2. Academic Validation
  3. Herpotrichones A and B, Two Intermolecular [4 + 2] Adducts with Anti-Neuroinflammatory Activity from a Herpotrichia Species

Herpotrichones A and B, Two Intermolecular [4 + 2] Adducts with Anti-Neuroinflammatory Activity from a Herpotrichia Species

  • Org Lett. 2020 Jan 17;22(2):405-409. doi: 10.1021/acs.orglett.9b04099.
Wen-Bo Han 1,  Guang-Yi Wang 1,  Jiang-Jiang Tang 1,  Wen-Ji Wang 1,  Han Liu 2,  Roberto R Gil 3,  Armando Navarro-Vázquez 4,  Xinxiang Lei 2,  Jin-Ming Gao 1
Affiliations

Affiliations

  • 1 Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry and Pharmacy , Northwest A&F University , Yangling , Shaanxi 712100 , People's Republic of China.
  • 2 School of Pharmaceutical Sciences , South Central University for Nationalities , Wuhan , Hubei 430074 , People's Republic of China.
  • 3 Department of Chemistry , Carnegie Mellon University , 4400 Fifth Avenue , Pittsburgh , Pennsylvania 15213 , United States.
  • 4 Departamento de Química Fundamental , Universidade Federal de Pernambuco , Avenida Professor Moraes Rego, 1235, Cidade Universitária , Recife , Pernambuco 50670-901 , Brazil.
PMID: 31874039 DOI: 10.1021/acs.orglett.9b04099
Abstract

Herpotrichones A and B (1 and 2), two intermolecular [4 + 2] adducts with an unprecedented pentacyclic 6/6/6/6/3 skeleton, were isolated from Herpotrichia sp. SF09, an isopod-associated fungus, along with a new shunt product protrichone (3). Their structures were elucidated by the analysis of spectroscopic data, residual dipolar coupling (RDC)-based computer-assisted 3D structure elucidation (CASE-3D), and single-crystal X-ray diffraction in combination with electronic circular dichroism (ECD) calculations. Compounds 1 and 2 were assessed to be potent anti-neuroinflammatory agents in lipopolysaccharide (LPS)-induced BV-2 microglial cells with the half maximal inhibitory concentration (IC50) values of 0.41 and 0.11 μM, respectively.

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