Trans-β-Caryophyllene: An Effective Antileishmanial Compound Found in Commercial Copaiba Oil (Copaifera spp.)

Table 1

Constituents of the commercial copaiba oils.

Constituent		Relative abundance (%)^1
	RI^2	C1	C2	C3	C4	C4-VF	C4-NVF
Sesquiterpenes
𝛿-Elemene	1340				0.87 ± 0.05	1.26 ± 0.14
𝛼-Cubebene	1350			2.41 ± 0.02	0.72 ± 0.07	0.89 ± 0.15
𝛼-Copaene	1379	1.57 ± 0.12		18.16 ± 0.15	7.18 ± 0.26	11.22 ± 0.73
𝛽-Elemene	1391	0.79 ± 0.08		2.39 ± 0.02	1.47 ± 0.00	1.96 ± 0.30
𝛽-Caryophyllene (trans)	1427	44.23 ± 3.20	12.83 ± 0.13	5.53 ± 0.04	36.46 ± 1.69	42.36 ± 5.66
𝛼-Bergamotene	1439	0.97 ± 0.06	11.84 ± 0.15	1.99 ± 0.02	7.29 ± 0.33	9.11 ± 1.26
𝛽-Humulene	1453				1.18 ± 0.02	1.45 ± 1.19
𝛼-Humulene	1465	7.29 ± 0.49	2.43 ± 0.08	1.10 ± 0.01	5.30 ± 0.06	5.63 ± 1.10
Allo-aromadendrene	1469			1.16 ± 0.02	0.66 ± 0.07	0.76 ± 0.38
𝛾-Muurolene	1483				2.49 ± 0.03	2.37 ± 0.35
Germacrene D	1488				4.56 ± 0.013	2.65 ± 0.55
𝛽-Selinene	1493	0.46 ± 0.02	2.40 ± 0.03	4.74 ± 0.03	0.62 ± 0.01	—
𝛼-Selinene	1499	0.35 ± 0.03	1.46 ± 0.01	3.03 ± 0.05
Bicyclogermacrene	1500				1.00 ± 0.01	0.45 ± 0.14
𝛼-Muurolene	1500				1.04 ± 0.01	0.46 ± 0.36
𝛽-Bisabolene	1509	1.55 ± 0.11	𝟏𝟐.𝟔𝟓±𝟎.𝟗𝟑	4.50 ± 0.02	1.26 ± 0.01	1.04 ± 0.64
𝛿-Amorphene	1514				5.14 ± 0.16	1.14 ± 0.67
𝛽-Sesquiphellandrene	1522		0.72 ± 0.06
𝛾-Cadinene	1522	0.80 ± 0.06		4.61 ± 0.01	1.55 ± 0.02	2.01 ± 0.56
Iso-𝛾-Bisabolene (E)	1534		0.88 ± 0.02	0.48 ± 0.01
Germacrene B	1565	0.67 ± 0.06
Caryophyllene alcohol	1578	1.00 ± 0.18
Caryophyllene oxide	1589	10.17 ± 0.77	0.85 ± 0.04	1.10 ± 0.02		6.83 ± 0.62
Humulene epoxide II	1608					0.72 ± 0.09
Unknow [M]^+ 322	1631				1.31 ± 0.02	0.96 ± 0.18
𝛼-Muurolol	1642	2.12 ± 0.16		0.60 ± 0.01
𝛼-Cadinol	1651				1.55 ± 0.90	0.70 ± 0.12
Diterpenes^3
Unknown acid (kaurene type; [M]^+ 294)		traces
Kaur-16-ene		traces		3.08 ± 0.03
Eperuic acid		0.69 ± 0.13	2.31 ± 0.05	2.61 ± 0.02	0.62 ± 0.13		4.69 ± 0.62
Clerod-3-en-15-oic acid isomer ([M]^+ 320)			3.13 ± 0.06	5.28 ± 0.04
Labd-7-en-15-oic acid			1.07 ± 0.04	0.80 ± 0.01
Kaurenoic acid				10.10 ± 0.09
Copalic acid		6.32 ± 0.81	2.82 ± 0.40	2.16 ± 0.02	7.62 ± 0.62		49.87 ± 1.06
Kovalenic acid		0.43 ± 0.06	1.75 ± 0.32
Daniellic acid		3.16 ± 0.43	33.65 ± 1.05	8.25 ± 0.19
Hardwickiic acid			0.77 ± 0.08	900 ± 0.07
Pinifolic acid		0.51 ± 0.10	3.65 ± 0.19
Agathic acid		2.66 ± 0.30			0.95 ± 0.31		6.65 ± 0.10
Hydroxy-copalic acid		1.80 ± 0.27			1.20 ± 0.76		9.39 ± 0.14
Acetoxy-copalic acid		4.13 ± 1.21			2.97 ± 0.32		19.56 ± 0.48
Total sesquiterpenes		71.96	46.06	51.81	81.65
Total diterpenes		19.71	49.15	41.28	13.36
Total identified		91.67	95.21	93.09	95.01

1Values for C1–C4 and C4-NVF: from the relative peak area in the chromatograms; for C4-VF: quantification using commercial 𝛽-caryophyllene as analytical standard. ²RI = retention index. See Adams, 2007 [21]. ³Analyzed as the methyl ester derivatives. In bold: more abundant constituents in the oil samples.