Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents

被引:118
作者
Iwasa, K
Moriyasu, M
Tachibana, Y
Kim, HS
Wataya, Y
Wiegrebe, W
Bastow, KF
Cosentino, LM
Kozuka, M
Lee, KH [1 ]
机构
[1] Univ N Carolina, Sch Pharm, Nat Prod Lab, Chapel Hill, NC 27599 USA
[2] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan
[3] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan
[4] Univ Regensburg, Inst Pharm, D-93040 Regensburg, Germany
[5] Biotech Res Labs Inc, Gaithersburg, MD 20877 USA
关键词
D O I
10.1016/S0968-0896(01)00154-7
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Twenty-six simple isoquinolines and 21 benzylisoquinolines were tested for antimicrobial, antimalarial, cytotoxic, and anti-HIV activities. Some simple isoquinoline alkaloids were significantly active in each assay, and may be useful as lead compounds for developing potential chemotherapeutic agents. These compounds include 13 (antimicrobial), 25, 26, and 42 (antimalarial), 13 and 25 (cytotoxic), and 28 and 29 (anti-HIV). A quaternary nitrogen atom of isoquinolium or dihydroisoquinolinium type may contribute to enhanced potency in the first three types of activities. In contrast, anti-HIV activity was found with tetrahydroisoquinoline and 6,7-dihydroxyisoquinolium salts. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2871 / 2884
页数:14
相关论文
共 32 条
[1]   ANTIMICROBIAL ACTIVITY OF SOME ISOQUINOLINE ALKALOIDS [J].
ABBASOGLU, U ;
SENER, B ;
GUNAY, Y ;
TEMIZER, H .
ARCHIV DER PHARMAZIE, 1991, 324 (06) :379-380
[2]  
ARAI Y, 1968, YAKUGAKU ZASSHI, V64, P97
[3]   CONTINUOUS CULTIVATION OF INTRAERYTHROCYTIC PLASMODIUM-FALCIPARUM IN A SERUM-FREE MEDIUM WITH THE USE OF A GROWTH-PROMOTING FACTOR [J].
ASAHI, H ;
KANAZAWA, T .
PARASITOLOGY, 1994, 109 :397-401
[4]   ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].
BOYD, MR ;
HALLOCK, YF ;
MANFREDI, KP ;
BLUNT, JW ;
MCMAHON, JB ;
BUCKHEIT, RW ;
BRINGMANN, G ;
SCHAFFER, M ;
CRAGG, GM ;
THOMAS, DW ;
JATO, JG ;
CARDELLINA, JH .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745
[5]  
Brossi A., 1993, The Alkaloids: Chemistry and Pharmacology, V43, P119
[6]  
BROSSI A, 1977, ORG SYNTH, V56, P3
[7]   METABOLISM OF SALSOLINOL BY TISSUE-CULTURES OF SOME PAPAVERACEAE [J].
IWASA, K ;
KAMIGAUCHI, M ;
TAKAO, N .
PHYTOCHEMISTRY, 1991, 30 (09) :2973-2975
[8]   Antimalarial activity and structure-activity relationships of protoberberine alkaloids [J].
Iwasa, K ;
Kim, HS ;
Wataya, Y ;
Lee, DU .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (01) :65-69
[9]   Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity [J].
Iwasa, K ;
Nishiyama, Y ;
Ichimaru, M ;
Moriyasu, M ;
Kim, HS ;
Wataya, Y ;
Yamori, T ;
Takashi, T ;
Lee, DU .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (12) :1077-1083
[10]   PLASMODIUM-FALCIPARUM - CONTINUOUS CULTIVATION IN A SEMI-AUTOMATED APPARATUS [J].
JENSEN, JB ;
TRAGER, W ;
DOHERTY, J .
EXPERIMENTAL PARASITOLOGY, 1979, 48 (01) :36-41