Enzymatic oxidations of alcohols in biosynthesis of bumblebee pheromones

Bachelor thesis Czech RESTRICTED
Bártová, Adéla (2016)
  • Subject: plynová chromatografie; gas chromatography; terpenové alkoholy; terpene alcohols; Bombus terrestris; mass spectrometry; hmotnostní spektrometrie
    mesheuropmc: stomatognathic system

Secretion of cephalic labial gland of Buff-tailed bumblebee males (Bombus terrestris) contains a mixture of terpene alcohols, aliphatic alcohols, esters and alkanes with small amount of aldehydes potentially biosynthetized of (S)-2,3-dihydrofarnesol and geranylcitronellol (major alcoholic compounds). This secretion acts as a marking and luring pheromone during patrolling. This study is focused on oxidation of terpene alcohols using enzymes of cephalic labial gland of a bumblebee. In vitro incubations were accomplished with homogenate of cephalic labial gland and a various substrates: E,E-farnesol, geraniol, 2,3-dihydrofarnesol, hexadecanol. Conditions of incubations and following analysis using gas chromatography were optimized. Two products were detected of farnesol and geraniol incubations, which then later were identified using chemical oxidation with pyridinium-chlorochromate, measurement of NMR specters and MS specters, as two isomers of 2,3-bond. Hexadecanol was not oxidized.
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