Chemical Composition and Anti-Inflammatory Effect of Ethanolic Extract of Brazilian Green Propolis on Activated J774A.1 Macrophages

Table 1

The content [mg/g] and characterization of phenolic compounds of the ethanol extract of Brazilian green propolis using their spectral characteristic in negative ions in LC-ESI/MS.

Peak	Retention time 𝑡𝑟  (min)	[M−H]^−	MS/MS fragments	Compound name*	Quantity; [mg/g of propolis]**
(1)	1.96	353.0879	191.0553/173.0446/161.0241/135.0440	Caffeoylquinic acid isomer^b,c	6.49^e
(2)	2.26	179.0349	161.0241/135.0440	Caffeic acid^a	1.29
(3)	2.79	163.0406	119.0510	p-Coumaric acid^a	19.90
(4)	3.02	193.0492	193.0492	Ferulic acid^a	1.48
(5)	3.30	515.1196	353.0879/191.0553/179.0349/161/0241/135.0440	Dicaffeoylquinic acid izomer^b,c	2.22^e
(6)	3.46	515.1196	353.0879/191.0553/179.0349/161/0241/135.0441	Dicaffeoylquinic acid izomer^b,c	2.55^e
(7)	3.65	231.0652	187.0760/163.0380/145.0653	Coumaric acid prenyl ester^b	0.14^d
(8)	3.84	487.1597	263.0911/179.0349/161.0241	Caffeic acid derivative^c	0.55^e
(9)	4.27	677.1512	515.1196/353.0879/191.0553/179.0349/161.0241/135.0441	Tricaffeoylquinic acid^b,c	0.46^e
(10)	4.43	543.1486	381.1173/179.0349/161.0241	Dimethyl-dicaffeoylquinic acid^c	3.00^e
(11)	4.65	543.1486	381.1173/179.0349/161.0241	Dimethyl-dicaffeoylquinic acid^c	3.61^e
(12)	4.89	271.0616	151.0017/133.0654/107.0134	Naringenin^a	0.54
(13)	4.96	285.0394	285.0394	Kempferol^a	3.35
(14)	5.01	315.0512	301.0709/151.0017	Isorhamnetin^b,c	3.18^h
(15)	5.08	301.0709	152.0119/	Hesperitin^a	8.42
(16)	5.25	301.1455	239.1426/202.0992/132.0568	Ni	—
(17)	5.43	705.1837	543.1486/381.1173/179.0349/161.0241	Caffeic acid derivative^c	0.83^e
(18)	5.63	247.0982	203.1072/148.0535	3,4-Dihydroxy 5-prenylcinnamic acid^b	2.41^d
(19)	5.71	331.1565	331.1565	Ni	2.75^d
(20)	5.89	231.1025	187.1124/132.0568	4-Hydroxy 3-prenylcinnamic acid (drupanin)^b	25.63^d
(21)	6.05	315.1602	253.1609/201.1286/146.0728	Coumaric acid derivative^c	3.61^d
(22)	6.44	285.0775	164.0171/119.0510	Sakuranetin^a	2.43
(23)	6.46	285.0775	164.0116/151.0042/135.0162/108.0215	Izosakuranetin^a	3.39
(24)	6.51	255.0663	255.0663/	Pinocembrin^a	3.12
(25)	6.59	299.0572	284.0313/201.1286/151.0042	Kaempferide^a	18.81
(26)	6.72	377.1958	299.0572/201.1286	Kaempferide derivative^c	10.18^g
(27)	6.78	393.1335	163.0380/145.0284/119.0510	Dicoumaric prenyl ester^c	3.71^d
(28)	6.87	315.1602	299.0536/253.1609/198.1039	Ni	4.16^d
(29)	7.03	313.1433	211.1126/156.0583/149/0618	Ni	0.61^d
(30)	7.10	529.1495	299.0572/284.0313	Kaempferide derivative^c	0.07^g
(31)	7.22	315.1602	201.1286/146.0728	Ni	0.06^d
(32)	7.42	559.1631	329.0666/163.0380/145.0284/119.0488	Coumaric acid derivative^c	0.42^d
(33)	7.49	329.1780	299.1634/255.1742	Artepillin C derivative^c	—
(34)	7.61	545.2541	331.1900/269.1174	Ni	—
(35)	7.70	477.1917	211.1126/163.0380/145.0284/118.0415	Coumaric acid derivative^c	0.63^d
(36)	8.06	299.1634	255.1742/200.1197	Artepillin C^a	51.44
(37)	8.40	585.1772	301.1455/125.0974	Ni	—
(38)	8.91	447.2171	297.1489/149.0613	Ni	—
(39)	9.13	363.1619	187.1124/149.0613/131.0497	3-Prenyl-4-(dihydrocinnamoyloxy)-cinnamic acid (baccharin)^b	9.66^d
(40)	9.32	297.1489	253.1577/198.1039/152.9951	Ni	0.62^d
(41)	9.51	321.2426	299.1634/255.1742	Artepillin derivative^c	0.89^e
(42)	9.77	321.2426	299.1634/255.1742	Artepillin derivative^c	2.99^e
(43)	10.99	613.3177	299.1634/281.1550/154.1682	Artepillin derivative^c	1.41^e

Ni: not identified.
^*,aConfirmed by standard.
^bConfirmed by reference [19–21, 23, 24, 26].
^cConfirmed by MS fragmentation.
^**,dExpressed as p-coumaric acid.
^eExpressed as caffeic acid.
^fExpressed as artepillin C.
^gExpressed as kaempferide.
^hExpressed as rhamnetin.