Open AccessBrasilenyne and cis -dihydrorhodophytin: Antifeedant medium-ring haloethers from a sea hare ( Aplysia brasiliana )
Author(s) -
Robin B. Kinnel,
R. Karl Dieter,
Jerrold Meinwald,
D. Van Engen,
Jon Clardy,
Thomas Eisner,
Martha O. Stallard,
William Fenical
Publication year - 1979
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.76.8.3576
Subject(s) - aplysia , ring (chemistry) , stereochemistry , congener , chemistry , biology , organic chemistry , evolutionary biology
Two straight-chain C15 fish antifeedants have been isolated from the sea hareAplysia brasiliana . Chemical, spectral, and x-ray diffraction studies led to the characterization of these medium-ring ethers as brasilenyne (2) andcis -dihydrorhodophytin (3). The oxonin ring system of 2 is novel in nature. Biosynthetic considerations permit the postulation that a third compound, a noncrystalline congener of these compounds, iscis -isodihydrohodophytin (4).