29702-25-8Relevant academic research and scientific papers
C-Glycosyl Flavones from Two Eastern Siberian Species of Silene
Olennikov,Chirikova
, p. 642 - 647 (2019)
Flavonoids from Silene aprica Turcz. and S. samojedorum (Sambuk) Oxelman (Caryophyllaceae) growing in Baikal region were studied for the first time. A total of 14 compounds including three new compounds 1–3 were isolated. Their structures were established using UV, IR, and NMR spectroscopy and mass spectrometry. Apigenin-6-C-(2″-O-α-L-arabinopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside A, 1) and apigenin-6-C-(2″-O-β-D-glucopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside B, 2) were observed in S. aprica; 1 and luteolin-6-C-(2″-O-α-L-arabinopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside C, 3), in S. samojedorum.
Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers
Dou, Mian,He, Xi-Hui,Sun, Yan,Peng, Fang,Liu, Jiang-Yun,Hao, Li-Li,Yang, Shi-Lin
, p. 255 - 258 (2015)
Acid hydrolysis mechanisms of orientin-2″-O-galactopyranoside (OGA), orientin and other flavone C-glycosides in the trollflowers (Trollius chinensis Bunge) were studied in this report for the first time. Hydrolysis parameters including temperature, acidity, solvent and reaction time were comprehensively investigated. OGA could be hydrolyzed to orientin, followed by an isomerization to isoorientin via a reversible Wessely-Moser rearrangement reaction under stronger acidic conditions. A first-order kinetic model fitted the hydrolysis process of OGA well. Under the optimal hydrolysis conditions of 80 °C, 1.0 mol/L H+ and 7 h reaction time, about 77% OGA was transformed to orientin with no detectable isoorientin. These results could be helpful for better understanding of the acid hydrolysis kinetics of flavone C-glycosides, as well as the preparation of these valuable components under controlled acid hydrolysis conditions.
Polyphenols from Erythrina crista-galli: Structures, molecular docking and phytoestrogenic activity
Ashmawy, Naglaa S.,Ashour, Mohamed L.,Wink, Michael,El-Shazly, Mohamed,Chang, Fang-Rong,Swilam, Noha,Abdel-Naim, Ashraf B.,Ayoub, Nahla
, (2016)
Objectives: The current study aimed at exploring the secondary metabolites content of Erythrina crista-galli aqueous methanol extract and assessing its phytoestrogenic and cytoprotective activities. Methods: Isolation of the compounds was carried out using conventional chromatographic techniques. The structures of the isolated compounds were elucidated based on the UV, NMR spectral data along with their mass-spectrometric analyses. The phytoestrogenic activity was evaluated in-silico and in vitro using the Arabidopsis thaliana pER8: GUS reporter assay and the proliferation-enhancing activity of MCF-7 cells. Key findings: Phytochemical investigation of E. crista-galli aqueous methanol extract resulted in the isolation and identification of five flavonoids. The plant extract and its fractions showed significant estrogenic activities compared to controls. Conclusion: Five flavonoids were identified from E. crista-galli aqueous methanol extract. To the best of our knowledge, among these flavonoids, apigenin-7-O-rhamnosyl-6-C-glucoside was isolated for the first time from nature. Moreover, luteolin-6-C-glucoside was isolated for the first time from this plant. The plant revealed promising phytoestrogenic activities. This gives rationale to some of its pharmacological properties and suggests additional phytoestrogenic effects, which have not been reported yet.
Flavonoid pattern inheritance in the allopolyploid Spartina anglica – Comparison with the parental species S. maritima and S. alterniflora
Grignon-Dubois, Micheline,De Montaudouin, Xavier,Rezzonico, Bernadette
, (2020/03/27)
The invasive species Spartina anglica arose in Europe by a cross between the Afro-European species S. maritima (native, paternal ancestor) and the introduced North American S. alterniflora (invasive, maternal ancestor). Aqueous methanolic extracts were prepared from plant tissue for chemotaxonomical comparison between the three species and determination of the phenolic pattern inheritance in S. anglica. A total of 20 phenolic compounds were detected in the aerial tissues of S. anglica and S. alterniflora, but only seven in S. maritima. They were isolated from their respective crude extracts, and their structures were determined according to spectroscopic data analysis and chemical evidence. They all belong to the flavonoid class, with 13 of them identified as C-glycoflavonoid and seven as O-glycoflavonoid. All these products were detected for the first time from S. anglica, fourteen of them for the first time from S. alterniflora, and three of them for the first time from S. maritima. The individual concentrations in the three species were determined by quantitative HPLC. The two parental species were found to differ markedly in their foliar phenolic fingerprint, whereas that of S. anglica showed a clear maternal dominance. Eight of the fourteen major compounds identified were of maternal origin among which, six were over-expressed, only three were from paternal origin but under-regulated, while two originated from the two parents. As far as we know, this work represents the first exhaustive report of the phenolic fingerprints of S. alterniflora and S. anglica and of the phenolic pattern inheritance in S. anglica. The similarity in the phenolic chemistry of the introduced and invasive S. alterniflora to its progeny could play a role in the physiological vigour and invasion success of S. anglica. This work provide a foundation for further studies, considering the reported biological activities of C-glycosidic flavonoids and tricin derivatives, and the lack of knowledge of the ecological chemistry of the genus Spartina.
New C,O-Glycosylflavones from Melandrium divaricatum
Olennikov,Chirikova
, p. 1032 - 1038 (2019/11/26)
The aerial part of Melandrium divaricatum Fenzl (Caryophyllaceae) afforded 11 glycosylflavones including two new compounds that were characterized using UV, IR, and NMR spectroscopy and mass spectrometry as apigenin-6-C-(2″ -O-α-L-rhamnopyranosyl)-β-D-glucopyranoside-7-O-(6″″ -O-feruloyl)-β-Dglucopyranoside (divarioside A, 1) and apigenin-6-C-(2″-O-D-glucopyranosyl)- β-D-glucopyranoside-7-O-(6″″-O-feruloyl)- β-D-glucopyranoside (divarioside B, 2).
Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins
Hao,Caulfield,Hamilton,Pickett,Midega,Khan,Wang,Hooper
, p. 73 - 87 (2016/04/06)
The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus.
Flavonol glycosides with α-Glucosidase inhibitory activities and new flavone C-diosides from the leaves of machilus konishii
Lin, Yi-Shan,Lee, Shoei-Sheng
, p. 1672 - 1682 (2015/02/19)
Seventeen flavonoids, five of which are flavone C-diosides, 1 - 5, were isolated from the BuOH- And AcOEt-soluble fractions of the leaf extract of Machilus konishii. Among 1 - 5, apigenin 6-C- β -dxylopyranosyl- 2 -O- β -d-glucopyranoside (2), apigenin 8-C-α-l-arabinopyranosyl-2 -O- β -d-glucopyranoside (4), and apigenin 8-C- β -d-xylopyranosyl-2 -O- β -d-glucopyranoside (5) are new. Both 4 and 5 are present as rotamer pairs. The structures of the new compounds were elucidated on the basis of NMRspectroscopic analyses and MS data. In addition, the 1H- And 13C-NMR data of apigenin 6-C- α -larabinopyranosyl- 2 -O- β -d-glucopyranoside (3) were assigned for the first time. The isolated compounds were assayed against a-glucosidase (type IV from Bacillus stearothermophilus). Kaempferol 3-O- (2-β-d-apiofuranosyl)- α -l-rhamnopyranoside (12) was found to possess the best inhibitory activity with an IC50 value of 29.3 μm.
Regioselective synthesis of di-C-glycosylflavones possessing anti-inflammation activities
Shie, Jiun-Jie,Chen, Chih-An,Lin, Chih-Chien,Ku, Angela Fay,Cheng, Ting-Jen R.,Fang, Jim-Min,Wong, Chi-Huey
experimental part, p. 4451 - 4462 (2010/11/05)
Three methods are utilized to synthesize a variety of 6,8-di-C- glycosylflavones bearing identical or distinct glycosyl moieties. Some C-glycosylation compounds are found to have better anti-inflammation activities than the parent flavones. Among them, 6,8-di-C-glucosylapigenin (known as vicenin-2) shows inhibition of TNF-α expression and NO production with IC50 values of 6.8 and 5.2 μM, respectively.
Quantitation of chafurosides A and B in tea leaves and isolation of prechafurosides A and B from oolong tea leaves
Ishida, Hitoshi,Wakimoto, Toshiyuki,Kitao, Yukiko,Tanaka, Shimako,Mlyase, Toshio,Nukaya, Haruo
scheme or table, p. 6779 - 6786 (2010/08/19)
A procedure was developed for the quantitative determination of chafuroside A, a flavone C-glycoside with potent anti-inflammatory activity, and its regioisomer chafuroside B, as well as isovitexin and vitexin, by selected reaction monitoring liquid chromatography-tandem mass spectrometry (SRM LC-MS/MS) analysis. This method was successfully applied to commercial leaves of green tea, houji tea, oolong tea, and black tea. High levels of chafurosides A and B were found in oolong tea leaves that had been heated at >140°C. Next, their precursors, prechafurosides A and B, were isolated from methanol extract of oolong tea leaves prepared from Shizu 7132, Camellia sinensis (L.) O. Kuntze, by partition with n-butanol and H2O and chromatography on Diaion SP-825, Sephadex LH-20, and ODS C-18, guided by assay of chafuroside formation. Prechafurosides A and B gave chafurosides A and B, respectively, in good yields when heated at 160°C for 0.5 h. Solvolysis of prechafurosides A and B with pyridine and dioxane quantitatively afforded isovitexin and vitexin, respectively. On the basis of these results and physicochemical data (MS, UV, and NMR), prechafurosides A and B were concluded to be new flavone C-glycoside sulfates, isovitexin2"-sulfate and vitexin-2″-sulfate, respectively.
Concise synthesis of chafurosides A and B
Furuta, Takumi,Nakayama, Miho,Suzuki, Hirotaka,Tajimi, Hiroko,Inai, Makoto,Nukaya, Haruo,Wakimoto, Toshiyuki,Kan, Toshiyuki
supporting information; experimental part, p. 2233 - 2236 (2009/10/02)
The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from β-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.
