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

A polyoxygenated and halogenated labdane, spongianol ( 1 ); a polyoxygenated steroid, 3β,5α,9α-trihydroxy-24 S -ethylcholest-7-en-6-one ( 2 ); a rare seven-membered lactone B ring, (22 E ,24 S )-ergosta-7,22-dien-3β,5α-diol-6,5-olide ( 3 ); and an α,β-unsaturated fatty acid, ( Z )-3-methyl-9-oxodec-2-enoic acid ( 4 ) as well as five known compounds, 10-hydroxykahukuene B ( 5 ), pacifenol ( 6 ), dysidamide ( 7 ), 7,7,7-trichloro-3-hydroxy-2,2,6-trimethyl-4-(4,4,4-trichloro-3-methyl-1-oxobu-tylamino)-heptanoic acid methyl ester ( 8 ), and the primary metabolite 2'-deoxynucleoside thymidine ( 9 ), have been isolated from the Red Sea sponge Spongia sp. The stereoisomer of 3 was discovered in Ganoderma resinaceum , and metabolites 5 and 6 , isolated previously from red algae, were characterized unprecedentedly in the sponge. Compounds 7 and 8 have not been found before in the genus Spongia . Compounds 1 - 9 were also assayed for cytotoxicity as well as antibacterial and anti-inflammatory activities.