Eucalyptus oils in the defensive oral discharge of Australian sawfly larvae (Hymenoptera: Pergidae)

Morrow, P. A.; Bellas, T. E.; Eisner, Thomas

doi:10.1007/bf00345473

Cited by 73 publications

(33 citation statements)

References 11 publications

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“…The role of cineole 1 is somewhat unclear, although it is believed to be involved in a number of functions including defense against herbivores (11,12) and pathogens (13), attracting pollinators and fruit-dispersing animals (14), and/or as an allelopathic agent (15,16). The Australian eucalypt population collectively produces and releases an estimated 500,000 tons of cineole 1 into the environment annually (17).…”

mentioning

confidence: 99%

Cytochrome P450cin (CYP176A), Isolation, Expression, and Characterization

Hawkes¹,

Adams²,

Burlingame³

et al. 2002

Journal of Biological Chemistry

112

131

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Cytochromes P450 are members of a superfamily of hemoproteins involved in the oxidative metabolism of various physiologic and xenobiotic compounds in eukaryotes and prokaryotes. Studies on bacterial P450s, particularly those involved in monoterpene oxidation, have provided an integral contribution to our understanding of these proteins, away from the problems encountered with eukaryotic forms. We report here a novel cytochrome P450 (P450 cin , CYP176A1) purified from a strain of Citrobacter braakii that is capable of using cineole 1 as its sole source of carbon and energy. This enzyme has been purified to homogeneity and the amino acid sequences of three tryptic peptides determined. By using this information, a PCR-based cloning strategy was developed that allowed the isolation of a 4-kb DNA fragment containing the cytochrome P450 cin gene (cinA). Sequencing revealed three open reading frames that were identified on the basis of sequence homology as a cytochrome P450, an NADPH-dependent flavodoxin/ferrodoxin reductase, and a flavodoxin. This arrangement suggests that P450 cin may be the first isolated P450 to use a flavodoxin as its natural redox partner. Sequencing also identified the unprecedented substitution of a highly conserved, catalytically important active site threonine with an asparagine residue. The P450 gene was subcloned and heterologously expressed in Escherichia coli at ϳ2000 nmol/liter of original culture, and purification was achieved by standard protocols. Postulating the native E. coli flavodoxin/flavodoxin reductase system might mimic the natural redox partners of P450 cin , it was expressed in E. coli in the presence of cineole 1. A product was formed in vivo that was tentatively identified by gas chromatography-mass spectrometry as 2-hydroxycineole 2. Examination of P450 cin by UV-visible spectroscopy revealed typical spectra characteristic of P450s, a high affinity for cineole 1 (K D ‫؍‬ 0.7 M), and a large spin state change of the heme iron associated with binding of cineole 1. These facts support the hypothesis that cineole 1 is the natural substrate for this enzyme and that P450 cin catalyzes the initial monooxygenation of cineole 1 biodegradation. This constitutes the first characterization of an enzyme involved in this pathway.The cytochrome P450s (P450s) 1 are a superfamily of oxidative hemoproteins (1, 2) that carry out an enormous variety of oxidative transformations. These range from simple alkene epoxidation and heteroatom oxidation all the way through oxygen insertion into unactivated C-H bonds and C-C bond cleavage (3). P450s are broadly categorized as either soluble, e.g. most bacterial P450s, or as membrane bound/microsomal monooxygenases, e.g. most eukaryotic P450s. All P450s, however, contain a prosthetic heme group that is ligated to the protein backbone by a cysteinyl sulfur coordinated to the heme iron. It is this heme-thiolate moiety that is responsible for much of the chemistry carried out by these enzymes. The typical reaction catalyzed by a P450 is given by Reaction...

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mentioning

confidence: 99%

Cytochrome P450cin (CYP176A), Isolation, Expression, and Characterization

Hawkes¹,

Adams²,

Burlingame³

et al. 2002

Journal of Biological Chemistry

112

131

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“…Orb-weaving spiders, for instance, may shield themselves from the defensive chemical discharges of insect prey by encasing the latter in silk (17), while grasshopper mice subdue chemically protected beetles by first causing these to discharge their spray into the soil (18). Herbivores also may possess strategies for bypassing the defenses ofplants (19)(20)(21)(22). Ant lions are among the most successful of ant predators, and Formicinae are a dominant group of ants.…”

Section: Discussionmentioning

confidence: 99%

Circumvention of prey defense by a predator: ant lion vs. ant.

Eisner

Baldwin

Conner

1993

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

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The pit-dwelling ant lion Myrmeleon carolinus, although topically sensitive to formic acid, is able to prey on formic acid-spraying ants (Camponotus floridanus). It kills the ants without inducing them to spray, and it sucks out the ant's body contents without puncturing the acid sac. Ordinarily, when Camponotus is attacked it retaliates by simultaneously biting and spraying, but it usually refrains from spraying until it has secured a grip with the mandibles. When Myrmeleon pulls Camponotus into the sand at the bottom of the pit, the ant is seemingly unable to grasp the ant lion and it is killed without being induced to spray. When feeding on the ant, the ant lion sucks up the contents of the nutrient-laden crop. How the ant lion differentiates between crop and acid sac, managing to spare the latter while rupturing the former, remains unknown.

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“…Eucalyptus paucifl ora is listed on the label as the host plant for the male paratype from NSW. Morrow et al (1976) collected four species of Perginae (Pergidae), representing four diff erent genera, from this plant host at this locality. It is unclear from the label data whether this specimen was reared or simply collected from this plant, but no parasitoid rearings were indicated in Morrow et al (1976).…”

Section: Pergaphaga Leaskimentioning

confidence: 99%

A revision of the westwoodiine genus Pergaphaga (Hymenoptera, Ichneumonidae, Ctenopelmatinae)

Wharton¹,

Cammack²,

Mullins³

2010

785

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Pergaphaga Gauld, a genus of ctenopelmatine Ichneumonidae endemic to Australia, is revised. Th e only previously described species, Pergaphaga nigra Gauld, is redescribed. Th ree additional species are newly described: Pergaphaga iangauldi Cammack & Wharton, sp. n. from New South Wales, ACT, and Victoria, P. leaski Wharton, sp. n. from Victoria, and P. xanthops Wharton, sp. n. from New South Wales and ACT. Keys to species and a phylogenetic analysis are presented. Morphological terms are linked to the Hymenoptera Anatomy Ontology.

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Eucalyptus oils in the defensive oral discharge of Australian sawfly larvae (Hymenoptera: Pergidae)

Cited by 73 publications

References 11 publications

Cytochrome P450cin (CYP176A), Isolation, Expression, and Characterization

Cytochrome P450cin (CYP176A), Isolation, Expression, and Characterization

Circumvention of prey defense by a predator: ant lion vs. ant.

A revision of the westwoodiine genus Pergaphaga (Hymenoptera, Ichneumonidae, Ctenopelmatinae)

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