Homophymine A, an Anti-HIV Cyclodepsipeptide from the Sponge <i>Homophymia</i> sp.

Zampella, Angela; Sepe, Valentina; Luciano, Paolo; Bellotta, Filomena; Monti, Maria Chiara; D’Auria, Maria Valeria; Jepsen, Trine; Petek, Sylvain; Adeline, Marie-Thérèse; Laprévôte, Olivier; Aubertin, Anne-Marie; Debitus, Cécile; Poupat, C.; Ahond, A.

doi:10.1021/jo800583b

Cited by 107 publications

(70 citation statements)

References 38 publications

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“…This b-branched framework, which characterizes all the members of this new class of non-ribosomal cyclodepsipeptides 5 , comprises the following: a 22-or a 25-membered macrolactone; the presence of complex and rare amino acids; a branching position occupied by a D-allo-b-hydroxy-a-amino acid acylated by the unique (2S,3S,4R)-3,4-dimethylglutamine (diMeGln) residue; and an N-terminus coupled to a saturated or unsaturated b-hydroxy acid. Examples of members of this family include callipeltin A 6 , papuamides 7,8 , neamphamides [9][10][11] , theopapuamides 12,13 , mirabamides 14,15 and homophymines 16,17 . Of note, all of them show relevant therapeutic profiles, mostly including potent cytotoxic and anti-HIV activities.…”

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confidence: 99%

The first total synthesis of the cyclodepsipeptide pipecolidepsin A

et al. 2013

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Pipecolidepsin A is a head-to-side-chain cyclodepsipeptide isolated from the marine sponge Homophymia lamellosa. This compound shows relevant cytotoxic activity in three human tumour cell lines and has unique structural features, with an abundance of non-proteinogenic residues, including several intriguing amino acids. Although the moieties present in the structure show high synthetic difficulty, the cornerstone is constituted by the unprecedented and highly hindered g-branched b-hydroxy-a-amino acid D-allo-(2R,3R,4R)-2-amino-3-hydroxy-4,5-dimethylhexanoic acid (AHDMHA) residue, placed at the branching ester position and surrounded by the four demanding residues L-(2S,3S,4R)-3,4-dimethylglutamine, (2R,3R,4S)-4,7-diamino-2,3-dihydroxy-7-oxoheptanoic acid, D-allo-Thr and L-pipecolic acid. Here we describe the first total synthesis of a D-allo-AHDMHA-containing peptide, pipecolidepsin A, thus allowing chemical structure validation of the natural product and providing a robust synthetic strategy to access other members of the relevant head-to-side-chain family in a straightforward manner.

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confidence: 99%

The first total synthesis of the cyclodepsipeptide pipecolidepsin A

et al. 2013

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“…The marine peptides have been found to mainly inhibit viral entry through membrane fusion (Plaza et al, 2007 and2009;Zampella et al, 2008;Oku et al, 2004). The present study showed that a peptide isolated from S. maxima (SM-peptide) is noncytotoxic and inhibits HIV-1 IIIB -induced cell lysis, reverse transcriptase activity, and viral p24 antigen production.…”

Section: Discussionmentioning

confidence: 61%

A Spirulina maxima-derived peptide inhibits HIV-1 infection in a human T cell line MT4

Jang

Park

2016

Fish Aquatic Sci

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Human immunodeficiency virus (HIV) is the causative agent of acquired immune deficiency syndrome (AIDS). Anti-HIV agents targeting various steps in HIV life cycle have been developed; however, so far, no effective drugs have been found. We show here that a peptide isolated from Spirulina maxima (SM-peptide) inhibits HIV-1 infection in a human T cell line MT4. SM-peptide inhibited HIV-1 IIIB -induced cell lysis with a half-maximal inhibitory concentration (IC 50 ) of 0.691 mM, while its 50 % cytotoxic concentration (CC 50 ) was greater than 1.457 mM. Furthermore, the SMpeptide inhibited the HIV-1 reverse transcriptase activity and p24 antigen production. This suggests that SM-peptide is a novel candidate peptide, which may be developed as a therapeutic agent for acquired immunodeficiency syndrome patients.

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“…Homophymine A contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethyloctanoic acid moiety. In a cell-based XTT assay, homophymine A exhibited cytoprotective activity against HIV-1 infection with a IC50 of 75 nM 70 .…”

Section: Anti-hiv Peptidesmentioning

confidence: 99%

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2012

IJPSR

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Marine sponges, the sessile invertebrates of the Phylum porifera are invaluable tool in current research. They remain as a goldmine to chemist and pharmacologist due to its defensive weapons, the secondary metabolites. Endogenous peptides from marine sponges and associated microorganisms are promising lead compound for drug development. Some of the compounds are under clinical trials. These peptides can act against variety of diseases in humans including bacterial, fungal, protozoan, HIV, inflammatory and even tumor. This review focuses on sponge symbiotic association with other organisms, significance of peptides as secondary metabolites and its pharmacological effects by highlighting its role as antbacterial, anti-fungal, anti-HIV and anti-tumor agents. Sponge-microbial associations are found to be very specific in the production of particular bioactive compounds.

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Homophymine A, an Anti-HIV Cyclodepsipeptide from the Sponge Homophymia sp.

Cited by 107 publications

References 38 publications

The first total synthesis of the cyclodepsipeptide pipecolidepsin A

The first total synthesis of the cyclodepsipeptide pipecolidepsin A

A Spirulina maxima-derived peptide inhibits HIV-1 infection in a human T cell line MT4

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