Isolation and Stereospecific Synthesis of Janolusimide B from a New Zealand Collection of the Bryozoan Bugula flabellata

NMR-directed screening of New Zealand marine organisms has led to the isolation of the modified tripeptide janolusimide B from the common invasive bryozoan Bugula flabellata. The structure was established by NMR and MS analysis, degradative hydrolysis and derivatization, and stereoselective fragment...

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Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 78; no. 3; pp. 530 - 533
Main Authors Wang, Jiayi, Prinsep, Michèle R, Gordon, Dennis P, Page, Michael J, Copp, Brent R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 27.03.2015
Amer Chemical Soc
Subjects
Animals
Bryozoa - chemistry
Bugula flabellata
Chemistry, Medicinal
Janolus cristatus
Life Sciences & Biomedicine
Marine Biology
Molecular Structure
New Zealand
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - isolation & purification
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
New Zealand
PSE, New Zealand
MED
SECONDARY METABOLITES
PTEROCELLINS
NUDIBRANCH
TOXIN
STEREOCHEMISTRY
ALKALOIDS
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Summary:NMR-directed screening of New Zealand marine organisms has led to the isolation of the modified tripeptide janolusimide B from the common invasive bryozoan Bugula flabellata. The structure was established by NMR and MS analysis, degradative hydrolysis and derivatization, and stereoselective fragment synthesis. The bryozoan natural product is an N-methyl analogue of janolusimide, previously reported from the Mediterranean nudibranch Janolus cristatus, a species known to prey upon bryozoa.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0163-3864
1520-6025
DOI:10.1021/np500752y