Simple method for high purity acylated steryl glucosides synthesis

Abstract

The present work covers an important gap in the field of analytic standards synthesis of the plants minor component, the acyl steryl glucosides (ASG). A simple and powerful procedure that allows the synthesis of different ASG has been introduced. The regioselective acylation of steryl glucosides on the C–6–OH of the glucose was produced using sym‐collidine and acyl chloride. The reaction was optimized analyzing the conditions to maximize the isolated yield of the monoacylated product. Practical applications: The identification and quantification of acyl steryl glucosides (ASG) and steryl glucosides (SG) is a difficult task and has become increasingly important in the food, oil and biodiesel industries. There is a lack of simple synthetic approaches to prepare ASG and commercial sources of those compounds as analytical standards are expensive and sometime do not have the required purity. In this paper we are introducing a simple, powerful and versatile procedure that allows the synthesis of different ASG in a rapid and efficient way, producing the products in high purity that will enable them to be use as standards. The present work covers an important gap in the field of analytic standards synthesis of the plants minor component, the acyl steryl glucosides (ASG). A simple and powerful procedure that allows the synthesis of different ASG has been introduced.

A Novel Method for Extracting Steryl Glucosides From Soy Lecithin

“…The high purity SG and ASG products commercially available now are in milligram‐scale and very expensive. The need to develop new methods to produce high purity SG and ASG has drawn the attention of Paczkowski et al and Jager et al who reported methods to produce high purity ASG through enzymatic or chemical regioselective acylation of SG. More effort are required to exploit non‐chromatographic methods which can produce SG and ASG with high purity and also can be easily scaled up, so these compounds would be more affordable for research investigations.…”

The enzymatic biosynthesis of acylated steroidal glycosides and their cytotoxic activity

“…As illustrated in Figs. 1-3 and Supplementary Information S5-14, OsSGT1 specifically attacked the hydroxyl groups at C-3 and C-17 positions, but no activities towards hydroxyl groups at C-2 (13,18), C-7 (22), C-11 (23), C-12 (22), C-14(6), C-15 (14), C-16 (15, 16 and 19) and C-21 (23 and 24). When steroids having two potentially reactive hydroxyl groups, like 17α-hydroxypregnenolone (7) or androstenediol (10), were used as the substrate for OsSGT1-assisted glycosylation, only glycosides with a glycosyl substituent in C-3 position were detected in the reaction mixture, suggesting OsSGT1 exhibited prominent regioselectivity towards the 3-OH of both substrates (Supplementary Information Figs.…”

“…The structures of these glucosides were thus assigned to 3βglucosides (1a-7a and 10a) or 17β-glucosides (8a and 9a) of steroids based on 1 H NMR (1a-10a) and 13 C NMR (1a-10a) signals, HSQC (1a-2a, 4a-7a, 9a-10a), HMBC (7a-8a, 10a) and DEPT (7a, 10a) spectra ( Table 1, Supplementary Information Figs. S23-45 and Tables S5-13).…”

“…However, the content of ASGs was usually low in natural sources [7][8][9] . Moreover, the extraction routes were highly time-consuming and required laborious purification procedures [7][8][9]13 , resulting in poor yields and/or low purity of the final products. The production of ASGs was also achieved by chemical synthesis previously [10][11][12][13][14] .…”

“…Moreover, the extraction routes were highly time-consuming and required laborious purification procedures [7][8][9]13 , resulting in poor yields and/or low purity of the final products. The production of ASGs was also achieved by chemical synthesis previously [10][11][12][13][14] . However, these efforts often encounter a fundamental challenge, namely, regioselective acylation of single hydroxyl group of unprotected SGs in the late stage of the chemical synthesis of ASGs.…”