Cyclization of farnesyl pyrophosphate to the sesquiterpene olefins humulene and caryophyllene by an enzyme system from sage (Salvia officinalis).
A soluble enzyme preparation obtained from sage (Salvia officinalis) leaves was shown to catalyze the divalent metal-ion dependent cyclization of trans, trans-farnesyl pyrophosphate to the macrocyclic sesquiterpene olefins humulene and caryophyllene. The identities of the biosynthetic products were confirmed by radiochromatographic analysis and by preparation of crystalline derivatives, and the specificity of labeling in the cyclization reaction was established by chemical degradation of the olefins derived enzymatically from [1-3H2]farnesyl pyrophosphate. These results constitute the first report on the cyclization of farnesyl pyrophosphate to humulene and caryophyllene, two of the most common sesquiterpenes in nature, and the first description of a soluble sesquiterpene cyclase to be isolated from leaves of a higher plant.
D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D003500:Cyclization; D000081222:Monocyclic Sesquiterpenes; D010944:Plants / Q000201:enzymology*; D000081223:Polycyclic Sesquiterpenes; D011106:Polyisoprenyl Phosphates; D011854:Radiochemistry; D012717:Sesquiterpenes / Q000378:metabolism*; D012995:Solubility
D000081222:Monocyclic Sesquiterpenes; D000081223:Polycyclic Sesquiterpenes; D011106:Polyisoprenyl Phosphates; D012717:Sesquiterpenes; C042686:humulene; C004808:farnesyl pyrophosphate; C024714:caryophyllene