Recent Advances in Natural Products Analysis

Description

Recent Advances in Natural Products Analysis is a thorough guide to the latest analytical methods used for identifying and studying bioactive phytochemicals and other natural products. Chemical compounds, such as flavonoids, alkaloids, carotenoids and saponins are examined, highlighting the many techniques for studying their properties. Each chapter is devoted to a compound category, beginning with the underlying chemical properties of the main components followed by techniques of extraction, purification and fractionation, and then techniques of identification and quantification. Biological activities, possible interactions, levels found in plants, the effects of processing, and current and potential industrial applications are also included. Focuses on the latest analytical techniques used for studying phytochemical and other biological compoundsAuthored and edited by the top worldwide experts in their fieldDiscusses the current and potential applications and predicts future trends of each compound group Front Matter Copyright Dedication Contributors Foreword by Satyajit Sarker Foreword by Geoffrey Cordell Preface Introduction to natural products analysis Introduction Extraction of natural products Solvent extraction (SE) Solid-phase extraction (SPE) Supercritical fluid extraction (SFE) Microwave-assisted extraction (MAE) Ultrasonic-assisted extraction (UAE) Pulsed electric field (PEF) extraction Enzyme-assisted extraction (EAE) Pressurized liquid extraction (PLE) Isolation and purification of natural products Structural elucidation of the phytochemicals Ultraviolet-visible spectroscopy IR spectroscopy NMR spectroscopy Mass spectrometry Applications of natural products and phytochemicals Conclusion 1.1IntroductionNatural products are broadly defined as anything produced by life (e.g., wood, silk, bioplastics, cornstarch, References Analysis of monophenols Introduction Phytochemistry of representative monophenols Origins and biodegradation of monophenols Biological activity of monophenols Toxicity of monophenols Current and potential industrial applications of monophenols Techniques of extraction, purification, and fractionation Techniques of identification and quantification Levels found in plant/food-based plants Effect of food processing Trends and concluding remarks References Analysis of polyphenolics References Phytochemistry of the flavonoids Biological activities of flavonoids Current and potential industrial applications of flavonoids Possible interactions of flavonoids Techniques of extraction, purification, and fractionation of flavonoids Techniques of identification and quantification of flavonoids Levels founds of flavonoids in plants/food-based plants Effects of food processing in flavonoids Trends and concluding remarks 3.1.1Phytochemistry of the flavonoidsPolyphenols are a group of secondary plant metabolites comprising more than 8000 compound References Introduction of glycosidic derivatives of flavonoids Phytochemistry and classification of glycosidic derivatives of flavonoids Main representatives of glycosidic derivatives of flavonoids Biological activities of glycosidic derivatives of flavonoids Techniques of extraction and purification of glycosidic derivatives of flavonoids Techniques of identification and quantification of glycosidic derivatives of flavonoids Levels founds of glycosidic derivatives of flavonoids in foods/plants Effects of food processing in glycosidic derivatives of flavonoids Pharmaceutical applications of glycosidic derivatives of flavonoids Medicinal uses Uses as food Tanning of leather Natural plant pigments Main conclusions 3.2.1Introduction of glycosidic derivatives of flavonoidsIn plants, the phenolic compounds are among the major classes of seco References Phytochemistry of isoflavonoids Properties of isoflavonoids Biological activities of isoflavonoids Current and potential industrial applications of isoflavonoids Possible interactions properties of isoflavonoids Techniques of extraction, purification, and fractionation of isoflavonoids Techniques of identification and quantification of isoflavonoids Levels found of isoflavonoids in plants/food-based plants Effects of food processing in phytochemicals Trends and concluding remarks 3.3.1Phytochemistry of isoflavonoidsAmong the subclasses of flavonoids, isoflavonoids consist of a 15-carbon (C6-C3-C6) back References Further reading Introduction of lignans and flavonolignans Main representative of lignans and flavonolignans Biological activities of lignans and flavonolignans Therapeutic perspectives of flavonolignans Current and potential industrial applications of lignans and flavonolignans Techniques of extraction, purification, and fractionation of lignan and flavonolignans Classical methods of extraction of lignans Microwave-assisted extraction Use of HPLC for the characterization of SDG Techniques for characterization of lignans Flow diagram for the extraction of lignans from flaxseed Fractionation of lignans Techniques of identification and quantification of lignan and flavonolignans Effect of processing and storage on lignans and flavonolignans content in foods Level of lignans and flavonolignans in food/plants-based products Trends and concluding remarks 3.4.1Introduction of lignans and flavonolignansThe term ``Lignan´´ is used to designate the group of dimeric phenylp References Phytochemistry of stilbenoids Biological activities of stilbenoids Current and potential industrial applications of stilbenoids Possible interactions of stilbenoids Techniques of extraction, purification, and fractionation of stilbenoids Techniques of identification and quantification of stilbenoids Levels of stilbenoids found in plants or food-based plants Effects of food processing on stilbenoids Trends and concluding remarks 3.5.1Phytochemistry of stilbenoidsThe hydroxylated derivatives of stilbenes are called stilbenoids and there are two general i References Further reading Phytochemistry of the tannins Biological activities of tannins Current and potential industrial applications of tannins Possible interactions of tannins Tannins techniques of extraction, purification, and fractionation Tannins techniques of identification and quantification Levels founds of tannins in plants/food-based plants Effects of food processing on tannins Trends and concluding remarks 3.6.1Phytochemistry of the tanninsTannins dominate quantitatively the vast plant secondary metabolites, being the fourth most References Phytochemistry of the curcuminoids Biological activities of curcuminoids Current and potential industrial applications of curcuminoids Possible interactions of curcuminoids Techniques of extraction, purification, and fractionation of curcuminoids Techniques for identification and quantification of curcuminoids Levels of curcuminoids founds in plants/food-based plants Effects of food processing on curcuminoids Trends and concluding remarks 3.7.1Phytochemistry of the curcuminoidsThe turmeric (Curcuma longa), an annually growing herb under the ginger family, is mos References Phytochemistry of the coumarin Classification of coumarin Biological activities of coumarin Current and potential industrial applications of coumarin Possible interactions of coumarin Techniques of extraction, purification, and fractionation of coumarin Techniques of identification and quantification of coumarin The titrimetric method Calorimetric methods Spectrophotometry Paper chromatography Thin-layer chromatography (TLC) Gas chromatographic method High-performance liquid chromatography (HPLC) Levels founds of coumarin in plants/food-based plants Effects of food processing on coumarin Trends and concluding remarks 3.8.1Phytochemistry of the coumarinCoumarin (1,2-benzopyrone; or chromen-2-one) belongs to a class of compounds present abu References Further reading Phytochemistry and classification of the phloroglucinols, xanthones, and anthrones Phloroglucinols Xanthones Anthrones Biological activities of phloroglucinols, xanthones, and anthrones Phloroglucinols Xanthones Anthrones Extraction and purification techniques of phloroglucinols, xanthones, and anthrones Phloroglucinols Xanthones Anthrones Identification and quantification techniques of phloroglucinols, xanthones, and anthrones Phloroglucinols Xanthones Anthrones Levels founds of phloroglucinols, xanthones, and anthrones in foods/plants Phloroglucinols Xanthones Effects of food processing on phloroglucinols, xanthones, and anthrones Phloroglucinols Xanthones Anthrones Pharmaceutical applications of phloroglucinols, xanthones, and anthrones Phloroglucinols Xanthones Anthrones Trends and concluding remarks Acknowledgment 3.9.1Phytochemistry and classification of the phloroglucinols, xanthones, and anthrones3.9.1.1PhloroglucinolsPhloroglucinol de References Further reading Analysis of aromatic acids (phenolic acids and hydroxycinnamic acids) Introduction Phenolic acids and human health Conjugation reactions for metabolite formation Structure of phenolic acids Hydroxycinnamates Hydroxybenzoic acids Biosynthesis of phenolic acids Extraction methods of phenolic acids Methods for identification of phenolic acids Novel methods in identification of phenolic acid Conclusion In memoriam References Further reading Analysis of phenylethanoids and their glycosidic derivatives Introduction Phenylpropanoid biosynthesis Phytochemistry and classification of the group Chemotaxonomy Separation, identification, and characterization techniques of phenylpropanoids Using spectroscopic data in organic structure analysis High performance liquid chromatography/mass spectrometry (HPLC/MS), HPLC-QTOF MS, and HPLC IT-TOF-MS assay of phen ... High performance liquid chromatography-mass spectrometry/mass spectrometry (HPLC-MS/MS) assay of phenylpropanoids Ultra high performance liquid chromatography-tandem mass spectroscopy (UHPLC-ESI-MS/MS) analysis of phenylpropanoids High performance liquid chromatography-photodiode array detector-atmospheric pressure chemical ionization/mass spe ... Capillary electrophoresis method (CE) Biological activities of phenylethanoids Antioxidant and free radical scavenging activities Neuroprotective activities Cytotoxic and antiproliferative effects Hepatoprotective and analgesic effects Antiviral, antibacterial, and antiprotozoal properties Antiinflammatory activities Effects on the cardiovascular system Phenylpropanoid occurrence in foods Effects of food processing on phenylpropanoids Thermal processes Nonthermal processes Mechanical processes Domestic processes Packaging processes Conclusions References Analysis of other phenolics (capsaicin, gingerol, and alkylresorcinols) Introduction Capsaicin Phytochemistry capsaicin Biological activity of capsaicin Potential industrial applications and possible interactions of capsaicin Techniques for extraction, purification, and fractionation of capsaicin Techniques of identification and quantification Gingerol Phytochemistry and synthesis Biological activities Potential industrial applications and possible interactions of gingerol Techniques of extraction and purification and isolation Identification and quantification of gingerol Alkylresorcinols Phytochemistry Biological activities Techniques of extraction and purification Identification and quantification of alkylresorcinols Levels of alkylresorcinols in foods and their potential industrial application Trends and remarks 6.1IntroductionPolyphenols or the plant phenolics are the secondary naturally occurring metabolites that arise biogenetically References Further reading Analysis of monoterpenes and monoterpenoids Introduction Phytochemistry of representative monoterpenes and monoterpenoids Origins of monoterpenes and monoterpenoids Biological activities and possible interactions Current and potential industrial applications Techniques of extraction, purification, and fractionation Techniques of identification and quantification Levels founds in plants/food-based plants Trends and concluding remarks References Analysis of sesquiterpenes and sesquiterpenoids Introduction Structure and classification of sesquiterpenes and sesquiterpenoids Biosynthesis of sesquiterpenes and sesquiterpenoids Extraction methods of sesquiterpenes and sesquiterpenoids Traditional extraction methods Advances in extraction methods Ultrasonic-assisted extraction Pressurized liquid extraction Subcritical water extraction Supercritical fluid extraction Microwave-assisted extraction Headspace extraction Analysis of sesquiterpenes and sesquiterpenoids Analytical methods (lactone-free) Analytical techniques of SLs Analysis of sesquiterpenes and sesquiterpenoids Conclusion References Further reading Analysis of diterpenes and diterpenoids Introduction Properties and classification of diterpenes Acyclic diterpenes Monocyclic diterpenes Bicyclic diterpenes Labdanes Halimanes and clerodanes Tricyclic diterpenoids Abietanes Pimaranes and cassanes Tetracyclic diterpenoids Macrocyclic diterpenoids and their cyclization products Miscellaneous diterpenoids Importance of chromatography in diterpenes analysis Effects of processing in the phytochemicals Conclusion References Further reading Sesterterpenoids Introduction Phytochemistry and classification of the group Linear sesterterpenoids Iono- and bi-carbocyclic sesterterpenoids Tricarbocyclic sesterterpenoids of the cheilanthane type Scalarane sesterterpenoids Ceriferene sesterterpenoids Ophiobolane sesterterpenoids Miscellaneous sesterterpenoids Gascardic acid Retigeranic acid Stellatic acid Main representatives of the group Ethnopharmacology Anticancer activity Antimicrobial activity Antibacterial activity Antifungal activity Phospholipases A2 (PLA2s) inhibition activity Miscellaneous activities Techniques of extraction and purification Extraction Maceration as a prevalent method Soxhlet method Ultrasonic-assisted extraction (UAE) Purification Crude fractionation Chromatographic methods Techniques for identification and quantification Identification Spectroscopic methods Methods used in computational chemistry Quantification Levels found in foods/plants Effects of food processing in the phytochemicals Biochemical changes Enzymatic reactions Main conclusions References Analysis of triterpenes and triterpenoids Introduction Steroids Phytochemistry and classification of the steroids Main representatives of the group Ethnophytopharmacology Techniques of extraction and purification Techniques of identification and quantification of steroids Levels found in foods/plants Pharmaceutical applications Saponins Phytochemistry and classification of the saponins Main representatives of the group Ethnophytopharmacology Techniques of extraction and purification of saponins Techniques of identification and quantification Levels found in foods/plants Pharmaceutical applications Phytoecdysteroids Phytochemistry and classification of the phytoecdysteroids Main representatives of the group Ethnophytopharmacology Techniques of extraction and purification Techniques of identification and quantification Levels found in foods/plants Pharmaceutical applications Conclusion References Analysis of tetraterpenes and tetraterpenoids (carotenoids) Introduction Phytochemistry, classification, and biosynthesis Representatives carotenoids Ethnophytopharmacology Techniques of extraction and purification Techniques of identification and quantification Levels in foods and effects of food processing on carotenoids content Pharmaceutical applications Main conclusions References Analysis of pentaterpenoids Introduction Main representatives of the group Ethnopharmacology Techniques of extraction and purification Shaking extraction Ultrasonic extraction Heat reflux extraction Supercritical fluid extraction Soxhlet extraction Pressurized liquid extraction Microwave-assisted extraction Techniques of identification and quantification Gas chromatography (GC) Supercritical fluid chromatography (SFC) Thin-layer chromatography (TLC) Capillary electrophoresis (CE) Nuclear magnetic resonance (NMR) spectroscopy X-ray spectroscopy High performance liquid chromatography (HPLC) Diode-array detector (DAD) Ultraviolet detection (UV) Fluorescence detection (FLD) Mass spectrometry (MS) Levels found in food/plants Effects of food processing in the phytochemicals Pharmaceutical applications Cancer HIV Inflammation Conclusion References Further reading Analysis of meroterpenoids Introduction Chemistry and classification of meroterpenoids Meroterpenoid pharmacology Meroterpenoids: From complex natural matrices to pure compounds Conclusions References Index A B C D E F G H I J K L M N O P Q R S T U V W X Y Z Analysis of amines Introduction and scope Structure and properties of representative biogenic amines Biological activities and toxicological effects of biogenic amines Possible interactions among different biogenic amines Current and potential industrial applications of biogenic amines Techniques of extraction, purification, and fractionation Techniques of identification and quantification Concentration levels of biogenic amines found in plants/food-based plants Effect of food processing in phytochemistry of biogenic amines Trends and concluding remarks References Analysis of betalains (betacyanins and betaxanthins) Introduction Phytochemistry and classification of the group Occurrence Biosynthesis of betalains Main representatives of the group Betacyanins: Red-violet pigments Betaxanthins: Yellow-orange pigments Biological and medicinal properties of betalains Antiradical and antioxidant activity Anti-inflammatory and chemopreventive properties Antilipidemic effects Anticancer properties Antimicrobial activity Techniques of extraction and purification Techniques of identification and quantification Accumulation and levels of betalains in Caryophyllales plants Factors affecting stability of betalains Pharmaceutical potential and applications Main conclusions References Analysis of carbohydrates (monosaccharides, polysaccharides) Phytochemistry (structure and properties) of carbohydrates Biological activities of carbohydrates Current and potential industrial applications of carbohydrates Possible interactions of carbohydrates with drugs/foods Techniques of extraction, purification, and fractionation of carbohydrates Techniques for the identification and quantification of carbohydrates Amounts of carbohydrates in plants/food-based plants Effects of food processing on the phytochemicals Trends and concluding remarks 18.1Phytochemistry (structure and properties) of carbohydratesCarbohydrates are an important class of naturally occurring macr References Analysis of chlorophylls Introduction Phytochemistry Classification of chlorophyll molecule Chlorophylls Bacteriochlorophylls The Chlorobium chlorophylls Main representatives of the group Ethnophytopharmacology Techniques of extraction and purification Extraction of chlorophyll molecule Chlorophyll extraction using organic solvents Arnon method for extraction of chlorophyll Microwave-assisted extraction of chlorophyll molecule Enzyme-mediated extraction of chlorophyll molecule Purification of chlorophyll molecule Techniques of identification and quantification UV/Vis spectroscopy HPLC Nuclear magnetic resonance spectroscopy (NMR) Levels founds in foods/plants Pharmaceutical applications Conclusion Acknowledgments References Further reading Analysis of glucosinolates Introduction Chemistry Natural abundance Use of glucosinolates in food and medicine Techniques of extraction and purification Pretreatment Extraction Isolation and purification Detection, quantification, and analysis by using hyphenated techniques Main conclusions References Analysis of gums and mucilages Introduction Classification of gums and mucilages Chemical and physical characteristics of gums and mucilages Techniques of extraction and purification Techniques of identification of gums Techniques of identification of mucilages Influences of manufacture processing on product quality and commercialization Purity versus impurity profile Pharmacological and industrial applications Toxicity Main conclusions References Further reading Analysis of plants lipids Phytochemistry of the plants lipids Biological activities of plants lipids Current and potential industrial applications of plants lipids Possible interactions of plants lipids Techniques of extraction, purification, and fractionation of plants lipids Techniques of identification and quantification of plants lipids Levels founds of plants lipids in plants/food-based plants Effects of food processing on plants lipids Pharmaceutical applications of plants lipids Trends and concluding remarks 22.1Phytochemistry of the plants lipidsLipids have vital role in biology either from plant or animal origin; they are a rich e References Analysis of polyacetylenes Introduction Phytochemistry and classification of the group Biosynthesis of PA in plants Distribution and classification Main representatives of PA Ethnophytopharmacoloy and pharmaceutical applications of PA Antimicrobial activity Neurotoxic, neuritogenic, and serotonergic effect Antiinflammatory effects Cytotoxicity and anticancer effects Allergenic properties Analysis and isolation of PA UV spectroscopy Raman mapping HPLC and LC-MS analysis Effect of food processing on PA Conclusions References Further reading Analysis of proteins, peptides, and amino acids Phytochemistry and classification of the proteins, peptides, and amino acids Biological activities of protein, peptides, and amino acids Current and potential industrial applicationsof protein, peptides, and amino acids Possible interactions of proteins, peptides, and amino acids with other drugs/food/supplements Protein, peptides, and amino acids techniques of extraction, purification, and fractionation Protein, peptides, and amino acids techniques of identification and quantification Levels of proteins, peptides, and amino acids in plants/food-based plants Effects of food processing on proteins, peptides, and amino acids Trends and concluding remarks 24.1Phytochemistry and classification of the proteins, peptides, and amino acidsProteins are one of the crucial macromolecules References Further reading Analysis of quinonoids Phytochemistry of the quinonoids Biological activities of quinonoids Current and potential industrial application of quinonoids Possible interactions of quinonoids Techniques of extraction, purification, and fractionation of quinonoids Techniques of identification and quantification of quinonoids Levels of quinonoids found in plants/food-based plants Effects of food processing on quinonoids Trends and concluding remarks 25.1Phytochemistry of the quinonoidsQuinones represent one of the most important groups of organic molecules set in chemistry References Analysis of organic acids Introduction Phytochemistry Structure Physical properties Acidity Classification Monocarboxylic acid Dicarboxylic acid Alpha-hydroxyl acids Sugar acids Plant organic acids Main representatives of the group Monocarboxylic acids Acetic acid Formic acid Propionic acid Sorbic acid Benzoic acid Dicarboxylic acids Ascorbic acid Fumaric acid Succinic acid Alpha-hydroxyl acids Lactic acid Citric acid Malic acid Sugar acids Gluconic acid Tartaric acid Ethnophytopharmacology Techniques of extraction and purification Extraction techniques Solid-liquid extraction Ultrasound-assisted extraction Microwave-assisted extraction Accelerated liquid extraction Supercritical fluid extraction Enzyme-assisted extraction Purification techniques Membrane separation Preparative high-performance liquid chromatography Counter-current chromatography Thin layer chromatography (TLC) Techniques of identification and quantification Gas chromatography (GC) Ion chromatography Capillary electrophoresis (CE) High-performance liquid chromatography (HPLC) Nuclear magnetic resonance (NMR) spectroscopy Liquid chromatography-mass spectrometry (LC-MS) Levels found in foods/plants Plants and vegetables Fruits Juices Vinegar and wine Honey Coffee Dairy products Effects of food processing in the phytochemicals Temperature (heating or boiling) Blanching Cold storage Pasteurization Milling Baking Fermentation References Future perspectives in natural products analysis Introduction Identification and quantification of natural products Concluding remarks References Index A B C D E F G H I J K L M N O P Q R S T U V W X Y Z