A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells

被引：57

作者：

Nguyen Xuan Nhiem ^{[1
,2
]}

Bui Huu Tai ^{[1
,2
]}

Tran Hong Quang ^{[1
,2
]}

Phan Van Kiem ^{[2
]}

Chau Van Minh ^{[2
]}

Nguyen Hoai Nam ^{[2
]}

Kim, Jun-Ho ^{[3
]}

Im, Lee-Rang ^{[3
]}

Lee, Young-Mi ^{[3
]}

Kim, Young Ho ^{[1
]}

机构：

[1] Chungnam Natl Univ, Coll Pharm, Taejon 305764, South Korea

[2] Vietnam Acad Sci & Technol, Inst Marine Biochem, Hanoi, Vietnam

[3] Wonkwang Univ, Coll Pharm, Dept Oriental Pharm, Iksan 570749, Jonbuk, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 06期

关键词：

Centella asiatica; Apiaceae; Ursane-type triterpene glycoside; Asiaticoside G; IL-2; Anti-inflammatory; Nitric oxide; Tumor necrosis factor-alpha; PENTACYCLIC TRITERPENOIDS; ACID; CONSTITUENTS;

D O I：

10.1016/j.bmcl.2011.01.066

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

One new ursane-type triterpenoid glycoside, asiaticoside G (1), five triterpenoids, asiaticoside (2), asiaticoside F (3), asiatic acid (4), quadranoside IV (5), and 2 alpha,3 beta,6 beta-trihydroxyolean-12-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (6), and four flavonoids, kaempferol (7), quercetin (8), astragalin (9), and isoquercetin (10) were isolated from the leaves of Centella asiatica. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. The structure of new compound 1 was determined to be 2 alpha,3 beta,23,30-tetrahydroxyurs-12-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester. The anti-inflammatory activities of the isolated compounds were investigated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Asiaticoside G (1) potently inhibited the production of nitric oxide and tumor necrosis factor-alpha with inhibition rates of 77.3% and 69.0%, respectively, at the concentration of 100 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1777 / 1781

页数：5

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