Karamomycins A-C: 2-Naphthalen-2-yl-thiazoles from Nonomuraea endophytica

Khaled A. Shaaban; Mohamed Shaaban; Hafizur Rahman; Iris Grün-Wollny; Peter Kämpfer; Gerhard Kelter; Heinz Herbert Fiebig; Hartmut Laatsch

doi:10.1021/acs.jnatprod.8b00928

Karamomycins A-C: 2-Naphthalen-2-yl-thiazoles from Nonomuraea endophytica

Khaled A. Shaaban, Mohamed Shaaban, Hafizur Rahman, Iris Grün-Wollny, Peter Kämpfer, Gerhard Kelter, Heinz Herbert Fiebig, Hartmut Laatsch

Pharmaceutical Sciences

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

16 Scopus citations

Abstract

Karamomycins A-C (2-4), the first natural 2-naphthalen-2-yl-thiazole derivatives, were isolated along with a plausible precursor molecule, 1-hydroxy-4-methoxy-2-naphthoic acid (1), uracil, 1-acetyl-β-carboline, and actinomycin C2 from the culture broth of the terrestrial actinomycete strain GW58/450, identified as Nonomuraea endophytica. These compounds were characterized by analysis of their NMR and mass spectrometry (MS) data; the absolute configurations of 2 and 4 were determined by comparison of ¹³C NMR, NOESY, and circular dichroism (CD) spectra with density functional theory (DFT)-calculated data. In karamomycin C (4), the thiazole of 2 is connected to an unusual iminothiazolo[4,3-c][1,4]thiazepinone, for which we proposed a biosynthetic origin from two cysteine residues. It is closely related to ulbactin F; however, the heterocycle is enantiomeric to the latter and connected to phenol instead of 4-methoxy-1-naphthol. Karamomycins A (2) and C (4) were cytotoxic.

Original language	English
Pages (from-to)	870-877
Number of pages	8
Journal	Journal of Natural Products
Volume	82
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.8b00928
State	Published - Apr 26 2019

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society and American Society of Pharmacognosy.

Funding

We thank R. Machinek for the NMR spectra, Dr. H. Frauendorf for the mass spectra, Dr. J. Junker for his help in using COCON, Dr. S. Hickford and Dr. C. Pearce for language polishing, and F. Lissy and A. Kohl for technical assistance. The financial support of this work by a grant from the Bundesministerium für Bildung und Forschung (Grant No. 03F04153A) is gratefully acknowledged.

Funders	Funder number
Bundesministerium für Bildung und Forschung	03F04153A
Bundesministerium für Bildung und Forschung

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.8b00928

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title = "Karamomycins A-C: 2-Naphthalen-2-yl-thiazoles from Nonomuraea endophytica",

abstract = "Karamomycins A-C (2-4), the first natural 2-naphthalen-2-yl-thiazole derivatives, were isolated along with a plausible precursor molecule, 1-hydroxy-4-methoxy-2-naphthoic acid (1), uracil, 1-acetyl-β-carboline, and actinomycin C2 from the culture broth of the terrestrial actinomycete strain GW58/450, identified as Nonomuraea endophytica. These compounds were characterized by analysis of their NMR and mass spectrometry (MS) data; the absolute configurations of 2 and 4 were determined by comparison of 13C NMR, NOESY, and circular dichroism (CD) spectra with density functional theory (DFT)-calculated data. In karamomycin C (4), the thiazole of 2 is connected to an unusual iminothiazolo[4,3-c][1,4]thiazepinone, for which we proposed a biosynthetic origin from two cysteine residues. It is closely related to ulbactin F; however, the heterocycle is enantiomeric to the latter and connected to phenol instead of 4-methoxy-1-naphthol. Karamomycins A (2) and C (4) were cytotoxic.",

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Karamomycins A-C: 2-Naphthalen-2-yl-thiazoles from Nonomuraea endophytica

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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