New alkaloids of Ungernia spiralis

N E W ALKALOIDS OF U n g e r n i a spiralis K h . A. K a d y r o v , A. A b d u s a m a t o v , a n d S. Y u . Y u n u s o v UDC 547.944/945 We have previously [1] reported the isolation from the roots of Ungernia spiralis of two alkaloids with mp 148-149°C and 141°C and the respective compositions CI?H17NO5 and C1yH19NO5. These bases proved to be new and were called ungspiroline (I) and ungspirolidine (II). We now give information concerning their structures. The UV spectrum of (D has three absorption maxima, at 229, 270, 310 nm (log e 4.44, 3.82, 3.78) characteristic for alkaloids of the maeronine type [2, 3]. IR spectrum of (1): ~max, era-l: 3300-3340 (>NH), 1715 (>C~---O), 1485; 1510, 1615 (aromatic ring). The NMR spectrum of (I) (CDCI3, T scale, JMN 100/100 MHz, internal standard IIMDS) showedthe following signals (ppm): singlets at 2.40 and 3.10 (aromatic protons at C9 and C12), 3.95 (2H, -O-CH20) , 6.52. (3H, -OCH3) and one-proton doublets from two olefinic protons at 3.55 and 4.57 ppm (J= llHz) corresponding to protons at C2 and CI. The mass spectrum of (I) contained, in addition to that of the molecular ion (M+ 315) the peaks of ions with m/e 301, 286, 272, 261, 243, 231, 171, and 56. The Hess methylation of (I) formed a substance with mp I04-I05°C identical with epimacronine [4] (mixed melting point, IR and mass spectra). All the information given shows that ungspiroline is possibly de-N-methylepimacronine and has the structure r~H30m~ih 0 The IJV spectrum of (II) rX ethan°l 230, 270, 309 nm (log a 4.30, 3.70, 3.63)] is similar to that of (I). The IR t max spectrum of (II) was Mso similar to that of (I) but differs in the "fingerprint w region. In the NNR spectrum of (II) there are singlets at (ppm) 2.53 and 3.07 (aromatic protons at C9 and C12), 4.02 (2H, - O - C H 2 0 ) , and 6.68 (3H, -OCI-I,a). In the mass spectrum of (II) there are the peaks of ions with m / e 31"/ (M+ ) 303, 288, 272, 261, 231, 171, and 56. A comparison of the facts given with those for (I) shows that (II) is possibly dthydroungsNroline. In actual fact, when ungspiroline was reduced by the Adams method a substance identical with the base (II) (in melting point and IR spectrum) was obtained. LITERATURE 1. 2. 3. 4. CITED Kh. A. Kadyrov and A. Abdusamatov, I ~ i m . Prirodn. Soedin., 426 (19777. A. W. Sa~gster and K. L. Stuart, Chem. Rev., 65, 69 (1965). W. C. Wildman and D. T. Bailey, J. Org. Chem., 3~3, 3749 (19687. H. Hauth and D. Stauffacher, Helv. Chim. Acta, 47, 185 (1964). Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Tashkent Agricultural Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, p. 719, SeptemberOctober, 1977. Original article submitted June 27, 1977. 606 0009-3130/77/1305- 0606 $07.50 © 1978 Plenum Publishing Corporation  (...truncated)