Astrocasine: a new euphorbiaceae alkaloid

✍ Scribed by H.A. Lloyd

• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 264 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)90124-2

✦ Synopsis

An alkaloid representing a new type of carbon skeleton has been isolated from Astrocasia phyllantoides, a shrub of the Euphorbiaceae family. We have named it astrocasine and propose structure I on the following evidence. Astrocasine, q .p. 171-172O, [cl: -270" (ethanol), was assigned the formula C20W26N20 (1). The empirical formula was confirmed by high resolution mass spectrometry with a molecular ion peak at m/e 310.2044 (21 (Calcd. mass with C = 12.000, 310.2045). The base forms a monoperchlorate, C20H27N203C1, m.p. 149-151°, and a monomethiodide, C2lB29N2OI, m.p. 227-228O. The presence of one N-CH3 and absence of C-CH3, 0-CH3 or N-acetyl groups in astrocasine was shown by microanalysis and confirmed by n.m.r. The infrared @zCC> 1645, 1610, 1597, 1570 cm.-'), ultraviolet ethanol %x 263 qi, log E 4.09) and n.m.r. (3) spectra (4aromatic B, 67.31 -7.49; 2 olefinic H as 2 doublets centered atb7.08 and 6.43, J = 12 cpsl of astrocasine fit best a nearly planar a-cinnamoyl (41 N-dialkylated lactam structure.