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1990 | Buch

Diterpenes of Flowering Plants

Compositae (Asteraceae)

verfasst von: Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry

Verlag: Springer New York

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More than 1200 diterpenes have been identified from approximately 550 Compo sitae taxa (Figure 1 [pp. 219-384], Tables 1-3 [pp. 7-218]). The annual output of such reports rose sharply during the past several years, a trend that was also reflected by other major lipophilic constituents of the Compositae: acetylenes (63, 465), sesquiterpene lactones (266, 458), and benzofurans and chromenes (429). Unlike these other natural products, no review of the diterpene chemistry of the Compositae has been published. Given the bulk of data currently on hand, a review of this topic is clearly overdue. Several major goals influenced the preparation of this review. The first was to provide a useful reference to guide terpenoid chemists to the literature of known compounds. The published reports for 1200 structures provide a sizable body of spectroscopic data applicable to the investigation of new compounds. The study of diterpenes has been hampered by the absence of an all-inclusive nomenclature and classification system for the various skeletal types. Conse­ quently, a second goal was to organize structural data into a classification scheme designed to group compounds by biogenetic homology, and to standardize such features as diterpene nomenclature and numbering. Pursuant to this goal, the published names (Table 1) and numbering systems (Table 2) for all compounds are included.

Inhaltsverzeichnis

Frontmatter
Chapter 1. Introduction
Abstract
More than 1200 diterpenes have been identified from approximately 550 Compositae taxa (Figure 1 [pp. 219–384], Tables 1–3 [pp. 7–218]). The annual output of such reports rose sharply during the past several years, a trend that was also reflected by other major lipophilic constituents of the Compositae: acetylenes (63, 465), sesquiterpene lactones (266, 458), and benzofurans and chromenes (429). Unlike these other natural products, no review of the diterpene chemistry of the Compositae has been published. Given the bulk of data currently on hand, a review of this topic is clearly overdue.
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Chapter 2. Compound Names, Structures, and Sources
Abstract
The names (Table 1 [pp. 7–59]) and structures (Figure 1 [pp. 219–384]) of diterpenes reported from the Compositae are organized according to skeletal type following the sequence indicated in Figure 2 (p. 392). If a name was assigned to a structure at the time the compound was reported, that name was included in Table 1. Otherwise, the structure was given a name compatible with the names previously assigned to related compounds. If more than one name was applied in the literature to the same structure, usually the first-published name was included in Table 1, followed by additional names listed within brackets. The compound number listed with each name was used throughout this treatment when reference to the compound was made. Comments about a reported compound were also included in brackets on a line below the compound name. Usually these comments describe situations in which the name applied to the compound was incompatible with either the illustrated structure or the published spectroscopic data.
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Chapter 3. Biogenesis
Abstract
Cyclization of the linear diterpene precursor usally proceeds along two alternative parallel routes (Figure 2 [p. 392]), one leading to the bicyclic “normal” labdane ( normal-labdane) absolute stereochemistry and the other resulting in its antipodal, enantiomeric (ent-labdane) absolute stereochemistry. As a consequence of these two parallel biosynthetic routes, diterpenes lack the homogeneous absolute stereochemistry of the triterpenes.
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Chapter 4. Diterpene Distribution: Compositae
Abstract
Green plants possess (1) geranylgeraniol, the required precursor for both carotenoid and gibberellin biosynthesis, (2) the enzymatic machinery to cyclize geranylgeraniol (or its isomer) to ent-kaurene, and (3) the enzymes for the oxidation of ent-kaurene and other diterpene substrates (420). Normally, the steady-state concentration of the products of these pathways falls below the level of detectability of all but the most sensitive analytical instruments. By comparison, the compounds that are the focus of this review constitute an “abnormal” biosynthetic excess detectable in the form of resins. Often, general plant metabolism is isolated from these biologically active resins by the comparmentation of resin biosynthesis and storage within glandular trichomes.
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Chapter 5. Biological Activity of Diterpenes
Abstract
Various biological activities (Table 13 [pp. 489–490]) have been reported for plant diterpenes, principally from members of the Ericaceae, Euphorbiaceae, Lamiaceae, and Compositae. Each of the major diterpenoid classes from this last family will be discussed below in terms of its biological properties.
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Chapter 6. Diterpene Analysis with Emphasis on Clerodanes
Abstract
Early work on Compositae diterpenes focused on Solidago and the normal-labdane, solidagenone (Figure 33 [pp. 513–514]; Structure 158) (9, 16, 17). Later, ent-clerodanes (kolavanes) were found to co-occur with the labdanes (364, 365). The first identified novel clerodane, solidagonic acid (Figure 33; Structure 500), was shown by chemical interconversion (364, 365; Figure 33) to share the orientivity of the major chiral centers, C-5, C-8, C-9, and C10, with the co-occurring clerodanes of known stereochemistry, kolavenic acid (495) and kolavenol (Figure 33; Structure 475).
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Chapter 7. References
Fred Seaman, Ferdinand Bohlmann, Christa Zdero, Tom J. Mabry
Backmatter
Metadaten
Titel
Diterpenes of Flowering Plants
verfasst von
Fred Seaman
Ferdinand Bohlmann
Christa Zdero
Tom J. Mabry
Copyright-Jahr
1990
Verlag
Springer New York
Electronic ISBN
978-1-4612-3274-2
Print ISBN
978-1-4612-7945-7
DOI
https://doi.org/10.1007/978-1-4612-3274-2