Quaternary isoquinoline alkaloids from Xylopia parviflora

Phytochemistry

Volumn 65, Issue 7, 2004, Pages 939-944

  Nishiyama, Yumi ^a   Moriyasu, Masataka ^a   Ichimaru, Momoyo ^a   Iwasa, Kinuko ^a   Kato, Atsushi ^a   Mathenge, Simon G ^b   Chalo Mutiso, Patrick B ^b   Juma, Francis D ^b  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b UNIVERSITY OF NAIROBI   (Kenya)

Author keywords

Annonaceae; Isoquinoline alkaloid; Xylopia parviflora

Indexed keywords

1,2 DEHYDRORETICULINE; 3,4 DIHYDRO 6,7 DIMETHOXY 2 METHYLISOQUINOLINIUM; 6,7 DIMETHOXY 2 METHYLISOQUINOLINIUM; DEHYDROCOREXIMINE; DEHYDRODISCRETINE; ISOQUINOLINE ALKALOID; JATRORRHIZINE; LOTUSINE; MENISPERINE; N METHYLCORYDINE; N METHYLPHOEBINE; N METHYLPURPUERINE; N,N DIMETHYLANOMURINE; OBLONGINE; PALMATINE; PLANT EXTRACT; PYCNARRHINE; STEPHARANINE; UNCLASSIFIED DRUG; XANTHOPLANINE; XYLOPIA PARVIFLORA EXTRACT; XYLOPINIDINE;

ANNONACEAE; ARTICLE; BARK; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; MEDICINAL PLANT; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; XYLOPIA PARVIFLORA;

ALKALOIDS; ANNONACEAE; ISOQUINOLINES; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT BARK; PLANT ROOTS; SPECTROPHOTOMETRY, ULTRAVIOLET;

ANNONACEAE; XYLOPIA;

EID: 1842715908     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2003.12.010     Document Type: Article

References (26)

1. Borkowski P.R., Horn J.S., Rapoport H. Role of 1,2-dehydroreticulinium ion in the biosynthetic conversion of reticuline to thebaine. J. Am. Chem. Soc. 100:1978;276-281.
2. Brophy J.J., Goldsack R.J., Forster P.I. The essential oils of the Australiane species of Xylopia (Annonaceae). J. Essent. Oil Res. 10:1998;469-472.
3. Colman-Saizarbitoria T., Gu Z.M., McLaughlin J.L. Two new bioactive monotetrahydrofuran annonaceous acetogenins from the bark of Xylopia aromatica. J. Nat. Prod. 57:1994;1661-1669.
4. Harrigan G.G., Bolzani V.da S., Gunatilaka A.A.L., Kingston D.G.I. Kaurane and trachylobane diterpenes from Xylopia aethiopica. Phytochemistry. 36:1994;109-113.
5. Harrigan G.G., Gunatilaka A.A.L., David G.I., Chan G.W., Johnson R.K. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea. J. Nat. Prod. 57:1994;68-73.
6. 13C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds. Can. J. Chem. 54:1976;2252-2260.
7. Jirovetz L., Buchbauer G., Ngassoum M.B. Investigation of the essential oils from the dried fruits of Xylopia aethiopica (West African "Peppertree") and Xylopia parviflora from Cameroon. Ernaehrung (Vienna). 21(7/8):1997;324-325.
8. Johns S.R., Lamberton J.A., Sioumis A.A. Alkaloids of Xylopia papuana. Aust. J. Chem. 21:1968;1383-1386.
9. Jossang A., Lebceuf M., Cave A., Pusset J. Alkaloids of the Annonaceae. 96. Dehydroxylopine and dehydrocorytenchine, novel isoquinoline alkaloids from Xylopia vieillardi. J. Nat. Prod. 54:1991;466-472.
10. Kato A., Moriyasu M., Ichimaru M., Nishiyama Y., Juma F.D., Nganga J.N., Mathenge S.G., Ogeto J.O. Examination of alkaloidal constituents of Zanthoxylum usambarense by a combination of ion-pair extraction and ion-pair chromatography using sodium perchlorate. Phytochem. Anal. 6:1995;89-95.
11. Koshiyama H., Ohkuma H., Kawaguchi H., Hsu H., Chen Y. Isolation of 1-(p-hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (demethylcoclaurine), an active alkaloid from Nelumbo nucifera. Chem. Pharm. Bull. 18:1970;2564-2568.
12. Lamaty G., Menut C., Bessiere J.M., Zollo P.H., Amvam F. The essential oil of Xylopia parviflora (A. Rich) Benth. from Cameroon. J. Essent. Oil Res. 1:1989;247-248.
13. Lee S., Chen C., Huang F., Chen C. Two dibenzopyrrocoline alkaloids from Litsea cubeba. J. Nat. Prod. 59:1996;80-82.
14. 13C NMR analysis of aporphine alkaloids. Phytochemistry. 18:1979;165-169.
15. Martins D., Osshiro E., Roque N.F., Marks V., Gottlieb H.E. A sesquiterpene dimer from Xylopia aromatica. Phytochemistry. 48:1998;677-680.
16. Menachery M.D., Lavanier G.L., Wetherly M.L. Simple isoquinoline alkaloids. J. Nat. Prod. 49:1986;745-778.
17. Moriyasu M., Ichimaru M., Nishiyama Y., Kato A. The acquisition of alkaloids from plant materials by a combination of ion-pair extraction and preparative ion-pair HPLC using sodium perchlorate. Bunseki Kagaku. 42:1993;659-665.
18. Moriyasu M., Ichimaru M., Nishiyama Y., Kato A. Isolation of alkaloids from plant materials by the combination of ion-pair extraction and preparative ion-pair HPLC using sodium perchlorate. I Magnoliae cortex. Natural Medicines. 48:1994;282-286.
19. Moriyasu M., Ichimaru M., Nishiyama Y., Kato A. Isolation of alkaloids from plant materials by the combination of ion-pair extraction and preparative ion-pair HPLC using sodium perchlorate. II Sinomeni Caulis et Rhizoma. Natural Medicines. 48:1994;287-290.
20. Moriyasu M., Ichimaru M., Nishiyama Y., Kato A. (R)-(+)-Isotembetarine, a quaternary alkaloid from Zanthoxylum nitidium. J. Nat. Prod. 60:1997;299-301.
21. Nishiyama Y., Moriyasu M., Sonoda M., Ichimaru M., Iwasa K., Kato A., Mathenge S.G., Juma F.D. Isoquinoline alkaloids from Monodora junodii. Natural Medicines. 54:2000;42.
22. 1H NMR chemical shift values for aromatic protons in 2,3,9. 10- and 2,3,10,11-tetrasubstituted tetrahydroprotoberberine alkaloids. Planta Med. 49:1983;162-164.
23. Ringdahl B., Chan R.P.K., Craig J.C. Circular dichroism of aporphines. J. Nat. Prod. 44:1981;80-85.
24. Ronsch H., Preiβ A., Schreiber K., Fernandez de Cordoba H. Structure elucidation and carbon-13 NMR of the new aporphine alkaloid 3-hydroxyglaucine. Liebigs Annalen der Chemie. 1983;744-752.
25. Tanahashi T., Su Y., Nagakura N., Nayeshiro H. Quaternary isoquinoline alkaloids from Stephania cepharantha. Chem. Pharm. Bull. 48:2000;370-373.
26. Wu J., Beal J.L., Wu W., Doskotch R.W. Alkaloids of thalictrum. XXXII. Isolation and identification of alkaloids from Thalictrum revolutum DC. fruit. J. Nat. Prod. 43:1980;270-277.