Note
Voatriafricanines A and B, Trimeric Vobasine-Aspidosperma-Aspidosperma Alkaloids from Voacanga africanaClick to copy article linkArticle link copied!
- Hugues FouotsaHugues FouotsaÉquipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceDepartment of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, CameroonFaculty of Pharmacy, Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles, Campus de la Plaine-CP 206/04, Boulevard du Triomphe, ACC.2, PO Box 1050, 1050 Bruxelles, BelgiumMore by Hugues Fouotsa
- Pierre Le PogamPierre Le PogamÉquipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceMore by Pierre Le Pogam
- Pierre MkoungaPierre MkoungaDepartment of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, CameroonMore by Pierre Mkounga
- Alain Meli LannangAlain Meli LannangDepartment of Chemistry, Higher Teachers Training College, University of Maroua, P.O. Box 55, Maroua, CameroonMore by Alain Meli Lannang
- Guillaume BernadatGuillaume BernadatÉquipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceMore by Guillaume Bernadat
- Jérôme VanheuverzwijnJérôme VanheuverzwijnFaculty of Pharmacy, Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles, Campus de la Plaine-CP 206/04, Boulevard du Triomphe, ACC.2, PO Box 1050, 1050 Bruxelles, BelgiumMore by Jérôme Vanheuverzwijn
- Zhiyu ZhouZhiyu ZhouFaculty of Pharmacy, Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles, Campus de la Plaine-CP 206/04, Boulevard du Triomphe, ACC.2, PO Box 1050, 1050 Bruxelles, BelgiumMore by Zhiyu Zhou
- Karine LeblancKarine LeblancÉquipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceMore by Karine Leblanc
- Somia RharrabtiSomia RharrabtiÉquipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceMore by Somia Rharrabti
- Augustin Ephrem NkengfackAugustin Ephrem NkengfackDepartment of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, CameroonMore by Augustin Ephrem Nkengfack
- Jean-François GallardJean-François GallardInstitut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, FranceMore by Jean-François Gallard
- Véronique FontaineVéronique FontaineFaculty of Pharmacy, Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles, Campus de la Plaine-CP 206/04, Boulevard du Triomphe, ACC.2, PO Box 1050, 1050 Bruxelles, BelgiumMore by Véronique Fontaine
- Franck MeyerFranck MeyerFaculty of Pharmacy, Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles, Campus de la Plaine-CP 206/04, Boulevard du Triomphe, ACC.2, PO Box 1050, 1050 Bruxelles, BelgiumMore by Franck Meyer
- Erwan PouponErwan PouponÉquipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceMore by Erwan Poupon
- Mehdi A. Beniddir*Mehdi A. Beniddir*Tel: 33 1 46 83 55 87. Fax: +33 1 46 83 53 99. E-mail: [email protected]Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, FranceMore by Mehdi A. Beniddir
Abstract
Click to copy section linkSection link copied!
Voatriafricanines A and B (1 and 2), the first examples of vobasine-aspidosperma-aspidosperma monoterpene trisindole alkaloids, were isolated from the stem barks of Voacanga africana, guided by a molecular networking strategy. Their structures, including absolute configurations, were elucidated by spectroscopic methods and ECD calculations. Compounds 1 and 2 possess intramolecular hydrogen bonding, sufficiently robust to transfer homonuclear and heteronuclear magnetizations. Compound 1 exhibited potent antimycobacterial activity with no discernible cytotoxic activity.
Copyright © 2021 American Chemical Society and American Society of Pharmacognosy
Cited By
Click to copy section linkSection link copied!
Citation Statements
beta
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
Explore this article's citation statements on scite.ai
This article is cited by 11 publications.
- Sarah Szwarc, Adrien Jagora, Séverine Derbré, Karine Leblanc, Somia Rharrabti, Charifat Said-Hassane, Chaker El Kalamouni, Jean-François Gallard, Pierre Le Pogam, Mehdi A. Beniddir. Combination of Machine Learning and Empirical Computation for the Structural Validation of Trirosaline, a Natural Trimeric Monoterpene Indole Alkaloid from Catharanthus roseus. Organic Letters 2024, 26
(1)
, 274-279. https://doi.org/10.1021/acs.orglett.3c03972
- Jakob K. Reinhardt, David Craft, Jing-Ke Weng. Toward an integrated omics approach for plant biosynthetic pathway discovery in the age of AI. Trends in Biochemical Sciences 2025, 50
(4)
, 311-321. https://doi.org/10.1016/j.tibs.2025.01.010
- Cai-Feng Ding, Ma-Long Qin, Kun-Ying Zhao, Wen Gao, Shan-Ze Yin, Xian-Guang Hu, Gui-Guang Cheng, Rong-Ping Zhang, Wei-Yan Hu. Voagafries A–E, undescribed indole alkaloids with anti-glioma activity from Voacanga africana. Phytochemistry 2025, 231 , 114361. https://doi.org/10.1016/j.phytochem.2024.114361
- Pierre Le Pogam, Mehdi A. Beniddir. Structural diversity and chemical logic underlying the assembly of monoterpene indole alkaloids oligomers. Natural Product Reports 2024, 41
(11)
, 1723-1765. https://doi.org/10.1039/D4NP00011K
- Malong Qin, Wen Gao, Haiyin Wang, Shanze Yin, Jianlin Hu, Weimin Gao, Caifeng Ding. Monoterpenoid indole alkaloids from the stem barks of Voacanga africana and their chemotaxonomic significance. Biochemical Systematics and Ecology 2024, 116 , 104863. https://doi.org/10.1016/j.bse.2024.104863
- Christian Bailly. Traditional Uses, Pharmacology and Phytochemistry of the Medicinal Plant Flueggea virosa (Roxb. ex Willd.) Royle. Future Pharmacology 2024, 4
(1)
, 77-102. https://doi.org/10.3390/futurepharmacol4010007
- Yang Yu, Jing Wu, Mei-Fen Bao, Johann Schinnerl, Xiang-Hai Cai. Diverse aspidosperma-type alkaloids from the leaves of Tabernaemontana bovina with anti-hepatoma activity. Fitoterapia 2023, 169 , 105588. https://doi.org/10.1016/j.fitote.2023.105588
- Mehdi A. Beniddir, Ulf Göransson, Luke P. Robertson. On the structures of the penduflorines from Tabernaemontana penduliflora. Fitoterapia 2023, 167 , 105506. https://doi.org/10.1016/j.fitote.2023.105506
- Salemon Akpa Agnès, Timothée Okpekon, Yvette Affoué Kouadio, Adrien Jagora, Dimitri Bréard, Emmanoel V. Costa, Felipe M. A. da Silva, Hector H. F. Koolen, Anne-Marie Le Ray-Richomme, Pascal Richomme, Pierre Champy, Mehdi A. Beniddir, Pierre Le Pogam. Implementation of a MS/MS database for isoquinoline alkaloids and other annonaceous metabolites. Scientific Data 2022, 9
(1)
https://doi.org/10.1038/s41597-022-01345-y
- Syed Muhammad Umer, Mehwish Solangi, Khalid Mohammed Khan, Rahman Shah Zaib Saleem. Indole-Containing Natural Products 2019–2022: Isolations, Reappraisals, Syntheses, and Biological Activities. Molecules 2022, 27
(21)
, 7586. https://doi.org/10.3390/molecules27217586
- Olivier Bonnet, Mehdi A. Beniddir, Pierre Champy, Védaste Kagisha, Alain Nyirimigabo, Carla Hamann, Giorgi Jgerenaia, Allison Ledoux, Alembert Tiabou Tchinda, Luc Angenot, Michel Frédérich. Exploration by molecular networking of Strychnos alkaloids reveals the unexpected occurrence of strychnine in seven Strychnos species. Toxicon 2022, 215 , 57-68. https://doi.org/10.1016/j.toxicon.2022.06.002
Learn about these metrics
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.