顶空固相微萃取-气相色谱-质谱联用法分析 欧李果实挥发性成分

doi:10.3864/j.issn.0578-1752.2019.19.014

摘要/Abstract

摘要：

【目的】 优化前处理影响因素,分析欧李果实挥发性成分,明确挥发性成分特点并对果实特征性香气成分进行评价。【方法】 以欧李果实为试材,采用顶空固相微萃取-气相色谱-质谱联用法（HS-SPME-GC-MS）测定其挥发物成分,通过优化前处理影响因素,确定最佳试验条件。利用解卷积系统（AMDIS）与NIST11质谱数据库以及保留指数（RI）对其挥发性成分进行鉴定,内标法确定挥发物含量,并计算香气强度值（OAVs）,评价欧李果实香气品质与特征。【结果】 在欧李果实中累计鉴定出63种挥发物,含量范围为0.01—3.25 μg·kg ^-1。挥发物以酯类、烷类为主,并有少数醇类、芳香类、醛类、萜类、酸类、酮类,其中苯甲酸乙酯含量最高。通过参考相关挥发物香气阈值并计算部分挥发物OAVs可知,己酸乙酯、乙酸苯乙酯、β-芳樟醇、乙酸己酯、壬醛等物质对欧李果实香气成分构成具有重要作用,而烷烃不具有特征性香气。欧李果实香气主要为青香、花香、果香、脂蜡香和其他少数香型（木香型、芳香油香型等）,并以青香、花香、果香型物质为主,三者总含量达到挥发物总量的80%。【结论】 优化确立的试验条件为：果肉去核切碎处理,取样量5 g,萃取温度50℃,萃取时间与平衡时间均为30 min。SPME前处理条件对果实挥发性成分检测到的种类与含量有较大影响,通过优化试验条件可以获得最佳检测结果。欧李果实挥发物组成复杂,除烃类物质香气品质较弱外,多数具有特征香气,且香气强度属中高级,酯类物质是欧李果实的重要挥发物组成,清香型、花香型和果香型是欧李果实香气成分的主要特点。

关键词: 欧李, 挥发性成分, 条件优化, 香气强度值, 香气品质

Abstract:

【Objective】 The objective of this study was to optimize the pretreatment conditions and to analyze the volatiles of Cerasus Humilis (Bge.) Sok, further to evaluate the characteristics of the main aroma components.【Method】 The fruit of Cerasus humilis (Bge.) Sok was used as material, the volatiles were determined by headspace solid phase microextraction coupled with gas chromatography-mass spectrometry (HS-SPME-GC-MS), and the pretreatment conditions were optimized. Automatic Mass Spectral Deconvolution and Identification System (AMDIS), NIST11 database and retention index (RI) were applied to volatiles identify, internal standard to contents calculate, final the odor-activity values (OAVs) and aroma qualities were evaluated.【Result】 Total of 63 volatiles were identified, namely main of esters and alkanes, few of alcohols, arenes, aldehydes, terpenes, acid and ketone, with ranges from 0.01 to 3.25 μg·kg ^-1, in which ethyl benzoate as the highest. The OAVs showed ethyl hexanoate, phenethyl acetate, β-linalool, hexyl acetate, and nonanal were the main aroma components, alkanes almost the odorless. Green, fruity, floral, waxy and less woody and oily aromatic formed the odor qualities, while the former three performed the main odors reached 80% content. 【Conclusion】 The conditions were optimized as follows: samples loading for 5 g after cored and chipping, extraction temperature was 50℃, and both extraction and balance time was 30 min. The pretreatment had great influence on the volatiles detection, and preferable results would be yield by optimizing conditions. Results showed esters were the main components, except alkanes, and the most of them had aroma characteristics, presented medium or high strength, while green, fruity, floral were the major odor types.

Key words: Cerasus humilis (Bge.) Sok, volatile components, optimization analysis, odor-activity values (OAVs), aroma quality

李晓颍,王海静,徐宁伟,曹翠玲,刘建珍,武春成,张立彬. 顶空固相微萃取-气相色谱-质谱联用法分析欧李果实挥发性成分[J]. 中国农业科学, 2019, 52(19): 3448-3459.

LI XiaoYing,WANG HaiJing,XU NingWei,CAO CuiLing,LIU JianZhen,WU ChunCheng,ZHANG LiBin. Analysis of Volatile Components in Cerasus Humilis (Bge.) Sok by Headspace Solid Phase Microextraction-Gas Chromatography-Mass Spectrometry[J]. Scientia Agricultura Sinica, 2019, 52(19): 3448-3459.

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图/表 9

图1

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表1

欧李果实挥发性成分及其含量"

序号 No.	挥发性成分 Volatile	分子式 Formula	分子量 Mass	保留时间 Retention time (min)	含量 Content (μg·kg^-1)	保留指数 RI		鉴定依据 Identification
序号 No.	挥发性成分 Volatile	分子式 Formula	分子量 Mass	保留时间 Retention time (min)	含量 Content (μg·kg^-1)	Cal.	Ref.	鉴定依据 Identification
醇类 Alcohol
1	2-乙基-己醇 2-Ethyl-hexanol	C₈H₁₈O	130	20.30	0.02	1034	1035	MS, RI
2	辛醇 Octanol	C₈H₁₈O	130	23.64	0.03	1083	1087	MS, RI
3	壬醇 Nonanol	C₉H₂₀O	144	29.12	0.28	1172	1171	MS, RI
4	(Z)-3-己烯-1-醇 (Z)-3-Hexen-1-ol	C₆H₁₂O	100	8.87	0.01	855	855	MS, RI
5	苯乙醇 Phenylethyl alcohol	C₈H₁₀O	122	26.05	0.15	1126	1121	MS, RI
芳香类 Arenes
6	邻二甲苯 o-Xylene	C₈H₁₀	106	9.60	0.06	870	879	MS, RI
7	萘 Naphthalene	C₁₀H₈	128	29.23	0.02	1174	1170	MS, RI
8	2-甲基萘 2-Methylnaphthalene	C₁₁H₁₀	142	33.81	0.03	1289	1289	MS, RI
酸类 Acids
9	苯甲醛 Benzaldehyde	C₇H₆O	106	14.96	0.12	956	961	MS, RI
10	壬醛 Nonanal	C₉H₁₈O	142	25.62	0.16	1117	1107	MS, RI
11	(E)-3-甲基-4-癸烯酸 (E)-3-Methyl-4-decenoic acid	C₁₁H₂₀O₂	184	37.59	0.06	1413	1415	MS, RI
萜类 Terpenoids
12	β-芳樟醇 β-Linalool	C₁₀H₁₈O	154	25.35	0.24	1111	1103	MS, RI
13	α-法呢烯 α-Farnesene	C₁₅H₂₄	204	39.63	0.1	1512	1512	MS, RI
烷类 Alkyls
14	2-壬酮 2-Nonanone	C₉H₁₈O	142	24.93	0.05	1102	1104	MS, RI
15	十二烷 Dodecane	C₁₂H₂₆	170	30.25	0.48	1200	1200	MS, RI
16	十三烷 Tridecane	C₁₃H₂₈	184	34.24	0.61	1300	1300	MS, RI
17	2-甲基-十三烷 2-Methyl-tridecane	C₁₄H₃₀	198	36.36	0.04	1369	1362	MS, RI
18	法呢烷 Farnesane	C₁₅H₃₂	212	36.72	0.08	1381	1378	MS, RI
19	十四烷 Tetradecane	C₁₄H₃₀	198	37.33	0.32	1400	1400	MS, RI
20	正辛基环己烷 Octylcyclohexane	C₁₄H₂₈	196	38.39	0.10	1451	1451	MS, RI
21	5-甲基-十四烷 5-Methyl-tetradecane	C₁₅H₃₂	212	38.51	0.07	1456	1454	MS, RI
22	4-甲基-十四烷 4-Methyl-tetradecane	C₁₅H₃₂	212	38.62	0.11	1462	1460	MS, RI
23	4,11-二甲基-十四烷 4,11-Dimethyl-tetradecane	C₁₆H₃₄	226	38.70	0.85	1465	1464	MS, RI
24	3-甲基-十四烷 3-Methyl-tetradecane	C₁₅H₃₂	212	38.87	0.14	1473	1470	MS, RI
25	十五烷 Pentadecane	C₁₅H₃₂	212	39.44	1.31	1500	1500	MS, RI
26	5-丙基-十三烷 5-Propyl-tridecane	C₁₆H₃₄	226	39.69	0.16	1515	1516	MS, RI
27	6-甲基-十五烷 6-Methyl-pentadecane	C₁₆H₃₄	226	40.29	0.06	1551	1551	MS, RI
28	壬基环已烷 n-Nonylcyclohexane	C₁₅H₃₀	210	40.37	0.22	1556	1556	MS, RI
29	4-甲基-十五烷 4-Methyl-pentadecane	C₁₆H₃₄	226	40.45	0.04	1560	1557	MS, RI
30	2-甲基-十五烷 2-Methyl-pentadecane	C₁₆H₃₄	226	40.53	0.15	1566	1564	MS, RI
序号 No.	挥发性成分 Volatile	分子式 Formula	分子量 Mass	保留时间 Retention time (min)	含量 Content (μg·kg^-1)	保留指数 RI		鉴定依据 Identification
序号 No.	挥发性成分 Volatile	分子式 Formula	分子量 Mass	保留时间 Retention time (min)	含量 Content (μg·kg^-1)	Cal.	Ref.	鉴定依据 Identification
31	3-甲基-十五烷 3-Methyl-pentadecane	C₁₆H₃₄	226	40.65	0.12	1573	1571	MS, RI
32	十六烷 Hexadecane	C₁₆H₃₄	226	41.11	0.36	1600	1600	MS, RI
33	2,6,10-三甲基-十五烷 2,6,10-Trimethyl-pentadecane	C₁₈H₃₈	254	41.84	0.17	1643	1649	MS, RI
酯类 Esters
34	乙酸乙酯 Ethyl acetate	C₄H₈O₂	88	2.95	0.32	659	634	MS
35	己酸乙酯 Ethyl hexanoate	C₈H₁₆O₂	144	18.14	0.11	1003	1001	MS, RI
36	乙酸叶醇酯 (Z)-3-Hexenyl acetate	C₈H₁₄O₂	142	18.63	0.25	1010	1007	MS, RI
37	乙酸己酯 Hexyl acetate	C₈H₁₆O₂	144	19.15	0.66	1017	1017	MS, RI
38	苯甲酸甲酯 Methyl benzoate	C₈H₈O₂	136	24.87	0.05	1101	1093	MS, RI
39	异丁酸叶醇酯 (Z)-3-Hexenyl isobutyrate	C₁₀H₁₈O₂	170	27.79	0.21	1138	1145	MS, RI
40	丁酸己酯 Hexyl butanoate	C₁₀H₂₀O₂	172	28.05	0.10	1145	1148	MS, RI
41	己酸异丁酯 Isobutyl hexanoate	C₁₀H₂₀O₂	172	28.16	0.07	1147	1148	MS, RI
42	乙酸苯甲酯 Benzyl acetate	C₉H₁₀O₂	150	28.69	0.14	1161	1161	MS, RI
43	苯甲酸乙酯 Ethyl benzoate	C₉H₁₀O₂	150	28.92	3.25	1167	1170	MS, RI
44	4-辛烯酸乙酯 Ethyl 4-octenoate	C₁₀H₁₈O₂	170	29.87	0.04	1190	1191	MS, RI
45	辛酸乙酯 Ethyl octanoate	C₁₀H₂₀O₂	172	30.22	0.20	1199	1201	MS, RI
46	乙酸辛酯 Octyl acetate	C₁₀H₂₀O₂	172	30.80	0.04	1214	1213	MS, RI
47	异戊酸叶醇酯 cis-3-Hexenyl isovalerate	C₁₁H₂₀O₂	184	31.56	0.42	1233	1235	MS, RI
48	异戊酸己酯 Hexyl 2-methylbutyrate	C₁₁H₂₂O₂	186	31.74	0.24	1237	1239	MS, RI
49	2-辛烯酸乙酯 Ethyl (E)-2-octenoate	C₁₀H₁₈O₂	170	32.12	0.04	1247	1246	MS, RI
50	己酸异戊酯 Isoamyl hexanoate	C₁₁H₂₂O₂	186	32.23	0.05	1250	1251	MS, RI
51	乙酸苯乙酯 Phenethyl acetate	C₁₀H₁₂O₂	164	32.47	1.16	1256	1256	MS, RI
52	辛酸丙酯 Propyl octanoate	C₁₁H₂₂O₂	186	33.96	0.05	1293	1292	MS, RI
53	壬酸乙酯 Ethyl nonanoate	C₁₁H₂₂O₂	186	34.15	0.05	1298	1298	MS, RI
54	乙酸壬酯 Nonyl acetate	C₁₁H₂₂O₂	186	34.73	0.08	1316	1314	MS, RI
55	乙酸橙花酯 Neryl Acetate	C₁₂H₂₀O₂	196	36.95	0.03	1388	1372	MS, RI
56	(E)-己酸-2-己烯酯 (E)-2-Hexenyl hexanoate	C₁₂H₂₂O₂	198	37.10	0.14	1393	1391	MS, RI
57	癸酸乙酯 Ethyl caprate	C₁₂H₂₄O₂	200	37.25	0.21	1398	1398	MS, RI
58	(Z)-庚酸-3-己烯酯 (Z)-3-Hexenyl heptanoate	C₁₃H₂₄O₂	212	39.08	0.13	1483	1489	MS, RI
59	庚酸丁酯 Butyl heptanoate	C₁₁H₂₂O₂	186	39.17	0.07	1488	1490	MS, RI
60	(Z)-3-辛酸己烯酯 (Z)-3-Hexenyl octanoate	C₁₄H₂₆O₂	226	40.80	0.78	1582	1588	MS, RI
61	辛酸己酯 Hexyl octanoate	C₁₄H₂₈O₂	228	40.86	0.54	1585	1582	MS, RI
62	月桂酸乙酯 Ethyl laurate	C₁₄H₂₈O₂	228	41.05	0.17	1596	1597	MS, RI
63	软脂酸乙酯 Ethyl palmitate	C₁₈H₃₆O₂	284	46.14	0.09	1900	1914	MS, RI

表1

表2

欧李果实挥发性成分香气强度与品质"

化合物 Compound	香气阈值 Odor threshold (μg·kg^-1)	香气强度值 OAVs	香气品质 Aroma quality^[19,20,21]	香气类型 Odor type^[21,22]	香气强度 Odor strength^[21]
苯甲醛 Benzaldehyde	350^[23]	<0.001	苦杏仁味 Bitter almond-like	芳香型 Aromatic	高 High
邻二甲苯 o-Xylene			天竺葵香气 Geranium-like	芳香型 Aromatic	中 Medium
苯甲酸甲酯 Methyl benzoate	0.52^[24]	0.096	杏仁味 Almond-like	酚香型 Phenolic	高 High
己酸乙酯 Ethyl hexanoate	0.01^[25]	10.873	凤梨果香 Pineapple-like	果香型 Fruity	高 High
异丁酸叶醇酯 (Z)-3-Hexenyl isobutyrate			苹果香 Apple-like	果香型 Fruity	高 High
乙酸己酯 Hexyl acetate	2^[26]	0.33	梨子香 Pear-like	果香型 Fruity	中 Medium
2-壬酮 2-Nonanone	5^[26]	0.01	似草香、泥土气息 Weedy and earthy-like	果香型 Fruity	中 Medium
4-辛烯酸乙酯 Ethyl 4-octenoate			柑橘气味 Citrus-like	果香型 Fruity	中 Medium
2-辛烯酸乙酯 Ethyl (E)-2-octenoate			凤梨果香 Pineapple-like	果香型 Fruity	中 Medium
己酸异戊酯 Isoamyl hexanoate			苹果香 Apple-like	果香型 Fruity	中 Medium
2-乙基-己醇 2-Ethyl-hexanol			香草味 Herbaceou-like	花香型 Floral	中 Medium
β-芳樟醇 β-Linalool	0.5^[27]	0.476	铃兰香气 Keiskei-like	花香型 Floral	中 Medium
苯乙醇 Phenylethyl alcohol	750^[28]	<0.001	玫瑰花香 Rose-like	花香型 Floral	中 Medium
乙酸苯甲酯 Benzyl acetate			茉莉花香 Jasmin fresh	花香型 Floral	中 Medium
壬醇 Nonanol	50^[26]	0.006	玫瑰花、甜橙气息 Rose-and orange-like	花香型 Floral	中 Medium
乙酸辛酯 Octyl acetate	12^[29]	0.003	花香、草香 Floral and herbal-like	花香型 Floral	中 Medium
乙酸苯乙酯 Phenethyl acetate	0.25^[30]	4.629	甜蜜香味 Sweet honey-like	花香型 Floral	中 Medium
2-甲基萘 2-Methylnaphthalene			甜香 Sweety	花香型 Floral	中 Medium
乙酸橙花酯 Neryl Acetate			甜香 Sweet floral	花香型 Floral	中 Medium
乙酸乙酯 Ethyl acetate	5^[17]	0.064	略带水果的酒香气味 Slightly fruity and winey-like	醚香型 Ethereal	高 High
α-法呢烯 α-Farnesene			草香 Herbal-like	木香型 Woody	中 Medium
(Z)-3-己烯-1-醇 (Z)-3-Hexen-1-ol			香草味 Herbaceous-like	青香型 Green	高 High
乙酸叶醇酯 (Z)-3-Hexenyl acetate			香蕉味 Banana-like	青香型 Green	高 High
丁酸己酯 Hexyl butanoate	250^[29]	<0.001	蔬菜气息 Vegetables-like	青香型 Green	中 Medium
己酸异丁酯 Isobutyl hexanoate			可可香气 Cocoa-like	青香型 Green	中 Medium
苯甲酸乙酯 Ethyl benzoate	60^[26]	0.054	焦油味 Tar-like	青香型 Green	中 Medium
异戊酸叶醇酯 cis-3-Hexenyl isovalerate			青苹果气息 Green apple-like	青香型 Green	中 Medium
异戊酸己酯 Hexyl 2-methylbutyrate			生果实味 Raw fruit-like	青香型 Green	中 Medium
(E)-己酸-2-己烯酯 (E)-2-Hexenyl hexanoate			青香 Green	青香型 Green	中 Medium
庚酸丁酯 Butyl heptanoate			甘草味 Licorice-like	青香型 Green	中 Medium
(Z)-3-辛酸己烯酯 (Z)-3-Hexenyl octanoate			弱的青香 Faint Green-like	青香型 Green	中 Medium
辛酸己酯 Hexyl octanoate			新鲜蔬菜气息 Fresh Vegetables-like	青香型 Green	中 Medium
壬醛 Nonanal	1^[24]	0.156	柑橘香 Citrus-like	醛香型 Aldehydic	高 High
萘 Naphthalene	21^[31]	0.001	干树脂气味 Dry resinous	辛香型 Spicy	高 High
辛酸丙酯 Propyl octanoate			椰子气味 Coconut-like	椰子香型 Coconut	中 Medium
软脂酸乙酯 Ethyl palmitate	2000^[32]	<0.001	微弱蜡香 Soft waxy-like	脂蜡香型 Waxy	低 Low
辛醇 Octanol	110^[28]	<0.001	脂蜡香气、柑橘气息 Waxy and orange-like	脂蜡香型 Waxy	中 Medium
辛酸乙酯 Ethyl octanoate	5^[33]	0.04	白兰地香气 Brandy-like	脂蜡香型 Waxy	中 Medium
壬酸乙酯 Ethyl nonanoate			略带脂肪-油脂气味 Slightly fatty-oily-like	脂蜡香型 Waxy	中 Medium
乙酸壬酯 Nonyl acetate			果香和栀子花香气 Fruity and gardenia-like	脂蜡香型 Waxy	中 Medium
癸酸乙酯 Ethyl caprate	23^[32]	<0.001	油脂、酒香气味 Oily and winey-like	脂蜡香型 Waxy	中 Medium
月桂酸乙酯 Ethyl laurate			花生香气 Peanut-like	脂蜡香型 Waxy	中 Medium

表2

图7

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