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Nomenclature and biosynthesis of sterols and related compounds

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Analysis of Sterols

Abstract

The first known sterol, cholesterol, derived its name because it is a major constituent of human gallstones, hence it was named cholesterine from the Greek chole = bile and stereos = solid [1]. The developments in knowledge on the structure, chemistry and biochemistry of sterols have been comprehensively documented in a number of excellent books to which the reader is referred for information [2–10]. A precise definition of what constitutes a sterol is rather difficult [9, 11] and has undoubtedly become more confusing as the structures of and biosynthetic relationships between sterols and the related cyclic triterpene alcohols (or triterpenoids) and steroids have been unravelled. The terms triterpenoid, sterol and steroid are well established in the literature and they are widely used to describe and categorize natural products. When these names evolved several decades ago they were adequate to allow the assignment of a compound to a particular structural type. However, the distinctions between these three types of natural product have blurred with the multitude of structures now elucidated, and the revelation that certain triterpenoids are the biosynthetic precursors to sterols, which in turn are modified to yield steroids. This chapter describes the nomenclature system recommended by the International Union of Pure and Applied Chemistry (IUPAC) and the International Union of Biochemistry (IUB) for the naming of sterols and related compounds and which we have elected to use. This chapter also briefly covers some aspects of sterol and triterpene biosynthesis in order that the origins and relationships of the many known sterols can be better understood; this information can sometimes be useful in sterol identification and structure elucidation studies.

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Authors and Affiliations

  1. School of Biological Sciences, University of Liverpool, UK

    L. John Goad

  2. College of Science and Technology, Nihon University, Tokyo, Japan

    Toshihiro Akihisa

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Goad, L.J., Akihisa, T. (1997). Nomenclature and biosynthesis of sterols and related compounds. In: Analysis of Sterols. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-1447-6_1

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  • DOI: https://doi.org/10.1007/978-94-009-1447-6_1

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