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Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.
Qin, Xu-Jie; Rauwolf, Tyler J; Li, Pan-Pan; Liu, Hui; McNeely, James; Hua, Yan; Liu, Hai-Yang; Porco, John A.
Afiliação
  • Qin XJ; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, P. R. China.
  • Rauwolf TJ; Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University, 590 Commonwealth Avenue, Boston, MA, 02215, USA.
  • Li PP; College of Forestry, Southwest Forestry University, Kunming, 650224, P. R. China.
  • Liu H; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, P. R. China.
  • McNeely J; Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University, 590 Commonwealth Avenue, Boston, MA, 02215, USA.
  • Hua Y; College of Forestry, Southwest Forestry University, Kunming, 650224, P. R. China.
  • Liu HY; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, P. R. China.
  • Porco JA; Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University, 590 Commonwealth Avenue, Boston, MA, 02215, USA.
Angew Chem Int Ed Engl ; 58(13): 4291-4296, 2019 03 22.
Article em En | MEDLINE | ID: mdl-30681258
ABSTRACT
Rhodomyrtusials A-C, the first examples of triketone-sesquiterpene meroterpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus tomentosa, along with several biogenetically-related dihydropyran isomers. Two bis-furans and one dihydropyran isomer showed acetylcholinesterase (AChE) inhibitory activity. Structures of the isolates were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Bioinspired total syntheses of six isolates were achieved in six steps utilizing a reactive enetrione intermediate generated in situ from a readily available hydroxy-endoperoxide precursor.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Acetilcolinesterase / Sesquiterpenos / Terpenos / Extratos Vegetais / Myrtaceae Limite: Humans Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2019 Tipo de documento: Article
Texto completo
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XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Acetilcolinesterase / Sesquiterpenos / Terpenos / Extratos Vegetais / Myrtaceae Limite: Humans Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2019 Tipo de documento: Article