2. Academic Validation
  3. NMR-Based Investigation of Hydrogen Bonding in a Dihydroanthracen-1(4 H)one from Rubia philippinensis and Its Soluble Epoxide Hydrolase Inhibitory Potential

NMR-Based Investigation of Hydrogen Bonding in a Dihydroanthracen-1(4 H)one from Rubia philippinensis and Its Soluble Epoxide Hydrolase Inhibitory Potential

  • J Nat Prod. 2018 Nov 26;81(11):2429-2435. doi: 10.1021/acs.jnatprod.8b00441.
Joonseok Oh 1 2,  Khong Trong Quan 3 4,  Ji Sun Lee 3,  InWha Park 3,  Chung Sub Kim 1 2,  Daneel Ferreira 5,  Phuong Thien Thuong 4,  Young Ho Kim 3,  MinKyun Na 3
Affiliations

Affiliations

  • 1 Department of Chemistry , Yale University , New Haven , Connecticut 06520 , United States.
  • 2 Chemical Biology Institute , Yale University , West Haven , Connecticut 06516 , United States.
  • 3 College of Pharmacy , Chungnam National University , Daejeon 34134 , Republic of Korea.
  • 4 Department of Herbal Analysis and Standardization , National Institute of Medicinal Materials , Hanoi , Vietnam.
  • 5 Department of BioMolecular Sciences, Division of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy , The University of Mississippi , University , Mississippi 38677, United States.
PMID: 30354105 DOI: 10.1021/acs.jnatprod.8b00441
Abstract

Hydrogen bonding is a vital feature of a large ensemble of chemical structures. Soluble Epoxide Hydrolase (sEH) has been targeted for development of the treatment for inflammation-associated diseases. Compounds 1 and 2 were purified from Rubia philippinensis, and their structures were established via physical data analysis. Compound 1 possesses intramolecular hydrogen bonding, sufficiently robust to transfer heteronuclear magnetization via a nonbonded interaction. The bonding strength was assessed using the 1H NMR chemical shift temperature coefficients (-1.8 ppb/K), and the heteronuclear coupling constants were measured. The stereochemical details were investigated using interproton distance analysis and ECD. Purified compounds displayed moderate sEH-inhibitory activity.

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