Electrospray ionization mass spectra of piperazimycins A and B and γ-butyrolactones from a marine-derived Streptomyces sp

Khaled A. Shaaban; Mohamed Shaaban; Petrea Facey; Serge Fotso; Holm Frauendorf; Elisabeth Helmke; Armin Maier; Heinz H. Fiebig; Hartmut Laatsch

doi:10.1038/ja.2008.87

Electrospray ionization mass spectra of piperazimycins A and B and γ-butyrolactones from a marine-derived Streptomyces sp

Khaled A. Shaaban, Mohamed Shaaban, Petrea Facey, Serge Fotso, Holm Frauendorf, Elisabeth Helmke, Armin Maier, Heinz H. Fiebig, Hartmut Laatsch

Pharmaceutical Sciences

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

11 Scopus citations

Abstract

Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (la, lb). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4- olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three y-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed ID and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.

Original language	English
Pages (from-to)	736-746
Number of pages	11
Journal	Journal of Antibiotics
Volume	61
Issue number	12
DOIs	https://doi.org/10.1038/ja.2008.87
State	Published - Dec 2008

Bibliographical note

Funding Information:
Acknowledgements We thank Mr. R. Machinek for NMR measurements, F. Lissy for biological activity tests and A. Kohl for technical assistance. P. Facey thanks the Alexander von Humboldt Foundation (AvH) for a research fellowship. Financial support from the BMBF (Project No. 03F0415A) is gratefully acknowledged.

Keywords

Marine-derived streptomyces sp
Piperazimycins
γ-butyrolactones

ASJC Scopus subject areas

Pharmacology
Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1038/ja.2008.87

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title = "Electrospray ionization mass spectra of piperazimycins A and B and γ-butyrolactones from a marine-derived Streptomyces sp",

abstract = "Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (la, lb). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4- olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three y-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed ID and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.",

keywords = "Marine-derived streptomyces sp, Piperazimycins, γ-butyrolactones",

author = "Shaaban, {Khaled A.} and Mohamed Shaaban and Petrea Facey and Serge Fotso and Holm Frauendorf and Elisabeth Helmke and Armin Maier and Fiebig, {Heinz H.} and Hartmut Laatsch",

note = "Funding Information: Acknowledgements We thank Mr. R. Machinek for NMR measurements, F. Lissy for biological activity tests and A. Kohl for technical assistance. P. Facey thanks the Alexander von Humboldt Foundation (AvH) for a research fellowship. Financial support from the BMBF (Project No. 03F0415A) is gratefully acknowledged.",

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doi = "10.1038/ja.2008.87",

language = "English",

volume = "61",

pages = "736--746",

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AU - Shaaban, Khaled A.

AU - Shaaban, Mohamed

AU - Facey, Petrea

AU - Fotso, Serge

AU - Frauendorf, Holm

AU - Helmke, Elisabeth

AU - Maier, Armin

AU - Fiebig, Heinz H.

AU - Laatsch, Hartmut

N1 - Funding Information: Acknowledgements We thank Mr. R. Machinek for NMR measurements, F. Lissy for biological activity tests and A. Kohl for technical assistance. P. Facey thanks the Alexander von Humboldt Foundation (AvH) for a research fellowship. Financial support from the BMBF (Project No. 03F0415A) is gratefully acknowledged.

PY - 2008/12

Y1 - 2008/12

N2 - Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (la, lb). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4- olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three y-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed ID and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.

AB - Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (la, lb). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4- olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three y-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed ID and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.

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KW - Piperazimycins

KW - γ-butyrolactones

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Electrospray ionization mass spectra of piperazimycins A and B and γ-butyrolactones from a marine-derived Streptomyces sp

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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