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

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.