The Isolation and13C-NMR of Dihydrocorynantheol and Rhazimol (Deacetylakuammiline), Alkaloids from the Roots ofRhazya stricta

Planta Medica
1986.0

Abstract

The isolation and 13C-NMR spectra of dihydrocorynantheol and rhazimol from the roots of Rhazya stricta are reported. Rhazya stricta Decsne. (Apocynaceae) is a small glabrous, erect shrub which is abundantly distributed in Pakistan. The anti-cancer activity of some indole alkaloids isolated from the plant have been reported (1 —3). As a result of studies on the chemical constituents of the plant we have isolated dihydrocorynantheol and rhazimol (deacetylakuammiline). Dihydrocorynantheol has previously been reported from Aspidosperma marcgravianum (4). Rhazimol was previously reported by us from the leaves of R. stricta, (5, 6). Dihydrocorynantheol 1 was isolated from the roots of R. stricta, m.p. = 183°C; [α]D = 19° (CHCl3). Its IR, UV and mass spectral fragmentation pattern were identical to those reported in the literature (4). The 1H-NMR of dihydrocorynantheol (300 MHz, CDCl3) exhibited signals at δ 0.90 (3H, t, J = 7Hz, CH2-CH3), δ 1.60 (2H, m, CH3), 2.17 (1H, s, OH), δ 3.62 (2H, m, CH2OH), δ 6.79—7.43 (4H, m, aromatic protons), δ 9.57 (1H, bs, N-H). Rhazimol 2 was isolated from the alkaloidal extracts of the roots and its identity confirmed by comparison with spectroscopic data previously reported (5—8). The 13C-NMR spectra of dihydrocorynantheol and rhazimol (75 MHz, CDCl3) are shown in Table I. The assignments were made by analogy with established data for closely related indolenine (e.g. raucaffrinoline and vindolenine) (9, 10) or indole alkaloids (11). The 13C-NMR spectra of both alkaloids are consistent with the structures proposed earlier for rhazimol (5—8) and dihydrocorynantheol (4).

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