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| | tuberostemonine Basic information |
| Product Name: | tuberostemonine | | Synonyms: | tuberostemonine;(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;2β-[(2S,4S)-Tetrahydro-4-methyl-5-oxofuran-2-yl]stenine;Nsc366235;TUBERSTEMONINE(P);TuberosteMonin;Tuberostemonine, 98%, from Stemona tuberosa L.;Parathymine | | CAS: | 6879-01-2 | | MF: | C22H33NO4 | | MW: | 375.5 | | EINECS: | | | Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract | | Mol File: | 6879-01-2.mol |  |
| | tuberostemonine Chemical Properties |
| Melting point | 86～88℃ | | Boiling point | 554.2±50.0 °C(Predicted) | | density | 1.19±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | 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) |
| | tuberostemonine Usage And Synthesis |
| 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. | | 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. | | 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) |
| | tuberostemonine Preparation Products And Raw materials |
| Raw materials | Furo[2,3-h]pyrrolo[3,2,1-jk][1]benzazepin-10(2H)-one, 8-ethenyldodecahydro-11-methyl-2-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-, (2S,7aR,8R,8aS,11S,11aS,11bR,11cR)--->1H-Indole-1,2-dicarboxylic acid, 2,3,3a,6,7,7a-hexahydro-6-hydroxy-, 2-methyl 1-(phenylmethyl) ester, [2S-(2α,3aβ,6β,7aα)]- (9CI) | | Preparation Products | Furo[2,?3-?h]?pyrrolo[3,?2,?1-?jk]?[1]?benzazepin-?10(4H)?-?one, 8-?ethyl-?5,?6,?7,?7a,?8,?8a,?11,?11a-?octahydro-?11-?methyl-?2-?[(2S,?4S)?-?tetrahydro-?4-?methyl-?5-?oxo-?2-?furanyl]?-?, (7aR,?8R,?8aS,?11S,?11aR)?- |
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