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 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.

scholarly journals Synthesis of cis, cis-1,3,5-trisubstituted cyclohexane based chelators with polyfunctional pendant arms

2005 ◽  
Vol 2005 (1) ◽  
pp. 43-45 ◽  
Author(s):  
Minati Baral ◽  
B.K. Kanungo ◽  
Peter Moore
Keyword(s):  
Schiff Base ◽  
Nmr Spectroscopy ◽  
Organic Compounds ◽  
Elemental Analysis ◽  
H Nmr ◽  
Benzenetricarboxylic Acid ◽  
New Compounds ◽  
Pendant Arms ◽  
C Nmr

Some novel organic compounds of the type: cis, cis-1,3,5-tris(X)cyclohexane, where X= –CONH(CH2)2NH2, –CONH(CH2)3NH2, –CONH(CH2)2NCH –C6H4OH, CONH(CH2)3NCHC6H4OH, which are expected to function as potential polydentate chelators have been synthesised from 1,3,5-benzenetricarboxylic acid through multi-steps reactions. 1,3,5-benzenetricarboxylic acid was reduced to cis, cis-1,3,5-tris(ethylcarboxylate)cyclohexane, which on reaction with excess of 1,2-diaminoethane and 1,2-diaminopropane afforded two new compounds. Condensation of the obtained derivatives with three equivalents of salicylaldehyde resulted the formation of two new Schiff base compounds. All the compounds were characterised by a combination of elemental analysis, mass, IR, UV-Vis, 1H NMR and 13C NMR spectroscopy.

Assignment of cis-trans Geometry in Diastereomeric 2-Benzyl-4-methyl-1,3,2-dioxaphosphorinans and their 2-Oxo- and 2-Seleno-Derivatives

1975 ◽  
Vol 30 (9-10) ◽  
pp. 710-715 ◽  
Author(s):  
W. J. Stec ◽  
K. Lesiak ◽  
D. Mielczarek ◽  
B. Stec
Keyword(s):  
Nmr Spectroscopy ◽  
Spin Coupling ◽  
Coupling Constant ◽  
Spin Coupling Constant ◽  
Geometrical Isomers ◽  
Benzyl Halides ◽  
New Compounds ◽  
Cis And Trans ◽  
Spin Spin Coupling ◽  
C Nmr

MICHAELIS-ARBUSOV reaction of diastereoisomeric 2-methoxy-4-methyl-1,3,2-dioxaphosphorinans with benzyl halides is non-stereospecific. Cis- and trans-2-benzyl-2-oxo-4-methyl-1,3,2-dioxaphosphorinans were separated and analysed by means of IR, 31P and 13C NMR spectroscopy. 2-Benzyl-2-seleno-4-methyl-1,3,2-dioxaphosphorinans were synthesized and stereospecifically converted to 2-oxo-analogues. Stereochemistries are assigned to the geometrical isomers of all new compounds described in this paper. Application of direct spin-spin coupling constant values for structural elucidation is emphasized.

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'.

Kondensationsreaktionen von Trifluornitrosomethan CF3NO mit Sulfanilamid H2NC6H4SO2NH2-Darstellung von CF3NNC6H4SO2NH2, CF3NNC6H4SO2NNCF3, CH3C(O)N(H)C6H4SO2NNCF3 und CF3C(0)N (H)C6H4SO2NH2 / Condensation Reactions of Trifluoronitrosomethane CF3NO with Sulfanilamide H2NC6H4SO2NH2- Preparation of CF3NNC6H4SO2NH2, CF3NNC6H4SO2NNCF3, CH3C(0)N(H)C6H4SO2NNCF3 and CF3C(0)N (H)C6H4SO2NH2

1997 ◽  
Vol 52 (5) ◽  
pp. 647-654 ◽  
Author(s):  
Rolf Minkwitz ◽  
Jens Jakob ◽  
Andreas Winter
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Protecting Groups ◽  
Amino Group ◽  
Condensation Reactions ◽  
New Compounds ◽  
C Nmr

Abstract We report the condensations of trifluoronitrosom ethane with sulfanilamide. The new compounds p-trifluorom ethylazophenylsulfonamide CF3NNC6H4SO2NH2, p-trifluorom ethylazosulfonyltrifluorom ethylazobenzole CF3NNC6H4SO2NNCF3 and p-trifluoromethylazosulfonylacetanilide CH3C(O)N(H)C6H4SO2NNCF3 were characterized by elemental analysis, IR, Raman, mass, 1H , 19F and 13C NMR spectroscopy. In addition we present our approach to the preparation of p-trifluorom ethylazosulfonylaniline H2NC6H 4SO2NNCF3 by using protecting groups for the amino group.

Syntheses and Characterization of 1-Haloazagermatranes

2001 ◽  
Vol 56 (2) ◽  
pp. 137-140 ◽  
Author(s):  
Pavel L. Shutov ◽  
Sergey S. Karlov ◽  
Jörg Lorberth ◽  
Galina S. Zaitseva
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Molecular Composition ◽  
High Yield ◽  
Elemental Analyses ◽  
New Compounds ◽  
C Nmr

Abstract Germanium, Azagermatranes The reaction of tris(dimethylamino)halogermanes, (Me2N)3GeHal (7, Hal = Cl; 8 , Hal = Br), with tris(2-aminoethyl)amines, N(CH2CH2NHR)3 (5, R = H; 6 , R = Me), yield l-halo-N,N',N"-azagermatranes (1, X = Cl, R = H; 2, X = Br, R = H; 3, X = Cl, R = Me; 4, X = Br, R = Me). Treatment of 4 with n-butyllithium affords l-n-butyl-N,N',N"-trimethylazagermatrane (14) in high yield. Reactions of n-BuLi with 7 or (Me2N)4Ge (13) lead to the formation of (Me2N)3Ge-n-Bu (15). On treatment of 15 with 5 the 1 -n-butylazagermatrane 16 was obtained. The molecular composition and the structures of all new compounds were established by elemental analyses, 1H and 13C NMR spectroscopy and mass spectrometry.

Structural and spectral study of coordination of 4,4′-dimethoxy-2,2′-bipyridine toward Zn(II) and Cd(II) containing thiocyanato or azido ligands

2016 ◽  
Vol 71 (9) ◽  
pp. 959-965 ◽  
Author(s):  
Farzin Marandi ◽  
Keyvan Moeini ◽  
Hadi Amiri Rudbari
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
Octahedral Geometry ◽  
Distorted Octahedral Geometry ◽  
X Ray ◽  
X Ray Crystallography ◽  
Distorted Octahedral ◽  
Ft Ir ◽  
New Compounds ◽  
C Nmr

AbstractThree new compounds of zinc(II) and cadmium(II) with the ligand 4,4′-dimethoxy-2,2′-bipyridine (4,4′-dmo-2,2′-bpy), including cis-[Zn(4,4′-dmo-2,2′-bpy)2(SCN)2] (1), cis-[Cd(4,4′-dmo-2,2′-bpy)2(SCN)2] (2), and [Cd3(4,4′-dmo-2,2′-bpy)3(N3)5(OAc)]n (3), have been obtained as white single crystals by the branched tube method and characterized by elemental analysis, FT-IR and 1H, 13C NMR spectroscopy, and X-ray crystallography. Single-crystal structure analyses of the isostructural complexes 1 and 2 showed distorted octahedral geometry for zinc(II) and cadmium(II) with ZnN6 and CdN6 environments. Complex 3 reveals a rare coordination polymer containing octahedrally coordinated cadmium(II) expanding to chains by two different bridging modes, including Cd‒O‒C‒O‒Cd and Cd‒N‒Cd.

Synthesis and Structural Characterization of Metal Complexes of 2-Formylpyrrole 4N-Methylthiosemicarbazone (4ML1) and 2-Acetyl- pyrrole 4N-Methylthiosemicarbazone (4ML2). The X-Ray Crystal Structures of [Ni(4ML1-H)2], [Pd(4ML1-H)2] and [Cd(4ML2)2I2]

2001 ◽  
Vol 56 (3) ◽  
pp. 219-228 ◽  
Author(s):  
Ruben Alonso ◽  
Elena Bermejo ◽  
Rosa Carballo ◽  
Alfonso astiñeiras ◽  
Teresa Pérez
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Structural Characterization ◽  
X Ray ◽  
Group 12 ◽  
New Compounds ◽  
Group 10 Metals ◽  
C Nmr

Abstract Reaction of 4N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazinecarbothioamide (4ML1 and 4N-methyl-2-[1-(pyrrol-2-yl)-ethylidene]hydrazine carbothioamide (4ML1) with zinc(II), cadmium(II) and mercury(II) halides afforded complexes with formulas [M(L)X2] [(L; M; X) =(4ML1; Cd; Cl) (4), (4ML1; Hg; Cl, Br, I) (7 - 9), (4ML2; Cd; Cl) (17), (4ML2; Hg; Cl, Br, I) (20 - 22)] or [M(L)2X2] [(L; M; X) = (4ML1; Zn; Cl, Br, I) (1 - 3), (4ML1; Cd; Br, I) (5, 6), (4ML2; Zn; Cl, Br, I) (14 - 16), (4ML2; Cd; Br, I) (18, 19)]. Reaction of 4ML1 with salts of copper(II), nickel(II), palladium(II) and platinum(II) afforded complexes of formula [M(4ML1-H)2] (10 -13). Crystals of 11, 12 and 19 were studied by X-ray diffractometry, and all new compounds were characterized by elemental analysis, mass spectrometry, and IR, electronic and 1H and 13C NMR spectroscopy and, when pertinent and allowed by the solubility of the compound, 113Cd or 199Hg NMR spectroscopy. In the complexes of Group 12 metals, both ligands are neutral and S-monodentate. In the complexes of copper or Group 10 metals, 4ML1 is monodeprotonated and S,N-bidentate.

Cardenolide aus Ornithogalum nutans (2 n = 30), 2. Mitteilung+ / Cardenolides from Ornithogalum nutans (2 n = 30), Part 2+

1992 ◽  
Vol 47 (10) ◽  
pp. 1459-1468 ◽  
Author(s):  
Roland Ferth ◽  
Andreas Baumann ◽  
Klaus K. Mayer ◽  
Wolfgang Robien ◽  
Brigitte Kopp
Keyword(s):  
Nmr Spectroscopy ◽  
Acid Hydrolysis ◽  
Column Chromatography ◽  
Relationship Of ◽  
Hydrolysis Of ◽  
C Nmr

From bulbs of Ornithogalum nutans L. (2 n = 30) nineteen cardenolides were isolated by column chromatography and TLC. Thirteen substances were structurally elucidated as glycosides of Strophanthidin, Sarmentosigenin, Sarmentogenin, Bipindogenin, 2a-Hydroxy-bipin-dogenin, Syriogenin, 7a-Hydroxy,12-oxo,8β,14β-epoxy-uzarigenin, 3β,11β-Dihydroxy,12-oxo, 18-nor-5 α-card-13-enolide, 3β, 11β-Dihydroxy, 12-oxo, 18-nor-5 α-carda-13,20(22)-dienolide, mainly by means of 1H, 13C NMR spectroscopy, FAB-MS and identification of the sugar moieties by GLC after acid hydrolysis of the cardenolides. Six of these glycosides were identified by cochromatography (HPLC and TLC) with authentic samples. The results obtained were discussed with regard to the close botanical relationship of Ornithogalum nutans L. and Ornithogalum boucheanum (KUNTH) ASCHERS.

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