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Pyrrovobasine, hybrid alkylated pyrraline monoterpene indole alkaloid pseudodimer discovered using a combination of mass spectral and NMR-based machine learning annotations.
Fouotsa, Hugues; Mkounga, Pierre; Lannang, Alain Meli; Vanheuverzwijn, Jérôme; Zhou, Zhiyu; Leblanc, Karine; Rharrabti, Somia; Nkengfack, Augustin Ephrem; Gallard, Jean-François; Fontaine, Véronique; Meyer, Franck; Poupon, Erwan; Le Pogam, Pierre; Beniddir, Mehdi A.
Afiliación
  • Fouotsa H; Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Mkounga P; Faculty 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, Belgium.
  • Lannang AM; Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
  • Vanheuverzwijn J; Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
  • Zhou Z; Department of Chemistry, Higher Teachers Training College, University of Maroua, P.O. Box 55, Maroua, Cameroon.
  • Leblanc K; Faculty 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, Belgium.
  • Rharrabti S; Faculty 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, Belgium.
  • Nkengfack AE; Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Gallard JF; Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Fontaine V; Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
  • Meyer F; Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, France.
  • Poupon E; Faculty 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, Belgium.
  • Le Pogam P; Faculty 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, Belgium.
  • Beniddir MA; Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
Org Biomol Chem ; 20(1): 98-105, 2021 12 22.
Article en En | MEDLINE | ID: mdl-34596204
A new vobasine-tryptamine-based monoterpene indole alkaloid pseudodimer was isolated from the stem bark of Voacanga africana. As a minor constituent occurring in a thoroughly investigated plant, this molecule was targeted based on a molecular networking strategy and a rational MS2-guided phytochemical investigation led to its isolation. Its structure was formally established based on HRMS, 1D/2D NMR data, and the application of the tool Small Molecule Accurate Recognition Technology (SMART 2.0). Its absolute configuration was assigned by the exciton chirality method and TD-DFT ECD calculations. Besides featuring an unprecedented intermonomeric linkage in the small group of vobasine/tryptamine hybrids, pyrrovobasine also represents the first pyrraline-containing representative in the whole monoterpene indole alkaloids group. Biosynthetic hypotheses possibly underpinning these structural oddities are proposed here.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirroles / Alcaloides Indólicos / Monoterpenos / Aprendizaje Automático / Norleucina Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Reino Unido
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirroles / Alcaloides Indólicos / Monoterpenos / Aprendizaje Automático / Norleucina Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Reino Unido