@article {2385, title = {A Peterson avenue to 5-alkenyloxazoles}, journal = {Tetrahedron Letters}, volume = {50}, number = {45}, year = {2009}, note = {ISI Document Delivery No.: 506HLTimes Cited: 3Cited Reference Count: 50Chau, Jaclyn Zhang, Jianmin Ciufolini, Marco A.}, month = {Nov}, pages = {6163-6165}, type = {Article}, abstract = {The TiCl4-promoted Peterson olefination of aldehydes with readily available 5-(trimethylsilyl)methyloxazoles furnishes 5-alkenyloxazoles (mostly E-isomers). (C) 2009 Elsevier Ltd. All rights reserved.}, keywords = {CALYCULIN, CHEMISTRY, CONSTRUCTION, HETEROCYCLIC-DERIVATIVES, inhibitors, NATURAL-PRODUCTS, OXAZOLES, PHORBOXAZOLE, PSEUDOMONIC ACID, SIPHONAZOLE}, isbn = {0040-4039}, url = {://000270765700015}, author = {Chau, J. and Zhang, J. M. and Ciufolini,Marco A.} } @article {2660, title = {Pyrodysinoic Acid Derivatives from the Marine Sponge Dysidea robusta}, journal = {Journal of Natural Products}, volume = {72}, number = {9}, year = {2009}, note = {ISI Document Delivery No.: 507LSTimes Cited: 1Cited Reference Count: 30Williams, David E. Marques, Suzi O. Hajdu, Eduardo Peixinho, Solange Andersen, Raymond J. Berlinck, Roberto G. S.}, month = {Sep}, pages = {1691-1694}, type = {Article}, abstract = {Three new nitrogen-containing terpenes related to pyrodysinoic acid (1) have been isolated from the sponge Dysidea robusta collected in Brazil. Isopyrodysinoic acid (2), 13-hydroxyisopyrodysinoic acid (3), and pyrodysinoic acid B (4) were obtained from the crude extract of D. robusta and identified by analysis of spectroscopic data. Pyrodysinoic acid B (4) is the first furodysin or furodysinin sesquiterpene derivative with a trans junction between the two six-membered rings of the 1,2,3,4,4a,7,8,8a-octahydro-1,1,6-trimethylnaphthalene moiety.}, keywords = {AMINO-ACID, biosynthesis, CELLULAR-ORIGIN, DENDROLASIN, DYSIHERBAINE, GENUS DYSIDEA, HERBACEA, METABOLITES, NATURAL-PRODUCTS, SESQUITERPENES}, isbn = {0163-3864}, url = {://000270855600026}, author = {Williams, D. E. and Marques, S. O. and Hajdu, E. and Peixinho, S. and Andersen, R. J. and Berlinck, R. G. S.} } @article {2661, title = {Rolloamides A and B, Cytotoxic Cyclic Heptapeptides Isolated from the Caribbean Marine Sponge Eurypon laughlini}, journal = {Journal of Natural Products}, volume = {72}, number = {7}, year = {2009}, note = {ISI Document Delivery No.: 479MVTimes Cited: 3Cited Reference Count: 14Williams, David E. Yu, Ker Behrisch, Hans W. Van Soest, Rob Andersen, Raymond J.}, month = {Jul}, pages = {1253-1257}, type = {Article}, abstract = {Two cyclic heptapeptides, rolloamides A (1) and B (2), have been isolated from the Dominican marine sponge Eurypon laughlini. The structures of 1 and 2 were elucidated by a combination of spectroscopic analyses and chemical degradation. Rolloamide A (1), which was found to exist as two distinct conformers in C5D5N, exhibits growth suppressive activity against a panel of histologically diverse cancer cell lines.}, keywords = {NATURAL-PRODUCTS, OCTAPEPTIDE, PEPTIDES, PORIFERA, PROLINE, STYLOTELLA-AURANTIUM}, isbn = {0163-3864}, url = {://000268664500006}, author = {Williams, D. E. and Yu, K. and Behrisch, H. W. and Van Soest, R. and Andersen, R. J.} } @article {2055, title = {A synthetic approach to the fusicoccane A-B ring fragment based on a Pauson-Khand cycloaddition/Norrish type 1 fragmentation}, journal = {Journal of Organic Chemistry}, volume = {73}, number = {17}, year = {2008}, note = {ISI Document Delivery No.: 344EDTimes Cited: 1Cited Reference Count: 88Dake, Gregory R. Fenster, Erik E. Patrick, Brian O.}, month = {Sep}, pages = {6711-6715}, type = {Article}, abstract = {A synthetic approach to the A-B ring system within the fusicoccane family of diterpenes is presented. Key steps in this approach are a diastereoselective Pauson-Khand reaction, a Norrish 1 photofragmentation, a Charette cyclopropanation, and a ring-closing metathesis process.}, keywords = {ALLYLIC ALCOHOLS, BICYCLIC SYSTEMS, CARBONYL-COMPOUNDS, CEROPLASTIN NUCLEUS, CLOSING METATHESIS, CYCLIZATION, DOLASTANE DITERPENES, ENYNE METATHESIS, NATURAL-PRODUCTS, NAZAROV, ORGANIC-SYNTHESIS}, isbn = {0022-3263}, url = {://000258908000030}, author = {Dake, G. R. and Fenster, E. E. and Patrick, B. O.} } @article {1407, title = {Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase}, journal = {Journal of Organic Chemistry}, volume = {71}, number = {23}, year = {2006}, note = {ISI Document Delivery No.: 101QKTimes Cited: 14Cited Reference Count: 23Gray, Christopher A. de Lira, Simone P. Silva, Marcio Pimenta, Eli F. Thiemann, Otavio H. Oliva, Glaucius Hajdu, Eduardo Andersen, Raymond J. Berlinck, Roberto G. S.}, month = {Nov}, pages = {8685-8690}, type = {Article}, abstract = {Three new disulfated meroterpenoids, ilhabelanol (1), ilhabrene (2), and isoakaterpin (3), have been isolated from extracts of the Brazilian marine sponge Callyspongia sp. Isoakaterpin (3) inhibits Leishmania spp. adenosine phosphoribosyl transferase with an IC50 of 1.05 mu M. The structures of 1, 2, and 3 were elucidated by analysis of one- and two-dimensional NMR data. Ilhabelanol (1) and ilhabrene (2) both have unprecedented meroterpenoid carbon skeletons.}, keywords = {AKA ADOCIA SP, AKATERPIN, chemotherapy, DRUGS, HEXAPRENOID HYDROQUINONES, LEISHMANIASIS, NATURAL-PRODUCTS, TOXICLONA-TOXIUS}, isbn = {0022-3263}, url = {://000241755300001}, author = {Gray, C. A. and de Lira, S. P. and Silva, M. and Pimenta, E. F. and Thiemann, O. H. and Oliva, G. and Hajdu, E. and Andersen, R. J. and Berlinck, R. G. S.} } @article {1300, title = {Dominicin, a cyclic octapeptide, and laughine, a bromopyrrole alkaloid, isolated from the Caribbean marine sponge Eurypon laughlini}, journal = {Journal of Natural Products}, volume = {68}, number = {3}, year = {2005}, note = {ISI Document Delivery No.: 910JPTimes Cited: 15Cited Reference Count: 9}, month = {Mar}, pages = {327-330}, type = {Article}, abstract = {Dominicin, a new cyclic peptide, and the new bromopyrrole alkaloid laughine (4) have been isolated from the marine sponge Eurypon laughlini collected in Dominica. The structures of 1 and 4 were determined by a combination of spectroscopic analysis and chemical degradation. Single-crystal X-ray diffraction analysis confirmed the structure of dominicin (1).}, keywords = {NATURAL-PRODUCTS, PROLINE}, isbn = {0163-3864}, url = {://000227927700004}, author = {Williams, D. E. and Patrick, B. O. and Behrisch, H. W. and Van Soest, R. and Roberge, M. and Andersen, R. J.} } @article {1032, title = {Boneratamides A-C, new sesquiterpenoids isolated from the marine sponge Axinyssa aplysinoides}, journal = {Journal of Natural Products}, volume = {67}, number = {10}, year = {2004}, note = {ISI Document Delivery No.: 865MRTimes Cited: 4Cited Reference Count: 14}, month = {Oct}, pages = {1752-1754}, type = {Article}, abstract = {Three new sesquiterpenoids, boneratamides A (1)-C (3), have been isolated as their methyl esters 4-6 from extracts of the marine sponge Axinyssa aplysinoides collected in Indonesia. The structures of methyl esters 4-6 were elucidated by analysis of spectroscopic data and confirmed by single-crystal X-ray diffraction analysis of 4.}, keywords = {AGENT, ANALOGS, BINDING, HEMIASTERLIN, NATURAL-PRODUCTS, PACLITAXEL, TUBULIN}, isbn = {0163-3864}, url = {://000224707700025}, author = {Williams, D. E. and Patrick, B. O. and Tahir, A. and Van Soest, R. and Roberge, M. and Andersen, R. J.} } @article {1029, title = {Pachymoside A - A novel glycolipid isolated from the marine sponge Pachymatisma johnstonia}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {82}, number = {2}, year = {2004}, note = {ISI Document Delivery No.: 802BHTimes Cited: 5Cited Reference Count: 21}, month = {Feb}, pages = {102-112}, type = {Article}, abstract = {Crude extracts of the North Sea marine sponge Pachymatisma johnstonia showed promising activity in a new assay for inhibitors of bacterial type III secretion. Bioassay-guided fractionation resulted in the isolation of the pachymosides, a new family of sponge glycolipids. A major part of the structural diversity in this family of glycolipids involves increasing degrees of acetylation and differing positions of acetylation on a common pachymoside glycolipid template. All of the metabolites with these variations in acetylation pattern were converted into the same peracetylpachymoside methyl ester (2) for purification and spectroscopic analysis. Pachymoside A (1) is the component of the mixture that has natural acetylation at the eight galactose hydroxyls and at the C-6 hydroxyls of glucose-B and glucose-D. Chemical degradation and transformation in conjunction with extensive analysis of 800 MHz NMR data was used to elucidate the structure of pachymoside A (1).}, keywords = {BACTERIAL VIRULENCE, ENTEROPATHOGENIC ESCHERICHIA-COLI, glycolipid, GLYCOSPHINGOLIPIDS, HOST-CELLS, III SECRETION, inhibitors, marine sponge, NATURAL-PRODUCTS, Pachymatisma johnstonia, pachymoside, PLAKORTIS-SIMPLEX, PLAKOSIDE, PRENYLATED, RECEPTOR}, isbn = {0008-4042}, url = {://000220138500006}, author = {Warabi, K. and Zimmerman, W. T. and Shen, J. K. and Gauthier, A. and Robertson, M. and Finlay, B. B. and Van Soest, R. and Andersen, R. J.} } @article {337, title = {Tupuseleiamides and basiliskamides, new acyldipeptides and antifungal polyketides produced in culture by a Bacillus laterosporus isolate obtained from a tropical marine habitat}, journal = {Journal of Natural Products}, volume = {65}, number = {10}, year = {2002}, note = {ISI Document Delivery No.: 609YZTimes Cited: 13Cited Reference Count: 14}, month = {Oct}, pages = {1447-1451}, type = {Article}, abstract = {Laboratory cultures of PNG 276, a Bacillus laterosporus isolate obtained from coastal waters off Papua New Guinea, have been shown to produce the novel metabolites basiliskamide A (1), basiliskamide B (2), tupuseleiamide A (3), and tupusleiamide B (4). The structures of I to 4 were elucidated by analysis of spectroscopic data and chemical degradation. Basiliskamides A (1) and B (g) show potent in vitro anti-Candida, activity.}, keywords = {ANTIBIOTIC-RESISTANCE, BACTERIUM, MICROORGANISMS, NATURAL-PRODUCTS, STEREOCHEMISTRY, YM-47522}, isbn = {0163-3864}, url = {://000178935100011}, author = {Barsby, T. and Kelly, M. T. and Andersen, R. J.} } @article {5222, title = {Stereocontrolled construction of the A-ring of nitiol using a Pauson-Khand cycloaddition-ring fragmentation strategy}, journal = {Organic Letters}, volume = {3}, number = {13}, year = {2001}, note = {ISI Document Delivery No.: 445ZDTimes Cited: 5Cited Reference Count: 24}, month = {Jun}, pages = {2041-2044}, type = {Article}, abstract = {[GRAPHICS] A stereocontrolled construction of the A-ring of nitiol (1) is presented, Key features in this approach are a diastereoselective Pauson-Khand cycloaddition and a Norrish type 1 fragmentation reaction.}, keywords = {ACID, ACTIVE BICYCLO<3.3.0>OCTENONE DERIVATIVES, ALDER, ALKENE ALKYNE CYCLIZATIONS, ENZYME-CATALYZED-HYDROLYSIS, NATURAL-PRODUCTS}, isbn = {1523-7060}, url = {://000169487700020}, author = {Wilson, M. S. and Dake, G. R.} } @article {3876, title = {Cytotoxic peptides hemiasterlin, hemiasterlin A and hemiasterlin B induce mitotic arrest and abnormal spindle formation}, journal = {Cancer Chemotherapy and Pharmacology}, volume = {39}, number = {3}, year = {1997}, note = {ISI Document Delivery No.: VZ251Times Cited: 66Cited Reference Count: 17}, month = {Jan}, pages = {223-226}, type = {Article}, abstract = {Purpose: Hemiasterlin, hemiasterlin A and hemiasterlin B are newly isolated cytotoxic tripeptides with potential as antitumor drugs. We wished to determine their mechanism of cytotoxicity. Methods: We studied their effect on cell survival, cell cycle progression, and microtubule morphology in MCF-7 human mammary carcinoma cells. Results: At the nanomolar concentrations at which they were cytotoxic, the peptides induced arrest in mitotic metaphase. Hemiasterlin A produced abnormal mitotic spindles like those produced by the microtubule inhibitors taxol, nocodazole and vinblastine at low concentrations. At high concentrations hemiasterlin A did not cause microtubule bundling like taxol, but caused microtubule depolymerization like nocodazole and vinblastine. Conclusions: The hemiasterlins probably exert their cytotoxic effect by inhibiting spindle microtubule dynamics.}, keywords = {CANCER, COLCHICINE SITE, FOSTRIECIN, INHIBITION, microtubules, mitosis, NATURAL-PRODUCTS, OKADAIC ACID, PHOSPHATASE-2A, PODOPHYLLOTOXIN, TAXOL, TUBULIN, VINBLASTINE, VINCA DOMAIN}, isbn = {0344-5704}, url = {://A1997VZ25100008}, author = {Anderson, H. J. and Coleman, J. E. and Andersen, R. J. and Roberge, M.} } @article {6792, title = {GEOGRAPHICAL VARIATION IN DEFENSIVE CHEMICALS FROM PACIFIC COAST DORID-NUDIBRANCHS AND SOME RELATED MARINE MOLLUSKS}, journal = {Comparative Biochemistry and Physiology C-Pharmacology Toxicology \& Endocrinology}, volume = {97}, number = {2}, year = {1990}, note = {ISI Document Delivery No.: EV555Times Cited: 35Cited Reference Count: 38}, pages = {233-240}, type = {Article}, abstract = {1. Comparison of the chemical constituents of geographically diverse collections of six dorid nudibranchs has revealed that those species that are capable of de novo biosynthesis of defensive metabolites always produce the same array of chemicals. 2. Conversely, those species that acquire chemicals from their sponge diet have a variable chemical arsenal. 3. It is proposed that chemical consistency be used as an indicator of the origin of chemicals in the defensive arsenal of dorid nudibranchs.}, keywords = {ACANTHODORIS-NANAIMOENSIS, ACID GLYCERIDES, CADLINA-LUTEOMARGINATA, CARBON, CHROMODORIS-MACFARLANDI, DIAULULA-SANDIEGENSIS, INVERTEBRATES, METABOLITES, NATURAL-PRODUCTS, SKELETON, SKIN EXTRACTS}, isbn = {0742-8413}, url = {://A1990EV55500005}, author = {Faulkner, D. J. and Molinski, T. F. and Andersen, R. J. and Dumdei, E. J. and De Silva, E. D.} }