Tan, Yi-Sheng and Ng, Min-Phin and Tan, Chun-Hoe and Tang, Wai-Kit and Sim, Kae-Shin and Yong, Kien-Thai and Krishnan, Premanand and Lim, Kuan-Hon and Lim, Siew-Huah and Low, Yun-Yee (2024) Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia. Journal of Natural Products, 87 (2). pp. 286-296. ISSN 0163-3864, DOI https://doi.org/10.1021/acs.jnatprod.3c00960.
Full text not available from this repository.Abstract
Nine new alkaloids, eugeniinalines A-H (1-8) and (+)-eburnamenine N-oxide (9), comprising one quinoline, six indole, and two isogranatanine alkaloids, were isolated from the stem-bark extract of the Malayan Leuconotis eugeniifolia. The structures and absolute configurations of these alkaloids were established based on the analysis of the spectroscopic data, GIAO NMR calculations, DP4+ probability analysis, TDDFT-ECD method, and X-ray diffraction analysis. Eugeniinaline A (1) represents a new pentacyclic quinoline alkaloid with a 6/6/5/6/7 ring system. Eugeniinaline G (7) and its seco-derivative, eugeniinaline H (8), were the first isogranatanine alkaloids isolated as natural products. The known alkaloids leucolusine (10) and melokhanine A (11) were found to be the same compound, based on comparison of the spectroscopic data of both compounds, with the absolute configuration of (7R, 20R, 21S). Eugeniinalines A and G (1 and 7) showed cytotoxic activity against the HT-29 cancer cell line with IC50 values of 7.1 and 7.2 mu M, respectively.
| Item Type: | Article |
|---|---|
| Funders: | Ministry of Education, Malaysia (FRGS/1/2023/STG04/UM/02/13), Ministry of Higher Education (MOHE) Malaysia, Universiti Malaya |
| Uncontrolled Keywords: | Bisindole Alkaloids; Secoleuconoxine; Sarpagine; Revision; Eburnan; H-1 |
| Subjects: | Q Science > QD Chemistry R Medicine > RM Therapeutics. Pharmacology R Medicine > RS Pharmacy and materia medica S Agriculture > SB Plant culture |
| Divisions: | Faculty of Science > Institute of Biological Sciences Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 11 Nov 2024 04:16 |
| Last Modified: | 11 Nov 2024 04:16 |
| URI: | http://eprints.um.edu.my/id/eprint/45735 |
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