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Structure Revision of the Sesquiterpene Nordine Based on NMR Spectroscopic Analysis and X-ray Crystallography.
de Andrade, Rodrigo Silva; Sales, Kaio Aragão; Abreu, Lucas Silva; Campos, Vinícius Rangel; Dos Santos Junior, Fernando Martins; Braz-Filho, Raimundo; Scotti, Marcus Tullius; Tavares, Josean Fechine; da Silva, Marcelo Sobral.
Afiliación
  • de Andrade RS; Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraiba, João Pessoa 58051-900, Brazil.
  • Sales KA; Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraiba, João Pessoa 58051-900, Brazil.
  • Abreu LS; Department of Organic Chemistry, Institute of Chemistry, Fluminense Federal University, Rio de Janeiro 24020-141, Brazil.
  • Campos VR; Department of Organic Chemistry, Institute of Chemistry, Fluminense Federal University, Rio de Janeiro 24020-141, Brazil.
  • Dos Santos Junior FM; Department of Organic Chemistry, Institute of Chemistry, Fluminense Federal University, Rio de Janeiro 24020-141, Brazil.
  • Braz-Filho R; Department of Chemistry, Institute of Chemistry, Federal Rural University of Rio de Janeiro, Seropédica 23890-000, Brazil.
  • Scotti MT; Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraiba, João Pessoa 58051-900, Brazil.
  • Tavares JF; Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraiba, João Pessoa 58051-900, Brazil.
  • da Silva MS; Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraiba, João Pessoa 58051-900, Brazil.
J Nat Prod ; 85(10): 2480-2483, 2022 10 28.
Article en En | MEDLINE | ID: mdl-36254387
Nordine was reported to be an unusual humulene-type macrocyclic sesquiterpenoid that contains an ether-bridged bicyclic ring between C-10 and C-6 with a hydroxy group at position 2. Here, we report the structure revision of nordine based on incongruities found for carbon chemical shifts in the originally proposed structure, in addition to formation of a diacetylated derivative. As expected, a single-crystal X-ray diffraction analysis unambiguously confirmed our proposal that the nordine (1) structure contains an ether-bridged bicyclic ring between C-10 and C-7 and hydroxy groups at C-2 and C-6. Furthermore, the absolute configuration was determined by ECD spectroscopic analysis.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sesquiterpenos Idioma: En Revista: J Nat Prod Año: 2022 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sesquiterpenos Idioma: En Revista: J Nat Prod Año: 2022 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos