STEMONIDINE

Description

This alkaloid occurs in the roots of Stemona japonica and behaves as a tertiary base. It has [α]²⁵_D - 7.65°C and is characterized as the hydrochloride which decomposes at 2600 C and the methiodide, decomposing at 2480 C. The alkaloid is not affected by HCI in either AcOH or EtOH and the oxidation products formed with KMn04 depend upon the conditions. If the oxidation is carried out in Me2CO a base is obtained which yields a crystalline methiodide, m.p. 235°C. On the other hand, KMn04 in dilute H2 S04 at lOoC yields two substances (a) a neutral compound, C16H230sN, m.p. 208°C; [α]_D - 58.30 which contains a lactone ring and one methoxyl group and (b) a substance CllH170 4N, m.p. 202°C; [α]_D - 24.17° which yields a semicarbazone, m.p. 258°C but contains no lactone group.
There is still ~ome doubt concerning the plant identity from which this alka_x0002_loid was isolated. Investigation by Suzuki suggested that it is not Stemona japonica as stated above but Stemona ovata Nakai.

Uses

Stemonidine is an alkaloid extracted from Stemona sessilifolia which acts as an insecticidal present in the leaves, stems and roots, as well as an alkaloidal constituents of interest that displays antitussive activity.

References

Suzuki.,J. Pharm. Soc., Japan, No. 352, 567 (1921)
Suzuki., ibid, 49, 78,457 (1929)
Suzuki., ibid, 51,43 (1931)
Suzuki., ibid, 54, 101 (1934)
Suzuki., ibid, 59, 184(1939)