Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition

  • Bioorg Med Chem Lett. 2004 Jun 7;14(11):2893-6. doi: 10.1016/j.bmcl.2004.03.037.
Sirichai Adisakwattana  1 ,  Kasem Sookkongwaree ,  Sophon Roengsumran ,  Amorn Petsom ,  Nattaya Ngamrojnavanich ,  Warinthorn Chavasiri ,  Sujitra Deesamer ,  Sirintorn Yibchok-anun
Affiliations
  • 1. Department of Pharmacology, 39, Faculty of Veterinary Science, Chulalongkorn University, Bangkok 10330, Thailand.
PMID: 15125954 DOI: 10.1016/j.bmcl.2004.03.037
Abstract

trans-Cinnamic acid and its derivatives were investigated for the alpha-glucosidase inhibitory activity. 4-Methoxy-trans-cinnamic acid and 4-methoxy-trans-cinnamic acid ethyl ester showed the highest potent inhibitory activity among those of trans-cinnamic acid derivatives. The presence of substituents at 4-position in trans-cinnamic acid altered the alpha-glucosidase inhibitory activity. Increasing of bulkiness and the chain length of 4-alkoxy substituents as well as the increasing of the electron withdrawing group have been shown to decrease the inhibitory activity. 4-Methoxy-trans-cinnamic acid was a noncompetitive inhibitor for alpha-glucosidase, whereas, 4-methoxy-trans-cinnamic acid ethyl ester was a competitive inhibitor. These results indicated that trans-cinnamic acid derivatives could be classified as a new group of alpha-glucosidase inhibitors.

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