Studies on the Alkaloids of Rutaceous Plants. XVIII. : Alkaloids of Xanthoxylum ailanthoides SIEB. et ZUCC. (Fagara ailanthoides (SIEB. et ZUCC.) ENGL.). (2). The Alkaloidal Content of Roots

Chemical Constituents from the Root Bark of Formosan Zanthoxylum Ailanthoides

“…15 The 1 H NMR spectrum of 2 was very similar to that of lanyuamide II, 16 except for the presence of the signals of a 2¢-hydroxy-N-isobutyl group [d 1.24 (6H, s, H-3¢, 4¢), 3.35 (2H, d, J = 6.4 Hz, H-1¢) and 5.92 (1H, br s, NH, D2O exchangeable)] in 2 instead of an N-isobutyl group in lanyuamide II. Therefore, the structure of hydroxy lanyuamide II was shown to be 2, which was also confirmed by COSY, 13 C, and NOESY experiments.…”

“…The other known compounds included twenty coumarins: xanthyletin, 11 luvangetin, 13 osthenol, 20 brosiparin, 21 aesculetin dimethyl ether, 22 braylin, 23 isopimpinellin, 23 phellopterin, 23 bergapten, 23 6,7,8-trimethoxycoumarin, 23 5,7,8-trimethoxycoumarin, 23 umbelliferone, 24 aurapten, 24 hydrangetin, 24 acetoxyaurapten, 24 O-methylcedrelopsin, 25 demethylsuberosin, 26 scopoletin, 27 5-methoxysuberenon, 28 and (-)-marmesin, 29 twenty-one benzo[c]phenanthridine alkaloids: 6-acetonyldihydrochelerythrine, 11 6-acetonyldihydronitidine, 11 arnottianamide, 11 isoarnottianamide, 11 integriamide, 23 norchelerythrine, 23 oxychelerythrine, 23 oxynitidine, 23 dihydronitidine, 23 nitidine CHCl 3 adduct, 23 decarine, 27 nitidine, 13 oxyavicine, 23 avicine CHCl 3 adduct, 30 dihydroavicine, 23 dihydrochelerythrine, 23 bocconoline, 31 chelerythrine, 31 6-methoxydihydrochelerythrine, 32 6-carboxymethyldihydrochelerythrine, 33 and tridecanonchelerythrine, 34 ten quinoline derivatives: confusameline, 20 (+)-platydesmine, 22 4-methoxy-1-methyl-2-quinoline, 23 haplopine...…”

Total synthesis of nitidine chloride

“…Found: C, 62.10; , 5.03; N, 3.47. Epimerization of cisto trans-JV-Methyl-3-(3',4'-methylenedioxyphenyl)-4-carboxy-6,7-dimethoxy-3,4-dihydro-1(2H)-isoquinolone (5). A solution of cis acid 4 (3.00 g, 7.78 mmol) in glacial acetic acid (150 mL) was heated at reflux for 16 h. The acetic acid was evaporated under reduced pressure and the resulting yellow powder was triturated with hot benzene (100 mL). Filtration gave a very pale yellow solid (2.82 g, 94%): mp 208-210 °C.…”

“…Caled for C21H19N3O6: C, 61.61; H, 4.68; N, 10.26. Found: C, 61.74; , 4.80; N, 10.41. traJis-JV-Methyl-3-(3',4'-methylenedioxyphenyl)-4-carboxymethyl-6,7-dimethoxy-3,4-dihydro-l(2fl)-isoquinolone (7).…”

“…Found: C, 63.30; H, 5.46; N, 3.36. trans-JV-Methyl-2,3-methylenedioxy-6,12-dioxo-8,9-dimethoxy-4b,5,6,10b,ll,12-hexahydrobenzo[c]phenanthridine (8). The acid 7 (3.60 g, 9 mmol) was stirred with polyiphosphoric acid) (36 g) exposed to air on a steam bath for 35 min during which time it changed from pale yellow through orange, then ruby, and finally to dark brown. The reaction mixture was hydrolyzed with water (400 mL) and extracted with chloroform (300 mL).…”