Mullinamides A and B, new cyclopeptides produced by the Ruth Mullins coal mine fire isolate Streptomyces sp. RM-27-46

Xiachang Wang; Khaled A. Shaaban; Sherif I. Elshahawi; Larissa V. Ponomareva; Manjula Sunkara; Gregory C. Copley; James C. Hower; Andrew J. Morris; Madan K. Kharel; Jon S. Thorson

doi:10.1038/ja.2014.37

Mullinamides A and B, new cyclopeptides produced by the Ruth Mullins coal mine fire isolate Streptomyces sp. RM-27-46

Xiachang Wang, Khaled A. Shaaban, Sherif I. Elshahawi, Larissa V. Ponomareva, Manjula Sunkara, Gregory C. Copley, James C. Hower, Andrew J. Morris, Madan K. Kharel, Jon S. Thorson

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Two new cyclopeptides, mullinamides A [cyclo-(-L-Gly-L-Glu-L-Val-L-Ile-L- Pro-)] and B [cyclo-(-L-Glu-L-Met-L-Pro-)] were isolated from the crude extract of terrestrial Streptomyces sp. RM-27-46 along with the three known cyclopeptides surugamide A [cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D- Ala-)], cyclo-(-L-Pro-L-Phe-) and cyclo-(-L-Pro-L-Leu-). The structures of the new compounds were elucidated by the cumulative analyses of NMR spectroscopy and HRMS. Although mullinamides A and B displayed no appreciable antimicrobial/fungal activity or cytotoxicity, this study highlights the first reported antibacterial activity of surugamide A.

Original language	English
Pages (from-to)	571-575
Number of pages	5
Journal	Journal of Antibiotics
Volume	67
Issue number	8
DOIs	https://doi.org/10.1038/ja.2014.37
State	Published - Aug 2014

Bibliographical note

Funding Information:
This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117).

Funding

This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117).

Funders	Funder number
University of Kentucky
National Center for Advancing Translational Sciences (NCATS)	UL1TR000117
University of Kentucky Markey Cancer Center

Keywords

antibiotic
bioprospecting
cyclopeptide
natural product
pharmacognosy
surugamide

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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10.1038/ja.2014.37

Cite this

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title = "Mullinamides A and B, new cyclopeptides produced by the Ruth Mullins coal mine fire isolate Streptomyces sp. RM-27-46",

abstract = "Two new cyclopeptides, mullinamides A [cyclo-(-L-Gly-L-Glu-L-Val-L-Ile-L- Pro-)] and B [cyclo-(-L-Glu-L-Met-L-Pro-)] were isolated from the crude extract of terrestrial Streptomyces sp. RM-27-46 along with the three known cyclopeptides surugamide A [cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D- Ala-)], cyclo-(-L-Pro-L-Phe-) and cyclo-(-L-Pro-L-Leu-). The structures of the new compounds were elucidated by the cumulative analyses of NMR spectroscopy and HRMS. Although mullinamides A and B displayed no appreciable antimicrobial/fungal activity or cytotoxicity, this study highlights the first reported antibacterial activity of surugamide A.",

keywords = "antibiotic, bioprospecting, cyclopeptide, natural product, pharmacognosy, surugamide",

author = "Xiachang Wang and Shaaban, {Khaled A.} and Elshahawi, {Sherif I.} and Ponomareva, {Larissa V.} and Manjula Sunkara and Copley, {Gregory C.} and Hower, {James C.} and Morris, {Andrew J.} and Kharel, {Madan K.} and Thorson, {Jon S.}",

note = "Funding Information: This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117).",

year = "2014",

month = aug,

doi = "10.1038/ja.2014.37",

language = "English",

volume = "67",

pages = "571--575",

number = "8",

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AU - Wang, Xiachang

AU - Shaaban, Khaled A.

AU - Elshahawi, Sherif I.

AU - Ponomareva, Larissa V.

AU - Sunkara, Manjula

AU - Copley, Gregory C.

AU - Hower, James C.

AU - Morris, Andrew J.

AU - Kharel, Madan K.

AU - Thorson, Jon S.

N1 - Funding Information: This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117).

PY - 2014/8

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N2 - Two new cyclopeptides, mullinamides A [cyclo-(-L-Gly-L-Glu-L-Val-L-Ile-L- Pro-)] and B [cyclo-(-L-Glu-L-Met-L-Pro-)] were isolated from the crude extract of terrestrial Streptomyces sp. RM-27-46 along with the three known cyclopeptides surugamide A [cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D- Ala-)], cyclo-(-L-Pro-L-Phe-) and cyclo-(-L-Pro-L-Leu-). The structures of the new compounds were elucidated by the cumulative analyses of NMR spectroscopy and HRMS. Although mullinamides A and B displayed no appreciable antimicrobial/fungal activity or cytotoxicity, this study highlights the first reported antibacterial activity of surugamide A.

AB - Two new cyclopeptides, mullinamides A [cyclo-(-L-Gly-L-Glu-L-Val-L-Ile-L- Pro-)] and B [cyclo-(-L-Glu-L-Met-L-Pro-)] were isolated from the crude extract of terrestrial Streptomyces sp. RM-27-46 along with the three known cyclopeptides surugamide A [cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D- Ala-)], cyclo-(-L-Pro-L-Phe-) and cyclo-(-L-Pro-L-Leu-). The structures of the new compounds were elucidated by the cumulative analyses of NMR spectroscopy and HRMS. Although mullinamides A and B displayed no appreciable antimicrobial/fungal activity or cytotoxicity, this study highlights the first reported antibacterial activity of surugamide A.

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Mullinamides A and B, new cyclopeptides produced by the Ruth Mullins coal mine fire isolate Streptomyces sp. RM-27-46

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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