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Literature DB >> 12880326

The isolation and structure elucidation of Tasiamide B, a 4-amino-3-hydroxy-5-phenylpentanoic acid containing peptide from the marine Cyanobacterium Symploca sp.

Philip G Williams¹, Wesley Y Yoshida, Richard E Moore, Valerie J Paul.

Abstract

A new cytotoxic peptide, which displayed an IC(50) value of 0.8 microM against KB cells, has been isolated from the marine cyanobacterium Symploca sp. The planar structure of tasiamide B (1), deduced by 2D NMR experiments, contains the unusual amino acid-derived residue 4-amino-3-hydroxy-5-phenylpentanoic acid (Ahppa). The configuration of 1 was deduced by HPLC analysis of degradation products.

Entities: Chemical

Mesh：

Substances：
Oligopeptides
tasiamide B

Year: 2003 PMID： 12880326 DOI： 10.1021/np030114z

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

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Cited

19 in total

1. Grassystatins D-F, Potent Aspartic Protease Inhibitors from Marine Cyanobacteria as Potential Antimetastatic Agents Targeting Invasive Breast Cancer.

Authors: Fatma H Al-Awadhi; Brian K Law; Valerie J Paul; Hendrik Luesch
Journal: J Nat Prod Date: 2017-10-31 Impact factor: 4.050

The isolation and structure elucidation of Tasiamide B, a 4-amino-3-hydroxy-5-phenylpentanoic acid containing peptide from the marine Cyanobacterium Symploca sp.

1. Grassystatins D-F, Potent Aspartic Protease Inhibitors from Marine Cyanobacteria as Potential Antimetastatic Agents Targeting Invasive Breast Cancer.

Review 2. Biological targets and mechanisms of action of natural products from marine cyanobacteria.

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

4. Stictamides A-C, MMP12 inhibitors containing 4-amino-3-hydroxy-5-phenylpentanoic acid subunits.

5. A simple microscale method for determining the relative stereochemistry of statine units.

6. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation.

7. Grassypeptolides as natural inhibitors of dipeptidyl peptidase 8 and T-cell activation.

Review 8. Targeting eukaryotic proteases for natural products-based drug development.

9. Tasiamide F, a potent inhibitor of cathepsins D and E from a marine cyanobacterium.

Review 10. Marine cyanobacteria compounds with anticancer properties: a review on the implication of apoptosis.