N

quinoline CH3 N-2-methylbutyl dimethylquinazolinedione 2-methylbutanamide polyzonamine

Figure 9.13 More unusual insect and arthropod alkaloids does so much damage to woodwork, N-2-methylbutyl 2-methylbutanamide is apparently derived from l-isoleucine. A millipede Polyzonium rosalbum produces polyzonamine (Figure 9.13) which has a very noticeable camphor-like odour. Polyzonamine evidently has a isoprenoid origin but its biosynthesis is not known.

The philanthotoxins (Figure 9.14) are a group of compounds from the venom of the bee-wolf Philanthus triangulatus, which preys on worker bees, stinging and paralyzing them. The compounds of the group differ in the number of carbon atoms between the nitrogens. The components of these compounds are easily recognized, a butyric acid amide of tyrosine in turn linked to putresine. Note the similarity of this part of the structure to spermidine and spermine, trace substances widely found in cells but of uncertain function. The bee-wolf lays its egg on the live but paralyzed bee, which provides fresh food for the larva when it hatches. Polyamines like spermine and spermidine are found in the venom of the funnel-web spider Atrax robustus, and have been identified in the venom of tarantula spiders some time ago. Compounds similar to the philanthotoxins have been identified in many spider venoms. The compound designated CNS 2103, based on tryptophan, has been found in the

spermine

Agel 489a

Figure 9.14 Philanthotoxins are alkaloids from wasp venom, spermine and spermidine occur in venoms and as part of these larger compounds. Compounds CNS 2103 and Agel 489a are from spider venoms spermine

Agel 489a

Figure 9.14 Philanthotoxins are alkaloids from wasp venom, spermine and spermidine occur in venoms and as part of these larger compounds. Compounds CNS 2103 and Agel 489a are from spider venoms venom of a fishing spider (Figure 9.14). It consists of hydroxylated indoleacetic acid amide linked to cadaverine that has been extended with three C3-NH2 units. About 70 such compounds are known in spider venoms, some have N-OH or N-CH3 groups. Agel 489a from Agenelopsis aperta is another example. Such compounds are described as polyaza-alkanes coupled to an aromatic head group.

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