スチグマステロール

解説スチグマステロール,融点170 ℃．[α]20D－50°(クロロホルム)．水に不溶，有機溶媒に可溶．側鎖の二重結合の選択的オゾン分解で生じるアルデヒドは，プロゲステロン系のステロイドホルモンの重要な合成原料となる．森北出版「化学辞典（第2版）

説明Stigmasterol is a natural plant sterol that can be isolated from certain seed oils and herbs, including those used for therapeutic purposes. Dietary consumption of phytosterols, including stigmasterol, may have beneficial health effects in adults, particularly against cancer and ulceration. Alternatively, phytosterols may contribute to inflammation and intestinal failure-associated liver disease in young individuals.

使用Stigmasterol has been used as a phytosterol compound to test its anti-proliferative property in breast cancer cell culture and its effect on liver X receptor-α (LXRA) activation. It may be used as an internal standard for the quantification of yeast cell wall sterols using gas chromatography–mass spectrometry (GC-MS) analysis, and in the preparation of lipid monolayers.

一般的な説明Stigmasterol is a plant sterol that comprises an unsaturated bond between C22 and C23. It is found in foods like margarines and yogurts. Stigmasterol is synthesized from the mevalonate pathway and is present during development stages in plants.

純化方法Stigmasterol is best purified via the tetrabromide-acetate. The impure sterol (3g) is acetylated with Ac2O (60mL) by refluxing for 1.5hour. The mixture is cooled at 20o for 1hour, and the crude acetate is collected. The acetate (3g) in Et2O (30mL) is then treated with Br2/AcOH (38mL, from 5g Br2 in 100mL AcOH), and after cooling at 6o overnight, the tetrabromoacetate is filtered off and washed with Et2O. After six recrystallisations from CHCl3/MeOH the tetrabromoacetate has m 194-196o. This product (1g) in AcOH (12mL) and Zn dust (1g) is refluxed for 1.5hours, filtered hot, diluted with H2O (30mL) and extracted with Et2O. The extract is washed with dilute aqueous sodium sulfite, then H2O, the extract is dried (Na2SO4) and the stigmasterol acetate (~550mg) is recrystallised (4x) from EtOH and twice from MeOH/CHCl3 (2:1) to give the acetate with m 139-148o. This acetate (400mg) is hydrolysed in boiling 10% alcoholic KOH (1mL) for 1hour. Then H2O (30mL) is added and the mixture is extracted with Et2O. The extract is washed with aqueous Na2CO3, then H2O, the solvent is distilled off and the residue is recrystallised (3x) from 95% EtOH to give ~110mg of pure stigmasterol. It is dried in a vacuum over P2O5 for 3hours at 90o. The purity is checked by NMR. The acetate crystallises from MeOH with m 145o, [] D 25 -56o (c 2, CHCl3). [Byerrum & Ball Biochemical Preparations 7 86 1959, Thornton et al. J Am Chem Soc 62 2006 1940, Colin et al. Anal Chem 51 1661 1979, Beilstein 6 IV 4170.]