Highly polar spiroisoxazolines from the sponge Aplysina fulva.
Two new highly polar brominated spiroisoxazolines, araplysillin N9-sulfamate (1) and an N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxy]-4-aminobutanoic acid (2), were isolated from a sample of Aplysina fulva collected in the Florida Keys. The absolute stereostructures of the new compounds were determined from analysis of MS, 1H and 13C NMR, and CD spectroscopy. Compound 2 provides a structural clue that may unify the biosynthesis of brominated spiroisoxazolines.
Rogers
Evan W
EW
Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
Molinski
Tadeusz F
TF
D000818:Animals; D005431:Florida; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification*; D007555:Isoxazoles / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification*
D006842:Hydrocarbons, Brominated; D007555:Isoxazoles; C522147:N-((5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro(4.5)deca-2,6,8-triene-3-carboxy)-4-aminobutanoic acid; D013141:Spiro Compounds; C522146:araplysillin N9-sulfamate