Sesquiterpene alkaloids from Tripterygium hypoglaucum and Tripterygium wilfordii:: A new class of potent anti-HIV agents

被引:103
作者
Duan, HQ
Takaishi, Y
Imakura, Y
Jia, YF
Li, D
Cosentino, LM
Lee, KH
机构
[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan
[2] Naruto Univ Educ, Fac Sci, Tokushima 7728502, Japan
[3] Shanghai Med Univ, Sch Pharm, Shanghai 200032, Peoples R China
[4] BBI Biotech Res Labs, Gaithersburg, MD 20877 USA
[5] Univ N Carolina, Sch Pharm, Nat Prod Lab, Chapel Hill, NC 27599 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2000年 / 63卷 / 03期
关键词
D O I
10.1021/np990281s
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Five new sesquiterpene pyridine alkaloids [triptonines A (1) and B (2), and wildfordinines A (3), B (4), and C (5)] and two known compounds (peritassine A and hypoglaunine C) were isolated from Tripterygium hypoglaucum and a clinically used extract of Tripterygium wilfordii. The structures of 1-5 were elucidated by spectroscopic methods. The anti-HIV activity of 1, 2, and several related compounds was evaluated. Triptonine B (2) demonstrated potent anti-HIV activity with an EC50 value of <0.10 mu g/mL and an in vitro therapeutic index value of > 1000.
引用
收藏
页码:357 / 361
页数:5
相关论文
共 20 条
[1]   ANTI-AIDS AGENTS .4. TRIPTERIFORDIN, A NOVEL ANTI-HIV PRINCIPLE FROM TRIPTERYGIUM-WILFORDII - ISOLATION AND STRUCTURAL ELUCIDATION [J].
CHEN, K ;
SHI, Q ;
FUJIOKA, T ;
ZHANG, DC ;
HU, CQ ;
JIN, JQ ;
KILKUSKIE, RE ;
LEE, KH .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (01) :88-92
[2]   ANTI-AIDS AGENTS .19. NEOTRIPTERIFORDIN, A NOVEL ANTI-HIV PRINCIPLE FROM TRIPTERYGIUM-WILFORDII - ISOLATION AND STRUCTURAL ELUCIDATION [J].
CHEN, K ;
SHI, QA ;
FUJIOKA, T ;
NAKANO, T ;
HU, CQ ;
JIN, JQ ;
KILKUSKIE, RE ;
LEE, KH .
BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (10) :1345-1348
[3]   NEW MACROLIDE SESQUITERPENE ALKALOIDS OF CATHA-EDULIS - EXAMPLES CONTAINING A NOVEL DILACTONE BRIDGE [J].
CROMBIE, L ;
TOPLIS, D ;
WHITING, DA ;
ROZSA, Z ;
HOHMANN, J ;
SZENDREI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :531-534
[4]   Novel sesquiterpene esters with alkaloid and monoterpene and related compounds from Tripterygium hypoglaucum:: A new class of potent anti-HIV agents [J].
Duan, HQ ;
Takaishi, Y ;
Bando, M ;
Kido, M ;
Imakura, Y ;
Lee, KH .
TETRAHEDRON LETTERS, 1999, 40 (15) :2969-2972
[5]   Structures of sesquiterpene polyol alkaloids from Tripterygium hypoglaucum [J].
Duan, HQ ;
Takaishi, Y .
PHYTOCHEMISTRY, 1998, 49 (07) :2185-2189
[6]   Sesquiterpene alkaloids from Tripterygium hypoglaucum [J].
Duan, HQ ;
Kawazoe, K ;
Takaishi, Y .
PHYTOCHEMISTRY, 1997, 45 (03) :617-621
[7]   Sesquiterpene evoninate alkaloids from Tripterygium hypoglaucum [J].
Duan, HQ ;
Takaishi, Y .
PHYTOCHEMISTRY, 1999, 52 (08) :1735-1738
[8]   ANTI-AIDS AGENTS .11. BETULINIC ACID AND PLATANIC ACID AS ANTI-HIV PRINCIPLES FROM SYZIGIUM-CLAVIFLORUM, AND THE ANTI-HIV ACTIVITY OF STRUCTURALLY RELATED TRITERPENOIDS [J].
FUJIOKA, T ;
KASHIWADA, Y ;
KILKUSKIE, RE ;
COSENTINO, LM ;
BALLAS, LM ;
JIANG, JB ;
JANZEN, WP ;
CHEN, IS ;
LEE, KH .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (02) :243-247
[9]   A NONPROMOTING PHORBOL FROM THE SAMOAN MEDICINAL PLANT HOMALANTHUS-NUTANS INHIBITS CELL KILLING BY HIV-1 [J].
GUSTAFSON, KR ;
CARDELLINA, JH ;
MCMAHON, JB ;
GULAKOWSKI, RJ ;
ISHITOYA, J ;
SZALLASI, Z ;
LEWIN, NE ;
BLUMBERG, PM ;
WEISLOW, OS ;
BEUTLER, JA ;
BUCKHEIT, RW ;
CRAGG, GM ;
COX, PA ;
BADER, JP ;
BOYD, MR .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :1978-1986
[10]   ANTI-AIDS AGENTS .8. HIV AND REVERSE-TRANSCRIPTASE INHIBITION BY TANNINS [J].
KILKUSKIE, RE ;
KASHIWADA, Y ;
NONAKA, G ;
NISHIOKA, I ;
BODNER, AJ ;
CHENG, YC ;
LEE, KH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (12) :1529-1534