Isolation and identification of amides from Piper callosum. Synthesis of pipercallosine and pipercallosidine

Abstract

Extraction of the roots of the shrub Piper callosum with cyclohexane afforded piperovatine (1 ) [N-isobutyl-6-(pmethoxyphenyl)sorbamide] and two new amides, the isobutylamides of (2€,4€) -9-(3,4-methylenedioxyphenyl)nona-2,4-dienoic acid and (E) -7-(3,4-methylenedioxyphenyl) hept-2-enoic acid, named pipercallosine (3) and pipercallosidine (14), respectively. The structures of the two new amides have been confirmed by synthesis.

Isolation, Synthesis, and Evolutionary Ecology of Piper Amides

“…Diverse methods for isolation and quantification of amides are described in papers such as Pring (1982), Gbewonyo and Candy (1992), Bernard et ai. (1995), Alecio et ai.…”

Anti-inflammatory activity of the extract, fractions and amides from the leaves of Piper ovatum Vahl (Piperaceae)

“…Previous phytochemical studies have investigated the local anesthetic and saliva-producing (sialogogic) properties of the Piper species and piperovatine, an extract isolated from Piper (Price and Pinder, 1970;Costa and Mors, 1981;Giesbrecht et al, 1981;Pring, 1982;Makapugay et al, 1983). Insecticidal isobutylamides isolated from Piper species have been synthesized (Crombie et al, 1987), and previous studies have suggested that extracts and single constituents of Piper nigrum and Piper methysticum possess inhibitory properties that are specific to cyclooxygenase-1, an important enzyme in the formation of prostaglandins, which in turn are important mediators of the development of inflammatory diseases (Gleitz et al, 1997;Venkateshwarlu, 1997).…”

Analysis of amide compounds in different parts of Piper ovatum Vahl by high-performance liquid chromatographic

“…[7] The amides piperovatine and piperlonguminine have been isolated from other species of Piper . [891011121314] Recent phytochemical investigations have traced the piscicidal, oral ‘local anesthetic’ and saliva-producing (sialogogic) properties of this species to the isobutyl-amide, piperovatine. [15] This compound induces dramatic increases in intracellular calcium concentration.…”