![]() ![]() 256 Whether consumed pyrrolizidine alkaloids are degraded upon saponification and further processing or via a transesterification step 257,258 may need further investigations. It is remarkable that caterpillars of the arctiid moth Utetheisa ornatrix, monophagous on Crotolaria species, can taste the alkaloids contained in its host plant. 255 Some other species do not distinguish. 254 It is interesting to note that butterflies producing such compounds may differentiate between the precursor alkaloids: Parantica sita is able to process the alkaloids intermedine or lycopsamine (monoesters that carry a (7 R)-OH group) in contrast to heliotrine (monoester with (7 S)-OH group) and retrosine or monocrotaline (diesters that carry a (7 R)-OH group). 253 The butterflies sequester precursors of the dihydropyrrolizines Ar50–Ar52 from plants and convert them into the pheromones. 252–254 Sometimes, the related compound danaidal ( Ar52), lacking the hydroxy group, is used by arctiine moths too. 249–251 The absolute configuration of Ar51 was determined in a few species only, but proved to be ( R) in all cases. It is used by many male danaine, ithomiine, and arctiine butterflies, preferentially as part of a courtship pheromone. 248 A more widespread dihydropyrrolizine pheromone is hydroxydanaidal ( Ar51). ![]() 246,247 Despite its presence in scent glands of many danaine butterflies, the pheromonal function of Ar50 was shown in only one additional species Idea leuconoe. 245ĭanaidone ( Ar50), the male courtship pheromone of the queen butterfly Danaus gilippus, was one of the first pheromones identified. The mixture of N-isopentyl-2-phenylethylamine ( Ar49), anabasine (neonicotine, Ar58), anabaseine (nornicotine, Ar59), and 2,3′bipyridyl ( Ar60) constitutes the trail pheromone of the ant Aphaenogaster rudis. 181 Together with methylpyrazine ( Ar44), Ar45, trimethylpyrazine ( Ar46), and Ar47, it represents the trail pheromone of the ant Tetramorium meridionale. Indole ( Ar53) is part of the antiaphrodisiac pheromone of male P. 242 2-Isopropyl-3-methoxypyrazine ( Ar42), a widespread warning odor of insects, acts as a pheromone in the seven-spotted ladybird beetle Coccinella septempunctata. 241 2,3-Dimethyl-5-(2-methylpropyl)pyrazine ( Ar48) is the trail pheromone of the ant Eutetramorium mocquerysi. 240 A 7:3 mixture of Ar47 and 2,5-dimethylpyrazine ( Ar45) comprises the trail pheromone of Tetramorium caespitum. 236 It is also the recruitment pheromone of Pogonomyrmex harvester ants. 3-Ethyl-2,5-dimethylpyrazine ( Ar47) has the same function in Atta sexdens, 235,236 Manica rubida, 237 Myrmica incompleta, 238 and Messor bouvieri, 239 as well as in several Myrmica spp. ![]() Various pyrazines act as trail pheromones of ants. 234 Methyl nicotinate ( Ar41) is the minor component of the trail pheromone of an Aenictus sp. 233 Two Metapone ant species use the unsubstituted derivative Ar40 as the trail pheromone. It is used by Atta texana, 231 Atta cephalotes, 232 and Acromyrmex octospinosus. Methyl 4-methylpyrrole-2-carboxylate ( Ar7) was the first trail pheromone identified in ants. Wittko Francke, Stefan Schulz, in Comprehensive Natural Products II, 2010 4.04.4.1 Nitrogen-Containing Aromatic Compounds ![]()
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