Chemical composition, antioxidant and antibacterial activities of essential oils from Ferulago angulata

Figures & data

Table 1. Geographical and climate of natural habitats of F. angulata populations.

Region (province)	Altitude (m)	Latitude (UTM)	Longitude (UTM)	P^a	T	pH^c	E.C.	O.C.	Sand	Silt	Clay
Olya (Isfahan)	2447	470,002	3,643,003	355.2^b	10.55	7.42	0.412	0.702	21	38	41
Saldaran (Chaharmahal va Bakhtiari)	3000	452,900	3,562,063	405.9	11.95	7.64	0.633	3.301	23.5	38.5	38
Kallar (Chaharmahal va Bakhtiari)	2592	501,914	3,470,038	366.9	10.43	7.47	0.509	2.204	17	48	35
Rig (Chaharmahal va Bakhtiari)	2116	494,280	3,523,374	603.8	15.42	7.46	0.400	0.780	30	32	38

a P, annual precipitation (mm); T, average temperature (°C); E.C.., electrical conductivity (dS m⁻¹); O.C., organic carbon (%), and sand, silt and clay in %.

b Meteorological information was obtained from weather stations located within the study area and the surrounding zone; each value in the mean of 10–15 year data.

c Soil characteristics are based on average of samples taken from three farms in each region.

Figure 1. The essential oil yield of F. angulata populations (significant different at p < 0.05 have been indicated with different letters).

Figure 2. The aerial parts of F. angulata and the chromatogram found in a sample (for peak identification see Table 2).

Table 2. Chemical compositions of the essential oils from F. angulata populations.

Row	Components	RI(cal)^a	RI(lit)^a	Saldaran population	Kallar population	Rig population	Olya population
Monoterpenes hydrocarbons
1	α-Thujene	930	931	0.19 ± 0.27^b	0.68 ± 0.35	0.80 ± 0.11	2.73 ± 0.78
2	α-Pinene**	939	939	35.86 ± 11.34^c	16.63 ± 2.37	16.84 ± 0.68	9.89 ± 3.23
3	Camphene	951	953	1.42 ± 0.36	1.30 ± 0.09	0.45 ± 0.08	1.38 ± 0.80
4	Verbenene	967	967	0.43 ± 0.10	0.41 ± 0.14	0.06 ± 0.05	0.04 ± 0.06
5	Sabinene**	981	976	1.97 ± 0.29	1.35 ± 0.66	13.23 ± 0.63	5.82 ± 3.34
6	β-Pinene	985	980	2.83 ± 0.13	1.48 ± 0.33	1.99 ± 0.08	0.89 ± 0.77
7	Myrcene**	995	991	3.59 ± 0.28	2.47 ± 0.20	2.63 ± 0.21	6.16 ± 1.32
8	α-Phellandrene**	1008	1005	2.35 ± 0.52	7.50 ± 1.61	0.38 ± 0.09	1.47 ± 1.38
9	Δ-3-Carene	1012	1011	0.33 ± 0.47	0.39 ± 0.38	0.35 ± 0.12	3.17 ± 2.50
10	α-Terpinene	1017	1018	0.07 ± 0.10	0.21 ± 0.08	2.01 ± 0.38	0.85 ± 1.05
11	p-Cymene	1025	1026	1.28 ± 0.11	2.75 ± 0.55	2.46 ± 0.20	2.65 ± 1.66
12	Sylvestrene	1029	1027	2.45 ± 3.46	0.00 ± 0.00	1.02 ± 1.77	1.74 ± 3.01
13	β-Phellandrene**	1030	1031	0.00 ± 0.00	7.40 ± 1.45	0.00 ± 0.00	0.00 ± 0.00
14	Limonene	1032	1031	2.39 ± 3.37	0.00 ± 0.00	1.89 ± 1.65	2.11 ± 1.83
15	cis-β-Ocimene^n.s	1041	1040	19.05 ± 4.20	16.18 ± 0.72	16.68 ± 2.23	23.69 ± 5.37
16	trans-β-Ocimene**	1048	1050	2.86 ± 0.37	2.47 ± 0.54	2.99 ± 0.45	7.45 ± 0.75
17	ɣ-Terpinene	1058	1062	0.23 ± 0.04	0.56 ± 0.36	5.96 ± 0.78	5.27 ± 4.90
Oxygenated monoterpenes
18	α-Terpinolene	1088	1088	0.58 ± 0.17	1.59 ± 0.45	0.95 ± 0.14	0.74 ± 0.43
19	Linalool	1104	1098	2.04 ± 0.94	3.30 ± 0.26	1.86 ± 0.40	1.27 ± 0.18
20	allo-Ocimene	1126	1129	0.88 ± 0.27	0.84 ± 0.02	0.84 ± 0.12	1.07 ± 0.23
21	cis-Verbenol	1138	1140	0.72 ± 0.52	0.92 ± 0.20	0.29 ± 0.04	0.30 ± 0.27
22	trans-Verbenol	1143	1144	0.00 ± 0.00	2.22 ± 1.95	0.25 ± 0.43	0.44 ± 0.55
23	Citronellal	1150	1153	0.04 ± 0.06	0.11 ± 0.05	0.37 ± 0.05	0.05 ± 0.09
24	Terpine-4-ol	1174	1177	0.44 ± 0.24	0.60 ± 0.26	5.16 ± 0.85	1.65 ± 2.38
25	α-Terpineol	1187	1189	0.30 ± 0.04	0.72 ± 0.10	0.63 ± 0.08	0.30 ± 0.27
26	Myrtenol	1195	1194	0.00 ± 0.00	0.05 ± 0.08	0.11 ± 0.02	0.00 ± 0.00
27	Deacanal	1202	1204	0.11 ± 0.16	0.07 ± 0.06	0.24 ± 0.03	0.10 ± 0.12
28	trans-Carveol	1215	1217	0.46 ± 0.65	0.04 ± 0.06	0.04 ± 0.04	0.00 ± 0.00
29	Citronellol	1224	1228	0.38 ± 0.21	1.08 ± 0.21	1.62 ± 0.34	0.25 ± 0.25
30	Nerol	1225	1228	0.05 ± 0.06	0.00 ± 0.00	0.00 ± 0.00	0.06 ± 0.06
31	Geraniol	1250	1255	0.08 ± 0.11	0.53 ± 0.12	0.11 ± 0.10	0.11 ± 0.10
32	Bornyl acetate	1280	1285	2.51 ± 1.89	2.35 ± 0.66	1.45 ± 0.08	4.50 ± 2.47
33	Thymol*	1286	1290	0.18 ± 0.25	6.86 ± 4.89	0.41 ± 0.48	0.32 ± 0.24
34	Carvacrol	1295	1298	0.00 ± 0.00	0.69 ± 0.37	0.24 ± 0.16	0.08 ± 0.09
Sesquiterpenes hydrocarbons
35	α-Cubebene	1369	1345	0.12 ± 0.17	0.07 ± 0.12	0.00 ± 0.00	0.13 ± 0.23
36	Β-Elemene	1386	1375	0.00 ± 0.00	0.11 ± 0.06	0.07 ± 0.02	0.03 ± 0.06
37	cis-Jasmone	1393	1394	0.00 ± 0.00	0.09 ± 0.09	1.59 ± 0.54	0.67 ± 0.11
38	Methyl eugenol	1399	1401	0.30 ± 0.42	0.59 ± 0.13	1.07 ± 0.28	0.30 ± 0.13
39	Β-Caryophyllene	1412	1418	0.62 ± 0.18	1.53 ± 0.18	0.20 ± 0.20	0.75 ± 0.77
40	β-Humulene	1446	1440	0.00 ± 0.00	0.12 ± 0.03	0.00 ± 0.00	1.53 ± 2.50
41	γ-Curcumene	1473	1478	0.40 ± 0.30	0.00 ± 0.00	0.00 ± 0.00	0.06 ± 0.10
42	Germacrene-D	1474	1480	0.00 ± 0.00	0.03 ± 0.05	0.03 ± 0.04	0.00 ± 0.00
43	Bicyclogermacrene	1490	1494	2.55 ± 1.17	2.25 ± 1.04	2.03 ± 0.10	3.21 ± 3.30
44	cis-γ-Bisabolene	1508	1515	0.00 ± 0.00	0.07 ± 0.06	0.00 ± 0.00	0.00 ± 0.00
45	Δ-Cadinene	1516	1524	0.58 ± 0.18	0.49 ± 0.14	0.08 ± 0.09	0.65 ± 0.78
46	Germacrene-B	1547	1560	0.22 ± 0.31	0.25 ± 0.11	0.36 ± 0.11	0.00 ± 0.00
Oxygenated sesquiterpenes
47	Spathulenol	1569	1576	0.35 ± 0.00	0.59 ± 0.27	0.46 ± 0.16	1.31 ± 1.08
48	Caryophyllene oxide	1573	1581	0.06 ± 0.08	0.34 ± 0.11	0.05 ± 0.09	0.21 ± 0.37
49	Guaiol	1589	1595	0.00 ± 0.00	0.13 ± 0.06	0.06 ± 0.05	0.00 ± 0.00
	Total identified			91.19	90.89	90.34	95.47

n.s Not significant; *significant at p ≤0.05; **significant at p ≤0.01.

a Retention indices (RI) relative to C₅–C₂₄ n-alkanes on HP-5MS capillary column. cal = determined values; lit = literature values.

b % GC peak, the percentage composition was computed from the GC peak areas.

c Values of major compounds are given as means ± SD.

Figure 3. Dendrogram obtained by hierarchical cluster analysis (HCA).

Table 3. Antibacterial activity of essential oils from the studied populations of F. angulata.

Pathogens	Olya		Rig		Kallar		Saldaran
	MIC (μg/mL)	MBC (μg/mL)	MIC (μg/mL)	MBC (μg/mL)	MIC (μg/mL)	MBC (μg/mL)	MIC (μg/mL)	MBC (μg/mL)
Staphylococcus aureus	>500	>500	>500	>500	>500	>500	>500	>500
Bacillus cereus	>500	>500	>500	>500	>500	>500	>500	>500
Listeria monocytogenes	125	250	125	250	250	500	62	250
Salmonella typhimurium	>500	>500	>500	>500	>500	>500	>500	>500

Figure 4. The antioxidant activity of the essential oils from the studied populations of F. angulata and a chemical antioxidant (BHT) using DPPH assay (IC₅₀ value = μg/mL) (significant different at p < 0.05 have been indicated with different letters).