Structural analyses of metabolites of phenolic 1- benzyltetrahydroisoquinolines in plant cell cultures by LC/NMR, LC/MS, and LC/CD

Journal of Natural Products

Volumn 68, Issue 7, 2005, Pages 992-1000

  Iwasa, Kinuko ^a   Cui, Wenhua ^a   Sugiura, Makiko ^a   Takeuchi, Atsuko ^a   Moriyasu, Masataka ^a   Takeda, Kazuyoshi ^b  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b EBARA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEILANTHIFOLINE; CORYTENCHINE; CRYPTOPINE; DEHYDROCORYTENCHINE; EPIBERBINE; LAUDANINE; PAPAVERINE; PHENOL DERIVATIVE; PHENOLIC 1 BENZYLTETRAHYDROISOQUINOLINE; PROTOPINE; PSEUDOPROTOBERBERINE; TETRAHYDROPALMATRUBINE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHIRALITY; CORYDALIS; DRUG ISOLATION; DRUG METABOLISM; DRUG STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PLANT CELL CULTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

CELLS, CULTURED; CORYDALIS; JAPAN; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PAPAVERACEAE; PHENOLS; STEREOISOMERISM; TETRAHYDROISOQUINOLINES;

CORYDALIS; MACLEAYA;

EID: 23844523169     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0402219     Document Type: Article

References (16)

1. Iwasa, K. In The Alkaloids; Cordell G. A., Ed.; Academic Press: New York, 1995; Vol. 46, pp 273-346.
2. Iwasa, K.; Nanba, H.; Lee, D.-U.; Kang, S.-I. Planta Med. 1997, 64, 748-751.
3. Iwasa, K.; Nishiyama, Y.; Ichimaru, M.; Moriyasu, M.; Kim, H.-S.; Wataya, Y.; Yamori, T.; Turuo, T.; Lee, D.-U. Eur. J. Med. Chem. 1999, 34, 1077-1083.
4. Iwasa, K.; Moriyasu, M.; Yamori, T.; Turuo, T.; Lee, D.-U.; Wiegrebe, W. J. Nat. Prod. 2001, 64, 896-898.
5. Iwasa, K.; Moriyasu, M.; Tachibana, Y.; Kim, H.-S.; Wataya, Y.; Wiegrebe, W.; Bastow, K. F.; Cosentino, L. M.; Kozuka, M.; Lee, K.-H. Bioorg. Med. Chem. 2001, 9, 2871-2884.
6. Preininger, V. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 29, pp 1-98.
7. Zenk, M. H. Pure Appl. Chem. 1994, 66, 2023-2028.
8. Iwasa, K.; Kuribayashi, A.; Sugiura, M.; Moriyasu, M.; Lee, D.-U.; Wiegreve, W. Phytochemisty 2003, 64, 1229-1238.
9. Hostettmann, K.; Potterat, O.; Welfender, J.-L. Pharm. Ind. 1977, 59, 339-347.
10. Wolfender, J.-L.; Ndjoko, K; Hostettmann, K. Curr. Org. Chem. 1998, 2, 575-596.
11. Wolfender, J.-L.; Ndjoko, K.; Hostettmann, K. Phytochem. Anal. 2001, 12, 2-22.
12. Kudo, K.; Ajima, K.; Sakamoto, M.; Saito, M.; Morris, S.; Castiglioni, E. Chromatography 1999, 20, 59-64.
13. Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H.; Shimanouchi, H.; Sasada, Y. Tetrahedron Lett. 1968, 40, 4251-4254.
14. Jeffs, P. W. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, pp 41-115.
15. Lu, S.-T.; Su, T.-L.; Kametani, T.; Ujiie, A.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans, 1 1976, 63-68.
16. Smallcombe, S. H.; Patt, S. L.; Keifer, P. A. J. Magn. Reson. Ser. A 1995, 117, 295-303.