Journal of Guangxi Normal University(Natural Science Edition) ›› 2023, Vol. 41 ›› Issue (5): 96-104.doi: 10.16088/j.issn.1001-6600.2022092502

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A New C21 Steroidal Glycoside from Gymnema sylvestre and Its Hypoglycemic Activity

LIU Meiyu1, ZHANG Jinyan1, ZHOU Tongxi2, LIAO Guangfeng1, YANG Xinzhou2*, LU Rumei1*   

  1. 1. College of Pharmacy, Guangxi University of Chinese Medicine, Nanning Guangxi 530000, China;
    2. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan Hubei 430074, China
  • Received:2022-09-25 Revised:2022-11-18 Published:2023-10-09

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Abstract: The chemical constituents of Gymnema sylvestre (Retz.) Schult. were isolated and purified by macroporous adsorption resin, silica gel, Sephadex LH-20 and semipreparative high performance liquid chromatography. Their structures were identified by physicochemical properties and spectral data. Sixteen compounds were isolated and identified as sylvepregoside E (1), gymnepregoside H (2), apigenin (3), luteolin (4), phydroxybenzaldehyde (5), phydroxybenzoic acid (6), cinnamic acid (7), caffeic acid (8), 3, 4-dimethoxycinnamic acid (9), transphydroxycinnamic acid ethyl ester (10), 4-O-β-D-glucopyranosylvanillic acid (11), ochuscin C (12), pinoresinol (13), 4-hydroxy-2-nonenoic acid (14), linolenic acid (15), and linoleic acid (16). Among them, compound 1 was a new compound, compounds 2-16 were isolated from this plant for the first time. The results of biological activity showed that compounds 1 and 2 could significantly promote the glucose uptake of L6 cells, which were 1.79 and 1.95 times higher than that of the blank group, respectively.

Key words: gymnema sylvestre, C21 steroidal glycosides, sylvepregoside E, gymnepregoside H, hypoglycemic

CLC Number:  R284; R285
[1] 《全国中草药汇编》编写组. 全国中草药汇编[M]. 北京: 人民卫生出版社, 1978: 573.
[2] 云南省药材公司. 云南中药资源名录[M]. 北京: 科学出版社, 1993: 434.
[3] 滕红丽, 梅之南. 中国壮药资源名录[M]. 北京: 中医古籍出版社, 2014: 227.
[4] ARUMUGAM R, GOVINDARAJAN S. Histological studies on pancreatic tissue in high fat diet with low multiple dosage of streptozotocin induced type 2 diabetes after Gymnema sylvestre administration[J]. Indian Journal of Public Health, 2019, 10: 917-922. DOI: 10.37506/v10/i12/2019/i-jphrd/192237.
[5] GAYTÁN MARTÍNEZ L A, SÁNCHEZ-RUIZ L A, ZUÑIGA L Y, et al. Effect of Gymnema sylvestre administration on glycemic control, insulin secretion, and insulin sensitivity in patients with impaired glucose tolerance[J]. Journal of Medicinal Food, 2021, 24(1): 28-32. DOI: 10.1089/jmf.2020.0024.
[6] KUMAR P M, VENKATARANGANNA M V, MANJUNATH K, et al. Methanolic leaf extract of Gymnema sylvestre augments glucose uptake and ameliorates insulin resistance by upregulating glucose transporter-4, peroxisome proliferator-activated receptor-gamma, adiponectin, and leptin levels in vitro[J]. Journal of Intercultural Ethnopharmacology, 2016, 5(2): 146-152. DOI: 10.5455/jice.20160224051727.
[7] LI Y M, LIU Y P, LIANG J J, et al. Gymnemic acid ameliorates hyperglycemia through PI3K/AKT- and AMPK-mediated signaling pathways in type 2 diabetes mellitus rats[J]. Journal of Agricultural and Food Chemistry, 2019, 67(47): 13051-13060. DOI: 10.1021/acs.jafc.9b04931.
[8] WANG Y, DAWID C, KOTTRA G, et al. Gymnemic acids inhibit sodium-dependent glucose transporter 1[J]. Journal of Agricultural and Food Chemistry, 2014, 62(25): 5925-5931. DOI: 10.1021/jf501766u.
[9] 詹鑫, 陈李璟, 廖广凤, 等. 萝藦科药用植物中新C21甾体的研究进展(Ⅰ)[J]. 广西师范大学学报(自然科学版), 2021, 39(5): 1-29. DOI: 10.16088/j.issn.1001-6600.2020110903.
[10] KIEM P V, YEN D T H, HUNG N V, et al. Five new pregnane glycosides from Gymnema sylvestre and their α-glucosidase and α-amylase inhibitory activities[J]. Molecules, 2020, 25(11): 2525. DOI: 10.3390/molecules25112525.
[11] LIU M Y, ZHOU T X, ZHANG J Y, et al. Identification of C21 steroidal glycosides from Gymnema sylvestre (Retz.) and evaluation of their glucose uptake activities[J]. Molecules, 2021, 26(21): 6549. DOI: 10.3390/molecules26216549.
[12] LIN Y L, WU Y M, KUO Y H, et al. Pregnane glycosides from Gymnema alternifolium[J]. Journal of the Chinese Chemical Society, 1999, 46(5): 841-846. DOI: 10.1002/jccs.199900114.
[13] 张育浩, 张雄, 张本印, 等. 藏药熏倒牛化学成分研究[J]. 中草药, 2019, 50(7): 1551-1554. DOI:10.7501/j.issn.0253-2670.2019.07.009.
[14] 卢汝梅, 黎云清, 王肖, 等. 民族药龙骨风化学成分研究[J]. 广西师范大学学报(自然科学版), 2020, 38(5): 78-85. DOI: 10.16088/j.issn.1001-6600.2020.05.010.
[15] 侯远鑫, 周昌园, 侯淑芬, 等. 蜈蚣草乙酸乙酯部位化学成分分离鉴定[J]. 中国实验方剂学杂志, 2018, 24(19): 52-55. DOI: 10.13422/j.cnki.syfjx.20181915.
[16] 王淑慧, 程锦堂, 郭丛, 等. 余甘子化学成分研究[J]. 中草药, 2019, 50(20): 4873-4878. DOI: 10.7501/j.issn.0253-2670.2019.20.005.
[17] 杜伟东, 吴蓓, 李志峰, 等. 小花清风藤化学成分的分离与鉴定(Ⅱ)[J]. 中草药, 2019, 50(18): 4277-4280. DOI: 10.7501/j.issn.0253-2670.2019.18.004.
[18] 朱毅. 杜鹃兰的化学成分研究[D]. 武汉: 湖北中医药大学, 2014. DOI: 10.7666/d.Y2569715.
[19] 尚志梅, 成蕾, 刘贵园, 等. 矮石斛化学成分研究[J]. 中草药, 2019, 50(9): 2036-2040. DOI: 10.7501/j.issn.0253-2670.2019.09.005.
[20] 蒋才武, 梁爽, 黄健军. 壮药香艾纳的化学成分研究[J]. 广西师范大学学报(自然科学版), 2012, 30(3): 214-217. DOI: 10.3969/j.issn.1001-6600.2012.03.034.
[21] 秦汝兰, 吕重宁, 于洋, 等. 兴安升麻中酚酸类化学成分的分离与鉴定[J]. 中国实验方剂学杂志, 2019, 25(21): 112-117. DOI: 10.13422/j.cnki.syfjx.20191917.
[22] 朱海林, 王振洲, 郑炳真, 等. 毛酸浆果实的化学成分研究[J]. 中草药, 2016, 47(5): 732-735. DOI: 10.7501/j.issn.0253-2670.2016.05.007.
[23] 延在昊, 成亮, 孔令义, 等. 黑老虎化学成分及其抗氧化活性研究[J]. 中草药, 2013, 44(21): 2969-2973. DOI: 10.7501/j.issn.0253-2670.2013.21.005.
[24] CHEN S S, LIU H X, YE W, et al. Ochuscins A-G, highly oxygenated usnic acid derivatives from the deep-sea-derived fungus Ochroconis sp. FS449[J]. Tetrahedron, 2020, 76(14): 131066. DOI: 10.1016/j.tet.2020.131066.
[25] 储春霞, 黄圣卓, 梅文莉, 等. 辣木茎木脂素类和萜类化学成分及其活性研究[J]. 中草药, 2019, 50(21): 5198-5205. DOI: 10.7501/j.issn.0253-2670.2019.21.010.
[26] 李瑞, 李彦程, 武玉卓, 等. 赤芍水提物化学成分的研究[J]. 中国中药杂志, 2018, 43(14): 2956-2963. DOI: 10.19540/j.cnki.cjcmm.20170512.010.
[27] 董召月, 王红, 马英雄, 等. 波棱瓜子化学成分的研究[J]. 中成药, 2019, 41(2): 341-344. DOI: 10.3969/j.issn.1001-1528.2019.02.020.
[28] 刘慧坤. 匙羹藤酸分离提取及其降血糖功能研究[D]. 天津: 天津科技大学, 2006.
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