柳叶五层龙正丁醇提取部分中的3个新酚性成分及其α-葡萄糖苷酶抑制活性

doi:10.7503/cjcu20180622

高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (3): 456.doi: 10.7503/cjcu20180622

柳叶五层龙正丁醇提取部分中的3个新酚性成分及其α-葡萄糖苷酶抑制活性

张隽荣, 尤慧梅, 井宇星, 赵佳文, 王韦, 刘文星, 周敏(), 江志勇()

民族药资源化学国家民委-教育部重点实验室, 云南民族大学民族医药学院, 昆明 650500

收稿日期:2019-09-10 出版日期:2019-01-12 发布日期:2019-01-12
作者简介:
联系人简介: 周敏, 男, 博士, 副教授, 主要从事天然药物化学方面的研究. E-mail: zhouminynun@163.com; 江志勇, 男, 博士, 教授, 主要从事天然药物化学方面的研究. E-mail: jiangzy2010@163.com
基金资助:
国家自然科学基金(批准号: 81560708)和云南省中青年学术技术带头人后备人才计划项目(批准号: 2015HB050)资助.

Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities^†

ZHANG Juanrong, YOU Huimei, JING Yuxing, ZHAO Jiaowen, WANG Wei, LIU Wenxing, ZHOU Min^*(), JIANG Zhiyong^*()

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education,School of Ethnic Medicine, Yunnan Minzu University, Kunming 650500, China

Received:2019-09-10 Online:2019-01-12 Published:2019-01-12
Contact: ZHOU Min,JIANG Zhiyong E-mail:zhouminynun@163.com;jiangzy2010@163.com
Supported by:
† Supported by the National Natural Science Foundation of China(No.81560708) and the Reserve Talent Project of Middle and Young Academic Leaders in Yunnan Province, China(No.2015HB050).

摘要/Abstract

摘要：

采用多种色谱分离方法从柳叶五层龙(Salacia cochinchinensis Lour)的茎叶中分离得到5个化合物. 通过一维(1D)及二维核磁共振波谱(2D NMR), 包括核磁共振氢谱(¹H NMR)、核磁共振碳谱(¹³C NMR)、异核单量子相关(HSQC)、异核多键相关(HMBC)、氢氢相关(¹H-¹H COSY)和旋转坐标中的欧沃豪斯增强光谱(ROESY), 以及红外光谱(IR)和电喷雾电离高分辨质谱(ESI-HRMS)等方法, 鉴定其结构分别为Salaciacochinoside A(1), 5'-O-3,4,5-trimethoxybenzoyl-β-D-apiofuranoside(2), 5-methoxy-anticerol A(3), 21α,30-dihydroxy-D∶A-friedooleanan-3-one(4)和21α,26-dihydroxyfriedelan-3-one(5). 化合物1~3为新化合物. α-葡萄糖苷酶抑制活性测试结果显示, 化合物1和3对α-葡萄糖苷酶具有显著的抑制作用, 其IC₅₀值分别为0.32和0.59 μmol/L; 化合物2, 4和5未表现出α-葡萄糖苷酶抑制活性.

关键词: 柳叶五层龙, 酚性成分, α-葡萄糖苷酶抑制活性;

Abstract:

Five compounds were isolated from the stems and leaves of Salacia cochinchinensis Lour. By comprehensive spectroscopic analyses including mass spectroscopy(MS), infrared radiation(IR), 1D and 2D nuclear magnetic resonance(NMR) [heteronuclear single quantum coherence(HSQC), heteronuclear multiple bond correlation(HMBC), ¹H-¹H chemical-shift correlation spectroscopy(¹H-¹H COSY) and rotating frame overhauser effect spectroscopy(ROESY)], their structures were elucidated as Salaciacochinoside A(1), 5'-O-3,4,5-trimethoxybenzoyl-β-D-apiofuranoside(2), 5-methoxy-anticerol A(3), 21α,30-dihydroxy-D∶A-friedooleanan-3-one(4) and 21α,26-dihydroxyfriedelan-3-one(5), respectively. Compounds 1—3 were new compounds. All the compounds were assayed for the anti-diabetic activities. Compounds 1 and 3 exhibited remarkable bioactivity, inhibiting α-glucosidase with IC₅₀ values of 0.32 and 0.59 μmol/L, respectively. Compounds 2, 4 and 5 showed none anti-diabetic activity in current experiment.

Key words: Salacia cochinchinensis, Phenolic compound, α-Glucosidase inhibitory activity;

中图分类号:

O629

TrendMD:

张隽荣, 尤慧梅, 井宇星, 赵佳文, 王韦, 刘文星, 周敏, 江志勇. 柳叶五层龙正丁醇提取部分中的3个新酚性成分及其α-葡萄糖苷酶抑制活性. 高等学校化学学报, 2019, 40(3): 456.

ZHANG Juanrong,YOU Huimei,JING Yuxing,ZHAO Jiaowen,WANG Wei,LIU Wenxing,ZHOU Min,JIANG Zhiyong. Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities^†. Chem. J. Chinese Universities, 2019, 40(3): 456.

图/表 5

参考文献 27

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No.	Compound 1		Compound 2		Compound 3
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	129.7, s		121.2, s		140.1, s
2	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
3	149.3, s		149.1, s		154.6, s
4	137.0, s		142.4, s		136.4, s
5	149.3, s		149.1, s		154.6, s
6	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
7	85.8, d	4.30, d(9.1)	168.0, s		75.3, d	4.62, d(5.4)
8	78.1, d	4.06, m			77.5, d	3.68, m
9	17.4, q	1.19, d(6.3)			64.4, t	3.42, dd(11.2, 6.2)
						3.56, dd(11.2, 4.4)
3-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
4-MeO			56.0, q	3.38, s
5-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
1'	99.7, d	4.76, d(7.7)	111.6, d	4.87, d(2.6)	62.3, d	3.75, d(5.0)
2'	81.1, d	3.31, dd(9.4, 7.9)	78.9, d	3.97, d(2.5)	85.0, d	4.00, dd(9.9, 5.0)
3'	75.2, d	3.77, t(9.1)	79.1, s		62.3, d	3.75, d(5.0)
4'	72.0, d	3.59, d(8.8)	75.0, t	3.89, d(9.8)
				4.04, d(9.8)
5'	79.9, d	3.64, m	67.7, t	4.32, s
6'	62.7, t	3.90, dd(12.0, 5.4)
		4.07, m

No.	Compound 1		Compound 2		Compound 3
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	129.7, s		121.2, s		140.1, s
2	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
3	149.3, s		149.1, s		154.6, s
4	137.0, s		142.4, s		136.4, s
5	149.3, s		149.1, s		154.6, s
6	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
7	85.8, d	4.30, d(9.1)	168.0, s		75.3, d	4.62, d(5.4)
8	78.1, d	4.06, m			77.5, d	3.68, m
9	17.4, q	1.19, d(6.3)			64.4, t	3.42, dd(11.2, 6.2)
						3.56, dd(11.2, 4.4)
3-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
4-MeO			56.0, q	3.38, s
5-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
1'	99.7, d	4.76, d(7.7)	111.6, d	4.87, d(2.6)	62.3, d	3.75, d(5.0)
2'	81.1, d	3.31, dd(9.4, 7.9)	78.9, d	3.97, d(2.5)	85.0, d	4.00, dd(9.9, 5.0)
3'	75.2, d	3.77, t(9.1)	79.1, s		62.3, d	3.75, d(5.0)
4'	72.0, d	3.59, d(8.8)	75.0, t	3.89, d(9.8)
				4.04, d(9.8)
5'	79.9, d	3.64, m	67.7, t	4.32, s
6'	62.7, t	3.90, dd(12.0, 5.4)
		4.07, m

Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)	Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)
1	0.32±0.01	4	>20
2	>20	5	>20
3	0.59±0.03	Acarbose	0.13±0.003

Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)	Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)
1	0.32±0.01	4	>20
2	>20	5	>20
3	0.59±0.03	Acarbose	0.13±0.003

柳叶五层龙正丁醇提取部分中的3个新酚性成分及其α-葡萄糖苷酶抑制活性

Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities^†

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柳叶五层龙正丁醇提取部分中的3个新酚性成分及其α-葡萄糖苷酶抑制活性

Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities†

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Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities^†