Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i>
Phytochemical investigation of the two <i>Tabernaemontana</i> species (Apocynaceae) <i>T</i>. <i>peduncularis</i> Wall. and <i>T</i>. <i>divaricata</i> (L.) R.Br. ex Roem. & Schult. indicated closely related biosynthetic pathways leadin...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/18/6664 |
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| author | Florian Traxler Haoqi Zhang Wiratchanee Mahavorasirikul Katharina Krivanek Xiang-Hai Cai Wichai Aiyakool Martin Pfeiffer Lothar Brecker Johann Schinnerl |
| author_facet | Florian Traxler Haoqi Zhang Wiratchanee Mahavorasirikul Katharina Krivanek Xiang-Hai Cai Wichai Aiyakool Martin Pfeiffer Lothar Brecker Johann Schinnerl |
| author_sort | Florian Traxler |
| collection | DOAJ |
| description | Phytochemical investigation of the two <i>Tabernaemontana</i> species (Apocynaceae) <i>T</i>. <i>peduncularis</i> Wall. and <i>T</i>. <i>divaricata</i> (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 <i>Iboga</i>-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 <i>Spodoptera littoralis</i> larvae and reduced cell viability of HepG2 cells of the extracts containing <i>Iboga</i> 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 <i>Tabernaemontana</i> 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. |
| first_indexed | 2024-03-10T22:24:27Z |
| format | Article |
| id | doaj.art-aee247d3a2db40e880596c312c67db61 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T22:24:27Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-aee247d3a2db40e880596c312c67db612023-11-19T12:10:40ZengMDPI AGMolecules1420-30492023-09-012818666410.3390/molecules28186664Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i>Florian Traxler0Haoqi Zhang1Wiratchanee Mahavorasirikul2Katharina Krivanek3Xiang-Hai Cai4Wichai Aiyakool5Martin Pfeiffer6Lothar Brecker7Johann Schinnerl8Department of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, AustriaDepartment of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, AustriaDrug Discovery and Development Center, Advanced Science and Technologies, Thammasat University (Rangsit Campus), Pathumthani 12121, ThailandDepartment of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, AustriaState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, ChinaDepartment of Botany, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandInstitute of Biotechnology and Biochemical Engineering, Graz University of Technology, A-8010 Graz, AustriaDepartment of Organic Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, AustriaDepartment of Botany and Biodiversity Research, University of Vienna, Rennweg 14, A-1030 Vienna, AustriaPhytochemical investigation of the two <i>Tabernaemontana</i> species (Apocynaceae) <i>T</i>. <i>peduncularis</i> Wall. and <i>T</i>. <i>divaricata</i> (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 <i>Iboga</i>-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 <i>Spodoptera littoralis</i> larvae and reduced cell viability of HepG2 cells of the extracts containing <i>Iboga</i> 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 <i>Tabernaemontana</i> 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.https://www.mdpi.com/1420-3049/28/18/6664Apocynaceae<i>Tabernaemontana peduncularis</i><i>Tabernaemontana divaricata</i>javanisideindole alkaloidglucuronide alkaloid |
| spellingShingle | Florian Traxler Haoqi Zhang Wiratchanee Mahavorasirikul Katharina Krivanek Xiang-Hai Cai Wichai Aiyakool Martin Pfeiffer Lothar Brecker Johann Schinnerl Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i> Molecules Apocynaceae <i>Tabernaemontana peduncularis</i> <i>Tabernaemontana divaricata</i> javaniside indole alkaloid glucuronide alkaloid |
| title | Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i> |
| title_full | Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i> |
| title_fullStr | Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i> |
| title_full_unstemmed | Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i> |
| title_short | Two Novel <i>Iboga</i>-Type and an Oxindole Glucuronide Alkaloid from <i>Tabernaemontana peduncularis</i> Disclose Related Biosynthetic Pathways to <i>Tabernaemontana divaricata</i> |
| title_sort | two novel i iboga i type and an oxindole glucuronide alkaloid from i tabernaemontana peduncularis i disclose related biosynthetic pathways to i tabernaemontana divaricata i |
| topic | Apocynaceae <i>Tabernaemontana peduncularis</i> <i>Tabernaemontana divaricata</i> javaniside indole alkaloid glucuronide alkaloid |
| url | https://www.mdpi.com/1420-3049/28/18/6664 |
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