Frankiamide: A Structural Revision to Demethyl (C-11) Cezomycin

Klika, Karel D.; Haansuu, Johannes Pasi; Ovcharenko, Vladimir V.; Haahtela, Kielo; Vuorela, Pia; Sillanpää, Reijo; Pihlaja, Kalevi

doi:10.1515/znb-2003-1209

Cited by 12 publications

(2 citation statements)

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“…To date, the secondary metabolome of Frankia has not been explored beyond two reports concerning the production of anthraquinone- and calcimycin-type antibiotics 149,150. The genome sequences of Frankia now certainly provide a rationale to explore the chemistry of these intriguing microorganisms.…”

Section: Actinomycete Genome Projectsmentioning

confidence: 99%

Genomic basis for natural product biosynthetic diversity in the actinomycetes

2009

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The phylum Actinobacteria hosts diverse high G + C, Gram-positive bacteria that have evolved a complex chemical language of natural product chemistry to help navigate their fascinatingly varied lifestyles. To date, 71 Actinobacteria genomes have been completed and annotated, with the vast majority representing the Actinomycetales, which are the source of numerous antibiotics and other drugs from genera such as Streptomyces, Saccharopolyspora and Salinispora. These genomic analyses have illuminated the secondary metabolic proficiency of these microbes – underappreciated for years based on conventional isolation programs – and have helped set the foundation for a new natural product discovery paradigm based on genome mining. Trends in the secondary metabolomes of natural product-rich actinomycetes are highlighted in this review article, which contains 199 references.

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Section: Actinomycete Genome Projectsmentioning

confidence: 99%

Genomic basis for natural product biosynthetic diversity in the actinomycetes

2009

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“…Quinonoid pigments of presumptive polyketide origin and a derivative of the calcium-binding streptomyceteproduced calcimycin antibiotics, demethyl C-11 cezomycin, were isolated from Frankia strains ORS 020604 and AiPs1, respectively, and their structures determined as early examples of Frankia-based natural products (25,30). The most wellstudied area for Frankia has focused on the production of numerous oxidized and cyclopropanated fatty acids and triterpene hopanoids that differ in content between vegetativegrowth cells and those in N 2 -fixing vesicles (54).…”

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Significant Natural Product Biosynthetic Potential of Actinorhizal Symbionts of the Genus Frankia, as Revealed by Comparative Genomic and Proteomic Analyses

Udwary

Gontang

Jones

et al. 2011

Appl Environ Microbiol

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Bacteria of the genus Frankia are mycelium-forming actinomycetes that are found as nitrogen-fixing facultative symbionts of actinorhizal plants. Although soil-dwelling actinomycetes are well-known producers of bioactive compounds, the genus Frankia has largely gone uninvestigated for this potential. Bioinformatic analysis of the genome sequences of Frankia strains ACN14a, CcI3, and EAN1pec revealed an unexpected number of secondary metabolic biosynthesis gene clusters. Our analysis led to the identification of at least 65 biosynthetic gene clusters, the vast majority of which appear to be unique and for which products have not been observed or characterized. More than 25 secondary metabolite structures or structure fragments were predicted, and these are expected to include cyclic peptides, siderophores, pigments, signaling molecules, and specialized lipids. Outside the hopanoid gene locus, no cluster could be convincingly demonstrated to be responsible for the few secondary metabolites previously isolated from other Frankia strains. Few clusters were shared among the three species, demonstrating species-specific biosynthetic diversity. Proteomic analysis of Frankia sp. strains CcI3 and EAN1pec showed that significant and diverse secondary metabolic activity was expressed in laboratory cultures. In addition, several prominent signals in the mass range of peptide natural products were observed in Frankia sp. CcI3 by intact-cell matrix-assisted laser desorption-ionization mass spectrometry (MALDI-MS). This work supports the value of bioinformatic investigation in natural products biosynthesis using genomic information and presents a clear roadmap for natural products discovery in the Frankia genus.

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Advances in X‐Ray Diffraction

Jegorov

Hušák

2014

Natural Products Analysis

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Frankiamide: A Structural Revision to Demethyl (C-11) Cezomycin

Cited by 12 publications

References 1 publication

Genomic basis for natural product biosynthetic diversity in the actinomycetes

Genomic basis for natural product biosynthetic diversity in the actinomycetes

Significant Natural Product Biosynthetic Potential of Actinorhizal Symbionts of the Genus Frankia, as Revealed by Comparative Genomic and Proteomic Analyses

Advances in X‐Ray Diffraction

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