Secondary Metabolite Profile, Antioxidant Capacity, and Mosquito Repellent Activity of Bixa orellana from Brazilian Amazon Region

Table 4

Identification of volatile organic compounds (VOCs) by HS-SME-GC/MS from headspace of B. orellana plant extracts obtained from different plant parts and from the headspace in living plant fruits (in vivo sampling).

RI^a	Volatile compounds	Seed^b		Wood^b		Leaf^b		Bark^b		Fruit^b		“In vivo”^c
		𝑛=5	s.d.	𝑛=5	s.d.	𝑛=5	s.d.	𝑛=5	s.d.	𝑛=5	s.d.	𝑛=5	s.d.
	Free fatty acids
1285	Acetic acid	0.03	0.02	nd	—	0.01	—	nd	—	nd	—	nd	—
1628	2-ethylhexanoic acid	nd	—	nd	—	nd	—	nd	—	nd	—	0.12	0.01
	Total	0.03		—	—	0.01		—	—	—	—	0.12
	Alcohols
659	Ethanol	1.18	0.03	nd	—	nd	—	0.02		1.06	0.03	nd	—
848	2-methyl-1-propanol	0.01	—	nd	—	nd	—	nd	—	0.03	—	nd	—
919	2-pentanol	nd	—	nd	—	nd	—	nd	—	0.01	—	nd	—
976	1-penten-3-olo	nd	—	nd	—	nd	—	nd	—	0.01	—	nd	—
1040	2-methyl-1-butanol	0.13	0.05	nd	—	nd	—	nd	—	0.05	—	nd	—
1175	3-methyl-2-buten-1-ol	0.01		nd	—	nd	—	nd	—	nd	—	nd	—
1573	2-methoxyphenol	0.06		nd	—	nd	—	nd	—	nd	—	nd	—
1650	Phenol	0.01		nd	—	nd	—	nd	—	nd	—	nd	—
	Total	1.39		—	—	—	—	0.02		1.16		—	—
	Aldehydes
645	2-methyl-butanal	nd	—	nd	—	0.01		nd	—	nd	—	nd	—
648	3-methyl-butanal	nd	—	nd	—	0.01		nd	—	nd	—	nd	—
687	Pentanal	nd	—	nd	—	0.03		nd	—	nd	—	nd	—
815	Hexanal	nd	—	nd	—	0.01		nd	—	nd	—	0.12	0.01
1034	2-hexenal	nd	—	nd	—	0.01		nd	—	nd	—	nd	—
1243	Nonanal	nd	—	nd	—	nd	—	nd	—	nd	—	0.17	0.02
1332	Decanal	nd	—	nd	—	nd	—	nd	—	nd	—	0.17	0.03
1341	Benzaldehyde	nd	—	2.20	0.04	nd	—	nd	—	nd	—	0.10	—
	Total	—	—	2.20		0.07		—	—	—	—	0.56
	Ketones
614	2-propanone	nd	—	nd	—	0.02		nd	—	nd	—	0.09	0.01
654	2-methyl-3-butanone	nd	—	0.71	0.01	nd	—	nd	—	nd	—	nd	—
685	3-pentanone	nd	—	2.50	0.02	nd	—	nd	—	0.07		nd	—
701	2-methyl-3-pentanone	nd	—	4.09	0.17	nd	—	nd	—	nd	—	nd	—
712	4-methyl-2-pentanone	nd	—	nd	—	nd	—	nd	—	nd	—	0.29	0.03
852	1,2-cycloctandione	0.01		nd	—	nd	—	nd	—	nd	—	nd	—
984	2-heptanone	nd	—	nd	—	nd	—	nd	—	0.01		nd	—
1121	3-hydroxy-2-butanone	nd	—	0.69	0.03	nd	—	nd	—	nd	—	nd	—
1189	6-methyl-5-hepten-2-one	0.02		nd	—	0.01		nd	—	nd	—	0.14	0.02
1422	4-tert-butylcyclohexanone	nd	—	nd	—	nd	—	nd	—	nd	—	0.50	0.06
	Total	0.03		7.99		0.03		—	—	0.08		1.03
	Sulphur compounds
604	Dimethyl sulfide	0.25	0.02	nd	—	nd	—	0.01	—	0.31	0.02	nd	—
	Total	0.25	—	—		—		0.01		0.31		—	—
	Furans
639	2-methylfuran	0.02		2.71	0.15	0.01	—	0.01	—	nd	—	nd	—
671	2-ethylfuran	nd	—	nd	—	0.01	—	nd	—	nd	—	nd	—
	Total	0.02		2.71		0.02		0.01		—		—
	Esters
618	Methyl acetate	0.01	—	nd	—	nd	—	nd	—	nd	—	nd	—
636	Ethyl acetate	0.51	0.12	nd	—	nd	—	nd	—	nd	—	nd	—
895	2-methyl-1-butanol acetate	0.03	—	nd	—	nd	—	nd	—	nd	—	nd	—
898	3-methyl-1-butanol ecetate	0.02	—	nd	—	nd	—	nd	—	nd	—	nd	—
	Total	0.57		—		—		—		—		—
	Hydrocarbons
746	Toluene	nd	—	nd	—	0.01		nd	—	nd	—	nd	—
884	Ethylbenzene	nd	—	2.24	0.06	nd	—	nd	—	nd	—	2.72	0.03
894	o-xylene	nd	—	nd	—	nd	—	nd	—	0.01		0.70	0.03
909	p-xylene	0.02		2.33	0.02	nd	—	0.01		nd	—	1.51	0.15
979	m-xylene	nd	—	0.73	0.09	nd	—	nd	—	0.01		0.50	0.05
1200	Dodecan	nd	—	nd	—	nd	—	nd	—	nd	—	0.67	0.03
1093	Styrene	0.01	0.01	6.15	0.12	0.01		0.03		nd	—	0.35	0.02
1166	2-ethenyl-1,1-dimethyl-3-methylenecyclohexane	nd	—	nd	—	0.52	0.03	nd	—	nd	—	nd	—
1270	Hydrocarbon	nd	—	nd	—	nd	—	nd	—	nd	—	1.11	0.08
1278	Methyl-(1-methylethenyl)-benzene	0.01	—	nd	—	nd	—	nd	—	0.12	0.08	nd	—
	Total	0.04		11.45		0.54		0.04		0.14		7.56
	Mono-di-terpenes
709	Triciclene	0.02		nd	—	nd	—	0.03	—	nd	—	nd	—
726	α-pinene	0.24	0.01	3.97	0.09	0.02	0.01	0.38	0.03	0.15	0.02	nd	—
735	α-thujene	nd	—	nd	—	nd	—	0.02	—	0.06	—	nd	—
776	Camphene	0.23	0.02	4.55	0.12	nd	—	0.98	0.05	0.10	—	nd	—
842	β-pinene	0.10	—	nd	—	nd	—	0.27	0.02	0.05	—	nd	—
876	Sabinene	0.02	—	nd	—	nd	—	0.09	0.01	0.03	—	nd	—
931	α-phellandrene	nd	—	nd	—	nd	—	0.01	—	0.01	—	nd	—
971	β-mircene	0.03	—	nd	—	0.19	0.03	0.13	0.01	0.41	0.02	0.11	0.01
978	α-terpinene	0.05	—	nd	—	0.01	—	nd	—	0.06	0.21	nd	—
1008	D-limonene	0.13		3.60	0.11	0.08	0.01	0.10	0.01	0.61	0.03	0.65	0.03
1081	Cis-ocimene	2.17	0.04	nd	—	3.19	0.05	3.30	0.08	19.99	0.37	3.38	0.08
1099	Trans-ocimene	0.05	0.01	nd	—	0.05	0.01	0.14	0.02	0.69	0.04	0.37	0.02
1111	Cymene	0.14	0.02	nd	—	0.03	0.01	nd	—	2.11	0.03	0.77	0.05
1127	α-terpinolene	0.05	0.01	nd	—	0.01	—	0.01	—	0.28	0.01	nd	—
1223	Allo ocimene isomer	nd	—	nd	—	0.01	—	0.02	—	0.73	0.03	nd	—
1227	Allo-ocimene	0.02		nd	—	nd	—	nd	—	0.10	0.01	0.10	0.02
1494	Naphthalene	nd	—	nd	—	nd	—	nd	—	nd	—	4.85	0.09
	Total	3.25		12.12		3.59		5.48		25.39		10.23
	Sesquiterpenes
1301	α-cubebene	0.39	0.13	2.43	0.24	1.91	0.07	1.19	0.06	nd	—	1.16	0.14
1316	𝛿-elemene	22.01	0.09	5.47	0.18	4.80	0.21	4.39	0.03	18.03	0.27	3.72	0.17
1321	𝛼-ylangene	0.15	0.01	nd	—	0.64	0.02	8.15	0.02	0.57	0.03	nd	—
1328	𝛼-copaene	2.53	0.07	7.39	0.04	11.44	0.15	4.20	0.03	3.25	0.05	2.80	0.08
1355	𝛼-gurjunene	0.09	0.01	nd	—	0.39	0.01	0.99	0.02	nd	—	nd	—
1363	β-cubebene	0.65	0.05	nd	—	0.76	0.02	0.37	0.01	0.68	0.03	nd	—
1387	Sesquiterpene	0.05	0.02	nd	—	0.10	0.02	0.09	0.02	nd	—	3.08	0.08
1390	Sesquiterpene	1.58	0.03	nd	—	1.00	0.07	0.35	0.06	nd	—	nd	—
1402	β-caryophyllene	1.80	0.03	11.02	0.54	22.39	0.18	6.68	0.14	nd	—	37.32	0.19
1410	Aromadendrene	0.16	0.01	2.91	0.08	3.21	0.03	11.60	0.08	nd	—	1.85	0.07
1413	Sesquiterpene	0.22	0.01	nd	—	nd	—	nd	—	7.73	0.24	nd	—
1424	Sesquiterpene	0.41		nd	—	1.07	0.02	1.40	0.03	0.96		nd	—
1435	Sesquiterpene	0.16		nd	—	nd	—	nd	—	nd	—	2.12	0.03
1440	Calarene	1.15	0.03	nd	—	0.45	0.01	0.76	0.01	2.19	0.02	nd	—
1452	𝛼-caryophyllene	nd	—	8.70	0.25	12.00	0.07	7.12	0.17	nd	—	7.16	0.08
1454	Sesquiterpene	4.26	0.02	nd	—	0.55	0.01	nd	—	nd	—	nd	—
1462	Isoledene	1.80	0.04	nd	—	nd	—	0.43	0.01	3.41	0.19	nd	—
1469	Sesquiterpene	nd	—	nd	—	nd	—	nd	—	3.88	0.21	nd	—
1471	𝛾-muurolene	0.99	0.01	2.95	0.07	1.55	0.02	1.96	0.02	2.74	0.13	1.92	0.07
1476	β-cadinene	1.80	0.03	2.10	0.08	2.01	0.02	1.80	0.01	2.41	0.08	2.18	0.12
1486	D-germacrene	27.83	0.17	7.11	0.16	10.09	0.09	21.13	0.31	7.29	0.15	1.96	0.03
1487	β-selinene	nd	—	nd	—	0.83	0.02	0.66	0.02	nd	—	1.24	0.03
1496	𝛼-selinene	nd	—	nd	—	0.51	0.03	0.53	0.01	1.81	0.08	nd	—
1499	𝛾-elemene	3.69	0.04	5.76	0.31	12.45	0.19	11.18	0.12	3.28	0.09	1.13	0.07
1516	Sesquiterpene	1.15	0.07	nd	—	nd	—	nd	—	nd	—	nd	—
1519	𝛿-cadinene	2.14	0.07	5.75	0.43	4.70	0.05	5.17	0.11	8.89	0.13	5.78	0.15
1527	Sesquiterpene	18.07	0.16	nd	—	1.47	0.03	2.73	0.09	0.23	0.01	nd	—
1531	1,2,3,4,4a,7-naphthalene hexahydro-1,6-dimethyl-4-(1-methylethyl)	0.10	—	nd	—	0.19	0.01	0.24	0.01	0.76	0.02	0.26	0.02
1537	𝛼-muurolene	0.29	—	nd	—	0.22	0.01	0.24	0.02	1.54	0.09	0.46	0.02
1557	Sesquiterpene	0.82	0.02	nd	—	0.32	0.02	0.25	0.02	1.96	0.04	0.44	0.03
1563	Calamenene	nd	—	nd	—	0.05	—	0.07	0.01	0.19	0.01	0.99	0.02
1612	𝛼-calacorene	nd	—	nd	—	0.02	—	0.03	0.01	0.08	0.01	0.64	0.01
1642	Sesquiterpene	nd	—	nd	—	nd	—	0.05	0.01	0.25	0.02	2.08	0.07
1663	Humulene oxide	nd	—	nd	—	0.05	—	0.03		nd	—	nd	—
1667	Nerolidol	nd	—	nd	—	0.15	0.01	nd	—	nd	—	nd	—
1691	Spathulenol	nd	—	nd	—	0.26	0.02	0.16		nd	—	0.84	0.02
1728	𝛼-cadinol	0.01	—	nd	—	nd	—	nd	—	0.11	0.02	0.17	0.02
	Total	94.3		61.59		95.58		93.95		72.24		79.3

aThe Kovats retention index calculated for Rtx-Wax capillary column (25 m × 0.25 𝜇m × 0.25 mm i.d.).
^bNormalized amount of volatile compounds (percentage); (peak of volatile compound/total peak area of all volatile compounds) of B. orellana (𝑛=3) obtained from different parts.
^cNormalized amount of volatile compounds (percentage); (peak of volatile compound/total peak area of all volatile compounds) of B. orellana living plants using in vivo sampling (𝑛=3).
s.d.: ± standard deviation.
nd: not detected.