6-Alkylsalicylic Acids and 6-Alkylresorcylic Acids from Ants in the Genus Crematogaster from Brunei

Abstract

The defensive chemistry of two species of ants from Brunei in the genus Crematogaster (Physocrema group) has been investigated. Ants in this group release a white secretion from hypertrophied metapleural glands on their thorax when they are disturbed. Previously, one species in this group has been shown to produce alkylphenols and alkylresorcinols. In the present investigation, similar compounds along with salicylic acids and resorcylic acids that are anacardic acid and olivetolic acid homologs, respectively, are described from two species. The structures of these compounds were suggested by their spectroscopic data and confirmed by direct comparison with synthetic samples. Some of these compounds occur in lichens and have well documented physiological activities.

Ant Interactions with Soil Organisms and Associated Semiochemicals

“…Instead, their MGs are highly developed; in fact, C. inflata has the largest known MGs (measured by secretory cell counts, Billen et al 2011). Metapleural gland chemistry has been reported for C. difformis in two reports, one using samples collected from Malaysia (Attygalle et al 1989) and the other from Brunei (Jones et al 2005). The MG chemistry of each is so unique (combinations of 6-alkylsalicylic and 6-alkylresorcylic acids, 5-alkylresorcinols and 3-alkylphenols; see Table 1, Fig.…”

“…The MG chemistry of each is so unique (combinations of 6-alkylsalicylic and 6-alkylresorcylic acids, 5-alkylresorcinols and 3-alkylphenols; see Table 1, Fig. 3) that Jones et al (2005) suggested that they are likely different species. Comparison with a third species, C. inflata (Jones et al 2005), shows a third blend of components (Table 1, Fig.…”

“…3) that Jones et al (2005) suggested that they are likely different species. Comparison with a third species, C. inflata (Jones et al 2005), shows a third blend of components (Table 1, Fig. 3).…”

Secondary metabolism in cannabis

“…4 Proposed biogenetic pathway for cannabinoids with C 3 side-chain of phloroglucinol glucoside in cannabis (Hammond and Mahlberg 1994) suggests a regulatory role for olivetolic acid in the biosynthesis of cannabinoids (Fig. 3), although, the presence of olivetolic acid and olivetol in ants from genus Crematogaster has been reported (Jones et al 2005); both olivetolic acid and olivetol are classified as resorcinolic lipids (alkylresorcinol, resorcinolic acid); these last ones have been detected in several plants and microorganisms (Roos et al 2003;Jin and Zjawiony 2006). Kozubek and Tyman (1999) suggested that alkylresorcinols, such as olivetol, are formed from biosynthesized alkylresorcinolic acids by enzymatic decarboxylation or via modified fatty acid-synthesizing enzymes, where the alkylresorcinolic acid carboxylic group would be expected to be also attached either to ACP (acyl carrier protein) or to CoA.…”

The metapleural glands of fungus-growing and non-fungus-growing ants: Ultrastructural study

“…Abbreviations: c, canaliculi; cc, collecting chamber; cut, cuticle; ep, single squamous epithelium; p, sieve plates; r, reservoir; sc, secretory cells. Modified from Vieira et al (2010). 1898; Donisthorpe, 1941;Hosoishi & Ogata, 2008), with a secretion consisting of a mixture of phenolic compounds that are harmful to predators (Attygale et al, 1989;Jones et al, 2005). Finally, Maschwitz et al (1970) and Maschwitz (1974) reported antibiotic properties of secretion produced by the metapleural gland of ants.…”