Summary

Lipids are the naturally occurring materials isolated from plants and animals by extraction with a nonpolar organic solvent. Animal fats and vegetable oils are the most widely occurring lipids. Both are triacylglycerols—triesters of glycerol with long-chain fatty acids. Animal fats are usually saturated, whereas vegetable oils usually have unsaturated fatty acid residues.

Phospholipids are important constituents of cell membranes and are of two kinds. Glycerophospholipids, such as phosphatidylcholine and phosphatidylethanolamine, are closely related to fats in that they have a glycerol backbone esterified to two fatty acids (one saturated and one unsaturated) and to one phosphate ester. Sphingomyelins have the amino alcohol sphingosine for their backbone.

Eicosanoids and terpenoids are still other classes of lipids. Eicosanoids, of which prostaglandins are the most abundant kind, are derived biosynthetically from arachidonic acid, are found in all body tissues, and have a wide range of physiological activity.

Terpenoids are often isolated from the essential oils of plants, have an immense diversity of structure, and are produced biosynthetically from the five-carbon precursor isopentenyl diphosphate (IPP). Isopentenyl diphosphate is itself biosynthesized from 3 equivalents of acetate in the mevalonate pathway.

Steroids are plant and animal lipids with a characteristic tetracyclic carbon skeleton. Like the eicosanoids, steroids occur widely in body tissues and have a large variety of physiological activities. Steroids are closely related to terpenoids and arise biosynthetically from the triterpenoid lanosterol. Lanosterol, in turn, arises from cationic cyclization of the acyclic hydrocarbon squalene.