Chemical and Biological Properties of Quinochalcone  C-Glycosides from the Florets of Carthamus tinctorius

Yue, Shi‐Jun; Tang, Yuping; Li, Shujiao; Duan, Jin‐Ao

doi:10.3390/molecules181215220

Cited by 94 publications

(66 citation statements)

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“…We studied earlier the fatty-acid composition of fatty oil from seeds of C. tinctorius [3]. However, the flowers of this plant, which have antioxidant, hepatoprotective, anti-inflammatory, neurotropic, and other properties, are also interesting as a source of drugs [4]. In our opinion, the flavonoids are of interest with respect to the manifestation of antioxidant and hepatoprotective activity by C. tinctorius flowers.…”

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“…In our opinion, the flavonoids are of interest with respect to the manifestation of antioxidant and hepatoprotective activity by C. tinctorius flowers. According to the literature [4][5][6][7], flowers of this plant contain acacetin, luteolin, quercetin,…”

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confidence: 99%

“…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].…”

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Flavonoids of Carthamus tinctorius Flowers

Куркин

Kharisova

2014

Chem Nat Compd

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Flavonoids of Carthamus tinctorius Flowers

Куркин

Kharisova

2014

Chem Nat Compd

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“…The eastern part of the Mediterranean region is regarded as the original centre of this genus. The genus includes about 25 species, distributed from Spain and North Africa across the Middle East to northern India (Ashri, 1960;Yue et al, 2013). The oil of Carthamus tinctorius plant from Carthamus species is found suitable for biodiesel manufacturing and used as an industrial good.…”

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Amino Acids Sequence Based in Silico Analysis of RuBisCO (Ribulose-1,5 Bisphosphate Carboxylase Oxygenase) Proteins in Some Carthamus L. ssp.

Sevindik¹

2017

Not Sci Biol

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RuBisCO is an important enzyme for plants to photosynthesize and balance carbon dioxide in the atmosphere. This study aimed to perform sequence, physicochemical, phylogenetic and 3D (three-dimensional) comparative analyses of RuBisCO proteins in the Carthamus ssp. using various bioinformatics tools. The sequence lengths of the RuBisCO proteins were between 166 and 477 amino acids. Their molecular weights (Mw) ranged from 18,711.47 to 52,843.09 Da; the most acidic and basic protein sequences were detected in C. tinctorius (pI = 5.99) and in C. tenuis (pI = 6.92), respectively. The extinction coefficients of RuBisCO proteins at 280 nm ranged from 17,670 to 69,830 M -1 cm -1 , the instability index (II) values for RuBisCO proteins ranged from 33.31 to 39.39, while the GRAVY values of RuBisCO proteins ranged from -0.313 to -0.250. The most abundant amino acid in the RuBisCO protein was Gly (9.7%), while the least amino acid ratio was Trp (1.6 %). The putative phosphorylation sites of RuBisCO proteins were determined by NetPhos 2.0. Phylogenetic analysis revealed that RuBisCO proteins formed two main clades. A RAMPAGE analysis revealed that 96.3%-97.6% of residues were located in the favoured region of RuBisCO proteins. To predict the three dimensional (3D) structure of the RuBisCO proteins PyMOL was used. The results of the current study provide insights into fundamental characteristic of RuBisCO proteins in Carthamus ssp.

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“…Thus, caftaric acid and tricin in addition to caffeic acid, luteolin, cinaroside, and taraxasterol that were already known from this plant were isolated and characterized for the first time during the study of the constituent composition of the aerial part of T. officinale. Compounds 4 and 5, identified as 5,7,3c,4c-tetrahydroxyflavone (luteolin) and 5,7,3c,4c-tetrahydroxyflavone 7-O-E-D-glucopyranoside (cinaroside) [8,9], and compound 6, identified as taraxasterol [10], were isolated previously from the aerial part of T. officinale [3]. …”

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Constituents of the Aerial Part of Taraxacum officinale

Куркин

Aznagulova

2016

Chem Nat Compd

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Roots of Taraxacum officinale F.H. Wigg. (Asteraceae) are registered in Russia as pharmacopoeial plant raw material and are used mainly as an appetite stimulant [1][2][3]. The herb of this plant is used in folk medicine as a diuretic, cholagogic, anti-inflammatory, and immunomodulating agent and as an ingredient of several foreign formulations (Tonsilgon, Aristochol, etc.) [2,3].According to the literature [3], roots and the aerial part of T. officinale contain flavonoids (luteolin, cinaroside, luteolin 7-rhamnosylglucoside) and phenylpropanoids or hydroxycinnamic acid and their derivatives (p-coumaric, caffeic, ferulic, chlorogenic, and chicoric acids), triterpene saponins (taraxasterol etc.), sterols (E-sitosterol etc.), and many other primary and secondary metabolites.The goal of the present work was to study the constituent composition of the aerial part of T. officinale collected in May 2015 in the vicinity of Samara.Six pure compounds including phenylpropanoids (1 and 2), flavonoids (3-5), and triterpene saponins (6) were isolated by column chromatography over Polyamide Woelm and L 40/100 silica gel followed by rechromatography.PMR spectra of 1 showed resonances for aromatic protons H-2 at 7.08 (d, J = 2 Hz), H-6 at 7.03 (dd, J = 9, 2 Hz), and H-5 at 6.76 (d, J = 9 Hz). This in combination with resonances for H-7 at 7.48 (d, J = 16 Hz) and H-8 at 6.30 (d, J = 16 Hz) in addition to mass spectral data (peak with m/z 180) and the UV spectrum were consistent with a caffeic acid in the molecule. Furthermore, PMR spectra had resonances at 5.53 (s, H-2c) and 3.65 (s, H-3c) for tartaric acid. This identified 1 as a 2-caffeoyltartaric acid (caftaric acid), which is very common in Asteraceae plants [4,5]. The structure of caftaric acid was also confirmed by its 13 C NMR spectra [4,5].Caftaric Acid (2c-caffeoyltartaric acid) (1). Light-yellow amorphous compound, Ñ 13 Í 12 Î 9 . UV spectrum (EtOH, O max , nm): 217, 243, 290 sh, 328. Mass spectrum (70 eV, 200qÑ, m/z, %): Compound 2 formed yellow crystals, C 9 H 8 O 4 , mp 217-220°C (aq. EtOH). UV, PMR, and mass spectra identified it as caffeic acid [6]. Tricin (5,7,4c-trihydroxy-3c,5c-dimethoxyflavone) (3). Yellow needles, Ñ 17 Í 14 Î 7 , mp 279-281qÑ (C 2 H 5 OH aq.). UV spectrum (EtOH, O max , nm): 270, 351; +NàÎÀñ 275, 385; + NaOAc + H 3 BO 3 270, 352; +AlCl 3 and AlCl 3 + HCl 278, 364, 395. Mass spectrum (70 eV, 200qÑ, m/z, %): 330 (Ì + , 100). 1 Í NMR spectrum (300 MHz, DMSO-d 6 , G, ppm, J/Hz): 12.97 (1H, s, 5-ÎÍ), 7.33 (2Í, s, Í-2c, 6c), 6.99 (s, Í-3), 6.57 (d, J = 2, Í-8), 6.22 (d, J = 2, Í-6), 3.80 (6Í, s, 2ÎÑÍ 3 ).Flavonoid 3 acted like an aglycon and was identified as tricin by UV, PMR, and mass spectra [7]. Thus, caftaric acid and tricin in addition to caffeic acid, luteolin, cinaroside, and taraxasterol that were already known from this plant were isolated and characterized for the first time during the study of the constituent composition of the aerial part of T. officinale. Compounds 4 and 5, identified as 5,7,3c,4c-tetrahydroxyflavone (luteolin) and 5,7,...

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Chemical and Biological Properties of Quinochalcone C-Glycosides from the Florets of Carthamus tinctorius

Cited by 94 publications

References 100 publications

Flavonoids of Carthamus tinctorius Flowers

Flavonoids of Carthamus tinctorius Flowers

Amino Acids Sequence Based in Silico Analysis of RuBisCO (Ribulose-1,5 Bisphosphate Carboxylase Oxygenase) Proteins in Some Carthamus L. ssp.

Constituents of the Aerial Part of Taraxacum officinale

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