Sterol glycosides and acylglycosides

Abstract

The stntctlo'e, properties, distribution in nature, and biological activity of sterol glycosides and acylglycosides are reviewed.Sterols are one of the most widely distributed natural substances [1][2][3]. They exist in animals and plants in the free state and as derivatives. Glycoside and acylglycoside derivatives of sterols have been known for a long time. In the plant world, these compounds are found in higher plants [2,[4][5][6], algae [7], fungi [8][9][10], and bacteria [11][12][13][14][15][16]. In the animal kingdom, these substances have been identified in soft coral [17], holothuriae [18-20[, amphibians [211, snakes [21, 22], and birds [21,23]: Such a wide distribution in nature suggests that sterol glycosides and acylglycosides possess important physiological functions. Therefore, these compounds are constantly under intense scientific scrutiny. Sterol glycosides and acylglycosides are usually isolated from natural sources as very complicated mixtures that cannot always be separated into, the pure components. However, several physicochemical methods have recently been proposed for separating, analyzing, and identifying them [23][24][25][26][27][28][29][30][31][32][33][34]. Use of these methods greatly facilitates the investigation of glycosides and acylglycosides.Owing to the wide distribution in nature and the variety of physiological functions for glycosides and acylglycosides, research articles about them are published in a wide range of scientific literature. However, this subject has not yet been reviewed. The present work is intended to fill that gap. It should be noted that we pay the most attention to discreet natural compounds that can be isolated pure and for which the structures are reliably proved since this is where our interest lies. Substances that have been isolated as mixtures and are insufficiently characterized are examined in less detail.Some of the most widely distributed sterol glycosides are ~sitosterol 3-O-~D-glucopyranoside (1). This compound was isolated from higher plants early in the 20th century under various names: ipuranol, citrullol, trifolianol, etc. [35,36]. Later glycoside 1 was prepared by chemical synthesis via glycosylation of I~-sitosterol [37]. Direct comparision with this synthesized compound provided final structural proof tbr various natural samples of I [36]. Glycoside 1 is the most typical sterol glycoside of higher plants and is usually observed in preliminary phytochemical analysis of them. Hydrolysis of glycoside 1 by sulfuric acid in ethanol with boiling lbr 22 h yields [~-sitosterol and D-glucose [41]. The same result is obtained by hydrolysis in 6% HCI with heating lbr 50 min [46]. Hydrolysis of compound 1 to give ~sitosterol

Therapeutic Potential of Cholesteryl O-acyl α-glucoside Found in Helicobacter pylori

“…SGs and their acylated form are ubiquitously present in vascular plants, fungi and algae, while they have been relatively rarely found in bacteria [5,6]. Knowledge regarding the presence of SGs in animals is further limited [5,6]; cholesteryl -glucoside was found in the skin of snakes [7], birds [8] and human fibroblast cell lines [9,10], while cholesteryl -glucopyranuronic acid was isolated from the human liver [11][12][13]. However, the biological significance of endogeneously synthesized SGs in animals has not yet been characterized, since neither intracellular localization of steryl glycosides nor cloning of the genes responsible for sterol glycosyltransferase, a key enzyme for the biosynthesis of SGs, has been achieved in animal cells.…”

“…An esterified form of SG (phytosteryl 6'-O-acyl-glucoside) was then isolated from soybeans and potatoes [4]. SGs and their acylated form are ubiquitously present in vascular plants, fungi and algae, while they have been relatively rarely found in bacteria [5,6]. Knowledge regarding the presence of SGs in animals is further limited [5,6]; cholesteryl -glucoside was found in the skin of snakes [7], birds [8] and human fibroblast cell lines [9,10], while cholesteryl -glucopyranuronic acid was isolated from the human liver [11][12][13].…”

Lipase-catalyzed regioselective synthesis of steryl (6′-O-acyl)glucosides

“…Plant ASG fractions are complex mixtures of numerous ''molecular species'' differing in their fatty acid, sterol and/or sugar components. The occurrence, structure and properties of ASG have been reviewed elsewhere (Wojciechowski 1991;Kovganko and Kashkan 1999).…”

A New Pyrrole Alkaloid from Leccinum Extremiorientale

“…L. extremiorientale, commonly known as "Huanglaitou" in Chinese, is a very tasty mushroom. The exhaustive study on chemical constituents of some species in this family Boletaceae has been carried out [2][3][4][5]. Previous research on the chemical constituents of L. extremiorientale showed the presence of natural products including steroids, alkaloids, and monosaccharides [6,7].…”