Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana

被引:69
作者
Chang, YC
Hsieh, PW
Chang, FR
Wu, RR
Liaw, CC
Lee, KH
Wu, YC [1 ]
机构
[1] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan
[2] Kao Yuan Inst Technol, Dept Chem Engn, Kaohsiung, Taiwan
[3] Natl Cheng Kung Univ, Tainan Reg Instrument Ctr, Tainan 70101, Taiwan
[4] Univ N Carolina, Sch Pharm, Nat Prod Lab, Chapel Hill, NC USA
关键词
Argemone mexicana; Papaveraceae; argemexicaine A; argemexicaine B; protopine; benzo[c]phenanthridine; (+/-)-6-acetonyldihydrochelerythrine; anti-HIV activity;
D O I
10.1055/s-2003-37710
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new protopine-type alkaloids, argemexicame A (1) and argemexicame B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[c]phenanthridine (+/-)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 mug/mL and 14.6, respectively.
引用
收藏
页码:148 / 152
页数:5
相关论文
共 23 条
[1]   Topoisomerase I poisons and suppressors as anticancer drugs [J].
Bailly, C .
CURRENT MEDICINAL CHEMISTRY, 2000, 7 (01) :39-58
[2]  
BREITMAIER E, 1987, CARBON 13 NMR SPECTR, P369
[3]   Isoquinoline alkaloids from Argemone mexicana reduce morphine withdrawal in guinea pig isolated ileum [J].
Capasso, A ;
Piacente, S ;
Pizza, C ;
DeTommasi, N ;
Jativa, C ;
Sorrentino, L .
PLANTA MEDICA, 1997, 63 (04) :326-328
[4]  
CHELOMBITKO VA, 1971, PHARMAZIE, V7, P208
[5]  
CHENG YC, 1987, J BIOL CHEM, V262, P2187
[6]   SANGUINARINE - ITS POTENTIAL AS A LIVER TOXIC ALKALOID PRESENT IN THE SEEDS OF ARGEMONE-MEXICANA [J].
DALVI, RR .
EXPERIENTIA, 1985, 41 (01) :77-78
[7]   Benzophenanthridine alkaloids from Zanthoxylum rhoifolium [J].
de Moura, NF ;
Ribeiro, HB ;
Machado, ECS ;
Ethur, EM ;
Zanatta, N ;
Morel, AF .
PHYTOCHEMISTRY, 1997, 46 (08) :1443-1446
[8]  
HIROSHI T, 1985, CHEM PHARM BULL, V33, P4775
[9]  
HSIAO JJ, 1995, PHYTOCHEMISTRY, V39, P899, DOI 10.1016/0031-9422(95)00072-F
[10]   STRUCTURE AND SYNTHESIS OF ARNOTTIN .1. A 6H-BENZO[D]NAPHTHO[1,2-B]PYRAN-6-ONE DERIVATIVE FROM A PLANT SOURCE [J].
ISHII, H ;
ISHIKAWA, T ;
MUROTA, M ;
AOKI, Y ;
HARAYAMA, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1019-1022