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

Huijuan Guo; Nina B. Kreuzenbeck; Saria Otani; Maria Garcia-Altares; Hans-Martin Dahse; Christiane Weigel; Duur K. Aanen; Christian Hertweck; Michael Thomas-Poulsen; Christine Beemelmanns

doi:10.1021/acs.orglett.6b01437

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

Huijuan Guo, Nina B. Kreuzenbeck, Saria Otani, Maria Garcia-Altares, Hans-Martin Dahse, Christiane Weigel, Duur K. Aanen, Christian Hertweck, Michael Thomas-Poulsen, Christine Beemelmanns

Ecology and Evolution

32 Citations (Scopus)

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.

Original language	English
Journal	Organic Letters
Volume	18
Issue number	14
Pages (from-to)	3338-3341
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/acs.orglett.6b01437
Publication status	Published - 15 Jul 2016

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Guo, H., Kreuzenbeck, N. B., Otani, S., Garcia-Altares, M., Dahse, H.-M., Weigel, C., Aanen, D. K., Hertweck, C., Thomas-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. Organic Letters, 18(14), 3338-3341. https://doi.org/10.1021/acs.orglett.6b01437

Guo, H, Kreuzenbeck, NB, Otani, S, Garcia-Altares, M, Dahse, H-M, Weigel, C, Aanen, DK, Hertweck, C, Thomas-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', Organic Letters, vol. 18, no. 14, pp. 3338-3341. https://doi.org/10.1021/acs.orglett.6b01437

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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",

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T2 - a competitor of fungus-growing termite cultivars

AU - Guo, Huijuan

AU - Kreuzenbeck, Nina B.

AU - Otani, Saria

AU - Garcia-Altares, Maria

AU - Dahse, Hans-Martin

AU - Weigel, Christiane

AU - Aanen, Duur K.

AU - Hertweck, Christian

AU - Thomas-Poulsen, Michael

AU - Beemelmanns, Christine

PY - 2016/7/15

Y1 - 2016/7/15

N2 - 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.

AB - 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.

KW - Journal Article

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DO - 10.1021/acs.orglett.6b01437

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JF - Organic Letters

IS - 14

ER -

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

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