Isoprenoid biosynthesis in aseptic larvae of Calliphora erythrocephala

Beedle, Alan S.; Walton, Michael; Goodwin, T. W.

doi:10.1016/0020-1790(75)90057-8

Cited by 17 publications

(8 citation statements)

References 19 publications

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“…It is likely that insects possess the enzymes that catalyze the reactions in the isoprenoid pathway necessary for the synthesis of ubiquitous terpenoids such as JH (30) and respiratory chain cofactors such as ubiqinone (31). A variety of insects appear to produce very specific isoprenoids, such as geranyl acetate and various isomers of farnesene, as behavioral chemicals (32)(33)(34).…”

Section: Discussionmentioning

confidence: 99%

De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera: Scolytidae).

Seybold

Quilici²,

Tillman³

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

124

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The California five-spined ips, Ips paraconfusus Lanier, produces the myrcene-derived acyclic monoterpene alcohols ipsenol (2-methyl-6-methylene-7-octen-4-ol) and ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) as components of its aggregation pheromone. The pine engraver beetle, Ipspini (Say), produces only ipsdienol. Previous studies have shown that myrcene, a monoterpene in the pines colonized by these beetles, is a direct precursor to these pheromone components. In vivo radiolabeling studies reported hereshowed that male I. paraconjifsus incorporated [1_14C]acetate into ipsenol, ipsdienol, and amitinol (trans-2-methyl-6-methylene-3,7-octadien-2-ol), while male I. pini incorporated [1-_4C]acetate into ipsdienol and amitinol. Females of these species produced neither labeled nor unlabeled pheromone components. The purified radiolabeled monoterpene alcohols from males were identified by comparison of their HPLC and GC retention times with those of unlabeled standards. HPLCpurified fractions containing the individual radiolabeled components were analyzed by GC-MS and were shown to include only the pure alcohols. To further confirm that ipsdienol and ipsenol were radiolabeled, diastereomeric ester derivatives of the isolated alcohols were synthesized and analyzed by HPLC and GC-MS. After derivatization of the radiolabeled alcohols, the HPLC analysis demonstrated expected shifts in retention times with conservation of naturally occurring stereochemistry. The results provide direct evidence for de novo biosynthesis of ipsenol, ipsdienol, and amitinol by bark beetles. The aggregation pheromone components (4S)-(-)-ipsenol(2-methyl-6-methylene-7-octen-4-ol) (1) and (4S)-( + )-ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) (2) were isolated and identified from males of the California five-spined ips, Ips paraconfusus Lanier. These components, together with (1S,2S)-(+)-cis-verbenol (cis-4,6,6-trimethyl bicyclo[3.1.1]-hept-3-en-2-ol), were identified as the first coleopteran pheromone (1). The structural similarity of the acyclic monoterpene alcohols ipsenol and ipsdienol to myrcene (2, 3), a monoterpene present in the oleoresin of the principal host, ponderosa pine, Pinus ponderosa Laws., led to a deuterium labeling study with I. paraconfusus that unequivocally showed the in vivo transformation of myrcene to ipsenol and ipsdienol (4). A more recent labeling study demonstrated the conversion of myrcene to ipsdienol in the male pine engraver beetle, Ips pini (Say) (5). Recent reviews (6-9) emphasize the central role of plant-derived myrcene in the production of ipsenol and ipsdienol, including the hypothesis that myrcene from the host may be sequestered and bioaccumulated by males during early developmental stages for later use as adults (9 consistent with the general concept that monoterpenes sensu stricto are plant products (7,10,11).However, it has been recognized that alternative routes for Ips spp. pheromone biosynthesis may exist, such as de novo biosynthesis or utilization of other terpene hydrocarbo...

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Section: Discussionmentioning

confidence: 99%

De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera: Scolytidae).

Seybold

Quilici²,

Tillman³

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

124

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“…Calliphora eggs have been shown [22] to synthesize [14C] dolichol by incubating them with DL-[2AaC] mevalonic acid lactone. Insect and other eucaryotic polyprenols biosynthesis would be similar to that of bacterial undecaprenols [9].…”

Section: Discussionmentioning

confidence: 99%

Phosphorylation of dolichol by insect enzymes

Allué¹

1979

FEBS Letters

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“…There appears to be some requirement for the participation of polyprenoid intermediates in invertebrate cell-glycosylation reactions, since dolichol (Beedle et al, 1975), dolichol phos-phate (Quesada et al, 1975) and dolichol phosphomannose (Quesada et al, 1976) have been identified unequivocally in larval extracts. Additional evidence for dolichol pyrophosphatelinked oligosaccharides has also been obtained for the fruit-fly Ceratitis capitata larvae (Quesada & Belocopitow, 1978), although a precursor-product relationship between lipid intermediates and cellular glycoproteins has yet to be shown.…”

Section: Polyprenoid Intermediatesmentioning

confidence: 99%

Effects of tunicamycin on insect cells

Butters¹,

Hughes²

1980

Biochemical Society Transactions

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Conclusions Use of the drug tunicamycin has greatly facilitated study of many different aspects of immunoglobulin biosynthesis. The most striking conclusion is that blocking glycosylation does not prevent synthesis of immunoglobulin heavy chains either directly or by feedback; non-glycosylated heavy chains are able to assemble into immunoglobulin molecules capable of being secreted. Since glycosylation affects overall protein threedimensional structure, differences in the structure of nonglycosylated immunoglobulins might be responsible for the failure of non-glycosylated IgM to be transferred to the cell surface, alterations in the details of assembly and secretion of the non-glycosylated immunoglobulins. Such changes in structure in the non-glycosylated molecules might also affect function, and studies on the function of non-glycosylated antibodies should prove rewarding. We thank Dr. W. F. J. Cuthbertson (Glaxo-Allenburys Research) and Robert L. Hamill (Lilly Research) for kindly providing gifts of tunicamycin.

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Isoprenoid biosynthesis in aseptic larvae of Calliphora erythrocephala

Cited by 17 publications

References 19 publications

De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera: Scolytidae).

De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera: Scolytidae).

Phosphorylation of dolichol by insect enzymes

Effects of tunicamycin on insect cells

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