Kramecyne — A New Anti-inflammatory Compound Isolated from Krameria cytisoides

Abstract

In the present work we describe the structure and anti-inflammatory activity of a new compound, kramecyne, isolated from a methanol extract of Krameria cytisoides (Krameriaceae). The structure of kramecyne was determined by IR, NMR, MS, and elemental analysis, which indicated that the structure corresponded to a hexamer of cyclic peroxide monomers. This compound exhibited good anti-inflammatory activity in the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema (51.8 ± 6.9% inhibition) and carrageenan-induced rat paw edema models at doses of 50 mg/kg. The compound significantly reduced edema to 63.1% after 1.0 h, and the effect was unchanged for 5 h. Kramecyne did not present acute toxicity, even at doses of 5,000 mg/kg.

Effect of Kramecyne on the Inflammatory Response in Lipopolysaccharide-Stimulated Peritoneal Macrophages

“…It has been observed that kramecyne does not exhibit toxic effects even at a dose of 5000 mg/kg in a model of acute toxicity [9]. Taken together with the cells viability studies, these results support the low toxicity of kramecyne and encourage the possibility of using it as anti-inflammatory.…”

“…The compound was identified as kramecyne with FTIR ν  cm −1 (solid) 3332 (O–H), 2919 and 2486 (C–H), 1608 (skeleton), 1443 (C–C), 1284, 1108 (C–O), and 800 (O–O) 1 H-NMR (500 MHz, methanol-d 4 ): δ 3.61, d(11.47), 3.63, d(11.47), 3.628, d(11.50), 3.668, d(11.50), 3.69, m, 3.74, dd (3.19). 13 C-NMR (500 MHz, methanol-d 4 ): δδ 62.12 (CH 2 ), 62.85 (CH 2 ), 63.40 (CH 2 ), 75.15 (C), 73.17 (CH) [9]. …”

“…For these reasons, researchers on new compounds with anti-inflammatory activity and natural products are an important source with fewer adverse effects. Recently the novel compound kramecyne was isolated from Krameria cytisoides and showed anti-inflammatory activities in ear edema induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and paw edema induced by carrageenan [9]. …”

Effects of Kramecyne on LPS Induced Chronic Inflammation and Gastric Ulcers

“…In this study, the effects of KACY on LPS‐induced systemic chronic inflammation and its gastroprotective activities were investigated with KACY dosed at 50 mg/kg po,. a dose selected on the basis of previous studies because in the rat carrageenan‐induced paw edema models where there was no difference between KACY tested at 50 and 100 mg/kg or a higher dose [Pérez‐Gutiérrez et al, ].…”

“…This compound had an LD 50 > mg/kg p.o., exerted in vivo anti‐inflammatory effects at 50 and 100 mg/kg .pp. [Pérez‐Gutiérrez et al, ; Alonso‐Castro et al, ], and in vitro at 31.25–250 µg/ml [Sánchez‐Miranda et al, ]. It also has antinociceptive activities [Alonso‐Castro et al, ].…”