Sinularia flexibilis

Maida, M., Carroll, A. R., and Coll, J. C., Variability of terpene content in the soft coral Sinularia flexibilis (Coelenterata Octocorallia), and its ecological implications, J. Chem. Ecol., 19, 2285, 1993. 

A number of cembranoid diterpenoids have been isolated from corals. These include (128) from a South Pacific soft coral/ trocheliophorol (129) from Sarcophyton trocheliophorium, " flexibilide (=sinularin) (130) from Sinularia flexibilis, and isosarcophytoxide (131) and the corresponding diepoxide from a Sarcophyton species.A norcembrane (132) has been isolated from Sinularia... 

There have been very few examples of 5,6-dihydro-a-pyrones isolated from the marine environment. In 1992, Hamada et al. obtained lobatrienolide (18) from an Okinawan soft coral Sinularia flexibilis (25). The structure of lobatrienolide was established by spectral techniques and confirmed by photo-oxidation of lobatriene (19), isolated from the same soft coral collection, to (18). The structure of (19) was proved as follows Scheme 1). Lithium-ethylamine reduction of (19) produced the diol (20) which on ozonolysis, MCPBA oxidation to the acetate (21) and hydrolysis gave the alcohol (22). The 5-stereochemistry of the alcoholic group in (22) was determined by the modified Mosher method 24), which together with NMR correlations in lobatriene, afforded the complete stereochemistry of (19) and hence also that of lobatrienolide... 

Hamada, T., T. Kusumi, M.O. Ishttsuka, and H. Kakisawa Stmctures and Absolute Configurations of New Lobane Diterpenoids from the Okinawan Soft Coral Sinularia flexibilis. Chem. Letters, 33 (1992). 

SPECTRAL data UV, IR, PMR, Mass Spec organism Sinularia flexibilis (Coelenterata) reference 178... 

Spermidine derivatives are known to have cytotoxic properties. Kazlauskas et al. 387) isolated two new N-methylated amides (742) and (743) from a species of Sinularia after the methanol extract had shown potent in vitro and in vivo activity against a human pathogenic bacterium Pseudomonas aeruginosa. The amides 742 and 743 which accounted for the antimicrobial activity were toxic and therefore unlikely to be of value as antibiotics. Some efforts have been made toward the synthesis of such spermidine derivatives derived from corals 387, 497). Three amides (744-746) different from those mentioned earher and derived from tyramine, have been reported as metabolites from Sinularia flexibilis 498). Structures of 744, 745, and 746 were deduced spectroscopically and that of 744 has been confirmed by synthesis. The amides (744-746) accounted for the cardiotonic activity which has been observed for the crude dichloromethane extract of S. flexibilis. 

Mori, K., S. Suzuki, K. Iguchi, and Y. Yamada 8,11-Epoxy Bridged Cembranolide Diterpene from the Soft Coral Sinularia flexibilis. Chem. Lett. 1983,1515. 

Kazlauskas, R., J.F. Marwood, and R.J. Wells 2-Phenylethylamides of a Novel Lipid Acid Atrial Stimulants from the Soft Coral Sinularia flexibilis. Aust. J. Chem. 33,1799 (1980). 

Figure 1.8. Left Sinularia flexibilis coral (above center) inhibiting the growth of neighboring hard corai Pavona cactus (below) along a gradient of distance between the two (photo S. La Barre). Right Longitudinal sedion of coral ("Stylophora pistillataj and its characteristic chemical imprint (photo F. Mohamadi)...

Sinularia flexibilis and Lohophytum hedleyi Diterpenoids Elexibilide dihydroflexibilide eudesmanoid m Necrosis on tissues of Acropora formosa and Porites cylindrica [91]... 

Kazlauskas, R., Murphy, P.T., Wells, R.J., Schonholzer, P and Coll, (. C. (1978) Cembranoid constituents from an Australian collection of ftie soft coral Sinularia flexibilis. Aust.J. Chem., 31,1817-1824. 

Chen, B.-W, Chao, C.-H., Su, J.-H., Huang, C.-Y, Dai, C.-F., Wen, Z.-H., and Sheu, J.-H. (2010a) A novel symmetric suIfursoft coral Sinularia flexibilis. Tetrahedron Lett., 51,5764-5766. 

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