Cumingianols G and H, new 14,18-cycloapoeuphane triterpenoids from the Taiwan C. DC.

Two new 14,18-cycloapoeuphane triterpenoids, cumingianols G (1) and H (2), along with 12 known compounds, cumingianol C (3), cumingianol A (4), cumingianol D (5), 3,3-ethylenedioxy-5α-cycloart-24-en-23-one (6), 24,25(,)-24,25-epoxy-20()-hydroxydammar-3-one (7), (3β,7α)-stigmast-5-ene-3,7-diol (8), 7α-hydroxystigmasterol (9), 7β-hydroxysitosterol (10), 7β-hydroxystigmasterol (11), ethylcholest-5-en-3-hydroxy-7-one (12), coniferaldehyde (13) and 4-hydroxy-3,5-dimethoxy-benzaldehyde (14), have been isolated from collected in Taiwan. The structures of these metabolites were determined through mass spectrometry and 1D and 2D NMR analyses, combined with comparisons to reference data. The cytotoxic effects of these isolates were evaluated against human oral squamous cell carcinoma (SCC2095), human breast adenocarcinoma (MCF-7), and human gastric adenocarcinoma (SCM-1).

Isosarcophytoxide Derivatives with a 2,5-Dihydrofuran Moiety from the Soft Coral .

The present chemical investigation on the organic extract of the soft coral has contributed to the isolation of four new cembranoids: 16- and 16-hydroperoxyisosarcophytoxides ( and ), 16- and 16-methoxyisosarcophytoxides ( and ), and a known cembranoid, lobocrasol (). The structures of all isolates were elucidated by detailed spectroscopic analysis. Their structures were characterized by a 2,5-dihydrofuran moiety, of which the relative configuration was determined by DU8-based calculation for long-range coupling constants ().

New 3,4--3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge sp.

Continuing chemical investigation of the Red Sea sponge sp. led to the isolation of four new 3,4--3,19-dinorspongian diterpenoid lactones, secodinorspongins A-D (-), along with a classical spongian diterpenoid lactone, sponginolide (). The chemical structures, including the absolute configurations of these compounds, were elucidated using the extensive spectroscopic study composed of 1D and 2D NMR data analyses, and a comparison between calculated-electronic-circular-dichroism (ECD) and experimental-circular-dichroism (CD) spectra.

Spongenolactones A-C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge sp.

Three new 5,5,6,6,5-pentacyclic spongian diterpenes, spongenolactones A-C (-), were isolated from a Red Sea sponge sp. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and the absolute configurations of were determined on the basis of comparison of the experimental circular dichroism (CD) and calculated electronic circular dichroism (ECD) spectra. Compounds - are the first 5,5,6,6,5-pentacyclic spongian diterpenes bearing an -hydroxy group at C-1.

The Chemically Highly Diversified Metabolites from the Red Sea Marine Sponge sp.

A polyoxygenated and halogenated labdane, spongianol (); a polyoxygenated steroid, 3β,5α,9α-trihydroxy-24-ethylcholest-7-en-6-one (); a rare seven-membered lactone B ring, (22,24)-ergosta-7,22-dien-3β,5α-diol-6,5-olide (); and an α,β-unsaturated fatty acid, ()-3-methyl-9-oxodec-2-enoic acid () as well as five known compounds, 10-hydroxykahukuene B (), pacifenol (), dysidamide (), 7,7,7-trichloro-3-hydroxy-2,2,6-trimethyl-4-(4,4,4-trichloro-3-methyl-1-oxobu-tylamino)-heptanoic acid methyl ester (), and the primary metabolite 2'-deoxynucleoside thymidine (), have been isolated from the Red Sea sponge sp. The stereoisomer of was discovered in , and metabolites and , isolated previously from red algae, were characterized unprecedentedly in the sponge. Compounds and have not been found before in the genus .

An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge sp. from the Red Sea.

Chemical investigation of a Red Sea sp. led to the isolation of four new compounds, i.e.

Bioactive Capnosanes and Cembranes from the Soft Coral .

Two new capnosane-based diterpenoids, flaccidenol A () and 7--pavidolide D (), two new cembranoids, flaccidodioxide () and flaccidodiol (), and three known compounds to were characterized from the marine soft coral , collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus for the first time.

Anti-Inflammatory Polyoxygenated Steroids from the Soft Coral Lobophytum michaelae.

Three new polyoxygenated steroids, michosterols A-C (-), and four known compounds (-) were isolated from the ethyl acetate (EtOAc) extract of the soft coral , collected off the coast of Taitung. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and comparison of the nuclear magnetic resonance (NMR) data with related steroids. The cytotoxicity of compounds - against the proliferation of a limited panel of cancer cell lines was assayed.

Krempfielins Q and R, two new eunicellin-based diterpenoids from the soft coral Cladiella krempfi.

Two new eunicellin-based diterpenoids, krempfielins Q and R (1 and 2), and one known compound cladieunicellin K (3) have been isolated from a Formosan soft coral Cladiella krempfi. The structures of these two new metabolites were elucidated by extensive spectroscopic analysis. Anti-inflammatory activity of new metabolites to inhibit the superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (FMLP/CB)-induced human neutrophil cells and cytotoxicity of both new compounds toward five cancer cell lines were reported.

Klymollins T-X, bioactive eunicellin-based diterpenoids from the soft coral Klyxum molle.

Five new eunicellin-based diterpenoids, klymollins T-X (1-5), along with two known compounds (6 and 7) have been isolated from the soft coral Klyxum molle. The structures of these new metabolites were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. Compound 5 was found to exert significant in vitro anti-inflammatory activity against LPS-stimulated RAW264.

Krempfielins N-P, New anti-inflammatory eunicellins from a Taiwanese soft coral Cladiella krempfi.

Three new eunicellin-type diterpenoids, krempfielins N-P (1-3), were isolated from a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and by comparison with spectroscopic data of related known compounds. Compound 3 exhibited activity to inhibit superoxide anion generation.

Krempfielins J-M, new eunicellin-based diterpenoids from the soft coral Cladiella krempfi.

New four eunicellin-based diterpenoids, krempfielins J-M (1-4) were isolated from the organic extract of a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated on the basis of extensive spectroscopic analysis. The structure of compound 2 is rare due to the presence of the highly oxygenated pattern.

Cytotoxic and anti-inflammatory eunicellin-based diterpenoids from the soft coral Cladiella krempfi.

Five new eunicellin-based diterpenoids, krempfielins E-I (1-5) and seven known compounds (6-12) were isolated from the organic extract of a Taiwanese soft coral Cladiella krempfi. The structures of the new metabolites were elucidated on the basis of extensive spectroscopic analysis. Metabolites 5, 6, 10 and 12 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines.

Simplexins P-S, eunicellin-based diterpenes from the soft coral Klyxum simplex.

Four new eunicellin-based diterpenes, simplexins P-S (1-4), and the known compound simplexin A (5), have been isolated from the soft coral Klyxum simplex. The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis, particularly 1D and 2D NMR experiments. Compounds 1 and 3-5 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines, 3 being the most cytotoxic.

Bioactive eunicellin-based diterpenoids from the soft coral Cladiella krempfi.

Four new eunicellin-based diterpenoids, krempfielins A-D (1-4), along with two known compounds (5 and 6) have been isolated from a soft coral Cladiella krempfi. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and by comparison with spectroscopic data of related known compounds. Compounds 5 and 6 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines.