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Ancistrobrevinium A, the first N-methylated, cationic naphthylisoquinoline alkaloid, from the tropical liana Ancistrocladus abbreviatus (Ancistrocladaceae).
Tajuddeen, Nasir; Fayez, Shaimaa; Kushwaha, Prem Prakash; Feineis, Doris; Aké Assi, Laurent; Kumar, Shashank; Bringmann, Gerhard.
Afiliación
  • Tajuddeen N; Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria.
  • Fayez S; Institute of Organic Chemistry, University of Würzburg, Würzburg, Germany.
  • Kushwaha PP; Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo, Egypt.
  • Feineis D; Molecular Signaling & Drug Discovery Laboratory, Department of Biochemistry, Central University of Punjab, Punjab, India.
  • Aké Assi L; Institute of Organic Chemistry, University of Würzburg, Würzburg, Germany.
  • Kumar S; Centre National de Floristique, Université d'Abidjan, Conservatoire et Jardin Botanique, Ivory Coast.
  • Bringmann G; Molecular Signaling & Drug Discovery Laboratory, Department of Biochemistry, Central University of Punjab, Punjab, India.
Nat Prod Res ; : 1-5, 2023 Mar 29.
Article en En | MEDLINE | ID: mdl-36987744
Ancistrobrevinium A (1) is the first N-methylated and non-hydrogenated, and thus cationic naphthylisoquinoline alkaloid. It was discovered in the root bark extract of the phytochemically productive West African liana Ancistrocladus abbreviatus (Ancistrocladaceae). Its constitution was elucidated by HR-ESI-MS and 1D and 2D NMR. Due to the steric hindrance in the proximity of the linkage between the naphthalene and isoquinoline parts, the biaryl axis is rotationally hindered. It thus constitutes a stable element of chirality - the only one in the new alkaloid since, different from most other naphthylisoquinoline alkaloids, it has no stereogenic centers. The axial configuration of 1 was assigned by electronic circular dichroism (ECD) investigations, which gave a positive couplet, indicating a 'positive chirality', here corresponding to a P-configuration. Ancistrobrevinium A (1) showed a weak cytotoxic activity against A549 lung cancer cells (IC50 = 50.6 µM).
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Nat Prod Res Año: 2023 Tipo del documento: Article País de afiliación: Nigeria Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Nat Prod Res Año: 2023 Tipo del documento: Article País de afiliación: Nigeria Pais de publicación: Reino Unido