Danaidone

J Chem Ecol. 2005 Apr;31(4):959-64.

Differential utilization of pyrrolizidine alkaloids by males of a danaid butterfly, Parantica sita, for the production of danaidone in the alar scent organ.[Pubmed: 16124262]

Males of the chestnut tiger butterfly, Parantica sita, secrete Danaidone as a major component from the alar androconial organ (sex brand).
METHODS AND RESULTS:
Since Danaidone has been postulated to be derived from various pyrrolizidine alkaloids (PAs), which males ingest as adults from PA-containing plants, we conducted oral administration tests of several PAs to examine their availability for Danaidone production by P. sita males. Males fed with a mixture of intermedine (80%) and lycopsamine (20%) produced Danaidone at an average of 25.7 microg per individual, which was comparable to that found in field-caught males. In contrast, a smaller amount of Danaidone (5.7 to 7.0 microg/ male) was formed when males ingested retronecine or heliotrine, and those fed with an HCI salt of monocrotaline or retrorsine produced only traces of Danaidone (<0.5 microg/male). In addition, males showed a strong feeding response to intermedine/lycopsamine, whereas the other PAs elicited no positive feeding behavior.
CONCLUSIONS:
These results indicate that, unlike the arctiid moths, P. sita males can only successfully convert limited chemical types of PAs into Danaidone, and further suggest that in the field, males selectively ingest particular PAs that are readily transformable into Danaidone.

Experientia. 1989 Sep 15;45(9):896-8.

Paternal allocation of sequestered plant pyrrolizidine alkaloid to eggs in the danaine butterfly, Danaus gilippus.[Pubmed: 2776861]

METHODS AND RESULTS:
Pyrrolizidine alkaloid sequestered by adult male Danaus gilippus from plants is transferred in large measure to the female at mating, and by the female to the eggs. The eggs, presumably, are protected as a result. The male's courtship pheromone, Danaidone, derived from the sequestered alkaloid, may function to advertise the male's alkaloid-donating capacity.

J Chem Ecol. 1996 May;22(5):949-72.

Male sex pheromone of a giant danaine butterfly,Idea leuconoe.[Pubmed: 24227617]

METHODS AND RESULTS:
Males of a giant danaine butterfly,Idea leuconoe, display hairpencils during courtship. The females were visually attracted to and olfactorily arrested by an artificial butterfly model to which male hairpencil extracts were added. The hairpencil extracts contained a complex mixture of volatiles, including pyrrolizidine alkaloid (PA) derivatives (Danaidone, viridifloric β-lactone), aromatics (phenol,p-cresol, benzoic acid), terpenoids (geranyl methyl thioether, (E,E)-farnesol), a series of γ-lactones (6-hydroxy-4-undecanolides and its homologs), hydrocarbons [(Z)-9-tricosene, etc.], and several compounds with higher molecular weight. A mixture of the major volatiles applied to a butterfly dummy strongly elicited an abdomen-curling acceptance posture in females. Viridifloric β-lactone and Danaidone induced significant electroantennogram responses on the female's antennae, suggesting their principal role together with other hairpencil components as a sex pheromone to seduce females.I. leuconoe males seem to acquire the precursor for both of the PA fragments from the host plant,Parsonsia laevigata (Apocynaceae), during the larval stage; thereby they do not show pharmacophagous behavior towards PA-containing plants during the adult stage. However, males are pharmacophagously attracted to and feed on a number of simple phenolic compounds in a manner similar to other danaine species towards PAs.
CONCLUSIONS:
Wild males sequester one of the phagostimulants, (-)-mellein, in the hairpencils in varying quantities. Phenolic compounds incorporated in the hairpencils may act primarily as warning odors linked with the defensive PAs present in the body tissues.

Biochemical Systematics and Ecology, 1982,10( 2): 181-3.

Major components in the hairpencil secretions of Danaid butterflies from Far East Asia[Reference: WebLink]

METHODS AND RESULTS:
A survey of the components in the hairpencil secretions of 10 species of danaid butterflies from Japan and Formosa has been carried out to indicate whether they provide information of taxonomic significance compared to American, African and Australian species. The Far East species contained hydroxydanaidal and/or Danaidone and the genus Euplosa contained trans-β-ocumene and linalool in addition.
CONCLUSIONS:
These results suggest that the components of the secretion of Far East species are very similar to those in danaids from Australia.