Analysis of Sterols
L. John Goad and Toshihiro Akihisa
Blackie Academic & Professional, London (1997)

1 Nomenclature and biosynthesis of sterols and related compounds
1.1 Introduction
1.2 IUPAC-IUB recommended nomenclature for steroids and toriterpenoids
1.3 The biosynthesis of sterols and triterpenes
2 Extraction of sterols from tissues
2.1 Introduction
2.2 Extraction methods
2.3 Separation of sterols from extracted lipids
2.4 Examples of the extaction of sterols
3 Initial separation methods
3.1 Introduction
3.2 Digitonin precipitation of sterols
3.3 Separation of freesterols and steryl conjugates from a total lipid by adsorption column chromatography
3.4 Thin-layer chromatography
3.5 The use of mini-columns for the preliminary separation of sterol fractions
3.6 Hydrolysis of steryl conjugates
3.7 Silver nitrate or argentation chromatography
3.8 Autoxidation and isomerization of sterols
4 High-performance liquid chromatography of sterols
4.1 Introduction
4.2 Normal-aand reversed-phase HPLC
4.3 HPLC detectors
4.4 HPLC of sterol derivatives
4.5 Influence of column temperature on sterol separation by HPLC
4.6 Retention date of sterols on HPLC
4.7 Sterol separation factors on HPLC
4.8 Differentiation of C-24 epimers of 24-alkylsterols on reverased-phase HPLC
5 Gas-liquid chromatography of sterols
5.1 Introduction
5.2 Packed columns and the stationary phase
5.3 Capillary columns
5.4 Sample injection and detection
5.5 Derivatization of sterols
5.6 Preparative GC
5.7 Retention time data
5.8 Separation facrors
5.9 GC of the C-24 epimers of 34-alkylsterols
5.10 GC of steryl conjugates
6 Infrared and ultraviolet spectroscopy of sterols
6.1 Introduction
6.2 Infrared spectroscopy
6.3 Ultraviolet spectroscopy
7 Mass spectrometry of sterols
7.1 Introduction
7.2 Sample ionization
7.3 Derivatives used for mass spectrometry of sterols
7.4 Mass-spectral fragmentations of the sterol rings
7.5 Mass spectra of tetracyclic and pentacyclic triterpene alcohols
7.7 Mass spectrometry of steryl conjugates
8 1H NMR spectroscopy of sterols
8.1 Introduction
8.2 Methyl signals
8.3 methine and olefinic protons
8.4 Quantitative estimation of C-24 epimeric 24-alkylsterol mixtures
8.5 Aromatic solvent induced shifts (ASIS)
8.6 Lanthanide-induced shifts (LIS)
9 13C NMR spectroscopy of sterols
9.1 Introduction
9.2 Methods for signal assignments
9.3 13C Chemical shift date of sterols and triterpene alcohols
10 One-dimensional and two-dimensional NMR spectroscopy of sterols
10.1 Introduction
10.2 1D NMR spectroscopy
10.3 2D NMR spectroscopy
10.4 Connectivity diagrams for use with 2D NMR date
10.5 Generalized 1D and 2D strategies for sterols and related compounds
10.6 Conplate assignments of 1H NMR spectra of sterols
11 X-ray crystallography of sterols
12 Sources of sterols
12.1 Introduction
12.2 4-Desmethylsterols
12.3 Large-scale purification of 4-desmethylsterols
12.4 Sterols with methyl groups at C-4 and/or C-14
12.5 Tetracyclic triterpene alcohols
12.6 Pentacyclic triterpene alcohols and ketones
12.7 The use of inhibitors of sterol biosynthesis to produce specific sterols
12.8 Sources of sterols and tetra- and pentacyclic triterpenes
Appendix 1 The trivial names of sterols
Appendix 2 Structures of pentacyclic triterpenes
Appendix 3 Physical date of selected sterols and triterpenes
Appendix 4 The quantification of sterols