Lim, Kuan-Hon and Mai, Chun-Wai and Wong, Soon Kit and Low, Yun Yee and Lim, Siew-Huah and Krishnan, Premanand (2024) Yunnanensine type indole and seco stemmadenine-yunnanensine type bisindole alkaloids from the bark of Alstonia scholaris. Phytochemistry Letters, 61. pp. 97-103. ISSN 1874-3900, DOI https://doi.org/10.1016/j.phytol.2024.04.003.
Full text not available from this repository.Abstract
Two previously undescribed monoterpenoid indole alkaloids, N -formylyunnanensine ( 1 ) and scholaphylline ( 2 ), along with eight known alkaloids, namely, 19,20- E -vallesamine ( 3 ), 19,20- Z -vallesamine ( 4 ), 19,20- E -valles- amine N -oxide ( 5 ), 6,7- seco -19,20 alpha-epoxyangustilobine B ( 6 ), 16 R -19,20- E -isositsirikine ( 7 ), N -demethylal- stogustine N -oxide ( 8 ), E -vallesiachotamine ( 9 ), and Z -vallesiachotamine ( 10 ), were isolated from the bark of Alstonia scholaris. Alkaloid 1 was determined to be the N -formyl derivative of the known alkaloid, yunnanensine, comprising a pair of inseparable E / Z -formamide rotamers, while scholaphylline ( 2 ) was identified as the first member of the seco stemmadenine-yunnanensine type bisindole alkaloid. The structures of these alkaloids and their absolute configurations were established based on detailed analysis of the spectroscopic data in conjunction with the TDDFT-ECD method. A possible biogenetic pathway to 1 and 2 , involving stemmadenine as the primary precursor, was proposed. Scholaphylline ( 2 ) showed modest cytotoxicity against Panc1 (IC 50 27.7 +/- 5.1 mu M), MDA-MB-231 (IC 50 32.0 +/- 2.2 mu M), and MDA-MB-468 (IC 50 34.1 +/- 3.3 mu M) cancer cell lines, while N -for- mylyunnanensine ( 1 ) did not show appreciable cytotoxicity against any of the tested cell lines.
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Uncontrolled Keywords: | Alstonia scholaris; Apocynaceae; Alkaloids; Bisindole; Rotamers |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 25 Sep 2024 07:54 |
| Last Modified: | 25 Sep 2024 07:54 |
| URI: | http://eprints.um.edu.my/id/eprint/45186 |
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