A furofuran that is hexahydrofuro[3,2-b]furan which is substituted at position 2 by a (1E,3E)-4-bromohexa-1,3-dien-1-yl group and at position 5 by a (1R)-3-bromopropadienyl group (the 2R,3aS,5R,6aS diastereoisomer). A natural product first isolated from the red alga Laurencia okamurai Yamada and subsequently found in the sea hare Aplysia kurodai, aplysiallene is an inhibitor of sodium-potassium adenosine triphosphatase.
Stars
This entity has been manually annotated by the ChEBI Team.
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na+/K+-transporting ATPase (EC 3.6.3.9).
Aplysiallene was first isolated from the red alga Laurencia okamurai Yamada by Minoru Suzuki and Etsuro Kurosawa of Hokkaido University, Japan (Phytochemistry, 1985, v24(9), 1999-2002) who determined that the structure included a cis-fused 2,6-dioxabicyclo[3.3.0]octane skeleton containing an (E,E)-bromodiene side-chain and an (R)-bromoallene substituent. The same compound was subsequently isolated from the Japanese sea hare, Aplysia kurodai and named 'aplysiallene' by M. Ojika et al. (Biosci. Biotechnol. Biochem., 2001, v65(2), 474-476) but was misidentified as having only one bromine atom in the molecule, while containing an extra methyl group instead. These errors was corrected in an erratum (M. Ojika et al., Biosci. Biotechnol. Biochem., 2003, v67(2), 460) where the identity of aplysiallene to the compound reported by Suzuki and Kurosawa was confirmed. Subsequently, an elegant total synthesis of aplysiallene by Jian Wang and Brian L. Pagenkopf at the University of Western Ontario (Org. Lett., 2007, v9(18), 3703-3706) resulted in a reassignment of the stereochemistry, affording the structure shown here.