A photometric screening method for dimeric naphthylisoquinoline alkaloids and complete on-line structural eludication of a dimer in crude plant extracts, by the LC−MS/LC−NMR/LC−CD Triad

G. Bringmann (Corresponding Author), M. Wohlfarth, Heiko Rischer, M. Heubes, W. Saeb, S. Diem, M. Herderich, J. Schlauer

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Abstract

An efficient evaluation procedure for the chemical screening and on-line structural elucidation of dimeric naphthylisoquinoline alkaloids has been developed. The method is based on the lead tetraacetate oxidation of the central binaphthalene core of the alkaloids. UV spectra of the extracts after addition of the oxidant show, in the presence of naphthylisoquinoline dimers, the appearance of a characteristic long-wavelength absorption indicative of dinaphthoquinones. The efficiency and relevance of the method has been demonstrated in the discovery of a constitutionally and configurationally new dimeric naphthylisoquinoline alkaloid, named ancistrogriffithine A (4), from the previously uninvestigated Asian liana Ancistrocladus griffithii. After verification of this screening result by LC−ESI-MS/MS, the constitution and the relative configuration of the compound were elucidated on line, by LC−NMR and LC−CD on the extract. Using an LC−NMR-WET-ROESY experiment, it was possible for the first time to determine the relative axial configuration of a natural biaryl compound on line, by observing long-range ROE interactions. Finally, an oxidative degradation right on the extract delivered the absolute configuration of 4, without isolation of the alkaloid. Ancistrogriffithine A is the as yet only dimeric naphthylisoquinoline from an Asian Ancistrocladaceae plant.
Original languageEnglish
Pages (from-to)2571-2577
Number of pages7
JournalAnalytical Chemistry
Volume73
Issue number11
DOIs
Publication statusPublished - 2001
MoE publication typeA1 Journal article-refereed

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Plant Extracts
Alkaloids
Dimers
Screening
Oxidants
Degradation
Wavelength
Oxidation
Experiments

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@article{6d79e695005b4da5b4976e887d85e83d,
title = "A photometric screening method for dimeric naphthylisoquinoline alkaloids and complete on-line structural eludication of a dimer in crude plant extracts, by the LC−MS/LC−NMR/LC−CD Triad",
abstract = "An efficient evaluation procedure for the chemical screening and on-line structural elucidation of dimeric naphthylisoquinoline alkaloids has been developed. The method is based on the lead tetraacetate oxidation of the central binaphthalene core of the alkaloids. UV spectra of the extracts after addition of the oxidant show, in the presence of naphthylisoquinoline dimers, the appearance of a characteristic long-wavelength absorption indicative of dinaphthoquinones. The efficiency and relevance of the method has been demonstrated in the discovery of a constitutionally and configurationally new dimeric naphthylisoquinoline alkaloid, named ancistrogriffithine A (4), from the previously uninvestigated Asian liana Ancistrocladus griffithii. After verification of this screening result by LC−ESI-MS/MS, the constitution and the relative configuration of the compound were elucidated on line, by LC−NMR and LC−CD on the extract. Using an LC−NMR-WET-ROESY experiment, it was possible for the first time to determine the relative axial configuration of a natural biaryl compound on line, by observing long-range ROE interactions. Finally, an oxidative degradation right on the extract delivered the absolute configuration of 4, without isolation of the alkaloid. Ancistrogriffithine A is the as yet only dimeric naphthylisoquinoline from an Asian Ancistrocladaceae plant.",
author = "G. Bringmann and M. Wohlfarth and Heiko Rischer and M. Heubes and W. Saeb and S. Diem and M. Herderich and J. Schlauer",
year = "2001",
doi = "10.1021/ac001503q",
language = "English",
volume = "73",
pages = "2571--2577",
journal = "Analytical Chemistry",
issn = "0003-2700",
publisher = "American Chemical Society",
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}

A photometric screening method for dimeric naphthylisoquinoline alkaloids and complete on-line structural eludication of a dimer in crude plant extracts, by the LC−MS/LC−NMR/LC−CD Triad. / Bringmann, G. (Corresponding Author); Wohlfarth, M.; Rischer, Heiko; Heubes, M.; Saeb, W.; Diem, S.; Herderich, M.; Schlauer, J.

In: Analytical Chemistry, Vol. 73, No. 11, 2001, p. 2571-2577.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - A photometric screening method for dimeric naphthylisoquinoline alkaloids and complete on-line structural eludication of a dimer in crude plant extracts, by the LC−MS/LC−NMR/LC−CD Triad

AU - Bringmann, G.

AU - Wohlfarth, M.

AU - Rischer, Heiko

AU - Heubes, M.

AU - Saeb, W.

AU - Diem, S.

AU - Herderich, M.

AU - Schlauer, J.

PY - 2001

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N2 - An efficient evaluation procedure for the chemical screening and on-line structural elucidation of dimeric naphthylisoquinoline alkaloids has been developed. The method is based on the lead tetraacetate oxidation of the central binaphthalene core of the alkaloids. UV spectra of the extracts after addition of the oxidant show, in the presence of naphthylisoquinoline dimers, the appearance of a characteristic long-wavelength absorption indicative of dinaphthoquinones. The efficiency and relevance of the method has been demonstrated in the discovery of a constitutionally and configurationally new dimeric naphthylisoquinoline alkaloid, named ancistrogriffithine A (4), from the previously uninvestigated Asian liana Ancistrocladus griffithii. After verification of this screening result by LC−ESI-MS/MS, the constitution and the relative configuration of the compound were elucidated on line, by LC−NMR and LC−CD on the extract. Using an LC−NMR-WET-ROESY experiment, it was possible for the first time to determine the relative axial configuration of a natural biaryl compound on line, by observing long-range ROE interactions. Finally, an oxidative degradation right on the extract delivered the absolute configuration of 4, without isolation of the alkaloid. Ancistrogriffithine A is the as yet only dimeric naphthylisoquinoline from an Asian Ancistrocladaceae plant.

AB - An efficient evaluation procedure for the chemical screening and on-line structural elucidation of dimeric naphthylisoquinoline alkaloids has been developed. The method is based on the lead tetraacetate oxidation of the central binaphthalene core of the alkaloids. UV spectra of the extracts after addition of the oxidant show, in the presence of naphthylisoquinoline dimers, the appearance of a characteristic long-wavelength absorption indicative of dinaphthoquinones. The efficiency and relevance of the method has been demonstrated in the discovery of a constitutionally and configurationally new dimeric naphthylisoquinoline alkaloid, named ancistrogriffithine A (4), from the previously uninvestigated Asian liana Ancistrocladus griffithii. After verification of this screening result by LC−ESI-MS/MS, the constitution and the relative configuration of the compound were elucidated on line, by LC−NMR and LC−CD on the extract. Using an LC−NMR-WET-ROESY experiment, it was possible for the first time to determine the relative axial configuration of a natural biaryl compound on line, by observing long-range ROE interactions. Finally, an oxidative degradation right on the extract delivered the absolute configuration of 4, without isolation of the alkaloid. Ancistrogriffithine A is the as yet only dimeric naphthylisoquinoline from an Asian Ancistrocladaceae plant.

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DO - 10.1021/ac001503q

M3 - Article

VL - 73

SP - 2571

EP - 2577

JO - Analytical Chemistry

JF - Analytical Chemistry

SN - 0003-2700

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ER -