Pennsylvanine and pennsylvanamine, two new dimeric isoquinoline alkaloids

✍ Scribed by M. Shamma; J.L. Moniot

• Book ID: 104243354
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 230 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92236-1

✦ Synopsis

The in viva tumor inhibitory activity of thalicarplne ( 3) 2,3 --now chosen for clinical trial, prompts us to report the characterization of two new potential tumor inhibitors pennsylvanlne (1) and pennsylvanamine (21, phenolic analogs of 3, obtained from the giant meadow rue, Thalictrum polygamum Muhl. (Ranunculaceae),which is endemic throughout Pennsylvania. Pennsylvanine (11, C,,,H1sN208, [aI; +131° (c = 0.7, MeOH), a major alkaloid of the plant, was obtained as crystals mp 112-113O (ether). The uv spectrum, Aiz 284, 304 and 320sh nm (log a 4.26, 4.18 and 4.051, was reminiscent of that for thalicarpine (3) and showed both a hyperchromic effect and a bathochromic shift to imax MeCH-CH 284, 311 and 32Osh nm (log B 4.32, 4.29 and 4.151. The major fragments in the mass spectrum of l_, m/e 682 CM+), 476 (M+ -xl, 340 (M+ -yl, 324 (M+ -21, and 206 (x+, base), were identical with those in the spectrum of the related monophenolic aporphinebenzylisoqulnoline dimer thalidoxlne (4). 4 Diazomethane 0-methylation of 1 afforded (+)-thalicar-