Hybrid isoprenoid secondary metabolite production in terrestrial and marine actinomycetes

Gallagher, Kelley A.; Fenical, William; Jensen, Paul R.

doi:10.1016/j.copbio.2010.09.010

Cited by 55 publications

(59 citation statements)

References 54 publications

(61 reference statements)

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“…The MAR4 lineage of streptomycetes has been reported to be largely of marine origin and recognized as a source of the rare HI class of bacterial secondary metabolites (13,39). The aim of the present study was to further explore the diversity and distribution of this lineage through the application of culture-dependent and culture-independent methods and through the mining of publically available sequence data.…”

Section: Discussionmentioning

confidence: 99%

“…Phylogenetic analyses included previously identified MAR4 16S rRNA gene sequences (13), as well as strains cultured as part of the present study and strains cultured as part of prior studies (9,12,19) that were subsequently considered MAR4 candidates on the basis of sequence data or the production of HI secondary metabolites. Diverse MAR4 sequence representatives (accession numbers KC261629, KC261602, EF121313, KC261627, KC261626, X87316, NR041166, EF538742, KC261604, JF346436, EF581384, KC261611, and KC261615) were additionally used as BLASTn queries of the NCBI database.…”

Section: Methodsmentioning

confidence: 99%

“…A phenotypic trait previously associated with the MAR4 clade is the production of HI secondary metabolites (13). To further explore the relationships between HI production and MAR4 phylogeny, we analyzed the culture extracts of 21 diverse MAR4 strains over a 9-day cultivation period.…”

Section: Mar4 Diversitymentioning

confidence: 99%

“…Prior to the present study, the S. aculeolatus and S. synnematoformans type strains were the only nonmarine strains recognized within this clade (13). These strains were derived from a terrestrial soil sample and a sand dune sample, respectively, and are the only formally described species within the clade.…”

mentioning

confidence: 99%

“…The MAR4 lineage has been linked to the production of hybrid isoprenoid (HI) secondary metabolites (13), which are of mixed biosynthetic origin and include an isoprene-derived moiety. The attachment of isoprene, the building block of terpenes, to a secondary metabolite can occur on a variety of biosynthetically distinct chemical scaffolds, including phenazines, polyketides, peptides, aminocoumarins, phenylpropanoids, and alkaloids (14).…”

mentioning

confidence: 99%

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Phylogenetic and Chemical Diversity of a Hybrid-Isoprenoid-Producing Streptomycete Lineage

Gallagher

Rauscher

Ioca

et al. 2013

Appl Environ Microbiol

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Streptomyces species dedicate a large portion of their genomes to secondary metabolite biosynthesis. A diverse and largely marine-derived lineage within this genus has been designated MAR4 and identified as a prolific source of hybrid isoprenoid (HI) secondary metabolites. These terpenoid-containing compounds are common in nature but rarely observed as bacterial secondary metabolites. To assess the phylogenetic diversity of the MAR4 lineage, complementary culture-based and culture-independent techniques were applied to marine sediment samples collected off the Channel Islands, CA. The results, including those from an analysis of publically available sequence data and strains isolated as part of prior studies, placed 40 new strains in the MAR4 clade, of which 32 originated from marine sources. When combined with sequences cloned from environmental DNA, 28 MAR4 operational taxonomic units (0.01% genetic distance) were identified. Of these, 82% consisted exclusively of either cloned sequences or cultured strains, supporting the complementarity of these two approaches. Chemical analyses of diverse MAR4 strains revealed the production of five different HI structure classes. All 21 MAR4 strains tested produced at least one HI class, with most strains producing from two to four classes. The two major clades within the MAR4 lineage displayed distinct patterns in the structural classes and the number and amount of HIs produced, suggesting a relationship between taxonomy and secondary metabolite production. The production of HI secondary metabolites appears to be a phenotypic trait of the MAR4 lineage, which represents an emerging model with which to study the ecology and evolution of HI biosynthesis.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Mar4 Diversitymentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Phylogenetic and Chemical Diversity of a Hybrid-Isoprenoid-Producing Streptomycete Lineage

Gallagher

Rauscher

Ioca

et al. 2013

Appl Environ Microbiol

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Cytotoxic and Antimicrobial Napyradiomycins from Two Marine‐Derived Streptomyces Strains

2013

Self Cite

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Cancer cell cytotoxicity-guided fractionation of the acetone extracts of two cultured marine-derived Streptomyces strains belonging to the MAR4 group yielded six new napyradiomycins, compounds A–F (1–6), together with three known compounds, napyradiomycins B2–B4 (7–9). Napyradiomycins 1–4 are new members of the napyradiomycin “C type“ meroterpenoids that possess a linear monoterpene moiety bridging between C-7 and C-10a. Compound 4 has an additional tetrahydropyran ring fused to the phenol moiety. Compounds 5–9 are related to the napyradiomycin “B type” meroterpenoids. The structures of all new compounds were assigned by interpretation of 1D and 2D NMR, MS and other spectroscopic data. The relative configurations were assigned based upon interpretation of ROESY 2D NMR experiments. The cytotoxicity of 1–9 against the human colon carcinoma cell line HCT-116, and their antibacterial activities against Methicillin-resistant Staphylococcus aureus (MRSA) are presented.

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Secondary Metabolites of Endophytic Actinomycetes: Isolation, Synthesis, Biosynthesis, and Biological Activities

Bernardi

Chagas

Monteiro

et al. 2019

Progress in the Chemistry of Organic Natural Products 108

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Hybrid isoprenoid secondary metabolite production in terrestrial and marine actinomycetes

Cited by 55 publications

References 54 publications

Phylogenetic and Chemical Diversity of a Hybrid-Isoprenoid-Producing Streptomycete Lineage

Phylogenetic and Chemical Diversity of a Hybrid-Isoprenoid-Producing Streptomycete Lineage

Cytotoxic and Antimicrobial Napyradiomycins from Two Marine‐Derived Streptomyces Strains

Secondary Metabolites of Endophytic Actinomycetes: Isolation, Synthesis, Biosynthesis, and Biological Activities

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