Comparative Chemistry of Propolis from Eight Brazilian Localities

Table 3

Constituents from the methanol extract of Brazilian propolis from Paraná (south), São Paulo and Minas Gerais (southeast), Goiás (central), Bahia (northeast), and Piauí (central-north) states, characterized by HPLC/DAD/ESI/MS.

Compound	Rt (min)	UV/DAD	[M–H]^−	Proposed structure
53	4.9	270	181	Homovanillic acid
54	5.5	300, 330	341.2	Caffeic acid 4-O-glucoside
55	5.7	ND	191.1	Quinic acid
56	15	290	303.1	Dihydroquercetin
57	16.1	330, 300	353	Caffeoylquinic acid
58	16.3	300, 330	311	Caffeic acid 4-O-arabinoside
59	19.5	300, 330	311.2	Caffeic acid 4-O-xyloside
60	19.6	300, 330	353.1	Caffeoylquinic acid
61	20.3	330, 300	529	Feruloyl-caffeoylquinic acid
62	20.4	300, 330	353.3	Caffeoylquinic acid
63	21.9	ND	183	Methoxy-dihydroxy benzoic acid
64	22.1	270, 340	475.5	Dimethoxy-luteolin-glucoside
65	22.3	300, 330	677.1	Tricaffeoylquinic acid
66	22.3	330, 300	353.5	Caffeoylquinic acid
67	22.3	330, 300	529	Feruloyl-caffeoylquinic acid
68	22.7	330, 300	529	Feruloyl-caffeoylquinic acid
69	23.8	ND	607.3	Methylkaempferol-O-rutinoside
70	23.9	280, 330sh	433.3	Naringenin-C-glucoside
71	24	270, 338	577.5	Apigenin-O-rutinoside
72	24.3	300, 330	367.5	Feruloylquinic acid
73	24.9	ND	179.3	Caffeic acid
74	25.2	ND	435.1	Delphinidin arabinoside
75	25.7	330, 300	353.3	Caffeoylquinic acid
76	26.4	ND	421.2	Catechin arabinoside
77	27.1	270, 338	577.1	Apigenin-di-C-glucosyl rhamnoside
78	27.4	270, 338	415.3	Apigenin-C-rhamnoside
79	27.7	270, 338	593.1	Apigenin-6,8-di-C-glucoside (vicenin-2)
80	28.3	270, 338	547	Apigenin-C-rhamnosyl arabinoside
81	28.8	270, 340	563.5	Apigenin-6-C-glucosyl-8-C-arabinose (isoschaftoside)
82	29.3	270, 340	415.4	Apigenin-C-rhamnoside
83	29.6	270, 338	461	Luteolin-O-glucuronide
84	33.6	300, 330	515.4	Dicaffeoylquinic acid
85	35.8	330, 300	315	Caffeic acid-dihydroxy phenyl ethyl ester
86	36	300, 330	515.8	Dicaffeoylquinic acid
87	37.2	330, 300	515	Dicaffeoylquinic acid
88	38.6	270, 340	563.6	Apigenin-8-C-glucosyl-6-C-arabinose (schaftoside)
89	41.4	270, 340	609.4	Luteolin-6,8-di-C-glucoside (lucenin-2)
90	42.7	270, 340	579.3	Pentosyl orientin
91	42.8	270, 340	431	Vitexin
92	44.3	ND	463.3	Quercetin-O-glucoside
93	45.8	ND	515.3	Dicaffeoylquinic acid
94	48.4	330, 300	375.1	Ferulic acid-methoxy trihydroxy phenyl ethyl ester
95	49.1	310	231.2	Hydroxy-prenylcinnamic acid
96	49.8	310	315.4	3-Prenyl-4-(2-methylpropionyloxy)-cinnamic acid methyl ester
97	52.3	270, 340	489.8	Luteolin acetylglucoside
98	52.5	270, 340	461.2	Chrysoeriol-C-glucoside
99	53.1	280	623.4	Dimethoxy naringenin-diglucoside
100	53.8	300, 330	529.7	Caffeoylferuloylquinic acid
101	54.1	270, 340	593.3	Apigenin-di-O-glucoside
102	54.6	256, 356	433	Quercetin-O-arabinoside
103	55.5	260, 355	447.1	Quercetin-O-rhamnoside
104	56.3	300, 330	515.9	Dicaffeoylquinic acid
105	56.6	260, 350	477.1	Isorhamnetin-glucoside
106	58.8	300, 330	677.4	Tricaffeoylquinic acid
107	59.8	330, 300	677.3	Tricaffeoylquinic acid
108	60.4	270, 335	445.1	Apigenin-O-glucuronide
109	60.5	ND	389.3	Diprenyl chrysin
110	60.6	330	329	Ferulic acid dihydroxy phenyl ethyl ester
111	65.9	260, 353	301.2	Quercetin
112	66	ND	309.1	Cinnamoyl hexoside
113	66.5	330, 300	529.6	Caffeoylferuloylquinic acid
114	67.9	256, 356	315.1	Isorhamnetin
115	70.6	256, 356	315.1	Rhamnetin
116	71.2	255, 354	331	Laricitin
117	72.1	310	315.5	3-Hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid
118	72.3	230, 350	299.1	Methyl licochalcone B
119	73	310	299	Hydroxy-diprenylcinnamic acid (artepillin C)
120	73.9	256, 356	329.1	Quercetin-dimethyl ether
121	74.2	ND	387.4	Pentamethoxy hydroxy flavonol
122	76.9	ND	371.6	Pentamethoxy flavonol
123	78	ND	401.2	Nobiletin
124	79.1	ND	399.5	Chrysin rhamnoside
125	82.1	ND	395.2	Prenyl-trimethoxyluteolin
126	83.2	255, 355	383.4	Prenyl-methoxyquercetin
127	86	260, 370	273.1	Phloretin
128	87.5	260, 360	383.3	Prenyl-methoxyquercetin
129	88.1	260, 360	367.1	Prenyl-methoxykaempferol
130	88.9	ND	397.2	Prenyl-dimethoxyquercetin
131	89.9	260, 355	381.2	Prenyl-dimethoxykaempferol
132	91.1	260, 350	381.8	Prenyl-dimethoxykaempferol
133	93.1	260, 360	395.2	Prenyl-trimethoxykaempferol