Volatile compounds in wild strawberry and their odorants of wild strawberry wines: Effects of different stages of fermentation

Figures & data

Table 1. Physicochemical parameters of the wild strawberry wine.

Parameters	Content
Alcohol content (%)	10.7 ± 0.3
Residual sugars (g/L)	5.96 ± 0.26
Titratable acid (g/L)	8.05 ± 0.14
Volatile acid (g/L)	0.71 ± 0.03
Free SO2 (mg/L)	12.8 ± 0.27
Total SO2 (mg/L)	76.4 ± 0.18
pH	3.71 ± 0.11

Figure 1. Change of volatiles through the course of fermentation; A: different kinds of volatiles in total; B: alcohols; C: other esters;D: ethyl esters; E: acids; F: aldehydes and ketones; G: volatile phenols; H: terpenes and styrene.

Table 2. Volatiles with OAV above 1 of different stages during fermentation (n = 3).

RI	Numbers	Aroma compounds	Perception Threshold (mg/L)	Fruit (mg/L)	Early (mg/L)	Middle (mg/L)	Late (mg/L)	Finish (mg/L)	10 days after bottling (mg/L)
977	1	methyl 2-methylbutyrate	0.001^c	264.0	138.0	83.0	39.0	2.0	1.0
1830	2	phenethyl acetate	0.25^a	0.0	0.0	11.9	11.9	35.4	6.9
890	3	ethyl acetate	15^b	0.2	0.5	1.3	2.3	4.1	5.5
1064	4	ethyl 2-methylbutyrate	0.001^d	89.0	63.0	68.0	96.0	64.0	55.0
1095	5	ethyl 3-methylbutyrate	0.003^d	304.3	330.0	351.3	280.0	115.7	40.3
1232	6	ethyl hexanoate	0.014^a	0.6	0.8	3.5	3.7	9.2	4.3
1437	7	ethyl octanoate	0.005^e	29.6	2.8	12.0	11.0	158.4	25.8
2055	8	ethyl cinnamate		–	–	–	–	–	–
1220	9	isopentanol	30^a	0.3	0.5	1.2	1.4	7.2	4.2
1365	10	(E)-3-hexen-1-ol	1^b	9.1	1.0	0.0	0.0	4.1	1.5
1351	11	1-octen-3-ol	0.01^c	1.8	0.7	1.1	1.2	1.5	0.6
1557	12	1-octanol	0.12	0.1	2.8	8.6	10.0	22.3	9.6
1579	13	2,3-butanediol	120^g	0.6	0.2	0.4	0.3	2.8	1.4
1926	14	2-phenylethanol	14^a	0.3	1.3	4.3	4.2	15.6	0.0
1290	15	Octanal	0.05^b	0.9	2.2	4.1	4.1	0.1	0.7
1611	16	4-methoxy-2,5-dimethyl-3(2H)-furanone	0.016^c	1.3	27.9	33.4	22.7	36.4	15.1
1651	17	phenylacetaldehyde	–	–	–	–	–	–	–
1833	18	β-damascenone	0.00005^d	60.0	60.0	20.0	–	–	140.0
2076	19	Eugenol	0.006^a	0.5	1.2	3.8	3.0	3.8	1.0
1455	20	1-heptanol	0.2^f	0.5	0.9	1.1	1.2	1.7	0.7
1462	21	6-methyl-5-hepten-2-ol	0.16^c	0.1	1.0	1.0	1.1	1.4	0.6

^aÁlvarez M.G et al. 2011; ^bMoyano, L et al. 2002; ^cDu et al. 2011; ^dGuth 1997; ^eWu et al. 2011b; ^fCai et al. 2014; ^gJiang and Zhang 2010.

Table 3. The aroma compounds identified and their concentrations in the wild strawberry wine during fermentation (mg/L).

RI^a	Quantitative ion (m/z)^b	Aroma compounds	CAS	Fruit		Early		Middle		Late		Finish		10 days after bottling
				Mean	SD	Mean	SD	Mean	SD	Mean	SD	Mean	SD	Mean	SD
977	57	methyl 2-methylbutyrate	868-57-5	0.264a	0.015	0.138b	0.078	0.083bc	0.01	0.039c	0.005	0.002c	0	0.001c	0
1172	56	butyl formate	592-84-7	0.007a	0	0.001b	0.001	0.004c	0	0.008d	0	–	–	0.004c	0
1272	43	hexyl acetate	142-92-7	0.003a	0	0.004a	0	0.340b	0.001	0.367c	0.017	0.661d	0.004	0.071e	0.005
1402	73	methyl 2-hydroxy-3-methylbutanoate	17417-00-4	0.005a	0	0.013b	0	0.013b	0	0.013b	0	0.022c	0	0.010d	–
1416	88	methyl 3-hydroxy-2-methylpropionate	80657-57-4	0.014a	0.001	0.004b	0.001	0.005b	0.001	0.003b	0	0.011c	0.001	0.005b	–
1724	85	γ-Decalactone	706-14-9	0.003a	0	0.006b	0	0.008c	0	0.005b	0	0.012d	0.001	0.005b	0.001
1830	104	phenethyl acetate	103-45-7	0.001a	0	0.006a	0	2.964b	0.052	2.966b	0.063	8.838c	0.193	1.727d	0.066
		∑other esters		0.2963a	0.016	0.172b	0.077	3.415c	0.01	3.401c	0.022	9.546d	0.006	1.822e	0.005
890	43	ethyl acetate	141-78-6	2.534a	0.156	7.526b	0.145	18.847c	0.558	34.061d	0.876	62.014e	1.874	81.865f	2.857
1064	102	ethyl 2-methylbutyrate	7452-79-1	0.089a	0.004	0.063a	0.05	0.068a	0.055	0.096 a	0.002	0.064a	0	0.055a	0.001
1095	88	ethyl 3-methylbutyrate	108-64-5	0.913ab	0.107	0.990ab	0.133	1.054a	0.031	0.840b	0.036	0.347c	0.015	0.121d	0.001
1232	88	ethyl hexanoate	123-66-0	0.009a	0	0.011a	0.001	0.049b	0.001	0.052c	0.003	0.129d	0.001	0.060e	0.001
1255	83	ethyl tiglate	5837-78-5	0.009a	0	0.005b	0	0.006c	0	0.003d	0	–	–	–	–
1346	97	(E)-ethyl-hex-2-enoate	27829-72-7	0.002a	0	0.002a	0	0.005b	0	0.004bc	0	0.003c	0	0.001d	0
1416	73	ethyl 2-hydroxy-3-methyl butanoate	2441-06-7	0.012a	0.001	0.015b	0.001	0.014b	0	0.011a	0	0.028c	0	0.012a	0
1602	73	ethyl 3-hydroxy-2-methyl butanoate	18267-36-2	0.013a	0.001	0.204b	0.002	0.178c	0.021	0.146d	0.001	0.200b	0.001	0.100e	0.006
1437	88	ethyl octanoate	106-32-1	0.148a	0.016	0.014b	0.001	0.060c	0.003	0.055c	0.002	0.792d	0.01	0.129a	0.004
1639	88	ethyl decanoate	110-38-3	0.171a	0.01	0.003b	0.001	0.019b	0.003	0.014b	0.002	0.122c	0.011	0.018b	0.001
1678	105	ethyl benzoate	93-89-0	0.002a	0	0.021ab	0	0.073bc	0.001	0.089c	0.001	0.230d	0.033	0.143e	0.04
1694	55	ethyl trans-2-decenoate	7367-88-6	0.250a	0.021	0.001b	0	0.003b	0.001	0.002b	0	0.069c	0.001	–	–
1736	85	ethyl 3-oxoheptanoate	7737-62-4	0.005a	0	0.063b	0.007	0.120c	0.001	0.088d	0.013	0.122c	0.001	0.041e	0
1816	120	ethyl 2-hydroxy-benzoate	118-61-6	0.002a	0	0.002b	0	0.012c	0	0.015d	0	0.041e	0.001	0.016d	0
1848	88	ethyl laurate	106-33-2	0.002a	0	0.001a	0	0.013b	0.005	0.011b	0	0.018c	0	0.003a	0
1898	104	ethyl 3-phenylpropionate	2021-28-5	0.001a	0	0.006a	0	0.746b	0.002	0.764b	0.001	1.937c	0.001	0.282d	0.001
2055	177	ethyl cinnamate	103-36-6	0.014a	0	0.020a	0.004	0.110a	0.003	0.132a	0.005	0.428a	0.037	11.162b	0.63
1350	45	ethyl lactate	97-64-3	–	–	0.032a	0	0.033a	0	0.032a	0.001	0.071b	0.001	0.424c	0.007
		∑ethyl esters		4.176a	0.265	8.978b	0.32	21.409c	0.576	36.416d	0.935	66.316e	1.524	94.431f	3.603
1057	31	1-propanol	71-23-8	2.320a	0.222	0.222b	0.091	0.408b	0.22	0.988 c	0.123	6.111d	0.122	3.030e	0.156
1111	43	isobutanol	78-83-1	0.804a	0.021	0.734a	0.072	2.933a	1.401	17.417b	1.381	14.057c	0.976	13.892c	0.092
1220	70	isopentanol	123-51-3	9.584a	0.154	14.631a	3.54	36.059b	4.468	40.691b	0.586	215.597c	7.821	127.297d	6.889
1255	42	1-pentanol	71-41-0	0.110a	0.004	0.120a	0.008	0.118a	0	0.056b	0.029	0.006c	0	0.002c	0
1319	57	(Z)-2-heptanol	543-49-7	0.047a	0.012	0.016b	0.001	0.017b	0	0.020bc	0.001	0.031c	0.001	0.012b	0
1355	56	1-hexanol	111-27-3	–	–	4.100a	0.276	4.602b	0.071	4.511b	0.081	6.443c	0.127	2.667d	0.067
1365	41	(E)-3-hexen-1-ol	928-97-2	9.128a	0.019	1.036bc	1.42	0.030b	0.001	0.031b	0.002	4.051d	0.145	1.546c	0.105
1387	82	(Z)-3-hexen-1-ol	33467-74-2	0.011a	0.001	0.147b	0.004	0.122c	0.018	0.094d	0	0.187e	0	0.008a	0
1392	59	3-octanol	589-98-0	0.025a	0.001	0.016b	0.001	0.033c	0.001	0.049d	0.002	0.072e	0	0.027a	0.001
1351	57	1-octen-3-ol	3391-86-4	0.018a	0.001	0.007b	0	0.011c	0.001	0.012c	0	0.015d	0	0.006b	0.001
1455	70	1-heptanol	111-70-6	0.109a	0.002	0.172b	0.005	0.216c	0.009	0.235c	0.004	0.343d	0.02	0.132a	0.004
1462	95	6-methyl-5-hepten-2-ol	1569-60-4	0.009a	0.001	0.163b	0.001	0.167b	0.007	0.171b	0.001	0.224c	0.007	0.101d	0.015
1490	57	2-ethyl-1-hexanol	104-76-7	0.033a	0.003	0.005b	0	0.010c	0.001	0.013c	0	0.016d	0.001	0.006b	0.001
1502	81	cis-4-hepten-1-ol	6191-71-5	0.121a	0.014	0.015b	0	0.010b	0	0.020b	0	0.012b	0	0.007b	0
1517	45	2-nonanol	628-99-9	–	–	–	–	0.002	0	0.003	0.001	0.005	0	0.002	0
1557	56	1-octanol	111-87-5	0.008a	0.001	0.338b	0.018	1.032c	0.005	1.199c	0.012	2.671d	0.001	1.154c	0.182
1579	45	2,3-butanediol	123513-85-9	72.6a	22.344	20.140b	6.746	52.051c	14.912	40.415bc	10.185	338.919d	4.942	162.426e	4.478
1615	67	(Z)-5-octen-1-ol	64275-73-6	0.003a	0	0.077b	0.002	0.134c	0.004	0.125d	0.001	0.178e	0	0.071f	0.002
1662	56	1-nonanol	143-08-8	0.025a	0.006	0.020a	0	0.064b	0.004	0.072b	0.002	0.213c	0.008	0.085d	0.004
1765	70	1-decanol	112-30-1	0.005a	0.001	0.001b	0	0.006a	0	0.011c	0	0.062d	0	0.024e	0.002
1890	79	benzyl alcohol	100-51-6	0.039ab	0.002	0.277c	0.006	0.049ad	0.008	0.036b	0.002	0.052d	0.002	0.087e	0.003
1926	91	2-phenylethanol	60-12-8	4.023a	0.322	17.916b	0.502	60.430c	0.774	58.925c	4.922	218.237d	11.278	0.052a	0.005
2046	91	3-phenylpropanol	122-97-4	0.014a	0.001	0.208b	0.021	0.533c	0.008	0.390d	0.063	0.840e	0.004	0.243b	0.002
		∑alcohols		99.036a	22.816	60.359b	1.58	159.038c	20.19	165.483c	13.196	808.341a	0.322	312.878d	11.486
1146	83	mesityl oxide	141-79-7	0.007a	0.001	0.002ab	0.001	0.008a	0.004	0.006ab	0.004	0.003ab	0	0.001b	0
1187	57	diisobutyl ketone	108-83-8	0.076a	0.012	0.082ab	0.019	0.099ab	0.012	0.107b	0.001	0.034c	0.001	0.152d	0.013
1290	43	octanal	124-13-0	0.047a	0.001	0.109b	0.016	0.207c	0.009	0.207c	0.027	0.005d	0	0.037ad	0.001
1298	45	acetoin	513-86-0	11.820a	0.383	15.941b	0.381	12.982c	0.423	0.354d	0.025	0.667d	0.009	29.815e	0.649
1325	43	6-methyl-5-hepten-2-one	110-93-0	0.007a	0.001	0.012b	0.001	0.014c	0.001	0.014c	0	0.019d	0.001	0.009e	0.001
1394	57	1-nononal	124-19-6	0.014ab	0.001	0.007c	0.001	0.013a	0.001	0.015b	0.001	0.003d	0	0.001e	0
1534	77	benzaldehyde	100-52-7	0.003a	0	0.146b	0.003	0.394c	0.01	0.388c	0.006	0.968d	0.062	0.410c	0.001
1611	43	4-methoxy-2,5-dimethyl-3(2H)-furanone (DMMF)	4077-47-8	0.020a	0	0.447b	0.005	0.534c	0.055	0.363d	0.041	0.582c	0.012	0.241e	0.005
1651	91	phenylacetaldehyde	122-78-1	0.063a	0.002	0.016b	0.001	0.034c	0.001	0.029d	0.001	0.046e	0.004	0.022f	0.001
		∑aldehydes and ketones		12.058a	0.395	16.762b	0.334	14.286c	0.473	1.483d	0.045	2.326d	0.066	30.687e	0.659
1164	93	β-myrcene	127-91-3	0.008a	0	0.008a	0.004	0.020b	0.001	0.019b	0.001	0.019b	0	0.008a	0
1193	68	limonene	5138-86-3	–	–	0.006a	0	0.009b	0.001	0.001c	0	0.004d	0	–	–
1240	93	(Z)-β-ocimene	3338-55-4	0.007a	0	0.010b	0	0.020c	0.001	0.001d	0	0.050e	0.002	0.019c	0
1290	93	terpinolene	586-62-9	–	–	0.001a	0	0.002a	0.001	0.002a	0.001	0.005b	0	0.002a	0
1547	71	linalool	78-70-6	0.003a	0	0.007b	0.001	0.018cd	0.002	0.021c	0	0.036e	0.001	0.016d	0.002
1703	59	α-terpineol	10482-56-1	0.007a	0.001	0.003b	0.001	0.006a	0	0.007a	0	0.017c	0.001	0.008a	0.001
1770	69	citronellol	106-22-9	0.019a	0.001	–	–	0.001b	0	0.001b	0	0.016a	0.002	0.012c	0.003
1833	69	β-damascenone	23696-85-7	0.003a	0	0.003a	0	0.001b	0	–	–	0.010c	0.001	0.007d	–
1864	43	geranylacetone	689-67-8	0.002a	0	0.003b	0	0.008c	0	0.013d	0	0.018e	0.001	0.008c	0
		∑terpenes		0.049a	0.001	0.041a	0.007	0.085b	0.002	0.065c	0	0.175d	0.004	0.080b	0.006
1590	43	isobutyric acid	79-31-2	0.618a	0.023	1.803b	0.012	3.369c	0.262	3.403c	0.2	12.680d	0.915	7.518e	0.165
1668	74	2-methylhexanoic acid	4536-23-6	0.147a	0.008	0.428b	0.01	0.512bc	0.042	0.475bc	0.034	0.990d	0.066	0.542c	0.003
		∑acids		0.765a	0.03	2.232b	0.002	3.880c	0.304	3.878c	0.235	13.670d	0.848	8.059e	0.168
1746	138	1,2-dimethoxybenzene	91-16-7	0.005a	0	0.009b	0.001	0.021c	0	0.019c	0	0.031d	0.002	0.012e	0
2020	94	phenol	108-95-2	0.031a	0.002	0.015b	0.001	0.032a	0	0.029a	0.003	0.065c	0.002	0.115d	0.007
2027	164	isoeugenol	97-54-1	0.015a	0.001	0.016a	0.002	0.052b	0.001	0.048b	0.004	0.074c	0.001	0.030d	0.001
2049	137	4-ethyl guaiacol	2785-89-9	0.011a	0.002	0.009a	0.001	0.043b	0.001	0.051b	0.005	0.105c	0.008	0.144d	0.005
2076	164	eugenol	97-53-0	0.003a	0.001	0.007b	0.001	0.023c	0.001	0.018d	0.002	0.023c	0	0.006b	0
		∑phenols		0.068a	0.002	0.063a	0.006	0.187b	0.004	0.179b	0.015	0.320c	0.009	0.315c	0.003
1263	104	styrene	100-42-5	0.291a	0.008	0.403b	0.01	0.563c	0.038	0.527c	0.006	0.710d	0.005	0.422b	0.011
		∑total volatiles		116.74a	23.47	89.006b	1.464	202.852c	21.589	211.422c	14.398	901.393d	2.624	448.692e	15.919

^aRetention indices were calculated on HP-INNOWAX column. ^bQuantitative ion for peak area evaluation of volatile compounds. Results are the means of three independent experiments ± standard deviation. Values with different letters in the same row are significantly different according to the Duncan test (p < 0.05).

Table 4. Concentrations of volatiles with OAV above 1 and its perception thresholds of different stages during fermentation (n = 3).

RI	Numbers	Aroma compounds	Quantitative standards	Perception Threshold (mg/L)	Fruit(mg/L)	Early(mg/L)	Middle (mg/L)	Late(mg/L)	Finish (mg/L)	10 days after bottling (mg/L)
977	1	methyl 2-methylbutyrate	methyl 2-methylbutyrate	0.001^c	0.264	0.138	0.083	0.039	0.002	0.001
1830	2	phenethyl acetate	phenethyl acetate	0.25^a	0.001	0.006	2.964	2.966	8.838	1.727
890	3	ethyl acetate	ethyl acetate	15^b	2.534	7.526	18.847	34.061	62.014	81.865
1064	4	ethyl 2-methylbutyrate	ethyl 2-methylbutyrate	0.001^d	0.089	0.063	0.068	0.096	0.064	0.055
1095	5	ethyl 3-methylbutyrate	ethyl 2-methylbutyrate	0.003^d	0.913	0.99	1.054	0.84	0.347	0.121
1232	6	ethyl hexanoate	ethyl hexanoate	0.014^a	0.009	0.011	0.049	0.052	0.129	0.06
1437	7	ethyl octanoate	ethyl octanoate	0.005^e	0.148	0.014	0.06	0.055	0.792	0.129
2055	8	ethyl cinnamate	–		0.014	0.02	0.11	0.132	0.428	11.162
1220	9	isopentanol	1-butanol	30^a	9.584	14.631	36.059	40.691	215.597	127.297
1365	10	(E)-3-hexen-1-ol	(E)-3-hexen-1-ol	1^b	9.128	1.036	0.03	0.031	4.051	1.546
1351	11	1-octen-3-ol	1-octen-3-ol	0.01^c	0.018	0.007	0.011	0.012	0.015	0.006
1557	12	1-octanol	1-octanol	0.12	0.008	0.338	1.032	1.199	2.671	1.154
1579	13	2,3-butanediol	2,3-butanediol	120^g	72.6	20.14	52.051	40.415	338.919	162.426
1926	14	2-phenylethanol	2-phenylethanol	14^a	4.023	17.916	60.43	58.925	218.237	0.052
1290	15	Octanal	Octanal	0.05^b	0.047	0.109	0.207	0.207	0.005	0.037
1611	16	4-methoxy-2,5-dimethyl-3(2H)-furanone	–	0.016^c	0.02	0.447	0.534	0.363	0.582	0.241
1651	17	phenylacetaldehyde	phenylacetaldehyde	–	0.063	0.016	0.034	0.029	0.046	0.022
1833	18	β-damascenone	–	0.00005^d	0.003	0.003	0.001	–	0.010c	0.007
2076	19	Eugenol	Eugenol	0.006^a	0.003	0.007	0.023	0.018	0.023	0.006
1455	20	1-heptanol	1-heptanol	0.2^f	0.109	0.172	0.216	0.235	0.343	0.132
1462	21	6-methyl-5-hepten-2-ol	6-methyl-5-hepten-2-ol	0.16^c	0.009	0.163	0.167	0.171	0.224	0.101

^aGonzalez Alvarez et al. 2011; ^bMoyano et al. 2002; ^cDu et al.^{[3]; d}Guth^{[39]; e}Wu et al. 2011b; ^fCai et al. 2014; ^gJiang and Zhang 2010.

The data represents the average value.

Figure 2. Principal component analysis (PCA) of volatile compounds with OAV above 1 in wines by GC/MS. These volatiles were numbered in sequence according to Table 3. The data represents the average value.

Figure 3. Descriptive analysis of aroma profile in wild strawberry fruit and wine. Wild strawberry fruit – triangle markers and wines – square markers, evaluated by the tasting panel.

Du, X.; Plotto, A.; Baldwin, E.; Rouseff, R. Evaluation of Volatiles from Two Subtropical Strawberry Cultivars Using GC-Olfactometry, GC-MS Odor Activity Values, and Sensory Analysis. Journal of Agricultural and Food Chemistry 2011, 59(23), 12569–12577.

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Guth, H. Quantitation and Sensory Studies of Character Impact Odorants of Different White Wine Varieties. Journal of Agricultural and Food Chemistry 1997, 45(8), 3027–3032.

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