Pseudoxylallemycins A-F, cyclic tetrapeptides with rare allenyl modifications isolated from Pseudoxylaria sp. X802: A competitor of fungus-growing termite cultivars.

Guo H, Kreuzenbeck NB, Otani S, Garcia-Altares M, Dahse HM, Weigel C, Aanen DK, Hertweck C, Poulsen M, Beemelmanns C (2016) Pseudoxylallemycins A-F, cyclic tetrapeptides with rare allenyl modifications isolated from Pseudoxylaria sp. X802: A competitor of fungus-growing termite cultivars. Org Lett 18, 3338-3341. PubMed

Abstract

Based on fungus-fungus pairing assays and HRMS-based dereplication strategy, six new cyclic tetrapeptides, pseudoxylallemycins A-F (1-6), were isolated from the termite-associated fungus Pseudoxylaria sp. X802. Structures were characterized using NMR spectroscopy, HRMS, and Marfey's reaction. Pseudoxylallemycins B-D (2-4) possess a rare and chemically accessible allene moiety amenable for synthetic modifications, and derivatives A-D showed antimicrobial activity against Gram-negative human-pathogenic Pseudomonas aeruginosa and antiproliferative activity against human umbilical vein endothelial cells and K-562 cell lines.

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doi: 10.1021/acs.orglett.6b01437 PMID: 27341414