Primary Tetradecenyl Amines from the Ant Monomorium floricola

Abstract

In contrast to other ants in the genus Monomorium that produce cyclic amines, extracts of Monomorium floricola contain (Z)-7-tetradecenylamine (1) and (Z)-9-tetradecenylamine (2). The structures of these compounds were established from their spectral data and by comparison with synthetic 2.

Caste-Specific Tyramides from Myrmicine Ants

“…11 The second and roughly equimolar component at Rt 21.0 min had the following. EIMS: [M + ] m/z 249 (2), 234 (1), 206 (1), 164 (4), 121 (35), 120 (100), 107 (22), 91 (9), 85 (13), 77 (18), 57 (40), 43 (8), 41 (20). Initially, it was assumed that this component was a three-carbon homologue of 2; however, the high-resolution mass spectrum (HRMS m/z 249.1361, calcd for C 14 H 19 NO 3 , m/z 249.1365) indicated the presence of a third oxygen and another double-bond equivalent.…”

“…A solution containing 0.26 g of 2-hydroxy-3-methylpentanoic acid 14 (2 mmol) was condensed with tyramine as described for 5a to provide 0.8 g of a mixture that was 70% pure, with the remainder being benzotriazole: 1 164 (2), 132 (6), 121 (17), 120 (100), 107 (11), 91 (4), 77 (8), 45 (9); HRMS m/z 251.1543, calcd for C 14 H 21 NO 3 , m/z 251.1521.…”

“…Ring-saturated nitrogen heterocycles are well-known components of the venoms of ants in the subfamily Myrmicinae, particularly in the genera Megalomyrmex , Monomorium , Myrmicaria , and Solenopsis . – While different species of ants may have some of the same alkaloids, the alkaloid composition of a particular species seems to be characteristic, varying only with the age of the ants . In several cases, a marked difference has been observed between the venom alkaloids produced by queens and those produced by workers of a particular species. , The venom alkaloids found in the workers, and in some cases the queens, of the species reported in this investigation, Monomorium minimum , Monomorium pharaonis , Monomorium floricola , Myrmicaria opaciventris , Solenopsis molesta , and Solenopsis maboya , have been described, while those of Monomorium ebeninum are very similar to those of M. miminum . ,– These compounds are conspicuously absent in the extracts of all male ants in these genera, which do not have venom glands. Herein we describe, however, not the presence of alkaloids but the occurrence of a set of acylated tyramines ( 1 − 3 and 4c ) from males of nine species of the genera Monomorium , Myrmicaria, , and Solenopsis (Diplorhoptrum) .…”

“…6,7 The venom alkaloids found in the workers, and in some cases the queens, of the species reported in this investigation, Monomorium minimum, Monomorium pharaonis, Monomorium floricola, Myrmicaria opaciVentris, Solenopsis molesta, and Solenopsis maboya, have been described, while those of Monomorium ebeninum are very similar to those of M. miminum. 1,[7][8][9] These compounds are conspicuously absent in the extracts of all male ants in these genera, which do not have venom glands. Herein we describe, however, not the presence of alkaloids but the occurrence of a set of acylated tyramines (1-3 and 4c) from males of nine species of the genera Monomorium, Myrmicaria,, and Solenopsis (Diplorhoptrum).…”

Fatty Amines from Little Black Ants, Monomorium minimum, and Their Biological Activities Against Red Imported Fire Ants, Solenopsis invicta

“…Searching by name or CAS number for both compounds using Chapman & Hall (Jones et al 1996) and (2Z)-farnesylamine in M. fieldi (Jones et al 2003). Although secondary and tertiary amines have been found in ponerine ants in the genus Mesoponera (Fales et al 1984), ants in the genus Monomorium appear to be the only established natural producers of primary amines.…”