Flavonoids from Tanacetum vulgare flowers

Abstract

Flowers of tansy (Tanacetum vulgare L.) are used in various medicinal forms as antihelminthic and cholegogic agents [1][2][3][4][5]. The pharmacological properties of tansy flower preparations are due mainly to the essential oil (thujone and other terpenoids) and flavonoids. According to various literature sources [3][4][5], apigenin, acacetin, luteolin, cinaroside, eupatilin, jaceidin, and jaceoside are the main flavonoids in tansy flowers. However, reports in the domestic and foreign literature are somewhat contradictory.The goal of the present work was to study the flavonoid composition of tansy flowers growing in Samara Oblast (Russia).We studied tansy flowers collected near Nizhnee Sancheleevo village, Samara Oblast (July, 2008). Flowers (150 g) were extracted exhaustively with EtOH (70%) by combining maceration (24 h) with subsequent thermal extraction at 85-90°C. The aqueous alcohol extracts were evaporated in vacuo to a thick residue (~50 mL). The condensed extract was dried over L 40/100 silica gel. The resulting powder (extract + silica gel) was placed on a layer of silica gel that was formed in CHCl 3 and eluted by CHCl 3 and CHCl 3 :EtOH in various ratios (97:3, 95:5, 93:7, 90:10, 88:12, 85:15, 80:20, 70:30). The separation of the compounds was monitored by TLC on Silufol UV 254 and Sorbfil PTSKh-AF-A-UV plates using CHCl 3 :EtOH (4:1) and CHCl 3 :MeOH:H 2 O (26:14:3).Fractions containing the dominant compound 1 were combined. The precipitate that formed in these was separated and recrystallized from EtOH to afford 1 in 0.2% yield of the air-dried raw material mass. Fractions containing compounds 2-4 (each separately) were transferred to a chromatographic column (sorbent height 4.0 cm; diameter, 5 cm). The respective chromatographic column was eluted by H 2 O and aqueous EtOH (20%, 40, 70, and 96). Purification over polyamide columns afforded 2 (96% EtOH eluent), 3 (40% EtOH eluent), and 4 (70% EtOH eluent). The compounds were purified additionally by recrystallization from aqueous EtOH.The chemical structures of flavonoids 1-4 were elucidated using PMR and UV spectroscopy and mass spectrometry in addition to chemical transformations. Flavonoids 1 and 3 were cleaved by acid hydrolysis (10% HCl, 100°C, 2 h) and E-glucosidase (Fluka, Hungary) into glucose and the aglycons, which were identified by TLC as acacetin (5,7-dihydroxy-4c-methoxyflavone) (2) and apigenin (5,7,4c-trihydroxyflavone) (4), respectively. Flavonoids 2 and 4 were also isolated from tansy raw material in the free state. The PMR spectrum of 1 showed two 2H doublets at 8.07 and 7.14 ppm with SSCC (J) 9 Hz that were assigned to H-2c,6c and H-3c,5c, respectively; two 1H doublets at 6.84 and 6.45 ppm with J = 2.5 Hz that were characteristic of ring A protons (H-8 and H-6), and a singlet for H-3 at 6.95 (flavone compound). A 3H singlet at 3.87 for the C-4c OCH 3 group and a singlet for the 5-OH of the flavonoid were observed in the PMR spectrum. The carbohydrate was placed on the 7-OH group on the basis of these results and those from enzyma...

Cytotoxic Effect of Eudesmanolides Isolated from Flowers of Tanacetum vulgare ssp. siculum

“…It is widely used in folk medicine and the crude toxic Tanaceti flos, described for years in some Western pharmacopoeias, has been employed as a vermifuge, emenagogue [ 5 ] and anti-inflammatory treatment [ 6 ]. T. vulgare shows also remarkable antioxidant properties, mainly due to its phenolic compounds content [ 7 ], in fact it is particularly rich in flavonoids [ 8 ], along with 3,5-dicaffeoylquinic acid, showing antiviral activity against the herpes simplex viruses HSV-1 and HSV-2 [ 9 ].…”

Flavonoids of Carthamus tinctorius Flowers

“…Compounds 4 and 5 were identified as 5,7,3c,4c-tetrahydroxyflavone (luteolin) and 5,7,3c,4c-tetrahydroxyflavone 7-O-E-D-glucopyranoside (cinaroside) [11], which were isolated previously from C. tinctorius flowers [4].…”

Phytochemical Constituents of Aquilaria malaccensis Leaf Extract and Their Anti-Inflammatory Activity against LPS/IFN-γ-Stimulated RAW 264.7 Cell Line

“…The UV absorption peaks appeared at 268 and 335 nm, meanwhile IR bands corresponding to OH (3252 cm –1 ) and C=O (1663 cm –1 ) are similar to compounds 2 , 3 , and 4 which suggests a flavonoid nucleus. 44 Table 2 demonstrates the 1 H and 13 C NMR data of compound 5 , while Figure 2 illustrates the 2D NMR correlations. Thus, compound 5 was identified as acacetin, and its spectroscopic data are identical with those obtained by.…”

“…The UV absorption peaks appeared at 268 and 335 nm, meanwhile IR bands corresponding to OH (3252 cm −1 ) and CO (1663 cm −1 ) are similar to compounds 2, 3, and 4 which suggests a flavonoid nucleus. 44 Table 1. 1 H (CDCl 3 , 500 MHz) and 13 2 illustrates the 2D NMR correlations.…”