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Benzyl isoquinoline and tetrahydroprotoberberine alkaloids from Stephania rotunda Lour

Chemical investigation of Stephania rotunda Lour. growing in Vietnam led to the isolation and structural elucidation of benzylisoquinolines, coclaurine (1), dehassiline (2), as well as tetrahydroprotoberberines, stepholidine (3) and corynoxidine (4), along with 24 other alkaloids. These structures were determined on the basis of MS, NMR spectroscopic data and comparison with reported data. | Journal of Chemistry Vol. 44 3 P. 372 - 376 2006 BENZYL ISOQUINOLINE AND TETRAHYDROPROTOBERBERINE ALKALOIDS FROM STEPHANIA ROTUNDA LOUR. Received 16 February 2005 TRINH THI THUy1 II TRAN VAN SUNG1 K. FRANKE2 AND L. WESSjQHANN2 institute of Chemistry Vietnamese Academy of Science and Technology Department of Bioorganic Chemistry Leibniz-Institute of Plant Biochemistry Germany SUMMARy Chemical investigation of Stephania rotunda Lour. growing in Vietnam led to the isolation and structural elucidation of benzylisoquinolines coclaurine 1 dehassiline 2 as well as tetrahydroprotoberberines stepholidine 3 and corynoxidine 4 along with 24 other alkaloids. These structures were determined on the basis of MS NMR spectroscopic data and comparison with reported data. Keywords Stephania rotunda Menispermaceae benzylisoquinoline coclaurine dehassiline tetrahydroprotoberberine stepholidine corynoxidine. I - INTRODUCTION In a previous paper 1 we have reported the isolation and structural determination of a new isoquinolone alkaloid two novel tetrahydroprotoberberine alkaloids seven quaternary protoberberines four aporphines three oxoaporphines morphinane and proaporphine. In a continuing investigation of the alkaloid constituents from the tubers of this plant we describe in this paper the isolation and structural determination of benzylisoquinolines coclaurine 1 dehassiline 2 as well as tetrahydroprotoberberines stepholidine 3 and corynoxidine 4 . These structures were elucidated by MS NMR techniques and comparison with reported data. II - EXPERIMENTAL 1. General Optical rotation a D Digital Polarimeter Jasco DIP 1000. EIMS ADM 402 70 eV 372 Finigan TSQ 700. HR-ESI-MS BRUKER bioApex 70 eV. NMR VARIAN MERCURY 400 MHz UNITY 500 spectrometer at 499.83 MHz 1H and 100 125 MHz 13C 13C APT . Chemical shifts were referenced to internal TMS S 0 1H and CDCl3 S 77.0 13C or CD3OD s 49.0 13C . CC Silica gel 60 0.06 - 0.20 mm Merck for the first column silica gel 60 40 - 63 pm Merck for the .