Limogine and himalayamine: A new class of alkaloids

✍ Scribed by Daovi P. Allais; Hélène Guinaudeau; Alan J. Freyer; Maurice Shamma; Nemai C. Ganguli; Bani Talapatra; Sunil K. Talapatra

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 275 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81950-4

✦ Synopsis

The novel alkaloids himalayamine (1;) and limogine (2) have been obtained from Meconopsis villosa (Papaveraceae) and Corydalis claviculata (Fumariaceae), respectively. In spite of the fact that some forty-two plant species fall within the ambit of the genus Meconopsis (Papaveraceae), only a few have had their rich alkaloidal content investigated. 1 We, therefore, initiated a study of Meconopsis villosa (Hook.f.) G. Taylor which was collected in the vicinity of Darjeeling, in northern India. 2 Fractionation of the alkaloids yielded himalayamine, C20H1706N, mp 218" (CHC13-petroleum ether), whose UV spectrum with X max 293 nm denotes an isoquinoline alkaloid of a somewhat unusual nature since the uv maximum for most isoquinolines is in the 280-290 nm region. The two most important features of the mass spectrum are a molecular ion peak m/z 367, and a base peak m/z 350 formed by loss of hydroxide from the molecular ion. 3 It was thus logical to assume the presence of an alcohol function in the molecule. Analysis of the 'H NMR spectrum led to tentative structure 1 for himalayamine. Obvious features are an N-methyl singlet, two methylenedioxys, and four aromatic protons, two as singlets and