The venom of the honeybee (Apis mellifera): free amino acids and peptides

Abstract

The venom of the honeybee (Apis mellifera), obtained by electrical excitation, was fractionated by solvent extraction and gel filtration. The free amino acid and peptide content was determined by automated analysis. Less than 1% of the venom consisted of 19 free amino acids, while the minimum quantity of the 14 peptides was 15%. Two histapeptides were isolated and characterized. The sequence of histapeptide A was alanyl-glycyl-prolyl-alanyl-glutaminyl-histamine.

Chemistry and Pharmacology of Honey-bee Venom

“…Nineteen free amino acids have been detected in bee venom (Nelson and O'Connor, 1968) but in amounts consistent with their having been derived from haemolymph (Florkin and Jeuniaux, 1974). The lower proportions of glutamic acid, proline and lysine would be consistent with the usage of these in the synthesis of large quantities of melittin.a-Aminobutyric acid (0.04%) and ß-aminoisobutyric acid (0.02%), which are not significant constituents of haemolymph, might be genuine venom components.…”

“…Two or three homologous peptides with histamine present as the C-terminal residue have been isolated from Canadian bee venom by Nelson and O'Connor (1968). Their sequences are given in Fig.…”

Insect Venoms and Toxins

“…) venom stop growing, which after metamorphosis results in miniature flies, as small as one-quarter of the normal size. Studies of small peptides in bee venom (Nelson, D. and O'Connor, R., 1968) revealed the first natural source of histamine-terminal peptides in bee venom such as Ala-Gly-Pro-Ala-Glu-Histamine and Ala-Gly-Glu-Gly-Histamine ( = procamine) (Peck, M. and O'Connor, R., 1974). About 3% of the original dry mass was recovered in the minimine-fraction.…”

Studien über Wespengift, I Niedermolekulare Bestandteile des Giftblasenextraktes von Paravespula vulgaris / Studies on Wasp Venom, I Low Molecular Weight Constituents of Venom Sac Extracts from Paravespula vulgaris

“…Das vorherrschende Auftreten gerade jener Aminosäuren, die hauptsächlich das Propeptid des Bienengift-Haupttoxins Melittin aufbauen [16], dessen extrazellulärer Abbau zum freien Toxin vermutet wird [17], legt nahe, daß auch Peptidtoxine der Vespidengifte extrazellulär aus ähnlich strukturierten Protoxinen freigesetzt werden. Das nahezu völlige Fehlen der entsprechenden freien Aminosäuren im Apis mellifera-Gift [18] und ihr Auftreten in den Giften zweier Vespiden verschiedener Gattungen läßt darüber hinaus an einen Rückgewin-nungsmechanismus für die beim Protoxinabbau freigesetzten Aminosäuren in den Giftapparaten denken, der bei der hochentwickelten Honigbiene quantitativ arbeiten dürfte, bei den stammesgeschichtlich älteren Vespiden dagegen noch nicht gleichermaßen perfektioniert wäre.…”