Diterpenoid lead stevioside and its hydrolysis products steviol and isosteviol: Biological activity and structural modification

被引：62

作者：

Wang, Mingying ^{[1
]}

Li, He ^{[1
]}

Xu, Fanxing ^{[1
]}

Gao, Xiang ^{[1
]}

Li, Jia ^{[1
]}

Xu, Shengtao ^{[2
]}

Zhang, Dayong ^{[2
]}

Wu, Xiaoming ^{[2
]}

Xu, Jinyi ^{[2
]}

Hua, Huiming ^{[1
]}

Li, Dahong ^{[1
]}

机构：

[1] Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Minist Educ, Key Lab Struct Based Drug Design & Discovery, 103 Wenhua Rd, Shenyang 110016, Peoples R China

[2] China Pharmaceut Univ, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2018年 / 156卷

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Stevioside; Steviol; Isosteviol; Medicinal chemistry; Lead exploration; NF-KAPPA-B; CYTOTOXIC ACTIVITY EVALUATION; REBAUDIANA GLYCOSIDE STEVIOLBIOSIDE; ASYMMETRIC ALDOL REACTION; KAURENE-TYPE ORIDONIN; ANTITUBERCULOSIS ACTIVITY; ENT-KAURANE; BREAST-CANCER; STEREOSELECTIVE-SYNTHESIS; MACROCYCLIC DERIVATIVES;

D O I：

10.1016/j.ejmech.2018.07.052

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The diterpenoids present highly varied oxidation patterns subjected to fascinating skeletal rearrangements, and possess antitumor, antibacterial, antihyperglycemic, anti-inflammatory activities and so on. While total synthesis is a possible solution to obtain required diterpenoid derivatives, the need for multisteps to build complex "privileged structures" is always prohibitive by semi-synthesis from naturally abundant related molecules. From this perspective, stevioside and its hydrolysis products steviol and isosteviol are good leads in the field of medicinal chemistry for diterpenoid drug discovery. Stevioside has a complex diterpenoid glycoside molecule comprised of an aglycone, steviol with the entkaurane skeleton and three molecules of glucose. Hydrolyzed under alkaline or acidic condition, stevioside generates ent-kaurane diterpenoid steviol or ent-beyerane diterpenoid isosteviol, respectively. Except for direct applications, they are widely used to provide ent-kaurane or ent-beyerane core structures for further medicinal chemistry study. Besides, these molecules also serve as model molecules, starting materials or catalysts in the field of synthetic chemistry. In this review, their biological activities and medicinal chemistry work are comprehensively summarized which are very helpful for diterpenoid drug exploration. (C) 2018 Elsevier Masson SAS. All rights reserved.

引用

页码：885 / 906

页数：22

共 179 条

[1] In Vitro Antibacterial, Antifungal, Antibiofilm, Antioxidant, and Anticancer Properties of Isosteviol Isolated from Endangered Medicinal Plant Pittosporum tetraspermum [J].