Ipecac alkaloids from Cephaelis acuminata

Phytochemistry

Volumn 52, Issue 6, 1999, Pages 1169-1176

  Itoh, Atsuko ^a   Ikuta, Yuki ^a   Baba, Yoshikazu ^a   Tanahashi, Takao ^a   Nagakura, Naotaka ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Amadori rearrangement compounds; Cephaeline; Cephaelis acuminata; Demethylcephaelines; Emetine; Ipecac alkaloids; Neocephaeline; Rubiaceae; Structure elucidation

Indexed keywords

10 O NORCEPHAELINE; 2' N (1'' DEOXY 1'' BETA DEXTRO FRUCTOPYRANOSYL)CEPHAELINE; 2' N (1'' DEOXY 1'' BETA DEXTRO FRUCTOPYRANOSYL)NEOCEPHAELINE; 7' O NORCEPHAELINE; 9 NORPROTOEMETINOL; ALKALOID DERIVATIVE; CEPHAELINE; EMETINE; IPECAC; ISOCEPHAELINE; NEOCEPHAELINE; PROTOEMETINE; PSYCHOTRINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG ISOLATION; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; RUBIACEAE; ULTRAVIOLET SPECTROPHOTOMETRY;

IPECAC; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT ROOTS; RUBIACEAE; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

CEPHAELIS ACUMINATA; CEPHAELIS IPECACUANHA; RUBIACEAE;

EID: 0033226387     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(99)00361-1     Document Type: Article

References (16)

1. Achari, B., Ali, E., Ghosh Dastidar, P. P., Sinha, R. R., & Pakrashi, S. C. (1980). Further investigations on the alkaloids of Alangium lamarckii. Planta Medica (Suppl.), 5-7.
2. Budzikiewicz H., Pakrashi S.C., Vorbrueggen H. Die Isolierung von Emetin, Cephaelin und Psychotrin aus Alangium lamarckii und die Identifizierung von Alamarckin mit N-Methylcephaelin. Diskussion der Massenspektren von Ipecacuanha-Alkaloiden. Tetrahedron. 20:(2):1964;399-408.
3. Fujii T., Ohba M., Suzuki H., Pakrashi S.C., Ali E. Syntheses of (-)-9-demethylprotoemetinol and (±)- and (-)-10-demethylprotoemetinols. Heterocycles. 19:(12):1982;2305-2308.
4. Fujii T., Ohba M. Quinolizidines. XVI. Chiral syntheses of 9-demethylcephaeline and 10-demethylcephaeline. Chemical and Pharmaceutical Bulletin. 33:(12):1985;5264-5269.
5. Hodge J.E., Fisher B.E. Whistler R.L., Wolfrom M.L. Methods in carbohydrate chemistry. vol. 2:1963;99 Academic Press, New York.
6. Itoh A., Tanahashi T., Nagakura N. Neoipecoside and 7-methylneoipecoside, new unusually-cyclized tetrahydroisoquinoline-monoterpene glucosides from Cephaelis ipecacuanha. Chemical and Pharmaceutical Bulletin. 37:(4):1989;1137-1139.
7. Itoh A., Tanahashi T., Nagakura N. Six tetrahydroisoquinoline-monoterpene glucosides from Cephaelis ipecacuanha. Phytochemistry. 30:(9):1991;3117-3123.
8. Itoh A., Tanahashi T., Nagakura N., Nayeshiro H. Tetrahydroisoquinoline-monoterpene glucosides from Alangium lamarckii and Cephaelis ipecacuanha. Phytochemistry. 36:(2):1994;383-387.
9. Janot M.M. Manske R.H.F., Holmes H.L. The alkaloids. Vol. 3:1953;363 Academic Press, New York.
10. Nagakura N., Höfle G., Coggiola D., Zenk M.H. The biosynthesis of the ipecac alkaloids and of ipecoside and alangiside. Planta Medica. 34:(4):1978;381-389.
11. Nagakura N., Itoh A., Tanahashi T. Four tetrahydroisoquinoline-monoterpene glucosides from Cephaelis ipecacuanha. Phytochemistry. 32:(3):1993;761-765.
12. Pakrashi S.C., Achari B. Demethylcephaeline, a new alkaloid from Alangium lamarckii. Characterization of AL 60, the hypotensive principle from the stem-bark. Experientia. 26:(9):1970;933-934.
13. Shamma M. The isoquinoline alkaloids. 1972;426 Academic Press, New York.
14. Tjan S.B., Quweland G.A.M.V.D. PMR investigation into the structure of some N-substituted 1-amino-1-deoxy-D-fructoses (amadori rearrangement products). Evidence for a preferential conformation in solution. Tetrahedron. 30:(16):1974;2891-2897.
15. Wiegrebe W., Kramer W.J., Shamma M. The emetine alkaloids. Journal of Natural Products. 47:(3):1984;397-408.
16. Yoshimatsu K., Shimomura K. VI Cephaelis ipecacuanha A. Richard (Brazilian ipecac): micropropagation and the production of emetine and cephaeline. Biotechnology in Agriculture and Foresty (Medicinal and Aromatic Plants IV). 21:1993;87-103.