Volatile constituents of unripe and ripe kundang fruits (Bouea macrophylla Griffith)

Figures & data

Figure 1. A: Unripe; and B: ripe kundang fruits.

Table 1. The major chemical compounds identified in unripe and ripe kundang fruits oil.

Compounds	Unripe		Ripe
	amount (%)	Number of compounds	amount (%)	Number of compounds
Terpene hydrocarbons	32.89	37	29.28	57
Aldehydes	0.35	1	1.02	5
Alcohols	2.83	11	9.35	19
Ketones	16.85	4	27.27	10
Esters	17.32	21	20.73	24
Acids	29.72	9	9.68	6
Total	99.96	82	97.33	121

Table 2. Chemical composition of the essential oil from unripe kundang fruits.

Chemical compound		RT	%
Terpene hydrocarbons			32.89
1	delta-Cadinene	-	4.80
2	α-Terpineol	24.11	1.25
3	β-Terpineol	24.26	0.22
4	Neral	27.52	0.26
5	Rose oxide	28.05	0.54
6	Santolinatriene	28.20	0.24
7	Eugenol	29.80	0.50
8	α-Copaene	30.30	0.48
9	Isogermacrene D	33.61	0.53
10	α-amorphene	33.68	0.40
11	β-Maaliene	33.99	0.16
12	Zingiberene	34.16	0.51
13	α-Muurolene	34.56	1.14
14	β-Bisabolene	34.57	0.09
15	γ-Muurolene	34.86	0.37
16	γ-Cadinene	34.86	0.53
17	Zonarene	35.13	0.24
18	α-Cadinene	35.57	0.17
19	Valencene	35.64	0.24
20	Selina-3,7(11)-diene	35.67	0.27
21	Cadina-1(6),4-diene	35.80	0.44
22	γ-Gurjunene	36.78	0.51
23	Caryophyllene alcohol	36.96	0.96
24	Viridiflorol	37.22	0.26
25	Globulol	37.23	0.48
26	Cubeban-11-ol	37.54	0.34
27	1,10-di-epi-Cubenol	37.82	0.90
28	Spathulenol	37.83	0.83
29	Copaborneol	37.96	0.24
30	Cubenol	38.22	3.45
31	γ-Eudesmol	38.56	0.97
32	α-Muurolol	38.98	1.38
33	α-Cadinol	39.05	4.94
34	Tumerone	39.52	3.65
35	Aristolone	40.33	0.15
36	Curlone	40.54	0.39
37	Andrographolide	42.58	0.06
Oxygenated compounds		RT	%
Aldehydes (Total)			0.35
38 2-Isopropylidene-3-methylhexa-3,5-dienal		30.90	0.35
Alcohols (Total)			2.83
39	Linalool oxide	19.54	0.52
40	1-(2-Methylenecyclohexyl)-1-phenylethanol	19.76	0.15
41	2,6-dimethyl-5,7-Octadien-2-ol	22.85	0.35
42	Artemisia alcohol	23.21	0.24
43	3,3,6-trimethyl-4,5-Heptadien-2-ol	23.91	0.16
44	(E,E)-2,6-Dimethyl-3,5,7-octatriene-2-ol	27.37	0.28
45	cis-p-Mentha-2,8-dien-1-ol	27.51	0.25
46	3-(5’,5’-Dimethyltetrahydrofuran-2’-yl)-cis-2-buten-1-ol	28.09	0.38
47	1,4,4-trimethyl-tricyclo[6.3.1.02,5]dodecan-8-ol	36.95	0.34
48	1-Hexadecanol	45.02	0.16
Ketones (Total)			16.85
49	5,6-Decanedione	2.56	13.99
50	Bicyclo[3.3.1]nonane-2,7-dione	18.50	0.16
51	Acetophenone	18.96	2.59
52	2,2,7,7-Tetramethyltricyclo[6.2.1.0(1,6)]undec-4-en-3-one	40.34	0.11
Esters (Total)			17.32
53	Butanoic acid, 3-hexenyl ester, (Z)-	24.01	0.09
54	cis-3-Hexenyl iso-butyrate	24.02	0.06
55	cis-8,11,14-Eicosatrienoic acid methyl ester	30.03	0.41
56	Geranyl acetate	30.41	0.21
57	Propanoic acid, 2-methyl-, 1-(1,1-dimethylethyl)-2-methyl-	36.88	0.11
	1,3-propanediyl ester
58	Sulfurous acid, 2-propyl undecyl ester	37.10	0.17
59	Diethyl Phthalate	37.31	0.54
60	Ergostane-3,5,6,12,25-pentol, 25-acetate, (3.beta.,5.alpha.,6	39.13	0.14
61	1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester	44.67	0.19
62	Hexadecanoic acid, methyl ester (methyl hexadecanoate)	46.08	0.37
63	Dibutyl phthalate	46.78	1.96
64	Docosanoic acid, ethyl ester	47.72	0.65
65	Isopropyl Palmitate	48.38	0.10
66	1-Propene-1,2,3-tricarboxylic acid, tributyl ester	51.69	0.30
67	Acetyl tributyl citrate	53.63	0.48
68	Hexanedioic acid, bis(2-ethylhexyl) ester	56.52	6.96
69	Hexanoic acid, 2-ethyl-, octadecyl ester	58.06	0.15
70	5-Bromopentanoic acid, 2-methylphenyl ester	58.65	0.13
71	Oxalic acid, 2-methylphenyl tetradecyl ester	58.94	0.96
72	Decanedioic acid, bis(2-ethylhexyl) ester	59.08	2.82
73	1,2-Benzenedicarboxylic acid, bis(2-ethylhexyl	59.45	0.52
Acids (Total)			29.72
74	Trimethylacetic anhydride	2.12	22.16
75	Caprylic acid	23.07	0.18
76	Octanoic acid	23.11	0.23
77	Nonanoic acid	26.75	0.29
78	Decanoic acid	30.10	0.25
79	Dodecanoic acid	36.29	0.49
80	Myristic acid	41.88	0.12
81	Heptadecanoic acid (Margaric acid)	47.08	2.69
82	Hexadecanoic acid (Palmitic acid)	47.08	3.31

Results are average mean of three independent replicates with standard error detected < ± 0.01.

Table 3. Chemical composition of the essential oil from ripe kundang fruits.

Chemical compound		RT	%
Terpene hydrocarbons (Total)			29.28
1	Delta-Cadinene	-	1.32
2	4-Diene -Cadina-1(6)	-	0.68
3	Dill Ether	19.89	0.12
4	β-Terpineol	22.29	0.09
5	Cis-Ocimenol	22.84	0.60
6	α-Terpineol	24.10	4.41
7	Trans-Verbenol	24.56	0.08
8	γ-Terpinene	24.70	0.06
9	Trans-(+)-Carveol	25.02	0.44
10	Phellandral	25.03	0.42
11	Neral	27.51	0.21
12	Thymol	27.64	0.55
13	Santolinatriene	28.21	0.25
14	Eugenol	29.80	0.12
15	α-Copaene	30.30	0.57
16	Trans-Caryophyllene	30.41	0.04
17	α-Cis-Bergamotene	31.51	0.25
18	β-Caryophyllene	31.84	0.28
19	Isocaryophyllen	31.84	0.30
20	(Z)-Trans-Alpha-Bergamotene	32.13	0.13
21	α-Caryophyllene	33.04	0.05
22	Alloaromadendrene	33.19	0.09
23	Isogermacrene D	33.61	0.32
24	Ethyl-(E)-Cinnamate	33.71	0.28
25	(E)-Beta-Ionone	33.85	1.17
26	(Z,E)-Alpha-Farnesene	33.94	0.22
27	Valencene	34.16	0.19
28	Cadina-3,5-Diene	34.29	0.07
29	E,E-Alpha-Farnesene	34.38	2.34
30	β-Bisabolene	34.57	0.27
31	γ-Cadinene	34.87	0.19
32	Zonarene	35.15	0.14
33	7(11)-Diene-Selina-4(15)	35.65	0.28
34	γ-Maaliene	35.65	0.22
35	α-Maaliene	35.76	0.14
36	Selina-3,7(11)-Diene	35.76	0.11
37	Globulol	37.23	0.33
38	Cubeban-11-ol	37.54	0.42
39	Caryophyllene Oxide	37.72	0.07
40	Copaborneol	37.95	0.20
41	1,10-di-epi-Cubenol	38.22	2.84
42	γ-Eudesmol	38.56	0.59
43	Carotol	38.65	0.08
44	α-Muurolol	38.99	1.44
45	Cadin-4-En-10-ol	39.09	3.46
46	α-Bisabolol Oxide B	39.14	0.11
47	Ar-Tumerone	39.46	0.51
48	β-Bisabolol	39.58	0.35
49	Longicyclene	39.79	0.16
50	α-Bisabolol	40.06	0.33
51	Aristolone	40.33	0.06
52	Ledol	40.55	0.08
53	β-Copaen-4 .Alpha.-Ol	40.80	0.11
54	Farnesene	45.17	0.85
55	Farnesol	46.93	0.09
56	D-Nerolidol	46.93	0.10
57	Squalene	59.35	0.10
Oxygenated compounds		RT	%
Aldehydes (Total)			1.02
58	Octanal	7.92	0.10
59	Phenylacetaldehyde	18.05	0.13
60	Nonanal	20.36	0.16
61	Para-menth-3-en-7-al	27.37	0.55
62	2,4-Decadienal	28.66	0.08
Alcohols (Total)			9.35
63	Linalool Oxide	18.79	0.69
64	α,α-Dimethyl-Benzenemethanol	19.74	0.70
65	1-Methylcycloheptanol	20.69	0.12
66	2,6-Dimethylcyclohexanol	20.69	0.12
67	Artemisia Alcohol	23.21	1.10
68	2,2-Diethyl-1,3-Propanediol	23.69	0.05
69	2-Methyl-5-(1-Methylethenyl)-Cyclohexanol	24.26	0.44
82	3,5-Dimethyl-Benzenemethanol	24.70	0.06
70	Cis-p-mentha-1(7),8-dien-2-ol	26.09	0.29
71	2-Pentadecyn-1-ol	26.54	0.25
72	Cumin Alcohol	27.78	0.31
73	4-(1-Methylethenyl)-1-cyclohexene-1-methanol	28.03	0.45
75	Z3,Z6,E8-Dodecatrien-1-ol	28.21	0.18
83	p-mentha-1(7),8(10)-dien-9-ol	28.21	0.17
74	1,4-Cyclohexadiene-1-Methanol	29.04	0.24
76	Perillyl Alcohol	30.03	1.19
84	(Z,Z,Z)-8,11,14-Eicosatrienoic Acid	30.04	1.23
77	1-Naphthalenol, 1,2,3,4,4a,7,8,8a-Octahydro	37.82	0.46
78	Naphth-1-ol <1,2,3,4,4a,7,8,8a-Octahydro-, 4-Isopropyl-, 1,6-	38.85	0.54
79	Decahydro-1,4a-Dimethyl-7-(1-Methylvinyl)-1-Naphthalenol	39.70	0.19
85	1-Naphthalenol, Decahydro-1,4a-Dimethyl	39.70	0.14
80	1-Hexadecanol	45.03	0.27
81	n-Heptadecanol-1	49.97	0.16
Ketones (Total)			27.27
82	Acetyl Valeryl	2.16	10.99
83	1,3-cyclohexanedione	15.76	0.12
84	Acetophenone	18.95	12.31
85	(E)-beta-damascenone	30.60	0.14
86	2,7,7-Trimethyl-Bicyclo[3.1.1]hept-2-en-6-one	30.91	0.37
87	6,10-dimethyl-, (z)-5,9-undecadien-2-one	32.73	0.25
88	(E)-beta-Ionone	33.85	1.13
89	2(4H)-Benzofuranone, 5,6,7,7a-Tetrahydro-4,4,7a	35.85	0.64
90	5,6,7,7a-Tetrahydro-4,4,7a-Trimethyl-2(4H)-Benzofuranone	35.86	0.66
91	5,6,7,7a-Tetrahydro-4,4,7a-Trimethyl-2(4h)-Benzofuranone	35.86	0.66
Esters (Total)			20.73
92	Pentanoic acid, 2-propenyl ester	2.56	8.25
93	(Z)-Butanoic acid, 3-hexenyl ester	24.01	0.10
94	Ethyl cinnamate	33.70	0.28
95	Benzeneacetic acid, α,3,4-tris[(trimethylsilyl)oxy]-, trimethylsilyl ester	37.10	1.83
96	diethyl-Phthalate	37.31	0.25
97	Cis-Sesquisabinene hydrate	39.58	0.20
98	2-ethylhexyl-Salicylate	43.15	0.14
99	isopropyl-Tetradecanoate	43.43	0.09
100	1,2-benzenedicarboxylic acid, bis(2-methylpropyl) ester	44.67	0.12
101	Tetramethyl-2,6,10,14-hexadecatetraenoic acid	45.81	0.16
102	Methyl hexadecanoate	46.08	0.25
103	Ethyl-Palmitate	47.72	1.14
104	(Z,Z)-9,12-octadecadienoic acid	51.15	0.67
105	Ethyl-linoleate	51.65	0.40
106	9-octadecenoic acid (z)-, ethyl ester	51.77	0.39
107	Tributyl acetylcitrate	53.64	0.22
108	Hexanedioic acid, bis(2-ethylhexyl) ester	56.52	2.62
109	Decanedioic acid, bis(2-ethylhexyl) ester	59.09	1.30
110	Dioctyl phthalate,(dop)	59.46	0.17
111	Guaiac acetate	37.82	0.39
112	2,6,10,14-hexadecatetraenoic acid, 3,7,11,15-tetramethyl-, methyl	45.80	0.17
113	Hexadecanoic acid, methyl ester	46.08	0.24
114	Ethyl iso-allocholate	30.04	1.29
115	Benzyl benzoate	42.58	0.06
Acids (Total)			9.68
116	Caprylic acid	23.09	0.47
117	Nonanoic acid	26.67	0.19
118	Dodecanoic acid	36.33	2.01
119	Myristic acid	41.89	0.34
120	N-hexadecanoic acid	47.11	5.60
121	Oleic acid	51.27	1.07

RT: retention time.

Results are average mean of three independent replicates with standard error detected < ± 0.01.

Table 4. Comparison between the composition (%) of similar components of essential oil identified in unripe and ripe kundang fruits.

	Composition (%)
Chemical compound	Unripe	Ripe
1) Terpene hydrocarbons
Delta-Cadinene	4.80	1.32
Beta-Terpineol	0.22	0.09
Alpha-Terpineol	1.25	4.41
Neral	0.26	0.21
Santolinatriene	0.24	0.25
Eugenol	0.5	0.12
Alpha-Copaene	0.48	0.57
Isogermacrene D	0.53	0.32
Valencene	0.24	0.19
Gamma-Cadinene	0.53	0.19
Seline-3,7(11)-Diene	0.27	0.11
Globulol	0.48	0.33
Cubeban-11-ol	0.34	0.42
Copaborneol	0.24	0.2
Gamma-Eudesmol	0.97	0.59
Alpha-Muurolol	1.38	1.44
Aristolone	0.15	0.06
2) Alcohols
Linalool Oxide	0.52	0.69
Artemisia Alcohol	0.24	4.41
1-Hexadecanol	0.16	0.27
3) Esters
(Z)-Butanoic acid, 3-hexenyl ester	0.09	0.1
4) Acids
Caprylic acid	0.18	0.47
Nonanoic acid	0.29	0.19
Dodecanoic acid	0.49	2.01
Myristic acid	0.12	0.34