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1.5 Energy level diagram of the relative thermodynamic level of the f...Scheme 1.6 Heavenly blue anthocyanin HBA1 and their derivatives bis‐deacyl‐H...Scheme 1.7 Sketch representing the intramolecular copigmentation in polyacyl...Scheme 1.8 Energy level diagrams of HBA1 (black), HBA2 (blue), and HBA3 (red...Figure 1.5 Mole fraction distribution of heavenly blue anthocyanin.Scheme 1.9 (Left) The polyacylated anthocyanins (Dangles et al. 1993); (Righ...Scheme 1.10 Energy level diagram of the compound HBA1 extended to the mono‐a...Scheme 1.11 2’‐hydroxy‐5’‐methylflavylium and its derived flavanone form.Figure 1.6 (a) Spectral variations after a direct pH jump from pH=1 to pH=8....Scheme 1.12 Illustrating the concept of a timer with reset capacity through ...Scheme 1.13 General scheme of the 6,8 rearrangement. R=Br or R=CH₃ or R=Phen...Figure 1.7 The absorption spectra of equilibrated solutions of the compound ...Scheme 1.14 Qualitative energy level diagram to account for the pH jumps and...Scheme 1.15 ¹H NMR of 6‐bromo‐5,7‐dihydroxyflavylium and its 8‐bromo isomer ...Scheme 1.16 Discrimination, isolation, and 6,8 rearrangement of 6‐bromo‐5,7 ...

      2 Chapter 2Figure 2.1 Origin of the structural diversity in oligomeric PAs: structural ...Figure 2.2 Origin of the structural diversity in oligomeric PAs: B‐type conn...Figure 2.3 Origin of the structural diversity in oligomeric PAs: compounds h...Figure 2.4 Acid hydrolysates of the dimeric proanthocyanidin isolated from A...Figure 2.5 Mayer's PA (procyanidin A2): the terminological origin of A/B‐typ...Figure 2.6 Structures of the tetramers with A‐type linkages.Figure 2.7 Two plausible biosynthetic pathways forming the A‐type structure....Figure 2.8 Retrosynthetic analyses of the A‐type structure.Figure 2.9 Oxidative conversion of the B‐type to the A‐type structure.Figure 2.10 Radical‐mediated oxidative conversion.Figure 2.11 Stepwise construction of the A‐type structure.Figure 2.12 Cascade reaction of 2‐hydroxychalcones with a phloroglucinol der...Figure 2.13 One‐pot formation of the A‐type structure.Figure 2.14 Direct annulation approach to the A‐type structure.Figure 2.15 Early studies on annulation reaction of flavylium 24 with (+)‐ca...Figure 2.16 Annulation reaction by Kraus.Figure 2.17 Asymmetric annulation approach.Figure 2.18 Strategy for stereoselective annulation.Figure 2.19 Synthesis of a 2,4‐dioxy flavan derivative.Figure 2.20 Model study for stereoselective flavan annulation.Figure 2.21 Pettus's diinsininol aglycon synthesis.Figure 2.22 Strategy for monomer synthesis.Figure 2.23 De novo synthesis of the C(7)‐hydroxy monomer unit.Figure 2.24 Total synthesis of procyanidin A2 via flavan annulation.Figure 2.25 Annulation with a free flavan unit and syntheses of procyanidin ...Figure 2.26 DFT calculations of the Wheland intermediates, II and III, deriv...Figure 2.27 Synthesis of cinnamtannin B1 based on the orthogonal activation ...Figure 2.28 Structure of (+)‐selligueain A, its monomeric flavan constituent...Figure 2.29 Orthogonal activation and synthesis of selligueain A.Figure 2.30 Synthesis of a series of dimeric PAs having A‐type structure via...

      3 Chapter 3Figure 3.1 Wild wolf feeding on Alaskan salmonberries.Figure 3.2 Alaska Native youth engage in a workshop featuring simple mobile ...Figure 3.3 (a) Fucus distichus (bladder wrack), a traditionally used phlorot...Figure 3.4 (a) Wild Vaccinium uliginosum (bog blueberry) growing on the Alas...

      4 Chapter 4Figure 4.1 Biosynthetic pathways leading to production of condensed tannins....Figure 4.2 Molecular structure of a condensed tannin polymer.Figure.4.3 Condensed tannins (CTs) influence many aspects of Populus ecology...

      5 Chapter 5Figure 5.1 Representative schematic of the MALDI‐TOF MS process. From left t...Figure 5.2 Natural isotope distribution of procyanidin A2 (a) and procyanidi...Figure 5.3 Chemical structures of PAC trimers, which show 2A:0B‐type interfl...Figure 5.4 Percentage of A‐type interflavan bonds in cranberry PAC oligomers...Figure 5.5 Percentage of A‐type interflavan bonds in apple PAC oligomers fro...Figure 5.6 Deconvolution of MALDI‐TOF MS of 21 different ratios of isolated ...Figure 5.7 Principal component analysis score plot of proanthocyanidins from...Figure 5.8 Principal component analysis score plot of proanthocyanidins from...Figure 5.9 Principal component analysis of proanthocyanidins from apples, cr...

      6 Chapter 6Figure 6.1 Structures of flavan‐3‐ol subunits that give rise to profisetinid...Figure 6.2 Common structural features of PAs: different flavan‐3‐ol subunits...Figure 6.3 Profile of metabolites identified during metabolism of NEPA from ...Figure 6.4 Phenolic reactions during fermentation and oxidation. A‐ring phen...Figure 6.5 Illustration of a rapid approach to proanthocyanidin isolation an...Figure 6.6 HILIC chromatography of (a) pine bark and (b) birch leaf proantho...Figure 6.7 Countercurrent chromatography for preparing depleted and fortifie...Figure 6.8 Products derived from depolymerization reaction of proanthocyanid...Figure 6.9 Identified or proposed

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