Dihydromatricaria acid

Defensive Compounds. The aposematically coloured Chauliognathusfallax which feed on Senecio brasiliensis (Asteraceae) sequester the four pyrrolizidine alkaloids senecionine (100 main compound), integerrimine (101 main compound), retrorsine 102, and usaramine 103 [203] (Scheme 11). Other Chauliognathus-species may contain either precoccinelline 104 and related alkaloids (C. pul-chelus) or Z-dihydromatricaria acid 105 (C. pennsylvanicus). 

Most acetylenic compounds in plants are derived from meta-bolically altered fatty acids. These often are active in plant-insect relationships. 8-cis-Dihydromatricaria acid is also found in the defensive secretion of the soldier beetle (Chaulioqnathus 1econtei) (125), and has subsequently been shown to have anti-feedant properties against Phidippus spp. (jumping spiders) (126). As previously mentioned matricaria ester has antifeedant properties to the pink bollworm, bollworm and tobacco budworm (115). 

The cantharid beetle Chauliognathus lecontei defensively secretes from glands in its thorax and abdomen droplets of liquid containing as a major fraction 8-ds-decene-4,6-diynoic acid (or 8-cis-dihydromatricaria acid) (Meinwald et al., 1968). Ultraviolet and mass spectral data quickly led to the identification of the chromo-... 

Eisner, T., D. Hell, M. Goetz, S. Jain, D. Alsop, S. Camizine, and J. Meinwald, Antifeedant action of Z-dihydromatricaria acid from soldier beetles (Chauliognathus spp.), J. Chem. Ecol., 7, 1149-1158 (1981). 

Figure 10.18 Dihydromatricaria acid is found in cantharid beetles feeding on Compositae which contain polyacetylenic acids. Lucibufagins are similar to cardenolides, sequestered by fireflies. Romallenone is present in the defensive foam of a grasshopper...

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