Anti HIV-1 active Calophyllum coumarins:: Distribution, chemistry, and activity

被引:72
作者
Ishikawa, T [1 ]
机构
[1] Chiba Univ, Fac Pharmaceut Sci, Chiba 2638522, Japan
关键词
dipyranocoumarin; isolation; classification; conformation; stereochemistry;
D O I
10.3987/REV-99-526
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some dipyranocoumarins isolated from Calophyllum genus, Guttiferae (Clusiaceae), show anti HIV-1 activity. The HIV-1 active Calophyllum coumarins such as (+)-calanolide A [(+)-1] and (+)-inophyllum a [(+)-13] have a (2R, 3S, 4S)-2,3-dimethyl-4-chromanol ring as common structural requirements, whereas closely related coumarins were significantly less active or totally inactive. Thus, the stereochemistry of the chromanol ring in Calophyllum coumarins could be responsible for anti HIV-1 activity. Calanolide A [(+)-1] has currently been included in clinical trials. This review describes the distribution, chemistry, and the anti HIV-1 activity of Calophyllum coumarins.
引用
收藏
页码:453 / +
页数:23
相关论文
共 50 条
[1]   2 CHEMICALLY DISTINCT GROUPS OF CALOPHYLLUM SPECIES FROM SRI-LANKA [J].
BANDARA, BMR ;
DHARMARATNE, HRW ;
SOTHEESWARAN, S ;
BALASUBRAMANIAM, S .
PHYTOCHEMISTRY, 1986, 25 (02) :425-428
[2]  
BHUSHAN B, 1975, INDIAN J CHEM, V13, P746
[3]   ANALYSIS OF NONNUCLEOSIDE DRUG-RESISTANT VARIANTS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 REVERSE-TRANSCRIPTASE [J].
BOYER, PL ;
CURRENS, MJ ;
MCMAHON, JB ;
BOYD, MR ;
HUGHES, SH .
JOURNAL OF VIROLOGY, 1993, 67 (04) :2412-2420
[4]   CALOPHYLLUM PRODUCTS .V. A NEW 4-PHENYLCOUMARIN FROM CALOPHYLLUM AUSTRALIANUM FVM VESQ [J].
BRECK, GD ;
STOUT, GH .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :4203-&
[5]   Minor coumarins from Calophyllum teysmannii var. inophylloide and synthesis of cytotoxic calanone derivatives [J].
Cao, SG ;
Wu, XH ;
Sim, KY ;
Tan, BHK ;
Vittal, JJ ;
Pereira, JT ;
Goh, SH .
HELVETICA CHIMICA ACTA, 1998, 81 (08) :1404-1416
[6]   Coumarins from Calophyllum teysmannii [J].
Cao, SG ;
Sim, KY ;
Pereira, J ;
Goh, SH .
PHYTOCHEMISTRY, 1998, 47 (05) :773-777
[7]   RESOLUTION AND COMPARATIVE ANTI-HIV EVALUATION OF THE ENANTIOMERS OF CALANOLIDE-A AND CALANOLIDE-B [J].
CARDELLINA, JH ;
BOKESCH, HR ;
MCKEE, TC ;
BOYD, MR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (09) :1011-1014
[8]  
CAVE A, 1972, J COMPT REND ACAD SC, V275, P1105
[9]   TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-CALANOLIDE-A, A NON-NUCLEOSIDE INHIBITOR OF HIV-1 REVERSE-TRANSCRIPTASE [J].
CHENERA, B ;
WEST, ML ;
FINKELSTEIN, JA ;
DREYER, GB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5605-5606
[10]  
Currens MJ, 1996, J PHARMACOL EXP THER, V279, P652