Isolation and NMR Scaling Factors for the Structure Determination of Lobatolide H, a Flexible Sesquiterpene from Neurolaena lobata
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- Tibor Kovács
- Department of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, Hungary
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- Ildikó Lajter
- Institute of Pharmacognosy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Norbert Kúsz
- Institute of Pharmacognosy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Zsuzsanna Schelz
- Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Noémi Bózsity-Faragó
- Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Anikó Borbás
- Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary
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- István Zupkó
- Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Georg Krupitza
- Department of Pathology, Medical University of Vienna, Waehringer Guertel 18-20, 1090 Vienna, Austria
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- Richard Frisch
- Institute for Ethnobiology, Playa Diana, San José GT-170, Guatemala
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- Judit Hohmann
- Institute of Pharmacognosy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Andrea Vasas
- Institute of Pharmacognosy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
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- Attila Mándi
- Department of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, Hungary
抄録
<jats:p>A new flexible germacranolide (1, lobatolide H) was isolated from the aerial parts of Neurolaena lobata. The structure elucidation was performed by classical NMR experiments and DFT NMR calculations. Altogether, 80 theoretical level combinations with existing 13C NMR scaling factors were tested, and the best performing ones were applied on 1. 1H and 13C NMR scaling factors were also developed for two combinations utilizing known exomethylene containing derivatives, and the results were complemented by homonuclear coupling constant (JHH) and TDDFT-ECD calculations to elucidate the stereochemistry of 1. Lobatolide H possessed remarkable antiproliferative activity against human cervical tumor cell lines with different HPV status (SiHa and C33A), induced cell cycle disturbance and exhibited a substantial antimigratory effect in SiHa cells.</jats:p>
収録刊行物
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- International Journal of Molecular Sciences
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International Journal of Molecular Sciences 24 (6), 5841-, 2023-03-19
MDPI AG