Massetolides A−H, Antimycobacterial Cyclic Depsipeptides Produced by Two Pseudomonads Isolated from Marine Habitats

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 3; pp. 223 - 229
• Main Authors: Gerard, Jeff, Lloyd, Richard, Barsby, Todd, Haden, Paul, Kelly, Michael T, Andersen, Raymond J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.1997; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: ACQUIRED IMMUNE DEFICIENCY SYNDROME; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; ANTIBACTERIAL PROPERTIES; Antibiotics (antibacterial agents, antifungal agents); Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; ANTIMICROBIAL PROPERTIES; Applied microbiology; Biological and medical sciences; BRITISH COLUMBIA; CESTODA; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; Chemistry, Medicinal; COLOMBIE BRITANNIQUE; COLUMBIA BRITANICA; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CYCLIC PEPTIDES; ESPECTROMETRIA; ESTRUCTURA QUIMICA; EUCESTODA; Fundamental and applied biological sciences. Psychology; IMMUNODEFICIENCE; IMMUNODEFICIENCY; INMUNODEFICIENCIA; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Marine; MEDICINAL PROPERTIES; Microbial Sensitivity Tests; Microbiology; Mycobacterium - drug effects; MYCOBACTERIUM AVIUM; MYCOBACTERIUM AVIUM COMPLEX; Mycobacterium avium Complex - drug effects; Mycobacterium avium-intracellulare; MYCOBACTERIUM TUBERCULOSIS; Mycobacterium tuberculosis - drug effects; PEPTIDE; PEPTIDES; Peptides, Cyclic - biosynthesis; Peptides, Cyclic - isolation & purification; Peptides, Cyclic - pharmacology; PEPTIDOS; Pharmacology & Pharmacy; Plant Sciences; PROPIEDADES ANTIMICROBIANAS; PROPIEDADES MEDICINALES; PROPRIETE ANTIMICROBIENNE; PROPRIETE PHARMACOLOGIQUE; PSEUDOMONAS; Pseudomonas - drug effects; RHODOPHYCEAE; Rhodophyta - chemistry; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; Spectrometry, Mass, Fast Atom Bombardment; STRUCTURE CHIMIQUE; TUBERCULOSE; TUBERCULOSIS; viscosin; METABOLITES; BACTERIA; BIOSYNTHESIS; Pseudomonadales; Cyclic peptides; Mycobacterium avium; Lactone; Pseudomonas; In vitro; Biological activity; Marine environment; Mycobacterium tuberculosis; Microbial origin; Mycobacteriales; Depsipeptide; Mycobacteriaceae; Bacteria; Pseudomonadaceae; Isolation; Actinomycetes; Antibacterial agent; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9606456

Massetolides A−H (1 − 8), novel cyclic depsipetides, and the known compound viscosin (9) have been isolated from cultures of two Pseudomonas sp. isolated from a marine alga and a marine tube worm, respectively. Massetolide A (1) and viscosin (9) exhibit in vitro antimicrobial activity against Mycobacterium tuberculosis and Mycobacterium avium-intracellulare. Precursor-directed biosynthesis has been used to generate unnatural massetolides 11−13 incorporating nonprotein amino acids.