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Wahl, M, Jensen PR, Fenical W.  1994.  Chemical Control of Bacterial Epibiosis on Ascidians. Marine Ecology-Progress Series. 110:45-57.   10.3354/meps110045   AbstractWebsite

Two co-occurring ascidians of the Pacific subtidal, Polyclinum planum and Cystodytes lobatus, were found to exhibit remarkably different numbers of surface bacteria. On average, epibacterial densities on P. planum were 140 times greater than those on C lobatus as measured by plate-counting methods. Organic extracts of both ascidian species were tested for antimicrobial activities and effects on bacterial settlement. Bacterial settlement was measured using a new bioassay described in this paper. The results of the settlement bioassay clearly demonstrate that extracts of the little-colonized C. lobatus deter bacterial settlement while extracts of the heavily colonized P. planum induce settlement relative to the control. In addition to reducing bacterial settlement, extracts of C. lobatus colonies exhibited varying, but generally low, levels of antiraicrobial activity against, on average, one-half of the 36 strains of marine bacteria tested. On an interspecific level, including 11 ascidian species screened in a pilot study, fouling-deterring activities were correlated with epibacterial abundances while antimicrobial activity was not. It is concluded that the chemical control of bacterial settlement, possibly complemented by antimicrobial toxicity, provides an accurate model to explain the dramatically different bacterial abundance on the surfaces of the ascidian species studied. This investigation presents evidence that non-toxic metabolites influence bacterial settlement and, in this way, may function to regulate bacterial epibiosis on the surfaces of some marine invertebrates.

Wang, MX, Carver JJ, Phelan VV, Sanchez LM, Garg N, Peng Y, Nguyen DD, Watrous J, Kapono CA, Luzzatto-Knaan T et al..  2016.  Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking. Nature Biotechnology. 34:828-837.   10.1038/nbt.3597   AbstractWebsite

The potential of the diverse chemistries present in natural products (NP) for biotechnology and medicine remains untapped because NP databases are not searchable with raw data and the NP community has no way to share data other than in published papers. Although mass spectrometry (MS) techniques are well-suited to high-throughput characterization of NP, there is a pressing need for an infrastructure to enable sharing and curation of data. We present Global Natural Products Social Molecular Networking (GNPS; http://gnps.ucsd.edu), an open-access knowledge base for community-wide organization and sharing of raw, processed or identified tandem mass (MS/MS) spectrometry data. In GNPS, crowdsourced curation of freely available community-wide reference MS libraries will underpin improved annotations. Data-driven social-networking should facilitate identification of spectra and foster collaborations. We also introduce the concept of 'living data' through continuous reanalysis of deposited data.

Wietz, M, Duncan K, Patin NV, Jensen PR.  2013.  Antagonistic interactions mediated by marine bacteria: The role of small molecules. Journal of Chemical Ecology. 39:879-891.   10.1007/s10886-013-0316-x   AbstractWebsite

Marine bacteria are known to produce a wide variety of structurally diverse and biologically active secondary metabolites. Considerably less is known about the ecological functions of these compounds, in part due to methodological challenges associated with this field of research. Here, we review the antagonistic activities mediated by marine bacteria with a focus on activities linked to structurally defined secondary metabolites. Bacterial antagonism has been documented against other marine bacteria as well as eukaryotes, and includes antibiosis, the inhibition of quorum sensing, larval settlement deterrence, and defense against predation. These compounds likely play important ecological roles that ultimately affect ecosystem structure and function, however, much remains to be learned before these roles can be fully appreciated. Recent technological advances coupled with a better understanding of the diverse processes mediated by secondary metabolites provide new opportunities to expand our understanding of the chemical ecology of bacterial antagonism in the marine environment.

Wietz, M, Millan-Aguinaga N, Jensen PR.  2014.  CRISPR-Cas systems in the marine actinomycete Salinispora: linkages with phage defense, microdiversity and biogeography. Bmc Genomics. 15   10.1186/1471-2164-15-936   AbstractWebsite

Background: Prokaryotic CRISPR-Cas systems confer resistance to viral infection and thus mediate bacteria-phage interactions. However, the distribution and functional diversity of CRISPRs among environmental bacteria remains largely unknown. Here, comparative genomics of 75 Salinispora strains provided insight into the diversity and distribution of CRISPR-Cas systems in a cosmopolitan marine actinomycete genus. Results: CRISPRs were found in all Salinispora strains, with the majority containing multiple loci and different Cas array subtypes. Of the six subtypes identified, three have not been previously described. A lower prophage frequency in S. arenicola was associated with a higher fraction of spacers matching Salinispora prophages compared to S. tropica, suggesting differing defensive capacities between Salinispora species. The occurrence of related prophages in strains from distant locations, as well as spacers matching those prophages inserted throughout spacer arrays, indicate recurring encounters with widely distributed phages over time. Linkages of CRISPR features with Salinispora microdiversity pointed to subclade-specific contacts with mobile genetic elements (MGEs). This included lineage-specific spacer deletions or insertions, which may reflect weak selective pressures to maintain immunity or distinct temporal interactions with MGEs, respectively. Biogeographic patterns in spacer and prophage distributions support the concept that Salinispora spp. encounter localized MGEs. Moreover, the presence of spacers matching housekeeping genes suggests that CRISPRs may have functions outside of viral defense. Conclusions: This study provides a comprehensive examination of CRISPR-Cas systems in a broadly distributed group of environmental bacteria. The ubiquity and diversity of CRISPRs in Salinispora suggests that CRISPR-mediated interactions with MGEs represent a major force in the ecology and evolution of this cosmopolitan marine actinomycete genus.

Williams, PG, Miller ED, Asolkar RN, Jensen PR, Fenical W.  2007.  Arenicolides A-C, 26-membered ring macrolides from the marine actinomycete Salinispora arenicola. Journal of Organic Chemistry. 72:5025-5034.   10.1021/jo061878x   AbstractWebsite

Chemical evaluation of the saline fermentation broth of several strains of the obligate marine actinomycete Salinispora arenicola has led to the identification of three new macrolide polyketides designated arenicolides A-C (1-3). The planar structures, elucidated via spectroscopic and chemical methods, consist of 26-membered polyunsaturated macrolactones containing repeating vicinal hydroxyl methoxyl moieties. The relative and absolute stereochemistries of 1-3 were assigned by a combination of J-based configurational analyses and chemical derivatization.

Williams, PG, Buchanan GO, Feling RH, Kauffman CA, Jensen PR, Fenical W.  2005.  New cytotoxic salinosporamides from the marine actinomycete Salinispora tropica. Journal of Organic Chemistry. 70:6196-6203.   10.1021/jo050511   AbstractWebsite

An extensive study of the secondary metabolites produced by the obligate marine actinomycete Salinispora tropica (strain CNB-392), the producing microbe of the potent proteasome inhibitor salinosporamide A (1), has led to the isolation of seven related gamma-lactams. The most important of these compounds were salinosporamide B (3), which is the deschloro-analogue of 1, and salinosporamide C (4), which is a decarboxylated pyrrole analogue. New SAR data for all eight compounds, derived from extensive testing against the human colon carcinoma HCT-116 and the 60-cell-line panel at the NCI, indicate that the chloroethyl moiety plays a major role in the enhanced activity of 1.

Williams, PG, Asolkar RN, Kondratyuk T, Pezzuto JM, Jensen PR, Fenical W.  2007.  Saliniketals A and B, bicyclic polyketides from the marine actinomycete Salinispora arenicola. Journal of Natural Products. 70:83-88.   10.1021/np0604580   AbstractWebsite

An extensive study of the secondary metabolites produced by several strains of the marine actinomycete Salinispora arenicola has led to the isolation of two unusual bicyclic polyketides, saliniketals A and B (1, 2). The structures, which contain a new 1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-3-yl ring, were assigned mainly by 2D NMR spectroscopic methods. Unexpectedly, chemical derivatization of saliniketal A with Mosher's acid chloride resulted in a functional group interconversion of an unsaturated primary amide to the corresponding nitrile in a quantitative yield under unusually mild conditions. Saliniketals A and B were found to inhibit ornithine decarboxylase induction, an important target for the chemoprevention of cancer, with IC50 values of 1.95 +/- 0.37 and 7.83 +/- 1.2 mu g/mL, respectively.

Wilson, MC, Nam SJ, Gulder TAM, Kauffman CA, Jensen PR, Fenical W, Moore BS.  2011.  Structure and Biosynthesis of the Marine Streptomycete Ansamycin Ansalactam A and Its Distinctive Branched Chain Polyketide Extender Unit. Journal of the American Chemical Society. 133:1971-1977.   10.1021/ja109226s   AbstractWebsite

Reported is the structure and biosynthesis of ansalactam A, an ansamycin class polyketide produced by an unusual modification of the polyketide pathway. This new metabolite, produced by a marine sediment-derived bacterium of the genus Streptomyces, possesses a novel spiro gamma-lactam moiety and a distinctive isobutyryl polyketide fragment observed for the first time in this class of natural products. The structure of ansalactam A was defined by spectroscopic methods including X-ray crystallographic analysis. Biosynthetic studies with stable isotopes further led to the discovery of a new, branched chain polyketide synthase extender unit derived from (E)-4-methyl-2-pentenoic acid for polyketide assembly observed for the first time in this class of natural products.