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Study On Chemical Constituents Of Marine Sponge Strepsichordaia Sp. From Xisha Islets

Posted on:2015-08-28Degree:MasterType:Thesis
Country:ChinaCandidate:F R MuFull Text:PDF
GTID:2284330467459303Subject:Pharmaceutical
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Apart from the Coral, marine sponge, which spreads all over the world, is the second largestinvertebrate animals in the ocean. Marine sponges are exposed to a variety of dangers in theirenvironment and this led to the development of chemical defense mechanisms againstpredation. Additionally, sponges are a rich source of biologically metabolites, which attractslots of experts dedicated to exploring natural products from marine sponge. For almost halfcentury, natural products experts attained diverse compounds from marine sponge, whichconsists of enyne compounds, steroids, alkaloids, terpenoids, peptides, macrolides and othertypes of compounds. These metabolites have displayed a wide spectrum of interestingbiological properties including anti-microbial, antifouling, cytotoxic, antitumor, antiviral,immunomudulatory effects and enzymes inhibition. For this reason, lots of compoundspossess potential clinical application.The sponge strepsichordaia sp. belongs to Thorectidae family, order Dictyoceratida,Demospongiae and spongia. Since this specimen is quite hard to touch, it s biologically activemetabolites has not been explored to the best. Up to date, according to previous reports, onlya series of scalarane-based sesterterpenes and several ceramides with moderate cytotoxicactivity have been isolated from the sponge. In order to explore structurally and biologicallydiversity of secondary metabolites from marine sponges collected along South China Sea, ourgroup have systematically studied the chemical components and their bioactivities of thesponge collected in June,2007and July,2013respectively.In our study, the crude extracts were subjected to VLC, normal-phase silica gel, ODS,Sephadex-LH-20and reverse-HPLC chromatography,28compounds were isolated from thedichloromethane-soluble and petroleum ether-soluble fractions. Based on UV, IR,HRESEMS, NMR, CD and X-ray data, as well as relative reference, we finally elucidatedtheir structures including9scalarane-based sesterterpenes (1-9), one steroid (10), onepolyketide (11),15quinone sesquiterpenes (12-16,18-27) and one fatty acid (17). Thesecompounds are identified as follows, honulactone M (1),12-acetoxy-24-hydroxyscalar-17-ene-18,25-carbolactone (2), honulactone A (3), honulactone B (4), honulactone E (5), honulactone F (6), honulactone I (7), honulactone J (8),scalarin (9), β-sitosterol (10),(-)-Methyl (2Z,6R,8R,9E)-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (11), strepol A (12), strepol B (13),strepoceratin (14), streplactone (15), strepaminone B (16),(Z)-9-ene-5-yne pentacosanecarboxylic acid (17), dictyoceratin A (18), dactylcquinone A (19), dactyloquinone D (20),neodactyloquinone (21), dactyloqulnone D (22), ilimaquinone (23), dactyloqulnone C (24),smenospongidine (25), smenospongia(26), smenospongrine (27), among which compound1and2were new scalarane sesterterpenes, compound12,13,14,15,16,17were new quinonesesquiterpenes, compound17were new carboxylic acid, but cytotoxic test showed thatcompound2-6,8-11did not exhibit inhibitory activity on multiple myeloma cells8266.
Keywords/Search Tags:sponge, strepsichordaia, scalarane-based sesterterpenes, quinonesesquiterpenes, bioactivities
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