Crambescidin 826 and dehydrocrambine A:: New polycyclic guanidine alkaloids from the marine sponge Monanchora sp that inhibit HIV-1 fusion

被引：84

作者：

Chang, LC ^{[1
]}

Whittaker, NF ^{[1
]}

Bewley, CA ^{[1
]}

机构：

[1] NIDDKD, Bioorgan Chem Lab, NIH, DHHS, Bethesda, MD 20892 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 2003年 / 66卷 / 11期

关键词：

D O I：

10.1021/np030256t

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Two new polycyclic guanidine alkaloids, crambescidin 826 (1) and dehydrocrambine A (2), and the known compounds crambescidin 800 (3) and fromiamycalin (4) were isolated from the marine sponge Monanchora sp. The structures of 1 and 2 were elucidated by 2D NMR and mass spectrometry, and relative stereochemistry was established by analysis of coupling constants and ROESY spectra. The pentacyclic guanidine alkaloids 1, 3, and 4 inhibit HIV-1 envelope-mediated fusion in vitro with IC50's of 1-3 muM, while compound 2, a tricyclic guanidine alkaloid, showed weaker inhibition, with an IC50 of similar to35 muM.

引用

页码：1490 / 1494

页数：5

共 23 条

[1] Mirabilins (A-F): New alkaloids from a southern Australian marine sponge, Arenochalina mirabilis [J].

Barrow, RA ;

Murray, LM ;

Lim, TK ;

Capon, RJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1996, 49 (07) :767-773

[2] POLYCYCLIC GUANIDINE ALKALOIDS FROM THE MARINE SPONGE CRAMBE-CRAMBE AND CA++ CHANNEL BLOCKER ACTIVITY OF CRAMBESCIDIN-816 [J].

BERLINCK, RGS ;

BRAEKMAN, JC ;

DALOZE, D ;

BRUNO, I ;

RICCIO, R ;

FERRI, S ;

SPAMPINATO, S ;

SPERONI, E .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07) :1007-1015

[3] 2 NEW GUANIDINE ALKALOIDS FROM THE MEDITERRANEAN SPONGE CRAMBE-CRAMBE [J].

BERLINCK, RGS ;

BRAEKMAN, JC ;

DALOZE, D ;

HALLENGA, K ;

OTTINGER, R ;

BRUNO, I ;

RICCIO, R .

TETRAHEDRON LETTERS, 1990, 31 (45) :6531-6534

[4] Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora [J].

Braekman, JC ;

Daloze, D ;

Tavares, R ;

Hajdu, E ;

Van Soest, RWM .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (02) :193-196

[5] DESIGN AND SYNTHESIS OF A CD4 BETA-TURN MIMETIC THAT INHIBITS HUMAN-IMMUNODEFICIENCY-VIRUS ENVELOPE GLYCOPROTEIN GP120 BINDING AND INFECTION OF HUMAN-LYMPHOCYTES [J].

CHEN, SX ;

CHRUSCIEL, RA ;

NAKANISHI, H ;

RAKTABUTR, A ;

JOHNSON, ME ;

SATO, A ;

WEINER, D ;

HOXIE, J ;

SARAGOVI, HU ;

GREENE, MI ;

KAHN, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (13) :5872-5876

[6] Engineering a CD4 mimetic inhibiting the binding of the human immunodeficiency virus-1 (HIV-1) envelope glycoprotein gp120 to human lymphocyte CD4 by the transfer of a CD4 functional site to a small natural scaffold [J].

Drakopoulou, E ;

Vizzavona, J ;

Vita, C .

LETTERS IN PEPTIDE SCIENCE, 1998, 5 (2-3) :241-245

[7]

Faulkner DJ, 1999, NAT PROD REP, V16, P155

[8] ON THE STRUCTURES OF CRAMBESCIN-B AND CRAMBESCIN-C1 [J].

JARESERIJMAN, EA ;

INGRUM, AA ;

SUN, FR ;

RINEHART, KL .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (12) :2186-2188

[9] POLYCYCLIC GUANIDINE-CONTAINING COMPOUNDS FROM THE MEDITERRANEAN SPONGE CRAMBE-CRAMBE - THE STRUCTURE OF 13,14,15-ISOCRAMBESCIDIN 800 AND THE ABSOLUTE STEREOCHEMISTRY OF THE PENTACYCLIC GUANIDINE MOIETIES OF THE CRAMBESCIDINS [J].

JARESERIJMAN, EA ;

INGRUM, AL ;

CARNEY, JR ;

RINEHART, KL ;

SAKAI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4805-4808

[10] CRAMBESCIDINS - NEW ANTIVIRAL AND CYTOTOXIC COMPOUNDS FROM THE SPONGE CRAMBE-CRAMBE [J].

JARESERIJMAN, EA ;

SAKAI, R ;

RINEHART, KL .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5712-5715

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