Chemical composition and antifungal potential of Vinca rosea leaf essential oil and extracts from Northern India

Figures & data

Table 1. Chemical composition of essential oil of Vinca rosea leaves.

Peaks	Compound name	Molecular formula	Retention time	Area%	m/z	RI (Lit.)	Adam RI (cal.)
1.	2,4-Dichlorophenol	C6H4Cl2O	17.857	2.64	163	1144	1282
2.	4-vinylguaiacol	C9H10O2	23.84	1.13	150	1313	1356
3.	2,6-Di-tert-butyl-4-hydroperoxy-4-methyl −2,5-cyclohexadien-1-one	C15H24O3	25.166	1.23	236	1478	1373
4.	Tetradecane	C14H30	27.321	0.92	198	1400	1400
5.	2,6-Di-tert-butyl-P-benzoquinone	C14H20O2	28.401	0.44	220	1443	1504
6.	2,6-Di-butyl-2,5-cyclohexadiene-1,4-dione	C14H20O2	29.769	6.43	220	1460	1523
7.	2,5-cyclohexadien-1-one, 2,6-bis(1,1-dimethylethyl)-4-hydroxy-4-methyl-	C15H24O2	29.924	9.97	236	1478	1525
8.	4-Phosphatricyclo[6.1.1.0(3,7)]dec-3(7)-ene,4,9,9-trimethyl	C12H19P	30.926	0.56	194	1442	1538
9.	Butylated hydroxytoluene	C15H24O	31.591	32.74	220	1503	1548
10.	1,2,4,5-Tetramethyl-6-methylenespiro [2.4]heptane	C12H20	32.267	0.8	164	1460	1557
11.	2-Methyl-2-(3-methyl-2-oxobutyl) cyclohexanone	C12H20O2	33.394	1.22	196	1470	1572
12.	2-Butyl-5-isobutylthiophene	C12H20S	34.37	0.26	196	1416	1586
13.	Pseudodiosphenol	C10H16O2	34.852	1.54	168	1267	1592
14.	Hexadecane	C16H34	35.376	2.47	226	1600	1600
15.	1,3-Pentadiene, 2,4-di-t-butyl-	C13H24	36.668	0.19	180	1097	1374
16.	Butan-2-one, 1-[3-(3,3-dimethyl-2-oxo-butylidene)piperazin-2-ylidene]-3,3-dimethyl-	C16H26N2O2	37.922	4.58	278	2277	1464
17.	2,6-di-tert-butyl-4-methylphenyl methylcarbamate	C17H27NO2	39.447	0.21	277	1846	1572
18.	2,6-Di-tert-butyl-4-methylene-2,5-cyclohexadienone	C15H22O	39.659	0.42	218	1483	1578
19.	Cyclopropanecarboxylic acid, 1-hydroxy-, (2,6-di-t-butyl-4-methylphenyl) ester	C19H28O3	40.106	0.36	304	2178	1619
20.	Leaf acetal	C10H20O2	41.178	0.81	172	1111	1695
21.	3-Methylheptadecane	C18H38	41.615	0.29	254	1746	1726
22.	2,4-Diphenyl-4-methyl-1-pentene	C18H20	41.808	0.48	236	1846	1739
23.	Octadecane	C18H38	42.654	1.79	254	1800	1800
24.	Nonadecane	C19H40	44.062	0.75	268	1900	1900
25.	1-Cyclohexenyl phenyl ketone	C13H14O	45.677	10.36	186	1687	1931
26.	Octacosane	C28H58	46.099	0.17	394	1461	1996
27.	Docosane	C22H46	47.648	1.34	310	2200	2200
28.	3-Indazolinone, 2-phenyl-	C13H10N2O	48.083	0.87	210	2087	2077
29.	Anthraquinone	C14H8O2	48.51	5.64	208	1956	2079
30.	Eicosane	C20H42	49.266	2.06	282	2000	2000
31.	Tricosane	C23H48	51.009	0.23	324	2300	2300
32.	3-Methyleicosane	C21H44	51.468	0.34	296	2074	2106
33.	Phytol	C20H40O	52.922	4.75	296	2100	2200
34.	Oxacyclononadec-10-en-2-one	C18H32O2	53.28	1.64	280	2158	2245
35.	Unidentified compounds	—	55.62	0.37	—	—	—
	Total area percentage			100

Compounds are categorized according to classification.

Hydrocarbons: Alkane (4,14,23,24,26,27,30,31); Alkene (10,22); Branched Alkene (21,32).

Aromatic hydrocarbon (1,2,3,5,6,7,8,9,11,12, 13, 15,17,18).

Oxygenated hydrocarbons: Alcohol (33); Ketone (20,34); Phenols (2,18); Quinones (3).

Thiophens (12); Phosphorus compounds (8); Carboxylic acid esters (19); Heterocyclic compounds (16); Acetal (20); Ketone (25,28,29,35).

RI (ref) = Kovats retention indices from literature (Adams, 2007).

RI (cal) = = Kovats retention indices from literature (Adams 21; NIST web book) (Adams 2007).

Figure 1. Major compounds in the essential oil of leaves.

Figure 2. Minor compounds in the essential oil of leaves.

Table 2. Percentage yield of extracts of leaves.

Extract	Yield (%)
Methanol	9.3
Hexane	4.4

Table 3. Phytochemical identification test for extracts of leaves.

Chemical constituents	Methanol	Hexane
Alkaloids	+	–
Amino acid	+	–
Carbohydrates	+	–
Flavonoids	+	+
Glycosides	+	–
Phenol	+	+
Saponin	+	+
Tannin	+	+
Terpenoid	+	+
Cardiac Glycosides	+	–

(+) = Presence and (-) = Absence.

Figure 3. Main compounds in methanolic extract of leaves.

Figure 4. Main compounds in hexane extract of leaves.

Table 4. The results of GC-MS of methanolic extract of leaves of Vinca rosea.

Peaks	Compound name	Molecular formula	Retention time	Area %	m/z
1	Glycerol	C3H8O3	16.006	17.58	92
2	4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-	C6H8O4	16.556	1.68	144
3	Sandalore	C14H26O	31.457	0.59	210
4	Dihydroactinidiolide	C11H16O2	32.574	0.43	180
5	1,2-Dimethyl-3,5-bis(1-methylethenyl) cyclohexane	C14H24	33.151	0.09	192
6	Megastigmatrienone A	C13H18O	36.278	0.17	190
7	Caryophyllene acetate	C17H28O2	38.869	0.28	264
8	Myristic acid	C14H28O2	41.843	0.13	228
9	17-Oxo-4-propyl-3,4-seco-4-androsten-3-oic acid methyl ester	C23H36O3	42.027	0.23	360
10	2,6,10-Trimethylundecan-(5E)-2,5,9-Trien-4-one	C14H22O	42.239	0.15	206
11	5-(2-Butenyl)-17-oxo-4-nor-3,5-seco-5.alpha.-androstan-3-oic acid, methyl ester	C23H36O3	42.542	0.14	346
12	3H-3,10a-Methano-1,2-benzodioxocin-3-ol, octahydro-7,7-dimethyl-, (3.alpha.,6a.beta.,10a.beta.)-	C13H22O3	43.537	0.31	226
13	alpha-Cedrene epoxide	C15H24O	43.763	0.08	220
14	Phytol	C20H40O	43.876	0.69	296
15	hexahydrofarnesyl acetone	C18H36O	44.082	0.15	268
16	Neophytadiene	C20H38	45.308	0.13	278
17	Inositol	C6H12O6	46.743	0.22	180
18	Methyl palmitate	C17H34O2	46.907	1.95	270
19	Butyl octyl phthalate	C20H30O4	47.804	0.31	334
20	Palmitic acid	C16H32O2	48.745	16.38	256
21	Methyl linoleate	C19H34O2	52.089	1.18	294
22	Methyl oleate	C19H36O2	52.319	3.88	296
23	Phytol	C20H40O	52.704	3.42	296
24	Methyl stearate	C19H38O2	53.181	0.4	298
25	(Z)-Tetradec-7-enal	C14H26O	54.093	19.61	210
26	Stearic acid	C18H36O2	54.707	1.44	284
27	4,8,12,16-Tetramethylheptadecan-4-olide	C21H40O2	59.582	0.27	324
28	7a-Methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one	C10H14O	60.03	0.45	150
29	2-cyclohexen-1-one, 3-methyl-5-(1-methylethyl)-4-(2-methyl-1-propenyl)-	C14H22O	60.649	0.68	206
30	Hexanoic acid 2-ethyl-hexadecyl ester	C24H48O2	61.94	0.84	368
31	2-Methylhexacosane	C27H56	62.409	0.17	380
32	Isoindolinine	C21H24N2O2	63.262	0.59	336
33	Isovindolinone	C21H24N2O2	63.524	0.79	336
34	Dotriacontane	C32H66	63.807	0.12	450
35	Hexanoic acid 2-ethyl-hexadecyl ester	C24H48O2	64.689	0.35	368
36	Coronaridine	C21H26N2O2	65.019	0.57	338
37	cis-Cyclo(Leucyl-Tyrosyl)	C15H20N2O3	65.55	0.16	276
38	cis-Cyclo(Leucyl-Tyrosyl)	C15H20N2O3	65.832	0.36	276
39	Squalene	C30H50	66.219	1.03	410
40	alpha-Tocospiro A	C29H50O4	66.56	0.3	462
41	alpha-Tocospiro-B	C29H50O4	66.804	0.41	462
42	Desmethoxyvindoline	C24H30N2O5	68.134	1.24	426
43	Stigmast-5-en-3-ol, oleate	C47H82O2	69.851	0.67	679
44	Vitamin E	C29H50O2	70.541	1.64	430
45	Vindoline-d3	C25H32N2O6	71.842	5.5	459
46	Campesterol	C28H48O	72.477	0.89	400
47	Stigmasterol	C29H48O	73.034	0.6	412
48	beta.-Sitosterol	C29H50O	74.443	1.91	414
49	5H-3,5a-Epoxynaphth[2,1-c]oxepin, dodecahydro-3,8,8,11a tetramethyl-	C18H30O2	75.356	0.49	278
50	24-Norursa-3,12-diene	C29H46	75.667	1.03	394
51	24-Norursa-3,12-diene	C29H46	76.604	1.01	394
52	Olean-12-en-3-ol, acetate, (3beta)-	C32H52O2	77.641	0.69	468
53	γ-Sitostenone	C29H48O	77.852	0.27	412
54	alpha-Fernenol	C30H50O	78.139	0.51	426
55	Methyl Commate A	C32H52O4	79.121	3.57	470
56	beta-Simiarenol	C30H50O	79.631	1.25	426
				100

Compounds are categorized according to different classes.

Alcohol and derivatives (1,14,17,23,27,54); Aldehydes and ketones (2,4,10,11,25,28,29,53); Alkanes and hydrocarbons (5,16,31,34,39); Aromatic compounds and derivatives (3,12,13,32,33,36,42); Carboxylic acids and derivatives (8,9,20,26,30,35,18,21,22,24); Esters and lactones (7,27,55); Steroids and Terpenes (6,13,46,47,48,50,51,52,56); and Miscellaneous (19,37,38,40,41,43,44,45,49).

Table 5. The results of GC-MS of hexane extract of leaves of Vinca rosea.

Peaks	Compound name	Molecular formula	Retention time	Area %	m/z
1	n-Hexane	C6H14	3.03	0.15	86
2	3-methylpentane	C6H14	3.25	6.9	86
3	2,3-Dimethylpentane	C7H16	3.5	12.61	100
4	3-Ethyl-2,2-dimethylpentane	C9H20	3.78	2.67	128
5	Sulphuric acid dibutyl ester	C8H18O4S	4.08	8.02	210
6	2,4-Dimethylhexane	C8H18	5.74	1.31	114
7	1-Methyl-2-pyrrolidinone	C5H9NO	6.3	4.28	99
8	5,7-Dimethylundecane	C13H28	7.25	0.99	184
9	3-Methyldecane	C11H24	8.2	0.38	156
10	2,5,9-Trimethyldecane	C13H28	8.74	1.76	184
11	6-Ethyl-2-methyldecane	C13H28	8.92	0.33	184
12	trans-1-Butyl-2-methylcyclopropane	C8H16	9.09	0.24	112
13	1,14-Tetradecanediol	C14H30O2	9.38	0.19	230
14	2-Hexyl-1-octanol	C14H30O	9.5	0.24	214
15	2,3,6-Trimethyloctane	C11H24	9.76	0.92	156
16	4,7-Dimethylundecane	C13H28	10.17	1.83	184
17	2-Hexyl-1-octanol	C14H30O	10.84	0.24	214
18	10-Methylnonadecane	C20H42	10.96	0.11	282
19	2,6,10,14-Tetramethylheptadecane	C21H44	11.04	0.21	296
20	2,7,10-Trimethyldodecane	C15H32	11.2	0.33	212
21	2,4,6-Trimethyloctane	C11H24	11.52	1.46	156
22	Cedrene	C15H24	12.07	0.44	204
23	2,5,5,6,8a-Pentamethyl-trans-4a,5,6,7,8,8a-hexahydro-gamma-chromene	C14H24O	12.33	0.28	208
24	Dihydroactinidiolide	C11H16O2	13.29	0.42	180
25	O-Decylhydroxylamine	C10H23NO	14.03	0.52	173
26	Nojigiku acetate	C12H18O2	14.61	0.52	194
27	4-(3-Hydroxybutyl)-3,5,5-trimethylcyclohex-2-en-1-one	C13H22O2	15.28	0.24	210
28	Sulfurous acid, decyl 2-pentyl ester	C15H32O3S	16.28	0.37	292
29	6,10,14-Trimethylpentadecan-2-one	C18H36O	16.71	0.65	268
30	Methyl 14-methylpentadecanoate	C17H34O2	17.55	0.71	270
31	Palmitic acid	C16H32O2	18.01	8.9	256
32	Phytol	C20H40O	19.38	3.88	296
33	(6Z,9Z)-Pentadeca-6,9-dien-1-ol	C15H28O	19.71	12.32	224
34	1,2-Epoxyoctadecane	C18H36O	21.19	0.13	268
35	7-Methyl-Z-tetradecen-1-ol acetate	C17H32O2	21.77	0.23	268
36	Cholesterol	C27H46O	22.21	5.59	386
37	Palmitic acid, 2-(octadecyloxy)ethyl ester	C36H72O3	23.87	0.54	553
38	Phthalic acid, di(6-methylhept-2-yl) ester	C24H38O4	24.37	3.19	390
39	Benzyl oleate	C25H40O2	26.12	1.01	372
40	Butyl oleate	C22H42O2	28.02	0.39	338
41	2-methyltetracosane	C25H52	28.16	0.28	352
42	26-Nor-5-cholesten-3á-ol-25-one	C26H42O2	28.89	14.25	386
				100.03

Compounds are categorized according to different classes.

Alkanes (1,2,3,4,6,8,9,10,11,15,16,18,19,20,21,29,41); Alcohols and derivatives (13,14,17,33,32,35); Esters (5,25,26,28,30,37,38,39,40); Ketones (24,27,29); Carboxylic acids and derivatives (31,37,42); Cycloalkanes and derivatives (12,22,23,27); Ethers (7,34); and Steroids and Sterols (36,42).

Figure 5. Percent mycelial growth inhibition of different treatments against F. graminearum.

Figure 6. Percent mycelial growth inhibition of different treatments against B. sorokiniana.

Table 6. ED₅₀ and ED₉₀ value of different treatments against F. graminearum and B. sorokiniana.

	F. graminearum			B. sorokiniana
Components	Tukey test mean	ED50	ED90	TUKEY TEST MEAN	ED50	ED90
		(µg ml^-1)	(µg ml^-1)		(µg ml^-1)	(µg ml^-1)
Methanol Extract	91.472^ab	80	240	90.532^ab	76	290
Hexane Extract	21.508^d	>1000	>1000	18.519^d	>1000	>1000
Essential Oil	77.089^c	98	865	74.286^c	100	875
Tilt (25 EC)	100.00^a	62.5	110	100.00^a	62.5	110

CD (1 % interaction): Components (A): 0.477 Concentration (B): 0.477 (A) x (B): 0.954.

Percent inhibition of all the components was significantly different from each other with P-value of 0.01.

Adams, R. P. (2007). Identification of essential oil components by gas chromatography/mass spectrometry (4th ed.). Allured Publishing Corporation.

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