The larva of the green lacewing (Ceraeochrysa cubana) (Neuroptera, Chrysopidae) is a natural predator of eggs of Utetheisa ornatrix (Lepidoptera, Arctiidae), a moth that sequesters pyrrolizidine alkaloids from its larval foodplant (Fabaceae, Crotalaria spp.). Utetheisa eggs are ordinarily endowed with the alkaloid. Alkaloidfree Utetheisa eggs, produced experimentally, are pierced by the larva with its sharp tubular jaws and sucked out. Alkaloid-laden eggs, in contrast, are rejected. When attacking an Utetheisa egg cluster (numbering on average 20 eggs), the larva subjects it to an inspection process. It prods and͞or pierces a small number of eggs (on average two to three) and, if these contain alkaloid, it passes ''negative judgement'' on the remainder of the cluster and turns away. Such generalization on the part of the larva makes sense, because the eggs within clusters differ little in alkaloid content. There is, however, considerable between-cluster variation in egg alkaloid content, so clusters in nature can be expected to range widely in palatability. To check each cluster for acceptability must therefore be adaptive for the larva, just as it must be adaptive for Utetheisa to lay its eggs in large clusters and to apportion alkaloid evenly among eggs of a cluster.Ceraeochrysa cubana ͉ Chrysopidae ͉ Utetheisa ornatrix ͉ Arctiidae ͉ pyrrolizidine alkaloid T he moth Utetheisa ornatrix (family Arctiidae) (henceforth called Utetheisa) endows its eggs with pyrrolizidine alkaloids [henceforth called alkaloid(s)]. It sequesters the chemicals as a larva from its foodplants, legumes of the genus Crotalaria (family Fabaceae), and retains them through metamorphosis into the adult stage. Both parents contribute to the egg endowment. The male transmits alkaloid to the female with the sperm package at mating, and the female allocates a portion of this gift, together with a share of her own alkaloid, to the eggs (1).Here we present evidence that the alkaloids protect the eggs against a natural enemy, the larva of the green lacewing, Ceraeochrysa cubana (family Chrysopidae) ( Fig. 1 A and B). Specifically, we demonstrate that (i) the larva, in laboratory tests, rejects alkaloid-containing Utetheisa eggs, while avidly consuming alkaloid-free eggs offered as controls; (ii) the larva exercises this discrimination in the field as well; (iii) the larva is more strongly deterred by the N-oxide form of the alkaloid than the free base form; (iv) the alkaloid in Utetheisa eggs occurs mainly in the N-oxide form; (v) the eggs in a given cluster are equally endowed with alkaloid; and (vi) the larva seems to act on this information: it abandons a cluster, no matter what the cluster size, if the first few eggs it samples are distasteful. Materials and MethodsThis study was done at our Cornell laboratories and at the Archbold Biological Station, Lake Placid, Highlands County, FL.Experimental Animals. Utetheisa occur at the Archbold Station, often in abundance, in association with stands of Crotalaria mucronata, the major local foodplant. ...

The total synthesis of racemic cis-2,3,18',18*-tetrahydroprotobiliverdin I X a dimethyl ester (19b), which is identical with the dimethyl ester of rac-4, is described (Scheme 2). Under virtually neutral conditions, in solution, this bile pigment isomerized within a few min to racemic Z-phycocyanobilin dimethyl ester (rue-5b). Likewise, acid-catalyzed ally1 rearrangement of 3-vinyl-substituted cis-and trans-2,3-dihydrodipyrrin-1 (10H)-ones l l c and 13c, respectively, yielded the corresponding ethylidene derivatives. In this case, however, the E-isomer was formed stereoselectively from both substrates. The above results prove that, if protobiliverdin

The ovaries of the marine snail Turbo cornutus contain a number of pigments. So far, the presence of carotenoids and a chromoprotein with a bile pigment, called turboverdin (=32‐hydroxy‐mesobiliverdin IXα), as its prosthetic group are known. The present work describes the isolation and structure elucidation of two further bile pigments, biliverdin IXδ and neobiliverdin IXδ. This is the first report of naturally occurring bile pigments with IXδ structure.

AbstractA 3-step synthesis of 5-aminolevulinic acid is described.