Anti-inflammatory effects and structure elucidation of flavonoid and biflavonoid glycosides from Artemisia frigida Willd

Caffeoylquinic Acids and Flavonoids of Fringed Sagewort (Artemisia frigida Willd.): HPLC-DAD-ESI-QQQ-MS Profile, HPLC-DAD Quantification, in Vitro Digestion Stability, and Antioxidant Capacity

“…Nineteen flavonoid aglycones (41–59) as flavone and flavonol derivatives were found, and 12 substances were identified according to their chromatographic behaviour and UV and mass spectra, in comparison with reference standards (Figure 2, Table 2). As a result, the known A. frigida aglycoses tricin (41), apigenin (42), hispidulin (43) [4], jaceosidine (45) [13,20], chrysoeriol (47) [13], luteolin-3′,4′-dimethyl ether (50) [4], and eupatorin (51) [15,16,18] were detected. Acacetin (54), cirsimaritin (55), cirsilineol (56), velutin (57) and genkwanin (59) were found for the first time in A. frigida .…”

“…Previously, 46 was isolated from A. frigida only in the form of 7- O -glucuronide-4′- O -glucoside, named friginoside E [17], therefore, this aglycone was found in plants for the first time. Compound 49 has UV and mass spectra typical of dimethoxylated flavones ( m / z 329, 315, 301) [15], which allowed its structure to be identified as 5,7,3′-trihydroxy-6,4′-dimethoxyflavone, the known flavone of A. frigida [15,16,18]. Flavone 5,7,3′,4′-tetrahydroxy-6,5′-dimethoxyflavone (52; m / z 345 (M–H) − ) and flavonol quercetagetin-3,6,3′,4′-tetramethyl ether (53; m / z 373 (M–H) − ) discovered in the chloroform fraction were also previously found in A. frigida [13].…”

“…Chemical investigations of Artemisia species often focus on artemisinin and other sesquiterpenes, ignoring phenolic compounds despite their well-known potent antioxidant properties [11]. According to literature data, a chemical study of phenolic compounds was carried out on A. frigida growing in North America [12,13], China [14,15,16,17], Inner Mongolia [18,19] and Russia [20]. As a result, only 37 substances, such as flavonoids of the flavone, flavonol and biflavone groups; coumarins and phenylpropanoids, were isolated and characterized (Table S2).…”

“…Derivatives of luteolin, 6-hydroxyluteolin and 3′,5′-demethoxytricin in the form of aglycones and glycosides are the main structural types of flavones in A. frigida . Rare O -glucuronides and 2′′- O -glucuronyl-glucuronides were detected only in raw materials collected in China and Inner Mongolia [17,18,19]. In specimens of Russian origin, only C -glycosides of apigenin were found [20], and luteolin-7- O -glucoside (cynaroside) was revealed in North American samples [12,13].…”

“…In specimens of Russian origin, only C -glycosides of apigenin were found [20], and luteolin-7- O -glucoside (cynaroside) was revealed in North American samples [12,13]. The only biflavone glycoside (8- O -8′′′-biluteolin-7,7′′′- O -glucuronide) was detected in the aerial part of A. frigida from the vicinity of the Tongliao district (China) [18]. North American samples of A. frigida were characterized by the ability to accumulate derivatives of luteolin and heptahydroxyflavone, whereas the glycosides of tricetin were found in specimens from China and Mongolia.…”