Dihydropyrrolizine derivatives in the ‘hair-pencil’ secretions of danaid butterflies

Edgar, J. A.; Culvenor, C. C. J.; Smith, L. W.

doi:10.1007/bf02136849

Cited by 57 publications

(28 citation statements)

References 6 publications

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“…However, the biological significance has been elucidated only in a limited number of species (Boppré, 1984;Honda, 1986a, b). Adult males of danaid butterflies have abdominal brush-like and/or alar secretory organs from which dihydropyrrolizine and b-lactone substances are secreted as aphrodisiacs (Pliske and Eisner, 1969;Edgar et al, 1971;Komae et al, 1982;Eisner and Meinwald, 1987;Schulz et al, 1988;Honda et al, 1995;Nishida et al, 1996). Several pierid adults use the alar androconia to disperse characteristic volatiles such as geranial and neral in Pieris melete and P. napi (Bergström and Lundgren, 1973;Hayashi et al, 1978;Kuwahara, 1979), methyl esters of some aliphatic acids and various components in P. rapae (Honda and Kawatoko, 1982), and b-ocimene in Delias spp.…”

Section: Introductionmentioning

confidence: 99%

Chemical composition of volatile substances from adults of the swallowtail, Papilio polytes (Lepidoptera: Papilionidae)

Ômura

Honda

2005

Appl. Entomol. Zool.

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Adults of the swallowtail butterfly Papilio polytes have a faint scent, which is stronger in males than in females. From the solvent extracts from adults, six relatively high-volatile substances including linalool, nonanal, and decanal were detected in small amounts. Since males contained more linalool than females in the average amount per individual, this compound is believed to be attributable the male's strong scent. The majority of the substances is somewhat concentrated on the wings rather than on the body, whereas acetoin is mainly present in the body, particularly in the thorax for both sexes. In addition, the solvent extracts were found to have large amounts of relatively low-volatile substances in which six n-alkanes, three n-alkenes, and four carboxylic acids possessing 10 to 29 carbon numbers were identified, and the major components were n-heptacosane, n-nonacosane, and hexadecanoic acid. In the extracts from individual whole 3-d-old adults, (Z)-7-tricosene and dodecanoic acid were significantly more abundant in males than in females, while (Z)-7-pentacosene and n-heptacosane were significantly more abundant in females than in males, indicating that the swallowtail adults have a sexual dimorphism in volatile composition. During the 3 d after emergence, most of the identified components averagely increased by twice the amount per adult.

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Section: Introductionmentioning

confidence: 99%

Chemical composition of volatile substances from adults of the swallowtail, Papilio polytes (Lepidoptera: Papilionidae)

Ômura

Honda

2005

Appl. Entomol. Zool.

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“…The PA Danaidal (1-formyl-6,7-dihydro-5H-pyrrolizine) had been reported as a pheromone [21] in some exotic butterflies [22]. More recently classic PAs from plants such as Ragwort (Senecio jacobaea) have been reported to be anti-bacterial, however, they are too toxic to be suitable as oral drugs [23] [24] [25].…”

Section: Discussionmentioning

confidence: 99%

Butterflies Extracts Show Antibacterial Activity

Rasooly¹,

Rothschild²,

Gov³

et al. 2017

AiM

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Extracts of several British butterfly species were tested and shown to possess powerful bactericidal activity against gram-positive bacteria (tested on Staphylococcus aureus and Bacillus anthracis). The active compounds in the grass-feeding species were identified as hydroxylated pyrrolizidine alkaloids (PAs) related to loline with nitrogen at C-1. Lolines are known insecticidal and insect-deterrent compounds that are produced in grasses infected by endophytic fungal symbionts. Lolines also increase resistance of endophyte-infected grasses to insect herbivores. The butterfly-isolated pyrrolizidine alkaloids appear to be novel and non-toxic to human cells such as HaCat human skin keratinocytes and Hep-2 human epithelial cells. The discovery of novel agents from butterflies could lead to the development of new antimicrobials.

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“…Male coremata and the glandular structures that produce PA derivatives occur in a variety of both moths (Arctiidae) and butterflies (Danainae) (Boppré 1990;Edgar et al 1971;Hartmann & Ober 2000;Nishida 2002;Weller et al 1999). These derivatives, which are of diverse chemical structure, may well function, as HD does in Utetheisa, primarily for proclamation of PA content on the part of males in courtship (Eisner & Meinwald 2003).…”

Section: Discussionmentioning

confidence: 99%

Corematal function in Utetheisa ornatrix (Lepidoptera: Arctiidae): Hydroxydanaidal is devoid of intrinsic defensive potency

2006

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Hydroxydanaidal, the pyrrolizidine alkaloidderived male corematal pheromone active in the close-range precopulatory interactions of the moth Utetheisa ornatrix, appears not to contribute to the chemical defense of this moth. The compound failed to manifest feeding deterrency as an additive to mealworms, in assays with a lycosid spider (Lycosa ceratiola). Moreover, contact with the male's coremata, such as appears to occur inevitably in consequence of courtship in Utetheisa, does not in itself reduce the palatability of the female moth.

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Dihydropyrrolizine derivatives in the ‘hair-pencil’ secretions of danaid butterflies

Cited by 57 publications

References 6 publications

Chemical composition of volatile substances from adults of the swallowtail, Papilio polytes (Lepidoptera: Papilionidae)

Chemical composition of volatile substances from adults of the swallowtail, Papilio polytes (Lepidoptera: Papilionidae)

Butterflies Extracts Show Antibacterial Activity

Corematal function in Utetheisa ornatrix (Lepidoptera: Arctiidae): Hydroxydanaidal is devoid of intrinsic defensive potency

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