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Our chemical investigation on the soft coral Sinularia facile which was collected off the coast of Kengting, Taiwan, has led to the isolation of ten metabolites 1¡Ð10, including four cembranoids and six polyhydroxylated steroids. Cembranoids isolated are two new natural compounds, (3E,7E,11E,15E)-cembra-3,7,11,15-tetraen-1-ol (1) and (1R*,12R*,3E,7E,10E,15E)-cembra-3,7,10,15-tetraen-12-ol (2), and two known compounds diepoxycembrene A (3) and isocembrol A (4). Moreover, five new polyhydroxylated steroids, cholest-5-ene-1£\,3£]-diol- 11£\-monoacetate (5), cholesta-5,24-diene-1£\,3£] -diol-11£\-monoacetate (6), cholesta-5,24-diene-1£\,3£]-11£\-triol (7), 24- methylenecholesta-5-ene-1£\, 3£]-diol-11£\,18-diacetate (8) and 24(S)- methylcholest-5-ene-1£\,3£]-diol- 11£\-monoacetate (9), and one known compound, 24-methylenecholest-5- ene-1£\,3£],11£\-triol (10). The chemical structures of these compounds (1¡Ð10) were elucidated by spectroscopic evidences (IR, MS, 1D NMR, and 2D NMR) and by comparison of the spectral data of these compounds in the literature. Cytotoxicity of these compounds toward various cancer cell lines has also been determined.

In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of five soft corals including Sinularia lochmodes, Sinularia nanolobata, Sinularia grandilobata, Sinularia depressa and Lobophytum crassum. This study had led to the isolation of eighteen natural compounds 1¡Ð18, including seven new compounds, lochmolins A ¡Ð G (1 ¡Ð 7) from S. lochmodes, a new compound nanolobatolide (8) featuring with a new carbon skeleton from S. nanolobata, two new compounds grandilobatin G (9) and sinugrandisterol E (10) from S. grandilobata, a new compound depressoloide A (11) and a known compound sarcophytol L (12) from S.depressa, and three new compounds crassumolides G¡ÐI (13¡Ð15) along with three known compounds durmolides B and C (16 and 17) and sinularolide C (18) from L. crassum. The structures of compounds 1¡Ð18 were established by detailed spectral data analysis (IR, MS, 1D & 2D NMR) and by comparison with the spectral data of the related known compounds. The relative stereochemistries of compound 8 was further confirmed by X-ray single-crystal diffraction analysis. Among them, compounds 13¡Ð15 and 16¡Ð17 were found to show significant activity against the accumulation of the pro-inflammatory iNOS and COX-2 proteins at 10 £gM.

Investigation on the chemical constituents of the Formosan soft coral Sinularia gibberosa, collected by hand using scuba off the coast of Kenting, had led to the isolation of seven new cembranoids , gibberorenes A-G¡]2-8¡^, three new sterols, gibberoketosterol B¡]10¡^, gibberoepoxysterol¡]11¡^, gibberoketosterol C ¡]12¡^ along with two known compounds, (1Z,3E,7E,11S,12S,14S)-11,12-epoxycembra-1,3,7 -trien-14-ol¡]1¡^and gibberoketosterol¡]9¡^. The structures of 1-12 were elucidated on the basis of extensive spectroscopic analysis, including IR, MS, 1D, and 2D NMR. Cytotoxicities of 1-12 against a limited panel of cancer cell lines were also evaluated. Among these metablites, compounds 9 and 11 were found to exhibit moderate cytotoxicity toward MCF-7, A549, MDA-MB-231, and HepG2 tumor cells. The ability of 9 and 10 to inhibit the pro-inflammatory iNOS and COX-2 expression of LPS-stimulated RAW264.7 macrophage cells has been also estimated.

Chromatographic separation of methylene chloride extracts of Formosan soft coral Lemnalia cervicorni May (collected at Green Island off Taiwan) led to the isolation of four ylangene sesquiterpenoids, GN40-29 (1), GN40-79 (3), GN40-169 (4), and GN40-173 (5). Acetylation of GN40-29 (1) gave a derivative GN40-29a (2). Compounds 3-5 were new compounds. Compound 1 showed cytotoxicity against HT-29 cell, while compound 5 was cytotoxic to P-388 cells. The methylene chloride extracts of Formosan soft coral Dendronephthya spinifera Holm (collected at Green Island off Taiwan) were found to contain a new cadinene sesquiterpene, GN43-4 (6).

In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of two Formosan soft corals Sarcophyton crassocaule and Paralemnalia thyrsoides. This study had led to the isolation of forty-six natural compounds 1¡V46, including sixteen new cembrane¡Vtype diterpenoids, crassocolides A¡VP (1¡V16) and four known cembrane¡Vtype compounds 17¡V20 from S. crassocaule; nineteen new sesquiterpenoids and norsesquiterpenoids, paralemnone (21), isoparalemnone (22), paralemnol (23) and paralemnolins A¡VP (24¡V39), along with seven known compounds 40¡V46 from P. thyrsoides. The structures of these compounds were established by the detailed spectroscopic analysis (IR, MS, 1D¡B2D NMR) and by comparison with related physical and spectral data from other known compounds. The absolute configurations of 1-46 were determined using a modified Mosher's method for 1, 7, 22 and 27. The structures of 5, 21, 24 and 37 were further proven by X-ray diffraction analysis. The cytotoxicity of compounds 1-46 against a limited panel of cancer cell lines was also determined. Also, the activity of compounds 21-28, 35-37 and 41-42 to inhibit the pro-inflammatory iNOS and COX-2 protein expression of LPS-stimulated RAW264.7 macrophage cells has been estimated.

Marine organisms have attracted much attention as potential source for drugs over recent years. Soft corals have yielded many bioactive metabolites. Some of them have been examined for their pharmacological properties. For the process of drug discovery, we have examined bioactive metabolites from the organic extracts of two soft corals Sinularia gibberosa and Sarcophyton sp. collected off Formosan coast. This study had led to the isolation of forty-two natural products (1¡V42), including one new £]-caryophyllene-type sesquiterpenoid (1), four new xeniaphyllane-type norditerpenoids (2, 14, 16, and 17), fourteen new xeniaphyllane-type diterpenoids (3¡V13 and 18¡V20), one novel nor-humulene (15), seven new xeniaphyllane-type diterpenoids (21¡V26) with cyclic peroxyhemiketal (3,6-dihydro-1,2-dioxin-3-ol) moiety, and one new steroid (27), along with five known compounds (28¡V32) from Sinularia gibberosa. Three new cembrane-type diterpenoids (33¡V35), along with seven known cembranolides (36¡V42) were isolated from Sarcophyton sp. The structures of metabolites 1¡V42 including their stereochemistry 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 from other known compounds. In above metabolites, two compounds (8, 9) exhibited cytotoxicity against the growth of MCF-7, Hep 3B, Ca9-22 cancer cell lines. Furthermore, nine compounds (4, 8, 9, 11, 12, 13, 21, 31, 39) exhibited cytotoxicity against the growth of MDA-MB-231, Hep G2 and A-549 cancer cell lines.

In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of the soft coral Sarcophyton crassocaule. This study had led to the isolation of twenty-six natural cembrane-type diterpenoids, compounds 1¡V26, including eighteen new compounds, sarcocrassocolide A¡VR (1¡V18), along with six know compounds, crassocolide A, B, D, E, L, sarcocrassolide, sinularolide E and 13-acetoxysarcocrassolide (19¡V26). The structures of compounds 1¡V26 were established by detailed spectroscopic data analysis (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with those of the related known compounds. The structures of 8, 9 and 11 were further established by orgamic methods, and the absolute configuration of 1 was determined using a modified Mosher¡¦s method. The cytotoxicity of compounds 1¡V17 and 19¡V21 against the Daoy (human medulloblastoma), HEp2 (human laryngeal carcinoma), MCF-7 (human breast adenocarcinoma), WiDr (human colon adenocarcinoma), DLD-1 (human colon adenocarcinoma), CCRF-CEM (human T-cell acute lymphoblastic leukemia), and HL-60 (human promyelocytic leukemia) tumor cell lines were determined, and structure-activity relationship was presented by statistic method. Compounds 3 and 9 showed significant activity toward the above Daoy, HEp2, MCF7 and WiDr, and compounds 18, 19, 20, 22 and 24 were found to show significant activity toward the above DLD-1, CCRF-CEM and HL-60. Compounds 1¡V26 were shown to exert significant anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells. Compounds 9, 17, 19, 22 and 24 also significantly inhibited the accumulation of pro-inflammatory COX-2 protein.

In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of the soft coral Sarcophyton stellatum, collected from Dongsha Atoll. This study had led to the identification of sixteen natural diterpenoids, including six new compounds, stellatumonone (1), stellatumolides A¡VC (2¡V4) and stellatumonins A¡VB (5¡V6), along with ten known compounds. The structures of compounds 1¡V16 were established by detailed spectroscopic data (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with those of the related known compounds. The cytotoxicity of compounds 1¡V16 against the HepG2 (human liver hepatocellular carninoma cells), MDA-MB231 (human breast cancer cells) and A549 (human respiratory epithelial cells) cancer cell lines were determined. Among them, compound 16 showed cytotoxic activity toward the A549 cancer cells.

Abstract In our continuing studies on the chemical constituents of Taiwanese octocorals, the gorgonian coral Isis hippuris and the sea pen coral Virgularia juncea, which were collected from the coast of Green Island and Peng-Hung Islands, respectively, have been the subjects of our investigations. Six compounds, including two new steroids, hippuristerones A and E (1 and 2), along with three known steroids 3£]-hydroxy-5£\-pregnan -20-one (3), prenga-4-ene-3,20-dione (4), prenga-1,4-diene-3,20-dione (5) and a known sesquiterpene subergorgic acid (6) were isolated from I. hippuris. Four compounds, incoulding a new sesquterpene, junceol A (7) and two known diterpenoids, sclerophytin A (8), cladiellisin (9) and a known steroid 24-methylenecholesterol (10) were isolated from V. juncea. The structures of above isolates were determined by physical (mp and optical rotation) and extensive spectral (UV, IR, MS, HRMS, 1D and 2D NMR) analysis and by comparison with the related physical and spectral data from other known compounds. The structure, including the relative configuration of hippuristerone A (1) was further confirmed by a single-crystal X-ray analysis.Furthermore, the relative configuration of hippuristerone E (2) was supported by the chemical dynamics calculations.