Conversion of α-pinene to α-pinene oxide by rat liver and the bark beetle Dendroctonus terebrans microsomal fractions

White, Robert A.; Franklin, Rudolph T.; Agosín, Manuel R.

doi:10.1016/0048-3575(79)90028-2

Cited by 51 publications

(23 citation statements)

References 18 publications

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“…Dendroctonus terebrans a-Pinene metabolized by larvae and adults, but not by pupae, to trans-verbenol (Hughes 1975); a-pinene metabolized by microsomal fraction of larvae and adults to a-pinene oxide (White et al 1979); dose-dependent antennal responses to a-and b-pinene and P. taeda turpentine (Delorme and Payne 1990); turpentine is attractive in the field (reviewed in Nation et al 1996); ethanol synergizes the flight response to turpentine from…”

Section: Species Responses To Selected Monoterpenesmentioning

confidence: 97%

“…White et al (1979) found that microsomes isolated from larval and adult black turpentine beetles, Dendroctonus terebrans (Olivier), converted a-pinene to a-pinene oxide and other oxidation products. Further, they reported that although a-pinene induced cytochrome P450 activity in rat liver microsomes, it did not do so in D. terebrans microsomes.…”

Section: Oxygenated Monoterpenes and Cytochrome P450smentioning

confidence: 99%

“…In the last stages of pheromone biosynthesis, the monoterpene alcohol and ketone pheromone end products in pine bark beetles are likely formed through the catalytic activity of cytochrome P450 enzymes (P450s) (White et al 1979(White et al , 1980Hunt and Smirle 1988). These enzymes may form enantiospecific oxygenated products from prochiral monoterpenes (e.g., myrcene) or from chiral monoterpenes (e.g., a-or b-pinene).…”

Section: Oxygenated Monoterpenes and Cytochrome P450smentioning

confidence: 99%

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Pine monoterpenes and pine bark beetles: a marriage of convenience for defense and chemical communication

et al. 2006

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Pine-feeding bark beetles (Coleoptera: Scolytidae) interact chemically with their host pines (Coniferales: Pinaceae) via the behavioral, physiological, and biochemical effects of one class of isoprenoids, the monoterpenes and their derivatives. Pine monoterpenes occur in the oleoresin and function as behaviorally active kairomones for pine bark beetles and their predators, presenting a classic example of tritrophic chemical communication. The monoterpenes are also essential co-attractants for pine bark beetle aggregation pheromones. Ironically, pine monoterpenes are also toxic physiologically to bark beetles at high vapor concentrations and are considered an important component of the defense of pines. Research over the last 30 years has demonstrated that some bark beetle aggregation pheromones arise through oxygenation of monoterpenes, linking pheromone biosynthesis to the host pines. Over the last 10 years, however, several frequently occurring oxygenated monoterpene pheromone components (e.g., ipsenol, ipsdienol and frontalin) have also been shown to arise through highly regulated de novo pathways in the beetles (reviewed in Seybold and Tittiger, 2003). The most interesting nexus between these insects and their plant hosts involves the latestage reactions in the monoterpenoid biosynthetic pathway, during which isomeric dimethylallyl diphosphate and isopentenyl diphosphate are ultimately elaborated to stereospecific monoterpenes in the trees and to hydroxylated monoterpenes or bicyclic acetals in the insects. There is signal stereospecificity in both production of and response to the monoterpenoid aggregation pheromones of bark beetles and in response to the monoterpenes of the pines. In the California fivespined ips, Ips paraconfusus, we Dedicated to Professor David L. Wood on the occasion of his 75th birthdayÓ Springer Science+Business Media B.V. 2006have discovered a number of cytochome P450 genes that have expression patterns indicating that they may be involved in detoxifying monoterpene secondary metabolites and/or biosynthesizing pheromone components. Both processes result in the production of oxygenated monoterpenes, likely with varying degrees of stereospecificity. A behavioral analysis of the stereospecific response of I. paraconfusus to its pheromone is providing new insights into the development of an efficacious bait for the detection of this polyphagous insect in areas outside the western United States. In contrast, a Eurasian species that has arrived in California, the Mediterranean pine engraver, Orthotomicus (Ips) erosus, utilizes both a monoterpenoid (ipsdienol) and a hemiterpenoid (2-methyl-3-buten-2-ol) in its pheromone blend. The stereospecificity of the response of O. erosus to the monoterpenoid appears to be the key factor to the improved potency of the attractant bait for this invasive species.

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Section: Species Responses To Selected Monoterpenesmentioning

confidence: 97%

Section: Oxygenated Monoterpenes and Cytochrome P450smentioning

confidence: 99%

Section: Oxygenated Monoterpenes and Cytochrome P450smentioning

confidence: 99%

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Pine monoterpenes and pine bark beetles: a marriage of convenience for defense and chemical communication

et al. 2006

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“…A PSMO system from the bark beetle, Dendroctonus terebrans (Olivier) (Coleoptera: Scolytidae), oxidizes a-pinene after induction by a-pinene (White et al, 1979). Pulegone is hydroxylated to 9-hydroxypulegone and 10-hydroxypulegone by microsomes from southern armyworm larvae treated with ~pinene (Brattsten, 1983).…”

Section: Ecological Implicationsmentioning

confidence: 99%

Consequences of Induction of Foreign Compound-Metabolizing Enzymes in Insects

1986

Molecular Aspects of Insect-Plant Associations

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“…That MFO is involved in the oxidation of monoterpenes was reported by White et al (1979), who showed that o~-pinene was oxidized to c~-pinene epoxide by cytochrome P-450-dependent monooxygenases prepared from bark beetles.…”

Section: Discussionmentioning

confidence: 99%

Microsomal oxidation of allelochemicals in generalist (Spodoptera frugiperda) and semispecialist (Anticarsia gemmatalis) insect

1987

J Chem Ecol

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Midgut microsomes prepared from larvae of the fall armyworm [Spodoptera frugiperda (J.E Smith)], a generalist insect, and the velvetbean caterpillar (Anticarsia gemmatalis Hubner), a semispecialist, were used to study their oxidative activity toward a variety of allelochemicals. Allelochemicals such as terpenoids, alkaloids, indoles, glucosinolates, flavonoids, coumarins, cardenolides, phenylpropenes, and a ketohydrocarbon were all metabolized by the microsomal cytochrome P-450 monooxygenases in both species. Fall armyworm microsomes oxidized monoterpenes more favorably than other types of terpenes, indicating a preference for these compounds. In all instances, the oxidative metabolism of these allelochemicals can be induced by dietary allelochemicals such as indole 3-carbinol, indole 3-acetonitrile, menthol, flavone, or peppermint oil ranging from 1.3- to 9.5-fold. In the case of certain triterpenes, tetraterpene, alkaloid, coumarin, and cardenolides, metabolic activity can only be observed after induction. The monooxygenase activities toward these allelochemicals were generally higher in the generalist than in the semispecialist. These findings provide strong evidence that microsomal monooxygenases play an important role in the detoxification of plant toxins and hence host-plant selections in herbivorous insects.

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Conversion of α-pinene to α-pinene oxide by rat liver and the bark beetle Dendroctonus terebrans microsomal fractions

Cited by 51 publications

References 18 publications

Pine monoterpenes and pine bark beetles: a marriage of convenience for defense and chemical communication

Pine monoterpenes and pine bark beetles: a marriage of convenience for defense and chemical communication

Consequences of Induction of Foreign Compound-Metabolizing Enzymes in Insects

Microsomal oxidation of allelochemicals in generalist (Spodoptera frugiperda) and semispecialist (Anticarsia gemmatalis) insect

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