation Project of China (No. 30772717).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Guo, Zh., Huang, J., Wan, Gs. et al. New inhibitors of α-glucosidase in Salacia hainanensis Chun et How. J Nat Med 67, 844–849 (2013). https://doi.org/10.1007/s11418-013-0744-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-013-0744-5