Methyl Eugenol, 1,8-Cineole and Nerolidol Rich Essential Oils with their Biological Activities from three Melaleuca Species Growing in Tarai Region of North India

Joshi, Archana; Prakash, Om; Pant, Anil Kumar; Kumar, Ravendra; Szczepaniak, Lech; Kucharska-Ambrożej, Kamila

doi:10.1590/1678-4324-2021210186

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Article - Biological and Applied Sciences • Braz. arch. biol. technol. 64 • 2021 • https://doi.org/10.1590/1678-4324-2021210186 copy

Methyl Eugenol, 1,8-Cineole and Nerolidol Rich Essential Oils with their Biological Activities from three Melaleuca Species Growing in Tarai Region of North India

Authorship SCIMAGO INSTITUTIONS RANKINGS

HIGHLIGHTS

E-nerolidol, 1,8-cineol and methyl eugenol rich species of Melaleuca were identified in this study.

Essential oils exhibited strong antioxidant,antibacterial and Invitro anti inflammatory activity.

These marker constitutents impart valuable place of this crop in agriculture.

Abstract

The essential oils from the fresh leaves of three Melalecua spp. viz; Melaleuca leucadendron (L.) Melaleuca linariifolia Sm. and Melaleuca bracteata F. Muell. growing in Tarai region of North India were analyzed by a combination of gas chromatography/mass spectrometry. The analysis revealed the presence of several constituents of industrial and pharmacological importance. M. leucadendron essential oil was found to be dominated by E-nerolidol (85.7%) rich chemotype. 1,8-cineole (61.1%) along with significant presence of α-terpineol (12.3%), α-pinene (4.0%), β-myrcene (3.8%), and E-caryophyllene (1.7%) were identified in the essential oil from M. linariifolia Similarly M. bracteata was dominated by the presence of phenylpropanoids viz; methyl eugenol (74.8%) and methyl cinnamate (8.0%). The essential oils were studied for their in-vitro antioxidant, anti-inflammatory and antimicrobial potential. All the oils revealed potential antioxidant activity with maximum in M. bracteata essential oil. All the oils exhibited significant antibacterial activity against Bacillus megaterium, Staphylococcus aureus, Escherichia coli,Salmonella typhimurium and anti-fungal activity against phytopathogenic fungi Fusarium oxysporum, Sclerotinia sclerotiorum, Exserohilum turcicum and Curvularia lunata. The observations from present study suggest further cultivation of Melaleucas and its commercialization as industrial crops.

Keywords:
Methyl eugenol; 1,8-cineole; (E)-nerolidol; Melaleuca Antioxidant; Antifungal; antimicrobial

S.N.	Compounds	RI	% Composition
			Present Study			Padalia et.al [³⁶36 Padalia RC, Verma RS, Chauhan A, Goswami P, Verma SK, Darokar MP. Chemical composition of Melaleuca linarrifolia Sm. from India: a potential source of 1, 8-cineole. Ind Crops Prod. 2015a Jan; 63(1):264-268.,³⁷37 Goswami P, Verma SK, Chauhan A, Venkatesha KT, Verma RS, Singh VR, et al. Chemical composition and antibacterial activity of Melaleuca bracteata essential oil from India: A natural source of methyl eugenol. Nat. Prod. Commun. 2017 Jun;12(6): 965-968.,⁴⁹49 Dorman HD, Deans SG. Antimicrobial agents from plants: antibacterial activity of plant volatile oils. J. Appl. Microbiol. 2000 Feb;88(2):308-16.]
			M. leucadendron	M. linariifola	M. bracteata	M.leucadendron (2015)	M.linariifola (2015)	M.bracteata (2017)
1.	Methyl 2- methylbutanoate	780	0.1	0.1	t	-	-	-
2.	α-thujene	924	-	0.1	0.1	-	t	0.08
3.	α-pinene	932	0.4	4.0	0.1	t	1.99	-
4.	camphene	948	t	0.1	-	0.10	t	-
5.	benzaldehyde	960	1.2	-	t	-	-	-
6.	sabinene	969				0.64
7.	β-pinene	975	t	1.6	0.1	0.50	0.85	0.04
8.	6-methyl-5-hepten-2-one	985	0.1	-	-	-		-
9.	β-myrcene	990	t	3.8	0.3	0.10	1.78	0.12
10.	pseudolimonene	1002	-	0.2	-	-	-	-
11.	α-phellandrene	1002	-	-	1.0	-	-	0.16
12.	p-mentha -1(7),8-diene	1002					0.14
13.	α-terpinene	1014	-	0.3	0.1	-	-	-
14.	p-cymene	1021	-	-	0.7	-	0.21	0.36
15.	limonene	1025	0.4	-	0.3	-	0.15	0.30
16.	1,8-cineole	1030	0.1	61.1	0.2	0.30	77.40	0.34
17.	E-ocimene	1046	t	0.1	0.1		-	-
18.	γ-terpinene	1056	t	0.8	0.1	t	0.41	-
19.	α-terpinolene	1086	0.1	0.2	1.1	-	-	0.26
20.	Methyl benzoate	1093	t	0.1	t	-	-	-
21.	linalool	1099	0.7	0.2	1.2	0.52	0.19	0.94
22.	exo-fenchol	1120					0.10
23.	camphor	1141				0.38
24.	isopulegol	1142	0.4	-	t	-	-	-
25.	citronellal	1152	-	-	0.1	-	-	-
26.	δ-terpineol	1165	-	0.6	-	-	0.46	-
27.	Terpin-4-ol	1174	t	1.1	0.2	t	0.76	0.40
28.	p-cymen-8-ol	1183	-	-	0.1	-	-	-
29.	α-terpineol	1190	0.1	12.3	0.8	0.10	7.72	0.54
30.	Methyl chavicol	1197	-	-	0.4	-	-	0.32
31.	citronellol	1228	0.2	-	0.4	-	-	0.04
32.	neral	1239	-	-	0.1	0.22	-	-
33.	E-geraniol	1253	t	-	0.1	-	-	0.07
34.	linalyl acetate	1254				-
35.	Methyl citronellate	1260	-	-	0.1	-	-	-
36.	α-citral	1269	-	-	0.2	-	-	-
37.	geranial	1270						0.12
38.	bornyl acetate	1284				0.11
39.	S-methyl thiobenzoate	1290	0.1	-	-	-	-	-
40.	Z-methyl cinnamate	1304	-	-	0.1	-	-	-
41.	Methyl geranate	1323	-	-	0.1	-	-	-
42.	δ-elemene	1335				-
43.	α-terpinyl acetate	1346				0.53
44.	α-cubebene	1348	-	-	0.1	-	-	-
45.	Citronellyl acetate	1353	-	-	0.2	-	-	-
46.	eugenol	1356	0.1	0.3	0.5	-	t	0.04
47.	Neryl acetate	1364	-	0.1	-	-	t	-
48.	α-ylangene	1369					t
49.	isoledene	1371	-	0.1	-	-	-	-
50.	α-copaene	1374	-	-	0.1	-	t	-
51.	E-methyl cinnamate	1383	-	-	8.0	-	-	4.12
52.	Geranyl acetate	1383	-	0.1	-	-	t	-
53.	β-bourbonene	1387				-
54.	α-gurjunene	1408	-	0.1	-	-	-	-
55.	Methyl eugenol	1416	-	0.6	74.8	-	t	88.18
56.	E-β-caryophyllene	1417	0.9	1.7	-	1.52	2.88	-
57.	Z-β-copaene	1431	-	-	0.5	-	-	-
58.	α-guaiene	1432					0.46
59.	aromadendrene	1438	-	0.4	0.2	-	t	-
60.	Selina-5,11-diene	1441	-	0.1	-	-	-	-
61.	α-humulene	1452	0.2	0.3	0.2	0.22	0.31	-
62.	E-Muurola-3,5-diene	1453	-	-	0.1	-	-	-
63.	γ-gurjunene	1470	-	0.1	-	-	t	-
64.	Cabreuva oxide D	1475	0.1	-	-	-	-	-
65.	E-cadina-1(6),4-diene	1475	-	-	0.1	-	-	-
66.	D-germacrene	1480	-	-	1.1	-	-	0.60
67.	β-selinene	1484	-	0.1	-	-	-	-
68.	α-amorphene	1485					0.10
69.	δ-selinene	1489	-	0.1	-	-	-	-
70.	viridiflorene	1493	-	0.5	-	-	-	-
71.	bicyclogermacrene	1496	-	-	0.4	-	-	-
72.	E-methyl isoeugenol	1497						0.20
73.	α-muurolene	1499	-	0.1	0.1	-	0.18	-
74.	β-cadinene	1506	-	0.6	-	-	-	-
75.	E,E-α-farnesene	1508	0.1	-	-	-	-	-
76.	γ-cadinene	1513	-	0.1	0.1	0.10	0.12	-
77.	β-curcumene	1515					0.43
78.	E-calamenene	1522	-	0.2	-	-	0.10	-
79.	δ-cadinene	1522				-
80.	Z-calamenene	1524	-	-	0.7	-	-	-
81.	Z-nerolidol	1531				0.10
82.	Cadina-1,4-diene	1532	-	-	0.2	-	-	-
83.	α-calacorene	1542	-	1.1	t	-	-	-
84.	ledol	1557	-	0.2	-	-	-	-
85.	elemicin	1558	-	-	0.2	-	-	0.30
86.	germacrene-B	1558					0.99
87.	palustrol	1565	-	0.2	0.1	-	-	-
88.	E-nerolidol	1568	85.7	-	-	90.85	0.10	-
89.	spathulenol	1575	-	0.2	0.3	-	t	0.22
90.	Caryophyllene oxide	1581	3.7	-	-	0.99	0.10	0.14
91.	globulol	1582	-	1.2	0.3	0.70	-	-
92.	viridiflorol	1591	0.6	0.3	0.1	0.19	-	-
93.	Cubeban-11-ol	1592	-	0.5	0.1	-	0.52	-
94.	fokienol	1599	0.4	-	-	-	-	-
95.	juneperol	1599					t
96.	rosifoliol	1600	-	0.4	0.1	-	t	-
97.	Humulene epoxide II	1608	0.3	-	t	-		-
98.	1,10-di-epi-cubenol	1612	-	1.3	t	-	0.10	-
99.	10-epi-γ-eudesmol	1622				0.14
100.	epicubenol	1626	-	t	0.1	-	0.25	-
101.	Allo-aromadendrene epoxide	1632	0.1	-	-	-	-	-
102.	isospathulenol	1636	-	0.2	-	-	-	-
103.	Caryophylla-4(12),8(13)-diene-5-α-ol	1636	0.5	-	-	-	-	-
104.	τ-cadinol	1638	-	0.2	-	-	-	-
105.	epi-α-cadinol	1638				0.20	t
106.	τ-muurolol	1640	-	-	0.5	-	-	-
107.	α-muurolol	1643						0.20
108.	δ-cadinol	1644	-	0.1	0.1	-	-	-
109.	β-eudesmol	1649				t
110.	α-cadinol	1653	-	0.1	0.4	0.33	-	0.14
111.	E-14-hydroxy-9-epi caryophyllene	1670	0.1	-	t	-	-	-
112.	cadalane	1672	-	0.1	-		t	-
113.	β-bisabolol	1675				t
114.	(Z)-nerolidyl acetate	1679				t
115.	α-bisabolol	1685	0.2	-	-		-	-
116.	2Z,6Z-farnesol	1698	0.1	-	-		-	-
117.	2Z,6E-farnesol	1721	0.7	0.3	-		-	-
118.	Iso-longifolol	1732	0.1	-	-		-	-
119.	methylconiferylaldehyde	1777	-	-	0.3		-	-
120.	phytol	2112	-	0.3	-		-	-
121.	Total identified		97.8	99.0	98.1	98.84	98.90	98.24
122.	Monoterpene hydrocarbons		0.9	11.2	4.0	1.34	5.53	1.30
123.	Oxygenated monoterpenes		1.6	75.6	12.4	2.16	86.63	2.42
124.	Sesquiterpene hydrocarbons		1.2	5.7	3.9	1.84	5.67	0.60
125.	Oxygenated sesquiterpenes		92.2	5.3	2.1	93.50	1.07	0.70
126.	Others		1.9	0.6	75.7	-	-	93.14

Essential oil/Standard	Antioxidant activity(IC₅₀)
Essential oil/Standard	DPPH radical Scavenging	Metal chelating	Reducing power	NO Radical scavenging	SO Radical Scavenging
M.leucadendron	16.24±0.05	9.56±0.31	12.89±1.72	16.17±0.06	20.92±0.31
M.linerifolia	10.946±0.00	10.51±0.39	4.18±0.33	12.68±0.09	25.83±0.19
M.bracteata	4.06±0.02	8.80±0.44	2.11±0.39	11.60±0.09	21.79±0.85
Citric acid*	-	4.04±0.63	-	-	-
BHT*	9.29±0.09	-	2.46±0.25	-	-
Ascorbic Acid*	-	-	-	10.36±0.45	9.85±0.16

Essential oil	Conc. (ppm)	Mycelial growth inhibition (%)
		Fusarium oxysporum	Sclerotinia sclerotiorum	Curvularia lunata	Exserohilum turcicum
M.leucadendron	500	18.95±1.301^a	80.83±1.30^a	39.66±3.53^a	56.66±1.11^a
	250	12.91±0.72^b	77.70±0.95^ab	38.75±2.5^a	55.18±0.64^ab
	100	12.08±1.90^bc	75.83±3.20^b	35.41±2.00^ab	54.81±0.64^b
	50	11.33± 1.01^bc	75.16±0.314^b	32.91±3.14^b	52.59±1.28^c
	25	10±1.25^c	71.66±1.44^c	32.91±1.57^b	51.11±0.96^c
IC₅₀(ppm)		2332.65	1465.22	1136.35	318.57
M.linariifolia	500	28.95±2.00^a	58.58±0.88^a	38.16±0.57^a	59.07±1.15^a
	250	20.37±1.51^b	51.87±1.08^b	35.62±1.65^a	55.55±1.11^b
	100	9.79±1.57^c	50.87±3.68^b	31.25±1.25^b	54.62±3.61^bc
	50	9.16±1.57^c	25±1.25^c	27.91±3.14^b	54.44±2.22^bc
	25	7.70±0.368^c	7.08±1.44^d	23.54±3.55^c	52.40±2.50^c
IC₅₀(ppm)		938.50	318.81	883.13	253.02
M.bracteata	500	46.87±1.65^a	82.91±0.36^a	75.20±0.36^a	90±1.11^a
	250	36.12±1.59^b	76.04±0.95^b	60.20±0.954^b	88.51±0.64^a
	100	31.87±2.86^c	63.87±0.45^c	32.29±2.81^c	65.18±0.64^b
	50	17.29±1.57^d	47.08±2.00^d	31.08±1.44^c	58.14±1.69^c
	25	7.29±0.95^e	27.70±0.36^e	20.12±0.66^d	54.62±3.61^c
IC₅₀(ppm)	25	498.11	85.88	239.97	89.70
Carbendazim		100.00±0.00	100.00±0.00	100.00±0.00	100.00±0.00

S.N.	Sample	Zone of inhibition(mm)
		B.megaterium	S.typhimurium	E.coli	S.aureus
1.	M.leucadendron 10 15 20 25
		11.33 ± 0.58^c	12.67±0.58^d	16.33±1.15^b	10.33±1.52^c
		13.33 ±0.58^b	14.33±0.58^c	17±0.00^b	13.67±0.58^b
		14.33±0.58^b	16.33±0.58^b	18.33±0.58^a	15.67±0.58^a
		18.33±0.58^a	20.67±0.58^a	19.00±0.00^a	16.33±1.15^a
	MIC(µg/mL)	10	10	5	10
2.	M.linariifolia 10 15 20 25
		10.33±0.58^c	11.67±0.58^c	13.33±0.58^c	8.67±1.15^d
		12.67±0.58^b	15.33±0.58^b	14.67±0.58^b	10.33±0.58^c
		13.67±0.58^b	16.33±0.58^b	16±1.00^a	12.33±0.58^b
		19.67±0.58^a	20.67±1.15^a	17±0.00^a	14±0.00^a
	MIC(µg/mL)	10	10	5	10
3.	M.bracteata 10 15 20 25
		11±0.00^c	16.67±0.58^c	13.33±0.58^d	10.67±1.15^c
		11.67±0.58^c	17.67±0.58^c	15.67±0.58^c	12.67±1.15^b
		13.33±0.58^b	20.67±0.70^b	18.67±1.15^b	13.67±1.15^b
		14.67±0.58^a	23.67±0.58^a	20.67±0.58^a	15.67±0.58^a
	MIC(µg/mL)	10	5	5	10
4.	Refamycin 25 µg/mL
4.	Refamycin 25 µg/mL	31.33±1.22^a	35±1.00^a	32.67±1.15^a	27±1.00^a

Anti inflammatory activity	Essential oil/Standard
Anti inflammatory activity	M.leucadendron	M.linerifolia	M.bracteata	Diclofenec sodium
IC₅₀ Value	27.82±0.242	23.43±0.247	20.68±0.004	11.93±0.033

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