Essential Oils from Phlomis longifolia Boiss. & C.I. Blanche. Aerial Parts (Flowers,Calyxes,Leaves): GC-MS Analyzes and Biological Properties

Abstract

Objective/Background: Phlomis longifolia Boiss. & C.I. Blanche. is one of the significant medicinal plants extensively utilized in folk medicine in Syria. So, this study aimed to identify the chemical components with potential pharmacological properties of essential oils extracted from the aerial parts of the Syrian P. longifolia plant for the first time. Methods: The aerial parts of the plant were collected from a mountainous area in Latakia Province, Syria. Subsequently, the essential oils were obtained using hydrodistillation with a yield of (0.14% for flowers, 0.075% for calyxes, and 0.19% for leaves) using a Clevenger-type apparatus and analyzed by gas chromatography coupled with mass spectrometry (GC-MS). Results: A total of 63, 61, and 48 compounds, which represent (98.0%, 97.1%, and 97.9%) of the total oils, were identified for flowers, calyxes, and leaves, respectively. The major compounds identified in the flower's essential oil were: widdrol (29.8%), β-caryophyllene (9.7%), and (E)-nerolidyl acetate (5.8%). While in the calyx's essential oil were: (E)-nerolidyl acetate (8.6%), α-humulene (8.1%), and β-caryophyllene (7.7%). As for the leave's essential oil were: (E)-nerolidyl acetate (11.4%), β-caryophyllene (9.5%), α-amorphene (8.8%), caryophyllene oxide (6.7%), α-humulene (5.3%), and 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (5.2%). Additionally, the majority of the identified compounds have various biological activities, according to the published literature. Conclusion: In this work, the chemical composition of essential oils extracted from the aerial parts of P. longifolia was determined for the first time by GC-MS. Terpenes were the dominant chemical content of essential oils (83.3% for flowers, 72.7% for calyxes, and 80.9 for leaves), and sesquiterpenes had the highest concentration among them (77.3% for flowers, 65.7% for calyxes, and 77.1% for leaves). These compounds are known for their diverse biological activities and promote the use of such plants in phytopharmaceuticals.

Keywords

Widdrol E-Nerolidyl acetate β-Caryophyllene Essential oils biological activity terpenoids

Introduction

Plants were widely used in folk medicine all over the world, which was predicated on centuries-old customs and beliefs. They are part of the tradition of every country and involve practices that have been passed down from generation to generation as folk medicines and have finally developed as modern medicinal treatments after scientific analysis of their effects.¹

Historically, the plant kingdom has been a rich source of novel lead compounds that contribute to a variety of pharmacological and therapeutic activities. Around 25% of pharmaceutical drugs in the modern era were derived from plants.²

However, due to the numerous intrinsic difficulties associated with isolating and identifying pharmaceuticals derived from natural products, most pharmaceutical companies have shifted their focus toward synthetic molecules as a source of new drugs because of their effectiveness and ease of production. Unfortunately, the low rate of new drugs entering the pharmaceutical market, together with unanticipated negative side effects, contraindications, and interactions between synthetic drugs, fell short of aspirations for global health^3-7. Additionally, as consumers’ knowledge of nutrition and health issues, as well as the potential and benefits of medicinal plants and their metabolites, increased, so did their interest in and demand for medicinal plants for use in food, medicine, and other applications.⁸ The World Health Organization estimated that around 80% of people worldwide use medicinal plant products to treat an array of diseases.⁹ It has confirmed the necessity of using modern technologies and proper standards to ensure the quality of medicinal plant products.¹⁰ Consequently, global attention once again shifted to the development of drugs based on natural products. So there have been an increasing number of publications on medicinal plants used in folk medicine as a significant approach to developing novel drugs.¹¹

Phlomis longifolia Boiss. & C.I. Blanche. belongs to the genus Phlomis and is a large genus in the family Lamiaceae, with more than 100 species distributed throughout the continents of Europe, Asia, and North Africa.¹² It is an herbaceous plant with entire, opposite, crossed, and wrinkled dark green leaves. Whorls of bright yellow flowers are arranged around the stems, which are typically square in section with rounded corners, though tomentum on stems can give the appearance that they are circular. The calyx is tubular and has five visible veins. It has five teeth, all of which are equal. The flowering period is from May to July. It grows in forests and grasslands. It is native to Syria, Lebanon, Turkey, and Cyprus, and is spread in Europe and North Africa.¹³ Its flowers are sweet and are consumed directly through sucking, which is why it is locally called the Al-Masas plant.

Plants from the genus Phlomis are frequently used in traditional medicine across the globe. They are used as a boiling or soaking herbal tea to treat fever, cough, and colds, as well as stomach, intestinal, and abdominal pain and digestive issues, and as a sedative.^14–18 They can also be applied as pastes or powders to treat burns, wounds, and skin diseases^19-21. Locally, P. longifolia flowers are used to treat stomach pain and indigestion. The plant's leaves and calyxes are also used to treat diabetes and kidney stones. Additionally, one of the most popular applications of the plant's leaves is to clean cooking utensils of dirt that has accumulated on them.

Despite P. longifolia's numerous medical applications, there aren't many investigations of the plant's chemical composition. Therefore, the aim of this work was to identify the chemical components with potential pharmacological properties of essential oils extracted from the aerial parts of the Syrian P. longifolia plant using gas chromatography coupled to mass spectrometry (GC-MS) technology for the first time.

Results and Discussion

GC-MS Analysis of Essential Oils

The hydrodistillation of aerial parts of P. longifolia produced yellowish oil with a yield of 0.14%, 0.075%, and 0.19% for flowers, calyxes, and leaves, respectively. A total of 63, 61, and 48 compounds (Tables 1, 2, and 3) were identified by GC-MS for both flowers, calyxes, and leaves, which represent 98.0%, 97.1%, and 97.9% of total oil, respectively. Moreover, the total ion chromatogram of the samples is shown in Fig. S1.

Table 1.

Chemical Composition of the Essential Oil Extracted from the Flowers of P. longifolia.

No	Name	RT(min)	M.F.	M.W.	Area%	Class
1	β-Linalool	5.839	C₁₀H₁₈O	154.25	$1.7 \pm 0.1$	M
2	3-Ethyl-o-xylene	6.600	C₁₀H₁₄	134.22	$0.4 \pm 0$	H
3	3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one	7.476	C₆H₈O₄	144.12	$2.0 \pm 0.2$	O
4	Vertonal	8.998	C₁₀H₁₆O	152.23	$0.2 \pm 0$	O
5	p-Cymen-8-ol	9.198	C₁₀H₁₄O	150.22	$0.2 \pm 0$	M
6	α-Terpineol	9.364	C₁₀H₁₈O	154.25	$0.2 \pm 0$	M
7	γ-Terpineol	9.656	C₁₀H₁₈O	154.25	$0.3 \pm 0.1$	M
8	5-Hydroxymethylfurfural	9.925	C₆H₆O₃	126.11	$3.5 \pm 0.3$	O
9	Geraniol	10.165	C₁₀H₁₈O	154.25	$1.0 \pm 0.1$	M
10	Carvacrol	10.359	C₁₀H₁₄O	150.22	$0.7 \pm 0.1$	M
11	α-Cubebene	10.777	C₁₅H₂₄	204.35	$1.5 \pm 0.1$	S
12	α-Longipinene	11.183	C₁₅H₂₄	204.35	$0.3 \pm 0$	S
13	. α-ylangene	11.241	C₁₅H₂₄	204.35	$0.4 \pm 0$	S
14	α-Copaene	11.349	C₁₅H₂₄	204.35	$0.9 \pm 0.1$	S
15	β-Bourbonene	11.630	C₁₅H₂₄	204.35	$0.4 \pm 0.1$	S
16	α-Funebrene	11.996	C₁₅H₂₄	204.35	$1.7 \pm 0.2$	S
17	α-Cedrene	12.202	C₁₅H₂₄	204.35	$0.9 \pm 0.1$	S
18	β-Caryophyllene	12.322	C₁₅H₂₄	204.35	$9.7 \pm 0.5$	S
19	α-Humulene	12.980	C₁₅H₂₄	204.35	$4.0 \pm 0.3$	S
20	γ –Gurjunene	13.438	C₁₅H₂₄	204.35	$0.3 \pm 0$	S
21	α-Amorphene	13.564	C₁₅H₂₄	204.35	$1.9 \pm 0.1$	S
22	Ledene	13.787	C₁₅H₂₄	204.35	$0.9 \pm 0.1$	S
23	α-Muurolene	13.907	C₁₅H₂₄	204.35	$0.3 \pm 0$	S
24	β-Bisabolene	14.039	C₁₅H₂₄	204.35	$0.7 \pm 0.1$	S
25	δ-Cadinene	14.359	C₁₅H₂₄	204.35	$1.5 \pm 0.1$	S
26	7-Isopropyl-4a-methyloctahydro-2(1H)-naphthalenone	14.542	C₁₄H₂₄O	208.34	$0.3 \pm 0$	S
27	Dehydronerolidol	15.034	C₁₅H₂₄O	220.35	$0.3 \pm 0.1$	S
28	Caryophyllene oxide	15.664	C₁₅H₂₄O	220.35	$2.7 \pm 0.3$	S
29	Widdrol	16.196	C₁₅H₂₆O	222.37	$29.8 \pm 1.6$	S
30	Geranyl isovalerate	16.528	C₁₅H₂₆O₂	238.36	$1.4 \pm 0.1$	M
31	τ-cadinol	16.825	C₁₅H₂₆O	222.37	$1.5 \pm 0.1$	S
32	Caryophylladienol II	17.094	C₁₅H₂₄O	220.35	$1.3 \pm 0.1$	S
33	Cubenol	17.472	C₁₅H₂₆O	222.37	$0.7 \pm 0$	S
34	α-Cadinol	17.712	C₁₅H₂₆O	222.37	$0.3 \pm 0$	S
35	Dehydro-Cyclolongifolene oxide	17.827	C₁₅H₂₂O	218.33	$0.4 \pm 0.1$	S
36	2-Methyl hexadecane	18.485	C₁₇H₃₆	240.47	$0.3 \pm 0$	H
37	Aromadendrene oxide-(1)	19.297	C₁₅H₂₄O	220.35	$1.4 \pm 0.1$	S
38	3-Hydroxy-5,6-epoxy-β-ionone	20.190	C₁₃H₂₂O₃	226.31	$1.0 \pm 0$	S
39	7,9-Dimethyl hexadecane	20.716	C₁₈H₃₈	254.5	$0.4 \pm 0.1$	H
40	Eudesm-11-en-1-ol	20.882	C₁₅H₂₆O	222.37	$0.2 \pm 0$	S
41	(Z)-14-Methyl-8-hexadecenal	21.512	C₁₇H₃₂O	252.4	$0.7 \pm 0.1$	O
42	(E,Z)-Farnesol	22.295	C₁₅H₂₆O	222.37	$0.3 \pm 0.1$	S
43	(E)-Nerolidyl acetate	22.604	C₁₇H₂₈O₂	264.40	$5.8 \pm 0.4$	S
44	Zerumbone	24.201	C₁₅H₂₂O	218.33	$0.6 \pm 0.1$	S
45	Neoisolongifolene-8-ol	24.315	C₁₅H₂₄O	220.35	$0.7 \pm 0.1$	S
46	Aristolene epoxide	24.544	C₁₅H₂₄O	220.35	$0.2 \pm 0$	S
47	Tetradecanoic acid	25.317	C₁₄H₂₈O₂	228.37	$1.7 \pm 0.1$	F
48	Hexahydrofarnesyl acetone	25.574	C₁₈H₃₆O	268.48	$1.8 \pm 0.1$	S
49	Corymbolone	27.102	C₁₅H₂₄O₂	236.35	$2.6 \pm 0.2$	S
50	Hexadecanoic acid, methyl ester	27.777	C₁₇H₃₄O₂	270.45	$0.2 \pm 0$	F
51	Phytol	28.601	C₂₀H₄₀O	296.5	$0.4 \pm 0.1$	D
52	Hexadecanoic acid	28.756	C₁₆H₃₂O₂	256.42	$0.3 \pm 0$	F
53	Dibutyl phthalate	29.780	C₁₆H₂₂O₄	278.34	$1.5 \pm 0.1$	O
54	Disparlure	30.352	C₁₉H₃₈O	282.5	$0.5 \pm 0.1$	O
55	10,13-Octadecadienoic acid, methyl ester	31.044	C₁₉H₃₄O₂	294.5	$0.2 \pm 0$	F
56	Henicosane	32.280	C₂₁H₄₄	296.6	$1.0 \pm 0.1$	H
57	(Z,Z,Z)-9,12,15-Octadecatrienoic acid, methyl ester	32.486	C₁₉H₃₂O₂	292.46	$0.5 \pm 0$	F
58	Octadecanoic acid	34.552	C₁₈H₃₆O₂	284.48	$0.2 \pm 0$	F
59	Docosane	34.638	C₂₂H₄₆	310.60	$0.4 \pm 0.1$	H
60	Agathadiol	35.095	C₂₀H₃₄O₂	306.50	$0.1 \pm 0$	D
61	Hexacosane	35.593	C₂₆H₅₄	366.71	$0.2 \pm 0$	H
62	Batilol	35.931	C₂₁H₄₄O₃	344.57	$0.2 \pm 0$	O
63	Octacosane	36.148	C₂₈H₅₈	394.76	$0.3 \pm 0$	H
	Total				98.0
	Hydrocarbons				3.0
		Aliphatic			2.6
		Aromatic			0.4
	Monoterpenes				5.5
		Hydrocarbon			-
		Oxygenated			5.5
	Sesquiterpenes				77.3
		Hydrocarbon			25.4
		Oxygenated			51.9
	Diterpenes				0.5
	Fatty acids & Esters				3.1
	Other oxygenated compounds				8.6

RT: Retention time (minutes), M.F.: Molecular formula, M.W.: Molecule weight, Area%: Percentage Peak Area, Class: Classification compound, H: Hydrocarbons, M: Monoterpenes, S: Sesquiterpenes, D: Diterpenes, F: Fatty acids & Esters, O: Other oxygenated compounds.

Table 2.

Chemical Composition of the Essential Oil Extracted from the Calyxes of P. longifolia.

No	Name	RT(min)	M.F.	M.W.	Area%	Class
1	β-Linalool	5.845	C₁₀H₁₈O	154.25	$0.9 \pm 0.1$	M
2	Pinan-2β-ol	6.623	C₁₀H₁₈O	154.25	$0.7 \pm 0.1$	M
3	3,6-Dimethyl decane	6.800	C₁₂H₂₆	170.34	$0.6 \pm 0$	H
4	3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one	7.510	C₆H₈O₄	144.12	$1.1 \pm 0.1$	O
5	γ-Terpineol	9.679	C₁₀H₁₈O	154.25	$0.8 \pm 0.1$	M
6	5-Hydroxymethylfurfural	9.947	C₆H₆O₃	126.11	$4.3 \pm 0.3$	O
7	2,7-Dimethyl-2,6-octadien-1-ol	10.199	C₁₀H₁₈O	154.25	$0.8 \pm 0$	M
8	Thymol	10.291	C₁₀H₁₄O	150.22	$0.9 \pm 0$	M
9	α-Cubebene	10.800	C₁₅H₂₄	204.35	$1.0 \pm 0.1$	S
10	Linalyl isobutyrate	11.275	C₁₄H₂₄O₂	224.34	$0.7 \pm 0.1$	M
11	Isoledene	11.378	C₁₅H₂₄	204.35	$0.8 \pm 0$	S
12	β-Panasinsene	11.590	C₁₅H₂₄	204.35	$0.8 \pm 0.1$	S
13	β-Maaliene	11.750	C₁₅H₂₄	204.35	$0.5 \pm 0$	S
14	α-Gurjunene	12.196	C₁₅H₂₄	204.35	$0.8 \pm 0.1$	S
15	β-Caryophyllene	12.328	C₁₅H₂₄	204.35	$7.7 \pm 0.5$	S
16	Trans-α-Bergamotene	12.637	C₁₅H₂₄	204.35	$0.8 \pm 0$	S
17	α-Humulene	13.014	C₁₅H₂₄	204.35	$8.1 \pm 0.5$	S
18	α-Curcumene	13.461	C₁₅H₂₂	202.33	$0.7 \pm 0$	S
19	τ-Elemene	13.592	C₁₅H₂₄	204.35	$4.6 \pm 0.4$	S
20	δ-selinene	13.770	C₁₅H₂₄	204.35	$3.9 \pm 0.3$	S
21	(E,E)-α-Farnesene	14.062	C₁₅H₂₄	204.35	$0.7 \pm 0$	S
22	δ-Cadinene	14.382	C₁₅H₂₄	204.35	$3.1 \pm 0.3$	S
23	α-Calacorene	14.559	C₁₅H₂₀	200.32	$0.5 \pm 0$	S
24	Caryophyllene oxide	15.675	C₁₅H₂₄O	220.35	$1.3 \pm 0.1$	S
25	Epiglobulol	15.790	C₁₅H₂₆O	222.37	$3.5 \pm 0.2$	S
26	Carotol	15.927	C₁₅H₂₆O	222.37	$3.8 \pm 0.3$	S
27	Widdrol	16.190	C₁₅H₂₆O	222.37	$1.3 \pm 0.1$	S
28	Geranyl isovalerate	16.528	C₁₅H₂₆O₂	238.36	$0.6 \pm 0$	M
29	Tetradecanal	16.694	C₁₄H₂₈O	212.37	$0.6 \pm 0$	O
30	τ-cadinol	16.825	C₁₅H₂₆O	222.37	$1.0 \pm 0.1$	S
31	Caryophylladienol II	17.106	C₁₅H₂₄O	220.35	$1.0 \pm 0$	S
32	Patchoulol	17.724	C₁₅H₂₆O	222.37	$0.8 \pm 0$	S
33	Aromadendrene oxide-(1)	19.303	C₁₅H₂₄O	220.35	$3.0 \pm 0.2$	S
34	Eudesma-4,11-dien-2-ol	20.213	C₁₅H₂₄O	220.35	$0.9 \pm 0$	S
35	7,9-Dimethyl hexadecane	20.745	C₁₈H₃₈	254.5	$0.7 \pm 0.1$	H
36	(Z)-14-Methyl-8-hexadecenal	21.512	C₁₇H₃₂O	252.4	$0.6 \pm 0$	O
37	(E,Z)-Farnesol	22.318	C₁₅H₂₆O	222.37	$0.5 \pm 0.1$	S
38	(E)-Nerolidyl acetate	22.622	C₁₇H₂₈O₂	264.40	$8.6 \pm 0.4$	S
39	Zerumbone	24.212	C₁₅H₂₂O	218.33	$0.5 \pm 0$	S
40	Aristolene epoxide	24.556	C₁₅H₂₄O	220.35	$0.6 \pm 0$	S
41	Tetradecanoic acid	25.334	C₁₄H₂₈O₂	228.37	$3.9 \pm 0.3$	F
42	Hexahydrofarnesyl acetone	25.597	C₁₈H₃₆O	268.48	$4.3 \pm 0.4$	S
43	Corymbolone	27.108	C₁₅H₂₄O₂	236.35	$0.6 \pm 0$	S
44	Phytol	28.630	C₂₀H₄₀O	296.5	$0.7 \pm 0.1$	D
45	Hexadecanoic acid	28.784	C₁₆H₃₂O₂	256.42	$0.6 \pm 0$	F
46	Linolelaidic acid, methyl ester	29.803	C₁₉H₃₄O₂	294.472	$0.7 \pm 0$	F
47	(Z)-Falcarinol	30.375	C₁₇H₂₄O	244.37	$1.0 \pm 0.1$	O
48	(E,E)-2,13-octadecadienol	30.569	C₁₈H₃₄O	266.46	$1.0 \pm 0.1$	O
49	Henicosane	32.303	C₂₁H₄₄	296.6	$0.6 \pm 0$	H
50	cis-6-Octadecenoic acid	32.509	C₁₈H₃₄O₂	282.46	$1.0 \pm 0$	F
51	8,11-Octadecadienoic acid, methyl ester	33.499	C₁₉H₃₄O₂	294.47	$0.6 \pm 0$ .	F
52	(Z,Z)-9,12-Octadecadienoic acid	33.648	C₁₈H₃₂O₂	280.44	$0.7 \pm 0.1$	F
53	13-Methyl-oxacyclotetradecane-2,11-dione	33.860	C₁₄H₂₄O₃	240.34	$0.6 \pm 0$	O
54	Mono(2-ethylhexyl) phthalate	34.129	C₁₆H₂₂O₄	278.34	$0.9 \pm 0$	O
55	Octadecanoic acid	34.3	C₁₈H₃₆O₂	284.48	$0.7 \pm 0$	F
56	Docosane	34.655	C₂₂H₄₆	310.60	$0.8 \pm 0.1$	H
57	Tetracosane	34.821	C₂₄H₅₀	338.65	$0.8 \pm 0$	H
58	Agathadiol	35.107	C₂₀H₃₄O₂	306.50	$0.9 \pm 0.1$	D
59	Erucic acid	35.204	C₂₂H₄₂O₂	338.6	$0.6 \pm 0$	F
60	Hexacosane	35.605	C₂₆H₅₄	366.71	$1.0 \pm 0.1$	H
61	Octacosane	36.154	C₂₈H₅₈	394.76	$1.0 \pm 0.1$	H
	Total				97.1
	Hydrocarbons				5.5
		Aliphatic			5.5
		Aromatic			-
	Monoterpenes				5.4
		Hydrocarbon			-
		Oxygenated			5.4
	Sesquiterpenes				65.7
		Hydrocarbon			34.0
		Oxygenated			31.7
	Diterpenes				1.6
	Fatty acids & Esters				8.8
	Other oxygenated compounds				10.1

Table 3.

Chemical Composition of the Essential Oil Extracted from the Leaves of P. longifolia.

No	Name	RT(min)	M.F.	M.W.	Area%	Class
1	β-Linalool	5.828	C₁₀H₁₈O	154.25	$1.0 \pm 0.1$	M
2	3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one	7.561	C₆H₈O₄	144.12	$5.2 \pm 0.4$	O
3	γ-Terpineol	9.661	C₁₀H₁₈O	154.25	$0.5 \pm 0$	M
4	5-Hydroxymethylfurfural	9.982	C₆H₆O₃	126.11	$1.1 \pm 0.1$	O
5	Geraniol	10.165	C₁₀H₁₈O	154.25	$0.4 \pm 0$	M
6	α-Cubebene	10.766	C₁₅H₂₄	204.35	$0.8 \pm 0$	S
7	. α-ylangene	11.246	C₁₅H₂₄	204.35	$0.8 \pm 0$	S
8	α-Copaene	11.349	C₁₅H₂₄	204.35	$1.3 \pm 0.1$	S
9	β-Cubebene	11.613	C₁₅H₂₄	204.35	$1.5 \pm 0.1$	S
10	β-Elemene	11.801	C₁₅H₂₄	204.35	$0.7 \pm 0$	S
11	α-Bourbonene	12.168	C₁₅H₂₄	204.35	$0.9 \pm 0.1$	S
12	β-Caryophyllene	12.305	C₁₅H₂₄	204.35	$9.5 \pm 0.5$	S
13	α-Humulene	12.997	C₁₅H₂₄	204.35	$5.3 \pm 0.4$	S
14	γ-Muurolene	13.444	C₁₅H₂₄	204.35	$0.5 \pm 0$	S
15	α-Amorphene	13.575	C₁₅H₂₄	204.35	$8.8 \pm 0.3$	S
16	γ-Cadinene	14.210	C₁₅H₂₄	204.35	$0.4 \pm 0$	S
17	Cadala-1(10),3,8-triene	14.290	C₁₅H₂₂	202.33	$0.3 \pm 0$	S
18	δ-Cadinene	14.359	C₁₅H₂₄	204.35	$2.4 \pm 0.2$	S
19	(E)-Nerolidol	14.834	C₁₅H₂₆O	222.37	$0.3 \pm 0$	S
20	Caryophyllene oxide	15.658	C₁₅H₂₄O	220.35	$6.7 \pm 0.4$	S
21	Globulol	15.887	C₁₅H₂₆O	222.37	$4.1 \pm 0.3$	S
22	Widdrol	16.179	C₁₅H₂₆O	222.37	$0.9 \pm 0$	S
23	τ-cadinol	16.825	C₁₅H₂₆O	222.37	$1.7 \pm 0.1$	S
24	Caryophylladienol II	17.088	C₁₅H₂₄O	220.35	$2.5 \pm 0.2$	S
25	Allo-Aromadendrene epoxide	17.163	C₁₅H₂₄O	220.35	$0.9 \pm 0$	S
26	α-Muurolol	17.455	C₁₅H₂₆O	222.37	$1.4 \pm 0.1$	S
27	α-Cadinol	17.706	C₁₅H₂₆O	222.37	$0.7 \pm 0$	S
28	Aromadendrene oxide-(1)	19.280	C₁₅H₂₄O	220.35	$4.5 \pm 0.3$	S
29	3-Hydroxy-5,6-epoxy-β-ionone	20.190	C₁₃H₂₂O₃	226.31	$4.2 \pm 0.2$	S
30	7,9-Dimethyl hexadecane	20.716	C₁₈H₃₈	254.5	$1.0 \pm 0$	H
31	Eudesm-11-en-1-ol	20.882	C₁₅H₂₆O	222.37	$0.4 \pm 0$	S
32	(E)-Nerolidyl acetate	22.599	C₁₇H₂₈O₂	264.40	$11.4 \pm 0.6$	S
33	Aristolene epoxide	24.533	C₁₅H₂₄O	220.35	$0.4 \pm 0$	S
34	Tetradecanoic acid	25.322	C₁₄H₂₈O₂	228.37	$2.1 \pm 0.2$	F
35	Hexahydrofarnesyl acetone	25.574	C₁₈H₃₆O	268.48	$3.8 \pm 0.3$	S
36	Hexadecanoic acid, methyl ester	27.777	C₁₇H₃₄O₂	270.45	$0.5 \pm 0$	F
37	Phytol	28.613	C₂₀H₄₀O	296.5	$1.6 \pm 0.1$	D
38	Hexadecanoic acid	28.761	C₁₆H₃₂O₂	256.42	$0.9 \pm 0.1$	F
39	Eicosane	30.146	C₂₀H₄₂	282.5	$0.3 \pm 0$	H
40	Disparlure	30.352	C₁₉H₃₈O	282.5	$0.8 \pm 0.1$	O
41	Henicosane	32.286	C₂₁H₄₄	296.6	$0.5 \pm 0$	H
42	Mono(2-ethylhexyl) phthalate	34.123	C₁₆H₂₂O₄	278.34	$0.5 \pm 0$	O
43	Octadecanoic acid	34.558	C₁₈H₃₆O₂	284.48	$0.8 \pm 0$	F
44	Docosane	34.649	C₂₂H₄₆	310.60	$0.9 \pm 0.1$	H
45	Tetracosane	34.815	C₂₄H₅₀	338.65	$0.4 \pm 0$	H
46	Agathadiol	35.101	C₂₀H₃₄O₂	306.50	$0.3 \pm 0$	D
47	Batilol	35.937	C₂₁H₄₄O₃	344.57	$0.7 \pm 0.1$	O
48	Octacosane	36.148	C₂₈H₅₈	394.76	$1.3 \pm 0.1$	H
	Total				97.9
	Hydrocarbons				4.4
		Aliphatic			4.4
		Aromatic			-
	Monoterpenes				1.9
		Hydrocarbon			-
		Oxygenated			1.9
	Sesquiterpenes				77.1
		Hydrocarbon			33.2
		Oxygenated			43.9
	Diterpenes				1.9
	Fatty acids & Esters				4.3
	Other oxygenated compounds				8.3

The major compounds in the flower's essential oil were: widdrol (29.8%), β-caryophyllene (9.7%), and E-nerolidyl acetate (5.8%). The mass spectra of the major compounds are shown in Fig. S2. Where the major compounds in the calyx's essential oil were: (E)-nerolidyl acetate (8.6%), α-humulene (8.1%), and β-caryophyllene (7.7%). The mass spectra of the major compounds are shown in Fig. S3. Whereas the major compounds in the leave's essential oil were: (E)-nerolidyl acetate (11.4%), β-caryophyllene (9.5%), α-amorphene (8.8%), caryophyllene oxide (6.7%), α-humulene (5.3%), and 3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (5.2%). The mass spectra of the major compounds are shown in Fig. S4.

In general, isoprenoids constitute the majority of the chemical composition of essential oils. This was shown by the chemical composition of the essential oils extracted from P. longifolia's aerial parts in this work. Where the chemical composition was dominated by sesquiterpene compounds (77.3% for flowers, 65.7% for calyxes, and 77.1% for leaves). In the flower's essential oil, the highest content was the share of oxygen sesquiterpenes (51.9%), represented by the major compounds: widdrol (29.8%), (E)-nerolidyl acetate (5.8%), caryophyllene oxide (2.7%), and corymbolone (2.6%). While the hydrocarbon sesquiterpene compounds were found in (25.4%), they were represented by the following major compounds: β-caryophyllene (9.7%), and α-humulene (4.0%). While in the calyx's essential oil, hydrocarbon and oxygen compounds were found in close proportions (34.0% and 31.7%, respectively). The oxygen sesquiterpene compounds were represented by the following major compounds: (E)-nerolidyl acetate (8.6%), hexahydrofarnesyl acetone (4.3%), carotol (3.8%), epiglobulol (3.5%), and aromadendrene oxide-(1) (3.0%), whereas hydrocarbon sesquiterpenes were represented by the following major compounds: α-humulene (8.1%), β-caryophyllene (7.7%), τ-elemene (4.6%), δ-selinene (3.9%), and δ-cadinene (3.1%). As for the leaves's essential oil, the highest value of oxygenic sesquiterpenes was (43.9%) and was represented by the following major compounds: (E)-nerolidyl acetate (11.4%), caryophyllene oxide (6.7%), aromadendrene oxide-(1) (4.5%), 3-hydroxy-5,6-epoxy-β-ionone (4.2%), globulol (4.1%), hexahydrofarnesyl acetone (3.8%), and caryophylladienol II (2.5%), while the hydrocarbon sesquiterpenes (33.2%) were represented by the following major compounds: β-caryophyllene (9.5%), α-amorphene (8.8%), α-humulene (5.3%), and δ-cadinene (2.4%). The monoterpenoid and diterpenoid were found in small amounts, and the compounds with the greatest value from these classes were: β-linalool (1.7% in flowers, 0.9% in calyxes, and 1.0% in leaves) for the monoterpenoid, and phytol (0.4% in flowers, 0.7% in calyxes, and 1.6% in leaves) for the diterpenoid. Furthermore, fatty acids & esters, and non-terpene hydrocarbon compounds were also present in small amounts. Octacosane had the highest value for these compounds in the hydrocarbon class (0.3% for flowers, 1.0% for calyxes, and 1.3% for leaves); as for the class of fatty acids and their esters, tetradecanoic acid had the highest value (1.7% for flowers, 3.9% for calyxes, and 2.1% for leaves).

Additionally, the amount of non-terpene oxygen compounds in essential oils was low, and the major compounds in this class are: 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (2.0% for flowers, 1.1% for calyxes, 5.2% for leaves), and 5-hydroxymethylfurfural (3.5% for flowers, 4.3% for calyxes, 1.1% for leaves).

Comparing the chemical composition of the oils demonstrates how similar the chemical content is among the essential oils extracted from the aerial parts of the P. longifolia plant. The majority of the compounds were the same but differed in concentration. For example, the main compound widdrol was found with a high value of (29.8%) in the flowers, while it was found with low values in the leaves and calyxes (0.9% and 1.3%, respectively). The compound α-amorphene was found as a major compound in the leaves (8.8%), while its value decreased in the flowers (1.9%), while it was not observed in the calyxes.

Several investigations have been conducted on the chemical composition of essential oils from different species of Phlomis spp. The studies have included the following species growing in Turkey (P. linearis, P. russeliana, P. grandiflora var. grandiflora, P. lunariifolia, P. amanica, P. monocephala, P. sieheana, P. armeniaca Willd, P. bourgaei, P. leucophracta, and P. chimerae),^22–27 Iran (P. lanceolata, P. anisodonta, P. bruguieri, P. olivieri),^28–30 Greece (P. fruticose, P. cretica, P. samia),³¹ Cyprus (P. brevibracteata, P. cypria),³² Tunisia (P. crinite),³³ Algeria (P. bovei).³⁴ Although the yield of essential oils varies greatly (0.05-1%), as observed in these investigations, sesquiterpenes dominate in their chemical composition. As Table 4 indicates, both compounds, β-caryophyllene and germacrene D, were found to be major compounds in large amounts in the majority of the Phlomis species plants that were investigated. Among the sesquiterpenes found as major compounds were farnesene in the oils of P. linearis (6.6%),²² P. lunariifolia (6.5%), P. amanica (8.3%), and P. sieheana (23.4%),²⁴ P. armeniaca Willd (7.24%),²⁵ P. bourgaei (15.88%),²⁶ P. lanceolata (10.5%),²⁸ and P. samia (20.7%),³¹ caryophyllene oxide in the oils of P. linearis (9.2%),²² P. russeliana (8.1%),²³ P. armeniaca Willd (13.35%),²⁵ P. chimerae (4.8%),²⁷ P. samia (3.2%),³¹ and P. brevibracteata (26.0-7.2%),³² and bicyclogermacrene in the oils of P. grandiflora var. grandiflora (4.9%), P. amanica (10.7%),²⁴ P. lanceolata (5.9%), P. bruguieri (4.1%),²⁸ and P. olivieri (10.2%).³⁰ In addition to sesquiterpenes, monoterpenes were found as major compounds in some of the Phlomis species oils. Among these compounds are α-pinene in the oils of P. leucophracta (19.2%) and P. chimerae (11.0%),²⁷ P. lanceolata (8.7%),²⁸ P. bruguieri (6.8%),²⁹ P. olivieri (11.7%),³⁰ P. fruticose (12.6%), and P. cretica (9.4%).³¹ limonene in the oils of P. grandiflora var. grandiflora (2.7%), P. leucophracta (11.0%), P. chimerae (5.5%),²⁷ and P. cretica (7.1%).³¹ Despite the fact that sesquiterpene compounds constitute the majority of the essential oil composition in most Phlomis species, it is evident that these species differ chemically from one another. The main compounds in the oil of P. grandiflora var. grandiflora collected from the northern and southern regions of Turkey were found to be $β$ -eudesmol (42.0%) and $α$ -eudesmol (16.1%).²³ knowing that the oil of the same plant collected from an Antalya mountainous area in Turkey had the main compounds: germacrene D (45.4%), $β$ -caryophyllene (22.8%), and bicyclogermacrene (4.9%).²⁷ Also in the oil of P. fruticose from Greece, the main compounds were Germacrene D (21.4%), α-pinene (12.6%), β-caryophyllene (12.6%), linalool (8.0%), and (Z)-γ-bisabolene (7.1%), while the oil of P. fruticosa from Montenegro, Yugoslavia, was different, and its main compounds were α-pinene (38.9-56.6%), β-caryophyllene (2.0-8.7%), 1,8-cineol (8.0-10.4%), limonene (2.1-2.2%), and α-thujone (2.0-1.4%).³¹ Noteworthy is the minor resemblance between the chemical composition of the essential oils of P. longifolia in our investigation and the chemical composition of various Phlomis species oils with varying concentrations. Regarding the major components, it was found that the compounds widdrol and (E)-nerolidyl acetate were found in Phlomis species essential oils for the first time, and that α-amorphene was identified only in one study at a very low concentration of 0.7%.²⁹ while the remaining major components have been found in various Phlomis species at varying concentrations.

Table 4.

Phlomis Spp. Containing β-Caryophyllene and Germacrene D.

No	Species	β-caryophyllene (%)	germacrene D (%)	References
1	P. linearis	24.2	22.3	²²
2	P. russeliana	22.6	15.1	²³
3	P. lunariifolia	9.0	7.7	²⁴
4	P. amanica	0.9	14.7
5	P. monocephala	5.1	6
6	P. sieheana	1.1	16.6
7	P. armeniaca Willd	18.08	35.68	²⁵
8	P. bourgaei	37.37	10.97	²⁶
9	P. leucophracta	20.2	4.5	²⁷
10	P. chimerae	31.6	6.1
11	P. grandiflora var. grandiflora	22.8	45.4
12	P. lanceolata	2.7	47.0	²⁸
13	P. anisodonta	11.0	65.0
14	P. bruguieri	1.2	60.5
15	P. olivieri	16.1	28.1	³⁰
16	P. fruticose	12.6	21.4	³¹
17	P. cretica	17.3	20.1
18	P. samia	5.8	6.3
19	P. crinite	40.8	39.1	³³
20	P. bovei	7.05	21.45	³⁴
21	P. brevibracteata	21.9	24.2	³²
22	P. cypria (L)	37.4	47.7	³²

The chemical composition of essential oils is influenced by a variety of factors, both internal and external. One of these important internal factors is the variation in the plant parts because different plant parts have various secretory structures that distribute irregularly throughout the plant body.³⁵ This could explain the quantitative and qualitative diversity in chemical composition between flowers, calyxes, and leaves. The physiological stage of the plant during which the plant samples were taken (the flowering period), when the plant is susceptible to attack by pollinators and diseases, is one of the external factors that influences the chemical composition of essential oils. Furthermore, the genotype of the plant has the greatest influence on the production of secondary metabolites, as plants subjected to harsh environmental stresses and ongoing external conditions can change their genotype and allow for alternative biosynthesis pathways, which results in a diversity of secondary metabolite production that is both qualitatively and quantitatively varied.³⁶ This could account for the variations in the chemical composition of essential oils extracted from various Phlomis plant species.

Evaluation of the Biological Efficacy of the Identified Compounds by GC-MS

Table 5 shows the biological activity of the identified compounds in the essential oils from the aerial parts of P. longifolia. Among the (63, 61, and 48) identified compounds, (50, 45, and 41) compounds with different biological activities were found, according to the published literature. Which represent (79.4%, 73.8%, and 85.4%) of the total compounds for flowers, calyxes, and leaves, respectively. (43, 37, and 34) antimicrobial active compounds were found, representing (86.0%, 82.2%, and 82.9%) of all active compounds. Furthermore, (30, 26, and 24) compounds with antioxidant activity were found, representing (60.0%, 57.8%, and 58.5%) of the total active compounds. Also, it was found that (27, 26, and 20) compounds have anti-cancer activity, representing (54.0%, 57.8%, and 48.8%) of all active compounds. Moreover, it was also found (17, 18, and 15) compounds that have anti-inflammatory activity, which represent (34.0%, 40.0%, and 36.9%) of the total active compounds for each of the flowers, calyxes, and leaves, respectively. In addition to the presence of several compounds with activities related to the nervous system and the cardiac system, several compounds have also been found to be effective as insecticides and herbicides.

Table 5.

Literature Biological Activity of the Identified Active Compounds in Essential Oils Extracted from the Aerial Parts of P. longifolia.

No	Compound Name	Activity
1	β-Linalool ^a,b,c	Antibacterial³⁷; anti-inflammatory³⁸; sedative activities³⁹.
2	3,5-Dihydroxy-6-methyl-2,3-dihydro-4H- pyran-4-one ^a,b,c	Anticancer⁴⁰; antioxidant⁴¹; antimicrobial, anti-inflammatory⁴²; antidiabetic activities⁴³.
3	p-Cymen-8-ol ^a	Antibacterial⁴⁴; antioxidant, antianxiety, hypocholesterolemic⁴⁵; insecticide activities⁴⁶.
4	α-Terpineol ^a	Antimicrobial, anti-inflammatory, antioxidant, anticancer, anticonvulsant, antiulcer, antihypertensive, analgesic, insecticide activities, flavors and fragrances industry^47,48.
5	γ-Terpineol ^a,b,c	Antimicrobial, anticancer activities⁴⁹.
6	5-Hydroxymethylfurfural ^a,b,c	Antimicrobial, antioxidant, anti-ischemic, anticancer, hepatoprotective, antiallergic, sickle-cell anemia activities^42,50.
7	Geraniol ^a,c	Antimicrobial, antioxidant, anticancer, anti-inflammatory, antiallergic, anthelmintic, insecticide and insectifuge activities, flavour and fragrance industry⁵¹.
8	Carvacrol ^a	Antimicrobial, antioxidant, anticancer, anti-inflammatory, antimutagenic, analgesic, antispasmodic, antihypertensive, hepatoprotective, insecticide activities^52,53.
9	Thymol ^b	Antimicrobial, antioxidant, antiviral, anticancer, anti-inflammatory, antispasmodic, antihypertensive, insecticide and insectifuge activities^53–55.
10	α-Cubebene ^a,b,c	Antimicrobial⁵⁶ antioxidant, anti-inflammatory activities⁵⁷.
11	α-Longipinene ^a	Antiviral activity⁵⁸.
12	Linalyl isobutyrate ^b	Anticancer activity⁵⁹.
13	α-Copaene ^a,c	Antioxidant activity⁶⁰.
14	Isoledene ^b	Anticancer activity^61,62.
15	β-Cubebene ^c	Neuroprotective activity⁶³.
16	β-Bourbonene ^a	Antibacterial, anticancer activities^64,65.
17	β-Maaliene ^b	Antimicrobial, antioxidant activities^66,67.
18	α-Funebrene ^a	Antimicrobial, antioxidant activities⁶⁸.
19	β-Elemene ^c	Anticancer, anti-inflammatory activities⁶⁹.
20	α-Cedrene ^a	Antimicrobial, anticancer, anti-obesity activities^70-72.
21	β-Caryophyllene ^a,b,c	Antioxidant, anticancer, anti-inflammatory, antidepressant, antianxiety, anticonvulsant, analgesic, muscle relaxant, nervous system diseases, osteoporosis activities⁷³.
22	Trans-α-Bergamotene ^b	Anti-inflammatory, anticancer⁷⁴; antioxidant, antibacterial, antifungal activities, flavoring agent⁷⁵.
23	α-Humulene ^a,b,c	Anticancer⁷⁶; anti-inflammatory^77,78; antioxidant⁷⁹; antibacterial, insecticide activities^80,81.
24	γ-Muurolene ^c	Antimicrobial activity⁸².
25	α-Curcumene ^b	Anti-inflammatory, anticancer, hypotriglyceridemic^83,84; antiviral activities⁸⁵.
26	α-Amorphene ^a,c	Antimicrobial, antioxidant, anti-inflammatory activities⁸⁶.
27	δ-selinene ^b	Antibacterial activity⁶⁶.
28	α-Muurolene ^a	Antifungal activity⁸⁷.
29	β-Bisabolene ^a	Antimicrobial⁸⁸; anticancer activities⁸⁹.
30	Cadala-1(10),3,8-triene ^c	Antibacterial activity⁹⁰.
31	δ-Cadinene ^a,b,c	Antimicrobial⁹¹; antioxidant activities⁹².
32	(E)-Nerolidol ^c	Antioxidant, antimicrobial, anticancer, anti-inflammatory, analgesic, antiulcer, insecticide and insectifuge activities, cosmetics and non-cosmetic products⁹³.
33	Caryophyllene oxide ^a,b,c	Anticancer^94,95; anti-inflammatory, sedative, analgesic^96,97; anti-parasite⁹⁸; antifungal, insecticide activities⁹⁹.
34	Epiglobulol ^b	Antibacterial, antiviral, antiseptic activities¹⁰⁰.
35	Globulol ^c	Antioxidant, antimutagenic, antifungal, antibacterial, anticonvulsant activities¹⁰¹.
36	Carotol ^b	Antifungal, herbicide, insecticide activities¹⁰².
37	Widdrol ^a,b,c	Anticancer¹⁰³; anti-obesity, anti-adipogenic¹⁰⁴; antioxidant, antifungal, herbicide activities¹⁰⁵.
38	Geranyl isovalerate ^a,b	Anticancer activity¹⁰⁶.
39	τ-cadinol ^a,b,c	Antibacterial, anticancer¹⁰⁷; anti-parasite activities¹⁰⁸.
40	Caryophylladienol II ^a,b,c	Antimicrobial activity¹⁰⁹.
41	Allo-Aromadendrene epoxide ^c	Antioxidant, anti-inflammatory, herbicide activities¹¹⁰.
42	α-Muurolol ^c	Antibacterial, antioxidant activities¹¹¹.
43	Cubenol ^a	Antimicrobial, antioxidant, anticancer¹¹², insecticide activities¹¹³.
44	α-Cadinol ^a,c	Antioxidant, antibacterial, antifungal activities¹¹⁴.
45	Patchoulol ^b	Antimicrobial, anticancer, antioxidant, anti-inflammatory, analgesic activities¹¹⁵.
46	2-Methyl hexadecane ^a	Antimicrobial, antioxidant activities¹¹⁶.
47	Aromadendrene oxide-(1) ^a,b,c	Anticancer¹¹⁷; antifungal¹¹⁸; antibacterial, anti-inflammatory¹¹⁹; antioxidant activities¹²⁰.
48	3-Hydroxy-5,6-epoxy-β-ionone ^a,c	Anticancer¹²¹; herbicide activities¹²².
49	Eudesm-11-en-1-ol ^a,c	Anticancer, antibacterial activities¹²³.
50	(E,Z)-Farnesol ^a,b	Antimicrobial activity¹²⁴.
51	Zerumbone ^a,b	Anticancer, anti-inflammatory, antioxidant^125,126; antimicrobial¹²⁷; analgesic¹²⁸; anti-alzheimer's activities¹²⁹.
52	Aristolene epoxide ^a,b,c	Antioxidant, herbicidal activities¹³⁰.
53	Tetradecanoic acid ^a,b,c	Antibacterial, antifungal¹³¹; antioxidant, anticancer, hypocholesterolemic activities¹³².
54	Hexahydrofarnesyl acetone ^a,b,c	Antimicrobial, antioxidant, insecticide activities^133,134.
55	Corymbolone ^a,b	Antimicrobial, antioxidant activities¹³⁵.
56	Hexadecanoic acid, methyl ester ^a,c	Antioxidant, antiviral, anticancer¹³⁶; antifungal¹³⁷; hypocholesterolemic, insecticide, nematicide, lubricant activities¹³².
57	Phytol ^a,b,c	Antioxidant, antimicrobial, anticancer, anti-inflammatory, anticonvulsant, anti-diabetic, antimutagenic, antianxiety, antiatherosclerosis, antihyperlipidemic, anti-scratching, immune adjuvant, antidepressant, anti-obesity, analgesic, anthelmintic, diuretic activities, hair growth facilitator, cosmetic and non-cosmetic products^138-140.
58	Hexadecanoic acid ^a,b,c	Antimicrobial, anti-inflammatory¹⁴¹; antioxidant, anticancer^142,143; hypocholesterolemic, nematicide, insecticide, antialopecic, flavor, lubricant activities^144,145.
59	Dibutyl phthalate ^a	Antimicrobial activity, plasticizer¹³².
60	Eicosane ^c	Antimicrobial, larvicidal activities¹³².
61	(Z)-Falcarinol ^b	Antioxidant¹⁴⁶; antibacterial, antifungal, anti-inflammatory, anticancer, herbicide activities¹⁴⁷.
62	10,13-Octadecadienoic acid, methyl ester ^a	Antioxidant, antimicrobial, anticancer¹⁴⁸; anti-inflammatory, hepatoprotective, hypocholesterolemic, antieczemic, antiarthritic, insectifuge activities¹⁰.
63	Henicosane ^a,b,c	Antimicrobial activity¹⁴⁹.
64	(Z,Z,Z)-9,12,15-Octadecatrienoic acid, methyl ester ^a	Anticancer, antibacterial, antioxidant, anti-inflammatory, anticonvulsant, antipyretic, antiseptic, analgesic, antieczemic, antiacne, antiarthritic, cardioprotective, hepatoprotective, hypocholesterolemic, insectifuge activities^150-152.
65	cis-6-Octadecenoic acid ^b	Anticancer, antimicrobial, antiaging¹⁵³; insectifuge activities¹⁵⁴.
66	8,11-Octadecadienoic acid, methyl ester ^b	Antioxidant¹⁵⁵; antidiabetic, anti-obesity activities¹⁵⁶.
67	(Z,Z)-9,12-Octadecadienoic acid ^b	Antioxidant, antimicrobial, anticancer^157,158; anti-inflammatory, hypercholesterolemic, hepatoprotective, antieczemic, antiacne, antiarthritic, insectifuge activities¹⁵⁹.
68	13-Methyl-oxacyclotetradecane-2,11-dione ^b	Antioxidant activity¹⁶⁰.
69	Octadecanoic acid ^a,b,c	Anticancer, antibacterial, antifungal activities¹³².
70	Docosane ^a,b,c	Antimicrobial, antioxidant activities¹⁶¹.
71	Tetracosane ^b,c	Antioxidant, antibacterial, anticancer, anti-inflammatory, antiulcer, antidiarrheal, antitrichomonas, anticorrosive, cardiotonic, laxative, anthelmintic activities¹⁶².
72	Agathadiol ^a,b,c	Antifungal activity¹⁶³.
73	Erucic acid ^b	Antimicrobial, anticancer, antiatherosclerosis, treating various skin diseases, cardioprotective activities¹⁶⁴.
74	Hexacosane ^a,b	Antimicrobial activity¹⁶⁵.
75	Batilol ^a,c	cosmetics as skin conditioning agent¹⁶⁶.
76	Octacosane ^a,b,c	Antioxidant, antimicrobial, anti-inflammatory activities⁶³.

Compounds identified in flower's essential oil, ^bcompounds identified in the calyx's essential oil, ^ccompounds identified in the leave's essential oil.

Essential oils are a significant and abundant source of biologically active compounds that can be used in various pharmaceutical science fields. The primary biological function attributed to essential oils is antioxidant activity. The second biological function is antimicrobial, followed by insecticide and repellent activity. While the least active are anti-cancer, anticonvulsant, anti-inflammatory, etc.¹⁶⁷ However, in this work, the results of the research in the published literature on the biological activity of the essential oil components of the aerial parts of P. longifolia shown in Table 5 were interesting. Besides the richness of these essential oils in compounds that have antioxidant and antimicrobial activities, compounds that have anti-cancer and anti-inflammatory activities were found in an appreciable percentage. While a few compounds were found to have insecticide and insectifuge efficacy as well as activity related to the nervous system, heart, and skin. Therefore, it is possible to forecast the potential of essential oils extracted from the aerial parts of P. longifolia as a potential preventive or therapeutic agent for various diseases brought on by microbes or induced by oxidative stress. Furthermore, it may be used as a natural preservative instead of synthetic preservatives.

To our knowledge, there have been no previous chemical or biological studies on essential oils extracted from the aerial parts of P. longifolia. Consequently, we were unable to compare the chemical composition of our study's results with those of previous investigations. particularly considering that, given the capabilities at hand, we only used one method to verify the chemical composition (by comparing mass spectra for compounds with those in the device library). Therefore, this study is considered an initial investigation that may be used to support future chemical research on this plant and from various locations to verify its chemical composition and investigate its biological activities with the aim of developing new drugs as well as employing it in possible pharmaceutical and food applications.

Conclusions

In this work, the chemical composition of essential oils extracted from the aerial parts of P. longifolia was determined for the first time by GC-MS. Essential oils were rich in phytochemical compounds, especially sesquiterpenes, which were characterized by a diversity of biological activities. Therefore, such compounds provide leads for future research on biological activities of commonly used medicinal plants for their nutritional and therapeutic purposes.

Materials and Methods

Instrumentation and Chemicals

GC-MS (Agilent −6890, USA), clevenger-type apparatus (Shamlab, Syria), laboratory heating (Heraeus Wittmann, Germany), sensitive scale (Sartorius, Germany), rotary evaporator (Heidolph Laborota 4000, Germany), laboratory glassware (Isolab, Germany), hexane (Honeywell, Germany), sodium sulphate (ANH.) (TITAN BIOTECH LD, India), filter paper (Whatman no.1, USA).

Plant Material

The aerial parts (flowers, calyxes, and leaves) of the P. longifolia Boiss. & C.I. Blanche. wild plant were collected during the flowering period in June 2022 from a mountainous area located at an altitude of about 900 m (Latakia Province-Syria). A voucher specimen (No. HFC 950) has been deposited in the herbarium of the faculty of science (Tishreen University, Latakia, Syria). Plant specimens were identified by Prof. Dina Haddad from that faculty. After washing and drying in the shade, they were ground well and stored in an opaque glass bowl until extraction time.

Essential oil Extraction

The essential oils were extracted by hydrodistillation of dried and ground plant material (flowers, calyxes, and leaves) for 5 h (100 g of each sample in 500 ml of distilled water) using a Clevenger-type apparatus.¹⁶⁸ The fractions of oils were collected in hexane and dried using anhydrous sodium sulfate. After filtration, the solvent was removed by passing a stream of nitrogen, and the oils were stored at +4 °C until analysis. The weight of the obtained oils was $0.14 \pm 0.03 g$ , $0.075 \pm 0.006 g$ , and $0.19 \pm 0.02 g$ for the flowers, calyxes, and leaves, respectively.

GC-MS Analysis

GC-MS analysis was carried out using an Agilent −6890 gas chromatograph coupled to a Hewlett Packard-5975 mass spectrometry. A HP-5 column (30 m × 0.25 mm, film thickness 0.25 μm), stationary phase: 5% phenyl methyl siloxane, was used. The column temperature was programmed at 70 °C, then increased to 280 °C at 4 °C/min, and held for 10 min. Helium was used as a carrier gas, at a flow rate of 1.2 ml/min. The injections were performed in splitless mode at 250 °C. Mass spectra were recorded with an ionization energy of 70 eV and an interface temperature of 230 °C.

Identification of Components

The compounds were identified based on the interpretation of the mass spectra of GC-MS using the databases of NIST and WILEY, where the mass spectra of the unknown components were compared with the spectra of the known components stored in the NIST 05a. L, NIST 02. L, and WILEY 7.1 libraries.

Statistical Analysis

All the experiments were performed in triplicate. For each result, the data were summarized as the mean ± standard deviation (SD). Statistical analysis was performed using Microsoft Excel (version 2013).

Supplemental Material

sj-docx-1-npx-10.1177_1934578X241282866 - Supplemental material for Essential Oils from Phlomis longifolia Boiss. & C.I. Blanche. Aerial Parts (Flowers, Calyxes, Leaves): GC-MS Analyzes and Biological Properties

Supplemental material, sj-docx-1-npx-10.1177_1934578X241282866 for Essential Oils from Phlomis longifolia Boiss. & C.I. Blanche. Aerial Parts (Flowers, Calyxes, Leaves): GC-MS Analyzes and Biological Properties by Muhannad Hasan, Imad Hwija and Yaseer Mossa in Natural Product Communications

Footnotes

Acknowledgments

We thank Dr. Fadi Younis (Friedrich-Schiller-University Jena) for review the manuscript.

Author Contributions

Conceptualization, M.H., I.H. and Y.M.; methodology, M.H. and I.H.; validation, M.H. and I.H.; formal analysis, M.H. and I.H.; investigation, M.H, I.H. and Y.M.; data curation, M.H..; writing—original draft preparation, M.H.; writing—review and editing, M.H., I.H. and Y.M.; supervision, I.H. and Y.M. All authors have read and agreed to the published version of the manuscript.

Declaration of Conflicting Interests

The authors declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Ethical Approval

Ethical Approval is not applicable for this article.

Funding

The authors received no financial support for the research, authorship, and/or publication of this article.

ORCID iD

Muhannad Hasan

Statement of Human and Animal Rights

This article does not contain any studies with human or animal subjects.

Statement of Informed Consent

There are no human subjects in this article and informed consent is not applicable.

Supplemental Material

Supplemental material for this article is available online.

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