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 hours;

(3) take the extracted solution and concentrate it to dryness;

(4) adopt D101 The concentrated solution was eluted by D101 macroporous adsorbent resin column (3kg) with the column diameter of 12M, and 3 liters of 40% methanol solution;

(5) Collecting the part containing p-phenylpodophyllum alkaloid and concentrating it in 200 ml of anhydrous ethanol, adding 3 ml of hydriodic acid to form a salt, and then cooling and crystallizing it in 0 degree overnight, then filtering and drying it, and obtaining 7 grams of the extract of p-phenylpodophyllum alkaloid.

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)