Cardiodepressant and neurologic actions of Solenopsis invicta (imported fire ant) venom alkaloids

Venom alkaloids of monogyne and polygyne forms of the red imported fire ant, Solenopsis invicta, in Taiwan

“…The results showed that activities of nNOS and eNOS isoforms were over 95 % inhibited with 1000 mM of isosolenopsin A, whereas the enzyme activity for iNOS was inhibited by only about 20 % with the same concentration of isosolenopsin A (Yi et al, 2003). Both solenopsin A (trans-2-methyl-6-n-undecylpiperidine) and isosolenopsin A cause seizures and depress cardiovascular functions in rats (Howell et al, 2005).…”

The stinging impact of the imported fire ant

“…A considerable degree of overlap exists between the endemic areas in which C. vittatus and IFA are found. In massive fire ant attacks (>500 stings), cardiorespiratory failure may result from two alkaloid venom components, which possess significant cardiorespiratory depressant activity and have elicited seizures in mammal models [27].…”

Synthesis of enantiomerically pure fire ant venom alkaloids: Solenopsins and isosolenopsins A, B and C

“…The solution was stirred for 6 h at room temperature, concentrated in vacuum and extracted with diethyl ether (3x100 ml). The organic layer was dried over MgSO 4 , concentrated, and chromatographed on silica gel to give N-Boc-2(R)-undecylpiperidine as colorless oil (3.1 g, 89% 8 mmol) in anhydrous ether (75 ml) was cooled to -78 °C and treated with tetramethylethylenediamine (TMEDA) (2.0 ml) and s-BuLi (10.5 ml, 13.5 mmol) sequentially. The mixture was slowly warmed to -20 °C, stirred for 30 min and cooled again to -78 °C.…”

“…The reaction mixture was stirred for 6 h at room temperature, concentrated in vacuum and extracted with diethyl ether (3x150 ml). The ether extract was dried over MgSO 4 …”

“…In a previous communication, we reported that racemic isosolenopsin A and solenopsin A possess robust cardiorespiratory depressant activity in rats [4]. In order to investigate individual enantiomers of fire ant venom alkaloids on cardiorespiratory depressant activity, a simple and efficient procedure for their synthesis needed to be developed.…”