M. Iorizzi et al., CHEMICAL AND BIOLOGICAL INVESTIGATION OF THE POLAR CONSTITUENTS OF THE STARFISH LUIDIA-CLATHRATA, COLLECTED IN THE GULF-OF-MEXICO, Journal of natural products, 58(5), 1995, pp. 653-671
Ten new [1-10] and three known [11-13] polyhydroxysteroids were isolat
ed, along with four known asterosaponins [14-17], from the starfish Lu
idia clathrata, collected from the offshore waters of the northern Gul
f of Mexico. The EtOH extracts of this starfish showed feeding-deterre
nt properties against marine fish, and inhibited the settlement of lar
vae of barnacles and bryozoans, as well as the growth of several bacte
ria. The structures of the new compounds were determined by interpreta
tion of their nmr spectral data and by comparison with the spectral da
ta of known compounds. The assignment of the configurations of the sid
e-chain stereogenic centers of compounds 1 and 3-10 were based on the
comparison of their nmr data with those of the stereoisomeric model co
mpounds after derivatization with the chiral auxiliary MTPA reagent. L
arval settlement assays conducted on ten isolated compounds revealed t
hey are all potent inhibitors of settlement. Two of these isolated com
pounds inhibited the growth of several bacteria.