トマチン 化学特性,用途語,生産方法
外観
白色～黄色～黄赤色粉末～結晶
解説
トマトに含まれるアルカロイドの一種。トマチンは，花、葉、茎に多く、熟した果実にはほとんど含まれない。多量摂取すると人体に対し毒性がある。化学式C50H83NO21
小学館 デジタル大辞泉について 情報 | 凡例
用途
トマチンは、溶液からコレステロールを沈殿させるための試薬として用いられている。また、特定のタンパク質抗原の免疫補助剤として知られている。
説明
This glycosidic alkaloid has been obtained from the dried leaves of Lycopersicum
pimpinelli/olium (Syn. Solanum racemigerum) and also occurs in L. esculentum;
L. hirsutum; L. peruvianum; L. peruvianum var. chutatum and L. putatum. The
alkaloid forms colourless needles from MeOH and has a somewhat indefinite
melting point about 270°C. It is laevorotatory with [α]
20D - 30° (pyridine) and
on hydrolysis with H2S04 yields tomatidine, I mole of galactose, 2 moles of
glucose and 1 mole of xylose. The tetrasaccharide unit is known as lycotetraose.
Partial hydrolysis with acid yields a series of products depending upon which,
and how many, of the sugar residues are split off from the molecule. Those
which have been isolated are: tomatidine lycotriose I (galactose-glucose-glucose);
tomatidine lycotriose II (galactose-glucose-xylose); tomatidine lycobiose
(galactose-glucose) and tomatidine-galactose.
化学的特性
Faintly beige powder
使用
Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
定義
ChEBI: A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galac
ose.
純化方法
Tomatine is recrystallised from MeOH, EtOH, aqueous EtOH or dioxane/NH3. It is almost insoluble in pet ether, Et2O or H2O. [Reichstein Angew Chem 74 887 1962, Beilstein 27 III/IV 1954.]
参考文献
Fontaine et al., Arch. Biochem., 18,467 (1948)
Kuhn, Low., Ber., 81, 552 (1948)
Kuhn, Low, Gauhe., ibid, 83,448 (1950)
Fontaine et al., Arch. Biochem., 27,461 (1950)
Fontaine et al., J. Amer. Chern. Soc., 73, 878 (1951)
Kuhn, Low, Trischmann., Angew. Chern., 68, 212 (1956)
Kuhn et al., Ber., 90, 203 (1957)
トマチン 上流と下流の製品情報
原材料
準備製品