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  • plant-insect interactions  (4)
  • catalpol  (3)
  • 1-(3,4,5-trimethoxyphenyl)-2-(4-allyl-2,6-dimethoxy)propane  (1)
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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 14 (1988), S. 435-441 
    ISSN: 1573-1561
    Keywords: Meris alticola ; Neoterpes graefiaria ; Lepidoptera ; Geometridae ; Penstemon virgatus ; Penstemon barbatus ; Scrophulariaceae ; iridoid glycosides ; catalpol ; Müllerian mimicry ; sequestration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The iridoid glycoside catalpol was found to be sequestered by larvae ofMeris alticola feeding onPenstemon virgatus and by larvae ofNeoterpes graefiaria which utilizeP. barbatus. The strikingly similar larval patterns of these two ennomine geometrids were previously considered to be disruptive, but predator-based Mullerian mimicry is equally likely to be involved. The cryptic adult moths generally contain only small amounts of catalpol, having left most of the bitter iridoid in the pupal case and in the meconium excreted after eclosion. OneNeoterpes female did contain considerable catalpol in the abdomen, presumably in the eggs.
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  • 2
    ISSN: 1573-1561
    Keywords: Euphydryas anicia ; Lepidoptera ; Nymphalidae ; Besseya plantaginea ; Scrophulariaceae ; iridoid glycosides ; sequestration ; plant-insect interactions ; herbivory
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The checkerspot butterfly,Euphydryas anicia, utilizes mainlyBesseya plantaginea and only occasionallyCastilleja integra as a larval hostplant at Michigan Hill, a few kilometers from a site whereC. integra is used by over 90% of the butterflies. TheB. plantaginea leaves that are consumed contain 9–22% iridoid glycosides, composed mainly of catalpol and catalpol esters, while larvae from the same plants contain 6–18% iridoids, mainly catalpol and no esters. Field-collected adult butterflies contain 0.5–4.3% iridoids. Laboratory-reared adults secrete iridoids in the meconium upon eclosion and retain similar amounts. The adult and meconium iridoid content is considerably lower than in the larvae, and metabolism in the pupal stage may be occurring.
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  • 3
    ISSN: 1573-1561
    Keywords: Castilleja ; Scrophulariaceae ; Senecio ; Asteraceae ; Lupinus ; Leguminosae ; hemiparasites ; alkaloids ; plant-insect interactions
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Castilleja (Scrophulariaceae) species of the western United States contain pyrrolizidine and quinolizidine alkaloids. TheCastilleja obtain the alkaloids by root parasitism on host plants, withSenecio atratus andS. triangularis (Asteraceae) furnishing the pyrrolizidines, and quinolizidines being obtained fromLupinus species andThermopsis montana (Leguminosae). Individual plants within a givenCastilleja species population may be devoid of alkaloids while others have high alkaloid content. No populations have been found which are made up of both pyrrolizidine- and quinolizidine-containing individuals. These results have important implications forCastilleja ecology, for the study of insect herbivores which areCastilleja specialists, and in the development of systems for the investigation of the role of alkaloids as plant defenses.
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  • 4
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 14 (1988), S. 2147-2168 
    ISSN: 1573-1561
    Keywords: Euphydryas anicia ; Lepidoptera ; Nymphalidae ; Castilleja integra ; Besseya plantaginea ; Besseya alpina ; Scrophulariaceae ; iridoid glycosides ; sequestration ; metabolism ; plant-insect interactions ; herbivory
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The iridoid glycoside content of individual adultEuphydryas anicia butterflies from two Colorado populations was quantitatively determined. At one site (Red Hill), larval host plants wereCastilleja integra andBesseya plantaginea, while at the other site (Cumberland Pass) a single host plant,B. alpina, was used. At Red Hill, macfadienoside and catalpol were sequestered, while at Cumberland Pass, catalpol and aucubin were sequestered. Artificial diet studies showed that larvae hydrolyzed a major iridoid ofB. plantaginea, 6-isovanilIylcatalpol, to catalpol (which was sequestered) and isovanillic acid (which was excreted). Large year-to-year and individual variation in butterfly iridoid content was established as was a female-male difference in macfadienoside vs. catalpol content. Larval host plant distributions and numbers were determined at Red Hill for two years and compared with changes in butterfly populations and sequestered iridoids.
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  • 5
    ISSN: 1573-1561
    Keywords: Lymantria dispar ; Lepidoptera ; Lymantriidae ; Liriodendron tulipifera ; Acer rubrum ; Cornus florida ; gypsy moth ; alkaloids ; N-methyl-crotsparine ; 1-(3,4,5-trimethoxyphenyl)-2-(4-allyl-2,6-dimethoxy)propane ; bisphenylpropanoid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Early theories on plant chemical defense against herbivory emphasized that apparent and unapparent plants were primarily defended by different types of compounds. More and more evidence suggests that both quantitative and qualitative defenses are found in apparent plants and that they can play a defensive role against herbivores. A survey of the literature on the gypsy moth suggests not only that there is a large variety of qualitative compounds, as well as the expected quantitative ones, but that unfavored hosts of the gypsy moth are associated with the presence of alkaloids. Foliage of three tree species,Liriodendron tulipifera L.,Acer rubrum L., andCornus florida L., was examined to confirm the presence of alkaloids and other major secondary metabolites. The known sesquiterpene lactone, lipiferolide, and the sugar derivative, liriodendritol, were components ofL. tulipifera leaves, along with a bisphenylpropanoid previously found only in nutmeg. Alkaloid content [i.e., (−)-N-methylcrotsparine content] was low and leaves tested positive for HCN. Leaves ofA. rubrum L. were examined for the presence of gramme, but none could be detected. No alkaloids were detected inCornus florida.
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  • 6
    ISSN: 1573-1561
    Keywords: Poladryas minuta ; Lepidoptera ; Nymphalidae ; checkerspot ; Penstemon virgatus ; Penstemon secundiflorus ; Scrophulariaceae ; iridoid glycosides ; catalpol ; sequestration ; metabolism ; herbivory
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A bivoltine checkerspot butterfly,Poladryas minuta, is aPenstemon specialist, not known to utilize any other plant genus for oviposition and larval feeding. At several intermontane plains sites of central Colorado, the butterfly utilizesPenstemon virgatus as its sole host plant. Analysis of the host plant showed it to contain three cinnamyl-type catalpol esters (scutellarioside-II, globularin, globularicisin) and catalpol. The host plant contained an average of 10% dry weight iridoids, but some variation among individual plants and leaves within plants was noted. Field-collected butterflies contained 2.1–8.7% dry weight catalpol, but no other iridoids. Adults from larvae fedP. virgatus in the lab contained 4.2–9.0% dry weight catalpol and excreted large amounts of catalpol in the meconium. No catalpol was found in the larval frass. Larvae did not consume three alternate iridoid-containing host-plant species, and most eventually died rather than feed on the alternate plants. Larvae did consume small amounts of artificial diets containing the alternate species andP. virgatus, but most went into diapause and some died. Survival was good on artificial diet containing 10% dry weight of the iridoid esters fromP. virgatus. Only catalpol was found in pupae and adults, but it was absent from the larval frass. The cinnamic-type acids expected from larval hydrolysis of the esters were not found in larval frass, pupae, or adults. These results are contrasted with those found for another checkerspot,Euphydryas anicia, which consumes a different host-plant species but was present at one of the same sites withPoladryas minuta.
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  • 7
    ISSN: 1573-1561
    Keywords: Euphydryas anicia ; Lepidoptera ; Nymphalidae ; Castilleja integra ; Besseya plantaginea ; Besseya alpina ; iridoid glycosides ; catalpol ; macfadienoside ; sequestration ; plant-insect interactions ; herbivory ; ecological chemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Iridoid glycosides were found to be sequestered by natural populations ofEuphydryas anicia after ingestion from the host plantsBesseya alpina, B. plantaginea, andCastilleja integra. Both major iridoids ofB. alpina, cataipol and aucubin, were found in butterfly populations where this was the only host plant. The catalpol-aucubin ratio was higher in the butterflies than in the host plant. AnE. anicia population which uses bothB. plantaginea andC. integra as host plants was found to sequester cataipol as well as another iridoid, macfadienoside. Macfadienoside was the major iridoid ofC. integra, while catalpol esters were the major iridoids ofB. plantaginea. Although it was a major sequestered iridoid, catalpol was a minor constituent in both host plants. The macfadienoside-catalpol ratio in the butterflies from this population was highly variable, and there appeared to be both sex and individual variation in host plant and/or iridoid glucoside utilization byE. anicia. Although other iridoids were present in the host plants, none was sequestered in more than trace amounts.
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