| 书目名称 | The Flavonoids | | 编辑 | J. B. Harborne (Reader in Phytochemistry),T. J. Ma | | 视频video | http://file.papertrans.cn/910/909798/909798.mp4 | | 图书封面 |  | | 描述 | The flavonoids, one of the most numerous and widespread groups of natural constituents, are important to man not only because they contribute to plant colour but also because many members (e.g. coumestrol, phloridzin, rotenone) are physiologically active. Nearly two thousand substances have been described and as a group they are universally distributed among vascular plants. Although the anthocyanins have an undisputed function as plant pigments, the raison d‘etre for the more widely distributed colourless flavones and flavonols still remains a mystery. It is perhaps the challenge of discovering these yet undisc10sed functions which has caused the considerable resurgence of interest in flavonoids during the last decade. This book attempts to summarize progress that has been made in the study of these constituents since the first comprehensive monograph on the chemistry of the flavonoid compounds was published, under the editorship of T. A. Geissman, in 1962. The present volume is divided into three parts. The first section (Chapters 1-4) deals with advances in chemistry, the main emphasis being on spectral techniques to take into account the re cent successful applications of NMR a | | 出版日期 | Book 1975 | | 关键词 | chemistry; development; evolution; metabolism; physiology; plant; plants; spectroscopy; synthesis; systematic | | 版次 | 1 | | doi | https://doi.org/10.1007/978-1-4899-2909-9 | | isbn_softcover | 978-0-12-324602-8 | | isbn_ebook | 978-1-4899-2909-9 | | copyright | Springer Science+Business Media Dordrecht 1975 |
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Front Matter |
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Abstract
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,Isolation Techniques for Flavonoids, |
Ken. R. Markham |
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Abstract
Over the past decade, the techniques used for the isolation of flavonoids from plant material have not changed drastically Review articles on this general topic by Seshadri (1962) and Seikel (1962) emphasized the importance of solvent extraction, crystalliz ation, and column and paper chromatography, and these techniques are still very much in use today. Thin-layer chromatography, sephadex gel chromatography and gas-liquid chromatography are perhaps the three major innovations since that time. The increasing use of these essentially small scale methods (together with paper chromatography) has been brought about largely by two factors: (1) the need to isolate only small amounts of material for structure analysis and (1i) the availability of only limited quantities of plant materials for phyto chemical surveys.
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,Ultraviolet-Visible and Proton Magnetic Resonance Spectroscopy of Flavonoids, |
Ken. R. Markham,Tom. J. Mabry |
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Abstract
A number of reviews of ultraviolet and visible absorption spectroscopy have appeared in the past (Jurd, 1962; Mabry ., 1970; Swain, 1965; Mabry, 1969; Harborne, 1963) the most comprehensive being those of Jurd (1962) and Mabry ., (1970). The article by Jurd summarizes the work in this field up to about 1960 and gives detailed references to the original spectroscopic work carried out with flavonoids. The book by Mabry . (1970) updates Jurd’s chapter and in addition provides a detailed catalogue of the ultraviolet (UV) spectra of 175 flavonoids together with comprehensive data on reagent induced shifts for each flavonoid. The present article includes some of the more significant aspects of the earlier reviews and in addition brings them up to date.
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,Mass Spectrometry of Flavonoids, |
Tom J. Mabry,Ken R. Markham |
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Abstract
Electron impact mass spectrometry of both flavonoid aglycones and glycosides serves as a valuable aid in determining their structures, especially when only very small quantities (1.e. less than 1 mg) of the compounds are available. It has been applied successfully to all classes of flavonoid aglycones (Porter and Baldas, 1971) and more recently to a number of different types of glycosides including mono- and di-.-glycosylflavones and mono- to tetra-.-glycosides. In contrast, chemical ionization (CI), using methane as the reactant gas, has only been applied to a few aglycones and gives few diagnostic fragments except for flavanones and dihydroflavonols (Kingston and Fales, 1973); therefore, this account will be largely restricted to electron impact mass spectrometry of flavonoids.
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,Synthesis of Flavonoids, |
Hildebert Wagner,Loránd Farkas |
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Abstract
Theoretically, there are at least four ways of forming the C. C. —C. flavonoid skeleton from simple starting materials, but only two have achieved importance for the laboratory synthesis (Geissman, 1962, p. 409): (1) Condensation of a C.C. unit (2-hydroxyacetophenone) with a C.C! unit (aromatic aldehyde) according to scheme A; and (1i) Acylation of phenols (C. unit) with a cinnamic acid derivative or its equivalent (C.C. unit) according to scheme B (Geissman, 1962, p. 409), which also corresponds to the biosynthetic pathway (Fig. 4.1). In addition, many flavonoids can be prepared by modifying existing C. structures by oxidation, reduction, isomerization, partial .- and .-alkylation, dealkylation, selective glycosylation or partial hydrolysis.
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,The Anthocyanins, |
C. F. Timberlake,P. Bridle |
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Abstract
The anthocyanins are the water-soluble pigments which are largely responsible for the attractive colours of flowers, leaves, fruits, fruit juices and wines. Apart from their biological role, they are important aesthetically and economically, since their stability is of significance in the marketability of plant products. The most significant recent advances in anthocyanin chemistry have perhaps been stimulated by the increasing realization that in wine and related products, anthocyanins occur not only as monomers but as part of much larger complexes, in loose association with or chemically bonded to other components. This has led to a desire to characterize anthocyanins as they actually exist in plant material using methods of extraction and examination designed to cause least interference or alteration in structure. At the same time, the structures and properties of the monomers have been studied and their occurrence in extracts of plant material has been further documented.
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,Flavones, |
K. Venkataraman |
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Abstract
The number of naturally occurring flavones known at present is 128, excluding flavonols and glycosides of both flavones and flavonols which are treated in Chapters 7 and 8. The parent unsubstituted flavone, produced apparently by an aberrant biosynthetic pathway, occurs in the farina on species of . and the closely related . (Harborne, 1971). 2’-Hydroxyflavone and 5, 2′-dihydroxy-flavone have very recently been detected in the secretion of the glandular cells of . flowers (Bouillant ., 1971a). The 95 flavones in the following six tables (Tables 6.1–6.6) are derived from 32 hydroxyflavones, only eighteen of which have been isolated so far; the remaining fourteen occur as partially or fully O-methylated products. Thus no hexa- or heptahydroxyflavone has yet been isolated, although nine ethers of 5, 7, 8, 2′, 3′, 4′- and 5, 6, 7, 8, 3′, 4′-hexahydroxyflavone and four ethers of 5, 6, 7, 8, 3′, 4′, 5′-heptahydroxyflavone are known. Linderoflavones A and B are the only two flavones containing a methylenedioxy group. The letters A and G in the second column of Tables 6.1–6.6 signify occurrence as the aglycone and as a glycoside respectively.
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,Flavonols, |
Otto Richard Gottlieb |
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Abstract
Since flavonols (l, R = OH) are simply flavones (1,R = H) in which the 3-position is substituted by a hydroxyl, both classes of pigment have so far been considered together (Venkataraman, 1959; Gripenberg in Geissman, 1962, p. 406; Dean, 1963, p. 280). This practice is justified in that much of their chemistry—analysis, synthesis, reactions—has a common theoretical basis. However, today it is apparent that this simple difference in structure is of considerable biosynthetic, physiological, phylogenetic, chemosystematic, pharmacological and analytical significance.
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,Flavone and Flavonol Glycosides, |
Jeffrey B. Harborne,Christine A. Williams |
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Abstract
A vast range of different flavone and flavonol glycosides have now been reported in plants. For quercetin, the most common flavonol aglycone, over seventy glycosidic combinations have been fully characterized and many more have been partly analysed. Quercetin must thus be unique among all the many known natural plant constituents in occurring in quite so many different combined forms. Almost as many glycosides have been described in the case of the other two common flavonols, kaempferol and myricetin, and there are also numerous derivatives of the two common flavones, apigenin and luteolin. Adding in the known glycosides of the rarer flavonols and flavones brings the total to nearly 400.
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,Chalcones, Aurones and Dihydrochalcones, |
Bruce A. Bohm |
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Abstract
This chapter will treat three small groups of flavonoids: chalcones, dihydrochalcones and aurones. In the case of chalcones and aurones, placing them together in the same chapter reflects their traditional treatment as ‘anthochlor’ pigments. This term was originally coined to identify a group of yellow pigments which turned red in the presence of alkali. It was not until many years later that anthochlor pigments were found to consist of two discrete chemical types. Although a review devoted to the aurone glycosides alone recently appeared (Farkas and Pallos, 1967), the discussion of the two types together seems justifiable in view of the common occurrence in nature of chalcone-aurone pairs. Despite their close biochemical relationships, the rapidly expanding chalcone literature may make a separation necessary again in the future.
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,Natural Proanthocyanidins, |
E. Haslam |
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Abstract
The formation of red colours from colourless materials present in the leaves, fruit and flowers of many higher plants has long been known and not surprisingly some uncertainty exists as to who first demonstrated this distinctive property. The chemical and bio- chemical literature show that Staats (1895), Laborde (1908), Tswett (1914) and Willstätter and Nolan (1915) all reported experimental observations of this type during the same period at the beginning of this century but Pigman and his associates (1953) credit Robert Boyle with the first recorded example of this property some sixty years earlier.
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,Flavanones and Dihydroflavonols, |
Bruce A. Bohm |
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Abstract
This chapter is concerned with the closely related flavanones and dihydroflavonols. Flavanones are based upon structure (1), 2-phenylbenzopyran-4-one, which is flavanone itself. The parent compound is not known to be naturally occurring; the simplest plant flavanone has a hydroxy 1 group at position 7. The numbering system of the flavanone nucleus is similar to that in most other flavonoid series. Flavanones are isomeric with chalcones from which they can be obtained synthetically and from which they arise biosynthetically. Flavanones have a centre of asymmetry at C-2 so that naturally occurring members are often optically active. The absolute configuration of a number of these compounds has also been established. It is of historical interest that the isolation of optically active flavanones provided a strong argument that these compounds were natural and not simply artifacts resulting from overzealous treatment of natural chalcones.
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, ,-Glycosylflavonoids, |
J. Chopin,M. L. Bouillant |
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Abstract
The rapid expansion of chromatographic analysis applied to plant extracts has disclosed the frequent occurrence of compounds which present the solubility and chromatographic properties of flavonoid glycosides, but which cannot be hydrolyzed even after prolonged treatment with acid, partial isomerization often taking place underthese conditions. This resistance towards acid hydrolysis, the most distinctive feature of these compounds, results from the sugar being directly attached to the flavonoid nucleus by a carbon-carbon bond, and accounts for the difficulties encountered in the identification of the glycosyl residue. Furthermore, the anomalous results given by periodate oxidation led to conflicting assumptions about the structure of the side chain and the nature of the acid isomerization.
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,Biflavonoids, |
Hans Geiger,Christopher Quinn |
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Abstract
Harborne (1967) could still define biflavonyls as ‘dimers’ of apigenin and as such they were well distinguished from other flavonoid ‘dimers’ like the proanthocyanidins, theaflavins and dracorubin. During the past six years, however, a wealth of biflavonoids has been discovered, which differ from the ‘classical biflavones’ (amento-, hinoki, cupressu- and agathis-flavone) not only in the hydroxylation pattern of the aromatic rings, but also in the oxidation level of the central heterocycle (see Locksley, 1973).
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,The Isoflavonoids, |
E. Wong |
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Abstract
Isoflavonoids differ from other flavonoid compounds in having as a basic structural feature the branched C.C.C. skeleton shown in (1). Within this group are included many classes of natural products. Isoflavones, isoflavanones, rotenoids, pterocarpans and coumestans are well established members of this group (Ollis, 1962), while others such as isoflavans, 3-aryl-4-hydroxycoumarins, coumaronochromones, and hydroxy- and dehydro-variants of pterocarpans and rotenoids have only recently been reported as natural products. The skeletal structures of the various classes of isoflavonoid, arranged in order of their oxidation level, are given in Fig. 14.1. The structural variety displayed in the isoflavonoids is, in fact, greater than existing in the normal flavonoid series.
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,Neoflavanoids, |
Dervilla M. X. Donnelly |
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Abstract
The term neoflavanoid, suggested by Dr T. Swain, was first used by Ollis in the 1965a Eyton publication to describe the group of natural products with a 4-arylchroman skeleton (1). These Q . compounds relate closely to the flavanoids (2) and the isoflavanoids (3). The open-chain compounds, the dalbergiones (4) (Gonçalves da Lima and Dalia Maia, 1961) and the 3, 3-diarylpropenes (5) have been included in the neoflavanoid class, in line with the assignment of 2’-hydroxychalcone (6) and of angolensin (7) to the flavanoid and isoflavanoid classes respectively.
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,Biosynthesis of Flavonoids, |
Klaus Hahlbrock,Hans Grisebach |
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Abstract
Interest in the biosynthesis of flavonoids was first stimulated by studies on genetic aspects of flower colour (cf. Harborne, 1967; Hess, 1968) and by chemical speculations on the mode of formation of the carbon skeleton of this class of compounds (Birch and Donovan, 1953; Robinson, 1955); tracer studies were first applied to the problem around 1957. Investigations with intact plants or plant tissues led to a basic knowledge of the precursors required and to an understanding of some details of the biosynthesis of flavonoids. From this, a general picture of the interrelationships between various classes of these compounds has emerged. In the course of these tracer experiments, however, it became apparent that a more detailed knowledge of the nature and sequence of the individual biosynthetic steps and their regulation could only be gained by investigations of the enzymes involved.
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,Metabolism of Flavonoids, |
Wolfgang Barz,Wolfgang Hösel |
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Abstract
This chapter will deal with various aspects of flavonoid turnover and degradation in higher plants and microorganisms. The microbial dissimilation of flavonoids has been a well understood area of biochemical research for many decades. It has been part of the more general field of microbial transformations of natural aromatic compounds, where it has been shown that all organic molecules are degraded by some form of life to maintain the carbon cycle of nature. Soil and sewage microflora are specifically adapted to perform this task. The results of microbial metabolism will be discussed here to outline the chemical principles governing flavonoid dissimilation and to relate them to the fate of flavonoids in higher plants.
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,Physiology and Functions of Flavonoids, |
Jerry W. McClure |
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Abstract
This chapter is concerned with physiological factors that control levels of flavonoids accumulating in plants and with the biological implications of these accumulations both within the plant and in plant-animal (1ncluding man) interactions. Levels of flavonoids within plants are a reflection of the efficiency of biosynthesis (see Chapter 16) tempered by turnover and degradation (Chapter 17) during growth and development. These are all influenced by the external environment. The functions of flavonoids may be approached by a consideration of their general reactivity when introduced into biochemical systems, the many implications of their pigment characteristics, their possible mediation in plant growth and development, and their effects on animals and microorganisms.
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,The Biochemical Systematics of Flavonoids, |
J. B. Harborne |
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Abstract
Modern plant biochemical systematics represents an interdisciplinary approach to the many problems of plant classification and can be dated from 1962, the year in which the first international conference on this topic was held. From the proceedings of this meeting, which were published in the following year (Swain, 1963), it is clear that flavonoids were already regarded as potentially important taxonomic markers since no less than a third of the 18 chapters which made up the volume dealt . with these constituents. In addition, one of the very first examples of a significant correlation between chemistry and taxonomy was the discovery of a relationship between sectional classification and flavonoid heartwood constituents in the genus . (Erdtman, 1963).
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