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  • 1
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of natural products 50 (1987), S. 485-489 
    ISSN: 1520-6025
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1520-5118
    Source: ACS Legacy Archives
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Process Engineering, Biotechnology, Nutrition Technology
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of natural products 49 (1986), S. 680-683 
    ISSN: 1520-6025
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of natural products 54 (1991), S. 626-628 
    ISSN: 1520-6025
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 1573-1561
    Keywords: Plant toxins ; palatability ; diterpenoid alkaloids ; methyllycaconitine ; Delphinium spp
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Tall larkspur (Delphinium spp.) is a serious toxic plant problem on western U.S. ranges. The major toxins in tall larkspur are methyllycaconitine (MLA) and 14-deacetylnudicauline (14-DAN); the sum of both is termed the toxic alkaloid concentration. Toxic alkaloids comprise about 20–50% of the total alkaloid concentration in tall larkspur. Toxic and total alkaloid concentration generally declines with maturity, whereas cattle and sheep consumption of larkspur typically increases with plant maturity. We hypothesized that cattle and sheep consumption of tall larkspur was negatively related to higher concentrations of total or toxic alkaloid. We compared consumption of several collections of dried, ground larkspur and fresh larkspur in a series of trials. In another trial, a crude alkaloid fraction was extracted with ethanol, added to alfalfa hay, and consumption compared to untreated alfalfa hay, alcohol-treated hay, and the essentially alkaloid-free plant residue. In all cases we correlated amounts eaten with total and toxic alkaloid concentration. A grazing trial was also conducted to relate larkspur consumption over time to alkaloid concentrations. Total alkaloid concentrations in dried, whole-plant collections ranged from 9.3 to 38.8 mg/g of dry weight, whereas toxic alkaloid concentrations varied from 0.0 to 7.1 mg/g. In one pen trial, cattle preferred a larkspur collection (P〈0.01) that contained no toxic alkaloids but had a high total alkaloid concentration (39 mg/g). There was no correlation (P〉0.05), however, between concentrations of total or toxic alkaloids and amount of dry plant consumed in this or any other trial. Conversely, sheep consumption tended to be negatively influenced by total and toxic alkaloid concentration (P≤0.08). In the trials with extract, cattle preferred the alcohol-treated hay and rejected the alkaloid-free residue (P〈0.01), whereas the alkaloid-treated hay was of intermediate acceptability. Cattle preferred the alkaloid-treated hay over the alkaloid-free residue, indicating that alkaloids did not deter consumption. Conversely, the alkaloid-treated hay was less preferred than either untreated or alcohol-treated hay, suggesting a negative effect on acceptability. There was no correlation between alkaloid concentration and amount of treated feed eaten. In field trials, the amount of composited, fresh leaves or flowers eaten by cattle was influenced by plant part (P=0.04), but was not related (P〉0.05) to alkaloid concentration. Cattle preferred leaves over flowers when offered individual plants differing in phenological stage and/or amount of shade, but alkaloid concentration was not related to consumption. We conclude that knowledge of the concentration of total or toxic alkaloid in tall larkspur will give little or no indication of plant acceptability to cattle. Even though accurate predictions can be made about the potential toxicity of larkspur based on the concentration of toxic alkaloids, predictions about consumption must be based primarily on plant phenology.
    Type of Medium: Electronic Resource
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  • 6
    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.
    Type of Medium: Electronic Resource
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  • 7
    ISSN: 1573-1561
    Keywords: Thessalia leanira fulvia ; Chlosyne leanira fulvia ; Lepidoptera ; Nymphalidae ; Castilleja integra ; Scrophulariaceae ; iridoid glycosides ; sequestration ; herbivory
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A small population of a polyvoltine checkerspot butterfly,Thessalia leanira fulvia (also known asChlosyne leanira ssp.fulvia), was found to useCastilleja integra as a larval food plant at a localized site (Burnt Mill) southwest of Pueblo, Colorado. Field-captured adult butterflies contained the major iridoid glycosides (catalpol and macfadienoside) of theCastilleja. The content of a third iridoid glycoside, methyl shanzhiside, was also relatively high in the collected butterflies even though most individualCastilleja plants at Burnt Mill contained little or no methyl shanzhiside. Only a few plants, restricted to a small area, did contain appreciable methyl shanzhiside. Most of the plants that lacked the ester methyl shanzhiside contained shanzhiside, the corresponding free carboxylic acid.Thessalia larvae did not normally methylate the acid to produce methyl shanzhiside. Larvae that stopped feeding at an early instar, but yet survived several weeks, did contain major amounts of methyl shanzhiside. It is suggested that only larvae that overwinter or otherwise enter diapause convert shanzhiside to methyl shanzhiside. TheCastilleja food plant also contained iridoids other than catalpol and macfadienoside, sometimes in major amounts, but these were never found in larvae, pupae, or butterflies.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 1573-1561
    Keywords: Larkspur ; alkaloids ; intake regulation ; toxicity ; cattle
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Tall larkspur (Delphinium barbeyi) is a toxic forb often consumed by cattle on mountain rangelands, with annual fatalities averaging about 5%. This study examined the relationship between food ingestion and toxicity in cattle. Two grazing studies suggested that larkspur consumption above 25–30% of cattle diets for one or two days led to reduced larkspur consumption on subsequent days. We subsequently hypothesized that cattle can generally limit intake of larkspur to sublethal levels. This hypothesis was tested by feeding a 27% larkspur pellet in experiment 1. Cattle given a 27% larkspur pellet ad libitum showed distinct cyclic patterns of intake, where increased larkspur consumption on one or two days was followed by reduced (P 〈 0.025) consumption on the following day. The amount of larkspur (mean 2007 g/day; 17.8 mg toxic alkaloid/kg body wt) consumed was just below a level that would produce overt signs of toxicity. Experiment 2 was conducted to examine cattle response to a toxin dose that varied with food intake. Lithium chloride (LiCl) paired with corn ingestion was used as a model toxin, and we hypothesized that if increased (decreased) consumption was followed by a stronger (weaker) dose of LiCl, cattle would show a transient reduction (increase) in corn intake. There was no difference (P 〉 0.05) between controls and treatment animals at the 20 or 40 mg LiCl/kg dose in the percentage of corn consumed, but the 80 mg LiCl/kg dose induced a cyclic response (mean 46%) compared to intake by controls (mean 96%) (P 〈 0.001). At the 80 mg/kg dose, LiCl induced an aversion to corn; when corn intake decreased on subsequent days and LiCl dose also decreased, cattle responded by increasing corn intake and apparently extinguishing the transient food aversion. Experiment 3 was similar to the LiCl trial, except that tall larkspur was the toxin. Cattle responded to oral gavage of ground larkspur with distinct cycles; days of higher corn consumption were followed by one to three days of reduced consumption. Corn intake for controls was higher (P 〈 0.01) than for larkspur-treated animals (means 84 and 52%, respectively; day × treatment interaction P 〈 0.01). The threshold for toxic effects on corn intake was 14 mg toxic alkaloid/kg body weight. In conclusion, cattle apparently limit ingestion of some toxins so that periods of high consumption are followed by periods of reduced consumption to allow for detoxification. Cyclic consumption generally enables cattle to regulate tall larkspur consumption below a toxic threshold and allows cattle the opportunity to safely use an otherwise nutritious, but toxic, plant.
    Type of Medium: Electronic Resource
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  • 9
    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.
    Type of Medium: Electronic Resource
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  • 10
    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.
    Type of Medium: Electronic Resource
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