Glycosylated Sterols

Glycosylated sterols are composed of sterols and sugar molecules. Glycosylated sterols have unique chemical structures that confer different biological activities and functions such as regulation of cell membrane stability, resistance, bioactivity and nutritional value, etc. Ensuring the safety of glycated steroids in humans is a comprehensive process that requires a combination of factors such as the nature of the compound, dosage, use and target population. Proper evaluation and control measures can reinforce the safety of glycated steroids and ensure their use under appropriate conditions. BOC Sciences offers a wide range of glycosylated sterols products such as 7β-Hydroxy Cholesterol, 25-hydroxycholesterol-3-sulfate, 25-Hydroxy-Cholesterol, and so on. Moreover, we can also customize glycosylated sterols products according to the needs of our customers.

Types of Glycosylated Sterols

Acylated steryl glycosides (ASGs) and steryl glycosides (SGs) are the main derivatives of sterols. ASG and SG can vary depending on the type of sterol backbone and sugars, the conformation of the bonds, the number of sugars, and the acylation of the sugars.

Fig. 1. Examples of the structural formulas of common ASG and SG (European Journal of Lipid Science and Technology. 2012, 114(6): 656-669).

Acylated Steryl Glycosides (ASGs)

ASGs are a special type of glycated sterols that are structurally similar to SGs, but they have additional fatty acid moieties. These fatty acid groups can be linked to sugar groups and sterol groups to form complex glycated sterol structures. ASGs are also common in plants and are thought to play an important role in maintaining cell membrane structure and function.

Steryl Glycosides (SGs)

SGs are made by combining one or more sugar molecules with sterols. SGs are widely distributed in plants, algae, and fungi, but are relatively rare in bacteria and animals. In the case of plants, they are generally found in plant tissues such as fruits, roots, stems, and leaves. The functions of SGs include disease, fungus, and pest resistance, as well as enhancing cell membrane stability and stress resistance.

Biosynthesis of Glycosylated Sterols

The intricate process of biosynthesizing glycosylated sterols encompasses a myriad of glycosyl modification reactions, such as methylation, acetylation, and sulfation of the sugar group. These intricate alterations serve to augment the structural diversity and functionality of glycosylated sterols. Concurrently, certain glycated sterols may undergo a fusion with fatty acids, culminating in the formation of ester bonds during the intricate and multifaceted process of biosynthesis. This fatty acid linkage can further increase the structural diversity of glycated sterols and affect their biological activity. The synthesized glycated sterols will enter their target sites, such as cell membranes, cell walls or organelles, via intracellular transport proteins or cell membrane channels.

Applications of Glycated Sterols

• First, glycated sterols enhance the structure and stability of cell membranes. They are found in cell membranes and increase membrane stability and stress resistance by interacting with the lipid bilayer.
• Second, glycated sterols play an important role in stress resistance in plants. Glycated sterols increase cell membrane stability, mitigate stress-induced cell membrane damage, and promote plant adaptation and survivability.
• Next, glycated sterols can act as dietary fiber, promoting gut health and may be beneficial in lowering cholesterol levels.
• Finally, glycated sterols can act as signaling molecules or inducers involved in plant interactions such as symbiosis, antagonism and defense responses.

Reference

1. Nyström, L. et al. Steryl glycosides and acylated steryl glycosides in plant foods reflect unique sterol patterns. European Journal of Lipid Science and Technology. 2012, 114(6): 656-669.