Lignans from Gymnema Sylvestre
Main Article Content
Abstract
Seven known lignans, tortoside A (1), (+)-syringaresinol (2), (+)-medioresinol (3),
(+)-pinoresinol (4), (+)-lyoniresin-6-yl β-D-glucopyranoside (5), (-)-lyoniresinol 3α-O-β-D-glucopyranoside (6), and (-)-lyoniresinol (7) were isolated from the leaves of Gymnema sylvestre (Retz.) R.Br. ex Schult. Their structures were identified on the basis of spectroscopic evidence and in comparison with those reported in the literature. All compounds were reported from G. sylvestre for the first time.
Keywords:
Gymnema sylvestre, lignan, NMR.
References
[1] P. V. Kiem, D. T. H. Yen, N. V. Hung, N. X. Nhiem, B. H. Tai, D. T. Trang, P. H. Yen, H. D. Manh, C. V. Minh, S. J. Park, J. H. Lee, S. Y. Kim, S. H. Kim, The Anti-glycative Potentials of Pregnane Glycosides from Gymnema sylvestre, Phytochem, Lett., Vol. 38, 2020, pp. 19-24, https://doi.org/10.1016/j.phytol.2020.04.012.
[2] P. V. Kiem, D. T. H. Yen, N. V. Hung, N. X. Nhiem, B. H. Tai, D. T. Trang, P. H. Yen, T. M. Ngoc, C. V. Minh, S. J. Park, J. H. Lee, S. Y. Kim, S. H. Kim, Five New Pregnane Glycosides from Gymnema sylvestre and Their α-glucosidase and α-amylase Inhibitory Activities, Molecules, Vol. 25, No. 11, 2020, pp. 2525, https://doi.org/10.3390/molecules25112525.
[3] D. T. H. Yen, N. V. Toan, B. H. Tai, P. H. Yen, N. X. Nhiem, P. V. Kiem, Oleanane Saponins from Gymnema sylvestre, Vietnam J. Chem., Vol. 57, No. 1, 2019, pp. 39-45.
[4] D. T. H. Yen, V. K. Thu, B. H. Tai, P. H. Yen, N. X. Nhiem, P. V. Kiem, Pregnane Glycosides from Gymnema sylvestre, Vietnam J. Chem., Vol. 57, No. 2, 2019, pp.208-212.
[5] W. Changzeng, J. Zhongjian, Lignan, Phenylpropanoid and Iridoid Glycosides from Pedicularis torta, Phytochemistry, Vol. 45, No. 1, 1997, pp.159-166, https://doi.org/10.1016/S0031-9422(96)00770-4.
[6] X. F. Cai, I. S. Lee, N. T. Dat, G. H. Shen, J. S. Kang, D. H. Kim, K. Y. Ho. Inhibitory Lignans Against NFAT Transcription Factor from Acanthopanax koreanum, Arch. Pharm. Res., Vol. 27, No. 7, 2004, pp.738-741, https://doi.org/10.1007/BF02980142.
[7] F. Abe, T. Yamauchi, 9α-Hydroxypinoresinol, 9α-hydroxymedioresinol and Related Lignans from Allamanda neriifolia, Phytochemistry, Vol. 27, No. 2, 1988, pp. 575-577, https://doi.org/10.1016/0031-9422(88)83144-3.
[8] V. Barbara, S. Otto, W. Hildebert, Synthesiss of Biologically Active Tetrahydtofurofuranlignan-(Syringin, Pinoresinol) Mono - and Bisglucosides, Phytochemistry, Vol. 30, No. 9, 1991, pp. 3087- 3089, https://doi.org/10.1016/S0031-9422(00)98258-X.
[9] B. Alexander, S. Jürgen, P. Andrea, A. Günter, Alkaloidal, Megastigmane and Lignan Glucosides from Antidesma membranaceum (Euphorbiaceae), Eur. J. Org. Chem., Vol. 18, 2001, pp. 3537-3543,
https://doi.org/10.1002/1099-0690(200109)2001:18<3537::AID-EJOC3537>3.0.CO;2-A.
[10] A. Hans, L. Matthias, W. Reiner, G. Mahabir, S. Pablo, New Lignan Glucosides from Stemmadenia minima, Planta Med., Vol. 58, No. 3, 1992, pp. 270-272, https://doi.org/10.1055/s-2006-961451.
[11] O. Kazuyoshi, W. Hisashi, O. Yasuaki, U. Tahan, K. Isao, Indonesia Medicinal Plants, XII, Four Isomeric Lignan-glucosides from the Bark of Aegle marmelos (Rutaceae), Chem, Pharm, Bull, Vol. 42, No. 9, 1994, pp. 1924-1926,
https://doi.org/10.1248/cpb.42.1924
[2] P. V. Kiem, D. T. H. Yen, N. V. Hung, N. X. Nhiem, B. H. Tai, D. T. Trang, P. H. Yen, T. M. Ngoc, C. V. Minh, S. J. Park, J. H. Lee, S. Y. Kim, S. H. Kim, Five New Pregnane Glycosides from Gymnema sylvestre and Their α-glucosidase and α-amylase Inhibitory Activities, Molecules, Vol. 25, No. 11, 2020, pp. 2525, https://doi.org/10.3390/molecules25112525.
[3] D. T. H. Yen, N. V. Toan, B. H. Tai, P. H. Yen, N. X. Nhiem, P. V. Kiem, Oleanane Saponins from Gymnema sylvestre, Vietnam J. Chem., Vol. 57, No. 1, 2019, pp. 39-45.
[4] D. T. H. Yen, V. K. Thu, B. H. Tai, P. H. Yen, N. X. Nhiem, P. V. Kiem, Pregnane Glycosides from Gymnema sylvestre, Vietnam J. Chem., Vol. 57, No. 2, 2019, pp.208-212.
[5] W. Changzeng, J. Zhongjian, Lignan, Phenylpropanoid and Iridoid Glycosides from Pedicularis torta, Phytochemistry, Vol. 45, No. 1, 1997, pp.159-166, https://doi.org/10.1016/S0031-9422(96)00770-4.
[6] X. F. Cai, I. S. Lee, N. T. Dat, G. H. Shen, J. S. Kang, D. H. Kim, K. Y. Ho. Inhibitory Lignans Against NFAT Transcription Factor from Acanthopanax koreanum, Arch. Pharm. Res., Vol. 27, No. 7, 2004, pp.738-741, https://doi.org/10.1007/BF02980142.
[7] F. Abe, T. Yamauchi, 9α-Hydroxypinoresinol, 9α-hydroxymedioresinol and Related Lignans from Allamanda neriifolia, Phytochemistry, Vol. 27, No. 2, 1988, pp. 575-577, https://doi.org/10.1016/0031-9422(88)83144-3.
[8] V. Barbara, S. Otto, W. Hildebert, Synthesiss of Biologically Active Tetrahydtofurofuranlignan-(Syringin, Pinoresinol) Mono - and Bisglucosides, Phytochemistry, Vol. 30, No. 9, 1991, pp. 3087- 3089, https://doi.org/10.1016/S0031-9422(00)98258-X.
[9] B. Alexander, S. Jürgen, P. Andrea, A. Günter, Alkaloidal, Megastigmane and Lignan Glucosides from Antidesma membranaceum (Euphorbiaceae), Eur. J. Org. Chem., Vol. 18, 2001, pp. 3537-3543,
https://doi.org/10.1002/1099-0690(200109)2001:18<3537::AID-EJOC3537>3.0.CO;2-A.
[10] A. Hans, L. Matthias, W. Reiner, G. Mahabir, S. Pablo, New Lignan Glucosides from Stemmadenia minima, Planta Med., Vol. 58, No. 3, 1992, pp. 270-272, https://doi.org/10.1055/s-2006-961451.
[11] O. Kazuyoshi, W. Hisashi, O. Yasuaki, U. Tahan, K. Isao, Indonesia Medicinal Plants, XII, Four Isomeric Lignan-glucosides from the Bark of Aegle marmelos (Rutaceae), Chem, Pharm, Bull, Vol. 42, No. 9, 1994, pp. 1924-1926,
https://doi.org/10.1248/cpb.42.1924