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
  • 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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