Search results for "Anomala cuprea"

Biosynthesis of scarab beetle pheromones. Enantioselective 8-hydroxylation of fatty acids

1999

Chemical communication in scarab beetles (Coleoptera: Scarabaeidae) is achieved with a wide variety of pheromones, but one typical structure is the γ‐lactone having a long unsaturated hydrocarbon chain. Several species utilize (R,Z)‐5‐(–)‐(oct‐1‐enyl)‐oxacyclopentan‐2‐one (buibuilactone), (R,Z)‐5‐(–)‐(dec‐1‐enyl)‐oxacyclopentan‐2‐one and (S,Z)‐5‐(+)‐(dec‐1‐enyl)‐oxacyclopentan‐2‐one [(R)‐japonilure and (S)‐japonilure]. Using deuterated precursors, we have demonstrated that these compounds are biosynthesized from fatty acids. (9,10‐d4)‐Palmitic acid, (9,10‐d4)‐stearic acid, (9,10‐d2)‐palmitoleic acid, (9,10‐d2)‐oleic acid, (9,10‐d2)‐8‐hydroxypalmitoleic acid and (9,10‐d2)‐8‐hydroxyoleic acid…