Chemical composition and bioactivities of the essential oil of Coreopsis tinctoria and Chrysanthemum morifolium

Figures & data

Figure 1. Aroma radar map of two essential oils.

Table 1. Optimization of the flower powder–water ratio.

Weight of flower powder (g)	Flower powder––water ratio	Yield of essential oil (g)	Yield rate of essential oil (%, g/g)
37.5	2.5:100	0.09	0.24
75.0	5.0:100	0.27	0.36
112.5	7.5:100	0.43	0.38
150.0	10.0:100	0.44	0.29

Table 2. Optimization of the hydrodistillation time.

Flower powder–water ratio	Time (h)/Yield of essential oil (g)
	1.0 h	2.0 h	3.0 h	4.0 h
5.0:100	0.20	0.26	0.27	0.27
7.5:100	0.31	0.39	0.43	0.43

Figure 2. Relative contents of chemical compositions of CTFEO and CMFEO.

Table 3. Chemical composition of CTFEO and CMFEO identified by GC-MS (100%).

Type	No.	tR (min)	Flavor compounds	CTFEO	CMFEO
Terpene	1	8.20	α-pinene	3.8967	–
	2	8.51	2,2-dimethyl-3-methylene-(1S)-bicyclo[2.2.1]heptane	0.6356	–
	3	8.79	4-methyl-1-(1-methylethyl)-bicyclo[3.1.0]hex-2-ene	–	0.3904
	4	8.89	2-methyl-5-(1-methylethyl)-bicyclo[3.1.0]hex-2-ene	1.1208	0.0837
	5	8.94	(1S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene	–	0.2932
	6	9.16	4-methylene-1-(1-methylethyl)-bicyclo[3.1.0]hex-2-ene	0.1810	0.7127
	7	9.39	β-myrcene	1.5651	–
	8	9.73	4-methylene-1-(1-methylethyl)-bicyclo[3.1.0]hexane	0.4525	0.0465
	9	9.82	β-pinene	0.4525	0.0576
	10	9.89	2-carene	0.1800
	11	10.06	2,3-dehydro-1,8-cineole	–	0.1973
	12	10.28	trans-β-ocimene	0.8490	–
	13	10.37	α-phellandrene	–	0.1538
	14	10.57	1-methyl-4-(1-methylethyl)-1,3-cyclohexadiene	–	0.1786
	15	10.80	D-limonene	34.5437	1.2903
	16	10.89	1,2-cyclononadiene	0.1038	–
	17	11.17	trans-2-caren-4-ol	–	0.2584
	18	11.30	γ-terpinene	0.3643	0.2693
	19	11.38	3-(4-methyl-3-pentenyl)-furan	0.2795	–
	20	11.57	1,3,8-p-menthatriene	0.2863	–
	21	11.89	4-acetyl-1-methylcyclohexene	0.3031	–
	22	12.00	trans-limonene oxide	0.4598	–
	23	12.20	3-methylenecyclohexene	0.3250	–
	24	12.25	1-(1,4-dimethyl-3-cyclohexen-1-yl)-ethanone	–	0.3843
	25	12.33	2,6-dimethyl-2,4,6-octatriene	–	0.2310
	26	12.88	(+)-2-bornanone		0.8255
	27	13.33	endo-borneol		0.1870
	28	14.59	ethyl-tetramethyl-cyclopentadiene	0.1190	–
	29	14.85	silphiperfol-5-ene	0.3441	–
	30	14.95	(1 R,2S,7 R,8 R)-2,6,6,9-tetramethyl-tricyclo[5.4.0.0(2,8)]undec-9-ene	0.3171	–
	31	15.12	7-epi-silphiperfol-5-ene	3.2089	–
	32	15.29	silphiperfola-4,7(14)-diene	0.4974	–
	33	15.59	1,5,5-trimethyl-6-methylene-cyclohexene	–	0.3405
	34	15.63	modephene	0.8197	–
	35	15.73	(1 R,3aS,5aS,8aR)-1,3a,4,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene	0.5317	–
	36	15.90	2,4,5,6,7,8-hexahydro-1,4,9,9-tetramethyl-[3aR-(3aα,4β,7α)]-3 H-3a,7-methanoazulene	0.2622	–
	37	16.01	(–)-3,7,7-trimethyl-11-methylene-spiro[5.5]undec-2-ene	0.2765	–
	38	16.13	ylangene	–	0.1165
	39	16.22	copaene	–	0.2274
	40	16.29	1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-[1aR-(1aα,7α,7aα,7bβ)]-1 H-cyclopropa[a]naphthalene	–	0.5799
	41	16.30	trans-α-bergamotene	4.4457	–
	42	16.56	(–)-β-elemene	–	8.8754
	43	16.63	1,5,9,9-tetramethyl-Z,Z,Z-1,4,7,-cycloundecatriene	0.2754	–
	44	16.76	2-isopropyl-5-methyl-9-methylene-bicyclo[4.4.0]dec-1-ene	0.5552	–
	45	16.80	[3 R-(3α,3aβ,7β,8aα)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1 H-3a,7-methanoazulene	–	3.3848
	46	16.92	[1aR-(1aα,4α,4aβ,7bα)]-1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl-1 H-cycloprop[e]azulene	0.2426	–
	47	17.00	1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-naphthalene	–	3.0108
	48	17.03	caryophyllene	0.6908	1.3146
	49	17.04	(3 R,3aR,7 R,8aS)-3,8,8-trimethyl-6-methyleneoctahydro-1 H-3a,7-methanoazulene	2.1503	–
	50	17.30	germacrene D	0.1402	–
	51	17.38	β-bisabolene	0.2433	–
	52	17.46	cis-β-farnesene	–	5.5262
	53	17.55	alloaromadendrene	–	1.6506
	54	17.67	1-isopropyl-4,7-dimethyl-1,2,3,5,6,8a-hexahydronaphthalene	0.2557	–
	55	17.88	β-guaiene	–	0.7939
	56	18.06	α-calacorene	0.1164	–
	57	18.11	1-(1,5-dimethyl-4-hexenyl)-4-methyl-benzene	1.3239	3.924
	58	18.18	(4aR,8aS)-4a-methyl-1-methylene-7-(propan-2-ylidene)decahydronaphthalene	–	5.2308
	59	18.36	(4aS-cis)-2,4a,5,6,7,8,9,9a-octahydro-3,5,5-trimethyl-9-methylene-1 H-benzocycloheptene	–	1.1731
	60	18.40	(Z)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene	–	0.8199
	61	18.49	(3S,3aS,8aR)-6,8a-dimethyl-3-(prop-1-en-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulene		2.8263
	62	18.67	10S,11S-himachala-3(12),4-diene	0.0550	1.3359
	63	18.93	caryophyllene oxide	1.2341	–
	64	18.97	(–)-β-sesquiphellandrene	–	5.8797
	65	19.12	4-[(1E)-1,5-dimethyl-1,4-hexadien-1-yl]-1-methyl-cyclohexene	–	0.2846
	66	19.51	ledene oxide	0.7053	–
	67	19.74	[1 R-(1α,7β,8aα)]-1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-naphthalene	0.2665	–
	68	19.94	1,5-epoxysalvial-4-ene	0.1666	0.1603
	69	20.46	(1α,3aα,7α,8aβ)-2,3,6,7,8,8a-hexahydro-1,4,9,9-tetramethyl-1 H-3a,7-methanoazulene	–	2.9351
	70	20.47	longifolene	0.1691	–
	71	20.96	2-ethenyl-1,3,3-trimethyl-cyclohexene	0.1117	–
	72	21.21	7-epi-cis-sesquisabinene hydrate	0.1763	–
	73	21.61	[2 R-(2α,4aα,8aβ)]-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)-naphthalene	–	0.2160
	74	22.13	β-humulene	–	1.5262
	75	22.34	aromandendrene	–	0.9222
	76	22.77	(+)-ledene	–	5.5309
	77	23.44	5-ethylidene-1-methyl-cycloheptene	–	0.3683
	78	24.04	isoaromadendrene epoxide	0.0906	0.2379
	79	24.56	dehydrochamazulene	–	0.1412
	80	25.96	(E)-2-(hepta-2,4-diyn-1-ylidene)-1,6-dioxaspiro[4.4]non-3-ene	–	1.5787
		Subtotal		65.3375	66.4713
Alcohol	81	10.88	eucalyptol	–	0.3417
	82	11.72	trans-1-methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol	2.0223	–
	83	12.12	2-caren-4-ol	0.3701	–
	84	12.77	[1S-(1α,3α,5α)]-6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol	0.3233	0.1649
	85	12.80	trans-p-mentha-1(7),8-dien-2-ol	1.4716	–
	86	12.88	(+)-2-bornanone	–	0.8255
	87	13.00	(–)-cis-isopiperitenol	2.7212	–
	88	13.16	(1S)-4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-one	0.1043	–
	89	13.33	endo-borneol	–	0.1870
	90	13.43	terpinen-4-ol	1.1914	0.9568
	91	13.54	(–)-myrtenol	–	0.0506
	92	13.63	α-terpineol	–	0.774
	93	13.80	trans-shisool	–	0.1528
	94	13.93	cis-carveol	5.4920	0.0382
	95	14.25	(1α,3α,5α)-4-methylene-1-(1-methylethyl)-bicyclo[3.1.0]hexan-3-ol	0.1856	0.0158
	96	14.33	p-mentha-1,8-dien-7-ol	0.3126	–
	97	15.52	4-(1-methylethyl)-1,4-cyclohexadiene-1-methanol	–	0.0686
	98	17.63	levomenol	0.1144	1.4491
	99	18.79	[1aR-(1aα,4aα,7β,7aβ,7bα)]-decahydro-1,1,7-trimethyl-4-methylene-1 H-cycloprop[e]azulen-7-ol	0.1553	–
	100	19.43	phytol	0.0514	0.4794
	101	19.57	2-methyl-5-(1-methylethenyl)-cyclohexanol	–	1.1265
	102	20.30	2-[(2 R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]prop-2-en-1-ol	–	2.0703
	103	20.58	(Z)-1,3,3-trimethyl-2-(3-methyl-2-methylene-3-butenylidene)-cyclohexanol	0.4708	–
	104	21.38	humulenol-II	–	0.4142
	105	21.52	[(4aS,8S,8aR)-8-isopropyl-5-methyl-3,4,4a,7,8,8a-hexahydronaphthalen-2-yl]methanol	0.4124	–
	106	23.70	6-isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol	–	2.6504
	107	26.97	2-naphthaleneethanol	–	0.1365
		Subtotal		15.3987	11.9023
Alkane	108	15.91	1,1,7,7a-tetramethyl-1a,2,6,7,7a,7b-hexahydro-1 H-cyclopropa[a]naphthalene	–	0.2476
	109	16.52	(1S,5S,6 R)-6-methyl-2-methylene-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]heptane	0.1695	–
	110	17.14	(1 R,2S,6S,7S,8S)-8-isopropyl-1-methyl-3-methylenetricyclo[4.4.0.02,7]decane	–	1.5211
	111	19.36	icosa-9,11-diyne	0.2755	–
	112	20.08	5-heptene-1,3-diyn-1-yl-benzene	1.6746	–
	113	27.40	eicosane	0.1157	–
		Subtotal		2.2353	1.7687
Aldehyde	114	11.81	α-campholenal	0.3509	–
	115	14.12	4-(1-methylethenyl)-1-cyclohexene-1-carboxaldehyde	0.5230	–
	116	14.30	4-(1-methylethyl)-benzaldehyde	0.2855	0.1106
	117	15.35	(E,E)-2,4-decadienal	–	0.1857
	118	21.11	longifolenaldehyde	–	1.6947
		Subtotal		1.1594	1.9910
Phenol	119	14.48	thymol	0.5896	–
	120	14.92	2-methyl-5-(1-methylethyl)-phenol	–	0.3210
	121	14.95	3-methyl-4-isopropylphenol	–	0.9255
	122	15.18	2,3,4,6-tetramethyl-phenol	–	0.1211
	123	24.36	valerenol	–	0.2784
		Subtotal		0.5896	1.6460
Ketone	124	9.95	6-methyl-5-hepten-2-one	–	0.4790
	125	12.35	5-(1-methylethyl)-bicyclo[3.1.0]hexan-2-one	0.1472	–
	126	12.39	2,6,6-trimethyl-bicyclo[3.1.1]heptan-3-one	0.1087	–
	127	12.56	2,2,5,5-tetramethyl-3-cyclopenten-1-one	0.2506	–
	128	12.95	sabinone	–	0.3247
	129	12.96	trans-2-methyl-5-(1-methylethenyl)-cyclohexanone	0.8743	–
	130	13.09	pinocarvone	0.1286	0.1107
	131	13.22	4-methyl-1-(1-methylethyl)-bicyclo[3.1.0]hex-3-en-2-one	0.1797	2.1811
	132	13.67	D-carvone	2.8879	–
	133	13.72	2-methylene-5-(1-methylethyl)-cyclohexanone	0.2959	–
	134	16.48	(E)-6,10-dimethyl-5,9-undecadien-2-one	0.1763	–
	135	19.82	silphiperfol-6-en-5-one	0.9018	–
	136	20.65	salvial-4(14)-en-1-one	0.6828	0.7749
	137	21.86	acorenone B	–	1.0348
	138	23.23	4-(1,5-dimethylhex-4-enyl)cyclohex-2-enone	–	0.9727
	139	24.13	7-isopropenyl-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3 H-naphthalen-2-one	–	0.2331
	140	24.2	4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one	–	0.2840
	141	25.17	6,10,14-trimethyl-2-pentadecanone	0.1472	0.1926
	142	28.43	(Z)-18-octadec-9-enolide	0.1179	0.0079
	143	31.45	heptacosane-4,6-dione	0.1255	–
		Subtotal		7.0244	6.5955
Acid	144	14.26	acetic acid-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester	0.9651	–
	145	18.26	dodecanoic acid	0.5095	–
	146	23.59	3-(2-isopropyl-5-methylphenyl)-2-methylpropionic acid	–	1.0217
	147	29.13	n-hexadecanoic acid	0.1455	–
	148	30.89	sorbic acid	0.1667	–
		Subtotal		1.7868	1.0217
Ester	149	14.10	n-valeric acid cis-3-hexenyl ester	–	0.1282
	150	14.79	5-methyl-2-(1-methylethenyl)-4-hexen-1-ol acetate	–	0.2059
	151	15.44	myrtenyl acetate	–	0.1292
	152	19.16	fumaric acid butyl myrtenyl ester	–	0.2715
	153	19.29	nonanoic acid phenylmethyl ester	–	0.7074
	154	24.35	3-methyl-butanoic acid-2-methoxy-4-(2-propenyl)phenyl ester	0.1282	–
	155	27.66	(Z,Z)-9,12-octadecadienoic acid methyl ester	0.1062	0.0098
	156	28.69	14-methyl-pentadecanoic acid methyl ester	0.1700	–
		Subtotal		0.4044	1.4520
Aromatic	157	7.32	p-xylene	0.1387	–
	158	11.85	1-methyl-4-(1-methylethenyl)-benzene	0.4334	0.0574
	159	13.82	N,N-dipropionylphenethylamine	1.3963	–
	160	14.41	N-(2-phenylethyl)-acetamide	–	0.1871
	161	18.71	1-ethyl-2,3-dimethyl-benzene	0.0941	–
		Subtotal		2.0625	0.2445

*–, not detected.

Table 4. Antibacterial activities of CTFEO and CMFEO (mg/mL).

Components	Pa^a	Kp^a	Ec^a	Sa^a	Ef^a	Bs^a
CTFEO	0.808 ± 0.055	1.412 ± 0.198	0.518 ± 0.081	0.520 ± 0.048	0.721 ± 0.058	0.183 ± 0.060
CMFEO	0.894 ± 0.072	2.227 ± 0.2512	1.427 ± 0.106	0.683 ± 0.085	0.807 ± 0.061	0.340 ± 0.051
Penicillin G^b				0.002 ± 0.0002	0.003 ± 0.0004	0.002 ± 0.0003
Streptomycin^b	0.003 ± 0.0003	0.004 ± 0.0006	0.002 ± 0.0003

^aPa (P. aeruginosa ATCC 27853), Kp (K. pneumonia), Ec (E. coli ATCC 25922), Sa (S. aureus ATCC 25923), Ef (E. faecalis ATCC 29212), Bs (B. subtilis ATCC 6633); ^bPositive control.

Figure 3. Inhibition on LPS-induced mRNA expression of IL-1β, IL-6, and TNF-α of two essential oils at 10.0 μg/mL. ^####p<.0001, in comparison with control group; **p < .01, in comparison with LPS group; ****p < .0001, in comparison with LPS group.