Production of verbenol pheromone by a bacterium isolated from bark beetles

Semiochemicals in the Natural History of Southern Pine Beetle Dendroctonus frontalis Zimmermann and Their Role in Pest Management

“…Verbenone (and verbenol) can be generated through autoxidation of host-released α-pinene coming into contact with atmospheric oxygen (Hunt et al, 1989;Moore et al, 1956). Microbes including bark beetle symbionts and incidental associates are also capable of oxidizing α-pinene to verbenol and/or verbenol to verbenone Brand et al, 1975;Hunt and Borden, 1990;Xu et al, 2015). A fungus carried in the mycangium of female D. frontalis (Ceratocystiopsis ranaculosus J.R. Bridges and T.J. Perry) was shown to convert verbenol to verbenone (Brand et al, 1976).…”

Host-Tree Chemistry Affecting Colonization in Bark Beetles

“…However, verbenone (and possibly trans-verbenol) are also produced increasingly in aging logs infested by bark beetles (Birgersson and Bergstrom, 1989;. A common bacterium, Bacillus cereus, also isolated from I. paraconfusus can make cisand trans-verbenol from a-pinene (Brand et al, 1975). Several yeasts from I. typographus can interconvert the verbenols, and when grown in a phloem medium they produced the oxygenated monoterpenes a-terpineol, borneol, myrtenol, terpenene-4-01, and trans-pinocarveol, compounds also shown to be released increasingly from bark beetle holes with age of attack (Leufvtn et al, 1984(Leufvtn et al, , 1988Birgersson and Bergstrom, 1989).…”

“…Verbenone inhibits the attraction of these beetles to their respective aggregation pheromones Vit6, 1969, 1970;Byers and Wood, 1980;Bakke, 198 1;Byers et al, 1989c;Byers, 1993a). Some microorganisms isolated from bark beetles or their gallery walls may convert a-pinene to cis-and trans-verbenol (Bacillus cereus) (Brand et al, 1975), or trans-verbenol to verbenone (various yeasts) (Leufvkn et al, 1984). A fungal culture isolated from the mycangium of D. frontalis was able to convert trans-verbenol to verbenone, and it was proposed that this process may account for termination of attack (Brand et al, 1976).…”

Pheromone biosynthesis in the bark beetle, Ips paraconfusus, during feeding or exposure to vapours of host plant precursors

“…The relationship between the concentration of myrcene in vapour phase and subsequent ipsenol and ipsdienol production was quantified by BYERS et al (1979). Bacillus cereus isolated from the hindgut of I. paraconfius converted racemic a-pinene to cis-verbenol and trans-verbenol in vitro ( BRAND et al, 1975). RENWCK et al (1976a) using NMR, IR and GC-MS methods reported that both sexes produced cis-verbenol when exposed to the vapour of (-)-a-pinene and produced trans-verbenol when exposed to the (+) enantiomer.…”