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 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Organic Letters
Vol/bind	18
Udgave nummer	14
Sider (fra-til)	3338-3341
Antal sider	4
ISSN	1523-7060
DOI	https://doi.org/10.1021/acs.orglett.6b01437
Status	Udgivet - 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, bind 18, nr. 14, s. 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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author = "Huijuan Guo and Kreuzenbeck, {Nina B.} and Saria Otani and Maria Garcia-Altares and Hans-Martin Dahse and Christiane Weigel and Aanen, {Duur K.} and Christian Hertweck and Michael Thomas-Poulsen and Christine Beemelmanns",

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doi = "10.1021/acs.orglett.6b01437",

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T1 - Pseudoxylallemycins A-F, cyclic tetrapeptides with rare allenyl modifications isolated from Pseudoxylaria sp. X802

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

U2 - 10.1021/acs.orglett.6b01437

DO - 10.1021/acs.orglett.6b01437

M3 - Letter

C2 - 27341414

SN - 1523-7060

VL - 18

SP - 3338

EP - 3341

JO - Organic Letters

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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