Okinawan Soft Coral Clavularia Viridis Research Articles

Isolation of Three Marine Prostanoids, Possible Biosynthetic Intermediates for Clavulones, from the Okinawan Soft Coral Clavularia viridis

Three marine prostanoids, 1, 2, and 3, were isolated from the extract of the Okinawan soft coral Clavularia viridis. The structures of these compounds were assigned based on the results of spectroscopic analysis. Compound 1 was shown to be preclavulone-A methyl ester, and this is the first isolation of the ester of preclavulone-A as a natural product. Preclavulone-A is proposed to be the key intermediate in the biosynthesis of marine prostanoids exemplified by clavulones in C. viridis. The new prostanoid 3 was suggested to be a biosynthetic intermediate from preclavulone-A to clavulones, and a possible biogenetic pathway via 3 is proposed.

Isolation and structures of new halogenated prostanoids from the Okinawan soft coral Clavularia viridis.

Fifteen new halogenated prostanoids 9-23 were isolated as minor constituents from the Okinawan soft coral Clavularia viridis. Compounds 9-11 were new members of iodovulone, and compounds 12-18 were 12-O-acetyliodovulones, 12-O-acetylbromovulones, and 12-O-acetylchlorovulones. Compounds 19-23 were 10,11-epoxy congeners of iodovulone, bromovulone, and chlorovulone. The structures of these compounds were determined on the basis of spectroscopic analysis and chemical conversion.

Localization of clavulons, prostanoids with antitumor activity, within the Okinawan soft coral Clavularia viridis (alcyonacea, clavulariidae): Preparation of a high‐purity Symbiodinium faction using a protease and a detergent

To investigate the localization of clavulones (CV), prostanoids with antitumor activity, in the Okinawan soft coral Clavularia viridis, we developed a method for the isolation of Symbiodinium cells from the coral, i.e., treatment of a coral homogenate with a protease, pronase E, and a detergent, Nonidet P-40. The conditions for the treatment were optimized by monitoring the morphology microscopically and the amount of chlorophyll in the Symbiodinium fraction (SymF) optically. To evaluate the purity of SymF and a Symbiodinium-free coral fraction (CorF), we analyzed them for proteins and lipids using cultivated Symbiodinium as a reference. TLC of lipids revealed that SymF contained a greater amount of glycolipids, whereas CorF comprised mostly phospholipids. SDS-PAGE of proteins in SymF and CorF revealed their distinct profiles. Thus, we could obtain each fraction with high purity; we reached the conclusion that CV and arachidonic acid, their possible precursor, are localized exclusively in the insoluble fraction of host coral cells.

Studies on Discovery and Synthesis of Bioactive Marine Organic Molecules

AbstractFor Abstract see ChemInform Abstract in Full Text.

Isolation of three marine prostanoids, possible biosynthetic intermediates for clavulones, from the Okinawan soft coral Clavularia viridis.

Three marine prostanoids, 1, 2, and 3, were isolated from the extract of the Okinawan soft coral Clavularia viridis. The structures of these compounds were assigned based on the results of spectroscopic analysis. Compound 1 was shown to be preclavulone-A methyl ester, and this is the first isolation of the ester of preclavulone-A as a natural product. Preclavulone-A is proposed to be the key intermediate in the biosynthesis of marine prostanoids exemplified by clavulones in C. viridis. The new prostanoid 3 was suggested to be a biosynthetic intermediate from preclavulone-A to clavulones, and a possible biogenetic pathway via 3 is proposed.

Isolation of peridinin-related norcarotenoids with cell growth-inhibitory activity from the cultured dinoflagellate of Symbiodinium sp., a symbiont of the Okinawan soft coral Clavularia viridis, and analysis of fatty acids of the dinoflagellate.

Two norcarotenoids, 1 and 2, related to peridinin (3) were isolated from the cultured dinoflagellate of the genus Symbiodinium, a symbiont of the Okinawan soft coral Clavularia viridis, which contains in abundance antitumor marine prostanoids such as clavulones. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis. These compounds showed significant growth-inhibitory activity in vitro toward cancer cells. Analysis of fatty acids of the dinoflagellate was also carried out, suggesting that the marine prostanoids are produced by the host soft coral itself.

Tricycloclavulone (I) and Clavubicyclone (II), Novel Prostanoid‐Related Marine Oxylipins, Isolated from the Okinawan Soft Coral Clavularia viridis.

Tricycloclavulone (I) and Clavubicyclone (II), Novel Prostanoid‐Related Marine Oxylipins, Isolated from the Okinawan Soft Coral Clavularia viridis.

Studies on discovery and synthesis of bioactive marine organic molecules

This paper describes the discovery and total synthesis of bioactive marine natural products conducted in our laboratory. Clavulone, chlorovulone, bromovulone, and iodovulone are antitumor marine prostanoids isolated from the Okinawan soft coral Clavularia viridis. The synthesis of clavulone and chlorovulone was achieved from chiral 4-hydroxy-2-cyclopentenone. Marine prostanoid punaglandins 3 and 4 were synthesized via similar methodology. The chemical structures of punaglandins 3 and 4 were revised by these syntheses. Dollaberane-type diterpenoid stolonidiol and claenone were isolated from Okinawan soft coral Clavularia sp. Stolonidiol showed potent choline acetyltransferase-inducible activity in cultured basal forebrain cells. The synthesis of stolondiol and claenone was conducted via sequential Michael reaction and retro-aldol reaction. Aragusterols, isolated from the Okinawan marine sponge Xestospongia sp., are structurally unique steroids possessing a rare 26,27-cyclo structure in the side chain. Aragusterols express potent in vivo antitumor activity against L1210 leukemia in mice. The synthesis of aragusterols was carried out via steroselective construction of the side chain and stereocontrolled coupling reaction with the steroid skeleton. Kalihinane-type diterpenoid kalihinol A, isolated by Scheuer, has remarkable in vitro antimalarial activity. The absolute configuration of kalihinol A was determined by applying the CD exciton chiral method. Synthesis of kalihinene X, a kalihinane-type diterpenoid, was achieved. This synthesis involves the regioselective coupling reaction of carbanion of alkyl sulfone with epoxyalcohol and construction of cis-decalin by an intramolecular Diels-Alder reaction.

Tricycloclavulone and clavubicyclone, novel prostanoid-related marine oxylipins, isolated from the Okinawan soft coral Clavularia viridis.

Two novel prostanoid-related marine oxylipins, tricycloclavulone (1) and clavubicyclone (2), were isolated from the Okinawan soft coral Clavularia viridis. The structures of 1, having a tricyclo[5.3.0.0(1,4)]decane ring system, and 2, having a bicyclo[3.2.1]octane ring system, were elucidated on the basis of spectroscopic analysis. Clavubicyclone showed a moderate growth inhibition activity against tumor cells in vitro.

New Halogenated Marine Prostanoids with Cytotoxic Activity from the Okinawan Soft Coral Clavularia viridis

Five new halogenated prostanoids 1-4 and 6 were isolated from the Okinawan soft coral Clavularia viridis. The gross structure of 1 was elucidated mainly on the basis of NMR spectral data. The relative and absolute configurations were determined by analysis of NOESY and CD data, chemical conversion, and the modified Mosher's method. The structures of 2-4 and 6 were deduced by comparison of their spectral data with those of 1. Compound 1 demonstrated cytotoxic activity.

New bioactive marine steroids from the Okinawan soft coral Clavularia viridis

Eight new marine steroids were isolated from the Okinawan soft coral Clavularia viridis Quoy and Gaimard. Their structures were determined based on spectroscopic analysis, chemical conversion, and X-ray crystallographic analysis. Steroids 5 and 6 showed growth inhibition activity toward HeLa S3 cells and human diploid cells in vitro.

New Marine Prostanoid Carboxylate Salts from the Okinawan Soft Coral Clavularia viridis

Two new marine prostanoid carboxylate salts were isolated from the polar fraction of the Okinawan soft coral Clavularia viridis. Their structures, including absolute configurations, were determinded based on the results of spectroscopic analysis and chemical conversion to known compounds.

New prostanoids from soft coral

Four new anti-tumor active prostanoids, named claviridenone-a ( 3), claviridenone-b ( 4). claviridenone-c ( 5), and claviridenone-d ( 6), as well as 20-acetoxy-claviridenone-b ( 7) and 20-acetoxy-claviridenone-c ( 8), have been isolated from the Okinawan soft coral (stolonifer) Clavularia viridis Quoy and Gaimard (Stolonifera, Clavulariidae). The absolute stereostructures of these six prostanoids have been elucidated on the basis of chemical and physicochemical evidence which includes the application of the CD exciton chirality method to their various benzoyl derivatives having benzoate and conjugated diene chromophores. Claviridenones possess a characteristic cross-conjugated dienone-enone chromophore.

Stoloniferone-a, -b, -c, and -d, four new cytotoxic steroids from the okinawan soft coral clavularia viridis

Four new cytotoxic steroids named stoloniferone-a (7a), -b (7b), -c (7c), and -d (7d) were isolated from the stoloniferan Okinawan soft coral Clavularia viridis and their absolute stereostructures were elucidated.

Absolute stereostructures of claviridenone-A, -B, -C, and -D four prostanoids from the Okinawan soft coral Clavularia viridis.

By means of the circular dichroic exciton chirality method applied to various benzoyl derivatives, the absolute stereostructures of claviridenone-a (1), -b (2), -c (3), and -d (4), which were isolated from the Okinawan soft coral Clavularia viridis, have been elucidated.

Four new prostanoids: Claviridenone-A, -B, -C, and -D from the okinawan soft coral [formula omitted

The structures of four new prostanoids named claviridenone-a, -b, -c, and -d, which were isolated from the Okinawan soft coral Clavularia viridis, were elucidated as 1 , 2 , 3 , and 4 , respectively.