scholarly journals Flavonoid Aglycones and Glycosides from the Leaves of some Japanese Artemisia Species

2018 ◽  
Vol 13 (5) ◽  
pp. 1934578X1801300
Author(s):  
Ayumi Uehara ◽  
Kazuhide Shimoda ◽  
Yoshinori Murai ◽  
Tsukasa Iwashina
Keyword(s):  
Acid Hydrolysis ◽  
Methyl Ether ◽  
The Other ◽  
Flavonol Glycosides ◽  
Flavonoid Aglycones ◽  
Other Hand ◽  
Artemisia Species ◽  
C Nmr

Sixteen Japanese Artemisia taxa were surveyed for flavonoid aglycones and glycosides. The leaves were rinsed with acetone and then extracted with MeOH. Isolated flavonoids were identified by UV, LC-MS, acid hydrolysis, 1H and 13C NMR, and/or HPLC comparisons with authentic samples. Thus, nine flavone aglycones, apigenin (10), luteolin (5), chrysoeriol (11), hispidulin (6), jaseosidin (7), nepetin (15), sudachitin (8), luteolin 7-methyl ether (13) and eupatilin (14), three flavonol aglycones, axillarin (9), quercetin 3-methyl ether (16) and 5,7,4′-trihydroxy-3,6-dimethoxyflavone (12), one flavanone aglycone, pinocembrin (4), three dihydroflavonol aglycones, taxifolin (1), taxifolin 3-acetate (2) and padmatin (3) were found in their Artemisia taxa with the various combination. On the other hand, four flavonol glycosides, quercetin 3- O-rutinoside (17), quercetin 3- O-glucoside (18), patuletin 3- O-glucoside (19) and patuletin 3- O-rhamnosylglucoside (20), were isolated from a few Artemisia taxa.

scholarly journals New Acylated Anthocyanins and Other Flavonoids from the Red Flowers of Clematis Cultivars

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Masanori Hashimoto ◽  
Toshisada Suzuki ◽  
Tsukasa Iwashina
Keyword(s):  
Nmr Spectroscopy ◽  
The Other ◽  
Flavonol Glycosides ◽  
Chemical Structures ◽  
Other Hand ◽  
Acylated Anthocyanins ◽  
C Nmr

Six new acylated cyanidin glycosides, cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-galactopyranoside (1), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-(6′′-malonylgalactopyranoside) (2), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)- (1→2)- O-β-(6″-succinylgalactopyranoside) (3), cyanidin 3- O-β-(2′'- E-caffeoylglucopyranosyl)-(1→2)- O-β-galactopyranoside-3′- O-β-glucuronopyranoside (4), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-(6′'-malonylgalactopyranoside)-3′- O-β-glucuronopyranoside (5), and cyanidin 3- O-β-(2′'- E-feruloylglucopyranosyl)-(1→2)- O-β-(6′'-malonylgalactoside)-3′- O-β-glucuronopyranoside (6), were isolated from the red flowers of two Clematis cultivars, ‘Niobe'and ‘Madame Julia Correvon'. The chemical structures of the isolated anthocyanins were determined by UV, LC-MS, HPLC, TLC, characterization of hydrolysates, and 1H and 13C NMR spectroscopy, including H-H COSY, C-H COSY, HMBC, HMQC and NOESY. The last three anthocyanins were widely distributed in 37 red flower Clematis cultivars. On the other hand, the first three compounds were found only in two cultivars. Five known flavonol glycosides, kaempferol 3- O-glucoside, kaempferol 3- O-rutinoside, quercetin 3- O-galactoside, quercetin 3- O-glucoside and quercetin 3- O-rutinoside, were isolated from the flowers of ‘Madame Julia Correvon'.

17O and 13C NMR spectra of some geminal diacetates

1988 ◽  
Vol 53 (3) ◽  
pp. 588-592 ◽  
Author(s):  
Antonín Lyčka ◽  
Josef Jirman ◽  
Jaroslav Holeček
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
The Other ◽  
13C Nmr Spectra ◽  
Other Hand ◽  
Carboxylic Esters ◽  
C Nmr ◽  
Oxygen Atoms

The 17O and 13C NMR spectra of eight geminal diacetates RCH(O(CO)CH3)2 derived from simple aldehydes have been measured. In contrast to the dicarboxylates R1R2E(O(CO)R3)2, where E = Si, Ge, or Sn, whose 17O NMR spectra only contain a single signal, and, on the other hand, in accordance with organic carboxylic esters, the 17O NMR spectra of the compound group studied always exhibit two well-resolved signals with the chemical shifts δ(17O) in the regions of 183-219 ppm and 369-381 ppm for the oxygen atoms in the groups C-O and C=O, respectively.

scholarly journals New Flavonol Glycosides from the Leaves of Triantha Japonica and Tofieldia Nuda

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800
Author(s):  
Tsukasa Iwashina ◽  
Minoru N. Tamura ◽  
Yoshinori Murai ◽  
Junichi Kitajima
Keyword(s):  
Nmr Spectroscopy ◽  
Acid Hydrolysis ◽  
Flavonol Glycosides ◽  
Flavonoid Composition ◽  
New Compounds ◽  
C Nmr

Two new flavonol glycosides were isolated from the leaves of Triantha japonica, together with eight known flavonols, kaempferol 3- O-sophoroside, kaempferol 3- O-sambubioside, kaempferol 3- O-glucosyl-(1→2)-[glucosyl-(1→6)-glucoside], quercetin 3- O-sophoroside, quercetin 3- O-sambubioside, isorhamnetin 3- O-glucoside, isorhamnetin 3- O-sophoroside and isorhamnetin 3- O-sambubioside. The new compounds were identified as kaempferol 3- O-β-xylopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-glucopyranoside] (1) and isorhamnetin 3- O-β-xylopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-glucopyranoside] (3) by UV, LC-MS, acid hydrolysis, and 1H and 13C NMR spectroscopy. Another two new flavonol glycosides were isolated from the leaves of Tofieldia nuda, and identified as kaempferol 3- O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-galactopyranoside] (4) and quercetin 3- O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-galactopyranoside] (5). Though the genera Triantha and Tofieldia were treated as Tofieldia sensu lato, they were recently divided into two genera. It was shown by this survey that their flavonoid composition were also different to each other.

scholarly journals Fluoride kinetics in saliva after the use of a fluoride-containing chewing gum

2005 ◽  
Vol 19 (4) ◽  
pp. 256-260 ◽  
Author(s):  
Maria Francisca Thereza Borro Bijella ◽  
Fernanda Lourenção Brighenti ◽  
Maria Fernanda Borro Bijella ◽  
Marília Afonso Rabelo Buzalaf
Keyword(s):  
Dental Caries ◽  
Acid Hydrolysis ◽  
Analysis Of Variance ◽  
Dental Fluorosis ◽  
The Other ◽  
Chewing Gum ◽  
Other Hand ◽  
High Fluoride ◽  
The Mean ◽  
Post Hoc

There is a relationship between the use of fluoride, the reduction of dental caries and the increase of dental fluorosis. The purpose of this study was to analyze the fluoride kinetics in saliva after using the HappydentTM chewing gum, which contains 3.38 mg of fluoride as monofluorophosphate. Fifteen 7-9-year-old volunteers were instructed to chew the gum TridentTM (control) and HappydentTM on different days. Total saliva was collected for 3 minutes, at 0, 3, 6, 9, 15, 30 and 45 minutes after starting chewing. Salivary fluoride was analyzed with a fluoride-specific electrode (Orion 96-09) after acid hydrolysis. The data were analyzed by two-way analysis of variance and by Tukey’s post hoc test (p < 0.05). The mean amounts ± sd (mg) of fluoride released in saliva were 0.276 ± 0.126 and 0.024 ± 0.014 for HappydentTM and TridentTM respectively. The fluoride amount in the saliva samples after the use of Happydent was significantly higher than after the use of TridentTM in all experimental periods, except after 30 and 45 minutes. The high fluoride presence in saliva after the use of Happydent may be significant to prevent dental caries and this should be evaluated in clinical researches. On the other hand, children at an age of risk for dental fluorosis should avoid the use of HappydentTM.

scholarly journals Further Characterization of Foliar Flavonoids in Crossostephium chinense and their Geographic Variation

2014 ◽  
Vol 9 (2) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Ayumi Uehara ◽  
Junichi Kitajima ◽  
Goro Kokubugata ◽  
Tsukasa Iwashina
Keyword(s):  
Geographic Variation ◽  
Dimethyl Ether ◽  
Methyl Ether ◽  
Leaf Surface ◽  
Flavonoid Glycosides ◽  
Flavonoid Aglycones ◽  
Collection Sites ◽  
C Nmr

Foliar flavonoids of Crossostephium chinense in Japan and Taiwan were isolated and further characterized. Eighteen flavonoid aglycones, luteolin, apigenin, hispidulin, chrysoeriol, 5,7,4′-trihydroxy-6,3′,5′-trimethoxyflavone, jaceosidin, cilsimaritin, quercetin 3-methyl ether, axillarin, chrysosplenol-D, cirsiliol, apometzgerin, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone, luteolin 3′,4′-dimethyl ether, cirsilineol, eupatilin, nepetin and 5,7,3′,4′-tetrahydroxy-6,5′-dimethoxyflavone, were identified by UV, 1H and 13C NMR spectroscopic, LC-MS and HPLC comparisons with authentic samples. The compounds existed on the leaf surface. Four flavonoid glycosides, quercetin 3,7-di- O-glucoside, quercetin 3- O-rutinoside, luteolin 7- O-glucoside and apigenin 7- O-rutinoside, were also isolated as the intracellular flavonoids. It was shown by HPLC survey that variation of the species’ flavonoids occurs among the collection sites.

Novel Epicuticular Leaf Flavonoids from Kalmia and Gaidtheria (Ericaceae)

1984 ◽  
Vol 39 (7-8) ◽  
pp. 710-713 ◽  
Author(s):  
Eckhard Wollenweber ◽  
Gisela Kohorst
Keyword(s):  
Natural Products ◽  
Methyl Ether ◽  
The Other ◽  
Flavonoid Aglycones ◽  
Leaf Wax ◽  
Kalmia Angustifolia ◽  
Epicuticular Layer ◽  
New Compounds ◽  
Gaultheria Procumbens ◽  
Derivatives Of

Abstract Leaves of a number of Ericaceous plants have a thin epicuticular layer that consists mostly of triterpenes. In Kalmia angustifolia, K. latifolia and K. polifolia as well as in Gaultheria procumbens and G. shallon this material also contains trace amounts of flavonoid aglycones. In Kalmia they are the 3-OMe-derivatives of four C-methyl flavones reported previously as the typical leaf-wax flavonoids of Eucalyptus. The new compounds, 5-OH-3,7,4′-triOMe-6,8-diCH3-flavone (kalmiatin), 5-OH-3,7,4′-triOMe-6-CH3-flavone (8-desmethyl-kalmiatin), 5,4′-diOH-3,7-diOMe-6,8-diCH3-flavone (latifolin) and 5,4′-diOH-3,7-diOMe-6-CH3-flavone (8-desmethyl-latifolin) are novel natural products. They could not be detected in eight species of Eucalyptus. A screening of 15 species of Ericaceae revealed that 8-desmethyl-sideroxylin and 8-desmethyl-latifolin are present also in the epicuticular layer on leaves of Gaultheria procumbens, while on G. shallon and on Andromeda polifolia traces of galangin-3-methyl ether were found. In the other species checked no external flavonoid aglycones could be detected.

scholarly journals Anthocyanins and Other Flavonoids as Flower Pigments from Eleven Centaurea Species

2015 ◽  
Vol 10 (3) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Tamaki Mishio ◽  
Kosaku Takeda ◽  
Tsukasa Iwashina
Keyword(s):  
Methyl Ether ◽  
The Other ◽  
Other Hand ◽  
Kaempferol Glycoside ◽  
Flower Pigments

Anthocyanins and other flavonoids were isolated from the flowers of eleven Centaurea species, C. macrocephala, C. rupestotilis and C. suaveolens, which produce yellow flowers, and C. achtarovii, C. dealbata, C. montana, C. nigra, C. scabiosa, C. simplicicaulis, C. hypoleuca and C. triumfetti, which have cyanic flowers. Four anthocyanins, cyanidin 3,5-di- O-glucoside, cyanidin 3- O-(6″-malonylglucoside)-5- O-glucoside, cyanidin 3- O-(6″-succinylglucoside)-5- O-glucoside and cyanidin glycoside, were detected in the cyanic flowers of seven Centaurea species. Of these anthocyanins, the first two were found as major anthocyanins. In the cyanic species, four other flavonoids, apigenin 7- O-glucuronide-4′- O-glucoside, malonylated apigenin 7,4′-di- O-glucoside, apigenin 7- O-glucuronide and kaempferol glycoside, were also isolated. On the other hand, nine flavonols and four flavones were isolated from the three yellow-flowered species, and identified as quercetagetin, quercetagetin 7- O-glucoside, quercetagetin 3′-methyl ether 7- O-glucoside, patuletin, patuletin 7- O-glucoside, quercetin 7- O-glucoside, kaempferol 3-methyl ether, kaempferol 3-methyl ether 4′- O-glucuronide and isorhamnetin 3- O-galactoside, and apigenin, apigenin 7- O-glucuronide, luteolin 7- O-glucoside and apigenin 6,8-di- C-glucoside (vicenin-2). Of these flavonoids, the former five flavonols are “yellow flavonols”, and it was shown that their flower colors are due to these compounds.

Sesquiterpenes and Flavonoid Aglycones from a Hungarian Taxon of the Achillea millefolium Group

2002 ◽  
Vol 57 (11-12) ◽  
pp. 976-982 ◽  
Author(s):  
Sabine Glasl ◽  
Pavel Mucaji ◽  
Ingrid Werner ◽  
Armin Presser ◽  
Johann Jurenitsch
Keyword(s):  
2D Nmr ◽  
The Other ◽  
Achillea Millefolium ◽  
Spectroscopic Methods ◽  
Nmr Studies ◽  
Flavonoid Aglycones ◽  
H Nmr ◽  
Nmr Data ◽  
First Time ◽  
C Nmr

The investigation of a dichloromethane extract of flower heads of a Hungarian taxon of the Achillea millefolium group led to the isolation of three flavonoid aglycones, one triterpene, one germacranolide and five guaianolides. Their structures were elucidated by UV-VIS, EI- and CI-MS, 1H NMR and 13C NMR spectroscopic methods as well as by 2D-NMR studies and by selective 1D-NOE experiments. Besides apigenin, luteolin and centaureidin, β-sitosterol, 3β-hydroxy-11α,13-dihydro-costunolide, desacetylmatricarin, leucodin, achillin, 8α-angeloxy-leucodin and 8α-angeloxy-achillin were isolated. Both latter substances are reported here for the first time. Their NMR data were compared with those of the other guaianolides. The stereochemistry of 3β-hydroxy-11α,13-dihydro-costunolide was discussed and compared with data of the literature.

scholarly journals New Quercetin Triglycoside from the Leaves of Soybean Cultivar ‘Clark’

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984361
Author(s):  
Yoshinori Murai ◽  
Ryoji Takahashi ◽  
Junichi Kitajima ◽  
Tsukasa Iwashina
Keyword(s):  
Glycine Max ◽  
Acid Hydrolysis ◽  
Uv Spectra ◽  
Flavonol Glycosides ◽  
Soybean Cultivar ◽  
Esi Ms ◽  
C Nmr

A new flavonol triglycoside, Quercetin 3- O-α-rhamnopyranosyl-(1→4)-[α-rhamnopyranosyl-(1→6)-β-galactopyranoside], was isolated from the leaves of soybean ( Glycine max) cultivar “Clark” and identified by UV spectra, LC-ESI-MS, acid hydrolysis, and 1H and 13C NMR. The compound was found together with 7 known flavonol glycosides, quercetin 3- O-robinobioside, quercetin 3- O-rutinoside, kaempferol 3- O-rhamnosyl-(1→4)-[rhamnosyl-(1→6)-galactoside], kaempferol 3- O-robinobioside, kaempferol 3- O-rutinoside, isorhamnetin 3- O-robinobioside, and isorhamnetin 3- O-rutinoside.

scholarly journals New Flavonol Glycosides from the Leaves and Flowers of Primula sieboidii

2015 ◽  
Vol 10 (3) ◽  
pp. 1934578X1501000
Author(s):  
Nana Hashimoto ◽  
Ryo Ohsawa ◽  
Junichi Kitajima ◽  
Tsukasa Iwashina
Keyword(s):  
Nmr Spectroscopy ◽  
Acid Hydrolysis ◽  
Flavonol Glycosides ◽  
Chemical Structures ◽  
Primula Sieboldii ◽  
A Minor ◽  
First Time ◽  
C Nmr

Three flavonol glycosides were isolated from the leaves of Primula sieboldii. They were identified as quercetin 3- O-β-[xylopyranosyl-(1→2)- β-glucopyranosyl-(1→6)- β-glucopyranoside] (1), kaempferol 3- O- β-[glucopyranosyl-(1→2)- β-glucopyranosyl-(1→6)- β-glucopyranoside] (2) and kaempferol 3- O- β-[xylopyranosyl-(1→2)- β-glucopyranosyl-(1→6)- β-glucopyranoside] (3). Their chemical structures were determined by UV, 1H and 13C NMR spectroscopy, LC-MS and acid hydrolysis. Compounds 1 and 3 are found in nature for the first time. They were also detected in the flowers, together with two anthocyanins, malvidin 3,5-di- O-glucoside and a minor petunidin dihexoside.

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