Chemical and biological investigation of the polar constituents of the starfish Luidia clathrata, collected in the Gulf of Mexico.
Ten new [1-10] and three known [11-13] polyhydroxysteroids were isolated, along with four known asterosaponins [14-17], from the starfish Luidia clathrata, collected from the offshore waters of the northern Gulf of Mexico. The EtOH extracts of this starfish showed feeding-deterrent properties against marine fish, and inhibited the settlement of larvae of barnacles and bryozoans, as well as the growth of several bacteria. The structures of the new compounds were determined by interpretation of their nmr spectral data and by comparison with the spectral data of known compounds. The assignment of the configurations of the side-chain stereogenic centers of compounds 1 and 3-10 were based on the comparison of their nmr data with those of the stereoisomeric model compounds after derivatization with the chiral auxiliary MTPA reagent. Larval settlement assays conducted on ten isolated compounds revealed they are all potent inhibitors of settlement. Two of these isolated compounds inhibited the growth of several bacteria.
Iorizzi
M
M
Università degli Studi del Molise, Facoltà di Agraria, Campobasso, Italy.
Bryan
P
P
McClintock
J
J
Minale
L
L
Palagiano
E
E
Maurelli
S
S
Riccio
R
R
Zollo
F
F
D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D005247:Feeding Behavior / Q000187:drug effects; D006914:Hydroxysteroids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013215:Starfish / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D006914:Hydroxysteroids; D012503:Saponins