Chemical Composition and Antimicrobial Activities of the Essential Oils of Teucrium chamaedrys. subsp. chamaedrys., T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium.

Figures & data

Table 1. Identified components in the essential oil of T. chamaedrys. subsp. chamaedrys, T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium.^a..

		T. chamaedrys. subsp. chamaedrys.		T. orientale. var. puberulens.		T. chamaedrys. subsp. lydium.
No.	Compounds	% Area	Q. (%)	% Area	Q. (%)	% Area	Q. (%)	Exp. RI	Ident.(LRI/MS)
1	α-Thujene	0.2	98	—	—	0.1	91	928	929
2	α-Pinene	15.8	96	—	—	12.5	96	939	939
3	Camphene	0.1	98	—	—	0.1	98	954	952
4	(E.)-2-Heptenal	—	—	tr	92	—	—	958	961
5	β-Pinene	8.9	97	—	—	6.6	97	983	982
6	β-Myrcene	4.1	96	—	—	0.5	96	985	988
7	(E.,E.)-2,4-Heptadienal	0.1	94	—	—	—	—	997	1008
8	Phenyl oxirane	—	—	tr	87	—	—	1119	MS
9	(E.)-2-Octenal	0.1	85	—	—	—	—	1127	MS
10	2-Methyl cumarone	—	—	20.0	86	—	—	1188	MS
11	α-Terpineol	—	—	0.9	91	—	—	1196	1195
12	Safranal	—	—	0.1	95	—	—	1198	1201
13	Decanal	0.1	87	—	—	0.1	85	1205	1205
14	p.-Menth-1-en-9-al	—	—	1.0	90	—		1217	MS
15	β-Cyclocitral	0.2	92	—	—	—		1222	1218
16	Nerol	—	—	0.2	97	—		1231	1228
17	Carvone	—	—	—	—	0.2	97	1243	1241
18	Citrol	—	—	—	—	0.1	86	1255	MS
19	Geraniol	—	—	0.6	97	—	—	1257	1255
20	(E.)-2-Decenal	0.6	90	—	—	—	—	1263	1260
21	Nonanoic acid	—	—	0.1	90	—	—	1274	1275
22	Dihydroedulan I	—	—	0.2	94	—	—	1294	1289
23	Carvacrol	—	—	—	—	0.5		1299	1299
24	Tridecane	0.1	87	—	—	—		1300	1300
25	p.-Vinylguaiacol	—	—	0.3	97	—		1314	1323
26	(E.,E.)-2,4-Decadienal	0.4	94	—	—	0.1	86	1317	1316
27	Bicycloelemene	0.2	87	0.3	98	—		1340	MS
28	α-Cubebene	—	—	0.7	99	—		1353	1353
29	Eugenol	—	—	0.1	96	—		1359	1359
30	Decanoic acid	—	—	0.5	95	—		1373	1373
31	α-Copaene	0.5	99	1.3	99	0.6	99	1378	1378
32	β-Bourbonene	3.1	99	2.4	96	3.6	99	1387	1388
33	β-Cubebene	—	—	1.5	99	—	—	1392	1392
34	γ-Caryophyllene	0.2	99	0.5	99	—		1408	MS
35	β-Caryophyllene	11.8	99	21.7	99	19.7	99	1424	1424
36	epi.-Bicyclosesquiphellandrene	—	—	—	—	0.7	93	1430	MS
37	Aromadendrene	—	—	0.2	99	—	—	1442	1438
38	α-Humulene	1.0	99	4.8	99	1.7	99	1457	1457
39	(E.)-β-Farnesene	1.8	98	—	—	2.1	96	1460	1460
40	allo.-Aromadendrene	—	—	1.1	90	—	—	1465	1461
41	Germacrene D	16.7	99	10.6	99	9.3	99	1481	1481
42	Bicyclogermacrene	2.4	99	3.4	99	1.5	99	1497	1496
43	(E.,E.)-α-Farnesene	0.3	94	—	—	0.3	97	1509	1508
44	β-Bisabolone	—	—	0.4	98	—	—	1510	1509
45	γ-Cadinene	0.4	95	0.5	99	0.7	97	1516	1514
46	δ-Cadinene	2.1	99	4.1	99	1.7	99	1526	1526
47	Cadina-1,4-diene	0.2	89	—	—	—	—	1534	1532
48	α-Calacorene	0.2	95	—	—	0.4	98	1546	1546
49	Spathulenol	0.7	98	1.0	98	—	—	1580	1578
50	Caryophyllene oxide	2.4	94	2.7	94	6.1	94	1585	1584
51	Viridiflorol	—	—	0.5	99	—	—	1594	1594
52	Fonenol	—	—	0.4	90	—	—	1621	MS
53	Caryophylla-4(12),8(13)- dien-5-β-ol	—	—	—	—	0.7	99	1637	MS
54	tau-Muurolol	0.8	93	1.6	96	1.0	95	1645	1643
55	α-Cadinol	0.8	98	1.1	95	1.0	91	1657	1656
56	Caryophyllenol-II	—	—	—	—	1.1	86	1671	MS
57	Vulgarol B	—	—	0.4	87	—	—	1674	MS
58	di-epi-α-Cedrene	0.9	83	—	—	—	—	1677	MS
59	Heneicosane	0.2	83	—	—	—	—	2100	2100
60	cis.-Phytol	1.0	90	—	—	1.0	90	2113	2114
61	Tricosane	0.2	98	—	—	0.4	98	2300	2300
62	Tetracosane	—	—	—	—	0.3	96	2400	MS
63	Pentacosane	0.4	90	—	—	1.0	98	2500	2500
64	Heptacosane	0.2	95	—	—	0.6	98	2700	2700
65	Nonacosane	—	—	—	—	0.5	95	2900	MS

Unknown	RI	m./z. (%)	A	B	C
Un-1	1037	136(24), 121(26), 107(24), 93(78), 79(38), 68(100), 53(24)	5.4	—	5.1
Un-2	1044	136(2), 121(12), 105(18), 93(100), 79(38), 67(12), 53(12)	0.6	—	—
Un-3	1087	136(6), 121(24), 93(68), 80(30), 71(100), 67(20), 55(56)	0.6	—	—
Un-4	1089	154(5), 136(12), 121(24), 93(74), 80(32),71(100), 55(54)	—	4.2	—
Un-5	1090	207(6), 114(8), 98(32), 82(32), 70(36), 57(100), 53(8)	0.6	—	—
Un-6	1179	135(7), 131(2), 128(100), 102(6), 75(4), 64(8), 51(8)	—	0.6	—
Un-7	1189	149(4), 136(45), 126(56), 90(66), 81(42), 67(20), 59(100)	—	0.8	—
Un-8	1190	152(5), 107(57), 91(55), 79(100), 67(20), 55(23)	—	—	2.1
Un-9	1195	152(3), 135(8), 107(44), 91(54), 79(100), 67(14), 53(14)	0.6	—	—
Un-10	1432	204(8), 161(100), 133(12), 119(20), 105(37), 91(36), 79(19)	0.8	0.7	—
Un-11	1516	204(20), 189(24), 161(40), 105(50), 98(100), 69(75), 55(48)	—	—	2.3
Un-12	1552	205(12), 177(25), 121(40), 91(80), 79(100), 69(60), 55(62)	—	—	2.6
Un-13	1599	220(4), 134(44), 119(99), 107(76), 93(100), 79(84), 71(12)	—	0.5	—
Un-14	1641	246(6), 205(20), 159(36), 119(100), 105(64), 91(88), 79(40)	—	0.9	—
Un-15	1685	220(43), 177(37), 159(92), 109(100), 91(95), 79(82), 55(66)	—		2.7
Un-16	1688	220(30), 159(80), 109(80), 91(100), 79(64), 67(46), 55(58)	0.7	—	—
Un-17	1847	268(4), 250(8), 109(30), 95(28), 85(32), 71(56), 58(100)	1.3	1.0	—
Un-18	1960	256(14), 223(20), 149(100), 129(40), 73(22), 57(18)	—		2.5
Un-19	2113	278(5), 226(5), 123(27), 95(16), 81(27), 71(100), 57(32)	1.0	—	—
Total			11.6	8.7	17.3

Total isolate	79.2	85.2	76.8
Total unknown	11.6	8.7	17.3
TOTAL	90.8	93.9	94.1

RI, retention index; LRI, literature retention index; tr, trace, less than 0.05%; Q, quality; A, T. chamaedrys. subsp. chamaedrys.; B, T. orientale. var. puberulens;. C, T. chamaedrys. subsp. lydium..

^a.Compounds are listed in order of elution. RI values are calculated from retention times relative to that of n.-alkanes (C₆–C₃₂) on the nonpolar HP-5 column.

Table 2. The chemical class distribution of the essential oil components of T. chamaedrys. subsp. chamaedrys., T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium..

	T. chamaedrys. subsp. Chamaedrys.		T. orientale. var. puberulens.		T. chamaedrys. subsp. lydium.
Compound class	% Area	Number of compounds	% Area	Number of compounds	% Area	Number of compounds
Monoterpenes	29.1	5	—	—	19.8	5
Monoterpenoids	0.2	1	2.9	6	0.8	3
Sesquiterpenes	41.8	15	53.5	15	42.3	12
Sesquiterpenoids	4.7	4	7.7	7	9.9	5
Diterpenoids	1.0	1	—	—	1.0	1
Others	2.4	10	21.1	7	3.0	7
The common compounds	42.0	11	54.2	11	46.9	11
Total isolate	79.2	36	85.2	35	76.8	33

Table 3. The major components in the chemical class distribution of the essential oil constituents of T. chamaedrys. subsp. chamaedrys., T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium..

	T. chamaedrys. subsp. chamaedrys.			T. orientale. var. puberulens.			T. chamaedrys. subsp. lydium.
Compound class	Major component	% Area	RI	Major component	% Area	RI	Major component	% Area	RI
Monoterpenes	α-Pinene	15.8	939	—	—	—	α-Pinene	12.5	939
Monoterpenoids	β-Cyclocitral	0.2	1222	α-Terpineol	0.9	1196	Carvacrol	0.5	1299
Sesquiterpenes	Germacrene D	16.7	1481	β-Caryophyllene	21.7	1424	β-Caryophyllene	19.7	1424
Sesquiterpenoids	Caryophyllene oxide	2.4	1585	Caryophyllene oxide	2.7	1585	Caryophyllene oxide	6.1	1585
Diterpenoids	cis.-Phytol	1.0	2113	—	—	—	cis.-Phytol	1.0	2113
Others	(E.)-2-Decenal	0.6	1263	2-Methyl cumarone	20.0	1188	Heptacosane	0.6	2700

RI, retention index.

Table 4. Screening results for antimicrobial activity of the essential oils from T. chamaedrys. subsp. chamaedrys., T. orientale. var. puberulens., and T. chamaedrys. subsp. lydium..

		Microorganisms and inhibition zone (mm)
Sample	Stock (µg/mL)	Ec	Yp	Kp	Sm	Ef	Sa	Bs	Ca	Ct
T. chamaedrys. subsp. chamaedrys.	1000	+	+ +	—	+	+	+	—	—	—
T. orientale. var. puberulens.	500	—	—	—	—	+ +	+	+	—	—
T. chamaedrys. subsp. lydium.	500	—	—	—	—	+	+ +	+ +	—	—
Ceftazidime	10	+ + +	+ + +	+ + +	+ + +	+ + +	+ + +	+ + +
Triflucan	5								+ + +	+ + +

Results were interpreted in terms of the diameter of the inhibition zone. (−): < 5.5 mm; (+): 5.5–10 mm; (+ +): 11–15 mm; (+ + +): ≥ 16 mm.

Ec, Escherichia coli. ATCC 35218; Yp, Yersinia pseudotuberculosis. ATCC 911; Kp, Klebsiella pneumoniae. ATCC 13883; Sm, Serratia marcescens. ATCC 13880; Ef, Enterococcus faecalis. ATCC 29212; Sa, Staphylococcus aureus. ATCC 25923; Bs, Bacillus subtilis. ATCC 6633; Ca, Candida albicans. ATCC 60193; Ct, Candida tropicalis. ATCC 13803. Ceftazidime and triflucan are used as antibacterial and antifungal standards, respectively.