دورية أكاديمية
Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata
| العنوان: | Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata |
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| المؤلفون: | Florian Traxler, Haoqi Zhang, Wiratchanee Mahavorasirikul, Katharina Krivanek, Xiang-Hai Cai, Wichai Aiyakool, Martin Pfeiffer, Lothar Brecker, Johann Schinnerl |
| المصدر: | Molecules, Vol 28, Iss 18, p 6664 (2023) |
| بيانات النشر: | MDPI AG, 2023. |
| سنة النشر: | 2023 |
| المجموعة: | LCC:Organic chemistry |
| مصطلحات موضوعية: | Apocynaceae, Tabernaemontana peduncularis, Tabernaemontana divaricata, javaniside, indole alkaloid, glucuronide alkaloid, Organic chemistry, QD241-441 |
| الوصف: | Phytochemical investigation of the two Tabernaemontana species (Apocynaceae) T. peduncularis Wall. and T. divaricata (L.) R.Br. ex Roem. & Schult. indicated closely related biosynthetic pathways leading to lipophilic and hydrophilic alkaloids. In total, 18 specialized metabolites comprising indole-derived alkaloid aglycones, three oxindole-derived alkaloid glycosides, and two iridoid glucosides could be identified in the studied species. Among the alkaloids, the two Iboga-type alkaloids 3,7-coronaridine isoindolenine, coronaridine 3,4-iminium and a javaniside derivative bearing a glucuronic acid, named javanuronic acid, could be described by spectroscopic and spectrometric methods for the first time. A docking experiment using alpha-fold was performed to generate a protein model of the enzyme 7-deoxyloganetic acid glucosyl transferase. Performed bioassays exhibited a growth reduction of neonate Spodoptera littoralis larvae and reduced cell viability of HepG2 cells of the extracts containing Iboga alkaloids, whilst the javaniside derivatives containing hydrophilic fraction did not show any effects. These findings indicate a high flexibility in the formation of bioactive indole alkaloid aglycones by Tabernaemontana species and also evidence similar accumulation trends in both species as well as indicate that biosynthetic routes leading to oxindole alkaloids like javanisides are more widespread than reported. Furthermore, the incorporation of the three novel compounds into potential biosynthetic pathways is discussed. |
| نوع الوثيقة: | article |
| وصف الملف: | electronic resource |
| اللغة: | English |
| تدمد: | 28186664 1420-3049 |
| Relation: | https://www.mdpi.com/1420-3049/28/18/6664; https://doaj.org/toc/1420-3049 |
| DOI: | 10.3390/molecules28186664 |
| URL الوصول: | https://doaj.org/article/aee247d3a2db40e880596c312c67db61 |
| رقم الأكسشن: | edsdoj.247d3a2db40e880596c312c67db61 |
| قاعدة البيانات: | Directory of Open Access Journals |
Full Text Finder | تدمد: | 28186664 14203049 |
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| DOI: | 10.3390/molecules28186664 |