alpha-Solanine

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H302：삼키면 유해함

• 예방조치문구

  P264：취급 후에는 손을 철저히 씻으시오.

  P264：취급 후에는 손을 철저히 씻으시오.

  P270：이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.

  P501：...에 내용물 / 용기를 폐기 하시오.

alpha-Solanine 화학적 특성, 용도, 생산

• 개요

  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]²⁰_D - 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.

• 화학적 성질

  White solid

• 용도

  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.

• 정의

  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].

• 일반 설명

  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

• 위험도

  A poison.

• Mechanism of action

  In vitro studies have shown that alpha-Solanine's anti-cancer mechanism of action is induction of apoptosis, inhibition of cell proliferation and angiogenesis^[1]. It also regulates the nuclear factor-κB (NF-κB) signalling pathway in tumour cells and macrophages^[2].

• 부작용

  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].

• Purification Methods

  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.]

• 참고 문헌

  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)

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