Isolation, Identification, and Synthesis of a New Prenylated Cinnamic Acid Derivative from Brazilian Green Propolis and Simultaneous Quantification of Bioactive Components by LC-MS/MS

  • J Agric Food Chem. 2019 Nov 6;67(44):12303-12312. doi: 10.1021/acs.jafc.9b04835.
Hiroko Tani  1 ,  Susumu Hikami  1 ,  Shunya Takahashi  2 ,  Yuka Kimura  1 ,  Nobuyasu Matsuura  3 ,  Takemichi Nakamura  2 ,  Masayuki Yamaga  1 ,  Hiroyuki Koshino  2
Affiliations
  • 1. Institute for Bee Products & Health Science, Yamada Bee Company, Incorporated , 194 Ichiba , Kagamino-cho, Okayama 708-0393 , Japan.
  • 2. RIKEN Center for Sustainable Resource Science , Wako, Saitama , 351-0198 , Japan.
  • 3. Department of Life Science, Faculty of Science , Okayama University of Science , 1-1 Ridai-cho , Okayama 700-0005 , Japan.
PMID: 31597041 DOI: 10.1021/acs.jafc.9b04835
Abstract

A new cinnamic acid derivative, (E)-3-[4-hydroxy-3-((E)-3-formyl-2-butenyl)phenyl]-2- propenoic acid (20) has been isolated from the ethanol extract of Brazilian green propolis along with three known cinnamic acid derivatives, 3,4-dihydroxy-5-prenyl-(E)-cinnamic acid (4), capillartemisin A (6), and 2,2-dimethylchromene-6-(E)-propenoic acid (8), and a flavonoid, dihydrokaempferide (16) by liquid-liquid participation, a series of column chromatography and preparative HPLC. Their structures have been determined by spectroscopic analyses and chemical synthesis of compound 20. The simultaneous quantification of 20 constituents, including 10 cinnamic acid derivatives, 7 Flavonoids, and 3 caffeoylquinic acid derivatives, has also been developed and validated using LC-MS/MS. The new compound 20 was shown to activate PPAR α but not PPAR β or γ.

Keywords
Baccharis dracunculifolia; Brazilian green propolis; LC-MS; PPARs; caffeoylquinic acid derivatives; cinnamic acid derivatives; flavonoid; simultaneous quantification.
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