Callimorphine

Insect Biochemistry and Molecular Biology,2007,37(1):80–89.

Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids[Reference: WebLink]

METHODS AND RESULTS:
There are two classes of insect PAs, the creatonotines and the Callimorphines. The creatonotines contain as necic acids either 2-hydroxy-3-methylbutyric acid (creatonotine A) or 2-hydroxy-3-methylpentanoic acid (creatonotine B). The three known Callimorphines contain 2-hydroxy-2-methylbutanoic acid whose hydroxyl group can be either free (deacetylCallimorphine) or acetylated (Callimorphine) or propionylated (homoCallimorphine).
CONCLUSIONS:
Analysis of the creatonotines and Callimorphines isolated from the polyphagous arctiids Estigmene acrea and Grammia geneura that were fed with pure PAs and defined PA mixtures revealed the following absolute configuration: the Callimorphines and creatonotine A were present in 2′R configuration, whereas creatonotine B was found as mixture of (2′R, 3′S)- and (2′S, 3′S)-stereoisomers. The ratio of 2′S to 2′R was extremely variable ranging from 98% S to 94% R.

Tetrahedron Letters,1980,21(14):1383–1384.

Callimorphine: identification and synthesis of the cinnabar moth “metabolite”.[Reference: WebLink]

METHODS AND RESULTS:
Callimorphine, a putative pyrrolizidine alkaloid metabolite found in some Arctiid moths which feed as larvae on plants containing pyrrolizidine alkaloids, has been identified and synthesised.