Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase

被引：40
作者：
Gray, Christopher A.
de Lira, Simone P.
Silva, Marcio
Pimenta, Eli F.
Thiemann, Otavio H.
Oliva, Glaucius
Hajdu, Eduardo
Andersen, Raymond J.
Berlinck, Roberto G. S.
机构：
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
[3] Univ British Columbia, Dept Earth & Ocean Sci, Vancouver, BC V6T 1Z1, Canada
[4] Univ Sao Paulo, Inst Fis Sao Carlos, Sao Carlos, SP, Brazil
[5] Univ Fed Rio de Janeiro, Museu Nacl, BR-20940040 Rio De Janeiro, RJ, Brazil
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 23期
关键词：
D O I：
10.1021/jo060295k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new disulfated meroterpenoids, ilhabelanol (1), ilhabrene (2), and isoakaterpin (3), have been isolated from extracts of the Brazilian marine sponge Callyspongia sp. Isoakaterpin (3) inhibits Leishmania spp. adenosine phosphoribosyl transferase with an IC50 of 1.05 mu M. The structures of 1, 2, and 3 were elucidated by analysis of one- and two-dimensional NMR data. Ilhabelanol (1) and ilhabrene (2) both have unprecedented meroterpenoid carbon skeletons.
引用
收藏
页码：8685 / 8690
页数：6
相关论文
共 23 条
[1]   Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the suriname rain forest [J].
Abdel-Kader, M ;
Berger, JM ;
Slebodnick, C ;
Hoch, J ;
Malone, S ;
Wisse, JH ;
Werkhoven, MCM ;
Mamber, S ;
Kingston, DGI .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (01) :11-15
[2]   Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (-)-ambrox and (+)-zonarol [J].
Akita, H ;
Nozawa, M ;
Shimizu, H .
TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1789-1799
[3]   Adociasulfate 10, a new merohexaprenoid sulfate from the sponge Haliclona (aka Adocia) sp. [J].
Blackburn, CL ;
Faulkner, DJ .
TETRAHEDRON, 2000, 56 (43) :8429-8432
[4]   Adociasulfates 1-6, inhibitors of kinesin motor proteins from the sponge Haliclona (aka Adocia) sp. [J].
Blackburn, CL ;
Hopmann, C ;
Sakowicz, R ;
Berdelis, MS ;
Goldstein, LSB ;
Faulkner, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5565-5570
[5]   Synthesis of Ambroxo® from labdanolic acid [J].
Castro, JM ;
Salido, S ;
Altarejos, J ;
Nogueras, M ;
Sánchez, A .
TETRAHEDRON, 2002, 58 (29) :5941-5949
[6]   Plant natural products with leishmanicidal activity [J].
Chan-Bacab, MJ ;
Peña-Rodríguez, LM .
NATURAL PRODUCT REPORTS, 2001, 18 (06) :674-688
[7]   Leishmaniasis - current chemotherapy and recent advances in the search for novel drugs [J].
Croft, SL ;
Coombs, GH .
TRENDS IN PARASITOLOGY, 2003, 19 (11) :502-508
[8]   Chemotherapy of trypanosomiases and leishmaniasis [J].
Croft, SL ;
Barrett, MP ;
Urbina, JA .
TRENDS IN PARASITOLOGY, 2005, 21 (11) :508-512
[9]   Drugs against leishmaniasis: a synergy of technology and partnerships [J].
Davis, AJ ;
Murray, HW ;
Handman, E .
TRENDS IN PARASITOLOGY, 2004, 20 (02) :73-76
[10]   Akaterpin, a novel bioactive triterpene from the marine sponge Callyspongia sp. [J].
Fukami, A ;
Ikeda, Y ;
Kondo, S ;
Naganawa, H ;
Takeuchi, T ;
Furuya, S ;
Hirabayashi, Y ;
Shimoike, K ;
Hosaka, S ;
Watanabe, Y ;
Umezawa, K .
TETRAHEDRON LETTERS, 1997, 38 (07) :1201-1202
123