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Sesquiterpene Lactones: Biogenesis and Biomimetic Transformations

  • Chapter
Biochemistry of the Mevalonic Acid Pathway to Terpenoids

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 24))

Abstract

The different skeletal types of sesquiterpene lactones (SLs) are classified on the basis of their carbocyclic ring skeleton, in which the suffix “olide” is used to indicate the presence of a lactone group. The majority of SLs from higher plants contain α-methylene-γ-lactone functions (1) in which H-7 is, without exception, α-oriented.1–4 Certain liverworts, however, produce SLs of the enantiomeric series.5 In this review the biogenesis of only those common SLs will be considered in which one of the isopropyl methyls of the sesquiterpene ring is oxidized. The major skeletal types of SLs with the generally accepted numbering are outlined in Figure 1. The lactone rings are shown as 12,6-lactonized structures, although many SLs contain 12,8-lactones. The by far largest number of SLs has been isolated from the Asteraceae (Compositae),1–4 but they are also found in other angiosperm families including the Acanthaceae, Amaranthaceae, Apiaceae,6 Aristolochiaceae, Burseraceae, Bombacaceae, Coriariaceae, Illiciaceae, Magnoliaceae, Menispermaceae, Lamiaceae, Lauraceae, Polygonaceae and Winteraceae.

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Authors and Affiliations

  1. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803, USA

    Nikolaus H. Fischer

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  1. Nikolaus H. Fischer
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  1. University of British Columbia, Vancouver, British Columbia, Canada

    G. H. Neil Towers

  2. Reed College, Portland, Oregon, USA

    Helen A. Stafford

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© 1990 Plenum Press, New York

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Fischer, N.H. (1990). Sesquiterpene Lactones: Biogenesis and Biomimetic Transformations. In: Towers, G.H.N., Stafford, H.A. (eds) Biochemistry of the Mevalonic Acid Pathway to Terpenoids. Recent Advances in Phytochemistry, vol 24. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-8789-3_4

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  • DOI: https://doi.org/10.1007/978-1-4684-8789-3_4

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