The structure of the quaternary tetrahydroprotoberberine alkaloid escholidine is revised on the basis of 2D NMR spectroscopy and X-ray diffraction. In contrast to the originally reported constitution, escholidine bears an -OH group at C-9 and an -OCH3 group at C-10. The 1H and 13C NMR data and long-range 1H-13C and NOE interactions of escholidine are compared with those of thalifendine and tetrahydroberberrubine. The 15N NMR data of escholidine obtained by using long-range 1H-15N correlation experiments at natural abundance are also reported.
- MeSH
- berberinové alkaloidy chemie MeSH
- dioxoly chemie MeSH
- krystalografie rentgenová MeSH
- molekulární konformace MeSH
- molekulární struktura MeSH
- nukleární magnetická rezonance biomolekulární MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- berberinové alkaloidy MeSH
- dioxoly MeSH
- escholtzine MeSH Prohlížeč
Some 8-substituted derivatives of the protoberberine alkaloids palmatine (1a) and berberine (1b) have been prepared and investigated by 1D and 2D NMR spectroscopy (H-1, C-13, N-15). Complete NMR data for the 8-hydroxy (2), 8-methoxy (3), 8-ethoxy (4), and 8-trichloromethyl (5) 7,8-dihydro derivatives of 1a and 1b, as well as X-ray data for 8-methoxydihydroberberine (3b), 8-trichloromethyldihydropalmatine (5a), and 8-trichloromethyldihydroberberine (5b), are presented. The physicochemical data for all of these compounds are reviewed and compared with previously published values.
- MeSH
- alkaloidy chemická syntéza chemie MeSH
- berberin chemická syntéza chemie MeSH
- berberinové alkaloidy chemická syntéza chemie MeSH
- Berberis chemie MeSH
- krystalografie rentgenová MeSH
- léčivé rostliny chemie MeSH
- molekulární konformace MeSH
- molekulární struktura MeSH
- nukleární magnetická rezonance biomolekulární MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- srovnávací studie MeSH
- Názvy látek
- alkaloidy MeSH
- berberin MeSH
- berberinové alkaloidy MeSH
- palmatine MeSH Prohlížeč
