Tang, Sin-Yee and Ng, Min-Phin and Tan, Chun-Hoe and Sim, Kae-Shin and Lim, Kuan-Hon and Yong, Kien-Thai and Low, Yun-Yee and Lim, Siew-Huah (2023) Chippiine, iboga, cleavamine, vobasine, and cytotoxic bisindole alkaloids from Tabernaemontana polyneura. Tetrahedron, 149. ISSN 0040-4020, DOI https://doi.org/10.1016/j.tet.2023.133706.
Full text not available from this repository.Abstract
Eight undescribed indole alkaloids, polyneurines I-P (1-8), comprising one chippiine, two iboga, one cleavamine, three vobasine, and one vobasinyl-iboga bisindole alkaloid, were isolated from the bark of Tabernaemontana polyneura. The structures of these undescribed alkaloids were established by interpretation of the MS and NMR data, while the configurations were determined using GIAO NMR calculations and DP4+ probability analysis, and TDDFT-ECD method. Polyneurines I (1) and J (2) are characterized by the presence of an additional pyrrolidine ring incorporated within the chippiine or seco-coronaridine skeletal framework. Biosynthetic pathways towards the formation of polyneurines I (1) and J (2) are proposed. Polyneurine P (8), along with four known bisindoles, showed appreciable cytotoxicity against HT-29, HCT 116, MDA-MB-231, and A549 cancer cell lines with IC50 values ranging between 0.3 and 9.0 mu M. The variation in alkaloidal content observed between the present and previous study, both involving the same plant species but occurring at different locations, is also discussed.
| Item Type: | Article |
|---|---|
| Funders: | Ministry of Higher Education (MOHE) Malaysia [Grant No: FRGS/1/2023/STG04/UM/02/13], Universiti Malaya |
| Uncontrolled Keywords: | Tabernaemontana polyneura; Apocynaceae; Indole and bisindole alkaloids; ECD; Cytotoxicity |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Institute of Biological Sciences Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 03 Nov 2025 02:28 |
| Last Modified: | 03 Nov 2025 02:28 |
| URI: | http://eprints.um.edu.my/id/eprint/48597 |
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