Table 2.

Phenolic compounds identified in propolis with gastroprotective effect induced by NSAIDs.

Compound	Activity Related to Gastroprotective Effect							Country of Origin of Propolis Sample	Activity References
	Ga	Au	As	Af	Im	Ax	Cp
2,2-dimethyl-6-carboxyethenyl-2H-1-benzopirane								Brazil [67]
3-prenyl-4-dihydroxycinnamoiloxy cinnamic acid (baccharin)								Brazil [67,68]
3-prenyl-4-hidroxycinamic acid (drupanin)	X	X	X	X		X		Brazil [57,68]	[68,69]
3,4-dimethoxycinnamic acid						X		Mexico [70]	[70]
3,5-diprenyl-4-hidroxycinamic acid (artepillin C)	X	X	X	X	X	X		Brazil [57,67,68,71,72,73]	[68,74,75]
3.3-dimethylallyl caffeate						X		Mexico [70]	[70]
5-methylchrysin ether						X		Mexico [76]	[76]
5-methylgalangin ether						X		Mexico [76,77]	[76]
5-methylpinobanksin ether						X		Mexico [76,77]	[76]
7-O-methylvestitol	X				X	X	X	Brazil [63]	[63]
Acacetin				X	X	X	X	Mexico, Brazil [78,79,80]	[81,82]
Alnusin								Brazil [83]
Alpinetin				X		X	X	Mexico [76,77]	[76,84]
Alpinone					X			Mexico [77]	[85]
Anethole	X			X		X		Brazil [83]	[86,87]
Anisaldehyde								Brazil [83]
Apigenin	X		X		X	X	X	Mexico [60,79]	[88,89]
Aromadendrine-4′-O-metyl ether	X		X					Brazil [57,68]	[68]
Baicalein	X	X	X	X	X	X	X	Mexico [60]	[55]
Benzoic acid				X		X		Brazil [71,83]	[90]
Biochanin A	X	X	X	X	X	X	X	Brazil [83,91]	[92,93,94,95,96]
Cadinene						X		Brazil [83]	[97]
Caffeic acid	X	X	X	X	X	X	X	Brazil, Mexico [57,70,72,73,76,98,99]	[76,98,100,101,102,103]
Caffeic acid phenethyl ester (CAPE)	X	X	X	X	X	X	X	Denmark, Mexico, Brazil [58,73,79,104]	[105,106,107,108,109]
Calycosin	X					X		Brazil [80]	[110]
Catechin	X			X		X		Mexico, Brazil [60,99,111]	[88,112,113]
Catechol	X	X		X		X		Mexico [60]	[114,115]
Cholorgenic acid	X	X	X	X		X	X	Brazil [73]	[116]
Chrysin	X		X		X	X		Mexico, Brazil [60,76,77,78,79,80,104,117]	[56,76]
Cinnamic acid	X	X	X	X	X	X	X	Brazil, Mexico [70,71,79,98]	[98,118,119]
Daidzein				X		X		Brazil [91]	[120,121]
Dalbergin								Brazil [80]
Dihydrocinnamic acid								Brazil [71]
Dihydroxy-methoxy chalcone								Brazil [122]
Dihydroxy-methoxy flavanone								Brazil [122]
Dihydroxy-trimethoxyflavone								Brazil [122]
Dillenetin						X		Mexico [76]	[76]
Dimethoxy-dihydrochalcone								Brazil [122]
Elemicin								Brazil [83]
Epicatechin	X							Brazil [99]	[123]
Epoxypinocembrin chalcone						X		Mexico [70]	[70]
Ferulic acid	X	X	X	X	X	X	X	Brazil, Mexico [76,79,98,111]	[76,98,103,124,125]
Formononetin	X	X		X	X	X		Brazil [59,83,91,99]	[59,95,126,127,128]
Galangin	X		X		X	X		Mexico [76,79,117]	[76,129,130]
Gallic acid	X	X		X		X	X	Mexico, Brazil [72,79,99]	[131]
Genkwanin				X		X		Brazil [80]	[132]
Guaiacol				X		X		Brazil [83]	[133,134]
Hesperetin	X	X		X		X	X	Mexico [104]	[135,136,137]
Hispidulin				X		X		Brazil [80]	[110]
Isocholorgenic acid A				X	X	X	X	Brazil [73]	[138]
Isocholorgenic acid B								Brazil [73]
Isocholorgenic acid C								Brazil [73]
Isoelemicin								Brazil [83]
Isopent-3-enyl caffeate						X		Mexico [70]	[70]
Isorhamnetin				X		X	X	Mexico [76,77]	[76,139]
Isorhamnetin-3-O-glucosylgallate								Brazil [122]
Isosakuranetin (ponciretin)		X						Brazil [57]	[140]
Izalpinin						X		Mexico [70]	[70]
Kaempferide	X		X	X				Brazil, Mexico [68,77]	[68]
Kaempferol	X		X	X		X		Mexico, Brazil [60,70,78,79,99,122]	[53,54,70,88,120]
Liquiritigenin				X	X	X	X	Brazil [83]	[141,142,143]
Luteolin	X			X	X	X	X	Mexico, Brazil [78,79,111]	[89,112,135,144,145]
Medicarpin	X			X	X	X		Brazil [63,80,83]	[63,146]
Methoxy-dihydrochalcone								Brazil [122]
Methoxyeugenol						X		Brazil [83]	[147]
Methyl eugenol	X			X		X	X	Brazil [83]	[148,149]
Myricetin-3-O-rhamnoside				X		X		Brazil [122]	[150,151]
Naringenin	X			X	X	X	X	Mexico [60,78,79,104]	[88,120,152]
Naringin	X	X		X		X		Mexico [60,78]	[88,153,154]
Neovestitol				X		X		Brazil [63,155]	[155,156]
Oblongifolin B								Brazil [63,80]
p-coumaric acid	X	X		X	X	X		Brazil, Mexico [57,71,72,79,98,99]	[98,103,157,158]
Pentahydroxy-flavone-malonyl gallate								Brazil [122]
Pinobanksin						X		Mexico, Brazil [77,80]	[159]
Pinobanksin-3-O-acetate								Mexico [79,117]
Pinocembrin	X	X	X	X	X	X	X	Mexico, Brazil [60,70,72,76,77,78,79,91,104,117]	[70,76,77,85,129,160]
Pinostrobin						X		Mexico [70,77,79]	[161]
Prenyl-p-coumaric	X		X					Brazil [71]	[68]
Prenyl-pentahydroxy-flavone								Brazil [122]
Quercetin	X	X	X	X	X	X	X	Mexico, Brazil [78,79,99,122]	[89,120,162,163,164]
Retusapurpurin								Brazil [83]
Rhamnetin				X		X		Mexico [70]	[165]
Rutin	X	X	X	X		X	X	Mexico, Brazil [99,104]	[166,167]
Syringic acid				X		X	X	Mexico [76]	[76,168]
Tetrahydroxy flavonon								Brazil [71]
Trans-ferulic acid				X		X		Brazil [99]	[169,170]
Tricin				X		X		Brazil [80]	[171,172]
Trihydroxy-dihydrocinnamic acid								Brazil [122]
Trihydroxy-dimethoxy chalcone								Brazil [122]
Tryhidroxymethoxy flavonon								Brazil [71]
Vestitol	X			X		X		Mexico, Brazil [63,80,83]	[95,155]
Vestitone								Brazil [80]
Violanthin						X		Brazil [122]	[173]
Xanthochymol								Brazil [83]
ε-caprolactone derivative								Mexico [70]

Only articles that reported the chemical composition of Brazil green and red propolis and North Mexican brown propolis were included in this table; moreover, we only included CAPE as a compound of Danish propolis due to the unique compound identified in the chemical composition of the work that evaluated the antiulcerative activity of this propolis [58]. Ga: gastroprotective; Au: antiulcerative; As: antisecretory; Af: anti-inflammatory; Im: immunomodulator; Ax: antioxidant; and Cp: cytoprotective.