Comparative Chemistry of Propolis from Eight Brazilian Localities

Table 4

Constituents from the chloroform and methanol extracts of samples of Brazilian propolis from the municipalities of Pariquera-Açu (Par; state of São Paulo), Ponta Grossa (PGr; state of Paraná), Bauru (Bau; state of São Paulo), Lavras (Lav; state of Minas Gerais), Cabo Verde (CVe; state of Bahia), Mira Bela (MBe; state of Minas Gerais), Picos (Pic; state of Piauí), and Pirenópolis (Pir; state of Goiás). Compounds are characterized by GC/EIMS and HPLC/ESIMS.

Compounds		Samples
		Par	PGr	Bau	Lav	CVe	MBe	Pic	Pir
1	4-Vinyl phenol			x	x
2	Dihydrocinnamic acid Methyl ester				x
3	p-Vinyl-O-prenyl phenol				x
4	2-T-butylnaphto-[2,3-b]-furan,4,9-dione			x	x
5	p-Hydroxycinnamic acid methyl ester					x
6	Methyl-O-benzoylbenzoate	x
7	Benzene ethoxy	x
8	n-Hexadecanoic acid methyl ester							x	x
9	Allyl-3-prenylcinnamate			x	x	x
10	2,2-Dimethylchromene-6-propenoic acid methyl ester		x
11	Palmitic acid				x
12	Pinobanksin methyl ether								x
13	Oleic acid methyl ester							x
14	4-Hydroxy-3-prenylcinnamic acid methyl ester			x	x	x
15	n-Stearic acid methyl ester							x
16	Ferulic acid octadiene ester								x
17	Methyl dehydroabietate	x	x
18	n-Propyl-p-hydroxybenzoate	x
19	12,16-Epoxy-6-hydroxy-(15-16)-abeo-5,8,11,13-abietatetraene-7-one				x
20	Pentyl benzene		x
21	Ferulic acid octaene ester								x
22	n-Phenyl hexadecane				x
23	Ethyl dehydroabietate	x	x
24	Hydroxy-diprenylcinnamic acid methyl ester (artepillin C)			x	x	x
25	2,2-Dimethyl-8-prenylchromene-6-propenoic acid methyl ester		x	x	x	x
26	Pinobanksin-5-methyl ether acetate			x
27	Benzoic acid, 4(4-hydroxybenzoyl)-methylester		x
28	3-Hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid methyl ester			x		x
29	Benzoic acid, 2-propoxy-(4-hydroxybenzoyl)-methyl ester		x
30	Benzylic alcohol, 2-propoxy-(4-hydroxybenzoyl)-methyl ester		x
31	Benzoic acid, 2(4-hydroxybenzoyl)-methylester		x
32	n-Docosanoic acid methyl ester							x
33	n-Heptacosane								x
34	n-Tetracosanoic acid methyl ester							x
35	4-Dihydrocinnamoiloxy-3-prenylcinnamic acid methyl ester			x	x	x
36	n-Nonacosane								x
37	n-Hentriacontane							x	x
38	Carbomethoxy benzyl caffeate ester							x
39	Dihydrocaffeoyl-dihydrocinnamoyl-glyceride								x
40	β-amyrin	x	x		x
41	Propyl carbomethoxy benzyl dihydrocaffeate ester							x
42	Ergosterol								x
43	Lupenone								x
44	β-Amyrinone							x	x
45	α-Amyrinone							x	x
46	α-Amyrin								x
47	β-Amyrin acetate							x
48	α-Amyrin acetate					x		x
49	Taraxerone								x
50	Oleanene								x
51	Pteron-14-en-7-one								x
52	Olean-14-en-3,28-dione								x
53	Homovanillic acid				x
54	Caffeic acid 4-O-glucoside	x	x			x	x	x	x
55	Quinic acid		x	x	x	x	x	x	x
56	Dihydroquercetin							x
57	Caffeoylquinic acid			x
58	Caffeic acid 4-O-arabinoside							x
59	Caffeic acid 4-O-xyloside							x
60	Caffeoylquinic acid	x	x		x	x
61	Feruloyl-caffeoylquinic acid			x	x
62	Caffeoylquinic acid				x
63	Methoxy-dihydroxy benzoic acid							x
64	Dimethoxyluteolin-glucoside				x
65	Tricaffeoylquinic acid			x			x
66	Caffeoylquinic acid		x
67	Feruloyl-caffeoylquinic acid			x	x
68	Feruloyl-caffeoylquinic acid			x	x
69	Methylkaempferol-O-rutinoside							x
70	Naringenin-C-glucoside						x		x
71	Apigenin-O-rutinoside	x							x
72	Feruloylquinic acid					x	x
73	Caffeic acid	x
74	Delphinidin arabinoside						x		x
75	Caffeoylquinic acid		x		x	x
76	Catechin arabinoside							x
77	Apigenin-di-C-glucosyl rhamnoside						x
78	Apigenin-C-rhamnoside								x
79	Apigenin-6,8-di-C-glucoside (vicenin-2)				x	x	x		x
80	Apigenin-C-rhamnosyl arabinoside						x		x
81	Apigenin-6-C-glucosyl-8-C-arabinose (isoschaftoside)	x	x		x	x
82	Apigenin-C-rhamnoside						x
83	Luteolin-O-glucuronide				x
84	Dicaffeoylquinic acid	x	x	x	x	x
85	Caffeic acid-dihydroxy phenyl ethyl ester			x
86	Dicaffeoylquinic acid	x	x
87	Dicaffeoylquinic acid	x	x
88	Apigenin-8-C-glucosyl-6-C-arabinose (schaftoside)	x	x		x	x
89	Luteolin-6,8-di-C-glucoside (lucenin-2)					x
90	Pentosyl orientin					x
91	Vitexin	x				x
92	Quercetin-O-glucoside							x
93	Dicaffeoylquinic acid	x	x	x	x	x
94	Ferulic acid-methoxy trihydroxy phenyl ethyl ester			x
95	Hydroxy-prenylcinnamic acid			x
96	3-Prenyl-4-(2-methylpropionyloxy)-cinnamic acid methyl ester			x
97	Luteolin acetyl glucoside	x	x
98	Chrysoeriol-C-glucoside					x
99	Dimethoxy naringenin-diglucoside					x
100	Caffeoylferuloylquinic acid	x
101	Apigenin-di-O-glucoside					x
102	Quercetin-O-arabinoside							x
103	Quercetin-O-rhamnoside							x
104	Dicaffeoylquinic acid	x	x		x	x
105	Isorhamnetin-glucoside							x
106	Tricaffeoylquinic acid	x	x		x	x
107	Tricaffeoylquinic acid				x
108	Apigenin-O-glucuronide				x
109	Diprenyl chrysin								x
110	Ferulic acid dihydroxy phenyl ethyl ester			x
111	Quercetin							x
112	Cinnamoyl hexoside								x
113	Caffeoylferuloylquinic acid					x
114	Isorhamnetin							x	x
115	Rhamnetin							x	x
116	Laricitin								x
117	3-Hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid							x
118	Methyl licochalcone B							x
119	Hydroxy-diprenylcinnamic acid (artepillin C)			x
120	Quercetin-dimethyl ether							x
121	Pentamethoxy hydroxy flavonol								x
122	Pentamethoxy flavonol								x
123	Nobiletin								x
124	Chrysin rhamnoside								x
125	Prenyl-trimethoxyluteolin								x
126	Prenyl-methoxyquercetin								x
127	Phloretin								x
128	Prenyl-methoxyquercetin								x
129	Prenyl-methoxykaempferol					x			x
130	Prenyl-dimethoxyquercetin								x
131	Prenyl-dimethoxykaempferol								x
132	Prenyl-dimethoxykaempferol								x
133	Prenyl-trimethoxykaempferol								x