Flowering phenophases influence the antibacterial and anti-biofilm effects of Thymus vulgaris L. essential oil

Bakó, Csongor; Balázs, Viktória Lilla; Kerekes, Erika; Kocsis, Béla; Nagy, Dávid U.; Szabó, Péter; Micalizzi, Giuseppe; Mondello, Luigi; Krisch, Judit; Pethő, Dóra; Horváth, Györgyi

doi:10.1186/s12906-023-03966-1

BMC Complementary Medicine and Therapies

Table 3 List of terpene and terpenoid compounds detected in TEOs prepared from fresh and dried plant materials and collected at different flowering phenophases. Quantities are expressed as relative abundance (area %)

From: Flowering phenophases influence the antibacterial and anti-biofilm effects of Thymus vulgaris L. essential oil

Compounds	MS Sim (%)	LRI _Exp	LRI _Ref	T2	T4	T5	T6
Tricyclene	94	922	923	0.02	0.01	0.01	0.02
α-Thujene	98	925	927	1.09	0.46	0.21	0.37
α-Pinene	97	933	933	0.63	0.50	0.37	0.55
Camphene	97	949	953	0.39	0.33	0.25	0.42
Sabinene	95	972	972	0.02	0.01	0.01	0.01
Pent-4-enyl propanoate	94	974	974	0.01	0.04	0.01	0.01
β-Pinene	92	977	978	0.20	0.15	0.12	0.15
Vinyl amyl carbinol	95	979	978	0.34	0.36	0.34	0.51
Octan-3-one	93	984	986	0.03	0.04	0.02	0.03
Myrcene	96	988	991	1.34	1.17	0.71	0.84
Octan-3-ol	96	997	999	0.03	0.02	0.02	0.03
α-Phellandrene	96	1006	1007	0.12	0.13	0.08	0.08
δ-3-Carene	96	1009	1009	0.08	0.07	0.05	0.06
α-Terpinene	98	1017	1018	1.09	1.15	0.74	0.79
p-Cymene	96	1025	1025	17.44	12.46	15.02	22.78
Limonene	96	1029	1030	0.30	0.27	0.22	0.31
β-Phellandrene	94	1030	1031	0.10	0.08	0.08	0.11
Eucalyptol	97	1032	1032	0.70	0.50	0.67	0.90
(Z)-, β-Ocimene	90	1034	1035	0.01	0.01	0.00	0.01
(E)-, β-Ocimene	95	1045	1046	0.02	0.04	0.02	0.02
γ-Terpinene	95	1058	1058	7.38	13.67	5.06	5.49
3-Methylbut-2-enyl butanoate	90	1063	1068	0.06	0.06	0.05	0.05
(Z)-Sabinene hydrate	93	1070	1069	0.33	0.21	0.31	0.21
Terpinolene	96	1086	1086	0.09	0.10	0.10	0.11
p-Cymenene	94	1091	1093	0.02	0.02	0.03	0.05
Linalool	97	1099	1101	1.56	1.69	1.67	2.17
(E)-Sabinene hydrate	94	1102	1099	0.13	0.10	0.14	0.11
3-Methylbut-3-enyl 3-methylbutanoate	90	1110	1114	tr	tr	0.01	0.02
(Z)-, p-Menth-2-en-1-ol	96	1126	1124	0.03	0.03	0.04	0.05
Camphor	97	1149	1149	0.25	0.26	0.29	0.33
Borneol	98	1173	1173	0.44	0.49	0.51	0.85
Terpinen-4-ol	92	1182	1184	0.75	0.67	0.67	0.87
Hex-(3Z)-enyl-Butyrate	92	1184	1187	0.03	0.03	0.04	0.04
p-Cymen-8-ol	93	1189	1189	0.04	0.04	0.05	0.08
α-Terpineol	97	1197	1195	0.15	0.13	0.16	0.21
(Z)-, Dihydro-carvone	94	1200	1198	0.05	0.05	0.06	0.07
n-Decanal	95	1206	1208	0.01	0.01	nd	nd
Thymol methyl ether	94	1230	1229	0.50	0.57	0.43	0.53
Carvacryl methyl ether	96	1239	1239	0.36	0.35	0.32	0.32
Neral	96	1242	1238	0.01	0.01	0.01	0.01
Carvone	95	1249	1246	0.02	0.02	0.01	0.02
Geranial	97	1274	1268	0.02	0.02	0.01	0.02
Thymol	94	1294	1293	57.10	56.39	62.46	52.33
Carvacrol	94	1302	1300	2.92	2.98	3.48	3.11
Thymol acetate	93	1345	1348	0.02	0.03	0.01	nd
Eugenol	95	1354	1357	0.09	0.02	0.01	0.05
α-Ylangene	92	1371	1371	nd	0.02	0.02	0.02
Isobornyl propionate *	93	1376	1377	0.04	0.07	0.09	0.10
α-Copaene *	88	1377	1375	0.04	0.07	0.09	0.10
β-Bourbonene	95	1385	1382	0.03	0.03	0.04	0.06
(Z)-Jasmone	93	1394	1394	0.01	tr	0.01	tr
(E)-Caryophyllene	97	1421	1424	2.05	2.15	2.50	2.44
β-Copaene	94	1431	1433	0.02	0.03	0.03	0.03
Aromadendrene	94	1441	1438	nd	0.04	0.01	0.01
α-Humulene	97	1457	1454	0.06	0.07	0.07	0.07
(Z)-Muurola-4(14),5-diene	94	1464	1466	0.01	0.01	0.01	tr
Geranyl propanoate	97	1468	1471	0.05	0.08	0.07	0.06
Cadina-1(6),4-diene	91	1473	1474	nd	0.01	0.02	tr
γ-Muurolene	92	1476	1478	0.07	0.14	0.14	0.12
α-Amorphene	90	1481	1482	0.01	0.02	0.02	0.02
Germacrene D	95	1482	1480	0.07	nd	nd	nd
β-Selinen	94	1491	1492	0.01	0.01	0.01	0.01
γ-Amorphene	87	1494	1490	0.02	0.06	0.05	0.04
α-Selinene	89	1497	1501	0.01	0.01	0.02	0.02
α-Muurolene	93	1500	1497	0.03	0.05	0.06	0.05
δ-Amorphene	89	1505	1506	nd	0.02	0.01	tr
γ-Cadinene	95	1515	1512	0.12	0.16	0.24	0.17
δ-Cadinene	94	1520	1518	0.13	0.26	0.27	0.22
(E)-Calamenene	90	1522	1527	0.04	0.03	0.07	0.06
(E)-Cadina-1,4-diene	93	1534	1536	0.01	0.02	0.02	0.02
α-Cadinene	95	1539	1538	0.01	0.02	0.03	0.02
α-Calacorene	91	1543	1544	nd	tr	0.01	0.01
Geranyl butyrate	97	1554	1559	0.02	0.02	0.03	0.03
Caryophyllene oxide	93	1585	1587	0.37	0.52	0.70	0.70
Humulene epoxide II	89	1613	1613	0.01	0.01	0.02	0.01
1-,10-di-epi-Cubenol	89	1618	1614	0.02	0.01	0.03	0.01
epi-γ-Eudesmol	95	1626	1624	0.04	0.03	0.03	0.03
α-Cadinol	94	1645	1641	0.17	0.07	0.17	0.05
Cadin-4-en-10-ol	95	1658	1659	0.03	0.02	0.02	0.01
Not identified				0.22	0.26	0.30	0.51
Total				100.00	100.00	100.00	100.00

Abbreviations: MS Sim (%), mass spectral similarity; LRI _Exp, experimental linear retention index; LRI _Ref, reference linear retention index; nd, not detected; tr, trace level; * compounds coeluted on SLB-5-ms GC column. T2: TEO distilled from fresh plant material and collected in full bloom, T4: TEO distilled from dried plant material and collected at the beginning of flowering period, T5: TEO distilled from dried plant material and collected in full bloom, T6: TEO distilled from dried plant material and collected at the end of flowering period.

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