| Identification | Back Directory | [Name]
tuberostemonine | [CAS]
6879-01-2 | [Synonyms]
Nsc366235
Parathymine
TuberosteMonin
uberostemonine
tuberostemonine
TUBERSTEMONINE(P)
Tuberostemonine, 98%, from Stemona tuberosa L.
2β-[(2S,4S)-Tetrahydro-4-methyl-5-oxofuran-2-yl]stenine
(7aR,8aβ,11aβ,11bα,11cβ)-2β-[(2S,4S)-Tetrahydro-4-methyl-5-oxofuran-2-yl]-8β-ethyltetradecahydro-11β-methylfuro[2,3-h]pyrrolo[3,2,1-jk][1]benzoazepine-10-one
Furo[2,3-h]pyrrolo[3,2,1-jk][1]benzazepin-10(2H)-one, 8-ethyldodecahydro-11-methyl-2-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-, (2S,7aR,8R,8aS,11S,11aS,11bR,11cR)- | [Molecular Formula]
C22H33NO4 | [MDL Number]
MFCD11111456 | [MOL File]
6879-01-2.mol | [Molecular Weight]
375.506 |
| Chemical Properties | Back Directory | [Melting point ]
86～88℃ | [Boiling point ]
554.2±50.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
DMF:10.0(Max Conc. mg/mL);26.63(Max Conc. mM)
DMF:PBS (pH 7.2) (1:2):0.33(Max Conc. mg/mL);0.88(Max Conc. mM)
DMSO:1.0(Max Conc. mg/mL);2.66(Max Conc. mM) | [form ]
A solid | [pka]
8.90±0.70(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
This novel alkaloid has been isolated from Sternona sessilifolia and S. tuberosa
and was first given the formula C19H29O4N, subsequently altered to that given
above. It crystallizes in colourless needles from MeOH with 1 mole of solvent,
m.p. 65-88°C (dec.) and has [α]D - 25.4° (Me2CO). It is a non-phenolic,
tertiary base and yields a hydrobromide, m.p. 120°C (dec.) and a perchlorate,
m.p. 242°C (dec.). The methiodide monohydrate has m.p. 236-8°C (dec.) and
the methochloride, dihydrate, m.p. 172°C. A methosulphate has also been
prepared, m.p. 253°C (dec.). The base is not hydrolyzed by acids but in the
presence of excess PtO2 it gives the dihydro derivative, m.p. 133°C, furnishing a
hydrochloride, m.p. 281 ° C. Oxidation with KMnO4 gives a C17 compound,
whereas oxidation with silver oxide forms a neutral substance, C22H29O4N, m.p.
178°C which still contains the lactone groups and gives a positive Ehrlich
pyrrole reaction. | [Chemical Properties]
White needle-shaped crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Stemona tuberosa. | [Uses]
Tuberostemonine is elucidated as one of the major components of Radix Stemonae and has been shown to display therapeutic effects against cigarette smoke-induced acute lung inflammation. | [Definition]
ChEBI: A natural product found in Stemona phyllantha and Stemona tuberosa. | [Synthesis]
A kind of extraction method of P. parviflora alkaloid includes the following steps: (1)Take 2kg of P. parviflora herbal medicine, and physically pulverize it; (2) extract it twice by refluxing it with 4 liters of 95% ethanol solution for 3 | [storage]
Store at -20°C | [References]
Kondo, Suzuki, Satomi.,J. Pharrn. Soc., Japan, 54,96 (1934)
Kondo, Suzuki, Satomi., ibid, 59, 177 (1939)
Kondo, Suzuki, Satomi., ibid, 60, 149 (1940)
Kondo, Suzuki, Satomi., ibid, 61, 111 (1941)
Kaneko., Ann. Rep. ITSUU Lab. (Tokyo), 11,45 (1960)
Gotz, Bogri, Gray., Tetrahedron Lett., 707 (1961)
Edwards, Feniak, Handa., Can. J. Chern., 40,455,2416 (1962)
Crystal structure:
Harada et ai., Chern. Cornrnun., 460 (1967) |
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