Thalidoxine, a New Aporphine-Benzylisoquinoline Alkaloid

✍ Scribed by M. Shamma; S.S. Salgar; J.L. Moniot

• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 196 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96258-6

✦ Synopsis

25 The dimeric alkaloid thalidoxlne (A), C,0H,gN205, [c(], Cl130 (c 0.2 MeCH) has been obtained from Thalictrum dioicum L. (Ranunculaceae) as an amorphous base. The lr spectrum (CXCIJ) contain--1 ed phenolic hydroxyl absorbance at 3540 cm . The uv spectrum AMeCH max 275, 296sb and 310sh (log6 4.23, 4.08 and 4.02) was reminiscent of that for the well-known thalicarpine ($,2 and gave no bathochromic shift in base. The mass spectrum m/e 632 CM+), 476 CM -xl, 340 (M -y), 324 (M -z) and 206 (x, base), pointed to the fact that thalidoxlne was an aporphine-benzylisoquinoline dlmer with a phenolic function located on the benzylisoquinoline ring C. The nmr spectrum (Table ), with signals for six methoxyl groups indicated that 1 was an 0-demethyl analog of thalicarpine (31,