Sapogenins, steroidal

Progesterone can be manufactured from cholesterol, from certain steroid sapogenins and from stigmasierol. 

Diosgenin (Fig. 4) is a steroid sapogenin produced by Dioscorea species. This natural product is used as a precursor for the commercial synthesis of medicinal steroids such as prednisolone, dexamethasone, norethisterone, and metenolone, among others. Microtuber-derived cell suspensions of Dioscorea doryophora were able to accumulate diosgenin at concentrations as high as 3.5% g dw. Embryogenic callus of Tribulus terrestris were also able to accumulate diosgenin (170.7 1.0 pg/g dw). ... 

The two major types of steroidal sapogenin are diosgenin and hecogenin. Steroidal saponins are used in the commercial production of sex hormones for clinical use. For example, progesterone is derived from diosgenin. 

Pharmaceutical steroids are usually synthesized from cholic acid obtained from cattle or steroid sapogenins found in plants. Further modifications of these steroids have led to the marketing of a large group of synthetic steroids with special characteristics that are pharmacologically and therapeutically important (Table 39-1 Figure 39-3). 

Schreiber, K., Aurich, O., and Osske, G., Solanum alkaloids. XVBI. Thin-layer chromatography of Solanum steroid alkaloids and steroidal sapogenins, J. Chromatogr., 12, 63, 1963 Chem. Abs., 60, 4442h, 1964. 

Gupta, R.K., Jain, D.C. and Thakur, R.S. (1986a) Minor steroidal sapogenins from fenugreek seeds, Trigonella foenum graecum. Journal of Natural Products 49(6), 1 153. 

Taylor, W.G., Zaman, M.S., Mir, Z., Mir, P.S., Acharya, S.N., Mears, G.J. and Elder, J.L. (1997) Analysis of steroidal sapogenins from amber fenugreek (Trigonella foenum-graecum) by capillary gas chromatography and combined gas chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry 45(3), 753-759. 

Sitosterol is a steroid sapogenin that has been isolated from ginseng. Approximately 50-60% of a dose of (3 -sitosterol is absorbed from the gastrointestinal tract in rats (79). After oral administration of radiolabeled ginsenoside Rgl, blood radioactivity peaked at 2.1 hours. Bioavailability was 49% (80). 

Piancatelli, G., and Scettri, A., Synthesis of a C23 spiroketalic steroidal sapogenin, Gazz. Chim. Ital., 104, 343, 1974. 

BUTCHERS BROOM The roots of Ruscus dculentus contain a mixture of steroid sapogenins called ruscogenins which are structurally similar to diosgenin. These have been formulated into topical preparations for varicose veins and haemorrhoids. 

HECOGENIN Hecogenin is a steroidal sapogenin, which can be obtained from the waste juice from the preparation of sisal from the leaves of A a-ve sisalana (Engelm.)... 

Structure. Digitonin is made up of the rare steroid sapogenin digitogenin linked through the 3/3-hydroxyl group to a five-unit sugar moiety ... 

Acetolysis [1, 966, before references]. Marker11 discovered a method for utilizing the steroid sapogenin diosgenin (1) for the synthesis of steroid hormones consisting in acetolysis with acetic anhydride at an elevated temperature to the furostadiene diacetate (2), an unsaturated compound which is convertible in four simple steps into progesterone (6). 

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