Elimination of Butylcycloheptylprodigiosin as a Known Natural Product Inspired by an Evolutionary Hypothesis for Cyclic Prodigiosin Biosynthesis

The cyclic prodigiosins are an important family of bioactive natural products that continue to be the subject of numerous structural, synthetic, and biosynthetic studies. In particular, the structural assignments of the isomeric cyclic prodigiosins butylcycloheptylprodigiosin (BCHP) and streptorubin...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) Jg. 76; H. 10; S. 1937 - 1945
Hauptverfasser: Jones, Brian T., Hu, Dennis X., Savoie, Brett M., Thomson, Regan J.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WASHINGTON Amer Chemical Soc 25.10.2013
Schlagworte:
Biological Products - chemistry
Biological Products - metabolism
Chemistry, Medicinal
Crystallography, X-Ray
Life Sciences & Biomedicine
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacology & Pharmacy
Plant Sciences
Prodigiosin - analogs & derivatives
Prodigiosin - biosynthesis
Prodigiosin - chemistry
Science & Technology
DNA CLEAVAGE
STREPTOMYCES-COELICOLOR A3
UNDECYLPRODIGININE
ANTICANCER
ROSEOPHILIN
METACYCLOPRODIGIOSIN
CHEMISTRY
ANTIMALARIAL ACTIVITY
PIGMENT
ALKALOIDS
ISSN:0163-3864, 1520-6025, 1520-6025
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Zusammenfassung:The cyclic prodigiosins are an important family of bioactive natural products that continue to be the subject of numerous structural, synthetic, and biosynthetic studies. In particular, the structural assignments of the isomeric cyclic prodigiosins butylcycloheptylprodigiosin (BCHP) and streptorubin B have been the cause of significant confusion. Herein, we report detailed studies regarding the electron impact (El) mass spectra of synthetic BCHP and streptorubin B that have allowed us to distinguish the two compounds in the absence of quality historical isolation NMR data. On the basis of these fragmentation differences, the status of BCHP as a natural product is challenged. The proposed mechanism of fragmentation is supported by the El mass spectra of synthetic pentyl-chain analogues of BCHP and streptorubin B, X-ray crystallography, and DFT calculations. Elimination of BCHP from the prodigiosin family supports a proposed evolutionary hypothesis for the surprising biosynthesis of cyclic prodigiosins.
Bibliographie:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0163-3864
1520-6025
1520-6025
DOI:10.1021/np400531b