beta-D-Galactopyranosid, (3 beta,5 alpha, 22 beta, 25S)-spirosolan-3-yl-O-beta-D-glucopyranosyl-(1=> 2)-O-(beta-D-xylopyranosyl-(1=> 3))-O-beta-D-glucopyranosyl-(1=> 4)- Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R23/25:Giftig beim Einatmen und Verschlucken.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S24/25:Berührung mit den Augen und der Haut vermeiden.
S22:Staub nicht einatmen.
Beschreibung
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.
Chemische Eigenschaften
Faintly beige powder
Verwenden
Tomatine is used as an antiproliferatice agent used in the suppression of breast adenocarcinoma cells.
Definition
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.
läuterung methode
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.]
Einzelnachweise
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)
beta-D-Galactopyranosid, (3 beta,5 alpha, 22 beta, 25S)-spirosolan-3-yl-O-beta-D-glucopyranosyl-(1=> 2)-O-(beta-D-xylopyranosyl-(1=> 3))-O-beta-D-glucopyranosyl-(1=> 4)- Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
