Triterpene saponin hemi-biosynthesis of a leaf beetle’s (<Emphasis Type="Italic">Platyphora kollari</Emphasis>) defensive secretion

The adults of the leaf beetle Platyphora kollari (Chrysomelidae) are able to metabolise the oleanane triterpene β-amyrin (1) into the glycoside 3-O-β-d-glucopyranosyl-(1→4)-β-d-glucuronopyranosyl-hederagenin (2) that is stored in their defensive glands. The aim of this study was to test the hypothesis that oleanolic acid (3) is an intermediate in the conversion of 1 into 2 and to check whether the sequestration of pentacyclic triterpenes is selective in favour of β-amyrin (1). To this end, adults of P. kollari were fed with Ipomoea batatas leaf disks painted with a solution of [2,2,3-²H₃]oleanolic acid or [2,2,3-²H₃]α-amyrin and the secretion of their defensive glands analysed by HPLC–ESIMS. The data presented in this work indicated that the first step of the transformation of β-amyrin (1) into the sequestered glycoside 2 is its oxidation into oleanolic acid (3) and that this conversion is selective but not specific in favour of β-amyrin (1).     

Ladybird defence alkaloids: Structural,chemotaxonomic and biosynthetic aspects (Col.: Coccinellidae)

Summary The defensive mechanisms which protect ladybird beetles (Coccinellidae) against predators are reviewed. Besides behavioural mechanisms, such as thanatosis and reflex bleeding, chemical defence mechanisms are playing a prevalent role. Indeed, ladybirds are protected not only by their smell, but also by repulsive alkaloids, most of which are considered to be of autogenous origin. In a few cases, dietarily-acquired substances are also involved. Particular emphasis is laid on the repellent alkaloids which are contained in the haemolymph of many species. The structures of 34 nitrogen-containing compounds isolated so far are presented, and their distribution within the family is discussed in the light of the most widely accepted classification of these beetles. To conclude, the mode of release of the alkaloids, their variation through the life cycle and their repellent and toxic properties are discussed, as well as the few biosynthetic data yet available.     

De novo biosynthesis of Δ3-Isoxazolin-5-one and 3-Nitropropanoic acid derivatives inChrysomela tremulae

The nature of the cosmic redshift is one of the most fundamental questions in modern science. Hubble's discovery of the apparent Expansion of the Universe is derived from obsevations on a small number of galaxies at very low redshifts. Today, quasar redshits have a range more than 1000 times greater than those in Hubble's sample, and represent more than 100 times as many objects. A recent comprehensive compilation of published measurements provides the basis for a study indicating that quasar observations are not in good agreement with the original predictions of the Expanding Universe theory, but are well fit by the predictions of an alternative theory having fewer adjustable parameters.     

Chemical defense in Platyphora kollari Baly and Leptinotarsa behrensi Harold (Coleoptera: Chrysomelidae). Hypotheses on the origin and evolution of leaf beetles toxins

Summary. The defensive secretions of Platyphora kollari beetles (Chrysomelidae) from Brazil contained one oleanene glycoside. This was identified as 3-O-g-D-glucopyranosyl-(l̆)-g-D-glucuronopyranosyl-hederagenin (8), by a combination of 1D and 2D NMR methods (COSY, HMQC, MBC) and SIMS. There were also several amino acid derivatives, including the known non-protein amino acid (Z)-2-amino-3,5-hexadienoic acid (1), the new dipeptide L-n-glutamyl-2-amino-(3Z)-hexenoic acid (4), ethanolamine (7), and a mixture of phosphatidylcholines. Compounds 1 and 7 have already been identified in several leaf beetle taxa. Secretions of Leptinotarsa behrensi contained as major triterpene glycoside 3-O-g-d-glucopyranosyl-(l̅)-g-d-glucuronopyranosyl-oleanolic acid-28-O-g-d-glucopyranoside (9), already isolated from Platyphora opima. Although the host plants of these beetles were devoid of these triterpene glycosides, g-amyrin was shown to be present in three plants on which different species of triterpene-producing chrysomelids had been fed (Mikania micrantha, Ipomoea batatas and Convolvulus arvensis). This suggests that these insects are able to use g-amyrin from their food plant as a precursor to their oleanolic- and hydroxyoleanolic acid glycosides. The distribution of toxins already identified in leaf beetles suggests that amino acid derivatives could be a plesiomorphic character, considering their wide distribution, whereas the secretion of triterpene saponins, probably derived from ubiquitous plant triterpenes, could be an apomorphic character shared by some Doryphorina. The secretion of cardenolides derived from ubiquitous plant phytosterols would be another apomorphic character shared by other Doryphorina and Chrysolinina.     

An ecdysteroid (22-acetyl-20-hydroxyecdysone) from the defense gland secretion of an insect: <Emphasis Type="Italic">Chrysolina carnifex</Emphasis> (Coleoptera: Chrysomelidae)

Summary. 22-Acetyl-20-hydroxyecdysone was identified as a major component in the secretion of elytral and pronotal glands of Chrysolina carnifex, at an estimated concentration of 1.5 x 10^-1 M. This unexpected high concentration of an ecdysteroid in an exocrine secretion of an insect is discussed in terms of its potential defensive function, and in the light of steroid production in similar glands of closely related leaf beetles.     

“Pheromones and Animal Behaviour” - Communication by Smell and Taste”

Summary.  ((no summary.))A corrected version of the appendix is available for free download from