Rusty grain beetle

The biosynthesis of the cucujolides was examined in the merchant grain beetle, O. mercator Fauvel, and the rusty grain beetle, C. ferrugineus (Stephens), using radio- and stable isotope-labeled precursors (Vanderwel et al., 1990,1992b). 

Vanderwel D., Pierce H. D. Jr, Oehlschlager A. C., Borden J. H. and Pierce A. M. (1990) Macrolide (Cucujolide) biosynthesis in the rusty grain beetle, Cryptolestes ferrugineus I. Insect Biochem. 20, 567-572. 

Vanderwel D., Johnston B. and Oehlschlager A. C. (1992b) Cucujolide biosynthesis in the merchant and rusty grain beetles. Insect Biochem. Molec. Biol. 22, 875-883. 

Smith, L.B. (1970) Effects of cold acclimation on supercooling and survival of the rusty grain beetle, Cryptolestes ferrugineus (Stephens) (Coleoptera Cucujidae) at sub-zero temperatures. Canadian Journal of Zoology 48, 853-858. 

Some macrolides are used as aggregation pheromones. Ferralactones I (= cucu-jolide 1,155) and II (156) are 11- and 12-membered ring macrolides, respectively, produced by the rusty grain beetle Cryptolestes ferrugineus [182]. (Z)-3-Dodecen-12-olide (157) and cucujolide HI (158) are 13- and 14-membered ring macrolides, respectively, produced by C. pusillus and C. turcicus, respectively [183,184]. 

Figure 3.38 Macrocyclic lactones from beetle aggregation pheromones. Compound A is found in Cryptolestes pusillus, the flat grain beetle, compounds Band E in C. surinamensis, a mixture of enantiomers of C in C. turcicus, compound D and the R-enantiomer of E in C. ferrugineus, the rusty grain beetle...

The aggregation pheromone of the rusty grain beetle Cryptolestes ferrugineus is a mixture of large ring lactones called cucujolides... 

Rat grain beetle Cryptolestes pusUlus Rusty grain beetle Crystolestes ferrugineus... 

Preparation of (3Z,11/ )-3-dodecen-11-olide (33), the pheromone of the rusty grain beetle. 

Treatment of ( )-hydroxy ester 32 with lipase P (Amano) affected the enantioselective macrolactonization to give the pheromone of the rusty grain beetle (R)-33, although the yield was only 17% (Figure 24.17) [20]. 

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