Tolypocaibols: Antibacterial Lipopeptaibols from a Tolypocladium sp. Endophyte of the Marine Macroalga Spongomorpha arcta

Two new lipopeptaibols, tolypocaibols A (1) and B (2), and the mixed NRPS-polyketide-shikimate natural product maximiscin [(P/M)-3)] were isolated from a Tolypocladium sp. fungal endophyte of the marine alga Spongomorpha arcta. Analysis of NMR and mass spectrometry data revealed the amino acid seque...

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Published inJournal of natural products (Washington, D.C.) Vol. 86; no. 6; pp. 1529 - 1535
Main Authors Morehouse, Nicholas J., Flewelling, Andrew J., Liu, Dennis Y., Cavanagh, Hannah, Linington, Roger G., Johnson, John A., Gray, Christopher A.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 23.06.2023
Amer Chemical Soc
Subjects
Anti-Bacterial Agents - chemistry
Bacteria
Chemistry, Medicinal
Endophytes
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
Seaweed
PEPTAIBOLS
METABOLITE
NATURAL-PRODUCTS
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Summary:Two new lipopeptaibols, tolypocaibols A (1) and B (2), and the mixed NRPS-polyketide-shikimate natural product maximiscin [(P/M)-3)] were isolated from a Tolypocladium sp. fungal endophyte of the marine alga Spongomorpha arcta. Analysis of NMR and mass spectrometry data revealed the amino acid sequences of the lipopeptaibols, which both comprise 11 residues with a valinol C-terminus and a decanoyl acyl chain at the N-terminus. The configuration of the amino acids was determined by Marfey’s analysis. Tolypocaibols A (1) and B (2) showed moderate, selective inhibition against Gram-positive and acid-fast bacterial strains, while maximiscin [(P/M)-3)] showed moderate, broad-spectrum antibiotic activity.
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content type line 23
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.3c00233