In order to discover and develop new drug from soft corals and gorgonian corals of Taiwan, we have searched the bioactive metabolites from the organic extracts of three soft corals Nephthea chabrolii, Sinularia manaarensis, Sinularia leptoclados, and one Gorgonian of Briareum genus. This study had led to the isolation of fifty-five natural products (1¡V55), including seventeen new meroditerpenoid-related metabolites (1¡V7 and 9¡V18), two new C18 terpenoid¡Vrelated carboxylic acids (20 and 21), three new sesquiterpenoidalnatural products (22¡V24), and two new steroids (26 and 27), along with three known compounds (8, 19, and 25) from N. chabrolii; nine new cembrane-type
diterpenoids (28¡V36), along with two known cembranolides 37 and 38 from S.manaarensis; five new sesquiterpenoids (39¡V43), one steroid (47) isolated for the first time from natural sources and three known metabolites (44¡V46) from S.
leptoclados; and three new briarane-type derivatives (48¡V50) and five known briarane-type compounds (51¡V55) from Briareum sp. The structures of metabolites 1¡V55, including their stereochemistries have been established by detailed spectroscopic analyses, particularly mass, 2D NMR (1H¡V1H COSY, HMQC, HMBC, and NOESY) spectroscopy and by comparison with the related physical and spectral data form other known compounds. The relative configuration of metabolite 39 was further confirmed by X-ray single-crystal analysis. Furthermore, the biosyntheses of meroditerpenoids 1, 4, 11, and 20 were proposed. To the best of our knowledge, the incorporation of a methyl group of the related meroditerpene to form a naphthoquinone as discovered herein for the first time.
In above metabolites, two compounds (2 and 10) were found to exhibit significant inhibition against the growth of MCF 7, NCI-H460, and SF-268 tumor cells at 20 £gg/mL. Also, compound 2 exhibited significant cytotoxicity against the growth of MDA¡VMB¡V231cancer cell line, and moderate to weak
cytotoxicity against Hep G2 and A-549 cancer cell lines and metabolite 10 exhibited moderate to weak cytotoxicity toward MDA¡VMB¡V231, Hep G2 and A-549 cancer cell lines. Furthermore, Two cembranolides (34 and 35) exhibited moderate cytotoxicity against Hepa59T/VGH, KB, Hela, and Med cell lines.
| Identifer | oai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0811106-171414 |
| Date | 11 August 2006 |
| Creators | Su, Jui-hsin |
| Contributors | Chun-nan Lin, Ya-ching Shen, Ping-jyum Sung, Yang-chang Wu, Jyh-horng Sheu |
| Publisher | NSYSU |
| Source Sets | NSYSU Electronic Thesis and Dissertation Archive |
| Language | Cholon |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0811106-171414 |
| Rights | restricted, Copyright information available at source archive |
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