Application of Carbon-13 in Biosynthetic Studies; Ft-13c Nuclear Magnetic Resonance Spectra of Dihydrolatumcidin

Seto, Haruo; Sato, Tsutomu; Yonehara, Hiroshi; Jankowski, William C.

doi:10.7164/antibiotics.26.609

Cited by 12 publications

(13 citation statements)

References 4 publications

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“…11d), 94 latumcidin (AKA: abikoviromycin) is an antiviral compound (Fig. 11e), 103–105 pyrindicin is a weak antimicrobial with analgesic and antiplatelet properties, 97 streptazones have exhibited antibiotic and cytotoxic activity, 98, 99 and the complex set of argimycins PI—IX are weakly antibiotic. 106,107…”

Section: Amine-containing Natural Productsmentioning

confidence: 99%

Natural products from thioester reductase containing biosynthetic pathways

et al. 2018

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Thioester reductase domains catalyze two- and four-electron reductions to release natural products following assembly on nonribosomal peptide synthetases, polyketide synthases, and their hybrid biosynthetic complexes. This reductive off-loading of a natural product yields an aldehyde or alcohol, can initiate the formation of a macrocyclic imine, and contributes to important intermediates in a variety of biosyntheses, including those for polyketide alkaloids and pyrrolobenzodiazepines. Compounds that arise from reductase-terminated biosynthetic gene clusters are often reactive and exhibit biological activity. Biomedically important examples include the cancer therapeutic Yondelis (ecteinascidin 743), peptide aldehydes that inspired the first therapeutic proteasome inhibitor bortezomib, and numerous synthetic derivatives and antibody drug conjugates of the pyrrolobenzodiazepines. Recent advances in microbial genomics, metabolomics, bioinformatics, and reactivity-based labeling have facilitated the detection of these compounds for targeted isolation. Herein, we summarize known natural products arising from this important category, highlighting their occurrence in Nature, biosyntheses, biological activities, and the technologies used for their detection and identification. Additionally, we review publicly available genomic data to highlight the remaining potential for novel reductively tailored compounds and drug leads from microorganisms. This thorough retrospecive highlights various molecularfamilies with especially privileged bioactivity while illuminating challenges and prospects toward accelerating the discovery of new, high value natural products.

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Section: Amine-containing Natural Productsmentioning

confidence: 99%

Natural products from thioester reductase containing biosynthetic pathways

et al. 2018

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“…For example, labeling with [2-13C]acetate and observation of one-bond 13C-13C coupling5 indicated a rearrangement step during formation of sterigmatocystin (6) and cyclization of a polyketide chain to yield an odd-numbered carbocyclic ring during the biosynthesis of latumcidin 28 (isolated as the dihydro derivative 7). In avenaciolide (8), coupling resulted from participation of acetate in the tricarboxylic acid Stereospecific Information.…”

Section: Single 13c-labelingmentioning

confidence: 99%

Use of carbon-13 magnetic resonance spectroscopy for biosynthetic investigations

McInnes¹,

Wright²

1975

Acc. Chem. Res.

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“…Most of these compounds are peptides (ribosomal and non-ribosomal synthesized), polyketides or terpenes. Particularly, several piperidine-containing alkaloids of polyketide origin have been isolated from actinomycetes, such as coelimycin P ( Gómez-Escribano et al, 2012 ), cyclizidine ( Freer et al, 1982 ), iromycins ( Surup et al, 2007 ), latumcidin (also known as abikoviromycin; Seto et al, 1973 ), piericidins ( Zhou and Fenical, 2016 ), strepchazolins ( Yang et al, 2017 ), streptazolins ( Mayer and Thiericke, 1993 ; Puder et al, 2001 ), streptazones A–D ( Puder et al, 2000 ), streptazone E ( Liu et al, 2013 ), or streptopyridines ( Groenhagen et al, 2014 ). These compounds show a range of activities such as antimicrobial, antiviral, cytotoxic, decreasing blood pressure and cholesterol biosynthesis, or analgesic ( Umezawa et al, 1951 ; Terashima et al, 1970 ; Grabley et al, 1991 ; Puder et al, 2001 ).…”

Section: Introductionmentioning

confidence: 99%

New Insights into the Biosynthesis Pathway of Polyketide Alkaloid Argimycins P in Streptomyces argillaceus

Braña

González‐Sabín

et al. 2018

Front. Microbiol.

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Argimycins P are a recently identified family of polyketide alkaloids encoded by the cryptic gene cluster arp of Streptomyces argillaceus. These compounds contain either a piperideine ring, or a piperidine ring which may be fused to a five membered ring, and a polyene side chain, which is bound in some cases to an N-acetylcysteine moiety. The arp cluster consists of 11 genes coding for structural proteins, two for regulatory proteins and one for a hypothetical protein. Herein, we have characterized the post-piperideine ring biosynthesis steps of argimycins P through the generation of mutants in arp genes, the identification and characterization of compounds accumulated by those mutants, and cross-feeding experiments between mutants. Based in these results, a biosynthesis pathway is proposed assigning roles to every arp gene product. The regulation of the arp cluster is also addressed by inactivating/overexpressing the positive SARP-like arpRI and the negative TetR-like arpRII transcriptional regulators and determining the effect on argimycins P production, and through gene expression analyses (reverse transcription PCR and quantitative real-time PCR) of arp genes in regulatory mutants in comparison to the wild type strain. These findings will contribute to deepen the knowledge on the biosynthesis of piperidine-containing polyketides and provide tools that can be used to generate new analogs by genetic engineering and/or biocatalysis.

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Application of Carbon-13 in Biosynthetic Studies; Ft-13c Nuclear Magnetic Resonance Spectra of Dihydrolatumcidin

Cited by 12 publications

References 4 publications

Natural products from thioester reductase containing biosynthetic pathways

Natural products from thioester reductase containing biosynthetic pathways

Use of carbon-13 magnetic resonance spectroscopy for biosynthetic investigations

New Insights into the Biosynthesis Pathway of Polyketide Alkaloid Argimycins P in Streptomyces argillaceus

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