A Naphthoquinone from Sinningia canescens Inhibits Inflammation and Fever in Mice

Abstract

We previously showed that plants from the genus Sinningia are a source of antiinflammatory and analgesic compounds with different mechanisms of action. The present study evaluated the antiinflammatory, antinociceptive, and antipyretic effects of a crude extract (CE) from Sinningia canescens, its fractions, and 6-methoxy-7-hydroxy-α-dunnione (MHD) in mice. These effects were evaluated using carrageenan (Cg)-induced paw edema, acetic acid- and formalin-induced nociception, mechanical hyperalgesia, lipopolysaccharide (LPS)-induced fever, and plasma cytokine levels. The CE and dichloromethane and hexane fractions reduced Cg-induced paw edema and hyperalgesia, LPS-induced fever, and plasma tumor necrosis factor-α (TNF-α) levels. The CE also reduced acetic acid-induced writhing and the second phase of formalin-induced nociception but did not alter thermal nociception or motor performance. Partition with solvents showed that the antiinflammatory, antihyperalgesic, and antipyretic activities were present in dichoromethane and hexane fractions, and the major compound isolated from these fractions was MHD. Oral and intraplantar MHD administration reduced paw edema. Oral MHD administration also reduced prostaglandin E-induced hyperalgesia but did not alter hyperalgesia that was induced by dopamine and dibutyryl cyclic adenosine monophosphate. Treatment with glibenclamide, a K channel blocker, did not alter the analgesic effect of MHD. Lipopolysaccharide-induced fever and TNF-α, interleukin-1β, and interleukin-6 levels were inhibited by MHD. Altogether, these data suggest that the CE has antiinflammatory, analgesic, and antipyretic activity, and these actions are at least partially related to MHD. These results also suggest that MHD acts by blocking cytokine synthesis and/or blocking prostaglandin activity.

Hypothermic Effect of Acute Citral Treatment during LPS-induced Systemic Inflammation in Obese Mice: Reduction of Serum TNF-α and Leptin Levels

“…In the present study, we elucidated the thermoregulatory responses during SI after LPS injection in eutrophic and obese mice. Previous studies have described that the LPS-induced thermoregulatory response is modulated by two variables: the dose of the inductor agent and ambient temperature [ 30 , 51 , 52 ]. Firstly, the dose of the inductor agent can promote distinct responses, such as fever at low doses (0.5–100 µg/kg), and hypothermia, followed by fever at high doses (1–10 mg/kg) of LPS [ 30 ].…”

CHEMICAL CONSTITUENTS OF Sinningia mauroana AND SCREENING OF ITS EXTRACTS FOR ANTIMICROBIAL, ANTIOXIDANT AND CYTOTOXIC ACTIVITIES

“…Again, these results are consistent with the compounds isolated from each extract. Jacaranone (13), obtained from EtOAc extract, showed antioxidant capacity in a previous study. 36 The presence of phenolic glycosides (14-15) and flavonoids (16)(17) justify the higher antioxidant activity of EtOH extract.…”

“…The 13 C NMR data of 11 and 12 are very similar in both used solvents, with deuterated acetone causing small deshield effects (Tables 1 and 2, Figures 23S, 29S and 32S). For identification purpose, it is important note that hydrogenated aromatic carbons Figure 1.…”

“…Optical density was measured using a Synergy 2 (Bio-Tek) spectrophotometer. Onedimensional ( 1 H, 13 C) and two-dimensional (gHSQC, gHMBC) NMR spectra were recorded on Brucker spectrometers (AC 200, Avance 400, and or Avance 600) observing 1 H at 200, 400, or 600 MHz, and 13 C at 50, 100 or 150 MHz. Deuterated acetone (acetone-d 6 ), chloroform (CDCl 3 ) or methanol (MeOH-d 4 ) were used as solvents, and the chemical shifts are given in ppm (d), with coupling constants (J) in Hz.…”

“…3 Finally, the naphthoquinone 7-hydroxy-6-methyoxy-a-dunnione, obtained of S. canescens, S. leucotricha and S. hatschbachii, displayed anti-inflammatory and antipyretic activities. 13 Therefore, Sinningia species are a still not fully exploited source of compounds with biological activity.…”