NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.

The potential of one- and two-dimensional NMR techniques for the identification of individual sugar residues, their anomeric configuration, interglycosidic linkages, sequencing and the site of any appended group, in establishing the structures of naturally occurring oligosaccharides and glycosides is presented.

[1]  H. Rauvala,et al.  Methylation techniques in the structural analysis of glycoproteins and glycolipids. , 1981, Advances in carbohydrate chemistry and biochemistry.

[2]  D. Gagnaire,et al.  Spectres RMN des Polysaccharides et de leurs Dérivés: Influence des Substituants sur le Déplacement Chimique 13C , 1978 .

[3]  A. Shashkov,et al.  Dependence of 13C chemical shifts on the spatial interaction of protons, and its application in structural and conformational studies of oligo- and poly-saccharides , 1984 .

[4]  R. R. Ernst,et al.  Separation of cross-relaxation and J cross-peaks in 2D rotating-frame NMR spectroscopy , 1987 .

[5]  W. Goux Determination of complex carbohydrate structure using carbonyl carbon resonances of peracetylated derivatives. , 1988, Basic life sciences.

[6]  M. Bernstein,et al.  De novo sequencing of oligosaccharides by proton NMR spectroscopy , 1982 .

[7]  Y. Ohashi,et al.  Structure of zebrinin, a novel acylated anthocyanin isolated from Zebrina pendula , 1987 .

[8]  G. Morris,et al.  EXPERIMENTAL CHEMICAL-SHIFT CORRELATION MAPS FROM HETERONUCLEAR TWO-DIMENSIONAL NMR-SPECTROSCOPY .1. C-13 AND PROTON CHEMICAL-SHIFTS OF RAFFINOSE AND ITS SUBUNITS , 1981 .

[9]  P. Jansson,et al.  Nuclear magnetic resonance and conformational studies on monoacetylated methyl D-gluco- and D-galacto-pyranosides , 1987 .

[10]  M. Adinolfi,et al.  A new class of anthraquinone-anthrone-C-glycosides from asphodelus ramosus tubers. , 1991 .

[11]  Poul Erik Hansen,et al.  Carbon—hydrogen spin—spin coupling constants , 1981 .

[12]  J. Teulon,et al.  Triterpenoid glycosides from the bark of Mimosa tenuiflora. , 1991, Phytochemistry.

[13]  H. Jennings Capsular polysaccharides as human vaccines. , 1983, Advances in carbohydrate chemistry and biochemistry.

[14]  A. Bax,et al.  Application of new, high-sensitivity, 1H-13C-n.m.r.-spectral techniques to the study of oligosaccharides. , 1987, Carbohydrate research.

[15]  J. Buddrus,et al.  Direct Identification of the Carbon Skeleton of Organic Compounds using Double Quantum Coherence 13C‐NMR Spectroscopy. The INADEQUATE Pulse Sequence , 1987 .

[16]  S. Opella,et al.  Detection of 1H homonuclear NOE between amide sites in proteins with 1H15N heteronuclear correlation spectroscopy , 1989 .

[17]  Y. Tomita,et al.  Carbon-13 nmr spectra of saikosaponins A, C, D and F isolated from L. , 1976 .

[18]  Midori Nakamura,et al.  N.m.r. spectral study of α- and β-l-arabinofuranosides , 1989 .

[19]  P. Jansson,et al.  Applications of the CASPER program : comparison between experimental and simulated spectra and an enhancement procedure for the database , 1991 .

[20]  A. Bax,et al.  New NHR Techniques for Structure Determination and Resonance Assignments of Complex Carbohydrates , 1984 .

[21]  D. Uhrín,et al.  Polysaccharides from the roots of the marsh mallow (Althaea officinalis L., var. Rhobusta): dianhydrides of oligosaccharides of the aldose type , 1988 .

[22]  B. Meyer,et al.  Syntheses of disaccharides with (1----4)-beta glycosidic linkages related to the 4- and 6-sulfates and the 4,6-disulfates of chondroitin. , 1991, Carbohydrate research.

[23]  M. Décorps,et al.  Solvent signal suppression in NMR , 1991 .

[24]  P. Gorin,et al.  Structural chemistry of polysaccharides from fungi and lichens , 1983 .

[25]  A. Bax,et al.  Complete proton and carbon-13 assignments of coenzyme B12 through the use of new two-dimensional NMR experiments , 1986 .

[26]  J. Nuzillard,et al.  Two-dimensional extensions of 1D HOHAHA experiments , 1991 .

[27]  R. Newman,et al.  Noroleanane saponins from Celmisia petriei , 1984 .

[28]  Richard R. Ernst,et al.  Elucidation of cross relaxation in liquids by two-dimensional N.M.R. spectroscopy , 1980 .

[29]  P. K. Agrawal,et al.  13C NMR Spectroscopy of lignan and neolignan derivatives , 1985 .

[30]  G. C. Uniyal,et al.  Steroidal glycosides from Agave cantala. , 1990, Phytochemistry.

[31]  L. Poppe,et al.  13C‐selective, 1H‐detected 2D {1H, 13C} correlation spectra of oligosaccharides , 1991 .

[32]  J. Dabrowski Two-dimensional proton magnetic resonance spectroscopy. , 1989, Methods in enzymology.

[33]  D. T. Pegg,et al.  Distortionless enhancement of NMR signals by polarization transfer , 1982 .

[34]  S. Carr,et al.  Aciculatin, a novel flavone-C-glycoside with DNA binding activity from Chrysopogon aciculatis , 1991 .

[35]  T. Ishii Acetylation at O-2 of arabinofuranose residues in feruloylated arabinoxylan from bamboo shoot cell-walls. , 1991, Phytochemistry.

[36]  R. Kasai,et al.  An Additional Sweet Dihydroflavonol Glycoside from Leaves of Engelhardtia chrysolepis, a Chinese Folk Medicine, Huang-qi , 1991 .

[37]  J. Bradbury,et al.  Determination of the structures of trisaccharides by 13C-n.m.r. spectroscopy. , 1984, Carbohydrate research.

[38]  N. Terahara,et al.  Structure of ternatin A1, the largest ternatin in the major blue anthocyanins from clitoria ternatea flowers , 1990 .

[39]  I. Kouno,et al.  Isolation of Neoanisatin Derivatives from the Pericarps of Illicium majus with Other Constituents. , 1991 .

[40]  R. P. Rastogi,et al.  13C NMR Spectroscopy of Flavonoids , 1981 .

[41]  P. Sandford,et al.  The structure of the Aerobacter aerogenes A3(S1) polysaccharide. I. A reexamination using improved procedures for methylation analysis. , 1966, Biochemistry.

[42]  A. Gamian,et al.  Structure elucidation of the core octasaccharide from Citrobacter PCM 1487 with the aid of 500-MHz, two-dimensional phase-sensitive correlated, relayed-coherence transfer, double-quantum, triple-quantum filtered, and N.O.E. 1H-n.m.r. spectra , 1988 .

[43]  A. J. Shaka,et al.  Simplification of NMR spectra by filtration through multiple-quantum coherence , 1983 .

[44]  R. Dwek,et al.  Multiple-step relayed correlation spectroscopy: sequential resonance assignments in oligosaccharides. , 1984, Proceedings of the National Academy of Sciences of the United States of America.

[45]  N. Terahara,et al.  Further structural elucidation of the anthocyanin, deacylternatin, from Clitoria ternatea , 1990 .

[46]  Igor Tvaroŝka,et al.  Anomeric and Exo-Anomeric Effects in Carbohydrate Chemistry , 1989 .

[47]  Y. Terui,et al.  Esterification shifts in carbon-13 NMR spectra of alcohols , 1976 .

[48]  S. Patt,et al.  Attached proton test for carbon-13 NMR , 1982 .

[49]  T. Okuda,et al.  Tannins and Related Polyphenols of Euphorbiaceous Plants. VII. Tirucallins A, B and Euphorbin F, Monomeric and Dimeric ellagitannins from Euphorbia tirucalli L. , 1991 .

[50]  A. Bax,et al.  Long-range proton-carbon-13 NMR spin coupling constants , 1982 .

[51]  D. G. Davis,et al.  Practical aspects of two-dimensional transverse NOE spectroscopy , 1985 .

[52]  G. Adam,et al.  A sulphated triterpenoid saponin from Schefflera octophylla. , 1991, Phytochemistry.

[53]  J. Bella,et al.  Measurement of one‐bond proton‐carbon coupling constants of saccharides , 1991 .

[54]  G. Bodenhausen,et al.  Natural abundance nitrogen-15 NMR by enhanced heteronuclear spectroscopy , 1980 .

[55]  E. Haslinger,et al.  The first structurally confirmed saponin from solidago gigantea: structure elucidation by modern NMR techniques , 1989 .

[56]  S. Mahato,et al.  Triterpenoid saponins discovered between 1987 and 1989. , 1991, Phytochemistry.

[57]  F. Sandberg,et al.  Structural studies on some saponins from Lecaniodiscus cupanioides , 1981 .

[58]  A. Kinghorn,et al.  Abrusoside A: a new type of highly sweet triterpene glycoside , 1989 .

[59]  Ad Bax,et al.  Investigation of complex networks of spin-spin coupling by two-dimensional NMR , 1981 .

[60]  V. Pozsgay,et al.  Carbon-13 n.m.r.-spectral study of l-rhamnose acetates , 1980 .

[61]  T. Goto,et al.  Structure of anthocyanins isolated from purple leaves of Perilla ocimoides L. var. crispa benth and their isomerization by irradiation of light , 1990 .

[62]  G. Michel,et al.  Structure de la chrysantelline B, nouvelle saponine isolée de Chrysanthellum procumbens Rich , 1980 .

[63]  L. Hall,et al.  RESOLUTION AND ASSIGNMENT OF THE 270-MHZ PROTON SPECTRUM OF CELLOBIOSE BY HOMO-NUCLEAR AND HETERONUCLEAR TWO-DIMENSIONAL NMR , 1980 .

[64]  H. Minakata,et al.  Ceroalbolinic Acid, a Common Body Pigment of Three Ceroplastes Scale Insects in Japan. Confirmation of Structure , 1982 .

[65]  R. R. Ernst,et al.  Net polarization transfer via a J-ordered state for signal enhancement of low-sensitivity nuclei , 1980 .

[66]  Y. Mimaki,et al.  Novel Polyhydroxylated Steroidal Saponins from Allium giganteum , 1991 .

[67]  J. Hoffmann,et al.  Characterization of steroidal glycosides from tylophora sylvatica , 1991 .

[68]  B. Sigurskjold,et al.  Conformational dependence of 13C nuclear magnetic resonance chemical shifts in oligosaccharides , 1986 .

[69]  W. Reynolds,et al.  A pulse sequence for establishing carbon-carbon connectivities via indirect 13C-1H polarization transfer modulated by vicinal 1H-1H coupling , 1985 .

[70]  A. Bax,et al.  New n.m.r.-spectroscopic approaches for structural studies of polysaccharides: application to the Haemophilus influenzae type a capsular polysaccharide. , 1987, Carbohydrate research.

[71]  M. Iinuma,et al.  Kaempferol 3-rhamnoside-7-[6-feruloylglucosyl (1----3)rhamnoside] from Asplenium prolongatum. , 1991, Phytochemistry.

[72]  G. Gray,et al.  Quantitative analysis of linkage positions in a complex D-glucan by the reductive-cleavage method. , 1986, Carbohydrate research.

[73]  A. Dell,et al.  F.A.B.-mass spectrometry of carbohydrates. , 1987, Advances in carbohydrate chemistry and biochemistry.

[74]  D. Barron,et al.  Isolation of a novel linalool disaccharide glycoside from raspberry fruit , 1991 .

[75]  C. Unkefer,et al.  The assignment of carbonyl resonances in 13C-n.m.r. spectra of peracetylated mono- and oligo-saccharides containing D-glucose and D-mannose: an alternative method for structural determination of complex carbohydrates. , 1987, Carbohydrate research.

[76]  R. Srivastava,et al.  Bioactive polysaccharides from plants , 1990 .

[77]  S. Svensson,et al.  Mass Spectrometry in Structural Analysis of Natural Carbohydrates , 1974 .

[78]  J. H. Park,et al.  Constituents of a fern, Davallia mariesii Moore. I. Isolation and structures of davallialactone and a new flavanone glucuronide. , 1990, Chemical & pharmaceutical bulletin.

[79]  J. Duus,et al.  Assignment of structures to oligosaccharides produced by enzymic degradation of a beta-D-glucan from barley by 1H- and 13C-n.m.r. spectroscopy. , 1991, Carbohydrate research.

[80]  C. Bush,et al.  Complete structure of the cell surface polysaccharide of Streptococcus oralis ATCC 10557: a receptor for lectin-mediated interbacterial adherence. , 1991, Biochemistry.

[81]  P. Gorin Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Polysaccharides , 1981 .

[82]  Oligosaccharide conformations: Application of NMR and energy calculations , 1990 .

[83]  A. Kinghorn,et al.  A flavan-3-ol glycoside from bark of Plumeria rubra. , 1990 .

[84]  K. Yoshinari,et al.  Flavanone xyloside and lignans from Prunus jamasakura bark , 1990 .

[85]  S. Wijmenga,et al.  Three-dimensional homonuclear TOCSY-NOESY of nucleic acids. Possibilities for improved assignments , 1991 .

[86]  A. Derome The use of n.m.r. spectroscopy in the structure determination of natural products: two-dimensional methods. , 1989, Natural product reports.

[87]  C. Anklin,et al.  Lavandulifolioside a new phenylpropanoid glycoside from stachys lavandulifolia , 1988 .

[88]  V. Wray,et al.  Flavonol triglycosides containing galactose in tea. , 1991, Phytochemistry.

[89]  G. Wulff,et al.  Chemie und Biologie der Saponine , 1973 .

[90]  G. Bodenhausen,et al.  Exploring nuclear spin systems by relayed magnetization transfer , 1982 .

[91]  L. Hall,et al.  An improved chemical-shift-selective filter , 1988 .

[92]  M. Adinolfi,et al.  Glycosides from Muscaricomosum. 5. Structure of muscaroside B , 1984 .

[93]  L. Hall Solutions to The Hidden-Resonance Problem in Proton Nuclear Magnetic Resonance Spectroscopy , 1974 .

[94]  C. Griesinger,et al.  Assignment of carbonyl carbons and sequence analysis in peptides by heteronuclear shift correlation via small coupling constants with broadband decoupling in t1 (COLOC) , 1984 .

[95]  L. Kay,et al.  Three-dimensional NOESY-HMQC spectroscopy of a 13C-labeled protein , 1990 .

[96]  H. Wagner,et al.  Faralatroside and faratroside, two flavonol triglycosides from Colubrina faralaotra , 1981 .

[97]  R. Kaptein,et al.  Nonselective three-dimensional nmr spectroscopy. The 3D NOE-HOHAHA experiment , 1988 .

[98]  D. Ferreira,et al.  Stilbene glycosides from Guibourtia coleosperma: determination of glycosidic connectivities by homonuclear nuclear Overhauser effect difference spectroscopy , 1988 .

[99]  G. Massiot,et al.  Identification and sequencing of sugars in saponins using 2D 1H N.M.R. spectroscopy , 1986 .

[100]  R. Boelens,et al.  Structural studies by 1H/13C two-dimensional and three-dimensional HMQC-NOE at natural abundance on complex carbohydrates , 1990 .

[101]  K. Wüthrich,et al.  Improved spectral resolution in cosy 1H NMR spectra of proteins via double quantum filtering. , 1983, Biochemical and biophysical research communications.

[102]  E. Haslinger,et al.  Isolierung und Struktur der vier Hauptsaponine aus Solidago gigantea var. serotina , 1990 .

[103]  E. Behrman,et al.  N.m.r. assignments of acetyl and trityl groups in derivatized carbohydrates via proton-carbon long-range couplings. , 1986, Carbohydrate research.

[104]  B. Casu,et al.  Carbon-13 and proton magnetic resonance spectra of D-glucose-13C , 1969 .

[105]  M. Iinuma,et al.  A Flavonol Glycoside from Epimedium diphyllum , 1990 .

[106]  P. Stangier,et al.  α‐D‐Glycosyl‐Substituted α,α‐D‐Trehaloses with (1 → 4)‐Linkage: Syntheses and NMR Investigations , 1991 .

[107]  F. G. Vliegenthart,et al.  13C- and 1H-nuclear magnetic resonance spectroscopy of permethylated disaccharides. , 1974, Carbohydrate research.

[108]  T. Nagao,et al.  Studies on the Constituents of Luffa acutangula ROXB. II. Structures of Acutosides H and I, Oleanolic Acid Saponins Isolated from the Seed , 1991 .

[109]  G. Batta,et al.  Easy implementation of homonuclear 1d correlation nmr techniques. Application to oligosaccharioes. , 1991 .

[110]  Christian Pedersen,et al.  Carbon-13 nuclear magnetic resonance data for oligosaccharides , 1984 .

[111]  S. Kadota,et al.  Constituents of the roots of Boerhaavia diffusa L. III. Identification of Ca2+ channel antagonistic compound from the methanol extract. , 1991, Chemical & pharmaceutical bulletin.

[112]  A. Bax Structure determination and spectral assignment by pulsed polarization transfer via long-range 1H13C couplings , 1984 .

[113]  A. Kinghorn,et al.  Use of the selective inept NMR technique in the structure elucidation of (+)-afzelechin-7--β-D-apioside, a bitter principle of , 1987 .

[114]  N. Terahara,et al.  Structures of campanin and rubrocampanin, two novel acylated anthocyanins with p-hydroxybenzoic acid from the flowers of bellflower, Campanula medium L. , 1990 .

[115]  M. Montagu,et al.  A new glycosylated flavonoid, 7-O-α-l-rhamnopyranosyl-4′-O-rutinosylapigenin, in the exudate from germinating seeds of sesbania rostrata , 1989 .

[116]  M. Iinuma,et al.  Phenolic Compounds from Salix sachalinensis , 1990 .

[117]  H. Schneider,et al.  13C NMR shifts and conformations of substituted indans , 1983 .

[118]  M. Baron,et al.  Novel d-glucans obtained by dimethyl sulfoxide extraction of the lichens Letharia vulpina, Actinogyra muehlenbergii, and an Usnea SP☆ , 1988 .

[119]  J. Budzianowski Kaempferol glycosides from Hosta ventricosa. , 1990, Phytochemistry.

[120]  J. Vliegenthart,et al.  PMR and CMR spectroscopy of methyl 2,3,4,6-tetra-O-methyl-α and β-D-glucopyranoside : An application to the identification of partially methylated glucoses , 1973 .

[121]  H. Kessler,et al.  Multi‐dimensional NMR experiments using selective pulses , 1991 .

[122]  Horst Kessler,et al.  Two‐Dimensional NMR Spectroscopy: Background and Overview of the Experiments [New Analytical Methods (36)] , 1988 .

[123]  C. Fenselau Fast Atom Bombardment and Middle Molecule Mass Spectrometry , 1984 .

[124]  A. Chulia,et al.  Flavonol triglycosides from Blackstonia peroliata. , 1990, Phytochemistry.

[125]  A. Bax,et al.  Optimization of two-dimensional homonuclear relayed coherence transfer NMR spectroscopy , 1985 .

[126]  Gary E Martin,et al.  Disentangling coupling and NOE pathways involving poorly resolved proton signals: HMQC‐TOCSY and HMQC‐NOESY , 1990 .

[127]  O. Kamo,et al.  Entada saponin-III, a saponin isolated from the bark of Entada phaseoloides , 1987 .

[128]  R. Gupta,et al.  Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins , 1985 .

[129]  T. Okuda,et al.  Structures of isorugosin E and hirtellin B, dimeric hydrolyzable tannins having a trisgalloyl group☆ , 1991 .

[130]  A. Bax,et al.  An improved method for heteronuclear chemical shift correlation by two-dimensional NMR , 1981 .

[131]  D. Jain,et al.  13C NMR Spectroscopy of Oleanane Triterpenoids , 1992 .

[132]  G. Martin,et al.  INVERSE-DETECTED TWO-DIMENSIONAL NMR METHODS : APPLICATIONS IN NATURAL PRODUCTS CHEMISTRY , 1991 .

[133]  K. Houk,et al.  Transition structures for additions of lithium hydride and methyllithium to ethylene and acetylene , 1985 .

[134]  Y. Knirel,et al.  Stereochemical factors determining the effects of glycosylation on the 13C chemical shifts in carbohydrates , 1988 .

[135]  N K Kochetkov,et al.  A computer-assisted structural analysis of regular polysaccharides on the basis of 13C-n.m.r. data. , 1988, Carbohydrate research.

[136]  T. Goto,et al.  Structure and Molecular Stacking of Anthocyanins—Flower Color Variation , 1991 .

[137]  P. Jansson,et al.  Computer-assisted structural analysis of polysaccharides with an extended version of CASPER using 1H- and 13C-n.m.r. data. , 1989, Carbohydrate research.

[138]  Richard R. Ernst,et al.  Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy , 1983 .

[139]  A. Gronenborn,et al.  Three-dimensional homonuclear Hartmann-Hahn-nuclear overhauser enhancement spectroscopy in H2O and its application to proteins , 1989 .

[140]  J. Vliegenthart,et al.  High-Resolution, 1H-Nuclear Magnetic Resonance Spectroscopy as a Tool in the Structural Analysis of Carbohydrates Related to Glycoproteins , 1983 .

[141]  N. Terahara,et al.  Structure of ternatin D1, an acylated anthocyanin from Clitoria ternatea flowers , 1989 .

[142]  A. Franke,et al.  Quercetin-3-O-α-[2-O-p-hydroxybenzoyl-4-O-p- coumaroylrhamnopyranoside], an aglycone-like flavonol glycoside from Libocedrus bidwillii , 1989 .

[143]  Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame , 1984 .

[144]  H. Nakano,et al.  Davallioside A and B, novel flavan-3-ol derivatives with a γ-lactam, from the rhizomes of Davallia mariesii Moore. , 1990 .

[145]  Ad Bax,et al.  A powerful method of sequential proton resonance assignment in proteins using relayed 15N‐1H multiple quantum coherence spectroscopy , 1989, FEBS letters.

[146]  C. Griesinger,et al.  The Elucidation of the Constitution of Glycopeptides by the NMR Spectroscopic COLOC Technique , 1986 .

[147]  D. Dorman,et al.  Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Chemical and Carbon-13 Proton Couplings in Some Esters and Ethers , 1975 .

[148]  P. K. Agrawal,et al.  A triterpenoid saponin from Polycarpone loeflingiae , 1990 .

[149]  C. Bauvy,et al.  Structural analysis of five lactose-containing oligosaccharides by improved, high-resolution, two-dimensional 1H-n.m.r. spectroscopy☆ , 1989 .

[150]  Michael Barber,et al.  Fast atom bombardment of solids (F.A.B.): a new ion source for mass spectrometry , 1981 .

[151]  Y. Tsuda,et al.  ^ C-Nuclear Magnetic Resonance (NMR) Spectra of O-Acylglucoses. Additivity of Shift Parameters and Its Application to Structure Elucidations , 1980 .

[152]  A. Perlin,et al.  The conformations of furanosides. A 13C nuclear magnetic resonance study , 1979 .

[153]  K. Bock,et al.  A study of 13CH coupling constants in hexopyranoses , 1974 .

[154]  J. Shoolery Recent Developments in 13 C-and Proton-NMR , 1984 .

[155]  J. Pezzuto,et al.  Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius. , 1989, Journal of natural products.

[156]  Stephen P. Miller,et al.  Structural elucidation of alfalfa root saponins by mass spectrometry and nuclear magnetic resonance analysis , 1988 .

[157]  W. Goux,et al.  The assignment of the signals of benzyl methylene carbon atoms in 13C-n.m.r. spectra of per-O-benzylated methyl glycopyranosides , 1988 .

[158]  T. Okuda,et al.  Taxifolin apioside and davuriciin M1, a hydrolysable tannin from Rosa davurica , 1989 .

[159]  M. Becchi,et al.  Structure of a new saponin: chrysantellin A from Chrysanthellum procumbens Rich. , 1979, European journal of biochemistry.

[160]  Takuma Sasaki,et al.  Constituents of holothuroidea. II, Six newly identified biologically active triterpenoid glycoside sulfates from the sea cucumber Cucumaria echinata , 1990 .

[161]  N. Terahara,et al.  Structure of ternatin A2, one of Clitoria ternatea flower anthocyanins having the unsymmetrical side chains , 1990 .

[162]  Richard R. Ernst,et al.  Homonuclear broad band decoupling and two-dimensional J-resolved NMR spectroscopy , 1976 .

[163]  Y. Tsuda,et al.  Syntheses and 1H- and 13C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Methyl Mono-O-tetradecanoyl-a- and β-D-Glucopyranosides , 1980 .

[164]  G. Gray,et al.  Reductive cleavage of glycosides , 1982 .

[165]  S. Patt 2-Dimensional NMR in Carbohydrate Structural Analysis , 1984 .

[166]  H. Günther,et al.  Modern Pulse Methods in High‐Resolution NMR Spectroscopy , 1983 .

[167]  M. Ueda,et al.  Structure of ternatin B1, a pentaacylated anthocyanin substituted on the B-ring asymmetrically with two long chains , 1990 .

[168]  C. Pizza,et al.  Two flavonol glycosides from Chenopodium quinoa. , 1990, Phytochemistry.

[169]  T. Kurokawa,et al.  Studies on Balanites aegyptiaca fruits, an antidiabetic Egyptian folk medicine. , 1991, Chemical & pharmaceutical bulletin.

[170]  A. Zektzer,et al.  Long‐range two‐dimensional heteronuclear chemical shift correlation , 1988 .

[171]  L. Hall,et al.  Two-dimensional J spectroscopy: 1H n.m.r. spectra of mono- and di-saccharides , 1979 .

[172]  A. Bax,et al.  1H and13C Assignments from Sensitivity-Enhanced Detection of Heteronuclear Multiple-Bond Connectivity by 2D Multiple Quantum NMR , 1986 .

[173]  G. Cordell,et al.  One-dimensional proton—carbon correlations for the structure determination of natural products , 1991 .

[174]  Richard R. Ernst,et al.  Multiple quantum filters for elucidating NMR coupling networks , 1982 .

[175]  S. Fesik,et al.  Heteronuclear three-dimensional NMR spectroscopy of the inflammatory protein C5a. , 1989, Biochemistry.

[176]  Gareth A. Morris,et al.  Modern NMR techniques for structure elucidation , 1986 .

[177]  M. Schubert-Zsilavecz,et al.  Sequential analysis of oligosaccharide structures by modern nmr techniques , 1990 .

[178]  G. Englert NMR of carotenoids: novel experimental techniques , 1991 .

[179]  F. Stermitz,et al.  Iridoids. An updated review. Part I , 1990 .

[180]  A. Espada,et al.  Hypoglucaemic triterpenoid saponins from Boussingaultia baselloides , 1990 .