Flavonoids from litchi(Litchi chinensis Sonn.) seeds and their inhibitory activities on α-glucosidase

Abstract

With the bioactivity-guided method, a new flavanone glycoside, together with nine known flavonoids were isolated from 50% aqueous ethanol of litchi(Litchi chinensis Sonn.) seeds. The chemical structure of the new compound was elucidated via 1D and 2D nuclear magnetic resonance(NMR) techniques and mass spectrometry to be (2S)-pinocembrin-7-O-(6″-O-α-L-arabinosyl-β-D-glucopyranoside)(1), and the nine known compounds were determined to be quercetin(2), phlorhizin(3), pinocembrin-7-O-glucoside(4), kaempferol-7-O-β-D-glucopyranoside(5), onychin(6), nairutin(7), narcissin(8), pinocembrin-7-O-[(6″-O-β-D-glucopyranoside)-β-D-glucopyranoside](9) and pinocembrin-7-O-[(2″,6″-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside](10). Some of the isolated flavonoids were tested for their inhibitory effects on α-glucosidase. And compounds 2 and 3 showed stronger inhibitory activity than positive control.

Keywords

Litchi chinensis Sonn. seed / Flavanoid / Inhibitory activity / α-Glucosidase

References

[1] Liu Y Q, Pi Z F, Song F R, Liu Z Q, Liu Z Y. Chem. J. Chinese Universities, 2012, 33(9): 1932.

[2] Pogano G, Marena S, Corgiat-Mansin L, Cravero F, Giorda C, Bozza M, Rossi C M. Diabetes and Metabolism, 1995, 21(3): 162.

[3] Murai A, Iwamura K, Takada M, Ogawa K, Usui T, Okumura J. Life Science, 2002, 71(12): 1405.

[4] Lebovitz H E. Endocrinology and Metabolism Clinics of North America, 1997, 26(3): 539.

[5] Holman R R. Diabetes Research and Clinical Practice, 1998, 40(Suppl.1): S21.

[6] Niwa T, Doi U, Osawa T. Journal of Agricultural and Food Chemistry, 2003, 51(1): 90.

[7] Mcdougall G J, Shpiro F, Doboson P, Smith P, Black A, Stewart D. Journal of Agricultural and Food Chemistry, 2005, 53(7): 2760.

[8] Fang J, Li Y P, Liang W H, Dong D C, Liu Y Q. World Agriculture, 2007, 3: 46.

[9] Guo J W, Pan J Q, Qiu G Q, Li A H, Xiao L Y H C. Chinese Journal of New Drugs, 2003, 12(7): 526.

[10] Yang Y J, Liang B M. Guangdong Pharmaceutical Journal, 2004, 14(6): 13.

[11] Liu Y G. Pharmaceutical Composition Containing a Safe Extracts of Fruits and Vegetables for the Treating and Preventing of Diabetes, 1991.

[12] Hanawa F, Yamada T, Nakashima T. Phytochemistry, 2001, 57(2): 223.

[13] Li M M, Wang K, Pan Z H, Chen X Q, Peng L Y, Cheng X, Zhao Q S. Chem. Pharm. Bull., 2009, 57(10): 1123.

[14] Zeng H B, Zeng R J, Yao F. Journal of Hunan Institute of Engineering, 2010, 20(2): 60.

[15] Liu H W, Yao X S. Chinese Journal of Medicinal Chemistry, 2001, 1: 52.

[16] Feng H, Wang Z M, Dong G Y, Wu Z. China Journal of Chinese Material Medica, 2001, 26(4): 260.

[17] Markham K R, Ternam B, Stanley R, Geiger H, Mabry T J. Tetrahedron, 1978, 34(9): 1389.

[18] Xu Y L, Zheng X, He Y N. Acta Botanica Yunnanica, 1999, 21(4): 497.

[19] Yan H Y. Studies on Chemical Constituents of Oxytropis Falcata Bunge and Cleroderdrun Bugei Stued, 2007, Xi’an: Northwest Normal University.

[20] Lü M, Su Y F, Gao Y, Song D B, Gao X M, Zhang B L. Chinese Traditional and Herbal Drugs, 2009, 40(3): 356.

[21] Tomimori T, Imoto Y, Ishida M, Kizu H, Namba T. Journal of the Pharmaceutical Society of Japan, 1998, 42(1): 98.

[22] Xu X Y, Xie H H, Jiang Y M, Wei X Y. Journal of Agricultural and Food Chemistry, 2011, 59: 1205.

[23] Kim Y M, Wang M H, Rhee H I. Carbohydr. Res., 2004, 339: 715.