A new triterpene and anti-hepatitis B virus active compounds from Alisma orientalis

被引:117
作者
Jiang, Zhi-Yong
Zhang, Xue-Mei
Zhang, Feng-Xue
Liu, Ni
Zhao, Fang
Zhou, Jun
Chen, Ji-Jun [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Yunnan, Peoples R China
[2] Guangzhou Univ Chinese Tradit Med, Inst Trop Med Sci, Guangzhou, Peoples R China
[3] Chinese Acad Sci, Joint Lab Anti Viral Nat Med, Kunming Branch, Kunming 650204, Yunnan, Peoples R China
关键词
PROTOSTANE-TYPE TRITERPENES; ABSOLUTE STEREOSTRUCTURES; AQUATIC PLANTS; CRUDE DRUGS; RHIZOMA; SESQUITERPENES; CONSTITUENTS; 23-ACETATE; ALISMOXIDE;
D O I
10.1055/s-2006-947178
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new triterpencid named alisol 0 (1) was isolated from the rhizomes of Alisma orientalis, together with six known compounds: alisol A 24-acetate (2), 25-anhydroalisol A (3),13 beta,17 beta-epoxyalisol A (4), alisol B 23-acetate (5), alisol F (6), and alisol F 24-acetate (7). Based on 1D and 2D-NMR data (HMQC, HMBC, COSY, ROESY), the structure of the new compound was deduced to be 11-dehydroxy-12-dehydroalisol F-24-acetate (1). Compounds 2-7 exhibited inhibitory activity in vitro on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line with IC50 values of 2.3,11.0,15.4,14.3, 0.6 and 7.7 mu M, and on HBV e antigen (HBeAg) secretion with IC50 values of 498.1, 17.6, 41.0,19.9, 8.5 and 5.1 mu M, respectively.
引用
收藏
页码:951 / 954
页数:4
相关论文
共 19 条
[1]  
GENG PW, 1988, PHYTOCHEMISTRY, V27, P1161, DOI 10.1016/0031-9422(88)80294-2
[2]   Osthole increases glycosylation of hepatitis B surface antigen and suppresses the secretion of hepatitis B virus in vitro [J].
Huang, RL ;
Chen, CC ;
Huang, YL ;
Hsieh, DJ ;
Hu, CP ;
Chen, CF ;
Chang, CM .
HEPATOLOGY, 1996, 24 (03) :508-515
[3]   Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages:: Absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate [J].
Matsuda, H ;
Kageura, T ;
Toguchida, I ;
Murakami, T ;
Kishi, A ;
Yoshikawa, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (21) :3081-3086
[5]   TERPENOIDS OF ALISMA-ORIENTALE RHIZOME AND THE CRUDE DRUG ALISMATIS RHIZOMA [J].
NAKAJIMA, Y ;
SATOH, Y ;
OHTSUKA, N ;
TSUJIYAMA, K ;
MIKOSHIBA, N ;
IDA, Y ;
SHOJI, J .
PHYTOCHEMISTRY, 1994, 36 (01) :119-127
[6]   SESQUITERPENOIDS .58. ALISMOL AND ALISMOXIDE, SESQUITERPENOIDS OF ALISMA RHIZOMES [J].
OSHIMA, Y ;
IWAKAWA, T ;
HIKINO, H .
PHYTOCHEMISTRY, 1983, 22 (01) :183-185
[7]   Guaiane-type sesquiterpenoids from Alisma orientalis [J].
Peng, GP ;
Tian, G ;
Huang, XF ;
Lou, FC .
PHYTOCHEMISTRY, 2003, 63 (08) :877-881
[8]   Structure of orientanone from Alisma orientalis, a novel sesquiterpene originating from guaiane-type carbon skeleton by isopropyl shift [J].
Peng, GP ;
Lou, FC ;
Huang, XF ;
Tian, G .
TETRAHEDRON, 2002, 58 (44) :9045-9048
[9]  
[彭国平 Peng Guoping], 2002, [天然产物研究与开发, Natural Product R & Da], V14, P5
[10]  
[彭国平 Peng Guoping], 2002, [药学学报, Acta Pharmaceutica Sinica], V37, P950