Open Access
Gyrinidal: A Sesquiterpenoid Aldehyde from the Defensive Glands of Gyrinid Beetles
Author(s) -
Jerrold Meinwald,
Kent E. Opheim,
Thomas Eisner
Publication year - 1972
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.69.5.1208
Subject(s) - sesquiterpene , aldehyde , terpene , stereochemistry , chemistry , biology , organic chemistry , catalysis
Three species of gyrinid beetles (Gyrinus ventralis, Dineutes hornii , andD. serrulatus ) have been found to produce the nor-sesquiterpenoid aldehydegyrinidal in the secretion of their pygidial defensive glands. This highly functionalized terpene is shown to be (E,E,E)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal on the basis of spectral evidence and chemical degradation. While a very wide range of sesquiterpenoid structures occur in nature, gyrinidal appears to be the most highly oxidized acyclic sesquiterpene known.