Terpenoid metabolites from skin extracts of the dendronotid nudibranch Tochuinatetraquetra

Abstract
The skin chemistry of specimens of the dendronotid nudibranch Tochuinatetraquetra collected at Port Hardy and Bamfield, British Columbia, has been examined. Port Hardy animals yielded tochuinyl acetate (1) and dihydrotochuinyl acetate (2), two new cuparane sesquiterpenoids, as well as rubifolide (3) and pukalide (4), two previously known cembrane diterpenoids. Bamfield animals yielded the known briarein-type diterpenoid ptilosarcenone (5) and the previously unreported butanoate analogue 6. The T. tetraquetra metabolites are sequestered from coelenterates in the nudibranch's diet.