- Flavonoids as effective protectors of urease from ultrasonic inactivation in solutions
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Inactivation of soybean urease in aqueous solution at pH 5.4, 36°C, and high-frequency sonication (2.64 MHz, 1.0 W/cm2) is substantially reduced in the presence of seven structurally different flavonoids. A comparative kinetic study of the effect of these flavonoids on the effective first-order rate constants that characterize the total (thermal and ultrasonic) inactivation k i , thermal inactivation k*i, and ultrasonic inactivation k i (US) of 25 nM enzyme solution was carried out. The dependences of the three inactivation rate constants of the urease on the concentrations of flavonoids within the range from 10-11 to 10-4 M were obtained. The following order of the efficiency of the flavonoids used in respect of the urease protection from ultrasonic inactivation was found: astragalin > silybin > naringin > hesperidin > quercetin > kaempferol > morin. The results confirm a significant role in the inactivation of the urease of HO. and HO 2 . free radicals, which are formed in the ultrasonic cavitation field. Pleiades Publishing, Inc., 2006.
- Tarun,Kurchenko,Metelitza
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- Bioactive compounds of the flora of belarus. 3.* Gymnocarpium dryopteris, a kaempferol source
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Kaempferol (2) was isolated from the aerial part of the oak fern Gymnocarpium dryopteris by extraction and subsequent acid hydrolysis of the glycoside mixture.
- Kovganko,Kashkan,Krivenok
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- Tannins, flavonol sulfonates, and a norlignan from Phyllanthus virgatus
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Investigation of the constituents of Phyllanthus virgatus has led to the isolation of five new compounds, including a norlignan, 2-(3,4- methylenedioxybenzyl)-4-(3,4-methylenedioxyphenyl)-3-butyne-1,2-diol named virgatyne (1); a hydrolyzable tannin, virganin (2); and three flavonoid sulfonates, galangin-8-sulfonate (4), galangin-3-O-β-D-glucoside-8- sulfonate (5), and kaempferol-8-sulfonate (6). Their structures were established by spectral and chemical methods.
- Huang, Yu-Lin,Chen, Chien-Chih,Hsu, Feng-Lin,Chen, Chieh-Fu
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- A new acylated flavonol glycoside from the aerial parts of Cardamine tangutorum
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A new acylated flavonol glycoside, kaempferol-3-O-β-d-(2- feruloylglucopyranosyl) (1 → 6)-[β-d-glucopyranosyl(1 → 2)]-β-d-glucopyranoside, named tangutorumoside A (1), together with 12 known compounds, was isolated from 50% acetone extract of Cardamine tangutorum. Their structures were elucidated by NMR and MS experiments. In addition, compound 1 could promote the proliferation of splenic lymphocytes and thymic lymphocytes with ConA in vitro.
- Feng, Wei-Sheng,Zhang, Qiu-Bo,Zheng, Xiao-Ke,Chen, Hui,Zhang, Yan-Li,Zhang, Chun-Lei
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- Anti-complement activity of tiliroside from the flower buds of Magnolia fargesii
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As part of the search for anticomplementary active components from natural products, the anticomplementary properties of methanolic extracts from the flower buds of Magnolia fargesii have been investigated. Bioassay- guided chromatographic Separation of the active constituents led to the isolation of compound 1, whose structure was identified by spectroscopic methods to be kaempferol 3-O-β-D-(6-O-coumaroyl)glucopyranoside (tiliroside). Tiliroside showed very potent anti-complement activity (IC50=5.4x 10-5 M) on the classical pathway of the complement system, even higher than rosmarinic acid, which is a well-known inhibitor against the complement system. On the other hand, the hydrolysates of tiliroside, kaempferol, astragalin and p-coumaric acid showed very weak activity on this system.
- Jung, Keun Young,Oh, Sei Ryang,Park, Si-Hyung,Lee, Im Seon,Ahn, Kyung Seop,Lee, Jung Joon,Lee, Hyeong-Kyu
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- Antitumor, antioxidant and anti-inflammatory activities of kaempferol and its corresponding glycosides and the enzymatic preparation of kaempferol
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Kaempferol (kae) and its glycosides are widely distributed in nature and show multiple bio-activities, yet few reports have compared them. In this paper, we report the antitumor, antioxidant and anti-inflammatory activity differences of kae, kae-7-O-gluco
- Wang, Jingqiu,Fang, Xianying,Ge, Lin,Cao, Fuliang,Zhao, Linguo,Wang, Zhenzhong,Xiao, Wei
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- Isolation, characterization, complete structural assignment, and anticancer activities of the methoxylated flavonoids from rhamnus disperma roots
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Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three O-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-O-methyl flavone (penduletin) (1), 5,3’-dihydroxy-3,6,7,4’,5’-penta-O-methyl flavone (2), and 5-hydroxy-3,6,7,3’,4’,5’-hexa-O-methyl flavone (3) from Rhamnus disperma roots. Additionlly, four flavonoid glycosides; kampferol 7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-β-D-glucopyranoside (5), quercetin 7-O-α-L-rhamnopyranoside (6), and kampferol 3, 7-di-O-α-L-rhamnopyranoside (7) along with benzyl-O-β-D-glucopyranoside (8) were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The O-methyl protons and carbons of the three O-methylated flavonoids (1–3) were unambiguously assigned based on 2D NMR data. The occurrence of compounds 1, 4, 5, and 8 in Rhamnus disperma is was reported here for the first time. Compound 3 was acetylated at 5-OH position to give 5-O-acetyl-3,6,7,3’,4’,5’-hexa-O-methyl flavone (9). Compound 1 exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC50 values at 2.17 μM, 0.53 μM, and 2.16 μM, respectively, and was 2–9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G1 cell cycle arrest. The acetylated compound 9 exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC50 values at 2.19 μM and 3.18 μM, respectively, and was 6–8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells.
- Abd El-Wahab, Mohammed F.,Abdalla, Ashraf N.,Mohammed, Abd El-Salam I.,Mohammed, Hamdoon A.,Ragab, Ehab A.,Shaheen, Usama
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- Flavonol Glycosides from Leaves of Allium microdictyon
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The composition of flavonoids from leaves of Allium microdictyon Prokh. (Amaryllidaceae) was studied for the first time and included 14 compounds including two new flavonol glycosides 1 and 2. UV, IR, and NMR spectroscopic and mass spectrometric data dete
- Olennikov
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p. 1035 - 1039
(2020/11/03)
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- Synthesis and Biological Evaluation of 4-Substituted Kaempfer-3-ols
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The synthesis of two series of five kaempfer-3-ols was described. The first set all have a C-3 hydroxyl group and the second has a carboxymethoxy ether at the C-3 position. Both series have variable substitution at the C-4 position (i.e., OH, Cl, F, H, OMe). Both kaempferols and carboxymethoxy ethers were evaluated for their ability to inhibit ribosomal s6 kinase (RSK) activity and cancer cell proliferation.
- Kim, Sugyeom,Lannigan, Deborah A.,Li, Yu,Lin, Lin,O'Doherty, George A.,Sayasith, Peyton R.,Tarr, Ariel T.,Wright, Eric B.,Yasmin, Sharia
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p. 4279 - 4288
(2020/04/09)
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- Flavonoid glycosides from seeds of Hippophae rhamnoides subsp. Sinensis with α-glucosidase inhibition activity
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Hippophae rhamnoides subsp. Sinensis is a famous traditional medicinal plant in Tibet and Mongolia of China. Three novel flavonoid glycosides and ten known analogues were obtained from the seeds of H. rhamnoides. The structures of new compounds were elucidated by spectroscopics, chemical methods as well as literature data. In vitro assay, compounds 5–9, kaempferol and 70% ethanolic elution fraction showed prominent α-glucosidase inhibitory activities with IC50 values ranging from 8.30 to 112.11 μM, better than that of the positive control, acarbose, whose IC50 value was 1727.07 μM.
- Li, Rui,Wang, Qing,Zhao, Menghao,Yang, Peiming,Hu, Xiao,Ouyang, Danwei
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- Preparation method of kaempferol
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The invention relates to a synthesis method of a bulk drug, in particular to a preparation method of kaempferol. The preparation method of the kaempferol is provided in order to solve the technical problems that in the prior art, when purified kaempferol is separated from plants, waste of plant resources and solvents is large, and a total-synthesis method of the kaempferol is long in synthesis route, many in step, low in yield, and difficult to meet the requirements of industrial production are difficult to meet. According to the preparation method, dihydromyricetin is selected as a starting raw material, a kaempferol crude product is obtained through three step reactions of hydrolysis, catalytic closed-loop and oxidation, and the kaempferol crude product is purified and refined to obtainkaempferol refined product with the qualified quality. According to the preparation method of the kaempferol, raw materials are easy to obtain, operation is easy, the cost is low, and the preparationmethod is suitable for industrial production.
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- Development and Optimization of an in Vitro Multienzyme Synthetic System for Production of Kaempferol from Naringenin
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An in vitro multienzyme synthetic system was developed and optimized to efficiently produce kaempferol in a single reaction tube. Two key genes, Atf3h and Atfls1, in the biosynthetic pathway of kaempferol were cloned into a prokaryotic expression vector and overexpressed in Escherichia coli. The recombinant proteins were purified through affinity chromatography and showed activities of flavanone 3-hydroxylase and flavonol synthase, respectively, followed by development of an in vitro synthetic system for producing kaempferol. The system contains 8.2 mM α-ketoglutaric acid, 0.01 mM ferrous ion, 0.4% sodium ascorbate, 25 μg/mL of each recombinant enzyme, and 10% glycerol in 100 mM Tris-HCl (pH 7.2). When the reaction was carried out at 40 °C for 40-50 min, the yield of kaempferol was 37.55 ± 1.62 mg/L and the conversion rate from NRN to KMF was 55.89% ± 2.74%. Overall, this system provides a promising and efficient approach to produce kaempferol economically.
- Zhang, Zhiping,He, Yanzhi,Huang, Yue,Ding, Li,Chen, Lei,Liu, Yaxian,Nie, Yesen,Zhang, Xinyue
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p. 8272 - 8279
(2018/07/30)
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- Flavanonol Glycosides from Leaves of Phellodendron lavallei Introduced in Georgia
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The new flavanonol glycoside (2S,3S)-3,5-dihydroxy-2-(4′-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-3,4-dihydro-2H-chromen-7-yl-β-D-glucopyranosyl-(3→1)-xylopyranoside (lavaloside) (1) and the known compound phellamurin (2) were isolated from leaves o
- Shalashvili,Sutiashvili,Alaniya,Kavtaradze, N. Sh.,Skhirtladze
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p. 263 - 266
(2018/04/17)
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- Flavonoid glycosides from Sedum bulbiferum
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The MeOH extract from dried whole Sedum bulbiferum MAKINO (Crassulaceae) plants yielded 34 compounds, including six new flavonoid glycosides and 28 known compounds. The structures of new compounds were established using NMR, Mass spectroscopic analysis an
- Warashina, Tsutomu,Miyase, Toshio
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p. 1199 - 1204
(2017/12/26)
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- Exploratory Studies on the in Vitro Anti-inflammatory Potential of Two Herbal Teas (Annona muricata L. and Jasminum grandiflorum L.), and Relation with Their Phenolic Composition
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The need of new anti-inflammatory drugs has led to the search for safer and more potent molecules in distinct sources, such as natural products. This work aimed to explore the anti-inflammatory potential of aqueous extracts from two herbal teas (Annona muricata L. and Jasminum grandiflorum L.) in RAW 264.7 macrophages cells and in cell-free assays. Furthermore, the phenolic composition of both extracts and of their hydrolysates was characterized by HPLC-DAD, in order to establish possible relationships with the biological activity. In a general way, A.?muricata displayed a stronger capacity to inhibit nitric oxide (NO) production and the activity of phospholipase A2 (PLA2), displaying an IC50 value of 142?μg/ml against this enzyme. A deeper look at phenolic compounds revealed that aglycones had more capacity to inhibit NO and PLA2 than their corresponding glycosides, quercetin being clearly the most potent one (IC50?=?7.47 and 1.36?μm, respectively). In addition, 5-O-caffeoylquinic acid, at 1.56?μm, could also inhibit PLA2 (ca. 35%). Our findings suggest that the consumption of both herbal teas may be a preventive approach to inflammatory disorders.
- Oliveira, Andreia P.,Sá, Ivone,Pereira, David M.,Gon?alves, Rui F.,Andrade, Paula B.,Valent?o, Patrícia
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- Expanded investigations of the aglycon promiscuity and catalysis characteristic of flavonol 3-: O -rhamnosyltransferase AtUGT78D1 from Arabidopsis thaliana
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Rhamnosides usually possess better bioavailabilities and improved solubilities compared with their aglycons and are a major source of bioactive natural products. However, biosynthesis of rhamnosides is hindered by the commercially expensive UDP-rhamnose (UDP-Rha) donor and a lack of universal rhamnosyltransferases. In the present study, an efficient UDP-Rha production system via a two-step enzymatic reactions using UDP-glucose (UDP-Glc) as a substrate was constructed. Extensive in vitro enzymatic assays and preparative reactions using the obtained UDP-Rha/UDP-Glc highlighted the robust glycosylation promiscuity of the reported rhamnosyltransferase AtUGT78D1. Based on HPLC-UV and HR-MS analyses, 30 of the tested aromatic compounds belonging to 7 structural types, including flavonoids, flavonoid glycosides, phenylethyl chromones, benzophenones, coumarins, lignanoids, and anthraquinones, were accepted by AtUGT78D1 to conduct the corresponding rhamnosylation and/or glucosylation with one or more glycosyl substitutions at different positions. Further preparative reactions expanded the catalytic characteristic of AtUGT78D1 since it can catalyse the rhamnosylation at the 3-OH position of the flavonols, glucosylation at the 7-OH position of the flavone baicalein, and multiple hydroxyl substitutions for diverse types of aromatics. Interestingly, a unique reversible catalysis activity of AtUGT78D1 was observed, and it has been effectively used in one-pot rhamnosylation of the desired rhamnoside. The enzymatic rhamnosylations of diverse "drug-like" scaffolds as well as bidirectional catalysis for one-pot rhamnosylations by plant rhamnosyltransferase were rarely reported before, which indicated that AtUGT78D1 was expected to be a universal and effective tool for chemo-enzymatic synthesis of diverse bioactive rhamnosylated derivatives for drug discovery.
- Mo, Ting,Liu, Xiao,Liu, Yuyu,Wang, Xiaohui,Zhang, Le,Wang, Juan,Zhang, Zhongxiu,Shi, Shepo,Tu, Pengfei
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p. 84616 - 84626
(2016/11/02)
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- The Gastrointestinal Tract Metabolism and Pharmacological Activities of Grosvenorine, a Major and Characteristic Flavonoid in the Fruits of Siraitia grosvenorii
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Grosvenorine is the major flavonoid compound of the fruits of Siraitia grosvenorii (Swingle) C. Jeffrey, a medical plant endemic to China. In the present study, for the first time, the grosvenorine metabolism in an in vitro simulated human gastrointestinal tract (including artificial gastric juice, artificial intestinal juice and intestinal flora), as well as its pharmacological activities (including anti-complement, antibacterial and antioxidant activities), was investigated. The results showed that grosvenorine was metabolized by human intestinal flora; its four metabolites were isolated by semi-preparative HPLC and identified by NMR as kaempferitrin, afzelin, α-rhamnoisorobin, and kaempferol. Further pharmacological evaluation showed that grosvenorine exhibited good antibacterial and antioxidant activities, with its metabolites possessing more potent activities. Although grosvenorine did not present obvious anticomplement activity, its metabolites showed interesting activities. This study revealed that intestinal bacteria play an important role in the gastrointestinal metabolism of grosvenorine and significantly affect its pharmacological activities.
- Wang, Mengyue,Xing, Shihua,Luu, Thithanhthuy,Fan, Min,Li, Xiaobo
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p. 1652 - 1664
(2015/11/24)
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- Anticancer and antiviral estimation of three Ulmus pravifolia extracts and their chemical constituents
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Anticancer and antiviral activity of methanol, chloroform and butanol extracts of Ulmus pravifolia were tested on three cytokines of the human ascites fluid, TNF-alpha, Interferonsgamma and NO. Chloroform and butanol extracts showed a significant curative effect. Both butanol and chloroform extract undergo chromatographic fractionation to yield five compounds identified as Hederagenin 3-O-β-D-glucopyranoside (1), Kaempferol 3-O-β-D-glucopyranosyl- (1→2)-α -L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-7-O-β-D-glucopyranoside (2), 24-hydroxy-24-methylcycloartanol trans-ferulate (3), lupeol caffeate (4) and UlmicinD (5). All compounds were isolated from the plant for the first time. The five compounds showed significant curative effect.
- Hamed, Manal M.,El-Amin, Samir M.,Refahy, Laila A.,Soliman, El-Sayed A.,Mansour, Wafaa A.,Abu Taleb, Hoda M.,Morsi, Eman A.
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p. 1621 - 1634
(2016/01/26)
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- Differences in the floral anthocyanin content of violet-blue flowers of Vinca minor L. and V. major L. (Apocynaceae)
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Two novel delphinidin 3-(tri or di)-glycoside-7-glycosides were isolated from the violet-blue flowers of Vinca minor L. and V. major L. (Family: Apocynaceae), and determined to be delphinidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(α-rhamnopyranosyl)-β-galactopyranoside]-7-O-(α-rhamnopyranoside) [= delpphinidin 3-(2G-xylosylrobinobioside)-7-rhamnoside] as major floral anthocyanin of V. minor and delphinidin 3-O-[6-O-(α-rhamnopyranosyl)-β-galactopyranoside]-7-O-(α-rhamnopyranoside) [= delpphinidin 3-robinobioside-7-rhamnoside] as major floral anthocyanin of V. major by chemical and spectroscopic methods. In addition, chlorogenic acid and kaempferol 3-O-[6-O-(α-rhamnopyranosyl)-β-galactopyranoside]-7-O-(α-rhamnopyranoside) [= kaempferol 3-robinobioside-7-rhamnoside (robinin)] were identified in these flowers. In this paper, the relation between the structure of floral anthocyanins and classification of Vinca species was discussed.
- Tatsuzawa, Fumi
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p. 365 - 369
(2015/08/24)
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- Phytochemical screening of flavonoids with their antioxidant activities from rapeseed (Brassica napus L.)
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Abstract Ten flavone compounds, including three new flavonoid glycosides, were isolated from defatted rapeseed, and their protective antioxidant effect on H2O2-induced oxidative damage in human umbilical vein endothelial cells (ECV-304) was investigated. Three new flavonoid glycosides were identified as kaempferol-3-O-[(6-O-sinapoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside]-7-O-β-d-glucopyranoside (8), kaempferol-3,7-di-O-β-d-glucopyranoside-4'-O-(6-O-sinapoyl)-β-d-glucopyranoside (9), and kaempferol-3-O-[(3-O-sinapoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside]-7-O-β-d-glucopyranoside (10). The protective effects of all of the isolated compounds on H2O2-induced oxidative damage were assessed, and the activities of superoxide dismutase (SOD) and lactate dehydrogenase (LDH) were measured. All of compounds had a protective effect on H2O2-induced oxidative damage in ECV-304 cells and the presence of a substituted sinapoyl group and its position in the structures were used to elucidate the activity differences.
- Jing, Wen Guang,Fu, Jiang,Guo, Yan,Liu, An
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p. 239 - 245
(2015/08/06)
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- Bioactive secondary metabolites from tecomella undulata
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Chromatographic purification of the methanolic extract of Tecomella undulata yielded a new flavonoid glycoside; kaempferol-3-O-β-D-[3 ,4di-p-E -coumaroyl-α-L-rhamnosyl(1→6)] galactoside (1 ), two new megastigmanes; (6R 7Z )-9,10-dihydroxy-4,7-megastigmadien-3-one (2) and (6E )-9,10-dihydroxy-4,6-megastigmadien-3-one (3) along with three known compounds; (6R 9S)-9,10-dihydroxy-4-megastigmaen-3-one (4) quercetin-3-galactoside (5) and 3′-dimethoxy-5,6,4′-trihydroxyflavon (6). All the isolates 1-6 were characterized by the combination of 1D (1H, 13C), 2D (COSY, HSQC and HMBC) NMR data and high resolution mass spectrometric analysis. In antibacterial assay, compound 1 showed moderate inhibitory activity against Escherichia coli and Salmonalla typhi.
- Ahmad, Shabir,Musaddiq, Sara,Saleem, Muhammad,Riaz, Naheed,Fatima, Sundas,Yaqoob, Asma,Jabbar, Abdul,Nasim, Faiz-Ul-Hassan
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p. 1122 - 1128
(2015/01/30)
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- Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris)
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While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-P-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (1), kaempferol 3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E - p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1-6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.
- Zuchowski, Jerzy,Pecio, Lukasz,Stochmal, Anna
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p. 18152 - 18178
(2015/02/19)
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- Flavonoid glycosides from hosta longipes, their inhibition on no production, and nerve growth factor inductive effects
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An extended phytochemical investigation of the leaves of Hosta longipes identified the new flavonoid glycoside, kaempferol-3-O-β-D-glucopyranosyl- (1?2)-[6'''-O-acetyl-β-Dglucopyranoside]- 7-O-β-D-glucopyranoside and five known flavonoid derivatives. The
- Kim, Chung Sub,Kwon, Oh Wook,Kim, Sun Yeou,Lee, Kang Ro
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p. 907 - 912
(2014/06/24)
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- Kaempferol and its glycosides from Equisetum silvaticum L. from the khanty-mansi autonomous area
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Three flavonoids were isolated from the aerial part of the wood horsetail (Equisetum silvaticum L.); two of them were found for the first time. The compounds were identified as kaempferol, kaempferol 3-O-β-D-galactopyranosyl-7-O-α-L-rhamnopyranoside and kaempferol 3-O-rutinosyl-7-O-L-rhamnopyranoside on the basis of the chemical transformations and IR, UV, 1H-NMR and mass spectra.
- Bonacheva,Botirov, E. Kh.
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p. 777 - 780
(2015/01/30)
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- Two new flavonol glycosides and biological activities of Diplotaxis harra (Forssk.) Boiss.
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Two new flavonol glycosides, isorhamnetin 3-O-β-glucopyranoside- 4′-O-β-xylopyranoside (1) and kaempferol 3-O-β-glucopyranoside -4′-O-β-xylopyranoside (2), were isolated from the defatted aqueous methanol extract of the whole plant Diplotaxis harra along with 12 known flavonols (3-14). They were characterised by chemical and spectral methods. The 70% aqueous methanol, chloroform and defatted aqueous methanol plant extracts exhibited significant antioxidant effects (nitroblue tetrazolium reduction method). Their cytotoxic activity was carried out against 11 tumour cell lines (sulphorhodamine B assay). The three extracts expressed the greatest antiproliferative activity against colon 38, P388 and MKN-28 with GI50 (0.45, 0.4, 0.07 g/mL) and against P388 [3-(4,5-dimethylthiazol-2yl)-2,5- diphenyltetrazolium bromide assay] with IC50 (0.26, 0.24, 0.25 g/mL), respectively. The chloroform extract showed the highest activity as eukaryotic DNA topoisomerase II inhibitors of P388 with IC50 0.24 g/mL. Antiviral screening of the extracts and the pure compounds against foot-and-mouth disease virus types A and O revealed a prominent inhibition of its cytopathic effect. 2013
- Kassem, Mona E.S.,Afifi, Manal S.,Marzouk, Mona M.,Mostafa, Manal A.
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p. 2272 - 2280
(2014/01/06)
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- Flavonoids from the cocoon of Rondotia menciana
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Two flavonol glycosides along with four known flavonoids were isolated from the cocoon of the mulberry white caterpillar, Rondotia menciana (Lepidoptera: Bombycidae: Bombycinae), a closely related species of the domesticated silkworm Bombyx mori, both of which feed on leaves of mulberry (Morus alba). The two glycosides were characterized as quercetin 3-O-β-D-galactopyranosyl-(1 → 3)-β-D-galactopyranoside and kaempferol 3-O-β-D- galactopyranosyl-(1 → 3)-β-D-galactopyranoside, based on spectroscopic data and chemical evidence. The flavonol galactosides found in the cocoon were not present in the host plant, nor in the cocoon of the silkworm, B. mori. Notably, flavonol glucosides, which are the main constituents of cocoon flavonoids in B. mori mori, were not found in the R. menciana cocoon. The present result strongly suggests that R. menciana is quite unique in that they predominantly use an UDP-galactosyltransferase for conjugation of dietary flavonoids, whereas UDP-glucosyltransferases are generally used for conjugation of plant phenolics and xenobiotics in other insects.
- Hirayama, Chikara,Ono, Hiroshi,Meng, Yan,Shimada, Toru,Daimon, Takaaki
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p. 108 - 112
(2013/10/22)
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- New chemical constituents from oryza sativa straw and their algicidal activities against blue-green algae
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Five new constituents, 5,4′-dihydroxy-7,3′-dimethoxyflavone- 4′-O-β-d-xylopyranosyl-(2a→1b)-2a-O-β-d-xylopyranosyl- (2b→1c)-2b-O-β-d-xylopyranosyl-2c-octadecanoate (1), 5,4′-dihydroxy-7,3′-dimethoxyflavone-4′-O-α-d- xylopyranosyl-(2a→1b)-2a-O-α-d-xylopyranosyl-(2b→1c) -2b-O-α-d-xylopyranosyl-(2c→1d)-2c-O-α-d-xylopyranosyl-2d- octadecanoate (2), kaempferol-3-O-α-d-xylopyranosyl-(2a→1b)-2a-O- α-d-xylopyranosyl-(2b→1c)-2b-O-α-d-xylopyranosyl-(2c→1d) -2c-O-α-d-xylopyranosyl-2d-hexadecanoate (3), methyl salicylate-2-O- α-d-xylopyranosyl-(2a→1b)-2a-O-α-d-xylopyranosyl-(2b→1c) -2b-O-α-d-xylopyranosyl-(2c→1d)-2c-O-α-d-xylopyranosyl- (2d→1e)-2d-O-α-d-xylopyranosyl-(2e→1f)-2e-O-α-d- xylopyranosyl-(2f→1g)-2f-O-α-d-xylopyranosyl-(2g→1h) -2g-O-α-d-xylopyranosyl-2h-geranilan-8′,10′-dioic acid-1′-oate (4), and oleioyl-β-d-arabinoside (5), along with eight known compounds, were isolated from a methanol extract of Oryza sativa straw. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopies in combination with IR, ESI/MS, and HR-ESI/FTMS. In bioassays with blue-green algae, the efficacies of the algicidal activities of the five new compounds (1-5) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound 5 had the highest growth inhibition (92.6 ± 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound 5 has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.
- Ahmad, Ateeque,Kim, Seung-Hyun,Ali, Mohd,Park, Inmyoung,Kim, Jin-Seog,Kim, Eun-Hye,Lim, Ju-Jin,Kim, Seul-Ki,Chung, Ill-Min
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p. 8039 - 8048
(2013/09/23)
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- New acylated flavonoid glycosides from flowers of Aerva javanica
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Chromatographic purification of ethyl acetate soluble fraction of the methanolic extract of the flowers of Aerva javanica yielded three new acylated flavone glycosides: kaempferol-3-O-β-d-[4?-E-p-coumaroyl-α-l- rhamnosyl(1 → 6)]-galactoside (1), kaempfero
- Mussadiq, Sara,Riaz, Naheed,Saleem, Muhammad,Ashraf, Muhammad,Ismail, Tayaba,Jabbar, Abdul
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p. 708 - 716
(2013/08/14)
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- Inhibitory effects of the constituents of hippophae rhamnoides on 3t3-l1 cell differentiation and nitric oxide production in RAW264.7 Cells
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Three new flavonol glycosides, hippophaeosides A-C (1-3), together with 27 known constituents, were isolated from Hippophae rhamnoides L. leaves. Their structures were determined by spectroscopic analyses. Their inhibitory activities on 3T3-L1 preadipocyte differentiation and triglyceride accumulation in maturing adipocytes, and nitric oxide production in RAW264.7 cells were examined.
- Yang, Zhi-Gang,Wen, Xiu-Feng,Li, Yong-Hai,Matsuzaki, Keiichi,Kitanaka, Susumu
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p. 279 - 285
(2013/05/08)
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- Flavonol glycosides from Cardamine komarovii
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Two new flavonol glycosides (1 and 2) were isolated from a MeOH extract of the aerial parts of Cardamine komarovii Nakai (Cruciferae) together with 13 known phenolic compounds (3-15). The structures of 1 and 2 were determined by spectroscopic methods including 1D and 2D NMR (COSY, HMQC, HMBC, NOESY, and TOCSY) and HR-FAB-MS data.
- Lee, Seung Young,Lee, Il Kyun,Lee, Kang Ro
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p. 753 - 757,5
(2020/08/24)
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- Flavonoid glycosides from Botrychium ternatum
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The MeOH extract from dried whole Botrychium ternatum plants yielded 33 compounds, including seventeen new flavonoid glycosides and sixteen known compounds. The structures of new compounds were established using NMR spectroscopic analysis and chemical evi
- Warashina, Tsutomu,Umehara, Kaoru,Miyase, Toshio
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p. 1561 - 1573
(2013/02/22)
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- Chemical constituents, antischistosomal and antioxidant activities of the methanolic extract of Azadirachta indica
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THE PRESENT study was performed to evaluate the in vitro schistosomicidal effect of 70% methanolic extract of the leaves of Azadirachta indica and its derived ethyl acetate and n-butanol fractions against adult Schistosoma mansoni worms. Also, antioxidant properties of these extracts were determined. Owing to the high antischistosomal and antioxidant activities of EtOAc and n-BuOH fractions, they were subjected to chromatographic isolation using different chromatographic techniques. Two flavonoid compounds; (1,2) were isolated from EtOAc fraction whereas one flavonoid; (3) quercetin-3-O-a-L-rhamnopyranoside and two bidesmosidic saponins; (4,5) were isolated from the butanolic fraction. Their structures were established using spectroscopic methods. Compounds 1-3 showed high antioxidant activity whereas compounds 4 and 5 were inactive. It is the first time that antischistosomal activity of A.indica and isolation of compounds 2-5 from this plant were carried out.
- El-Sayed,Mahmoud,El-Nahas, Hanan A.,El-Toumy,El-Wakil, Eman A.,Ghareeb
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- New flavonol glycosides from Cardamine komarovii
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Seven new kaempferol glycosides (1-7), together with three known kaempferol glycosides (8-10), were isolated from a MeOH extract of Cardamine komarovii Nakai (Cruciferae). The chemical structures of the new compounds (1-7) were determined on the basis of their MS, 1H-NMR, 13C-NMR, COSY, HMBC, NOESY and TOCSY data, and results of hydrolysis.
- Lee, Il Kyun,Jeong, Eun-Kyung,Choi, Sang Un,Hong, Jongki,Lee, Kang Ro
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experimental part
p. 2615 - 2625
(2012/01/05)
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- Flavonoids from the flowers of Aesculus hippocastanum
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The flavonoids, kaempferol derivatives: 3-O-α-arabinofuranoside, 3-O-β-glucopyranoside, 3-O-α-rhamnopyranoside, 3-O-α- rhamnopyranosyl (1→6)-O-β-glucopyranoside and quercetin derivatives: 3-O-α-arabinofuranoside, 3-O-β-glucopyranoside, 3-O-α- rhamnopyranosyl (1→6)-O-β-glucopyranoside, were isolated from the flowers of Aesculus hippocastanum and identified. The structures of these compounds were confirmed by a chemical analysis and spectrophotometric methods (UV, 1H-, 13C-NMR, ESI-MS). The presence of free aglycones: kaempferol and quercetin was confirmed chromatographically by comparison with standards.
- Dudek-Makuch, Marlena,Matlawska, Irena
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experimental part
p. 403 - 408
(2011/12/03)
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- A new flavonol glycoside from the seeds of Nigella glandulifera
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A new flavonol glycoside, kaempferol 3-O-α-L-rhamnopyranosyl (1→6)-O-[β-D-glucopyranosyl (1→2)-O-β-D-galactopyranosyl (1→2)]-O- β-D-glucopyranoside (1), together with a known compound, kaempferol 3-O-β-D-glucopyranosyl (1→2)-O-β-D-galactopyranosyl (1→2)-O-β-Dglucopyranoside (2) was isolated from the seeds of Nigella glandulifera. Their structures were elucidated on the basis of spectral analysis, including ESI-MS, ESI-MS/MS, HR-ESI-MS, DQF-COSY, TOCSY, HSQC and HMBC techniques.
- Liu, Yu-Ming,Liu, Qing-Hua,Chen, Bao-Quan
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body text
p. 1334 - 1338
(2011/10/13)
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- Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs
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A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant.
- Pandurangan,Bose, Chinchu,Banerji
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experimental part
p. 5328 - 5330
(2011/10/09)
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- Study of kaempferol glycoside as an insulin mimic reveals glycon to be the key active structure
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Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1), a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.
- Yamasaki, Kazuaki,Hishiki, Ryogo,Kato, Eisuke,Kawabata, Jun
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- Antioxidative caffeoylquinic acids and flavonoids from Hemerocallis fulva flowers
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Tumor necrosis factor-α (TNF-α)-induced reactive oxygen species (ROS) production in HepG2 was used to screen hepatocyte protective compounds from the flowers of Hemerocallis fulva. Three new polyphenols, n-butyl 4-trans-O-caffeoylquinate (1), kaempferol 3-O-{α-l- rhamnopyranosyl(1→6)[α-l-rhamnopyranosyl(1→2)]} -β-d-galactopyranoside (2), and chrysoeriol 7-O-[β-d- glucuronopyranosyl(1→2)(2-O-trans-feruloyl)-β-d-glucuronopyranoside (3), together with four caffeoylquinic acid derivatives (4-7), eight known flavones (8-15), one naphthalene glycoside, stelladerol (16), one tryptophan derivative (17), adenosine (18), and guanosine (19) were isolated from the bioactive fractions of the aqueous ethanol extract of H. fulva flowers. The structures of isolated compounds were characterized by means of spectroscopic data. Compounds 1-3 were described as first isolated natural products. Among the above-mentioned compounds, the caffeoylquinic acid derivatives are the major components with potent free radical scavenging activity in HepG2 cells and are for the first time isolated from H. fulva flowers. A convenient ultraperformance liquid chromatography (UPLC) method was also developed to simultaneously separate and identify caffeoylquinic acids and flavonoids promptly.
- Lin, Yun-Lian,Lu, Chung-Kuang,Huang, Yeh-Jeng,Chen, Hong-Jhang
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experimental part
p. 8789 - 8795
(2012/07/03)
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- Changes in flavonoid content and tyrosinase inhibitory activity in kenaf leaf extract after far-infrared treatment
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The tyrosinase inhibitory activity of ethanolic extract of kenaf (Hibiscus cannabinus L.) leaf was evaluated before and after subjecting it to far-infrared (FIR) irradiation. The main component of the extract was analyzed as kaempferitrin (kaempferol-3,7-O-α-dirhamnoside). Prior to FIR irradiation, no inhibitory activity of the extract was detected in a tyrosinase assay. However, after FIR irradiation for 1 h at 60 °C, significant tyrosinase inhibitory activity (IC50 = 3500 ppm) was observed in it. In HPLC analysis, derhamnosylation products (kaempferol, afzelin, and α-rhamnoisorobin) were detected. The inhibitory activity may be due to the existence of derhamnosylation products. This study demonstrated that FIR irradiation can be used as a convenient tool for deglycosylation of flavonoid glycoside.
- Rho, Ho Sik,Ahn, Soo Mi,Lee, Bum Chun,Kim, Myung Kyoo,Ghimeray, Amal Kumar,Jin, Cheng Wu,Cho, Dong Ha
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scheme or table
p. 7534 - 7536
(2011/02/24)
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- Flavonoid constituents of Cakile maritima (scope) growing in Egypt and their biological activity
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The study of the flavonoidal constituents isolated from the chloroform, ethyl acetate and butanol fractions of aqueous alcoholic extract of Cakile maritima (family Crucifereae) revealed the isolation and identification of quercetin, quercetin-3-O-rhamnoside, kaempferol-7-O-glucoside, luteolin, luteolin-7-O-glucoside and caffeic acid. Identification of the isolated compounds was carried out by spectroscopic analysis viz UV, MS, NMR, TLC, PC and acid hydrolysis of the glycoside compounds. The radical scavenging effects of the tested extracts and isolated compounds on DPPH free radical were observed, in which the flavonoidal compounds showed a strong antioxidant activity. Molluscidal activity of different fractions and isolated compounds of Cakile maritime was carried out against Biomphalaria alexandrina snails, in which luteolin-7-O-glucoside, kaempferol-7-O-glucoside and quercetin-3-O-rhamnoside showed significant molluscicidal activity (LC50 24, 37 and 40, respectively). It was also found that the quercetin, luteolin and caffeic acid had showed moderate activity.
- Shams, Khaled A.,Radwan, Hany M.,Tawfik, Wafaa A.,Habib, Amira A.,Soliman, Abdel-Mohsen M.
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experimental part
p. 3981 - 3988
(2010/11/18)
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- Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy
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Two new flavonoids, abutilin A and B, were isolated from the chloroform soluble fraction of Abutilon pakistanicum and their structures assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, HMQC and HMBC experiments. Ferulic acid (3), (E)-cinnamic acid (4), 5-hydroxy-4′,6,7,8- tetramethoxyflavone (5), kaempferol (6), luteolin (7) and luteolin 7-O-β-D-glucopyranoside (8) have also been reported from this species. Copyright
- Ali, Bakhat,Imran, Muhammad,Hussain, Riaz,Ahmed, Zaheer,Malik, Abdul
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experimental part
p. 159 - 163
(2010/07/07)
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- Isolation and synthesis of flavonols and comparison of their antioxidant activity
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Phytochemical investigation of the leaves of Astragalus beckari yielded four flavonol aglycones, namely kaempferol, quercetin, 5-deoxy kaempferol and fisitin. These isolated compounds were then synthesised in the laboratory using the Algar-Flyn-Oyamad reaction. Antioxidant activity of both the isolated and synthesised flavonoids was compared using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay method. The isolated flavonoids were found to be more active.
- Hasan, Aurangzeb,Sadiq,Abbas,Mughal,Khan, Khalid M.,Ali, Muhammad
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experimental part
p. 995 - 1003
(2010/09/05)
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- A novel kaempferol triglycoside from flower buds of Panax quinquefolium
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Three kaempferol glycosides were isolated from the flower buds of Panax quinquefolium L. together with kaempferol (1). By means of chemical and spectroscopic methods (NMR, ESI-MS, 2D NMR), their structures were established as trifolin (2), panasenoside (3
- Liu, ChangDa,Chen, Jing,Wang, JinHui
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experimental part
p. 808 - 810
(2010/07/15)
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- Structural determination of quercusides A and B, new flavonoid glucosides from Quercus incana, by 1D and 2D NMR spectroscopy
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Quercusides A and B, new flavonoid glucosides have been isolated from the chloroform soluble fractions of Quercus incana.Their structures were assigned from 1Hand 13C nuclear magnetic resonance spectra, distortionless enhancement by
- Iftikhar, Benish,Perveen, Shagufta,Malik, Abdul,Sultana, Najma,Arayne, Saeed,Muhammad, Pir
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experimental part
p. 605 - 608
(2010/07/06)
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