Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids

Beuerle, Till; Theuring, Claudine; Klewer, Nico; Schulz, Stefan; Hartmann, Thomas

doi:10.1016/j.ibmb.2006.10.005

Cited by 7 publications

(10 citation statements)

References 35 publications

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“…14,15,[27][28][29] We assigned the absolute stereochemistry of PAs based only in retention index of chiral PAs reported in the literature. 20,27 Chemical defense of Scearctia figulina: predation bioassays…”

Section: Pyrrolizidine Alkaloid Analysismentioning

confidence: 99%

“…Based on the retention index, we assume that all insect PAs have a 7R configuration, and show the absolute configuration of necic acid moiety identical to those reported by literature (Figure 1). 20 For the 7-deoxy-1,2-dihydrocallimorphine (XVI), the asymmetric center at C1 has R configuration. 20 Insect PAs accounted for approximately 20% of PAs in S. figulina.…”

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

“…20 For the 7-deoxy-1,2-dihydrocallimorphine (XVI), the asymmetric center at C1 has R configuration. 20 Insect PAs accounted for approximately 20% of PAs in S. figulina. Three unidentified PAs were found, and they accounted for 8% of relative abundance.…”

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

“…19 In the insect PAs of the callimorphine type, necic acids are derived from isoleucine, while in the creatonotine type, they are derived from valine. 16,20 Callimorphine type PAs were found in the Arctiina Arctia caja, Creatonotos transiens, Estigmene acrea, and Grammia geneura, in the Callimorphina Callimorpha dominula and Tyria jacobaea, and in the Pericopina Gnophaela latipennis and Hyalurga syma. [14][15][16] PAs of the creatonotine type were found in the Arctiina Creatonotos transiens, Estigmene acrea, and Grammia geneura, and in the Callimorphina Utetheisa ornatrix.…”

Section: Introductionmentioning

confidence: 98%

“…20 For the 7-deoxy-1,2-dihydrocallimorphine (XVI), the asymmetric center at C1 has R configuration. 20 Insect PAs accounted for 1441 Vol. 27, No.…”

mentioning

confidence: 99%

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Pyrrolizidine Alkaloids in the Pericopine MothScearctia figulina(Erebidae: Arctiinae): Metabolism and Chemical Defense

Martins

Trigo

2016

Journal of the Brazilian Chemical Society

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Pyrrolizidine alkaloids (PAs) are defensive compounds present in several plant families. However, some specialist herbivore insects have overcome these toxic compounds and sequester PAs converted to N-oxide as a defense against predators and a precursor of male sexual pheromones. In this context, we investigated PA sequestration by the specialist pericopine moth Scearctia figulina (Erebidae: Arctiinae), which feeds on leaves of Heliotropium transalpinum (Boraginaceae) as larvae. Additionally, we examined the role of PAs against different predators. The PAs sequestered from the host plant were metabolized by larvae and transferred to adults via two main pathways: (i) rinderine and its acetyl derivative (7S,3'R) were epimerized to intermedine (7R,3'R) and lycopsamine (7R,3'S), and (ii) insect PAs were biosynthesized from necine bases obtained from plant-acquired PAs, with necic acids of insect origin. Both metabolic products may be related to the biosynthesis of 7R male pheromone and to chemical defense. Larvae and adults were chemically protected against the spiders Nephila clavipes and Lycosa erythrognatha and the chick Gallus gallus, and this defense may be associated to PAs. Keywords: callimorphine, Heliotropium transalpinum, insect PAs, lycopsamine, predation IntroductionPyrrolizidine alkaloids, particularly 1,2-dehydropyrrolizidines (hereafter PAs), are powerful defensive compounds in several plant taxa, such as Eupatorieae and Senecioneae (Asteraceae), Boraginaceae, and Crotalarieae (Leguminosae).1,2 However, specialized herbivores, such as arctiine moths, danaine and ithomiine butterflies and chrysomeline beetles, among others, are able to cope with pro-toxic free-base PAs from these plants, converting them into non-toxic N-oxides.3,4 These insects sequester PA N-oxides, incorporating them into their tissues, and this renders chemical protection against predators and parasitoids.1,5 Arctiine moths and danaine and ithomiine butterflies also use PAs as precursors of male sexual pheromones, such as the dihydropyrrolizine hydroxydanaidal.6-8 PAs were also recorded in the grasshopper Zonocerus variegatus, the aphid Aphis jacobaeae, the bug Largus rufipennis, and the coccide Ceroplastes albolineatus.1 PA-containing insects are generally aposematic, i.e., their unpalatability is associated with warning signals alerting predators of this trait; warning signals can be visual, sonorous, or odorant. 9Among arctiine moths, 10 PAs were found in the tribes Amerilini and Arctiini (subtribes Callimorphina, Arctiina, Pericopina, Ctenuchina, Euchromiina, and Phaegopterina), but not in Lithosiini and Syntomini. 11 Three PA acquisition strategies were found in these moths: (i) PA-obtained as adults, (ii) PA-specialist feeding as larvae, and (iii) PA-generalist feeding as larvae.11 In the first syndrome, adults either feeding on nectar containing PAs or display a pharmacophagous behavior, or obtaining the alkaloid visiting withered PA-containing plants. 2,12,13 This syndrome was widely found in Ctenuchina, Euchromiina, an...

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Section: Pyrrolizidine Alkaloid Analysismentioning

confidence: 99%

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

“…20 For the 7-deoxy-1,2-dihydrocallimorphine (XVI), the asymmetric center at C1 has R configuration. 20 Insect PAs accounted for 1441 Vol. 27, No.…”

mentioning

confidence: 99%

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Pyrrolizidine Alkaloids in the Pericopine MothScearctia figulina(Erebidae: Arctiinae): Metabolism and Chemical Defense

Martins

Trigo

2016

Journal of the Brazilian Chemical Society

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Defense by Pyrrolizidine Alkaloids: Developed by Plants and Recruited by Insects

Hartmann

Ober

Induced Plant Resistance to Herbivory

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Arbuscular Mycorrhizal Fungi and Plant Chemical Defence: Effects of Colonisation on Aboveground and Belowground Metabolomes

et al. 2018

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Arbuscular mycorrhizal fungal (AMF) colonisation of plant roots is one of the most ancient and widespread interactions in ecology, yet the systemic consequences for plant secondary chemistry remain unclear. We performed the first metabolomic investigation into the impact of AMF colonisation by Rhizophagus irregularis on the chemical defences, spanning above- and below-ground tissues, in its host-plant ragwort (Senecio jacobaea). We used a non-targeted metabolomics approach to profile, and where possible identify, compounds induced by AMF colonisation in both roots and shoots. Metabolomics analyses revealed that 33 compounds were significantly increased in the root tissue of AMF colonised plants, including seven blumenols, plant-derived compounds known to be associated with AMF colonisation. One of these was a novel structure conjugated with a malonyl-sugar and uronic acid moiety, hitherto an unreported combination. Such structural modifications of blumenols could be significant for their previously reported functional roles associated with the establishment and maintenance of AM colonisation. Pyrrolizidine alkaloids (PAs), key anti-herbivore defence compounds in ragwort, dominated the metabolomic profiles of root and shoot extracts. Analyses of the metabolomic profiles revealed an increase in four PAs in roots (but not shoots) of AMF colonised plants, with the potential to protect colonised plants from below-ground organisms.Electronic supplementary materialThe online version of this article (10.1007/s10886-017-0921-1) contains supplementary material, which is available to authorized users.

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Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids

Cited by 7 publications

References 35 publications

Pyrrolizidine Alkaloids in the Pericopine MothScearctia figulina(Erebidae: Arctiinae): Metabolism and Chemical Defense

Pyrrolizidine Alkaloids in the Pericopine MothScearctia figulina(Erebidae: Arctiinae): Metabolism and Chemical Defense

Defense by Pyrrolizidine Alkaloids: Developed by Plants and Recruited by Insects

Arbuscular Mycorrhizal Fungi and Plant Chemical Defence: Effects of Colonisation on Aboveground and Belowground Metabolomes

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