Extract screening by HPLC coupled to MS-MS, NMR, and CD: A dimeric and three monomeric naphthylisoquinoline alkaloids from Ancistrocladus griffithii

G. Bringmann (Corresponding Author), M. Wohlfarth, Heiko Rischer, J. Schlauer, R. Brun

Research output: Contribution to journalArticleScientificpeer-review

50 Citations (Scopus)

Abstract

Three new monomeric naphthylisoquinoline alkaloids, ancistrogriffines A, B, and C, and the first dimer of a 7,8'-coupled naphthylisoquinoline, ancistrogriffithine A, have been detected by phytochemical online screening of plant extracts of Ancistrocladus griffithii, using the analytical 'triad' HPLC-MS/MS, HPLC-NMR, and HPLC-CD. Ancistrogriffithine A, as well as ancistrogriffines A and C, were structurally completely assigned (including the absolute configuration) right from the extract, without previous isolation. Furthermore, two related, but known alkaloids, ancistrocladine and hamatine, were identified. Except for ancistrogriffine B, which occurs in trace quantities only, all new alkaloids were then isolated preparatively and the initial assignments were fully confirmed by conventional offline methods. Of particular interest is the constitutionally and configurationally unprecedented structure of ancistrogriffithine A, which is simultaneously the first dimeric naphthylisoquinoline alkaloid from an Asian Ancistrocladus species. Ancistrogriffithine A and ancistrogriffine A are active against Plasmodium falciparum. Furthermore, the latter compound shows good activity against Leishmania donovani. The results demonstrate the ability of modern online methods like HPLC-NMR, -MS/MS, and -CD to serve as powerful tools for the reliable structural elucidation of even complex structures of trace compounds in crude biological matrices.
Original languageEnglish
Pages (from-to)195-204
JournalPhytochemistry
Volume61
Issue number2
DOIs
Publication statusPublished - 2002
MoE publication typeA1 Journal article-refereed

Fingerprint

Alkaloids
alkaloids
Screening
High Pressure Liquid Chromatography
Nuclear magnetic resonance
screening
extracts
Leishmania donovani
Plant Extracts
Plasmodium falciparum
Phytochemicals
plant extracts
Dimers
phytopharmaceuticals
tandem mass spectrometry
methodology

Keywords

  • Ancistrocladus griffithii; Ancistrocladaceae; Ancistrogriffithine A; Ancistrogriffine A; Ancistrogriffine B; Ancistrogriffine C; Hyphenated analysis; Online structure eludication; Isolation; Antimalarial activity

Cite this

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title = "Extract screening by HPLC coupled to MS-MS, NMR, and CD: A dimeric and three monomeric naphthylisoquinoline alkaloids from Ancistrocladus griffithii",
abstract = "Three new monomeric naphthylisoquinoline alkaloids, ancistrogriffines A, B, and C, and the first dimer of a 7,8'-coupled naphthylisoquinoline, ancistrogriffithine A, have been detected by phytochemical online screening of plant extracts of Ancistrocladus griffithii, using the analytical 'triad' HPLC-MS/MS, HPLC-NMR, and HPLC-CD. Ancistrogriffithine A, as well as ancistrogriffines A and C, were structurally completely assigned (including the absolute configuration) right from the extract, without previous isolation. Furthermore, two related, but known alkaloids, ancistrocladine and hamatine, were identified. Except for ancistrogriffine B, which occurs in trace quantities only, all new alkaloids were then isolated preparatively and the initial assignments were fully confirmed by conventional offline methods. Of particular interest is the constitutionally and configurationally unprecedented structure of ancistrogriffithine A, which is simultaneously the first dimeric naphthylisoquinoline alkaloid from an Asian Ancistrocladus species. Ancistrogriffithine A and ancistrogriffine A are active against Plasmodium falciparum. Furthermore, the latter compound shows good activity against Leishmania donovani. The results demonstrate the ability of modern online methods like HPLC-NMR, -MS/MS, and -CD to serve as powerful tools for the reliable structural elucidation of even complex structures of trace compounds in crude biological matrices.",
keywords = "Ancistrocladus griffithii; Ancistrocladaceae; Ancistrogriffithine A; Ancistrogriffine A; Ancistrogriffine B; Ancistrogriffine C; Hyphenated analysis; Online structure eludication; Isolation; Antimalarial activity",
author = "G. Bringmann and M. Wohlfarth and Heiko Rischer and J. Schlauer and R. Brun",
year = "2002",
doi = "10.1016/S0031-9422(02)00217-0",
language = "English",
volume = "61",
pages = "195--204",
journal = "Phytochemistry",
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Extract screening by HPLC coupled to MS-MS, NMR, and CD : A dimeric and three monomeric naphthylisoquinoline alkaloids from Ancistrocladus griffithii. / Bringmann, G. (Corresponding Author); Wohlfarth, M.; Rischer, Heiko; Schlauer, J.; Brun, R.

In: Phytochemistry, Vol. 61, No. 2, 2002, p. 195-204.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Extract screening by HPLC coupled to MS-MS, NMR, and CD

T2 - A dimeric and three monomeric naphthylisoquinoline alkaloids from Ancistrocladus griffithii

AU - Bringmann, G.

AU - Wohlfarth, M.

AU - Rischer, Heiko

AU - Schlauer, J.

AU - Brun, R.

PY - 2002

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N2 - Three new monomeric naphthylisoquinoline alkaloids, ancistrogriffines A, B, and C, and the first dimer of a 7,8'-coupled naphthylisoquinoline, ancistrogriffithine A, have been detected by phytochemical online screening of plant extracts of Ancistrocladus griffithii, using the analytical 'triad' HPLC-MS/MS, HPLC-NMR, and HPLC-CD. Ancistrogriffithine A, as well as ancistrogriffines A and C, were structurally completely assigned (including the absolute configuration) right from the extract, without previous isolation. Furthermore, two related, but known alkaloids, ancistrocladine and hamatine, were identified. Except for ancistrogriffine B, which occurs in trace quantities only, all new alkaloids were then isolated preparatively and the initial assignments were fully confirmed by conventional offline methods. Of particular interest is the constitutionally and configurationally unprecedented structure of ancistrogriffithine A, which is simultaneously the first dimeric naphthylisoquinoline alkaloid from an Asian Ancistrocladus species. Ancistrogriffithine A and ancistrogriffine A are active against Plasmodium falciparum. Furthermore, the latter compound shows good activity against Leishmania donovani. The results demonstrate the ability of modern online methods like HPLC-NMR, -MS/MS, and -CD to serve as powerful tools for the reliable structural elucidation of even complex structures of trace compounds in crude biological matrices.

AB - Three new monomeric naphthylisoquinoline alkaloids, ancistrogriffines A, B, and C, and the first dimer of a 7,8'-coupled naphthylisoquinoline, ancistrogriffithine A, have been detected by phytochemical online screening of plant extracts of Ancistrocladus griffithii, using the analytical 'triad' HPLC-MS/MS, HPLC-NMR, and HPLC-CD. Ancistrogriffithine A, as well as ancistrogriffines A and C, were structurally completely assigned (including the absolute configuration) right from the extract, without previous isolation. Furthermore, two related, but known alkaloids, ancistrocladine and hamatine, were identified. Except for ancistrogriffine B, which occurs in trace quantities only, all new alkaloids were then isolated preparatively and the initial assignments were fully confirmed by conventional offline methods. Of particular interest is the constitutionally and configurationally unprecedented structure of ancistrogriffithine A, which is simultaneously the first dimeric naphthylisoquinoline alkaloid from an Asian Ancistrocladus species. Ancistrogriffithine A and ancistrogriffine A are active against Plasmodium falciparum. Furthermore, the latter compound shows good activity against Leishmania donovani. The results demonstrate the ability of modern online methods like HPLC-NMR, -MS/MS, and -CD to serve as powerful tools for the reliable structural elucidation of even complex structures of trace compounds in crude biological matrices.

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DO - 10.1016/S0031-9422(02)00217-0

M3 - Article

VL - 61

SP - 195

EP - 204

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 2

ER -