Arenicolides A−C, 26-Membered Ring Macrolides from the Marine Actinomycete <i>Salinispora arenicola</i>

Williams, Philip G.; Miller, Eric D.; Asolkar, Ratnakar N.; Jensen, Paul R.; Fenical, William

doi:10.1021/jo061878x

Cited by 88 publications

(25 citation statements)

References 47 publications

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“…The large number of nodes that networked with many of the standards suggests the presence of additional analogues in these compound classes. Examples include the cyclomarin (Renner, et al, 1999) and arenicolide (Williams, et al, 2007) molecular families, where networking reveals the production of both known compounds and what appear to be new analogs. For example, in addition to cyclomarin A and D, inspection of the parent mass and the MS/MS data suggests the molecular family contains putative demethylated, methylated, and hydrated cyclomarin A analogues ( m/z : 1051.59, 1079.62 and 1083.61, respectively).…”

Section: Resultsmentioning

confidence: 99%

“…It was possible to link an ion that matched the previously described metabolite arenicolide A (Williams, et al, 2007) to an uncharacterized biosynthetic gene cluster (PKS28) based on a number of lines of evidence. First, pattern-based analysis revealed that the two strains producing the arenicolide A ion (827.492 m/z [M+Na]) were the only strains in which PKS28 was observed ( S. arenicola strain CNQ-748 and S. pacifica strain CNT-138) (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

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Molecular Networking and Pattern-Based Genome Mining Improves Discovery of Biosynthetic Gene Clusters and their Products from Salinispora Species

Duncan

Crüsemann

Lechner

et al. 2015

Chemistry & Biology

156

145

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Summary Genome sequencing has revealed that bacteria contain many more biosynthetic gene clusters than predicted based on the number of secondary metabolites discovered to date. While this biosynthetic reservoir has fostered interest in new tools for natural product discovery, there remains a gap between gene cluster detection and compound discovery. Here we apply molecular networking and the new concept of pattern-based genome mining to 35 Salinispora strains including 30 for which draft genome sequences were either available or obtained for this study. The results provide a method to simultaneously compare large numbers of complex microbial extracts, which facilitated the identification of media components, known compounds and their derivatives, and new compounds that could be prioritized for structure elucidation. These efforts revealed considerable metabolite diversity and led to several molecular family-gene cluster pairings, of which the quinomycin-type depsipeptide retimycin A was characterized and linked to gene cluster NRPS40 using pattern-based bioinformatic approaches.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Molecular Networking and Pattern-Based Genome Mining Improves Discovery of Biosynthetic Gene Clusters and their Products from Salinispora Species

Duncan

Crüsemann

Lechner

et al. 2015

Chemistry & Biology

156

145

View full text Add to dashboard Cite

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“…17 Recently, Fenical's group reported several unique bioactive metabolites from marine actinomycetes. 18 They claimed that marine actinomycetes are attractive sources for screening of new bioactive compounds. In this context, it is interesting to note that actinofuranone A was also isolated from terrestrial Actinomycetes.…”

Section: Resultsmentioning

confidence: 99%

Terpenoids Produced by Actinomycetes: Napyradiomycins from Streptomyces antimycoticus NT17

et al. 2008

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Napyradiomycin SR ( 1), 16-dechloro-16-hydroxynapyradiomycin C2 ( 2), 18-hydroxynapyradiomycin A1 ( 3), 18-oxonapyradiomycin A1 ( 4), 16-oxonapyradiomycin A2 ( 5), 7-demethyl SF2415A3 ( 6), 7-demethyl A80915B ( 7), and ( R)-3-chloro-6-hydroxy-8-methoxy-alpha-lapachone ( 8) were isolated from the culture broth of Streptomyces antimycoticus NT17. These compounds are derivatives of the napyradiomycins isolated previously from Chainia rubra or Streptomyces aculeolatus. The structures of the new compounds, some of which exhibit antibacterial activities, were established by comparing their NMR data with data of related known compounds. The unique structure of 1, containing a highly strained ring, was established by NMR and was confirmed by X-ray analysis. Two of the compounds are C-16 stereoisomers of napyradiomycin A2 and are named napyradiomycins A2a ( 9a) and A2b ( 9b).

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“…It has also been the source of a number of interesting new compounds in addition to some well-known actinomycete secondary metabolites. The first new structures reported from this species were the 26-membered ring macrolides arenicolides A–C ( 30 - 32 ) isolated from strain CNS-005 96 . These compounds were discovered using LC-MS based screening with A and B being simple methyl derivatives and C possessing a substituted tetrahydrofuran ring potentially generated from a cyclization of the epoxide.…”

Section: Salinispora Natural Productsmentioning

confidence: 98%

The marine actinomycete genus Salinispora: a model organism for secondary metabolite discovery

2015

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This review covers the initial discovery of the marine actinomycete genus Salinispora through its development as a model for natural product research. A focus is placed on the novel chemical structures reported with reference to their biological activities and the synthetic and biosynthetic studies they have inspired. The time line of discoveries progresses from more traditional bioassay-guided approaches through the application of genome mining and genetic engineering techniques that target the products of specific biosynthetic gene clusters. This overview exemplifies the extraordinary biosynthetic diversity that can emanate from a narrowly defined genus and supports future efforts to explore marine taxa in the search for novel natural products.

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Arenicolides A−C, 26-Membered Ring Macrolides from the Marine Actinomycete Salinispora arenicola

Cited by 88 publications

References 47 publications

Molecular Networking and Pattern-Based Genome Mining Improves Discovery of Biosynthetic Gene Clusters and their Products from Salinispora Species

Molecular Networking and Pattern-Based Genome Mining Improves Discovery of Biosynthetic Gene Clusters and their Products from Salinispora Species

Terpenoids Produced by Actinomycetes: Napyradiomycins from Streptomyces antimycoticus NT17

The marine actinomycete genus Salinispora: a model organism for secondary metabolite discovery

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