New macrolactones from the defensive salivary secretion of soldiers of the african termite Pseudacanthotermes spiniger

Structure and function of defensive glands in soldiers of Glossotermes oculatus (Isoptera: Serritermitidae)

“…, 2009). The use of labial glands in soldier defence was confirmed in Mastotermes (Moore, 1968) and in several genera of Macrotermitinae (Maschwitz, Jander & Burkhardt, 1972; Plasman et al. , 1999).…”

Adhesive Exocrine Glands in Insects: Morphology, Ultrastructure, and Adhesive Secretion

“…Alkoxyethanols have been particularly noted as being useful in inhibiting the evaporation of water by acting as a monomolecular surface fi lm (Deo et al, 1965;Trapeznikov and Zaozerskaya, 1972). fi rst, by immobilizing the foe with an aqueous solution of a polysaccharide that, on evaporation of the solvent, forms an enrobing solid fi lm, and second, by simultaneously applying toxic macrolactones (Plasman et al, 1999). Mixtures of hydrocarbons (chiefl y 9-tricosene), honey, water, and either octadecyloxyethanol or sodium palmitate give highly stable emulsions (Keegans et al, 1993).…”

The First Total Synthesis of (−) and (+)-2-Hydroxy-24-oxooctacosanolide Using an Effective Lactonization

“…1-3 On the other hand, macrocyclic molecules, such as 3, 4, and 5, were also extracted from the salivary defensive secretion of soldier termites. 4,5 These compounds involve peculiar very large-size macrocyclic lactone moieties, however, and there are only a few reports on the chemical production of this type of giantsized lactone to the best of our knowledge.Recently, we developed a new and rapid lactonization of ω-hydroxycarboxylic acids using symmetrically substituted benzoic anhydrides, such as 2-methyl-6-nitrobenzoic anhydride (MNBA) as a condensation reagent. [6][7][8][9][10][11][12][13][14][15] (1) Cubitene and related compounds.…”

“…In this paper, we now report an effective synthesis of 2-hydroxy-24-oxooctacosanolide (5), the defensive secretion of the African termite Pseudacanthotermes spiniger, 5 using MNBA lactonization protocol as part of our continuous efforts to apply new synthetic methodology to produce biologically active macrolactones.…”

“…All spectral data, including the 1 H and 13 C NMR chemical shifts, IR absorption, and mass spectra of the synthetic (-)-5, correspond to those of the natural 29-membered lactone. 5 The produced (-)-5 was further converted into its benzoate 19 to determine the optical purity. The Mitsunobu inversion of (-)-5 using benzoic acid in the presence of DEAD and Ph 3 P produced the corresponding antipode ester ent-19 in good yield.…”