[ソラニダ-5-エン-3β-イル]2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシド 化学特性,用途語,生産方法
解説
ソラニン．ソラツニンともいう．ジャガイモの新芽およびトマトに含まれるステロイドアルカロイドの配糖体．エタノールから針状晶として得られる．分解点285 ℃．[α]20D－59°(ピリジン)．アグリコンはソラニジン，糖はD-ガラクトース，D-グルコース，L-ラムノースよりなる(図)．原形質毒で，強力な溶血作用があり，頭痛，吐き気，胃炎などの中毒症状を起こすが，致命傷になることはまれである．農業用殺虫剤に用いられる．LD50 42 mg/kg(マウス，腹腔内)．
説明
This steroidal alkaloid is present in several Solanum species including S. nigrum,
S. Iycopersicum (tomato) and S. tuberosum (potato). The base crystallizes in
slender needles and shrinks markedly at 235°C. It has [α]
20D - 59.45° (pyridine)
or - 42.16° (dilute HCl) and is readily soluble in hot EtOH, sparingly so in H20
and virtually insoluble in CHCl 3 or Et2 0. The salts are mostly amorphous
although a crystalline hydrochloride has been prepared with m.p. 212°C (dec.).
It is not affected by alkalies but mineral acids hydrolyze it to solanidine (q.v.)
and one mole each of dextrose, galactose and rhamnose.
Pharmacologically, the alkaloid is a protoplasmic poison and a powerful
haemolytic. Poisoning by potatoes sometimes occurs although the results are not
usually fatal. The symptoms are nausea, headache, emesis and gastritis. With
large doses parenchymatous nephritis and haemoglobinuria occurs with, at times,
paralysis of the central nervous system and cardiac arrest. The alkaloid also
possesses local irritant properties.
化学的特性
White solid
使用
α-Solanine is produced as a by product in the synthesis of α-Chaconine. α-Chaconine is a glycoalkaloid displaying nerve toxin activity. Potential antifungal activity.
定義
ChEBI: A glycoalkaloid poison found in species of the nightshade family (Solanaceae), such as the potato (Solanum tuberosum). It is a trisccharide derivative of solanidine [(22beta)-solanid-5-en-3beta-ol].
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
危険性
A poison.
副作用
A small amount of α-solanine can cause common symptoms such as dizziness, nausea, abdominal pain, vomiting, and diarrhea. Excessive consumption of α-solanine can lead to convulsions, coma, and even death. Animal studies have shown that α-solanine can damage the reproductive system[1].
純化方法
Recrystallise -solanine from EtOH, 85% aqueous EtOH, MeOH or aqueous MeOH as dihydrate m 276-278o. It solubility in H2O is 25mg/L and 5% in pyridine, but it is very soluble in Et2O and CHCl3. The hydrochloride is gummy or amorphous but has been crystallised (m ~212o dec). It has insecticidal properties. [Kuhn et al. Chem Ber 88 1492 1955, Beilstein 21 III/IV 1402.]
参考文献
Desfosses.,lahresb., 2, 114 (1820)
Firbas., Monatsh., 10, 541 (1889)
Cazeneuve, Breteau., Compt. rend., 128,887 (1899)
Davis., Pharm. I., 15, 160 (1902)
Wittman., Monatsh., 26,445 (1905)
Colombano., Gazzetta, 38, 19 (1908)
Zemplen, Gerecs., Ber., 61,2294 (1928)
Schopf, Herrmann., ibid, 66, 298 (1933)
Oddo, Caronna., ibid, 67,446 (1934)
[ソラニダ-5-エン-3β-イル]2-O-(6-デオキシ-α-L-マンノピラノシル)-3-O-(β-D-グルコピラノシル)-β-D-ガラクトピラノシド 上流と下流の製品情報
原材料
準備製品