Report on the Malungo expedition to the Erepecuru river, Oriximiná, Brazil. Part I: is there a difference between black and white <i>breu</i>?

Silva, Eduardo Rodrigues da; Oliveira, Danilo Ribeiro de; Melo, Maria de Fátima Figueiredo; Bizzo, Humberto Ribeiro; Leitão, Suzana Guimarães

doi:10.1016/j.bjp.2016.05.003

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Original articles • Rev. bras. farmacogn. 26 (5) • Sep-Oct 2016 • https://doi.org/10.1016/j.bjp.2016.05.003 copy

Report on the Malungo expedition to the Erepecuru river, Oriximiná, Brazil. Part I: is there a difference between black and white breu?

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

Species belonging to Burseraceae produce an oleoresin known in the north of Brazil as breu. They comprise an essential oil with a complex composition, and are used in Amazonia for smoking the environment, to caulk boats and for medicinal purposes. Depending on its organoleptic characteristics and on the breu-producing species, they are called white or black breu. In this work, we provide data about the breu-producing species occurring in the quilombola region of the Erepecuru river, the chemical composition, and whether it is possible to differentiate them based on their chemical composition and/or botanical identification. Aerial samples from breu trees and oleoresins were collected from 10 different individuals at 6 different sites on the Erepecuru river under the guidance of the quilombolas. Essential oils were extracted by hydrodistillation and characterized by GC–MS. From the analysis, 126 different substances were identified, with a large quantitative and qualitative variation. To better understand the chemical variations within the samples and to sort the variation into the categories of white or black breu as identified by the quilombola, we sorted the oil samples into five different sets according to their major compounds (A: δ-3-carene; B: p-cymene; C: γ-cadinene/p-cymene; D: limonene, β-phellandrene/α-terpineol; E: α-pinene/limonene). Essential oils from samples of white breu had the highest concentration of α-pinene, while a similarity in chemical composition could not be established for the black breu samples (sets A, B and C). Furthermore, a chemical similarity between a black breu (Protium heptaphyllum (Aubl.) Marchand) and a white breu (Protium decandrum (Aubl.) Marchand) sample was evidenced. In conclusion, it is difficult to establish definitions for white and black breu based on chemical, botanical or regional names. This designation is more cultural and regional than scientific and is based on the oleoresin production volume, its color aspect and scent.

Keywords:
Burseraceae; Protium; Breu; Quilombola; Essential oil

Sample	Voucher numbers	Popular name	Identified species
BBIM	265857	Black breu or breuzinho	Protium heptaphyllum (Aubl.) Marchand
BBPIR	265850	Black breu	Protium decandrum (Aubl.) Marchand
BBIR₁	265852	Black breu	Protium heptaphyllum (Aubl.) Marchand
BBIR₂	265851	Black breu	Protium heptaphyllum (Aubl.) Marchand
BBIR₃	265855	Black breu	Protium heptaphyllum (Aubl.) Marchand
WBB₁	265856	White breu	Protium decandrum (Aubl.) Marchand
BBTF₁	265859	Black breu or sucuruba	Protium cf. opacum Swart
BBTF₂	265858	Black breu or sucuruba	Protium altsonii Sandwith
WBB₂	265954	White breu	Protium occultum D.C. Daly
WBIG	265853	White breu	Protium strumosum Daly

		BBIM	BBPIR	BBIR1	BBIR2	BBIR3	WBB1	BBTF1	BBTF2		WBB2		WBIG
Moisture %		4	6	7	14	6	10	9	2		9		12
Yield % (w/w)		1.2	3.86	1.79	2.47	2.9	2.85	1.02	2.59		0.79		5.36
Refractive index^a a Measured at 20 ºC.		1.4733	1.4693	1.4720	1.4693	1.4703	1.4730	1.4937	1.4830		1.4730		1.4673
Optical rotation (º)^a a Measured at 20 ºC.		−0.059	+3.485	−0.282	+1.507	+3.664	+2.321	−0.668	+0.733		−2.179		+2.510
Essential oil grouping according to major compounds		A				B		C			D		E
S.N.	Substance	IR_lit**	IR***	Percentage (%)
1	α-thujene	930	927	–	1.2	–	0.4	0.3	–	0.1	0.2	–	0.9
2	α-pinene	939	934	2.0	4.9	2.2	1.7	1.2	19.0	0.2	0.9	8.0	57.7
3	camphene	954	949	–	2.2	0.4	–	–	0.3	–	0.3	–	1.2
4	verbenene	967	969	1.5	–	0.8	0.4	–	–	–	–	–	–
5	sabinene	975	973	–	–	–	–	–	0.2	–	–	–	–
6	trans-p-menthane	979	975	–	–	–	–	–	–	0.1	–	1.0	–
7	β-pinene	979	980	–	2.3	0.5	–	–	3.6	–	–	–	9.3
8	2-menthene	_	980	0.6	–	–	0.6	–	–	0.5	0.8	–	–
9	3-p-menthene	987	984	–	–	–	–	–	–	0.7	1.1	–	0.9
10	mircene	990	990	0.5	1.7	0.3	0.6	–	–	–	–	–	–
11	camphane	–	1001	–	–	–	0.7	0.7	–	–	–	–	–
12	bornane	–	1001	–	–	–	–	–	3.0	–	–	–	–
13	1,3,8-p-menthatriene	–	1008	–	–	–	–	0.5	–	–	–	–	–
14	α-phellandrene	1002	1005	0.9	–	2.1	12.9	–	21.0	4.0	–	–	–
15	mix (δ-3-carene and iso-sylvestrene)	1011	1011	69.0	40.9	79.5	56.4	14.7	0.8	–	1.2	0.5	–
16	α-terpinene	1017	1017	–	–	–	1.6	–	5.5	2.7	–	–	0.6
17	p-cymene	1024	1026	6.4	13.4	3.5	14.0	33.0	32.4	6.6	16.3	10.4	9.2
18	1-p -menthene	1026	1022	–	–	–	–	–	0.7	–	0.2	0.8	–
19	mix (limonene and β-phellandrene)	1029	1028	5.7	20.3	3.2	6.8	–	12.0	4.3	–	41.1	10.8
20	1,8-cineole	1031	1031	–	–	1.5	–	–	–	–	–	–	–
21	γ-terpinene	1059	1059	–	1.6	–	–	–	0.5	0.2	–	–	3.4
22	m-cyminene	1085	1085	–	–	–	–	0.2	–	–	–	–	–
23	terpinolene	1088	1088	1.1	1.4	0.7	0.7	–	–	1.0	–	0.7	0.5
24	p-cymenene	1091	1092	–	–	–	–	0.6	–	–	0.1	–	–
25	linalool	1096	1102	–	0.4	–	–	–	–	–	–	–	–
26	cis-p-menth-2en-1-ol	1121	1123	–	–	–	–	0.2	–	–	0.1	–	–
27	cyclooctanone	–	1129	–	–	–	–	0.5	–	–	0.5	–	–
28	cis-limonene oxide	1136	1137	–	–	–	–	0.4	–	–	–	–	–
29	trans-dihydro-β-terpineol	1138	1137	–	–	–	–	–	–	0.1	–	–	–
30	camphor	1146	1146	–	0.5	0.8	–	–	0.5	–	–	–	1.4
31	trans-dihydro-α-terpineol	1147	1147	–	–	–	–	1.0	–	2.3	2.4	3.3	–
32	cis-dihydro-β-terpineol	1160	1158	–	–	–	–	–	–	0.04	–	–	–
33	cis-dihydro-α-terpineol	1164	1162	–	–	–	–	–	–	0.1	0.2	–	–
34	p-mentha-1,5-dien-8-ol	1170	1167	2.4	0.4	1.4	–	–	–	–	–	–	–
35	borneol	1169	1174	–	–	–	–	0.2	–	–	0.2	–	–
36	terpinen-4-ol	1177	1178	–	0.2	–	–	–	–	0.1	0.2	–	0.2
37	p-cymen-8-ol	1179	1182	2.7	0.4	–	–	–	–	–	–	–	–
38	criptone	1185	1189	–	–	–	–	–	–	–	1.1	–	–
39	α-terpineol	1188	1191	3.3	0.7	1.6	0.7	2.3	0.5	0.7	0.5	30.9	2.2
40	phellandrene epoxide	–	1205	–	0.4	–	–	–	–	–	0.2	–	–
41	γ-terpineol	1199	1199	–	–	–	–	–	–	0.1	–	2.1	–
42	verbenone	1206	1209	0.6	0.1	0.2	–	0.6	–	–	–	–	–
43	(E)-ocimenone	1238	1239	–	–	–	–	0.4	–	–	–	–	–
44	cuminal	1241	1241	–	–	–	–	0.6	–	–	0.3	–	–
45	carvotanacetone	1247	1250	–	–	–	–	0.3	–	–	–	–	–
46	piperitone	1252	1255	–	0.4	–	–	–	–	–	–	–	–
47	trans-ascaridol glycol	1269	1273	–	–	–	–	0.7	–	–	0.2	–	–
48	carvacrol	1299	1305	–	0.1	–	–	–	–	–	–	–	–
49	p-vinyl-guaiacol	1309	1312	–	0.2	–	–	–	–	–	–	–	–
50	δ-elemene	1338	1339	–	–	–	–	–	–	0.1	–	–	–
51	α-cubebene	1351	1351	–	0.1	–	–	0.5	–	3.1	3.9	–	–
52	cyclosativene	1371	1370	–	–	–	–	–	–	1.5	1.3	–	–
53	α-ylangene	1375	1373	–	0.2	–	–	–	–	0.4	0.2	–	–
54	α-copaene	1376	1377	–	–	–	–	0.6	–	0.8	1.1	–	–
55	β-cubebene	1388	1391	0.5	0.1	–	–	–	–	0.5	0.5	–	–
56	iso-longifolene	1390	1389	–	–	–	–	–	–	0.3	0.3	–	–
57	β-elemene	1390	1393	–	0.1	–	–	–	–	–	0.3	–	–
58	cyperene	1398	1398	–	–	–	–	–	–	0.6	2.3	–	–
59	α-cedrene	1411	1414	–	–	–	–	–	–	1.7	1.6	–	–
60	α-cis-bergamotene	1412	1416	–	–	–	–	–	–	–	–	–	0.5
61	β-caryophyllene	1419	1423	–	–	–	–	–	–	2.7	–	–	–
62	β-cedrene	1420	1420	–	0.3	–	–	–	–	–	2.7	–	–
63	cis-thujopsene	1431	1433	–	–	–	–	–	–	0.7	0.5	–	–
64	trans-6-hydroxy-p-menth-1-en-3-one	–	1435	–	–	–	–	–	–	–	0.2	–	–
65	β-copaene	1432	1430	–	0.1	–	–	–	–	–	–	–	–
66	trans-α-bergamotene	1434	1437	–	0.1	–	–	–	–	3.2	2.6	–	–
67	β-humulene	1438	1440	–	0.02	–	–	0.2	–	–	–	–	–
68	α-guaiene	1439	1444	–	–	–	–	0.3	–	1.6	–	–	–
69	aromadendrene	1441	1448	–	–	–	–	–	–	2.0	–	–	–
70	β-barbatene	1442	1445	–	–	–	–	–	–	–	2.3	–	–
71	6,9-guaiadiene	1444	1444	–	0.3	–	0.5	–	–	–	–	–	–
72	cis-muurola-3,5-diene	1450	1450	–	0.1	–	–	–	–	–	–	–	–
73	α-neo-clovene	1454	1455	–	–	–	–	–	–	5.3	–	–	–
74	α-humulene	1454	1454	–	0.03	–	–	–	–	–	–	–	–
75	khusimene	1455	1454	–	–	–	–	–	–	–	2.9	–	–
76	sesquisabinene	1459	1461	–	–	–	–	–	–	1.0	1.0	–	–
77	allo-aromadendrene	1460	1461	–	0.03	–	–	–	–	–	–	–	–
78	cis-cadina-1(6),4-diene	1463	1465	–	–	–	–	–	–	1.8	0.2	–	–
79	α-acoradiene	1466	1469	–	–	–	–	–	–	–	0.5	–	–
80	α-neocallitropsene	1476	1481	–	–	–	–	–	–	7.3	–	–	–
81	γ-gurjunene	1477	1480	–	–	–	–	–	–	–	5.2	–	–
82	γ-muurolene	1479	1478	–	0.1	–	–	0.2	–	0.8	–	–	–
83	α-curcumene	1480	1486	–	–	–	–	–	–	–	0.6	–	–
84	germacrene D	1481	1482	–	0.8	–	–	–	–	–	–	–	–
85	α-amorphene	1484	1490	–	0.1	–	–	–	–	–	–	–	–
86	trans-muurola-4(14), 5-diene	1490	1483	–	–	–	–	–	–	–	0.2	–	–
87	cis-β-guaiene	1493	1496	–	–	–	–	–	–	2.3	–	–	–
88	epi-cubebol	1494	1497	–	–	–	–	–	–	–	0.2	–	–
89	valencene	1496	1503	–	–	–	–	–	–	1.7	–	–	–
90	α-selinene	1498	1501	–	–	–	–	–	–	–	0.3	–	–
91	trans-β-guaiene	1502	1513	–	–	–	–	–	–	4.9	–	–	–
92	cuparene	1504	1509	–	–	–	–	–	–	–	1.8	–	–
93	δ-amorphene	1512	1508	–	0.3	–	–	–	–	–	–	–	–
94	γ-cadinene	1513	1515	0.5	0.1	–	–	0.1	–	14.4	9.5	–	–
95	trans-calamenene	1522	1525	–	–	–	–	0.4	–	–	–	–	–
96	δ-cadinene	1523	1525	–	0.1	–	–	–	–	4.4	4.3	–	–
97	kessane	1530	1533	–	–	–	–	–	–	–	0.4	–	–
98	(E)-γ-bisabolene	1531	1533	–	–	–	–	–	–	–	–	–	1.1
99	trans-cadina-1,4-diene	1534	1541	–	–	–	–	–	–	3.6	–	–	–
100	α-cadinene	1538	1541	–	–		–	–	–	0.9	0.5	–	–
101	α-calacorene	1545	1546	–	0.04	–	–	–	–	0.9	0.7	–	–
102	timohydroquinone	1555	1565	–	–	–	–	0.1	–	–	–	–	–
103	germacrene B	1561	1569	–	–	–	–	–	–	0.6	–	–	–
104	β-calacorene	1565	1567	–	–	–	–	–	–	–	0.4	–	–
105	caryophyllene oxide	1583	1585	–	–	–	–	0.2	–	0.4	3.3	–	–
106	salvial-4(14)-en-1-one	1594	1595	–	0.03	–	–	0.1	–	–	–	–	–
107	rosifoliol	1600	1598	–	–	–	–	–	–	0.2	–	–	–
108	5-epi-7-epi-α-eudesmol	1607	1611	–	–	–	–	–	–	0.1	–	–	–
109	humulene epoxide II	1608	1613	–	–	–	–	–	–	–	0.7	–	–
110	junenol	1619	1620	–	0.1	–	–	0.6	–	–	–	–	–
111	1,10-di-epi-cubenol	1619	1620	–	–	–	–	–	–	3.5	2.4	–	–
112	dillapiol	1620	1627	–	0.1	–	–	–	–	–	–	–	–
113	1-epi-cubenol	1628	1632	–	–	–	–	–	–	0.1	–	–	–
114	epi-α-cadinol	1640	1642	1.2	0.1	–	–	0.1	–	0.3	0.2	–	–
115	cis-calamenen-10-ol	1661	1663	–	–	–	–	–	–	–	0.4	–	–
116	trans-calamenen-10-ol	1669	1672	–	–	–	–	–	–	–	0.3	–	–
117	bulnesol	1671	1671	–	–	–	–	–	–	0.2	–	–	–
118	cadalene	1676	1677	–	–	–	–	–	–	0.1	0.4	–	–
119	α-bisabolol	1685	1686	–	–	–	–	–	–	0.2	–	–	–
120	5-neo-cedranol	1685	1687	–	–	–	–	–	–	–	0.2	–	–
121	eudesma-4(15),7-dien-1β-ol	1688	1689	–	–	–	–	0.1	–	–	–	–	–
122	cis-14-nor-muurol-5-en-4-one	1689	1691	–	–	–	–	–	–	–	0.5	–	–
123	davanol acetate	1689	1695	–	–	–	–	–	–	–	0.2	–	–
124	10-nor-calamenen-10-one	1702	1705	–	–	–	–	–	–	–	0.3	–	–
	Total identified components (%)	–	–	99.0	97.0	98.7	98.0	61.9	100	98.0	84.5	98.8	99.9
	Monoterpenes hydrocarbons	–	–	87.7	89.9	93.2	96.8	51.2	99.0	20.4	21.1	62.5	94.5
	Oxigenated monoterpenes	–	–	9.0	3.8	5.5	0.7	7.2	1.0	3.4	6.0	36.3	3.8
	Sesquiterpenes hydrocarbons	–	–	1.0	3.0	–	0.5	2.3	–	69.1	48.1	–	1.6
	Oxygenated sesquiterpenes	–	–	1.2	0.3	–	–	1.2	–	5.1	9.3	–	–

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[1] * Corresponding author. E-mail:sgleitao@pharma.ufrj.br (S.G. Leitão).