@article {3946, title = {New terpenoid metabolites from the skin extracts, an egg mass, and dietary sponges of the Northeastern Pacific dorid nudibranch Cadlina luteomarginata}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {75}, number = {6}, year = {1997}, note = {ISI Document Delivery No.: XL704Times Cited: 27Cited Reference Count: 26}, month = {Jun}, pages = {773-789}, type = {Article}, abstract = {Chemical investigations of Cadlina luteomarginata skin extracts, egg masses, and dietary sponges have led to the identification of the novel terpenoids cadlinaldehyde (30), spongian 32, seco-spongian 35, 20-acetoxy-12-marginatone (38), and lutenolide (39) from the nudibranch skin extracts, the new drimane sesquiterpenoid 1 alpha,2 alpha-diacetoxyalbicanyl acetate (40) from the nudibranch{\textquoteright}s egg mass, and the new sesquiterpenoids O-methyl-9-oxofurodysininlactone (47), 2-oxomicrocionin-2-lactone (48), and O-methyl-2-oxomicrocionin-2-lactone (49), from the dietary sponge Pleraplysilla sp. The known terpenoids furodysinin (1), furodysin (16), marginatafuran (21), and 9,11-dihydrogracillin A (37), which have been frequently isolated from C. luteomarginata skin extracts, were found for the first time in extracts of the dietary sponges Pleraplysilla sp. and Aplysilla sp. One of the new terpenoids, cadlinaldehyde (30), has an unprecedented degraded sesterterpenoid skeleton.}, keywords = {APLYSILLA-GLACIALIS, CHEMICAL DEFENSE, MOLLUSKS, nudibranch, SPONGE, structure elucidation, terpenoids}, isbn = {0008-4042}, url = {://A1997XL70400025}, author = {Dumdei, E. J. and Kubanek, J. and Coleman, J. E. and Pika, J. and Andersen, R. J. and Steiner, J. R. and Clardy, J.} } @article {3174, title = {EFFECT OF CONTIGNASTEROL ON HISTAMINE-RELEASE INDUCED BY ANTIIMMUNOGLOBULIN-E FROM RAT PERITONEAL MAST-CELLS}, journal = {Journal of Pharmaceutical Sciences}, volume = {83}, number = {9}, year = {1994}, note = {ISI Document Delivery No.: PF413Times Cited: 26Cited Reference Count: 9}, month = {Sep}, pages = {1234-1235}, type = {Article}, abstract = {In rat peritoneal mass cells induced by anti-immunoglobulin E (anti-IgE), contignasterol (1) inhibited histamine release in a dose-dependent manner. On the other hand, a reduction product of contignasterol (2) did not inhibit histamine release from mast cells induced by anti-IgE.}, keywords = {SPONGE, steroids}, isbn = {0022-3549}, url = {://A1994PF41300008}, author = {Takei, M. and Burgoyne, D. L. and Andersen, R. J.} } @article {2894, title = {SYNTHESIS OF FUNCTIONALIZED HEXAHYDRO-1H-PHENALENE, OCTAHYDRO-1H-PHENALENE, AND DECAHYDRO-1H-PHENALENE VIA DIELS-ALDER REACTIONS OF 1-METHYLENE-4A-METHOXYCARBONYL-1,2,3,4,4A,5,6,7-OCTAHYDRONAPHTHALENE AND RELATED DIENES}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {71}, number = {9}, year = {1993}, note = {ISI Document Delivery No.: MC957Times Cited: 2Cited Reference Count: 14}, month = {Sep}, pages = {1463-1483}, type = {Article}, abstract = {The results of a study of Diels-Alder reactions of the bicyclic dienes 6-8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels-Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6-8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels-Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from -2:1 to -3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-H-1-phenalenes is demonstrated.}, keywords = {SPONGE}, isbn = {0008-4042}, url = {://A1993MC95700025}, author = {Piers, E. and Friesen, R. W. and Kao, P. and Rettig, S. J. and Trotter, J.} } @article {7365, title = {INVITRO SCREENING OF CRUDE EXTRACTS AND PURE METABOLITES OBTAINED FROM MARINE-INVERTEBRATES FOR THE TREATMENT OF BREAST-CANCER}, journal = {Cancer Chemotherapy and Pharmacology}, volume = {30}, number = {5}, year = {1992}, note = {ISI Document Delivery No.: JG989Times Cited: 31Cited Reference Count: 27}, month = {Sep}, pages = {401-406}, type = {Article}, abstract = {A total of 15 samples (crude extracts and pure secondary metabolites) obtained from marine invertebrates collected from the offshore waters of British Columbia, Papua New Guinea, and Sri Lanka have previously been shown to exert cytotoxic activity in the in vitro L1210 leukemic bioassay. We screened these metabolites for in vitro cytotoxic activity against the drug-sensitive breast-tumor cell lines MCF-7, T-47D, ZR-75- 1, and MDA-MB23 1; the multidrug-resistant and P-glycoprotein (Pgp)-positive breast-tumor cell lines MCF-7 Ad(r) and MDA-Al(r); and normal and malignant human breast epithelial cells (HBEC) in primary culture. Eight samples exhibited significant [drug concentration resulting in a 50\% decrease in cell growth as compared with controls (ED50), <25-mu-g/ml] dose-dependent cytotoxicity against the drug-sensitive cell lines; the ED50 values were as low as 0.004-mu-g/ml. Five of the eight samples exhibited significant cytotoxicity against the multidrug-resistant cell lines; the ED50 values were as low as 0.0006-mu-g/ml. Incubation of MCF-7 Ad(r) cells with varying concentrations of compounds in the presence of Adriamycin demonstrated that none of the compounds tested interfered with Pgp function. Results obtained using HBEC in primary culture showed a wide range of chemosensitivities for a given drug against tissue taken from different patients, demonstrating the uniqueness of the response of different individuals to chemotherapy.}, keywords = {BREAST CANCER, CELLS, chemotherapy, COLORIMETRIC ASSAY, GROWTH, INVITRO SCREENING, MARINE ORGANISMS, SPONGE, TUMOR}, isbn = {0344-5704}, url = {://A1992JG98900011}, author = {Stingl, J. and Andersen, R. J. and Emerman, J. T.} } @article {7003, title = {NEAMPHINE, A SULFUR-CONTAINING AROMATIC HETEROCYCLE ISOLATED FROM THE MARINE SPONGE NEAMPHIUS-HUXLEYI}, journal = {Tetrahedron Letters}, volume = {32}, number = {24}, year = {1991}, note = {ISI Document Delivery No.: FN524Times Cited: 9Cited Reference Count: 17}, month = {Jun}, pages = {2707-2710}, type = {Article}, abstract = {The structure of neamphine (1), a cytotoxic metabolite of the marine sponge Neamphius huxleyi, has been solved by single crystal x-ray diffraction analysis. Neamphine (1) represents the first example, either from nature or synthesis, of the imidazo[4,5-e]-1,2-thiazine ring system.}, keywords = {ALKALOIDS, CYTOTOXIC, HETEROCYCLE, NITROGEN, SPONGE, SULFUR, TUNICATE}, isbn = {0040-4039}, url = {://A1991FN52400003}, author = {De Silva, E. D. and Racok, J. S. and Andersen, R. J. and Allen, T. M. and Brinen, L. S. and Clardy, J.} } @article {7083, title = {TRITERPENOID GLYCOSIDES FROM THE NORTHEASTERN PACIFIC MARINE SPONGE XESTOSPONGIA-VANILLA}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {69}, number = {9}, year = {1991}, note = {ISI Document Delivery No.: GH861Times Cited: 7Cited Reference Count: 13}, month = {Sep}, pages = {1352-1364}, type = {Article}, abstract = {Isoxestovanin A (6), xestovanin B (7), xestovanin C (8), dehydroxestovanin A (9), epidehydroxestovanin A (10), dehydroxestovanin C (11), and secodehydroxestovanin A (12), seven new triterpenoid glycosides, have been isolated from the Northeastern Pacific sponge Xestospongia vanilla. The structures of the metabolites were determined by a combination of spectroscopic analysis and chemical degradation. The aglycone of 6 has the new isoxestovanane triterpenoid carbon skeleton. Compounds 7, 8, and 11 are the first X. vanilla triterpenoid glycosides known to contain three monosaccharide subunits.}, keywords = {C-13 ASSIGNMENTS, GLYCOSIDE, H-1, NMR, SPONGE, SUGARS, TRITERPENOID, XESTOSPONGIA}, isbn = {0008-4042}, url = {://A1991GH86100003}, author = {Morris, S. A. and Northcote, P. T. and Andersen, R. J.} }