Biginkgosides A-I, Unexpected Minor Dimeric Flavonol Diglycosidic Truxinate and Truxillate Esters from Ginkgo biloba Leaves and Their Antineuroinflammatory and Neuroprotective Activities

被引：54

作者：

Ma, Guang-Lei ^{[1
]}

Xiong, Juan ^{[1
]}

Yang, Guo-Xun ^{[1
]}

Pan, Li-Long ^{[2
]}

Hu, Chang-Ling ^{[1
]}

Wang, Wei ^{[3
]}

Fan, Hui ^{[4
]}

Zhao, Qiu-Hua ^{[4
]}

Zhang, Hai-Yan ^{[3
]}

Hu, Jin-Feng ^{[1
]}

机构：

[1] Fudan Univ, Sch Pharm, Dept Nat Prod Chem, 826 Zhangheng Rd, Shanghai 201203, Peoples R China

[2] Fudan Univ, Sch Pharm, Dept Pharmacol, 826 Zhangheng Rd, Shanghai 201203, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China

[4] E China Normal Univ, Sch Chem & Mol Engn, 500 Dongchuan Rd, Shanghai 200241, Peoples R China

来源：

JOURNAL OF NATURAL PRODUCTS | 2016年 / 79卷 / 05期

关键词：

ACID-DERIVATIVES; CINNAMIC ACID; INFLAMMATION; PHOTODIMERS; GLYCOSIDES; EXTRACT; DISEASE; IDENTIFICATION; OPTIMIZATION; CONSTITUENTS;

D O I：

10.1021/acs.jnatprod.6b00061

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Nine unexpected new flavonol glycoside cyclodimers in the truxinate (1-7, biginkgosides A G, respectively) or trwdllate [biginkgosides H (8) and I (9)] forms were isolated as minor components from the extract of Ginkgo biloba leaves. The new dimers possess an unusual cyclobutane ring formed by a [2+2]-cycloaddition between two symmetric (for compounds 1-5 and 7-9) or nonsymmetric (for 6) flavonol coumaroyl glucorhamnosides. A plausible biosynthetic pathway for these new compounds based on the frontier molecular orbital theory of cycloaddition reactions is briefly discussed. An antineuroinflammatory screening revealed that biginkgosides E (5) and H (8) inhibited nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells, with IC50 values of 2.91 and 17.23 mu M, respectively. Additionally, biginkgoside F (6) showed a significant neuroprotective effect (34.3% increase in cell viability at 1 mu M) against A beta(25-35)-induced cell viability decrease in SH-SY5Y neuroblastoma cells.

引用

页码：1354 / 1364

页数：11