Sterols represent a class of hydrophobic ringed lipid molecules that are commonly found in biological membranes throughout the eukarya. Sterols can constitute greater than 50% of the membrane lipid content present in the cells and are known to alter membrane fluidity and structure. Though the mechanisms of these effects are still under debate, sterols have been proved to induce altered lipid phases in bilayer systems, basically increasing the order of acyl chains along with maintaining lipid translational fluidity. Their actions are found to be vital for the formation of lipid rafts with various effects on cell biology and serve as precursors to steroid hormones in animals. The formula of sterol is C17H28O.
Sterol Structure
All naturally occurring sterols are made up of a hydrocarbon tetrameric fused ring structure and it also obtains a small degree of polarity from a 3-hydroxyl in the β configuration; α-hydroxyl sterols are not seen in natural membranes. The very common sterols also possess a short aliphatic tail on the opposite end on C17. In lipid bilayers, the hydroxyl functions as the polar head group and it is directed towards the phospholipid head groups of the bilayer, whereas the rings and short hydrophobic tail extend into the hydrophobic core of the membrane, aligning along the acyl chains of the phospholipids. The arrangement of sterols is such that the α side of the relatively rigid ring structure is flat whereas the β side has protruding methyl groups; this structure maintains their interactions with lipids and allows significant contact on the flat surface.
Common Sterols
Many different types of sterols are found in biological membranes and few among them are specific only to certain phyla. Small changes in their structure can change their effect on membrane structure and dynamics as discussed earlier. Cholesterol is the most common form of a sterol found in animal membranes and it accounts for about 20-30% of sterols found therein. It is characterized by a single double bond in ring B (C5-C6) and the lack of a branching carbon at position 24. Ergosterol another very common sterol is found in the membranes of fungi and protists and it mainly differs from cholesterol by having two more carbon-carbon double bonds (one in ring B, another between carbons 22 and 23 in the tail region) and a methyl group at position 24.
Sterols obtained from plants are referred to as phytosterols. Common phytosterols are as follows: campesterol, stigmasterol and sitosterol, however, hundreds of different compounds have been isolated from plants. Hopanoids are usually pentacyclic compounds that share a common structure with sterols and are generally found in prokaryotic membranes, where they are thought to affect membrane stability and structure similar to sterols.
Significance of Sterols
Sterols and their related compounds play significant roles in the physiology of eukaryotic organisms. For example, cholesterol forms a part of the cellular membrane in animals, where it affects the cell membrane’s fluidity and acts as a secondary messenger in developmental signalling. In humans and other animals, corticosteroids like those of cortisol act as signalling compounds in cellular communication and general metabolism. Sterols are common components of human skin oils.