The present study focuses on the yield, chemical composition, and antioxidant activity of essential oils from the leaves and fruit of wild-grown bay laurel (Laurus nobilis L.) in Montenegro. The chemical composition of isolated essential oils was determined by GC/MS and GC/FID. Antioxidant activity was determined using the DPPH assay. The laurel bay essential oil (LEO) yield was 0.88% in fruits and 2.65% in the leaves. The results obtained from this study indicate that the LEOs obtained from the different plant parts (leaves, fruit) display different compositions. Fifty components were identified in LEO leaves, with 1,8-cineole (39.4%), linalool (13.9%), α-terpinyl acetate (11.2%), sabinene (6.7%), methyl eugenol (5.7%), β-pinene (3.2%), and α-pinene (3.1%) being the most abundant ones. Fifty-five components were isolated in LEO fruits with 1,8-cineole (34.2%), α-pinene (6.6%), sabinene (6.1%), β-bisabolene (5.8%), β-pinene (4.8), α-terpinyl acetate (4.5%), and α-terpineol (4.3%) as the main components. However, this study is the first to present the chemical composition of the LEO fruits from Montenegro. The results indicate that the composition of LEO is similar to recent studies from Balkan and Mediterranean areas. The degree of DPPH radical neutralization increased with the incubation time. The LEO isolated from leaves showed better antioxidant activity (EC50 value of 1.43 mg/mL) in comparison to the LEO isolated from fruits (EC50 value of 3.74 mg/mL) during the incubation time of 120 min. Taken together, this study indicates that the LEO from leaves and fruits possesses significant antioxidant activities (possibly due to the high level of 1,8-cineole) and is an important component in the food and pharmaceutical industries. All plant parts of L. nobilis can be successfully used in LEO extraction and isolation.

Keywords:

Subject: Biology and Life Sciences - Food Science and Technology

1. Introduction

Laurus nobilis L. (Lauraceae) is mentioned in the literature as bay leaves, Grecian laurel, sweet bay, true bay, bay laurel or simply bay, grown in native as evergreen spontaneous, wild plants from the Mediterranean Region with moderate and subtropical climate (Montenegro, Croatia, Albania, Greece, Tunis, Morocco, Algeria, Egypt, Turkey, etc.) [1]. Production on larger areas in the tropical region can be met in the Central America, Middle East, and Asia [2]. In ancient times, the laurel was considered a symbol of glory, victory, and progress and had a mainly decorative role. The people believed that it had protective power against lightning strikes, so it was grown near homes [3]. As a flavoring agent, dry bay leaves are added to cooked meat and fish, and added in cabbage, bean and tomato dishes or soups [3] according to Mediterranean recipes [4], while black berries are added to vinegar or different beverages. As a well-known culinary and spice plant, it is most common in Turkish, Indian, Italian, and French cuisine [2]. The major bay producer and highest exporter in the world was Turkey (97% of the world’s total production, with 7500 tons) [5].

In herbal medicine, bay leaf is an accepted practice of several infectious diseases and respiratory problems. It is good for treating diabetes, helps fight inflammation, reduces the risk of cancer, prevents the development of fungal infections, speeds up wound healing, and improves skin health. Flavor of bay leaf is considered astringent and bitter and aroma recalling between oregano and thyme with evident scent of menthol and eucalyptus when crushed [6]. The chemical profiles of the leaf can be conditional vary by origin, agro-ecological conditions, time of harvest, and extraction methods [2].

The antioxidant properties of L. nobilis leaves are based on the presence of phenolic compounds, lactones and various components of essential oils [7]. The content of these compounds and individual components of EO depends on a number of factors such as edaphic, pedological, climatic, orographic [8]. Seasonal variation of the EO content of laurel has been established, so that the EO content is always the highest in autumn and the smallest quantity and quality of EO is achieved in spring. The age of the plant and certain parts of the plant affect the EO content. Thus, young plants and shoots and old leaves achieve the highest oil content [9].

The content of essential oils in the leaves of L. nobilis is strongly influenced by geographical location. Thus, in northern populations, the content of essential oils is higher than in southern ones. Similar observations were made in populations from the west, which are characterized by a lower EO content compared to populations in eastern positions [10]. Cultivated laurel had a high content of terpenes such as linool, α -terpinol, α-terpinyl acetate, thymol, caryophyllene, aromandrene, selinene, farnesene, and cadinene, while wild laurel had a high content of eugenoland methyl eugenol, vitamin E, and sterols [11].

The EO content is different in individual plant parts. The content is higher in the leaves than in the fruits. Petkova et al. [12] have published research on the composition of EO from the fruits of L. nobilis originating from Greece and Georgia. These two countries rely on two different seas, the Aegean Sea and the Black Sea, with quite different climatic conditions at similar latitudes but different longitudes. Since the countries are quite far away and have different climates, the leaves and berries were collected spontaneously from plants that grew wild. The EO content in the leaves ranges from 1 to 3%, while the EO content in the fruit is within wide limits and ranges from 0.7% to 3% in the pericarp of the fruit, while it is around 1.2% in the hulls [11]. This relatively wide range for laurel fruit EO content may be due to different climatic conditions and the plant parts processed. Significant differences were observed in the composition of EO in L.nobilis growing wild in nature and that which was cultivated. Cultivated laurel had a high content of terpenes such as linool, α-terpinol, α-terpinyl acetate, thymol, caryophyllene, aromandrene, selinene, farnesene, and cadinene, while wild laurel had a high content of eugenol and methyl eugenol, vitamin E, and sterols. [12].

Various plant parts can be use for extraction of BLEO mainly composed of 1,8-cineole, sabinene, α-pinene, and p-cymene [13]. 1,8-cineole or eucalyptol being predominant compounds of BLEO from the leaves [6], but often include in small amount α-terpinyl acetate, α-pinene, sabinene, and linalool [5,14,15]. BLEO is used in the flavoring industry, mostly in aromatherapy [9], massage therapy, and cosmetics [3,5], but also to protect wheat grains against A. flavus durig storage [16] as fumigant, because possess repellent properties [17].

The present research aimed to compare the content, chemical parameters and antioxidant activity of the EOs isolated from different part of bay laurel grown in Montenegro.

2. Materials and methods

2.1. Plant material and growing conditions

A tress of buy laurel from the local forest 'Dubrava' part of Herceg Novi (with the coordinates of 42°27′05″N 18°32′13″E), in Adriatic cost of Montenegro was collected by hand or scissors, from the vegetation period during 2021 and 2022.

The laurel plant can be a shrub up to 1 m in height or it can grow in the form of a tree with a single trunk that reaches a height of up to 20 m. The leaves are leathery, glossy, lanceolate or spear-shaped, up to 5 cm long and up to 2 cm wide, with a petiole 0.5 cm long, with a smooth or toothed margin alternately arranged on the branches. The flowers are white, with a distinct smell, four-parted, with 8-12 stamens, with a 2-4 parted ovary. The fruit is a berry with a thin pericarp, which contains light green seeds arranged in loose clusters. When ripe, the fruit is black.

Bay leaves (lanceolate with smooth or sharp margins), can be harvested throughout the year because the plant is evergreen. Leaves are generally collected after flowering stage, when they reach full volatiles components. The fruit is a small, shiny black berry-with one seed inside the fruit. The leaves and fruits are kept in a cool and dry place (10–15°C and 55–65% relative humidity).

2.2. Clevenger-type hydrodistillation

Disintegrated and homogenized plant material: Laurus nobilis L. (leaves and fruits) was used for EO isolation by Clevenger-type hydrodistillation with hydromodulus (ratio of plant material to water) 1:10 m/V during 120 min. The details with an extended explanation are given in Stanojevic et al. [18]. The chemical composition of essential oils has been studied in three replication.

2.3. Antioxidant activity (DPPH assay)

The ability of the EOs to scavenge free DPPH radicals was determined using the DPPH assay. The details of the method used are given in Stanojevic et al., [18]. The details of the gas chromatography-mass spectrometry (GC/MS) and gas chromatography-flame ionization detection (GC/FID) analyses used are given in our previous research by Milenković et al. [19] and Ilić et al. [20].

2.4. Statistical analysis

The results of EO yield and antioxidant activity are compared using one-way ANOVA and Duncan’s multiple range tests.

3. Results and discussion

3.1. Essential oil yield

The bay laurel essential oil (LEO) yield was 0.88% in fruits and 2.65% in the leaves (Figure 1). The results indicate that the yield of L. nobillis leaves and fruit is similar to recent studies from Balkan and Mediterranean areas.

The yield of EOs from different plant parts of laurel bay in research from the same region (Montenegro sea-side) was as follows: 0.7%, 1.4% and 1.5% in stems, young shoots and leaves, respectively [21]. In earlier exploration, Kovačević [22] reported that content of LEO leaves from Montenegro achieved 1–3%.

In Meditarean countries, the BLEO yield was lower than in our explorations. Thus, the extractive yield of the BLEO from Algeria was 1.13% [16] or from Morocco laurel 1.06% [23] with 1.8-cineole as the most dominant compound. A different content of essential oils is noticeable depending on the plant part. So, the oil yields from Bulgarian bay was 0.78% in the fruits, 0.80% in twigs, and 3.25% in leaves [24] . EOs content from different plant part of L. nobilis from Tunisia was between 0.4 and 1.1% [25]. The content of the LEO fruits varied in range from 0.60 to 4.30% [25,26,27], or leaves content from 0.5 to 4.3% [26,28,29,30]. LEO yields from Argentina were 0.9% (v/w) of dry weight and decreased to 0.3% (v/w) at flower stage [31]. Leaves of L. nobilis from South Asia contained 0.8% to 3% EOs or fruits from 0.6% to 10% EOs [32].

The yield of LEO, among other things, also depends on the applied extraction method. Hydro-distillation-HD obtained a higher EO yield (1.40%) than other methods (hydro-steam distillation: 0.74%, microwave-assisted hydrodistillation: 1.00%, and ohmic-assisted hydrodistillation: 0.83% w/w), [33].

3.2. Leaves and fruits essential oil composition

In our study 1.8-cineole (39.4%), linalool (13.9%), α-terpinyl acetate (11.2%), sabinene (6.7%), methyl eugenol (5.7%), β-pinene (3.2%), α-pinene (3.1%) where the most abundant, as shown in Table 1.

The terpenic fraction included oxygen containing monoterpene derivatives (72.2%) with present on a larger scale 1.8-cineole (39.4%) and linalool (13.9%), and monoterpene hydrocarbons (15.6%) with the sabinene (6.7%) as main constituent. The phenylpropanoids (7.8%) represented by methyl eugenol (5.7%) were the least abundant (Table 1). (E)-anethole, 2-undecanone, (E)-γ-bisabolene, dehydro-aromadendrane and shyobunol were present only in laurel bay leaves, they are absent in berry fruits.

The most present components in bay laurel fruits were 1.8-cineole (34.2%), α-pinene (6.6%), sabinene (6.1%), β-bisabolene (5.8%) and β-pinene (4.8%) (Table 1).

The terpenic fraction included oxygen containing monoterpene derivatives which constitute 48.3% with the main components being 1.8-cineole (34.2%) and monoterpene hydrocarbons (24.2%) with the main constituent being α-pinene (6.6%) and sabinene (6.1%). The sesquiterpene hydrocarbons represented by β-bisabolene (5.8%) and the phenylpropanoids (7.8%) represented by methyl eugenol (5.7%) were the least abundant. Oxygen-containing sesquiterpenes (7%) contained khusinol (2.2%) and helifolenol A (1.9) as main components (Table 1).

Tricyclene, p-cymene, α-ylangene, 6,9-guaiadiene, neryl acetate, aromadendrene, γ-muurolene, cubebol, selina-3,11-dien-6-α-ol, 14-hydroxy-9-epi-(E)-caryophyllene and khusinol, were present only in the berry fruits.

Different researchers have studied the LEO composition. In many cases, the most present LEO components are 1.8-cineole and α-terpinyl acetate [35].

Different populations from Croatia, contained 1.8-cineole (from 38.94 % to 58.13%) and linalool (1.99 % - 18.33%) as main components and on a much smaller scale terpinyl acetate, methyl eugenol, α-terpineol, terpinen-4-ol, β-pinen, etc. [36].

Chromatogram of LEO from leaves and fruits are presented in Figure 2 and Figure 3.

1.8-cineole, α-terpinyl acetate, linalool, and sabinene, were the most dominant part of LEO leaves in research from different countries like Bulgaria, Argentina, Albania, Iran, Turkey, and Serbia [37]. Moroccan (45.01%) and Algerian (35.5%) bay leaves contained 1,8-cineole as the most abundant compound [16,23].

Our results agree with those reported by Marzouki and co-workers of LEO from Tunisia Algeria and France [32], and Algerian, Moroccan, and Tunisian LEOs, who presented as major components 1.8-cineole, linalool, α-terpinyl acetate [11] .

The compositions of the LEO from Tunisia, Algeria, and France similar to previous results from different countries stands out 1.8-cineole, alpha-terpinyl acetate (10-18.6%), methyl eugenol (10-22.1%), sabinene (1.2-8%) and eugenol (1.2-11.7%) showed a chemical polymorphism of three populations studied [38].

The Colombian LEO has lower content of 1,8-cineole (22.0%) than content of Spanish LEO (51.95%) [36,39]. LEO from India and Nepal was found to have linalool as a main component [40] or eugenol (44.13%) in Chinese origin [41].

The three main constituents from Italy [42], Iran [43], and Georgia [45]., are 1,8-cineole, α-terpinyl acetate and sabinene. In the LEO from Bulgaria, 1,8-cineole, α-terpinyl acetate, and α-pinene are the main constituents [38] or LEO from Greece contained 1,8-cineole, α-terpinyl acetate, and α-terpineol [44].

1,8-cineol (41.1%), sabinene (6.96%), α-pinene (5.94%), and α-terpinenyl acetate (5.72%) are the main compounds in LEO from the Turkey [46] while in North-West Algerian LEO the most present constituents are 1,8-cineole (30.1%), α-terpynil acetate (21.6%), and methyl eugenol (16.9%) [47]. LEO from South Turkey contained higher percentages of 1,8-cineole (46.6-59.9%) [48].

The most abundant compounds in LEO from Albania were: eucaliptol (41.8 – 48.2%) > linalool (8.8 – 11.9%) > sabinene (8.9 – 11.7%) > terpinyl acetate (8.4 – 10.8%) > α-pinene (4.8 – 6.0%), etc. [49]. Eucalyptol (27.2%) also detected in main component in Portugal LEO [50]. Isoeugenol (53.5%, 57.0%) and linalool (42.61%) were the main compounds of LEOs from Brazil and India.

The major compounds of LEO from seeds collected in Turkey (Black Sea region) included eucalyptol (17.2%), α-terpinyl acetate (9.0%) and caryophyllene oxide (6.1%) [51].

Castilho et al. [52] reported that (E)-β-ocimene and germacrene D are the most common in Portuguese LEO. Similarly, (E)-β-ocimene in Tunisian LEO was found as a predominating fruit volatile [38]. Yahyaa et al. [53] analyzed different maturity stage of the fruit separately and found in green fruits (E)-β-ocimene as main component or 1,8–cineole, were abundant in black fruits.

The main constituents in the LEO fruit were 1,8-cineole (33.3%), α-terpinyl acetate (10.3%) and α-pinene (11.0%)[30]. 1.8-cineol (44.72%), α-terpinyl acetate (12.95%), and sabinene (12.82%) were the main components in bay laurel from Turkey [55]. Monoterpene hydrocarbons and oxygeneted monoterpenes were the main participants of antioxidant activity [54].

The composition of individual constituents of LEO determines their biological activity and varies widely depending on genotypes, environmental factors, and individual parts of the plant, age of the plant and time of harvest. Because it is of particular importance that when using EOs in the food industry, in order to preserve its integrity and quality, the exact chemical composition and standards are determined, that will be strictly respected.

3.3. Antioxidant activity (AA)

Oxygen-containing monoterpenes are the main chemical constituents of LEO largely because of their functional groups with oxygen inside the structure. The LEO isolated from leaves showed stronger antioxidant activity (EC₅₀ value of 1.43 mg/mL) than LEO isolated from the fruits (EC₅₀ value of 3.74 mg/mL), (Figure 4).

The strong free DPPH radical scavenging capacity of the LEO may be due to present of high level 1,8-cineole (45.01%) and other chemical compounds like and α-caryophyllene, germacradienol, limonene and others [23].

LEO from seeds and leaves exhibited a scavenging effect on the DPPH radical, with EC₅₀ values of 66.1 and 53.5 µg mL^–1, respectively [55]. EC₅₀ values were the highest value for LEO (EC₅₀ value of 135 µg/mL) than positive control BHT (EC₅₀ value of 11.5 µg/mL) [56].

Turkish L. nobilis EO gave an EC₅₀ of 59.2 μg/ml. LEO leaves from Turkey was found to have lower reducing activity compared to the synthetic antioxidants - butylated hydroxytoluene (BHT) and ascorbic acid [57]. In contrast, the LEO extracted from the floral buds of plants from Tunisia, with α-terpinyl acetate and methyl eugenol as predominant EO was found to manifest a higher AA than BHT [58].

These differences in EC₅₀ can be attributed to analytical methodologies and to the several factors influencing the chemical composition of EO such as the variety, plant growth conditions, EO storage conditions, and the extraction methods used. [57].

The present differences in EC₅₀ values found in the literature are the result of the application of different chemical methods in analysis as well as numerous factors that greatly influence the content and composition of EO such as variety and population, geographical origin, environmental conditions in which plants develop and grow, time and harvesting methods, drying methods, as well as extraction methods.

The chemical composition, especially individual components, determines the biological activity of EO, and especially some of the main compounds. Numerous studies confirm that small-scale compounds can interact with each other directly, or in a synergistic or antagonistic manner, to create a mixture that is biologically active. In the literature, we find several compounds that are characterized by strong antioxidative properties, such as: linalool and 1,8-cineole, terpen-4-ol, α-pinene and β-pinene. Their antioxidant properties are an expression of the interaction between bioactive molecules and other components of the food matrix, in the form of a synergistic or antagonistic effect. This involves the identification, isolation and quantification of biologically active compounds, followed by the evaluation of their interactions. The development of natural EOs as biopreservatives in the plant-based food industry will be of increasing importance in the near future.

Bioavailability testing for applications in functional foods and supplements is extremely important, since the abundance of polyphenols does not necessarily mean the best bioavailability profile [59,60]. Since laurel is a wild plant that is widely planted in the nature of the coast in Montenegro, and that EOs can be obtained relatively cheaply, new perspectives are opened in multidisciplinary research and development (R&D) of sustainable, efficient and economic procedures that would result in maximum using the great potential that L. nobilis is distinguished.

4. Conclusion

The laurel bay essential oil (LEO) yield was 0.88% in fruits and 2.65% in the leaves. 1,8-cineole (39.4-34.2%) is the main component in both plant parts (leaves and fruits). Fifty-five components were isolated in LEO fruits, with 1,8-cineole (34.2%), α-pinene (6.6%), sabinene (6.1%), β-bisabolene (5.8%), β-pinene (4.8), α-terpinyl acetate (4.5%), α-terpineol (4.3%) as the main components. The LEO isolated from leaves showed better antioxidant activity (EC₅₀ value of 1.43 mg/mL) in comparison to the LEO isolated from fruits (EC₅₀ value of 3.74 mg/mL). LEO from leaves and fruits possesses significant antioxidant activities (possibly due to the high level of 1,8-cineole) and is an important component in the food and pharmaceutical industries. All plant parts of L. nobilis can be successfully used in LEO extraction and isolation.

Author Contributions

Z.S.I. and L.S., heads of the research group, planned the research, analyzed, and wrote the manuscript; L.M. and L.Š. conducted the experiment in the field; J.S., B.D., and D.C. performed statistical analyses.

Funding

This research was funded by the Ministry of Education Science and Technological Development of the Republic of Serbia with grant numbers 451-03-47/2023-01/200133 and 451- 344 03-47/2023- 01/200189.

Data Availability Statement

All data are available in the manuscript file.

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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Figure 1. The dependence of the yield of laurel leaves and fruits essential oil obtained after 120 min of hydrodistillation (hydromodule 1:10 m/v)

Figure 2. GC/FID chromatogram of bay laurel (Laurus nobilis L.) leaves essential oil.

Figure 3. GC/FID chromatogram of laurel (Laurus nobilis L.) fruits essential oil.

Figure 4. Antioxidant activity of laurel leaves and fruits essential oil.

Table 1. Chemical composition of laurel leaves and fruits essential oil.

No.	t_ret, min	Compound	RI^exp	RI^lit	Method of identification	Content, %
No.	t_ret, min	Compound	RI^exp	RI^lit	Method of identification	leaves	fruits
1.	6.37	Tricyclene	922	921	RI, MS	-	tr
2.	6.46	α-Thujene	925	924	RI, MS	0.3	0.3
3.	6.67	α-Pinene	932	932	RI, MS, Co-I	3.1	6.6
4.	7.12	Camphene	947	946	RI, MS	0.3	1.3
5.	7.86	Sabinene	973	969	RI, MS	6.7	6.1
6.	7.97	β-Pinene	977	974	RI, MS, Co-I	3.2	4.8
7.	8.36	Myrcene	990	988	RI, MS	0.8	0.9
8.	8.70	Isobutyl 2-methylbutyrate	1002	1004	RI, MS	tr	tr
9.	8.88	α-Phellandrene	1007	1002	RI, MS	0.1	1.6
10.	9.05	δ-3-Carene	1011	1008	RI, MS	0.1	1.0
11.	9.28	α-Terpinene	1017	1014	RI, MS	0.2	0.2
12.	9.51	p-Cymene	1023	1020	RI, MS	-	0.2
13.	9.64	o-Cymene	1027	1022	RI, MS	0.2	0.3
14.	9.87	1.8-Cineole	1033	1026	RI, MS, Co-I	39.4	34.2
15.	10.39	(E)-β-Ocimene	1047	1044	RI, MS	tr	0.3
16.	10.82	γ-Terpinene	1058	1054	RI, MS	0.5	0.4
17.	11.30	cis-Sabinene hydrate	1071	1065	RI, MS	0.4	0.2
18.	11.95	Terpinolene	1089	1089	RI, MS	0.1	0.2
19.	12.65	Linalool	1105	1095	RI, MS, Co-I	13.9	1.8
20.	13.48	cis-p-Menth-2-en-1-ol	1127	1118	RI, MS	tr	tr
21.	15.45	δ-Terpineol	1172	1162	RI, MS	0.6	0.6
22.	15.80	Terpinen-4-ol	1182	1174	RI, MS, Co-I	1.7	1.1
23.	16.43	α-Terpineol	1196	1186	RI, MS, Co-I	3.7	4.3
24.	17.97	Neral	1234	1235	RI, MS, Co-I	0.2	-
25.	18.55	Carvone	1249	1239	RI, MS	tr	-
26.	18.87	Linalool acetate	1255	1254	RI, MS, Co-I	0.2	-
27.	20.16	Isobornyl acetate	1285	1283	RI, MS	0.2	1.3
28.	20.43	(E)-Anethole	1291	1282	RI, MS, Co-I	0.1	-
29.	20.55	2-Undecanone	1294	1293	RI, MS	0.2	-
30.	21.50	δ-Terpinyl acetate	1317	1316	RI, MS	0.5	0.1
31.	22.94	α-Terpinyl acetate	1351	1346	RI, MS	11.2	4.5
32.	23.53	Neryl acetate	1364	1359	RI, MS	-	0.3
33.	23.75	α-Ylangene	1370	1373	RI, MS	-	0.2
34.	23.53	Eugenol	1365	1356	RI, MS	1.7	-
35.	23.96	α-Copaene	1375	1374	RI, MS	-	0.2
36.	24.54	β-Cubebene	1389	1387	RI, MS	-	0.5
37.	24.66	β-Elemene	1392	1389	RI, MS	0.3	2.8
38.	25.35	Methyl eugenol	1409	1403	RI, MS	5.7	0.7
39.	25.77	(E)-Caryophyllene	1419	1417	RI, MS, Co-I	0.4	1.2
40.	26.48	α-Guaiene	1437	1437	RI, MS	0.1	0.5
41.	26.66	6,9-Guaiadiene	1442	1442	RI, MS	-	0.2
42.	26.91	Aromadendrene	1448	1439	RI, MS	-	0.3
43.	27.17	α-Humulene	1454	1452	RI, MS	tr	0.6
44.	27.81	dehydro-Aromadendrane	1470	1460	RI, MS	0.1	-
45.	28.07	9-epi-(E)-Caryophyllene	1474	1464	RI, MS	-	0.4
46.	28.28	γ-Muurolene	1482	1478	RI, MS	0.1	1.4
47.	28.49	β-Selinene	1487	1489	RI, MS	-	0.6
48.	28.86	Bicyclogermacrene	1496	1500	RI, MS	0.5	2.9
49.	29.23	β-Bisabolene	1506	1505	RI, MS	0.7	5.8
50.	29.59	γ-Cadinene	1515	1513	RI, MS	0.1	0.3
51.	29.75	Cubebol	1519	1514	RI, MS	-	0.8
52.	29.89	δ-Cadinene	1523	1522	RI, MS	0.1	0.8
53.	30.07	Myristicin	1527	1517	RI, MS	tr	1.1
54.	30.60	(E)-γ-Bisabolene	1539	1529	RI, MS	0.1	-
55.	30.77	α-Calacorene	1545	1544	RI, MS	-	0.2
56.	31.28	Elemicin	1559	1555	RI, MS	0.1	-
57.	32.08	Germacrene D-4-ol	1580	1574	RI, MS	0.1	0.8
58.	32.23	Caryophyllene oxide	1584	1582	RI, MS	0.6	0.2
59.	34.72	Selina-3,11-dien-6-α-ol	1650	1642	RI, MS	-	0.2
60.	34.93	β-Eudesmol	1656	1649	RI, MS	-	tr
61.	35.06	14-hydroxy-9-epi-(Z)-Caryophyllene	1660	1668	RI, MS	0.5	0.2
62.	35.41	14-hydroxy-9-epi-(E)-Caryophyllene	1670	1668	RI, MS	-	0.1
63.	35.73	Helifolenol A	1678	1674	RI, MS	0.1	1.9
64.	35.91	Khusinol	1683	1679	RI, MS	-	2.2
65.	36.43	Shyobunol	1697	1688	RI, MS	0.3	-
					Total identified (%)	100.0	100.0
	Grouped components (%)
	Monoterpene hydrocarbons (1-6, 8-11, 13, 14, 16)					15.6	24.2
	Oxygen-containing monoterpenes (12, 15, 17-25, 28, 29)					72.2	48.3
	Sesquiterpene hydrocarbons (31, 33-41, 43)					2.6	18.7
	Oxygen-containing sesquiterpenes (45-50)					1.6	7.0
	Phenylpropanoids (26, 30, 32, 42, 44)					7.8	1.8
	Others (7, 27)					0.2	tr

t_ret.: Retention time; RI^lit-Retention indices from literature (Adams,³⁴); RI^exp: Experimentally determined retention indices using a homologous series of n-alkanes (C₈-C₂₀) on the HP-5MS column. MS: constituent identified by mass-spectra comparison; RI: constituent identified by retention index matching; Co-I: constituent identity confirmed by GC co-injection of an authentic sample; tr = trace amount (<0.05%).

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Chemical Profiles and Antioxidant Activities of Essential Oil from Different Plant Parts of Bay Laurel (Laurus nobilis L.)

Abstract