Spectral Characterisation and Antiplasmodial Activity of Bisbenzylisoquinolines from Isolona ghesquiereina
| Autor: | David Ramanitrahasimbola, François Frappier, Dorothée Razafimahefa, Marie-Thérèse Martin, Lengo Mambu, Philippe Rasoanaivo |
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| Přispěvatelé: | Laboratoire de chimie et biochimie des substances naturelles, Muséum national d'Histoire naturelle (MNHN)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2000 |
| Předmět: |
Stereochemistry
Chemical structure Plasmodium falciparum Pharmaceutical Science Pharmacognosy Analytical Chemistry Antimalarials Isolona Drug Discovery Animals Molecule Pharmacology Molecular Structure biology Plant Extracts Alkaloid Organic Chemistry Biological activity Plants Isoquinolines biology.organism_classification [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry Molecular Biology/Biomolecules [q-bio.BM] Complementary and alternative medicine Annonaceae Molecular Medicine Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Planta Medica Planta Medica, Georg Thieme Verlag, 2000, 66, pp.537-540 |
| ISSN: | 1439-0221 0032-0943 |
| DOI: | 10.1055/s-2000-8610 |
| Popis: | From stem barks of Isolona guesquiereina three known bisbenzylisoquinolines were isolated and identified as (-)-curine, chondrofoline and isochondodendrine. Structures were established mainly on the basis of comparison of their physical and spectral data with published data for them and their methylated derivatives. Cleavage with sodium in liquid ammonia was necessary to unambiguously determine the stereochemistry of (-)-curine and subsequently establish its stereochemical link with chondrofoline, erroneously assigned as 7-O-methyl-(+)-curine. Complete and unambiguous 1H-, 15N- and 13C-NMR assignments of the three alkaloids were made by means of 2D-NMR techniques namely, COSY, HMQC, gs-HMQC, HMBC and NOESY. (-)-Curine, isochondrodendrine and their methylated derivatives were shown to exhibit strong in vitro antiplasmodial activity and in vivo activity was also observed for (-)-curine. |
| Databáze: | OpenAIRE |
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