Table 1.

Propolis compounds with anticancer activity (in vitro and in vivo models).

Compound Name, IUPAC Name; Concentration Used	Model	Property	Chemical Structure	Reference
Flavonoids, flavanones, flavones and flavonols
Chrysin (5,7-dihydroxy-2-phenylchromen-4-one) 50 μM 5, 25, 50, 80 µg/mL	DU145 and PC-3 cells CAL-27 cells	induction of apoptosis		[25,26]
Galangin (3,5,7-trihydroxy-2-phenylchromen-4-one) 0–40 μM 0–40 μM 10, 20 and 30 mg/kg	mice bearing B16F1 TU212, M4e, HBE, HEP-2 RTE, and HHL-5 cells BALB/c nude mice	induction of apoptosis induction of apoptosis and inhibition of migration		[27,28]
Genistein (5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one) 0–120 μM	LNCaP cells; mouse BALB/c 3T3 and SVT2 (SV40-transformed BALB/c 3T3) fibroblasts	inhibition of cell cycle		[3]
Nymphaeol A/Propolin C ((2S)-2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one) 5–20 μM 2.5–20 μM	A549 cells A549 and HCC827 cells	anti-angiogenic activity, inhibition of proliferation inhibition of migration and invasion		[29,30]
Nymphaeol C ((2S)-2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one) 5–20 μM		anti-angiogenic activity, inhibition of proliferation		[29]
Vestitol (3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol) 0.37, 3.7, 37, and 370 μM	HeLa cells	cytotoxic effect		[31]
Aromatic acids and their derivatives
Artepillin C ((E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid) 250 μM 100 μg/mL 0–150 μM	HT1080, A549, and U2OS cells BALB/c nude mice AGP-01 and HeLa cells CWR22Rv1 cells	inhibition of proliferation cytotoxic effect autophagy inhibition		[32,33,34]
Baccharin ((1R,3S,4S,6R,9R,13S,15R,16S,19R,20E,22Z,26R,27S,28S)-16-hydroxy-19-[(1R)-1-hydroxyethyl]-6,15,27-trimethylspiro [2,5,11,14,18,25-hexaoxahexacyclo [2 4.2.1.03,9.04,6.09,27.013,15]nonacosa-20,22-diene-28,2′-oxirane]-12,24-dione) 0–150 μM	CWR22Rv1 cells	autophagy inhibition		[34]
Caffeic acid ((E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid) 50 and 100 μM 65, 130, 190 µg/mL 30 μg/mL, 200 μg/mL 12.5 μM, 1 mM, 50 μM, 100 mg/kg, 20 mg/kg	MDA-MB-231 cells CAL-27 cells Hep3, SK-Hep1, HepG2 cells	cell cycle arrest in a dose- and time-dependent manner apoptosis activation inhibition of angiogenesis, apoptosis activation		[26,35,36]
Caffeic acid phenylethyl ester (2-phenylethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate) 0.005–0.1 mg/mL 0.5–500 µM 10 mg/kg/day 15 mg/kg	AGS, HCT116, HT29, YD15, HSC-4, HN22, MCF-17, MDA-MB-231, MDA-MB-468, A549, HT1080, G361, U2OS, LNCaP, PC-3, DU145, Hep2, SAS, OECM-1, TW01, TW04, SW620, H460 and PANC-1 cells Balb/c nude mice BALB/c AnM-Foxn-1 mice	inhibition of proliferation, migration and invasion, pro-apoptotic activity anti-metastatic activity		[3,35,37,38,39,40,41,42,43,44,45]
Ferulic acid ((E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid) 50, 100, 150 µg/mL	CAL-27 cells	apoptosis activation		[26]
p-coumaric acid ((E)-3-(4-hydroxyphenyl)prop-2-enoic acid) 100 μg/mL 70, 140, 210 µg/mL	AGP-01 and HeLa cells CAL-27 cells	cytotoxic effect apoptosis activation		[26,33]
Other
Frondoside A (sodium;[(3R,4R,5R,6S)-6-[(2S,4S,6S,12R,13R,18R)-4-acetyloxy-2,6,13,17,17-pentamethyl-6-(4-methylpentyl)-8-oxo-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-1(20)-en-16-yl]oxy]-5-[(2S,3R,4S,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-3-yl] sulfate) 0.3–1.2 μM	A549 cells	anti-angiogenic activity, inhibition of proliferation		[29]
Nemorosone ((1R,5R,7S)-1-benzoyl-4-hydroxy-8,8-dimethyl-3,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione) 5–50 μM	HT-29 and THP-1 cells	inhibition of migration and proliferation		[46]