Flavonoids fromTrifolium trichocephalum

Shalashvili, K. G.; Кемертелидзе, Э. П.

doi:10.1007/bf00567715

Cited by 2 publications

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“…is a perennial species growing at eastern regions of Turkey [1]. Luteolin 3'-O-D-glucoside, luteolin 7-O-D-glucoside, and luteolin were reported to be isolated from T. trichocephalum previously [12]. Since chemical content of plant species grown in different geographic locations may show variability, phytochemical properties of T. trichocephalum have been decided to be re-investigated in the current study.…”

Section: Previous Studiesmentioning

confidence: 99%

Flavonoid Derivatives from the Aerial Parts of Trifolium trichocephalum M. Bieb. and Their Antioxidant and Cytotoxic Activity

Renda¹,

Özgen²,

Ünal³

et al. 2017

Rec.Nat.Prod.

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Trifolium L. species with a rich isoflavone content have been used as expectorant, analgesic, antiseptic, tonic, and wound-healer in folk medicine. The aim of the study is to evaluate pharmacological properties of the extracts and isolated compounds of T. tricocephalum. Phytochemical investigation of the aerial parts of T. trichocephalum led to the isolation of daidzein, genistein, quercetin, and daidzein 4'-O-β-glucoside for the first time from this species. Isolated compounds along with the methanol extract, water, ethyl acetate and chloroform subextracts were tested for their radical scavenging and cytotoxic activity which was evaluated by MTT assay. According to the results of activity tests, extracts showed a concentration-dependent radical scavenging activity as well as cytotoxic effect on HepG2 cells at 400 μg/mL, whereas the compounds did not exert any obvious cytotoxic effect at tested concentrations.

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Section: Previous Studiesmentioning

confidence: 99%

Flavonoid Derivatives from the Aerial Parts of Trifolium trichocephalum M. Bieb. and Their Antioxidant and Cytotoxic Activity

Renda¹,

Özgen²,

Ünal³

et al. 2017

Rec.Nat.Prod.

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“…The physicochemical properties of the aglycon and its acetyl derivative were compared with an authentic sample of luteolin and identified the aglycon as 5,7,3′,4′-tetrahydroxyflavone, luteolin [5].…”

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confidence: 99%

Luteolin diglucuronide from Perilla nankinensis

et al. 2006

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We have previously reported the isolation of flavonoids from leaves of Perilla nankinensis and established the structure of apigenin diglucuronide [1]. In continuation of the separation of the total extracts, we isolated glycoside 1, a finely crystalline light yellow powder, mp 184-186°C (dec.), [α] D 20 -32.5° (c 0.05, MeOH), [M] + 639, C 27 H 26 O 18 .The UV spectrum of 1 (λ max 268 and 336 nm) is typical of flavones, as is the IR spectrum (KBr, ν max , cm -1 ): 3250 (OH) and 1656 (γ-pyrone C=O). However, there is an absorption band in the IR spectrum that is characteristic of carboxylic acids at 1740 cm -1 in addition to that at 1650-1630 cm -1 .The PMR spectrum contains signals for 9 aromatic and 10 sugar protons [2]. These include the C-3 proton that is observed as a singlet at 6.83 ppm, the chelate hydroxyl (5-OH) at / 12.97 ppm, and two hydroxyls at 9.88 and 9.37 ppm (4′-OH and 3′-OH), respectively (Table 1). Signals at 6.05 and 5.56 ppm with SSCC 7.5 Hz each are consistent with the presence of two anomeric protons.The absorption band at 1740 cm -1 in the IR spectrum is consistent with glucuronic acid in the flavone. Furthermore, a 1H doublet at 4.94 and 4.75 ppm (J = 9.0 Hz each) is characteristic of H-5″ and H-5′″ of D-glucuronic acid [3].Hydrolysis of 1 [4] gives an aglycon of formula C 15 H 10 O 6 with mp 342-344°C and D-glucuronic acid. Judging from the yield of genin (~53%) and the PMR data for the glycoside, there should be at least two molecules of glucuronic acid.The physicochemical properties of the aglycon and its acetyl derivative were compared with an authentic sample of luteolin and identified the aglycon as 5,7,3′,4′-tetrahydroxyflavone, luteolin [5].

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Flavonoids fromTrifolium trichocephalum

Cited by 2 publications

References 0 publications

Flavonoid Derivatives from the Aerial Parts of Trifolium trichocephalum M. Bieb. and Their Antioxidant and Cytotoxic Activity

Flavonoid Derivatives from the Aerial Parts of Trifolium trichocephalum M. Bieb. and Their Antioxidant and Cytotoxic Activity

Luteolin diglucuronide from Perilla nankinensis

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