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
Barrow, RA
Murray, LM
Lim, TK
Capon, RJ
[J]. 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
BERLINCK, RGS
BRAEKMAN, JC
DALOZE, D
BRUNO, I
RICCIO, R
FERRI, S
SPAMPINATO, S
SPERONI, E
[J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07): : 1007 - 1015
[3] 2 NEW GUANIDINE ALKALOIDS FROM THE MEDITERRANEAN SPONGE CRAMBE-CRAMBE
BERLINCK, RGS
BRAEKMAN, JC
DALOZE, D
HALLENGA, K
OTTINGER, R
BRUNO, I
RICCIO, R
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6531 - 6534
[4] Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora
Braekman, JC
Daloze, D
Tavares, R
Hajdu, E
Van Soest, RWM
[J]. 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
CHEN, SX
CHRUSCIEL, RA
NAKANISHI, H
RAKTABUTR, A
JOHNSON, ME
SATO, A
WEINER, D
HOXIE, J
SARAGOVI, HU
GREENE, MI
KAHN, M
[J]. 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
Drakopoulou, E
Vizzavona, J
Vita, C
[J]. 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
JARESERIJMAN, EA
INGRUM, AA
SUN, FR
RINEHART, KL
[J]. 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
JARESERIJMAN, EA
INGRUM, AL
CARNEY, JR
RINEHART, KL
SAKAI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) : 4805 - 4808
[10] CRAMBESCIDINS - NEW ANTIVIRAL AND CYTOTOXIC COMPOUNDS FROM THE SPONGE CRAMBE-CRAMBE
JARESERIJMAN, EA
SAKAI, R
RINEHART, KL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) : 5712 - 5715

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