Note: Intro -- Contents -- Contributors -- About the Authors -- Pharmacognosy of Black Cohosh: The Phytochemical and Biological Profile of a Major Botanical Dietary Supplement -- 1 Introduction -- 2 Phytochemistry -- 2.1 Cycloartane Triterpenes -- 2.1.1 Structural Diversity -- 2.1.2 Naming System -- 2.1.3 Isolation Techniques -- 2.1.4 Structural Elucidation -- 2.1.4.1 Mass Spectrometry -- 2.1.4.2 Nuclear Magnetic Resonance -- 2.1.4.3 X-Ray Diffraction -- 2.1.5 Dereplication -- 2.1.5.1 Dereplication by LC/MS and LC/ELSD -- 2.1.5.2 Dereplication by NMR -- 2.2 Cimicifugic Acids -- 2.2.1 Structural Characteristics -- 2.2.2 Naming System -- 2.2.3 Isolation Techniques -- 2.2.4 Structural Elucidation -- 2.2.5 Dereplication -- 2.3 Nitrogen-Containing Constituents -- 2.3.1 Structural Diversity -- 2.3.1.1 Primary Metabolites -- Amino Acid Derivatives -- Nucleobase Derivatives -- 2.3.1.2 Secondary Metabolites -- Aporphines -- Betaines -- β-Carbolines -- Cinnamides -- Cholines -- Guanidines -- Isoquinolines -- Protoberberines -- Protopines -- Pyridoxines -- Miscellaneous -- 2.3.2 Structural Elucidation -- 2.3.2.1 Nucleobases and Their Derivatives -- 2.3.2.2 Guanidino Alkaloids -- 2.3.2.3 Hydroxycinnamic Amides -- 2.3.2.4 Choline and Betaine Alkaloids -- 2.3.2.5 Pictet-Spengler Adducts with Tryptamine Derivatives -- 2.3.2.6 Other Alkaloids -- 3 Fingerprinting -- 4 Names and Origin -- 5 Pharmacology -- 5.1 Estrogenic Activity -- 5.2 Prevention of Bone Loss -- 5.3 Potential Anticancer Activity -- 5.4 Stress Relief -- 5.5 Hepatotoxicity -- 6 Clinical Trials -- 7 Concluding Remarks -- References -- A Colorful History: The Evolution of Indigoids -- 1 Introduction -- 1.1 Natural Dyes -- 1.2 Dyes from Plants -- 2 Indigoid Family -- 2.1 Family Presentation -- 2.2 Particular Electronic Effects: Origin of the Color -- 3 Indigo and Its Relatives. , 3.1 Sources and Extraction of Indigo Around the World -- 3.1.1 Japan, Asia -- 3.1.1.1 History -- 3.1.1.2 Extraction Process -- 3.1.2 Europe -- 3.1.2.1 History -- 3.1.2.2 Extraction Procedure -- 3.1.2.3 Chemistry -- 3.1.3 India, South America, and French West Indies -- 3.1.3.1 History -- 3.1.3.2 Extraction Process -- 3.1.3.3 Chemistry -- 3.2 Chemical Synthesis of Indigo -- 3.2.1 The First Syntheses: Baeyer, Drewsen, and BASF -- 3.2.2 New Methods and Mechanism Description -- 4 Tyrian Purple -- 4.1 Legendary History -- 4.2 Extraction -- 4.2.1 Sources -- 4.2.2 Extraction Process -- 4.2.2.1 Central America-South America-Caribbean Sea -- 4.2.2.2 Japan -- 4.2.2.3 Europe -- 4.2.3 Chemistry -- 4.2.3.1 Composition -- 4.2.3.2 Precursors and Biosynthesis -- 4.2.3.3 Chemical Process -- 4.2.3.4 The Case of Vat Dyeing -- 4.3 Chemical Synthesis of Tyrian Purple -- 5 Renewal of Interest of Indigoids in Medicinal Chemistry -- 5.1 Discovery of the Biological Potency of Indirubin -- 5.1.1 Danggui Longhui Wan -- 5.1.2 Mechanism of Action -- 5.2 Royal Purple: A Source of Therapeutic Agents -- 5.2.1 Discovery of the Potential of 6-Bromoindirubin -- 5.2.2 GSK-3β -- 5.2.3 6BIO, a Biological Tool -- 5.2.3.1 Maintenance of Stem Cell Pluripotency -- 5.2.3.2 Antiparasitic Activity -- 5.2.3.3 Anticancer Activity -- 5.2.4 Novel Analogs of 6BIO -- 5.3 Indirubin Synthesis -- 5.3.1 Baeyer Breakthrough -- 5.3.2 Activation of the 2-Position -- 5.3.2.1 The 2-Chloro-3 H -indole-3-one Pathway -- 5.3.2.2 Stabilization of the Intermediate -- 5.3.2.3 Other Isatin Derivatives -- 5.3.3 Indoxyl Pathway -- 5.3.3.1 Stabilization at the 2-Position -- 5.3.3.2 Indoxyl Acetate: The Ultimate Intermediate -- 5.3.4 Biotransformations -- 5.4 Biological Applications of Synthetic Indirubins -- 5.4.1 Creation of Compound Assemblies -- 5.4.2 Indirubin Derivatives -- 5.4.3 7-Bromo-Indirubins. , 5.4.4 New DYRK 1A Inhibitors -- 5.4.5 Other Indirubin Derivatives -- 5.4.6 Conclusion -- 5.5 Glycoside Indigoids -- 5.5.1 Glycosides of Indigos -- 5.5.1.1 The Family of Akashins -- 5.5.1.2 Synthesis of Akashins Derivatives -- 5.5.2 Glycosides of Indirubins -- 5.5.2.1 Indirubin N -Glycosides -- 5.5.2.2 N′ -Glycosylindirubins -- 5.5.2.3 O -Glycosylindirubins -- 5.6 Isoindigo: A Forgotten Family Member -- 5.6.1 Synthesis of Isoindigo -- 5.6.2 Isoindigo in Medicinal Chemistry -- 5.6.2.1 Halogenated Isoindigo -- 5.6.2.2 Glycosylisoindigo -- 5.6.2.3 N -Substituted Isoindigo -- 6 Conclusion -- References -- Bioactive Heterocyclic Natural Products from Actinomycetes Having Effects on Cancer-Related Signaling Pathways -- 1 Introduction -- 2 Collection and Preparation of Actinomycete Strains -- 2.1 Collection of Field Samples for Isolation of Actinomycete Strains Principally from the Chiba Area of Japan -- 2.2 Preparation of an Actinomycete Extract Assembly -- 3 Screening Studies Using the Actinomycete Extract Assembly -- 3.1 Chemical Screening -- 3.2 Cytotoxicity Testing -- 3.3 Screening Tests Targeting Signaling Pathways Related to Cancer Disease -- 3.3.1 TRAIL Signaling (1): Enhancement of Death-Receptor 5 Promoter Activity -- 3.3.2 TRAIL Signaling (2): TRAIL-Resistance Overcoming Activity -- 3.3.3 Wnt Signaling -- 4 Izumiphenazines and Izuminosides -- 4.1 Izumiphenazines -- 4.2 Izuminosides -- 4.3 Effects on Wnt and TRAIL Signaling -- 5 Pyranonaphthoquinones -- 5.1 Pyranonaphthoquinones -- 5.2 Yorophenazine -- 5.3 Yoropyrazone -- 5.4 Effects on TRAIL Signaling -- 6 Azaquinones -- 6.1 Katorazone -- 6.2 Utahmycin and Others -- 6.3 Effects on Wnt and TRAIL Signaling -- 7 Fuzanins -- 7.1 Fuzanins A-D -- 7.2 Fuzanins E-I -- 8 Elmonin -- 9 Actinomycete Metabolites Found in Screening Studies Targeting Cancer-Related Signaling Pathways. , 9.1 Teleocidin with Enhancing Death-Receptor 5 Promoter Activity -- 9.2 Tyrosine Derivatives with TRAIL-Resistance Overcoming Activity -- 9.3 Nonactins, Griseoviridin, and Nocardamines with Wnt Signaling Inhibitory Activity -- 10 Synthesis Aspects -- 10.1 Synthesis of Phenazines -- 10.2 Synthesis of Pyranonaphthoquinones -- References -- Genome Mining: Concept and Strategies for Natural Product Discovery -- 1 Introduction -- 2 Principles of Microbial Natural Product Biosynthesis -- 2.1 Polyketides -- 2.2 Nonribosomal Peptides -- 2.3 Ribosomally Synthesized and Post-translationally Modified Peptides -- 2.4 Terpenes -- 3 Bioinformatic Software Tools -- 4 Discovery of Natural Products from Orphan Pathways -- 4.1 Structure- and Bioactivity-Guided Strategies -- 4.1.1 UV-Based Methods -- 4.1.2 NMR-Based Methods -- 4.1.3 MS-Based Methods -- 4.1.4 Assay-Based Methods -- 4.1.5 One-Strain-Many-Compounds (OSMAC) -- 4.2 Genetic Approaches -- 4.2.1 Mutagenesis and Metabolic Profiling -- 4.2.2 Transcriptional Modulation -- 4.2.3 Heterologous Expression -- 4.2.4 In vitro Reconstitution -- 5 Conclusions and Perspectives -- References.

Note: Intro -- Foreword -- Contents -- Contributors -- About the Authors -- Structure Elucidation of Natural Compoundsby X-Ray Crystallography -- 1 Introduction -- 2 History -- 3 Theoretical Background -- 3.1 Heuristic Introduction -- 3.2 Scattering Theory -- 3.3 Symmetry in Crystals -- 3.4 Crystallographic Resolution -- 3.5 Anomalous Dispersion -- 3.6 The Patterson Function -- 4 Crystal Structure Analysis -- 4.1 Crystallization -- 4.1.1 Crystallization Methodology -- 4.1.2 Crystallization of Membrane Proteins -- 4.1.3 Crystallization of Protein-DNA Complexes -- 4.2 Data Collection -- 4.2.1 X-ray Source -- 4.2.1.1 Laboratory Source -- 4.2.1.2 Synchrotrons -- 4.2.1.3 Compton Source -- 4.2.2 Crystal Mounting -- 4.2.3 Goniometer -- 4.2.4 Detectors -- 4.2.4.1 Imaging Plate Detector -- 4.2.4.2 CCD Detector -- 4.2.4.3 Solid State Detector -- 4.3 Data Reduction -- 4.3.1 Challenges in Data Reduction -- 4.4 Solving the Structure: The Phase Problem -- 4.4.1 Direct Methods -- 4.4.2 Molecular Replacement -- 4.4.2.1 The Search Model -- 4.4.2.2 The Technicalities of Molecular Replacement -- 4.4.3 Experimental Structure Solution -- 4.4.3.1 Multiple Isomorphous Replacement -- 4.4.3.2 Single Isomorphous Replacement -- 4.4.3.3 Anomalous Dispersion -- 4.4.4 Density Modification and NCS Averaging -- 4.5 Model Building and Refinement -- 4.5.1 Least-Squares Refinement -- 4.5.2 Restrained Refinement -- 4.6 Structure Validation -- 5 Results -- 5.1 Cambridge Structural Database -- 5.2 Crystallographic Open Database -- 5.3 Protein Data Bank -- 5.3.1 Nucleic Acid Data Bank -- 5.3.2 Membrane Proteins of Known Three-Dimensional Structure -- 5.3.3 Protein-DNA Complexes -- 5.4 Other Databases -- 6 Special Techniques -- 6.1 Time-Resolved Crystallography -- 6.2 Neutron Crystallography -- 6.3 Electron Crystallography -- 7 Outlook -- References. , Mass Spectrometry in Natural Product Structure Elucidation -- 1 Introduction -- 2 Mass Spectrometric Techniques -- 2.1 Ionization Techniques -- 2.2 Ion Separation Techniques -- 2.3 Analysis of Mixtures -- 2.4 High and Extremely High Masses -- 3 Pentacyclic Triterpenes -- 3.1 Saturated Triterpenes -- 3.2 Triterpenes with Double Bonds -- 3.2.1 Δ12-Oleanenes and -Ursenes -- 3.2.2 Δ12-Lupenes and -Hopenes -- 3.2.3 Δ5-Triterpenes -- 3.2.4 Δ9(11)-Triterpenes -- 3.2.5 Δ14-Taraxerenes -- 3.2.6 Δ13(18)-Oleanene -- 3.2.7 Δ11-Ursenes and -Oleanenes -- 3.2.8 Δ18-Oleanenes and -Friedelenes -- 3.2.9 Δ20- and Δ18(30)-Ursenes -- 3.3 Baueranes, Multifloranes, and Swertanes -- 3.4 Fernane and Arborane Derivatives -- 4 Alkaloids from Vertebrates -- 4.1 Amphibia -- 4.1.1 Toads and Frogs (Anura) -- 4.1.1.1 Biogenic Amines -- 4.1.1.2 Steroidal Alkaloids: Batrachotoxin and Tauromantellic Acid -- 4.1.1.3 Pyrrolidines and Piperidines -- 4.1.1.4 Histrionicotoxins -- 4.1.1.5 Decahydroquinolines -- 4.1.1.6 3,5-Disubstituted Pyrrolizidines and Indolizidines, 4,6-Disubstituted Quinolizidines, and Lehmizidines -- 4.1.1.7 Spiropyrrolizidines -- 4.1.1.8 5,8-Disubstituted Indolizidines and 1,4-Disubstituted Quinolizidines -- 4.1.1.9 Pumiliotoxins (170) and Related Compounds -- 4.1.1.10 Tricyclic Compounds -- 4.1.1.11 Pseudophrynamines -- 4.1.1.12 Epibatidine -- 4.1.1.13 Zetekitoxin AB (Atelopidtoxin) -- 4.1.1.14 Chiriquitoxin -- 4.1.1.15 Alkaloids of Plant Origin Found in Amphibians -- 4.1.1.16 Toad Venoms -- 4.1.2 Salamanders and Newts (Caudata) -- 4.2 Reptiles -- 4.3 Fishes -- 4.3.1 Tetrodotoxin -- 4.3.2 Steroids -- 4.3.3 Ichthyotoxins -- 4.4 Birds -- 4.5 Mammals and Mankind -- 5 Fatty Acids and Lipids -- 5.1 Fatty Acids -- 5.1.1 Saturated and Unsaturated Fatty Acids -- 5.1.2 Furan Fatty Acids -- 5.2 Glycerol Derivatives -- 5.2.1 Glycerol Ethers from Archaebacteria and Sediments. , 5.2.2 Triglycerides -- 5.2.3 Glycerophospholipids -- 5.3 Lipidomics -- 6 Carbohydrates -- 6.1 Monosaccharides -- 6.2 Di-, Oligo-, and Polysaccharides -- 6.3 Glycosides -- 7 Amino Acids, Peptides, and Proteins -- 7.1 Amino Acids -- 7.2 Peptides -- 7.2.1 Linear Peptides -- 7.2.2 Cyclopeptides and Cyclodepsipeptides -- 7.3 Proteomics -- 8 Nucleosides, Nucleotides, and Nucleic Acids -- 8.1 Nucleobases, Mono-Nucleosides, and Mono-Nucleotides -- 8.2 Di- and Oligo-Nucleotides -- 8.3 Polynucleotides, DNA, and RNA -- 8.4 Interaction with Other Compounds -- 9 Mass Spectra Collections -- 9.1 General -- 9.2 Alkaloids -- 9.3 Drugs, Poisons, Pesticides, and Pollutants -- 9.4 Flavors and Fragrances -- 9.5 Geo- and Petrochemicals -- 9.6 Lipids -- 9.7 Steroids -- 9.8 Terpenes -- 10 Addendum -- References -- Nuclear Magnetic Resonance in the Structural Elucidation of Natural Products -- 1 Introduction -- 2 Dereplication: Distinguishing Between New and Known Natural Products -- 3 Quantitative NMR -- 4 Using 2D NMR to Determine Skeletal Structures of Natural Products -- 5 Avoiding Getting the Wrong Skeletal Structure -- 6 Determination of Configuration and/or Conformation of Natural Products -- 7 An Example of a Solved Structure: Kauradienoic Acid -- 7.1 HSQC Data -- 7.2 COSY and TOCSY Data -- 7.3 HMBC Data -- 7.4 General Molecular Assembly Strategy -- 7.5 A Specific Molecular Assembly Procedure -- 7.6 Determination of Overall Stereochemistry and Proton Chemical Shift Assignments -- 8 Computer-Assisted Structure Elucidation -- 8.1 Guyanin -- 8.2 T-2 Toxin -- 8.3 Kauradienoic Acid -- 9 The Effect of Dynamic Processes on the Appearance of NMR Spectra of Natural Products and Other Organic Compounds -- 10 The Relative Advantages and Disadvantages of Different Pulse Sequences -- 11 Liquid-Chromatography-NMR -- 12 Probe Choices. , 12.1 Essential Probe Features for Natural Product Research -- 12.2 Ambient-Temperature Probes -- 12.3 Cryogenically Cooled Probes -- 12.4 Microprobes -- 13 A Fully Automated Setup of 2D NMR Experiments for Organic Structure Determination -- 14 Parameter Choices for Acquisition and Processing of 1D and 2D NMR Spectra -- 14.1 Basics of NMR Data Acquisition -- 14.1.1 Sampling Rate -- 14.1.2 Analog to Digital Conversion -- 14.1.3 Digital Oversampling -- 14.1.4 Quadrature Detection -- 14.1.5 Fold-in Peaks -- 14.1.6 Analog Versus Digital Filters -- 14.2 Recommended Acquisition and Processing Parameters for 1D Spectra -- 14.2.1 Spectral Widths -- 14.2.2 Number of Data Points and Acquisition Times -- 14.2.3 Number of Scans (Transients) -- 14.2.4 Zero Filling and Data Point Resolution -- 14.2.5 Pulse Widths and Delay Times -- 14.2.6 Apodization (Weighting) Functions -- 14.2.7 13C Spectral Editing -- 14.3 Basics of 2D NMR -- 14.3.1 General Features of 2D NMR Sequences -- 14.3.2 Homonuclear and Heteronuclear 2D NMR Spectra -- 14.3.3 Absolute-Value Versus Phase-Sensitive Spectra -- 14.3.4 Phase Cycling Versus Gradient Selection -- 14.3.5 Acquisition Times and Relaxation Delays -- 14.3.6 Number of Time Increments, Forward Linear Prediction, and Zero Filling -- 14.3.7 Number of Scans -- 14.3.8 Apodization Functions -- 14.3.9 Data Point Resolution in 2D NMR Spectra -- 14.3.10 Shaped Pulses and Selective 1D Analogues of 2D NMR Spectra -- 14.4 Recommended Acquisition and Processing Parameters for Commonly Used 2D Experiments and Selective 1D Experiments -- 14.4.1 COSY and TOCSY Experiments -- 14.4.1.1 Gradient-Selected COSY (Absolute-Value Mode) -- 14.4.1.2 Gradient-Selected Double Quantum Filtered COSY (Phase Sensitive) -- 14.4.1.3 TOCSY or Z-TOCSY* (Phase-Sensitive) -- 14.4.2 NOESY and ROESY Experiments -- 14.4.2.1 NOESY (Phase-Sensitive). , 14.4.2.2 ROESY *(Phase-Sensitive) -- 14.4.3 HMQC, HSQC, HMBC, and H2BC Experiments -- 14.4.3.1 Gradient-Selected HMQC (Absolute-Value) -- 14.4.3.2 Gradient-Selected HSQC* (With or Without 13C Spectral Editing) -- 14.4.3.3 Gradient-Selected HMBC (Absolute-Value) -- 14.4.3.4 Gradient-Selected HMBC (Mixed-Mode Processing)* -- 14.4.3.5 Gradient-Selected H2BC (Phase-Sensitive) -- 14.4.4 Selective 1D Experiments -- 14.4.4.1 1D TOCSY* -- 14.4.4.2 1D NOESY or ROESY* -- 15 Conclusions -- References -- Vibrational Circular Dichroism Absolute Configuration Determination of Natural Products -- 1 Introduction -- 2 A Brief History -- 3 Experimental Considerations -- 3.1 VCD-FT Spectrophotometer -- 4 Theoretical Calculations -- 4.1 Fundamental Parameters -- 4.1.1 Dipolar and Rotational Strengths in VCD Transitions -- 4.1.2 Computational Calculations of Dipolar and Rotational Strengths -- 4.2 Density Functional Theory -- 4.2.1 Hybrid Functionals and Basis Set -- 4.3 Conformational Optimization and Graphical VCD Methods for Absolute Configuration Assignment -- 5 Studies of Natural Products and Some Chiral Structurally Related Molecules -- 5.1 Fundamentals in the Interpretation of VCD Spectra -- 5.1.1 The Local Model -- 5.1.2 Normal Versus Local Mode Assignment -- 5.1.3 H-bonding and Solvent Effects. The Robust Mode Concept -- 5.1.4 Symmetry and Conformation -- 5.2 Assignment of Absolute Configurations of Terpenes, Aromatic Molecules, and other Natural Compounds -- 5.2.1 Monoterpenes -- 5.2.2 Sesquiterpenes -- 5.2.3 Diterpenes and Meroterpenoids -- 5.2.4 Triterpenes -- 5.2.5 Aromatic Molecules -- 5.2.6 Other Natural Products -- 6 Concluding Remarks -- References -- The Series "Progress in the Chemistry of Organic Natural Products": 75 Years of Service in the Development of Natural Product Chemistry -- 1 Introduction -- 2 László Zechmeister: Editor from 1938 to 1969. , 2.1 Previous History: Phytochemistry in Hungary.