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山矾Symplocos sumuntia又名山桂花,是山矾科Symplocaceae山矾属Symplocos常绿灌木或小乔木,分布于长江以南各省区[1]。山矾科仅山矾属1属,该属多种植物有清热解毒、理气止痛、止血生肌、化痰止咳等重要的药用价值[2]。由于山矾枝繁叶茂,四季常绿,开花繁密并具有强烈的芳香,又可作为一种极具潜力的观赏植物进行开发利用[3]。目前,关于山矾花香方面的研究报道较少。罗心毅等[4]通过水蒸汽蒸馏法获得山矾精油,共鉴定出68种化学成分;余爱农等[5]利用60H型硅胶吸收山矾花香,再通过溶剂洗脱后,进行气相-质谱联用技术(GC-MS)分析并鉴定出22个挥发性化学成分。由于水蒸汽加热过程中会使一些香味物质变性损失,而用硅胶吸附香气所需时间过长,容易引起花瓣褐化,并且温度升高和缺乏气体交换会影响其正常生理进程,进而影响挥发物的释放[6],所以以上2种方法可能会造成部分花香成分的损失或变化。植物花香成分及释放量在很大程度上受花朵发育程度的影响[7-8],现已发现玫瑰Rosa rugosa,百合Lilium brownii,金鱼草Antirrhinum majus,枇杷Eriobotrya japonica,文心兰Oncidium‘Sharry Baby’,桂花Osmanthus fragrans等多种植物的花香随着开花进程表现出不同的变化规律,基本呈现为半开期和盛开期花香物质种类和释放量明显增加[9-14]。固相微萃取技术作为一种简便且有效的花香采集方法,集采样、浓缩、萃取为一体,通过萃取头表面涂层吸附挥发性物质,可以在花香采样后立即测定,避免了鲜花离体时间过长导致花香成分变化的问题,现已应用于多种植物花香的采样[15]。本研究采用顶空固相微萃取(HS-SPME)结合GC-MS分析山矾不同开花时期花香成分和相对含量的变化,探索山矾鲜花自然环境中真实的香气组成及释放规律,旨在为山矾野生植物资源及其花香的开发利用提供参考。
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试验得到山矾不同开花时期GC-MS总离子流色谱图(图 2)。通过对各组分图谱分析及资料核实,分别从蕾期、半开期、盛开期检测出35,39,42种挥发物,主要包括醇类、酮类、酯类、醛类、芳香族类和酸类六大类(表 1)。
表 1 山矾花不同发育时期的主要挥发物成分及其相对含量
Table 1. Main volatiles compositions and relative contents at different flowering stages of Symplocos sumuntia
序号 t/min 化合物 相对含量/% 蕾期 半开期 盛开期 1 10.605 桉油醇 eucalyptol 3.86±1.46 c 11.9±1.54 b 18.17±1.90 a 2 12.844 乙酸己酯 hexyl acetate 0.80±0.00 - 0.59±0.00 3 14.069 乙酸-4-己烯-1-醇酯 4-Dexen-1-ol, acetate 4.89±0.99 0.49±0.18 1.38±0.85 4 14.600 6-甲基-5-庚烯-2-酮 6-methyl-5-hepten-2-one 0.28±0.00 - - 5 15.121 正己醇 1-hexanol 0.24±0.07 - - 6 15.479 十二甲基环六桂氧烷 cyclohexasiloxane,dodecametDyl- 0.24±0.00 - - 7 15.936 叶醇 leaf alcohol 0.73±0.02 - 0.16±0.00 8 16.406 壬醛 nonanal 0.38±0.07 - - 9 17.66 顺式-氧化芳樟醇 cis-linalool oxide 1.52±0.15 a 0.61±0.05 b 0.80±0.12 b 10 18.195 乙二醇丁醚醋酸酯 2-butoxyethyl acetate 0.20±0.00 - - 11 18.431 反式-氧化芳樟醇 trans-linalool oxide 12.68±0.72 a 5.74±0.36 b 6.55±0.83 b 12 19.415 癸醛 decanal 0.68±0.14 - - 13 19.424 苯甲醛 benzaldehyde - 0.38±0.12 0.17±0.01 14 20.244 丁香醛 J Lilac aldehyde A - 0.48±0.00 1.69±0.16 15 20.595 芳樟醇 linalool 20.19±1.18 a 2.10±0.29 c 5.49±0.99 b 16 20.810 丁香醛 L lilac aldehyde L - 0.54±0.00 2.05±0.17 17 21.397 丁香醛 C lilac aldehyde C - 0.45±0.00 1.54±0.12 18 21.922 (-)-4-萜品醇(-)-terpinen-4-ol - 0.16±0.04 0.18±0.04 19 22.128 脱氢芳樟醇 hotrienol 1.32±0.12 a 0.52±0.29 b 0.46±0.08 c 20 22.497 苯乙醛 benzeneacetaldehyde - 0.12±0.00 0.40±0.05 21 22.962 二甲基桂院双醇 silanediol,dimethyl- 1.10±0.32 0.51±0.13 0.79±0.06 22 24.225 α-松油醇 α-terpineol 0.39±0.05 0.24±0.04 0.36±0.05 23 24.755 紫丁香醇 LlilacalcoholL - 0.17±0.00 2.13±0.16 24 25.77 双花醇 2H-pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl- 19.45±1.31a 10.05±0.77 b 13.09±0.85 b 25 26.295 紫丁香醇 ClilacalcoholC - 0.24±0.04 0.66±0.06 26 27.155 双丙甘醇 2-propanol,1,1’-oxybis- 0.58±0.11 0.46±0.02 - 27 27.221 紫丁香醇 AlilacalcoholA - - 0.75±0.06 28 27.46 二氢-β-紫罗兰酮2H-β-ionone 0.33±0.06 b 0.72±0.11a 0.32±0.03 b 29 27.81 反式-β-紫罗兰酮(E)-β-ionone 0.12±0.00 2.40±0.31 1.52±0.21 30 28.037 香叶基丙酮(E)-Geranylacetone 0.62±0.11 - - 31 28.053 苄醇 benzyl alcohol - 0.22±0.00 0.23±0.02 32 28.257 2-(2-轻基丙氧基)-1-丙醇1-propanol,2-(2-hydroxypropoxy)- 0.49±0.06 a 0.29±0.03 b 0.16±0.01b 33 28.841 苯乙醇 phenylethyl alcohol 0.32±0.03 b 0.40±0.15 b 1.98±0.18 a 34 29.066 苯甲腊 benzyl nitrile 1.26±0.21a 0.41±0.06 b 0.42±0.02 b 35 29.734 β-紫罗兰酮 β-ionone 0.60±0.06 c 33.38±1.76 a 19.14±3.12 b 36 30.046 二氢-β-紫罗兰酮 2H-β-ionone 0.17±0.02 0.31±0.00 0.18±0.04 37 30.546 1-十三醇 n-tridecan-1-ol 0.27±0.01 0.23±0.05 0.17±0.01 38 30.786 4-(2,2,6-三甲基-7-氧杂二环[4.1.0]-1-庚基)-3-丁烯-2-酮 3-buten-2-one, (2,2,6-trimethyl-7-oxabicyclo [ 4.1.0 ] hept-1 -yl) - 0.28±0.07 - 39 31.301 檀花醚 2H-pyran,3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)- - - 0.15±0.02 40 31.879 3,4,5-三甲氧基甲苯 3,4,5-trimethoxy toluene 7.79±0.38 b 15.29±0.37 a 3.99±0.64 c 41 32.154 邻甲氧基苯甲酸甲酯 benzoic acid, 2-methoxy-, methyl ester 0.51±0.03 a 0.40±0.09ab 0.22±0.04 b 42 33.712 3-甲基-庚-1,6-二亚乙基三胺-3-醇 3-methyl-hepta-1,6-dien-3-ol - 0.21±0.06 1.1±0.12 43 34.322 1,2,4-三甲氧基苯 1,2,4-Trimethoxybenzene 0.31±0.05 0.43±0.00 2.42±0.21 44 36.066 棕榈酸甲酯 hexadecanoic acid, methyl ester 0.28±0.00 0.32±0.00 0.37±0.17 45 37.52 1,2,3-三甲氧基苯 1,2,3-trimethoxybenzene - - 0.36±0.05 46 37.996 邻苯二甲酸二乙酯 diethyl phthalate 0.16±0.00 0.17±0.00 0.10±0.00 47 39.052 吲哚 indole - 0.17±0.00 0.14±0.02 48 40.149 反油酸甲酯 methyl elaidate 4.37±0.70 3.38±0.87 3.92±0.71 49 40.886 亚油酸乙酯 linoleic acid ethyl ester 0.58±0.14 0.26±0.06 0.33±0.05 50 43.134 反式-4-(反-4-戊基)环己基)-1-环己甲酸4-氟苯酯[1,1’-bicy-clohexyl]-4-carboxylic acid, 4’-pentyl-, 4-fluorophenyl ester - 0.27 % 0.02 1.71±0.00 51 47.357 油酸 oleic acid 0.12±0.00 0.69±0.00 0.41±0.20 说明:a,b,c代表多重比较SNK检验在P≤0.05显著性水平下的差异显著;“-”该成分未检测出。 -
从图 3可以看出:醇类和酮类是各时期相对含量较高的化合物。对各类物质差异性分析可知,醇类在开花过程中呈现高-低-高的变化趋势;酮类和芳香族类在半开期相对含量达到最高,然后逐渐降低;醛类的相对含量在盛花期达到最高;酯类和酸类在各个开花阶段的挥发量并无显著差异。
图 3 山矾花不同发育状态的主要挥发物种类比较
Figure 3. Comparison of main volatile categories from the flowers of Symplocos sumuntia at different flowering stages
蕾期山矾花的挥发性成分中,醇类的相对含量最高,占63.95%,主要成分包括芳樟醇(20.19%)、双花醇(19.45%),反式-氧化芳樟醇(12.68%),桉油醇(3.86%)等;酯类化合物相对含量占10.68%,主要有乙酸-4-己烯-1-醇酯(4.89%),反油酸甲酯(4.37%)等;芳香类化合物相对含量占9.36%,最高的是3,4,5-三甲氧基甲苯(7.79%)(表 1)。
半开期山矾花的挥发性成分中,以酮类和醇类化合物为主,相对含量分别占36.88%和34.06%,主要包括β-紫罗兰酮(33.38%),反式-β-紫罗兰酮(2.40%),双花醇(10.05%),桉油醇(11.90%),反式-氧化芳樟醇(5.74%),芳樟醇(2.10%)等;芳香族化合物的相对含量占15.90%,其中相对含量最高的是3,4,5-三甲氧基甲苯(15.29%);酯类化合物(4.70%)中相对含量最高的是反油酸甲酯(3.38%)。
盛开期山矾花的挥发性成分中,以醇类化合物为主,相对含量占55.29%,主要成分包括桉油醇(18.17%),双花醇(13.09%),反式-氧化芳樟醇(6.55%),芳樟醇(5.49%),紫丁香醇的不同异构体(3.54%)等;酮类化合物相对含量占21.16%,主要成分是β-紫罗兰酮(19.14%),反式-β-紫罗兰酮(1.52%);芳香族化合物相对含量占7.43%,主要包括3,4,5-三甲氧基甲苯(3.99%),1,2,4-三甲氧基苯(2.42%)等;酯类化合物的相对含量占6.44%,主要包括反油酸甲酯(3.92%)和反式-4-(反-4-戊基-环己基)-1-环己甲酸4-氟苯酯(1.71%)等;醛类化合物的相对含量占5.86%,以丁香醛的不同异构体(5.28%)为主。
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在所检测的挥发性物质中,相对含量较高的挥发性物质包括β-紫罗兰酮、桉油醇、双花醇、反式-氧化芳樟醇、芳樟醇、3,4,5-三甲氧基甲苯,这些挥发物构成了山矾的主要呈香成分,且各物质在不同开花时期呈动态变化。β-紫罗兰酮的相对含量在蕾期很低(0.60%),到半开期迅速上升,成为相对含量最高的物质(33.38%),在盛开期稍有所降低(19.14%);桉油醇的相对含量在山矾开花进程中呈现不断上升的趋势;双花醇、反式-氧化芳樟醇以及芳樟醇均在蕾期有较高的相对含量,到半开期和盛开期明显降低;3,4,5-三甲氧基甲苯的相对含量从蕾期到盛开期表现为先上升后降低的趋势,半开期分别是蕾期和盛开期的近2倍和近5倍。
Flower scent component changes during the flowering process in Symplocos sumuntia
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摘要: 用顶空固相微萃取(HS-SPME)结合气相-质谱联用技术(GC-MS)对蕾期、半开期、盛开期山矾Symplocos sumuntia花的挥发性物质进行鉴定。结果表明:从3个花期的山矾花分别鉴定出35,39,42种挥发物,属于醇类、酮类、酯类、醛类、芳香族类和酸类化合物,各时期最主要的花香物质是醇类和酮类。蕾期相对含量高的物质是芳樟醇(20.19%),双花醇(19.45%),反式-氧化芳樟醇(12.68%);半开期的是β-紫罗兰酮(33.38%),3,4,5-三甲氧基甲苯(15.29%),桉油醇(11.90%);盛开期的是β-紫罗兰酮(19.14%),桉油醇(18.17%),双花醇(13.09%)。因此,山矾花的主要香气成分为β-紫罗兰酮、桉油醇、双花醇、反式-氧化芳樟醇、芳樟醇和3,4,5-三甲氧基甲苯,其中,β-紫罗兰酮对半开期花香贡献最大,而盛开期的香气是由多种物质共同贡献。结果为山矾花香利用及昆虫传粉研究提供了科学依据。图3表1参39Abstract: In order to provide a scientific basis for the utilization of floral aroma and the exploration of insect pollination, volatile compounds from the flowers of Symplocos sumuntia at the bud stage, middle opening stage, and full opening stage were analyzed by Headspace Solid Phase Micro-extraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS). The results showed that 35, 39, and 42 kinds of volatile compounds were identified from the flowers at the bud, middle opening, and full opening stages, respectively. These volatile compounds mainly belonged to alcohols, ketones, esters, aldehydes, aromatics, and acids with the major categories being alcohols and aldehydes. The relative content of linalool (20.2%), trans-linalool oxide (12.7%), and 2H-pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl (19.5%) were higher at the bud stage. β-ionone (33.4%), eucalyptol (11.9%), and 3,4,5-trimethoxy toluene (15.3%) showed the highest released relative content at the middle opening stage. At the full opening stage, β-ionone (19.1%), eucalyptol (18.2%), and 2H-pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl (13.19%) were the dominate components. Therefore, the main aromatic components from the flowers of S. sumuntia were β-ionone, eucalyptol, 2H-pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, trans-linalool oxide, linalool, and 3,4,5-trimethoxy toluene. Also, for the scent of flowers, at the middle opening stage β-ionone made the dominate contribution; whereas, at the full opening stage various compounds dominated. [Ch, 3 fig. 1 tab. 39 ref.]
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Key words:
- botany /
- Symplocos sumuntia /
- scent components /
- SPME /
- GC-MS
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表 1 山矾花不同发育时期的主要挥发物成分及其相对含量
Table 1. Main volatiles compositions and relative contents at different flowering stages of Symplocos sumuntia
序号 t/min 化合物 相对含量/% 蕾期 半开期 盛开期 1 10.605 桉油醇 eucalyptol 3.86±1.46 c 11.9±1.54 b 18.17±1.90 a 2 12.844 乙酸己酯 hexyl acetate 0.80±0.00 - 0.59±0.00 3 14.069 乙酸-4-己烯-1-醇酯 4-Dexen-1-ol, acetate 4.89±0.99 0.49±0.18 1.38±0.85 4 14.600 6-甲基-5-庚烯-2-酮 6-methyl-5-hepten-2-one 0.28±0.00 - - 5 15.121 正己醇 1-hexanol 0.24±0.07 - - 6 15.479 十二甲基环六桂氧烷 cyclohexasiloxane,dodecametDyl- 0.24±0.00 - - 7 15.936 叶醇 leaf alcohol 0.73±0.02 - 0.16±0.00 8 16.406 壬醛 nonanal 0.38±0.07 - - 9 17.66 顺式-氧化芳樟醇 cis-linalool oxide 1.52±0.15 a 0.61±0.05 b 0.80±0.12 b 10 18.195 乙二醇丁醚醋酸酯 2-butoxyethyl acetate 0.20±0.00 - - 11 18.431 反式-氧化芳樟醇 trans-linalool oxide 12.68±0.72 a 5.74±0.36 b 6.55±0.83 b 12 19.415 癸醛 decanal 0.68±0.14 - - 13 19.424 苯甲醛 benzaldehyde - 0.38±0.12 0.17±0.01 14 20.244 丁香醛 J Lilac aldehyde A - 0.48±0.00 1.69±0.16 15 20.595 芳樟醇 linalool 20.19±1.18 a 2.10±0.29 c 5.49±0.99 b 16 20.810 丁香醛 L lilac aldehyde L - 0.54±0.00 2.05±0.17 17 21.397 丁香醛 C lilac aldehyde C - 0.45±0.00 1.54±0.12 18 21.922 (-)-4-萜品醇(-)-terpinen-4-ol - 0.16±0.04 0.18±0.04 19 22.128 脱氢芳樟醇 hotrienol 1.32±0.12 a 0.52±0.29 b 0.46±0.08 c 20 22.497 苯乙醛 benzeneacetaldehyde - 0.12±0.00 0.40±0.05 21 22.962 二甲基桂院双醇 silanediol,dimethyl- 1.10±0.32 0.51±0.13 0.79±0.06 22 24.225 α-松油醇 α-terpineol 0.39±0.05 0.24±0.04 0.36±0.05 23 24.755 紫丁香醇 LlilacalcoholL - 0.17±0.00 2.13±0.16 24 25.77 双花醇 2H-pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl- 19.45±1.31a 10.05±0.77 b 13.09±0.85 b 25 26.295 紫丁香醇 ClilacalcoholC - 0.24±0.04 0.66±0.06 26 27.155 双丙甘醇 2-propanol,1,1’-oxybis- 0.58±0.11 0.46±0.02 - 27 27.221 紫丁香醇 AlilacalcoholA - - 0.75±0.06 28 27.46 二氢-β-紫罗兰酮2H-β-ionone 0.33±0.06 b 0.72±0.11a 0.32±0.03 b 29 27.81 反式-β-紫罗兰酮(E)-β-ionone 0.12±0.00 2.40±0.31 1.52±0.21 30 28.037 香叶基丙酮(E)-Geranylacetone 0.62±0.11 - - 31 28.053 苄醇 benzyl alcohol - 0.22±0.00 0.23±0.02 32 28.257 2-(2-轻基丙氧基)-1-丙醇1-propanol,2-(2-hydroxypropoxy)- 0.49±0.06 a 0.29±0.03 b 0.16±0.01b 33 28.841 苯乙醇 phenylethyl alcohol 0.32±0.03 b 0.40±0.15 b 1.98±0.18 a 34 29.066 苯甲腊 benzyl nitrile 1.26±0.21a 0.41±0.06 b 0.42±0.02 b 35 29.734 β-紫罗兰酮 β-ionone 0.60±0.06 c 33.38±1.76 a 19.14±3.12 b 36 30.046 二氢-β-紫罗兰酮 2H-β-ionone 0.17±0.02 0.31±0.00 0.18±0.04 37 30.546 1-十三醇 n-tridecan-1-ol 0.27±0.01 0.23±0.05 0.17±0.01 38 30.786 4-(2,2,6-三甲基-7-氧杂二环[4.1.0]-1-庚基)-3-丁烯-2-酮 3-buten-2-one, (2,2,6-trimethyl-7-oxabicyclo [ 4.1.0 ] hept-1 -yl) - 0.28±0.07 - 39 31.301 檀花醚 2H-pyran,3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)- - - 0.15±0.02 40 31.879 3,4,5-三甲氧基甲苯 3,4,5-trimethoxy toluene 7.79±0.38 b 15.29±0.37 a 3.99±0.64 c 41 32.154 邻甲氧基苯甲酸甲酯 benzoic acid, 2-methoxy-, methyl ester 0.51±0.03 a 0.40±0.09ab 0.22±0.04 b 42 33.712 3-甲基-庚-1,6-二亚乙基三胺-3-醇 3-methyl-hepta-1,6-dien-3-ol - 0.21±0.06 1.1±0.12 43 34.322 1,2,4-三甲氧基苯 1,2,4-Trimethoxybenzene 0.31±0.05 0.43±0.00 2.42±0.21 44 36.066 棕榈酸甲酯 hexadecanoic acid, methyl ester 0.28±0.00 0.32±0.00 0.37±0.17 45 37.52 1,2,3-三甲氧基苯 1,2,3-trimethoxybenzene - - 0.36±0.05 46 37.996 邻苯二甲酸二乙酯 diethyl phthalate 0.16±0.00 0.17±0.00 0.10±0.00 47 39.052 吲哚 indole - 0.17±0.00 0.14±0.02 48 40.149 反油酸甲酯 methyl elaidate 4.37±0.70 3.38±0.87 3.92±0.71 49 40.886 亚油酸乙酯 linoleic acid ethyl ester 0.58±0.14 0.26±0.06 0.33±0.05 50 43.134 反式-4-(反-4-戊基)环己基)-1-环己甲酸4-氟苯酯[1,1’-bicy-clohexyl]-4-carboxylic acid, 4’-pentyl-, 4-fluorophenyl ester - 0.27 % 0.02 1.71±0.00 51 47.357 油酸 oleic acid 0.12±0.00 0.69±0.00 0.41±0.20 说明:a,b,c代表多重比较SNK检验在P≤0.05显著性水平下的差异显著;“-”该成分未检测出。 -
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