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| 融点 | 200-202° | | 比旋光度 | D25 -98° (c = 0.14 in methanol); D -113° (CHCl3) | | 沸点 | 532.75°C (rough estimate) | | 比重(密度) | 1.0159 (rough estimate) | | 屈折率 | 1.6400 (estimate) | | 貯蔵温度 | 2-8°C | | 溶解性 | DMSO: soluble0.5mg/mL, clear (warmed) | | 酸解離定数(Pka) | pKb 6.30(at 25℃) | | 外見 | powder | | 色 | white to beige | | 光学活性 (optical activity) | [α]/D -88 to -98°, c = 0.2 in methanol | | InChIKey | KOZCINYDCJVLDW-GCGBSLFCSA-N | | CAS データベース | 126-17-0(CAS DataBase Reference) | | NISTの化学物質情報 | Solasodine(126-17-0) |
| | ソランカルピジンともいう Usage And Synthesis |
| 解説 | ソランカルピジンともいう，ジャガイモSolanum，aculeatissinum，S.cyananthumなどに含まれるステロイドアルカロイド配糖体ソラソニン(solasonine)のアグリコン． | | 説明 | There is still some doubt as to whether this base occurs as such in Solanum
aviculare and S. xanthocarpum or whether it is an artifact formed from Sola_x0002_sonine (q.v.) during the extraction process. The base is laevorotatory having [α]20D - 92.4° (C6H6) and the following salts and derivatives have been prepared:
hydrochloride, m.p. 314°C; hydriodide, m.p. 293°C; oxalate, m.p. 248°C; tartrate, m.p. 222°C; picrate, m.p. 1.4l-2°C; picrolonate, m.p. 234°C; acetyl
derivative, m.p. 195°C; benzoyl compound, m.p. 2l6-7°C and the 3:5-dinitrobenzoyl derivative, m.p. 191.5-193°C. The alkaloid forms a sparingly soluble
digitonide and yields Diels's hydrocarbon on selenium dehydrogenation. | | 使用 | A potentially useful precursor. | | 使用 | antineoplastic, antiinflammatory | | 使用 | Solasodine is a potentially useful precursor for steroidal compounds and hormones, this is usually found in plants from the solanaceae family. It also has potent cytotoxic and anti-inflammatory effects. | | 使用 | Starting material for steroidal drugs. | | 定義 | ChEBI: Solasodine is an oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. It has a role as a plant metabolite, a teratogenic agent, a diuretic, an antifungal agent, a cardiotonic drug, an immunomodulator, an antipyretic, an apoptosis inducer, an antioxidant, an antiinfective agent, an anticonvulsant, a central nervous system depressant and an antispermatogenic agent. It is an azaspiro compound, an oxaspiro compound, an alkaloid antibiotic, a hemiaminal ether, a sapogenin and a steroid alkaloid. It is a conjugate base of a solasodine(1+). | | 一般的な説明 | This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | | Biochem/physiol Actions | Solasodine is a neuroprotective antioxidant glycoalkaloid of Solanum species. Solasodine increases superoxide dismutase (SOD), catalase (CAT),and glutathione (GSH) levels, while reducing lipid peroxidation (LPO) and nitric oxide (NO) levels in the brains of ischemia/reperfusion (I/R)-injury model in rats. Also, Solasonine displayed multiple activities including, anti-cancer and leishmanicidal activities. | | 安全性プロファイル | Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx. | | 純化方法 | Solasodine crystallises (as monohydrate) from MeOH as lustrous plates (on heating, the plates change to needles as they melt and resolidify in needles), or aqueous 80% EtOH, and sublimes at high vacuum. After recrystallisation from H2O, m 198-199o, then from Me2CO/H2O, m 199-201o, it has [] D 22 -109.3o (c 0.581, CHCl3). On TLC with silica gel G (*C6H6/absolute EtOH, 8:2) it has RF 0.45. IR (KBr): max at 10.3, 10.4, 11.2, 11.5 (azaoxaspirane bands). [Schreiber & Rnsch Tetrahedron 20 1939 1964, Uhle J Org Chem 27 656 1962, Kessar et al. Tetrahedron 27 2153 1971, Beilstein 27 III/IV 2000.] | | 参考文献 | Rochelmeyer, Chen., Arch. Pharm., 277,329 (1939)
Briggs., J. Chem. Soc., 3, (1942)
Briggs et al., ibid, 3013 (1950)
Absolute configuration:
Boll, Phillipsborn., Acta Chem. Scand., 19, 1365 (1965)
Synthesis:
Schreiber, Walther, Ronsch., Tetrahedron, 20, 1939 (1964)
Adam, Schreiber., Experientia, 21,471 (1965)
Adam, Schreiber., Tetrahedron, 22,3591 (1966) |
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