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

Producción científica: Article › revisión exhaustiva

13 Citas (SciVal)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	736-746
Número de páginas	11
Publicación	Journal of Antibiotics
Volumen	61
N.º	12
DOI	https://doi.org/10.1038/ja.2008.87
Estado	Published - dic 2008

Nota bibliográfica

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.

Financiación

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.

Financiadores	Número del financiador
Alexander von Humboldt-Stiftung
Bundesministerium für Bildung und Forschung	03F0415A

ODS de las Naciones Unidas

Este resultado contribuye a los siguientes Objetivos de Desarrollo Sostenible

Life below water

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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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.",

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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",

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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.

KW - Marine-derived streptomyces sp

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

Resumen

Nota bibliográfica

Financiación

ODS de las Naciones Unidas

ASJC Scopus subject areas

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