Anti-inflammatory effects, nuclear magnetic resonance identification, and high-performance liquid chromatography isolation of the total flavonoids from Artemisia frigida

Abstract

The aerial parts of Artemisia frigida Willd. are used to treat joint swelling, renal heat, abnormal menstruation, and sore carbuncle. The anti-inflammatory effects of A. frigida have been well-known in folk medicine, suggesting that components extracted from A. frigida could potentially treat inflammatory disease. With the aim of discovering bioactive compounds, in this study, we extracted total flavonoids from the aerial parts of A. frigida and investigated their anti-inflammatory effects against inflammation induced by carrageenan and egg albumin in rats. At the doses studied, total flavonoids (100 mg/kg, 200 mg/kg, and 400 mg/kg) and some isolated compounds (30 mg/kg) showed significant and dose-dependent anti-inflammatory effects. According to the high-performance liquid chromatography analysis of the total flavonoids from A. frigida, there are five major compounds, namely, 5-hydroxy-3',4'-dimethoxy-7-O-β-d-glucuronide (F1), 5-hydroxy-3',4',5'-trimethoxy-7-O-β-d-glucuronide (F2), 5,7,3'-trihydroxy-6,4'-dimethoxyflavone (F3), 5,3'-dihydroxy-6,7,4'-trimethoxyflavone (F4), and 5,3'-dihydroxy-3,6,7,4'-tetramethoxyflavone (F5), which may explain the anti-inflammatory activity.

Bioactive Phenolics of the Genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS Profile of the Siberian Species and Their Inhibitory Potential Against α-Amylase and α-Glucosidase

“…Compound 92 , from A. sericea with UV maxima at 272 and 343 nm, gave as MS fragment with m / z 329 [M–H] − and two demethylated ions with m / z 314 and 299, indicating the existence of two CH 3 groups. It was identified with 5,7,3′-trihydroxy-6,4′-dimetoxyflavone, which was reported as A. frigida previously (Wang Q. et al, 2016 ). Flavone aglycone 96 gave an [M–H] − ion with m / z 343 and fragments with m / z 328, 313 and 298, caused by elimination of three methyl-groups, and was determined to be 5,4′-dihydroxy-6,7,3′-trimetoxyflavone, also found in A. frigida (Wang Q. et al, 2016 ).…”

“…It was identified with 5,7,3′-trihydroxy-6,4′-dimetoxyflavone, which was reported as A. frigida previously (Wang Q. et al, 2016 ). Flavone aglycone 96 gave an [M–H] − ion with m / z 343 and fragments with m / z 328, 313 and 298, caused by elimination of three methyl-groups, and was determined to be 5,4′-dihydroxy-6,7,3′-trimetoxyflavone, also found in A. frigida (Wang Q. et al, 2016 ). Compounds 101 from A. messerschmidtiana and 108 from A. palustris were provisionally identified as 6-hydroxyluteolin-dimethyl ester and 6-hydroxyluteolin-trimethyl ester, due to their UV-patterns and MS fragmentation ( m / z 329 → 314 → 299 for 101 ; m / z 357 → 342 → 327 → 312 for 108 ).…”

“…Scutellarein-7- O -glucoside ( 63 ) and hispidulin-7- O -glucoside, or homoplantaginin ( 69 ), from A. latifolia and nepetin-7- O -glucoside or nepetrin ( 72 ) from A. messerschmidtiana were identified with standards. Compound 68 from A. sericea , with UV maxima at 251, 267 and 346 nm and MS fragments with m / z 505 [M-H] − and 329 [(M–GlcA)–H] − , was determined as 5,7,3′-trihydroxy-6,4′-dimetoxyflavone-7- O -glucuronide that has already been found in that species (Wang Q. et al, 2016 ).…”

“…A. sericea was the only species capable of concentrating flavone glycosides of various types, such as the glycosides of apigenin, luteolin, 6-hydroxyluteoline and others detected. This species relates to the subsection Frigidae (section Absinthium) together with A. frigida , known for its ability to biosynthesize flavones (Wang Q. et al, 2016 ). A. anethifolia , in particular, was distinguished from the other studied Artemisia species, which selectively accumulated chrysoeriol glycosides ( 34 , 61 , 67 ).…”

Chemical composition and anti-inflammatory effects of the EtOAc extract from Capsella bursa-pastoris (L.) Medic.

“…distilled water (10 ml/kg). All animals were observed for 72 h after drug administration (Wang et al, 2016).…”