Research Collection. Doctoral Thesis. ETH Library. Author(s): Sagen, Anne-Lise. Publication Date: 2002
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1 Research Collection Doctoral Thesis Phytochemical and biological investigations on Clathrotropis glaucophylla (Fabaceae), an ingredient of Yanomamï curare, emphasizing on quinolizidine alkaloids Author(s): Sagen, Anne-Lise Publication Date: 2002 Permanent Link: Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library
2 Diss. ETH No PHYTOCHEMICAL AND BIOLOGICAL INVESTIGATIONSON CLATHROTROPISGLAUCOPHYLLA(FABACEAE), AN INGREDIENTOF YANOMAMICURARE, EMPHASIZING ON QUINOLIZIDINEALKALOIDS A dissertation submittedto the SWISS FEDERAL INSTITUTEOF TECHNOLOGYZÜRICH for the degree of Doctor of Natural Sciences Presented by ANNE-LISE SAGEN Pharmacist (University of Oslo, Norway) born February 7, 1973 Norway Accepted on the recommendationof Prof. Dr. Otto Sticher, examiner Prof. Dr. Ihsan Qahs, co-examiner Prof. Dr. Gerd Folkers, co-examiner Dr. Jörg Heilmann,co-examiner Zürich 2002
3 SUMMARY SUMMARY In the present study the bark of the Yanomami' curare plant, Clathrotropis glaucophylla Cowan, was investigated for its contents of secondarymetabolites. Clathrotropis is a small genus ofthe Fabaceae family, with six species endemicto the tropicalsouth America. They are small to medium trees with very large leaves, and the fruits are oblong and flat, with large seeds. C. glaucophyllawas collected in the rainforests ofthe upperorinoco in Venezuelain Ethnobotanicalinvestigationhas revealedthat the species C. glaucophyllaand C. macrocarpa(wapu kohi) are of great economic impor tanceto the YanomamiAmerindians in Venezuela,the seeds playinga significantrole in alimentation, and the bark being used as ingredient ofcurare arrow poison. Fractionation ofthe alkaloid and dichloromethaneextracts ofc. glaucophyllabark, by means of various Chromatographie methods (VLC, CC, HPLC), led to the isolation of 27 natural Compounds. From the alkaloid extract a new quinolizidine alkaloid, (-)- 13a-hydroxy-15a-(l-hydroxyethyl)-anagyrine, ((-)-clathrotropine), was isolated together with elevenknown quinolizidine alkaloids: (-)-anagyrine,(-)-thermopsine, (-)- baptifoline,(-)-epibaptifoline, (-)-rhombifoline, (-)-tinctorine, (-)-cytisine, (-)-Ar-methylcytisine, (-)-lupanine, (-)-6a-hydroxylupanineand (+)-5,6-dehydrolupanine. The investigation of the dichloromethane extract led to the isolationof two new betulinic acid derivatives, 23-0-(4'-hydroxy-3'-methoxy-cinnamoyl)betulinicacid and (4'-hydroxy-3',5'-dimethoxy-cinnamoyl)betulinic acid, one new a-pyrone,5(s),6(s)-6- (2-hydroxy-l-methylpropyl)-3,5-dimethyl-5,6-dihydro-2H-a-pyrone, and one new isocoumarin, 6-hydroxy-8-methoxy-3-«-pentylisocoumarin,in addition to eleven known Compoundswhich were identifiedas: betulinic acid, ß-amyrin, glutinol, ß-sitosterol, stigmasterol, 7ß-hydroxysitosterol, 7ß-hydroxystigmasterol, ß-sitosterol-3-O-ß-glucoside, stigmasterol-3-o-ß-glucoside, 2'-0-methylevernicacid, and confluentic acid. Structure elueidation ofthe isolatedcompounds was carried out by means of spec troscopic,spectrometric and physical methods: 1D and 2D NMR experiments(lh, 13C, COSY, HSQC, HMBC, ROESY, HSQC-TOCSY and INADEQUATE), UV, MS, and [ab- This is the first phytochemical study on C. glaucophylla, which showed this plant to aecumulate a great variety of quinolizidine alkaloids as well as triterpenes, sterols, depsides and isocoumarins.it is the first time quinolizidine alkaloids have been isolated
4 from an arrow poison ingredient, and it is also the first report on Clathrotropis species being used for arrow poison.
5 ZUSAMMENFASSUNG ZUSAMMENFASSUNG In der vorliegendenarbeitwurde die Rindeder Yanomami CurarepflanzeClathrot ropis glaucophyllacowanauf ihre Inhaltsstoffeuntersucht. Clathrotropis ist eine kleine Gattung aus der Familie der Fabaceae, mit sechs einheimischen Arten im tropischen Südamerika. Es handeltsich um kleine bis mittelgrosse Bäume mit sehr grossenblät tern. Die Früchte sind länglichund flachmit grossen Samen.EthnobotanischeUntersu chungen haben gezeigt, dass die Arten C. glaucophyllaund C. macrocarpa(wapu kohi) ökonomisch sehr wichtig für die Yanomami Indianer in Venezuelasind. Die Samen spielen eine bedeutsamerolle in der Ernährung und die Rinde wird als Pfeilgiftbe standteil (Curare) verwendet. Die Fraktionierungder Alkaloid- und Dichlormethanextraktevon C. glaucophylla, mittels verschiendenerchromatographischermethoden (VLC, CC, HPLC) führte zur Isolierung von 27 Naturstoffen. Aus dem Alkaloidextrakt wurde ein neues Chinolizidin- Alkaloid (-)-13a-Hyroxy-15a-(l-hydroxyethyl)-anagyrin,(-)-Clathrotropin isoliert, sowie elf schon bekannte Chinolizidin-Alkaloide: (-)-Anagyrin, (-)-Thermopsin, (-)- Baptifolin, (-)-Epibaptifolin, (-)-Rhombifolin, (-)-Tinctorin, (-)-Cytisin, (-)-JV-Methylcytisin, (-)-Lupanin, (-)-6oc-Hydroxylupanin und (+)-5,6-Dehydrolupanin.Die Untersu chung des Dichlormethanextraktesführte zur Isolierung von zwei neuen Betulinsäurederivaten: 23-0-(4'-Hydroxy-3'-methoxy-cinnamoyl)-betulinsäure und 23-0(4'- Hydroxy-3',5'-dimethoxy-cinnamoyl)-betulinsäure, einemneuen a-pyron (5(5),6(5)-6- (2-Hydroxy-l-methylpropyl)-3,5-dimethyl-5,6-dihydro-2H-a-p}a:on) und einem neuen Isocoumarinderivat (6-Hydroxy-8-methoxy-3-n-pentylisocoumarin), sowie elf bekannten Substanzen,die als Betulinsäure, ß-Amyrin, Glutinol, ß-Sitosterol, Stigmasterol, 7ß-Hydroxysitosterol, 7ß-Hydroxystigmasterol, ß-Sitosterol-3-O-ß-glucosid, Stigmasterol-3-O-ß-glucosid, 2'-0-Methylevernicsäureund Confluenticsäure identifi ziert wurden. Die Strukturaufklärung erfolgtemittels 1D und 2D NMR (1H, 13C, COSY, HSQC, HMBC, ROESY, HSQC-TOCSY and INADEQUATE)und UV-Spektroskopie, Massenspektrometrie, sowie optische Drehung. Es handelt sich hier um die erste phytochemische Untersuchung von C. glauco phylla. Sie zeigt, dass die Pflanze eine grosse Fülle verschiedenerchinolizidin-alka loide, sowie Triterpene, Sterole, Depside und Isocoumarine akkumuliert. Dies ist das
6 erste Mal, dass Chinolizidin-Alkaloide aus einer Pfeilgiftpflanze isoliert wurden. Ferner ist es der erste Bericht, dass Clathrotropis-AxX&a. zur Herstellung von Pfeilgiften verwendet werden.
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