Adalia beetles

Outline of the formation of adaline and adalinine, fatty acid-derived defensive compounds of Adalia beetles, The structure A is the same as in Figure 3.26. The compounds from Cryptolaemus montrouzieri are evidently ofrelated origin... 

Attractive Compounds. While the defence chemistry of ladybird beetles has been extensively investigated, little is known about intraspecific communication. The role of chemical and behavioural cues has been described in mate recognition in Adalia bipunctata. Cuticular hydrocarbons, especially 7- and 9-methyltri-cosane seem to play an important role [301]. In Coccinella septempunctata, 2-isopropyl-3-methoxypyrazine 158 (see Scheme 17) accounting for the dis-... 

A number of nemertine worms, such as Amphiporus or Nereis, produce alkaloids such as 2,3-bipyridyl, anabaseine, nemertelline, or nereis-toxin, which are toxic to predators such as crayfish 4,17,28,230,226,). Arthropod-made alkaloids include glomerine and homoglomerine in Glom-erus 215), adaline in Adalia 227), coccinelline, euphococcinine, and derivatives in Coccinella, Epilachna, and other coccinellid beetles 28,226,227,235), and stenusine in Stenus 215), which are considered to be antipredatory compounds 4,17,28,494-496). 

Adaline (333) was synthesized as described above for euphococcinine [699]. The two-spot ladybird beetle Adalia bipunctata was found to have a considerable investment in defense via its secretion of adaline-rich reflex blood [700]. 

CjjHjjNO, Mr 209.33, [a] -13 (CHCI,), cryst., mp. 204-205 °C (hydrochloride). Bicyclic alkaloid from ladybird beetles of the genus Adalia. It is biosynthet-ically related to coccinelline, the major alkaloid of ladybird beetles. Homologues of A. have been identified in Euphorbia plants. 

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