Secondary metabolites from the New Zealand marine sponge Mycale hentscheli
dc.contributor.author | Singh, Ameet Jonathan | |
dc.date.accessioned | 2011-03-15T22:50:44Z | |
dc.date.accessioned | 2022-10-25T05:32:34Z | |
dc.date.available | 2011-03-15T22:50:44Z | |
dc.date.available | 2022-10-25T05:32:34Z | |
dc.date.copyright | 2007 | |
dc.date.issued | 2007 | |
dc.description.abstract | The New Zealand marine sponge Mycale hentscheli is the source of three classes of biologically active secondary metabolites, each with a different activity profile. Mycalamides A, B and D (102-104) inhibit the elongation stage of protein synthesis, where 102 and 103 have also been shown to reverse the morphology of ras-transformed T-cells to normal. The dilactone macrolide pateamine (105) is also a protein synthesis inhibitor, but at the initiation stage of translation. The polyoxygenatcd macrolide peloruside A (106) has been shown to cause cells to accumulate in the G2-M phase of mitosis by promoting microtubule polymerisation much like the highly successful antitumor drug paclitaxel (Taxol) (1) and thus has become a promising pharmaceutical candidate and a popular synthetic target. A study of a wild sample of M. hentscheli collected from Kapiti Island initiated by West and continued in this study resulted in the isolation of 104, 106 and also revealed a new compound, peloruside B (141). Large-scale extractions of wild and aquacultured Pelorus Sound specimens of M. hentscheli using a combination of normal- and reversed-phase chromatographic methods and standard spectroscopic techniques resulted in the isolation of 102, 106 and three new compounds, mycalamide E (107). and pelorusides C-D (142-143). Mycalamide E (107), the 6-des-O-methyl analogue of mycalamide A (102) was found to be 30 times less cytotoxic than 102 across four cell lines. Peloruside B (141), the 3-des-O-methyl analogue of peloruside A (106) was found to be approximately three times less cytotoxic than 106, yet still arrested cells at the G2-M phase of mitosis. Peloruside C (142), identified as the 3,7-des-0-methyl-8,9-didehydroxy-8-ene analogue of peloruside A (106), was found to be cytotoxic at nanomolar concentrations 15 times less than 106 but showed no antimitotic activity. Peloruside D (143), containing the 16-membered macrolide ring but with an unusual cyclisation about the C-7 to C-l I region and deoxygenation at the C-8 position, was found to be inactive at micromolor concentrations against the HL-60 cell line. | en_NZ |
dc.format | en_NZ | |
dc.identifier.uri | https://ir.wgtn.ac.nz/handle/123456789/23301 | |
dc.language | en_NZ | |
dc.language.iso | en_NZ | |
dc.publisher | Te Herenga Waka—Victoria University of Wellington | en_NZ |
dc.subject | Marine metabolites | |
dc.subject | Mycale composition | |
dc.subject | Secondary metabolism | |
dc.subject | Sponges | |
dc.title | Secondary metabolites from the New Zealand marine sponge Mycale hentscheli | en_NZ |
dc.type | Text | en_NZ |
thesis.degree.discipline | Chemistry | en_NZ |
thesis.degree.grantor | Te Herenga Waka—Victoria University of Wellington | en_NZ |
thesis.degree.level | Masters | en_NZ |
thesis.degree.name | Master of Science | en_NZ |
vuwschema.type.vuw | Awarded Research Masters Thesis | en_NZ |
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