Sterols. C. Diosgenin¹

Abstract

Mares' Non-Pregnancy .Urine.-The butanol extract of 300 gallons of mares' non-pregnancy urine (previously hydrolyzed with hydrochloric acid) was hydrolyzed with an excess of aqueous potassium hydroxide solution. The neutral fraction was extracted with ether, which on evaporation yielded 209 g. of tarry residue. This residue was dissolved in a minimum amount of ethyl alcohol and treated with a 2% digitonin ethyl alcohol solution. On decomposition of the digitonide and sublimation of the residue under high vacuum at 130-140°, 0.34 g. of cholesterol was obtained, m. p. 144-146°. There was no depression in melting point when mixed with an authentic sample of cholesterol.

Identification and functional characterization of DzS3GT, a cytoplasmic glycosyltransferase catalyzing biosynthesis of diosgenin 3-O-glucoside in Dioscorea zingiberensis

“…and Trillium, produce pharmaceutical diosgenin, which usually exists in plants in the form of saponins and has been a starting material for the production of steroids over seven decades (Ding et al 1983;Jasim et al 2015;Marker et al 1940). Steroidal saponins vary in structure because of their various patterns of steroidal oxygenation and glycosylation (Challinor et al 2013;Wang and Hou 2008), which may be associated with a broad range of biological activities, such as cytotoxic (Wen et al 2015), antiulcer (Júnior et al 2015), hypolipidemic, anti-inflammatory, antioxidant, and antifungal effects (Sparg et al 2004;Weng et al 2014).…”

Scalable Synthesis of Cortistatin A and Related Structures

“…Starting from diosgenin, an abundant ingredient in wild Mexican yams, Marker achieved the commercialization of progesterone at Syntex by a 6-step sequence (known as “Marker's degradation”) in 1940. 11 In 1946, Sarett at Merck accomplished the first semisynthesis of cortisone ( 2 ) from bile acid in 36 steps. 12 In 1951, a group of chemists at Syntex, led by Carl Djerassi, achieved the semisynthesis of cortisone ( 2 ) from diosgenin in a 14-step sequence.…”

Physiological functions of solanaceous and tomato steroidal glycosides

“…Marker chemically converted a natural steroidal glycoside to a steroidal hormone, thereby consolidating the status of steroidal glycosides in the plant kingdom [1]. Subsequently, numerous searches that aimed to discover alternative raw materials for hormone synthesis were performed, especially in various species of plants belonging to Dioscoreacea and Liliaceae.…”