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Lane, AL, Nam SJ, Fukuda T, Yamanaka K, Kauffman CA, Jensen PR, Fenical W, Moore BS.  2013.  Structures and Comparative Characterization of Biosynthetic Gene Clusters for Cyanosporasides, Enediyne-Derived Natural Products from Marine Actinomycetes. Journal of the American Chemical Society. 135:4171-4174.   10.1021/ja311065v   AbstractWebsite

Cyanosporasides are marine bacterial natural products containing a chlorinated cyclopenta[a]indene core of suspected enediyne polyketide biosynthetic origin. Herein, we report the isolation and characterization of novel cyanosporasides C-F (3-6) from the marine actinomycetes Salinispora pacifica CNS-143 and Streptomyces sp. CNT-179, highlighted by the unprecedented C-2' N-acetylcysteamine functionalized hexose group of 6. Cloning, sequencing, and mutagenesis of homologous similar to 50 kb cyanosporaside biosynthetic gene clusters from both bacteria afforded the first genetic evidence supporting cyanosporaside's enediyne, and thereby p-benzyne biradical, biosynthetic origin and revealed the molecular basis for nitrile and glycosyl functionalization. This study provides new opportunities for bioengineering of enediyne derivatives and expands the structural diversity afforded by enediyne gene clusters.

Letzel, AC, Li J, Amos GCA, Millan-Aguinaga N, Ginigini J, Abdelmohsen UR, Gaudencio SP, Ziemert N, Moore BS, Jensen PR.  2017.  Genomic insights into specialized metabolism in the marine actinomycete Salinispora. Environmental Microbiology. 19:3660-3673.   10.1111/1462-2920.13867   AbstractWebsite

Comparative genomics is providing new opportunities to address the diversity and distributions of genes encoding the biosynthesis of specialized metabolites. An analysis of 119 genome sequences representing three closely related species of the marine actinomycete genus Salinispora reveals extraordinary biosynthetic diversity in the form of 176 distinct biosynthetic gene clusters (BGCs) of which only 24 have been linked to their products. Remarkably, more than half of the BGCs were observed in only one or two strains, suggesting they were acquired relatively recently in the evolutionary history of the genus. These acquired gene clusters are concentrated in specific genomic islands, which represent hot spots for BGC acquisition. While most BGCs are stable in terms of their chromosomal position, others migrated to different locations or were exchanged with unrelated gene clusters suggesting a plug and play type model of evolution that provides a mechanism to test the relative fitness effects of specialized metabolites. Transcriptome analyses were used to address the relationships between BGC abundance, chromosomal position and product discovery. The results indicate that recently acquired BGCs can be functional and that complex evolutionary processes shape the micro-diversity of specialized metabolism observed in closely related environmental bacteria.

Lindel, T, Jensen PR, Fenical W, Long BH, Casazza AM, Carboni J, Fairchild CR.  1997.  Eleutherobin, a new cytotoxin that mimics paclitaxel (Taxol) by stabilizing microtubules. Journal of the American Chemical Society. 119:8744-8745.   10.1021/ja9717828   Website
Lindel, T, Jensen PR, Fenical W.  1996.  Lagunapyrones A-C: Cytotoxic acetogenins of a new skeletal class from a marine sediment bacterium. Tetrahedron Letters. 37:1327-1330.   10.1016/0040-4039(96)00014-7   AbstractWebsite

The structures of the lagunapyrones A-C (1-3), novel, cytotoxic alpha-pyrones, produced in fermentation by a marine bacterium, have been assigned on the basis of comprehensive spectroscopic analyses. Transformation of lagunapyrone B (2) to its [1', 3'-C-13(2)]-labelled acetonide allowed the relative stereochemistry of the flexible 1,3-diol moiety to be determined.

Liu, ZM, Jensen PR, Fenical W.  2003.  A cyclic carbonate and related polyketides from a marine-derived fungus of the genus Phoma. Phytochemistry. 64:571-574.   10.1016/s0031-9422(03)00272-3   AbstractWebsite

Two metabolites, phomoxin and phomoxide, as well as the previously synthesized antibiotic eupenoxide, have been isolated from the fermentation broth of a marine-derived fungus of the genus Phoma (strain CNC-651). The new compounds are highly oxygenated polyketides of a new structural class. Phomoxin contains an unusual cyclic carbonate functionality that is rare among natural products. The structures of the new metabolites were assigned by spectroscopic methods that relied heavily on 2D NMR spectroscopic analysis. (C) 2003 Elsevier Ltd. All rights reserved.

Long, BH, Carboni JM, Wasserman AJ, Cornell LA, Casazza AM, Jensen PR, Lindel T, Fenical W, Fairchild CR.  1998.  Eleutherobin, a novel cytotoxic agent that induces tubulin polymerization, is similar to paclitaxel (Taxol (R)). Cancer Research. 58:1111-1115. AbstractWebsite

Eleutherobin is a novel natural product isolated from a marine soft coral that is extremely potent for inducing tubulin polymerization in vitro and is cytotoxic for cancer cells with an IC50 similar to that of paclitaxel. This compound is cross-resistant along with other multidrug-resistant agents against P-glycoprotein-expressing cells and is cross-resistant with paclitaxel against a cell line that has altered tubulin. In mechanistic studies, eleutherobin shares with paclitaxel the ability to induce tubulin polymerization in vitro and is most likely cytotoxic by virtue of this mechanism, Human colon carcinoma cells exposed to eleutherobin contain multiple micronuclei and microtubule bundles, and they arrest in mitosis, depending on concentration, cell line, and length of exposure. These morphological abnormalities appearing in cultured cells are indistinguishable from those induced by paclitaxel. Electron microscopy reveals that eleutherobin induces homogeneous populations of long, rigid microtubules similar to those formed by paclitaxel. Thus, eleutherobin is a new chemotype with a mechanism of action similar to that of paclitaxel and, as such, has promising potential as a new anticancer agent.

Lorenz, P, Jensen PR, Fenical W.  1998.  Mactanamide, a new fungistatic diketopiperazine produced by a marine Aspergillus sp. Natural Product Letters. 12:55-60.   10.1080/10575639808048871   AbstractWebsite

Mactanamide (1), a new diketopiperazine containing the uncommon amino acid D-2,6-dihydroxyphenylalanine, has been isolated from the mycelium of an undescribed marine fungus of the genus Aspergillus. The new fungal strain was obtained from the surface of the brown marine alga Sargassum sp. collected near Mactan Island in the Philippines. The structure and absolute stereochemistry of I was determined by interpretation of spectral data, by comparison with model compounds, and by measurement of the CD spectra of its component amino acids.