Insecticidal activity of <i>Piper aduncum</i> oil: variation in dillapiole content and chemical and toxicological stability during storage

FAZOLIN, Murilo; MONTEIRO, André Fabio Medeiros; BIZZO, Humberto Ribeiro; GAMA, Paola Ervatti; VIANA, Luana de Oliveira; LIMA, Maria Érica Costa de

doi:10.1590/1809-4392202102292

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Agronomy and Forestry • Acta Amaz. 52 (3) • Jul-Sep 2022 • https://doi.org/10.1590/1809-4392202102292 copy

Insecticidal activity of Piper aduncum oil: variation in dillapiole content and chemical and toxicological stability during storage

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

The insecticidal effect of the essential oil of Piper aduncum (EOPA), and of its constituent dillapiole [1-allyl-2,3-dimethoxy-4,5-(methylenedioxy) benzene] in particular, is well documented in the literature and can be associated with its interference with the enzymatic detoxification in arthropods. However, no data exist on the range of dillapiole content associated with insecticidal activity, which is necessary to establish reliable dose-activity parameters for a formulated product. The oil composition can also change during storage after distillation, mainly due to environmental factors such as light incidence, atmospheric oxygen and temperature, which can be deleterious to oil quality. In this study, EOPA subjected to different storage conditions over four years and its rectified fractions were submitted to bioassays to evaluate their insecticidal effect by topical contact and residual contact against Spodoptera frugiperda. Our objectives were to determine the relationship between dillapiole content and the insecticidal activity of EOPA, and to evaluate its chemical and toxicological properties over time under different conditions. Our results showed that EOPA was stable with respect to the dillapiole content and the toxicological effect against S. frugiperda under different storage conditions for four years. The overall chemical composition of the EOPA did not vary significantly among storage conditions. EOPA with dillapiole content ranging between 68% and 100% showed greater insecticidal toxicity by residual and topical contact against S. frugiperda larvae.

Keywords:
chemical and toxicological stability; arylpropanoids; botanical insecticides; terpenoid storage; 1-allyl-2,3-dimethoxy-4,5-(methylenedioxy) benzene

Treatment	Code
UV chamber, amber flask	UVCA
UV chamber, colorless flask	UVCC
Indoors, amber flask	INAF
Indoors, colorless flask	INCF
Refrigerator, amber flask	REFA
Refrigerator, colorless flask	REFC
Direct sunlight exposition, amber flask	SUNA
Direct sunlight exposition, colorless flask	SUNC
Control (refrigerator, amber flask covered with aluminium foil)	CONT

Peak	LRI_calc	LRI_lit	Identified compounds	Time (days)*
Peak	LRI_calc	LRI_lit	Identified compounds	0	360	720	1080	1440
1	932	932	α-pinene	0.7	0.7	0.6	0.5	0.1
2	976	974	β-pinene	1.2	1.2	1.2	1.1	0.5
3	1005	1002	α-phellandrene	0.4	0.4	0.3	0.3	0.2
4	1022	1020	p-cymene	tr	0.1	tr	tr	0.1
5	1026	1024	limonene	tr	0.3	0.2	0.2	0.2
6	1035	1032	(Z)-β-ocimene	tr	tr	tr	tr	0.1
7	1046	1044	(E)-β-ocimene	0.5	tr	tr	tr	0.3
8	1345	1345	α-cubebene	tr	tr	tr	tr	tr
9	1362	1369	cyclosativene	tr	tr	0.2	0.2	0.2
10	1374	1374	α-copaene	1.0	1.1	1.1	1.1	1.1
11	1389	1389	β-elemene	tr	tr	0.1	0.1	0.3
12	1404	1409	α-gurjunene	tr	tr	tr	tr	0.1
13	1415	1417	(E)-caryophyllene	8.0	9.0	9.1	9.1	8.9
14	1423	1430	β-copaene	tr	tr	tr	tr	0.1
15	1433	1439	aromadendrene	tr	tr	tr	tr	0.3
16	1448	1449	α-humulene	1.0	1.1	1.2	1.1	1.1
17	1455	1457	β-santalene	tr	0.5	0.5	0.5	0.5
18	1472	1477	γ-muurolene	tr	tr	tr	tr	0.1
19	1479	1480	germacrene D	0.9	1.1	1.1	1.0	1.0
20	1486	1489	β-selinene	tr	tr	tr	tr	0.2
21	1490	1493	(E)-muurola-4(14),5-diene	tr	tr	tr	tr	0.1
22	1494	1494	bicyclogermacrene	1.0	1.1	1.1	1.1	1.0
23	1497	1500	pentadecane	1.7	1.7	1.7	1.7	1.8
24	1506	1511	δ-amorphene	0.5	0.4	0.4	0.4	0.3
25	1515	1514	cubebol	0.8	0.8	0.8	0.5	0.6
26	1519	1517	myristicin	2.4	2.6	2.1	2.0	2.5
27	1528	1533	(E)-cadina-1,4-diene	tr	tr	tr	tr	0.2
28	1538	1544	α-calacorene	tr	tr	tr	0.3	0.3
29	1556	1555	elemicin	tr	tr	tr	tr	0.4
30	1561	1561	(E)-nerolidol	tr	0.4	0.4	0.4	0.6
31	1573	1577	spathulenol	tr	0.4	0.5	0.6	0.5
32	1578	1582	caryophyllene oxide	1.0	1.2	1.3	1.3	1.4
33	1586	1592	viridiflorol	0.8	0.9	0.9	0.9	0.9
34	1604	1608	humulene epoxide II	tr	tr	tr	tr	0.1
35	1619	1620	dillapiole	78.0	74.1	74.8	75.7	73.5
36	1677	1677	apiole	tr	tr	tr	tr	0.2
			Total	99.9	99.1	99.6	100.0	99.7
			Monoterpenes	2.8	2.7	2.3	2.1	1.5
			Oxygenated monoterpenoids	0.0	0.0	0.0	0.0	0.0
			Sesquiterpenes	13.2	14.3	15.6	15.4	16.3
			Oxygenated sesquiterpenoids	1.8	3.3	2.6	2.6	3.0
			Arylpropanoids	80.4	76.7	76.9	77.7	76.6
			Others	1.7	1.7	1.7	1.7	1.8

Peak	LRI_calc	LRI_lit	Identification	UVCA	UVCC	INAF	INCF	REFA	REFC	SUNA	SUNC	CONT
1	932	932	α-pinene	tr	tr	tr	tr	tr	tr	tr	tr	0.1
2	976	974	β-pinene	tr	0.1	tr	tr	tr	0.2	0.1	0.1	0.5
3	1005	1002	α-phellandrene	tr	0.2	tr	tr	0.1	0.1	tr	tr	0.2
4	1022	1020	p-cymene	tr	tr	tr	tr	tr	0.1	tr	tr	0.1
5	1026	1024	limonene	tr	tr	tr	tr	0.1	0.1	tr	tr	0.1
6	1035	1032	(Z)-β-ocimene	tr	tr	tr	tr	0.1	0.1	tr	tr	0.1
7	1046	1044	(E)-β-ocimene	tr	tr	tr	tr	0.2	0.2	tr	tr	0.3
8	1100	1100	linalool	tr	tr	tr	tr	0.1	tr	tr	tr	tr
9	1345	1345	α-cubebene	tr	0.1	tr	0.1	0.1	0.1	0.1	0.1	tr
10	1362	1369	cyclosativene	0.1	tr	0.1	0.1	0.2	0.2	0.1	0.1	0.2
11	1374	1374	α-copaene	0.4	0.5	0.7	0.7	1.1	1.1	0.6	0.8	1.1
12	1380	1387	β-bourbonene	tr	tr	tr	tr	tr	tr	tr	0.3	tr
13	1386	1387	β-cubebene	tr	tr	tr	tr	0.1	0.1	tr	tr	0.1
14	1389	1389	β-elemene	0.1	0.1	0.3	0.2	0.2	0.3	0.2	0.2	0.3
15	1404	1409	α-gurjunene	tr	tr	tr	tr	0.1	0.1	tr	tr	0.1
16	1409	1408	(Z)-caryophyllene	tr	tr	tr	tr	tr	tr	tr	0.1	tr
17	1415	1417	(E)-caryophyllene	4.9	4.1	6.6	6.6	8.7	8.9	5.1	2.2	8.9
18	1423	1430	β-copaene	0.1	tr	0.1	0.1	0.1	0.1	0.1	0.1	0.1
19	1433	1439	aromadendrene	0.2	tr	0.2	0.2	0.3	0.3	0.2	0.3	0.3
20	1448	1449	α-humulene	0.8	0.7	1.0	1.0	1.1	1.2	0.8	0.6	1.1
21	1455	1457	β-santalene	0.3	0.3	0.4	0.4	0.5	0.5	0.4	0.4	0.5
22	1470	1475	(E)-cadina-1(6),4-diene	tr	tr	0.1	tr	tr	tr	0.1	tr	tr
23	1472	1477	γ-muurolene	0.1	tr	tr	0.1	0.1	0.1	tr	0.1	0.1
24	1479	1480	germacrene D	0.6	tr	0.7	0.7	1.0	1.0	0.3	tr	1.0
25	1480	1482	ar-curcumene	0.2	0.3	0.1	0.2	0.1	tr	0.2	0.3	tr
26	1486	1489	β-selinene	tr	tr	0.1	tr	0.1	0.2	tr	tr	0.2
27	1490	1493	(E)-muurola-4(14),5-diene	0.1	tr	0.1	tr	0.1	0.1	tr	tr	0.1
28	1493	1494	epi-cubebol	0.7	0.2	0.2	0.7	0.4	-	0.1	0.3	-
29	1494	1494	bicyclogermacrene	tr	tr	0.5	tr	0.6	1.0	0.3	tr	1.0
30	1497	1500	pentadecane	1.2	1.2	1.4	1.5	1.8	1.8	1.1	1.4	1.8
31	1502	1511	δ-amorphene	0.2	0.1	0.1	0.2	0.3	0.3	0.1	tr	0.3
32	1513	1514	β-curcumene	tr	tr	tr	tr	0.2	0.2	tr	tr	0.2
33	1515	1514	cubebol	0.2	0.2	0.5	0.5	0.6	0.6	0.4	0.3	0.6
34	1519	1517	myristicin	2.5	2.6	2.6	2.6	2.5	2.5	2.5	2.4	2.5
35	1528	1533	(E)-cadina-1,4-diene	0.1	tr	0.1	0.1	0.2	0.2	tr	tr	0.2
36	1538	1544	α-calacorene	0.3	0.3	0.3	0.3	0.3	0.3	0.3	0.2	0.3
37	1556	1555	elemicin	0.5	0.4	0.4	0.5	0.4	0.4	0.4	0.3	0.4
38	1561	1561	(E)-nerolidol	0.6	0.6	0.3	0.6	0.6	0.6	0.6	0.6	0.6
39	1573	1577	spathulenol	0.8	0.9	0.7	0.8	0.5	0.5	1.0	0.9	0.5
40	1578	1582	caryophyllene oxide	1.7	2.5	1.6	1.7	1.3	1.4	2.3	3.2	1.4
41	1586	1592	viridiflorol	0.9	0.9	0.9	0.9	0.9	0.9	0.9	1.2	0.9
42	1600	1600	ledol	0.2	tr	tr	0.2	0.1	tr	tr	0.2	tr
43	1604	1608	humulene epoxyde II	0.2	0.3	0.2	tr	0.1	0.1	0.3	0.5	0.1
44	1619	1620	dillapiole	81.6	82.4	78.8	78.8	74.3	73.9	80.5	80.2	73.5
45	1643	1644	α-muurolol	tr	tr	0.1	0.1	0.1	0.1	0.1	0.1	tr
46	1650	1652	α-cadinol	0.1	tr	tr	tr	tr	tr	tr	tr	tr
47	1660	1660	cis-calamenen-10-ol	0.1	tr	tr	tr	tr	tr	tr	tr	tr
48	1668	1668	trans-calamenen-10-ol	tr	0.7	tr	tr	tr	tr	tr	tr	tr
49	1677	1677	apiole	0.2	0.2	0.2	0.2	0.2	0.2	0.2	0.2	0.2
			Total:	99.9	99.9	99.3	99.9	99.5	99.8	99.2	97.6	99.9
			Monoterpenes:	0.0	0.3	0.0	0.0	0.4	0.7	0.1	0.1	1.4
			Oxygenated monoterpenoids:	0.0	0.0	0.0	0.0	0.1	0.0	0.0	0.0	0.0
			Sesquiterpenes:	8.5	6.5	11.4	10.8	15.3	16.2	8.7	5.8	16.0
			Oxygenated sesquiterpenoids:	5.4	6.3	4.5	5.5	4.6	4.2	5.7	7.2	4.1
			Others:	86.0	86.8	83.4	83.6	79.2	78.8	84.7	84.5	78.4

Peak	LRIcalc	LRIlit	Identification	UVCA	UVCC	INAF	INCF	REFA	REFC	SUNA	SUNC	CONT
1	932	932	α-pinene	0.5	0.4	0.5	0.4	0.6	0.6	0.3	0.4	0.7
2	976	974	β-pinene	1.0	0.9	1.0	0.9	1.2	1.2	0.6	0.8	1.2
3	1005	1002	α-phellandrene	0.2	0.2	0.2	0.2	0.3	0.3	0.1	tr	0.4
4	1023	1020	p-cymene	0.1	0.1	0.1	0.1	tr	tr	tr	tr	0.1
5	1027	1024	limonene	0.2	0.2	0.2	0.2	0.4	0.3	0.1	tr	0.3
6	1036	1032	(Z)-β-ocimene	0.2	0.1	0.2	0.2	0.2	0.2	tr	tr	0.3
7	1046	1044	(E)-β-ocimene	0.4	0.3	0.4	0.3	0.5	0.5	0.2	tr	0.6
8	1365	1369	cyclosativene	0.2	tr	0.2	0.2	tr	tr	0.2	tr	tr
9	1374	1374	α-copaene	1.1	1.1	1.1	1.1	1.1	1.1	1.1	1.1	1.1
9A	1383	1387	β-bourbonene	tr	tr	tr	tr	tr	tr	tr	0.4	tr
10	1391	1389	β-elemene	0.1	0.1	0.1	0.1	tr	tr	0.2	0.2	tr
11	1418	1417	(E)-caryophyllene	8.6	8.4	8.5	8.6	8.9	9.0	8.5	8.1	9.0
12	1436	1439	α-trans-bergamotene + aromadendrene	0.3	tr	0.3	0.3	tr	tr	tr	tr	tr
13	1451	1452	α-humulene	1.1	1.1	1.1	1.1	1.1	1.1	1.1	1.1	1.1
14	1459	1457	β-santalene	0.5	0.5	0.5	0.5	0.5	0.5	0.5	0.4	0.5
15	1479	1459	allo-aromadendrene	0.9	0.7	0.9	0.9	1.0	1.1	0.8	tr	1.1
16	1494	1494	epi-cubebol + bicyclogermacrene	0.9	0.8	0.9	0.9	1.1	1.1	0.9	0.8	1.1
17	1500	1500	pentadecane	1.7	1.7	1.7	1.8	1.7	1.7	1.9	1.9	1.7
18	1506	1511	δ-amorphene	0.3	0.2	0.2	0.2	0.4	0.4	0.2	tr	0.4
19	1514	1514	cubebol	0.8	0.8	0.7	0.8	0.8	0.8	0.8	0.8	0.8
20	1522	1522	miristicin + δ-cadinene	2.6	2.6	2.6	2.6	2.6	2.6	2.7	2.6	2.6
21	1541	1544	α-calacorene	0.3	tr	0.3	0.3	tr	tr	0.3	tr	tr
22	1559	1555	elemicin	0.2	0.2	0.2	0.2	tr	tr	0.2	tr	tr
23	1564	1561	(E)-nerolidol	0.4	0.4	0.4	0.4	0.4	0.4	0.4	0.4	0.4
24	1576	1577	spathulenol	0.7	0.7	0.6	0.7	0.4	0.5	0.7	0.7	0.4
25	1581	1582	caryophyllene oxide	1.5	1.7	1.5	1.6	1.2	1.2	1.7	1.9	1.2
26	1589	1592	viridiflorol	0.9	0.9	0.9	0.9	0.9	0.9	0.9	0.9	0.9
27	1607	1608	humulene epoxyde II	0.2	tr	0.2	0.2	tr	tr	tr	tr	tr
28	1632	1620	dillapiole	74.2	75.8	74.4	74.7	74.5	74.5	75.8	77.5	74.1
			Total	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0
			Monoterpenes	2.7	2.2	2.7	2.2	3.3	3.2	1.4	1.2	3.5
			Oxygenated monoterpenoids	0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0
			Sesquiterpenes	14.3	12.9	14.1	14.1	14.2	14.2	13.7	12.1	14.4
			Oxygenated sesquiterpenoids	4.4	4.5	4.4	4.5	3.7	3.7	4.5	4.7	3.7
			Others	78.7	80.3	78.9	79.3	78.8	78.8	80.4	82.0	78.5

Peak	LRIcalc	LRIlit	Identification	UVCA	UVCC	INAF	INCF	REFA	REFC	SUNA	SUNC	CONT
1	932	932	α-pinene	tr	0.1	0.1	0.2	0.6	0.5	tr	tr	0.6
2	975	974	β-pinene	0.2	0.3	0.4	0.5	1.1	1.0	0.1	0.1	1.2
3	1004	1002	α-phellandrene	tr	tr	tr	tr	0.3	0.3	tr	tr	0.3
4	1022	1020	p-cymene	tr	tr	tr	tr	0.1	0.1	tr	tr
5	1026	1024	limonene	tr	tr	tr	tr	0.2	0.2	tr	tr	0.2
6	1035	1032	(Z)-β-ocimene	tr	tr	tr	tr	0.2	0.2	tr	tr	0.2
7	1045	1044	(E)-β-ocimene	tr	tr	tr	tr	0.4	0.3	tr	tr	0.3
8	1345	1345	α-cubebene	tr	tr	tr	tr	tr	tr	tr	0.1	tr
9	1362	1369	cyclosativene	tr	tr	tr	0.2	0.2	0.2	0.1	0.1	0.2
10	1371	1374	α-copaene	0.7	0.8	1.0	1.0	1.1	1.1	0.9	0.9	1.1
11	1379	1387	β-bourbonene	tr	tr	tr	tr	tr	tr	tr	0.3	tr
12	1388	1389	β-elemene	tr	tr	0.1	0.2	0.3	0.3	0.2	0.2	0.1
13	1414	1417	(E)-caryophyllene	6.9	6.8	8.3	8.2	8.9	8.9	7.5	4.4	9.1
14	1423	1430	β-copaene	tr	tr	tr	tr	0.1	0.1	tr	0.2	tr
15	1433	1432	trans-α-bergamotene	tr	tr	tr	0.3	0.3	0.3	tr	0.3	tr
16	1448	1452	α-humulene	1.0	1.0	1.1	1.1	1.1	1.1	1.0	0.8	1.2
17	1455	1457	β-santalene	tr	0.4	0.4	0.4	0.5	0.5	0.4	0.4	0.5
18	1475	1484	germacrene D	0.8	0.5	0.9	0.8	1.0	1.0	0.6	tr	1.1
19	1479	1479	ar-curcumene	tr	tr	tr	tr	tr	tr	tr	0.2	tr
20	1491	1494	bicyclogermacrene	tr	0.6	0.9	0.8	1.1	1.1	0.1	0.4	1.1
21	1496	1500	pentadecane	1.2	1.5	1.5	1.7	1.6	1.6	1.5	1.6	1.7
22	1502	1511	δ-amorphene	tr	tr	0.2	0.1	0.4	0.4	tr	tr	0.4
23	1510	1513	γ-cadiene	0.7	0.7	0.8	0.8	0.8	0.8	0.7	0.5	0.8
24	1518	1517	miristicin	1.8	2.1	2.2	2.3	2.3	2.3	2.3	2.4	2.1
25	1527	1533	trans-cadina-1,4-diene	tr	tr	tr	tr	0.1	tr	tr	tr	tr
26	1537	1544	α-calacorene	tr	tr	0.3	0.3	0.3	0.3	0.3	0.2	tr
27	1546		n.i.	tr	tr	tr	tr	tr	tr	tr	0.2	tr
28	1555	1555	elemicin	tr	tr	tr	0.1	0.1	0.1	tr	0.2	tr
29	1560	1561	(E)-nerolidol	tr	0.4	0.4	0.5	0.4	0.4	0.4	0.5	0.4
30	1572	1577	spathulenol	0.7	0.8	0.7	0.8	0.6	0.6	0.9	1.0	0.5
31	1577	1582	caryophyllene oxide	1.7	2.1	1.6	1.7	1.3	1.3	2.1	3.3	1.3
32	1585	1592	viridiflorol	1.0	1.0	0.9	0.9	0.9	0.9	1.0	1.0	0.9
33	1603	1608	humulene epoxyde II	tr	tr	tr	0.2	0.1	0.2	0.2	0.4	tr
34	1618	1620	dillapiole	83.3	80.8	78.1	76.8	73.6	74.2	79.2	80.2	74.8
35	1655		n.i.	tr	tr	tr	tr	tr	tr	tr	tr	tr
36	1666		n.i.	tr	tr	tr	tr	tr	tr	tr	0.2	tr
37	1994		n.i.	tr	tr	tr	tr	tr	tr	0.3	tr	tr
38	2014		n.i.	tr	tr	tr	tr	tr	tr	tr	tr	tr
			total	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0
			Monoterpenes	0.0	0.4	0.5	0.7	2.9	2.5	0.1	0.1	2.8
			Oxygenated monoterpenoids	0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0
			Sesquiterpenes	10.1	10.8	14.1	14.2	16.2	16.0	12.0	9.0	15.5
			Oxygenated sesquiterpenoids	3.4	4.3	3.6	4.1	3.3	3.3	4.5	6.2	3.0
			Others	86.3	84.4	81.8	81.0	77.6	78.2	83.1	84.5	78.7

Peak	LRIcalc	LRIlit	Identification	UVCA	UVCC	INAF	INCF	REFA	REFC	SUNA	SUNC	CONT
1	931	932	α-pinene	0.0	0.0	0.0	0.0	0.6	0.5	tr	tr	0.5
2	946	946	canphene	tr	tr	tr	tr	0.0	tr	tr	tr	tr
3	975	974	β-pinene	0.1	0.1	0.1	0.1	1.1	1.1	tr	tr	1.1
4	1004	1002	α-phellandrene	tr	tr	tr	tr	0.3	0.3	tr	tr	0.3
5	1023	1020	p-cymene	tr	tr	tr	tr	0.1	0.1	tr	tr	tr
6	1026	1024	limonene	tr	tr	tr	tr	0.3	0.2	tr	tr	0.2
7	1035	1032	(Z)-β-ocimene	tr	tr	tr	tr	0.2	0.2	tr	tr	tr
8	1045	1044	(E)-β-ocimene	tr	tr	tr	tr	0.3	0.3	tr	tr	tr
9	1345	1345	α-cubebene	tr	0.1	tr	tr	0.1	tr	0.1	0.1	tr
10	1362	1369	cyclosativene	0.1	0.1	0.1	0.1	0.2	0.2	0.1	0.1	0.2
11	1371	1374	α-copaene	0.6	0.6	0.9	0.9	1.1	1.1	0.7	0.9	1.1
12	1380	1387	β-bourbonene	tr	tr	tr	tr	tr	tr	tr	0.3	tr
13	1386	1387	β-cubebene	0.1	tr	0.1	tr	0.1	0.1	tr	tr	tr
14	1388	1389	β-elemene	0.2	0.1	0.2	0.2	0.2	0.2	0.2	0.2	0.1
15	1404	1409	α-gurjunene	tr	tr	tr	tr	0.1	tr	tr	0.1	tr
16	1415	1417	(E)-caryophyllene	5.9	5.2	7.7	7.3	8.9	8.9	6.2	2.7	9.1
17	1424	1430	β-copaene	0.1	0.1	0.1	0.1	0.1	0.1	0.1	0.2	tr
18	1432	1432	trans-α-trans-bergamotene	tr	tr	tr	tr	0.1	tr	tr	tr	tr
19	1433	1439	aromadendrene	0.2	0.2	0.3	0.3	0.2	0.3	0.2	0.3	tr
20	1448	1452	α-humulene	0.9	0.8	1.0	1.0	1.1	1.1	0.9	0.6	1.1
21	1455	1457	β-santalene	0.4	0.4	0.4	0.4	0.5	0.5	0.4	0.4	0.5
22	1472	1478	γ-muroleno	0.1	0.1	0.1	0.1	0.1	0.1	0.1	tr	tr
23	1476	1484	germacrene D	0.7	0.3	0.8	0.7	1.0	1.0	0.4	tr	1.0
24	1480	1479	ar-curcumene	0.1	tr	0.1	0.2	tr	tr	0.2	0.3	tr
25	1486	1493	trans-muurola-4-(14), 5-diene	0.1	0.2	0.1	tr	0.1	tr	tr	tr	tr
26	1491	1494	bicyclogermacrene	0.7	0.5	0.8	0.7	1.1	1.0	0.5	0.4	1.1
27	1497	1500	pentadecane	1.3	1.3	1.5	1.5	1.6	1.6	1.2	1.5	1.7
28	1502	1511	δ-amorphene	0.1	tr	0.1	tr	0.4	0.4	tr	tr	0.4
29	1505	1505	α-(E,E)-farnesene	tr	tr	tr	tr	0.1	tr	tr	tr	tr
30	1509		n.i.	0.2	tr	0.1	tr	0.2	0.2	tr	tr	tr
31	1511	1513	γ-cadinene	0.6	0.6	0.6	0.7	0.6	0.6	0.7	0.6	0.5
32	1519	1517	miristicin	2.3	2.3	2.4	2.3	2.3	2.1	2.3	2.1	2.0
33	1528	1533	trans-cadina 1,4 diene	0.1	tr	0.1	0.1	0.1	0.1	tr	tr	tr
34	1538	1544	α-calacorene	0.3	0.3	0.3	0.3	0.3	0.3	0.3	tr	0.3
35	1551	1559	germacrene B	0.1	0.1	0.1	0.1	0.1	0.1	0.3	0.2	tr
36	1556	1555	elemicin	0.1	0.1	0.1	0.2	0.3	0.1	0.2	0.2	tr
37	1561	1561	(E)-nerolidol	0.4	0.5	0.4	0.6	0.5	0.4	0.6	0.5	0.4
38	1573	1577	spathulenol	0.8	0.9	0.7	0.8	0.5	0.6	0.9	0.9	0.6
39	1578	1582	caryophyllene oxide	1.6	2.2	1.6	1.7	1.3	1.3	2.2	3.4	1.3
40	1586		n.i.	0.9	0.9	0.9	0.9	0.8	0.9	0.9	1.2	0.9
41	1597		n.i.	0.2	0.1	0.2	tr	0.2	tr	0.2	0.2	tr
42	1603	1608	humulene epoxyde II	0.2	0.2	0.2	0.2	0.1	0.1	0.2	0.5	tr
43	1607		n.i.	0.1	tr	tr	tr	tr	tr	tr	tr	tr
44	1619	1620	dillapiole	80.5	81.6	77.6	78.5	72.7	74.0	79.8	82.0	75.7
45	1644		n.i.	0.1	0.1	0.1	tr	0.1	tr	0.1	tr	tr
			Total	98.5	96.8	98.7	99.1	98.8	99.0	98.8	98.6	99.1
			Monoterpenes	0.2	0.2	0.2	0.2	2.9	2.6	0.0	0.0	2.1
			Otrygenated monoterpenoids	0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0	0.0
			Sesquiterpenes	11.2	9.5	14.1	13.2	16.6	16.1	11.4	7.5	15.3
			Otrygenated sesquiterpenoids	3.0	3.8	2.9	3.2	2.5	2.4	3.9	5.3	2.3
			Others	85.6	86.5	82.9	83.4	78.1	78.8	84.7	87.2	80.3

Instituto Nacional de Pesquisas da Amazônia Av. André Araujo, 2936 Aleixo, 69060-001 Manaus AM Brasil, Tel.: +55 92 3643-3030, Fax: +55 92 643-3223 - Manaus - AM - Brazil
E-mail: acta@inpa.gov.br

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[1] *Corresponding author: murilo.fazolin@embrapa.br