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Literature DB >> 21280591

Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa.

Zhenyu Lu¹, Ryan M Van Wagoner, Mary Kay Harper, Heather L Baker, John N A Hooper, Carole A Bewley, Chris M Ireland.

Abstract

Four new depsipeptides, mirabamides E-H (1-4), and the known depsipeptide mirabamide C (5) have been isolated from the sponge Stelletta clavosa, collected from the Torres Strait. The planar structures were determined on the basis of extensive 1D and 2D NMR and HRESIMS. The absolute configurations were established by the advanced Marfey's method, NMR, and GC-MS. The four new compounds all showed strong inhibition of HIV-1 in a neutralization assay with IC(50) values of 121, 62, 68, and 41 nM, respectively.

Entities: CellLine Chemical Disease Gene Species

Mesh：

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Year: 2011 PMID： 21280591 PMCID： PMC3072293 DOI： 10.1021/np100613p

Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050

10 in total

1. Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion.

Authors: Alberto Plaza; Elena Gustchina; Heather L Baker; Michelle Kelly; Carole A Bewley
Journal: J Nat Prod Date: 2007-10-27 Impact factor: 4.050

2. Total synthesis and structure assignment of papuamide B, a potent marine cyclodepsipeptide with anti-HIV properties.

Authors: Weiqing Xie; Derong Ding; Weiwei Zi; Guangyu Li; Dawei Ma
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Characterization of antibody responses elicited by human immunodeficiency virus type 1 primary isolate trimeric and monomeric envelope glycoproteins in selected adjuvants.

Authors: Y Li; K Svehla; N L Mathy; G Voss; J R Mascola; R Wyatt
Journal: J Virol Date: 2006-02 Impact factor: 5.103

4. Complete stereochemistry of neamphamide A and absolute configuration of the beta-methoxytyrosine residue in papuamide B.

Authors: Naoya Oku; Ravi Krishnamoorthy; Alan G Benson; Robert L Ferguson; Mark A Lipton; Lawrence R Phillips; Kirk R Gustafson; James B McMahon
Journal: J Org Chem Date: 2005-08-19 Impact factor: 4.354

5. Human immunodeficiency virus type 1 env clones from acute and early subtype B infections for standardized assessments of vaccine-elicited neutralizing antibodies.

Authors: Ming Li; Feng Gao; John R Mascola; Leonidas Stamatatos; Victoria R Polonis; Marguerite Koutsoukos; Gerald Voss; Paul Goepfert; Peter Gilbert; Kelli M Greene; Miroslawa Bilska; Denise L Kothe; Jesus F Salazar-Gonzalez; Xiping Wei; Julie M Decker; Beatrice H Hahn; David C Montefiori
Journal: J Virol Date: 2005-08 Impact factor: 5.103

6. Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi.

Authors: Naoya Oku; Kirk R Gustafson; Laura K Cartner; Jennifer A Wilson; Nobuharu Shigematsu; Sonja Hess; Lewis K Pannell; Michael R Boyd; James B McMahon
Journal: J Nat Prod Date: 2004-08 Impact factor: 4.050

7. Cyclodepsipeptides from marine sponges: natural agents for drug research.

Authors: Gowri Shankar Bagavananthem Andavan; Rosa Lemmens-Gruber
Journal: Mar Drugs Date: 2010-03-22 Impact factor: 5.118

8. Using a kinase screen to investigate the constituents of the sponge Stelletta clavosa obtained from diverse habitats.

Authors: Christopher J Wegerski; Dennis France; Susan Cornell-Kennon; Phillip Crews
Journal: Bioorg Med Chem Date: 2004-11-01 Impact factor: 3.641

9. New dimeric macrolide glycosides from the marine sponge Myriastra clavosa.

Authors: Karen L Erickson; Kirk R Gustafson; Lewis K Pannell; John A Beutler; Michael R Boyd
Journal: J Nat Prod Date: 2002-09 Impact factor: 4.050

10. Isotactic polymethoxydienes from the Philippines sponge Myriastra clavosa.

Authors: M Rama Rao; D John Faulkner
Journal: J Nat Prod Date: 2002-08 Impact factor: 4.050

10 in total

21 in total

1. Papuamides E and F, Cytotoxic Depsipeptides from the Marine Sponge Melophlus sp.

Authors: Pritesh Prasad; William Aalbersberg; Klaus-D Feussner; Ryan M Van Wagoner
Journal: Tetrahedron Date: 2011-11-04 Impact factor: 2.457

2. Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

Authors: Zhenjian Lin; Malem Flores; Imelda Forteza; Niel M Henriksen; Gisela P Concepcion; Gary Rosenberg; Margo G Haygood; Baldomero M Olivera; Alan R Light; Thomas E Cheatham; Eric W Schmidt
Journal: J Nat Prod Date: 2012-03-22 Impact factor: 4.050

Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa.

1. Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion.

2. Total synthesis and structure assignment of papuamide B, a potent marine cyclodepsipeptide with anti-HIV properties.

3. Characterization of antibody responses elicited by human immunodeficiency virus type 1 primary isolate trimeric and monomeric envelope glycoproteins in selected adjuvants.

4. Complete stereochemistry of neamphamide A and absolute configuration of the beta-methoxytyrosine residue in papuamide B.

5. Human immunodeficiency virus type 1 env clones from acute and early subtype B infections for standardized assessments of vaccine-elicited neutralizing antibodies.

6. Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi.

7. Cyclodepsipeptides from marine sponges: natural agents for drug research.

8. Using a kinase screen to investigate the constituents of the sponge Stelletta clavosa obtained from diverse habitats.

9. New dimeric macrolide glycosides from the marine sponge Myriastra clavosa.

10. Isotactic polymethoxydienes from the Philippines sponge Myriastra clavosa.

1. Papuamides E and F, Cytotoxic Depsipeptides from the Marine Sponge Melophlus sp.

2. Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

Review 3. Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

4. Stellettapeptins A and B, HIV-inhibitory cyclic depsipeptides from the marine sponge Stelletta sp.

5. Mandelalides A-D, cytotoxic macrolides from a new Lissoclinum species of South African tunicate.

Review 6. Marine natural products targeting the eukaryotic cell membrane.

7. Synthesis of complex head-to-side-chain cyclodepsipeptides.

8. Swinhopeptolides A and B: Cyclic Depsipeptides from the Sponge Theonella swinhoei That Inhibit Ras/Raf Interaction.

9. Biosynthetic chlorination of the piperazate residue in kutzneride biosynthesis by KthP.

Review 10. Natural products from the Lithistida: a review of the literature since 2000.