Tadehaginosides A-J, Phenylpropanoid Glucosides from Tadehagi triquetrum, Enhance Glucose Uptake via the Upregulation of PPARγ and GLUT-4 in C2C12 Myotubes

  • J Nat Prod. 2016 May 27;79(5):1249-58. doi: 10.1021/acs.jnatprod.5b00820.
Xiaopo Zhang  1 ,  Changyu Chen  1 ,  Yonghui Li  1 ,  Deli Chen  2 ,  Lin Dong  1 ,  Wei Na  1 ,  Chongming Wu  2 ,  Junqing Zhang  1 ,  Youbin Li  1
Affiliations
  • 1. School of Pharmaceutical Science, Hainan Medical University , Hainan 571199, People's Republic of China.
  • 2. Institute of Medicinal Plant Development, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100193, People's Republic of China.
PMID: 27100993 DOI: 10.1021/acs.jnatprod.5b00820
Abstract

Ten new phenylpropanoid glucosides, tadehaginosides A-J (1-10), and the known compound tadehaginoside (11) were obtained from Tadehagi triquetrum. These phenylpropanoid glucosides were structurally characterized through extensive physical and chemical analyses. Compounds 1 and 2 represent the first set of dimeric derivatives of tadehaginoside with an unusual bicyclo[2.2.2]octene skeleton, whereas compounds 3 and 4 contain a unique cyclobutane basic core in their carbon scaffolds. The effects of these compounds on glucose uptake in C2C12 myotubes were evaluated. Compounds 3-11, particularly 4, significantly increased the basal and insulin-elicited glucose uptake. The results from molecular docking, luciferase analyses, and ELISA indicated that the increased glucose uptake may be due to increases in Peroxisome Proliferator-activated Receptor γ (PPARγ) activity and glucose transporter-4 (GLUT-4) expression. These results indicate that the isolated phenylpropanoid glucosides, particularly compound 4, have the potential to be developed into antidiabetic compounds.

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