Deuterium-induced differential isotope shift carbon-13 NMR. 1. Resonance reassignments of mono- and disaccharides

Pfeffer, Philip E.; Valentine, Kathleen M.; Parrish, Frederick W.

doi:10.1021/ja00499a036

Cited by 326 publications

(125 citation statements)

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“…The assignments of the cyclodextrins and dextran T-10 in Table 1 are based on carbon-13 shifts reported by Colson,et al (16), while those for glucose (1) follow Pfeffer et al (17) and Dwek and co-workers (18). Several assignments have been proposed for maltose (2) and maltotriose (3) (16,19,20), but the experimental results obtained suggest a minor adjustment to the assignment of maltose, and a fairly radical reinterpretation of the 'During the reparation of this paper Heyraud el ,a/.…”

Section: Resultsmentioning

confidence: 96%

Experimental chemical shift correlation maps from heteronuclear two-dimensional nuclear magnetic resonance spectroscopy. II: Carbon-13 and proton chemical shifts of a-D-glucopyranose oligomers

Morris¹,

Hall²

1982

Can. J. Chem.

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Double Fourier transform ("2D") nmr methods allow the simultaneous measurement of proton and carbon-13 chemical shifts for each directly bonded carbon–proton pair in a molecule. As well as greatly increasing the number of different resonances that may be distinguished in the spectra of complex systems, the measurement of correlated proton and carbon-13 shifts allows the otherwise inaccessible proton shifts to be determined, and facilitates the assignment of conventional proton and carbon-13 spectra. Results are presented for glucose, maltose, maltotriose, α-cyclodextrin, β-cyclodextrin, and dextran T-10; reassignments are proposed for the carbon-13 spectra of maltose and maltotriose.

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Section: Resultsmentioning

confidence: 96%

Experimental chemical shift correlation maps from heteronuclear two-dimensional nuclear magnetic resonance spectroscopy. II: Carbon-13 and proton chemical shifts of a-D-glucopyranose oligomers

Morris¹,

Hall²

1982

Can. J. Chem.

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“…To the best of our knowledge, except for a publication in which the presence of eudesmol isomers from C. trichotoma wood 11 has been recorded, there have been no other reports of any similar chemical investigation in the literature. In this paper we describe the isolation and structure elucidation of the known compounds: β-sitosterol, sitosterol-β-D-glucoside 12 , oleanolic acid 13 , allantoin 14 , sucrose 15 , α-cadinol 16 , oncocalyxone A 8 , cordiachrome C 5 , and a new sesquiterpene, trichotomol (1). Although cordiachrome C (2) had been previously isolated from C. millenii, only the partial 1 H NMR data was provided but some doubt about its stereochemistry 5 has remained.…”

Section: Introductionmentioning

confidence: 99%

Trichotomol, a New Cadinenediol from Cordia trichotoma

Menezes¹,

Lemos²,

Silveira³

et al. 2001

J. Braz. Chem. Soc.

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Um novo sesquiterpeno, nomeado trichotomol e compostos conhecidos como cordiacromo C, α-cadinol, ácido oleanólico, oncocalyxona A, β-sitosterol, glicosídeo do β-sitosterol, alantoína e sacarose foram isolados a partir do extrato etanólico do cerne de Cordia trichotoma. Suas estruturas foram determinadas por análises espectroscópicas e comparação com dados publicados para compostos estruturalmente relacionados.A new sesquiterpene, named trichotomol, and known compounds cordiachrome C, α-cadinol, oleanolic acid, oncocalyxone A, β-sitosterol, β-sitosterol-β-D-glucoside, allantoin and sucrose were isolated from the heart wood ethanol extract of Cordia trichotoma. Their structures were assigned unambiguously by spectroscopic analyses and comparison with the published data for structurally related compounds.

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“…To locate hydroxyl groups on the benzene ring, the 13 C-NMR of 1 was carefully measured in CD 3 OH and CD 3 OD, respectively. The deuterium isotope effects [3][4][5] were observed at 2-(0.10 ppm) and 4-positions (0.10 ppm) when measured in each solvent. The shift observed for the 3-position (0.18 ppm) were thought to be due to the g-effects of the two vicinal hydroxyl groups.…”

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confidence: 95%

Ardisiphenols A-C, Novel Antioxidants from the Fruits of Ardisia colorata.

Sumino

Sekine

Ruangrungsi

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Novel alk(en)ylphenols, named ardisiphenols A-C (1-3) were isolated from the fruits of Ardisia colorata, together with known alk(en)ylresorcinols (4-6). Their structures were determined by the NMR and MS/MS analyses. All compounds showed scavenging activities towards 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and cytotoxicities against murine breast cancer cell line, FM3A.Key words Ardisia colorata; Myrsinaceae; ardisiphenol; alk(en)ylphenol; cytotoxicity Ardisia colorata ROXB. (Myrsinaceae) is used as a folk medicine for liver disease, cough and diarrhoea in Thailand. A previous phytochemical investigation on this species resulted in the isolation of rapanone and ilexol.1) No further detailed study has been reported. In the course of the screening for antioxidants in Thai medicinal plants, A. colorata showed a scavenging activity towards DPPH radical in TLC autographic assay.2) This paper deals with the structure elucidation of the newly isolated alk(en)ylphenols and known alk(en)ylresorcinols, and their cytotoxicities against murine breast cancer cell line, FM3A.The 75% ethanol extract of the dried fruits of A. colorata (500 g) was partitioned by successive extraction with organic solvents of increasing polarity. Initially the attention was paid to the antioxidative compounds in n-hexane fraction, then repeated silica gel chromatographies (CHCl 3 -MeOH, n-hexaneAcOEt) and HPLC (MeOH-0.2% AcOH, 85 : 15) were performed to give new compounds 1-3 (0.043, 0.084, 0.058%, respectively) and known compounds 4-6 (0.022, 0.053, 0.037%, respectively). The six compounds were all positive for ferric chloride test and showed scavenging activities towards DPPH radical in TLC autographic assay.Ardisiphenol A (1) has a molecular formula C 23 H 38 O 4 from high-resolution (HR)-FAB-MS. The 1 H-NMR spectrum of 1 showed signals of two meta coupled aromatic protons at d 6.13 (d, Jϭ2.7 Hz, H-5) and 6.21 (d, Jϭ2.7 Hz, H-3), and signals due to a long alkyl side chain at d 0.89 (3H, t, Jϭ7.0 Hz, H-15Ј), 1.28 (24H, overlapped, H-3Ј--14Ј), 1.50 (homobenzyl 2H, m) and 2.35 (benzyl 2H, t, Jϭ7.3 Hz). The 13 C-NMR spectrum of 1 showed signals for tetra-substituted benzene at d 131. 6, 150.6, 102.4, 156.5, 107.9 and 137.4, and signals for an alkyl side chain which were assigned as shown in Fig. 1 by two-dimensional (2D)-NMR spectra. Signals of acetoxyl group were also observed at d 2.25 (3H, s), 20.5 (OCOCH 3 ) and 171.6 (OCOCH 3 ). Electron impact (EI)-MS showed a base peak at m/z 139 corresponding to a benzylic fragmentation of deacetylated ion of 1 and an intense peak of deacetylated ion of 1 at 335 (MϪAc) ϩ . Therefore, it was suspected that 1 was a benzene derivative tetra-substituted by two hydroxyl groups, an acetoxyl group and an unbranched C 15 alkyl chain. However, the position of the acetoxyl group was not deduced from above experimental data and the nuclear Overhauser effect (NOE) enhancement was not observed between the acetyl group and any other protons. To locate hydroxyl groups on the benzene ring, the 13 C-NMR of 1 was caref...

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Deuterium-induced differential isotope shift carbon-13 NMR. 1. Resonance reassignments of mono- and disaccharides

Cited by 326 publications

References 7 publications

Experimental chemical shift correlation maps from heteronuclear two-dimensional nuclear magnetic resonance spectroscopy. II: Carbon-13 and proton chemical shifts of a-D-glucopyranose oligomers

Experimental chemical shift correlation maps from heteronuclear two-dimensional nuclear magnetic resonance spectroscopy. II: Carbon-13 and proton chemical shifts of a-D-glucopyranose oligomers

Trichotomol, a New Cadinenediol from Cordia trichotoma

Ardisiphenols A-C, Novel Antioxidants from the Fruits of Ardisia colorata.

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