Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD
Publication type: Journal Article
Publication date: 2005-07-01
scimago Q1
wos Q1
SJR: 0.629
CiteScore: 6.5
Impact factor: 3.6
ISSN: 01633864, 15206025
PubMed ID:
16038537
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
Abstract
The metabolism of the phenolic 1-benzyltetrahydroisoquinoline alkaloids was studied in cell cultures of Macleaya and Corydalis species. The crude alkaloid fraction obtained from feeding experiments was investigated by application of the combined LC/NMR and LC/APCI-MS (/MS) techniques. Several metabolites were detected, and their structures (6 and 8-14) were identified. Bioconversion of the phenolic 1-benzyltetrahydroisoquinoline (2) into the pseudoprotoberberine (8) was demonstrated for the first time. LC/APCI-MS and LC/CD experiments carried out on a chiral column permitted the deduction of the major enantiomeric form of the chiral metabolites. Thus, the combination of NMR, MS, and CD data permitted the structural elucidation and stereochemical analysis of the metabolites in the extract matrix solution, without isolation and sample purification prior to the coupling experiments.
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GOST
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IWASA K. et al. Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD // Journal of Natural Products. 2005. Vol. 68. No. 7. pp. 992-1000.
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IWASA K., Cui W., Sugiura M., Takeuchi A., Moriyasu M., Takeda K. Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD // Journal of Natural Products. 2005. Vol. 68. No. 7. pp. 992-1000.
Cite this
RIS
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TY - JOUR
DO - 10.1021/np0402219
UR - https://doi.org/10.1021/np0402219
TI - Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD
T2 - Journal of Natural Products
AU - IWASA, Kinuko
AU - Cui, Wenhua
AU - Sugiura, Makiko
AU - Takeuchi, Atsuko
AU - Moriyasu, Masataka
AU - Takeda, Kazuyoshi
PY - 2005
DA - 2005/07/01
PB - American Chemical Society (ACS)
SP - 992-1000
IS - 7
VL - 68
PMID - 16038537
SN - 0163-3864
SN - 1520-6025
ER -
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BibTex (up to 50 authors)
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@article{2005_IWASA,
author = {Kinuko IWASA and Wenhua Cui and Makiko Sugiura and Atsuko Takeuchi and Masataka Moriyasu and Kazuyoshi Takeda},
title = {Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD},
journal = {Journal of Natural Products},
year = {2005},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/np0402219},
number = {7},
pages = {992--1000},
doi = {10.1021/np0402219}
}
Cite this
MLA
Copy
IWASA, Kinuko, et al. “Structural Analyses of Metabolites of Phenolic 1-Benzyltetrahydroisoquinolines in Plant Cell Cultures by LC/NMR, LC/MS, and LC/CD.” Journal of Natural Products, vol. 68, no. 7, Jul. 2005, pp. 992-1000. https://doi.org/10.1021/np0402219.