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不同品种金银花精油组分对比研究

刘亚 吕兆林 邹小琳 任璇 胡建忠

刘亚, 吕兆林, 邹小琳, 任璇, 胡建忠. 不同品种金银花精油组分对比研究[J]. 北京林业大学学报, 2017, 39(2): 72-81. doi: 10.13332/j.1000-1522.20160183
引用本文: 刘亚, 吕兆林, 邹小琳, 任璇, 胡建忠. 不同品种金银花精油组分对比研究[J]. 北京林业大学学报, 2017, 39(2): 72-81. doi: 10.13332/j.1000-1522.20160183
LIU Ya, LV Zhao-lin, ZOU Xiao-lin, REN Xuan, HU Jian-zhong. Comparation in essential oil components of different varieties of honeysuckle[J]. Journal of Beijing Forestry University, 2017, 39(2): 72-81. doi: 10.13332/j.1000-1522.20160183
Citation: LIU Ya, LV Zhao-lin, ZOU Xiao-lin, REN Xuan, HU Jian-zhong. Comparation in essential oil components of different varieties of honeysuckle[J]. Journal of Beijing Forestry University, 2017, 39(2): 72-81. doi: 10.13332/j.1000-1522.20160183

不同品种金银花精油组分对比研究

doi: 10.13332/j.1000-1522.20160183
基金项目: 

“十二五”国家科技支撑计划项目 2015BAD16B00

详细信息
    作者简介:

    刘亚。主要研究方向:天然产物的分离与加工利用。Email:1643854627@qq.com   地址:100083 北京市海淀区清华东路35号北京林业大学生物科学与技术学院

    责任作者:

    吕兆林,博士,副教授。主要研究方向:天然产物的分离与加工利用。Email: zhaolinlv@bjfu.edu.cn  地址: 100083 北京市海淀区北京林业大学分析检测中心

  • 中图分类号: S718.43;S789.9

Comparation in essential oil components of different varieties of honeysuckle

  • 摘要: 研究同一产地3个不同品种金银花精油的成分,并探索其化合物组成的异同。本实验以3种典型的忍冬科金银花(菰腺忍冬、灰毡毛忍冬、黄褐毛忍冬)为实验材料,采用提取率较高的精油提取装置提取其中的精油,并用气质联用仪(GC-MS)对其进行组分分析。3个不同品种的金银花共检出125种挥发性化合物;通过NIST11标准质谱库检索及人工图谱解析,确定了118种化合物结构。灰毡毛忍冬精油组成以烃类、酯类、醇类为主,其中所占比重最大为醇类,高达71.17%(C10的醇类相对含量为68.93%);化合物种类最多的为C5~C10(27种),占78.28%。菰腺忍冬精油以烃类、醇类为主,其中所占的比重最高为醇类,高达86.3%(C10的醇类相对含量为78.66%);化合物种类最多的为C5~C10(22种),相对百分含量为84.84%;并且没有羧酸类化合物。黄褐毛忍冬精油以酮类、酯类、醇类、醛类为主,其中所占的比例最大的为酯类,高达57.92%(C16~C20的酯类的相对含量为55.61%);种类最多为C5~C10(41种),相对百分含量为34.28%;但是C16~C20的含量最大,为59.33%(种类为15种)。研究表明:金银花种类不同,其精油组成成分在化合物种类、个数及相对含量方面差异很大,通过此次分析为金银花类别的鉴定及其精油的药用价值和香味来源的分析提供数据基础。

     

  • 图  1  菰腺忍冬精油总离子流

    Figure  1.  Total ion chromatogram of Lonicera hypoglauca essential oil

    图  2  灰毡毛忍冬精油总离子流

    Figure  2.  Total ion chromatogram of Lonicera macranthoides essential oil

    图  3  黄褐毛忍冬精油总离子流

    Figure  3.  Total ion chromatogram of Lonicera fulvotomentosa essential oil

    图  4  3种金银花醇类和酯类相对含量百分含量堆积图

    Figure  4.  Percentage stacked chart of alcohols and ester relative content for three kinds of honeysuckle

    表  1  3种不同金银花精油成分的组成及含量

    Table  1.   Components and relative content of essential oil for three kinds of honeysuckle

    序号No. 出峰时间Peak time/min 化合物名称Compound name 分子式Formula 分子量Formula weight 相对百分含量Relative percentage content/%
    菰腺忍冬Lonicera hypoglauca 灰毡毛忍冬Lonicera macranthoides 黄褐毛忍冬Lonicera fulvotomentosa
    1 3.828 环氧环己烷Cyclohexene oxide C6H10O 98 0.1
    2 3.858 (Z)-4-己烯-1-醇(Z)-Hex-4-en-1-ol C6H12O 100 0.12
    3 4.112 甲酸己酯Hexyl formate C7H14O2 130 0.08
    4 4.662 苯乙烯Styrene C8H8 104 0.11 0.12 0.12
    5 4.839 2-庚醇2-Hydroxyheptane C7H16O 116 0.08
    6 6.481 5-甲基呋喃醛5-Methyl furfural C6H6O2 110 0.13
    7 6.545 苯甲醛Benzaldehyde C7H6O 106 0.1 0.27 0.12
    8 6.832 5-甲基-2-(1-甲基乙基)-2-己烯醛2-Isopropyl-5-methyl-2-hexenal C10H18O 154 0.34
    9 6.888 己酸Hexanoic acid C6H12O2 116 0.27
    10 7.114 1-辛烯-3-醇1-Octen-3-ol C8H16O 128 0.18 0.23
    11 7.470 月桂烯Myrcene C10H16 136 0.28
    12 8.177 (E, E)-2, 4-庚二烯醛(E, E)-2, 4-Heptadienal C7H10O 110 0.57
    13 8.194 未知Unknown 未知Unknown 未知Unknown 0.09
    14 8.440 α-萜品烯α-Terpinene C10H16 136 0.47
    15 8.707 间异丙基甲苯m-Cymene C10H14 134 0.06
    16 8.884 右旋萜二烯D-Limonene C10H16 136 0.3 0.34
    17 9.141 2-蒎烯2-Pinene C10H16 136 0.23
    18 9.348 苯乙醛Phenylacetaldehyde C8H8O 120 1.12 0.89
    19 9.536 (Z)-3, 7-二甲基-1, 3, 6-十八烷三烯(Z)- 3, 7-Dimethyl-1, 3, 6-octatriene C10H16 136 1.73 0.46
    20 9.796 顺式-3-辛烯醇(Z)-3-Octen-1-ol C8H16O 128 0.07
    21 9.991 萜品烯Terpinene C10H16 136 1.09
    22 10.371 邻甲氧基苯酚o-Methoxyphenol C7H8O2 124 0.06
    23 10.455 未知Unknown 未知Unknown 未知Unknown 0.91
    24 10.456 1-辛醇1-Octanol顺-α, α-5-三甲基-5-乙烯基四氢化呋喃- C8H18O 130 0.8
    25 11.083 2-甲醇cis-5-Ethenyltetrahydro-.alpha., .alpha.-5-trimethyl-2-furanmethanol C10H18O2 170 1.09
    26 11.338 烯丙基正戊基甲醇1-Nonen-4-ol C9H18O 142 0.35
    27 11.667 芳樟醇Linalool C10H18O 154 48.45 43.36 4.58
    28 11.738 2-壬醇2-Nonanol C9H20O 144 0.86
    29 11.785 3, 7-二甲基辛-1, 5, 7-三烯-3-醇(5E)-3, 7-Dimethylocta-1, 5, 7-trien-3-ol C10H16O 152 1.6
    30 11.836 壬醛Pelargonic aldehyde C9H18O 142 0.7
    31 12.060 苯乙醇Phenethyl alcohol1-甲基-4-(1-甲基乙基)-2-环己烯-1-醇 C8H10O 122 1.55
    32 12.657 1-methyl-4-(1-methylethyl)-2-cyclohexen-1-ol C10H18O 154 0.24
    33 13.354 未知Unknown 未知Unknown 未知Unknown 0.03
    34 13.850 反, 顺-2, 6-壬二烯醛(2E, 6Z)-Nona-2, 6-dien-1-al C9H14O 138 0.16
    35 13.911 顺-3-壬烯-1-醇cis-3-Nonen-1-ol C9H18O 142 0.14
    36 14.174 反式-2-壬烯醛(E)-Non-2-enal 2, 2, 6-三甲基-6-乙烯基四氢-2H-呋喃-3- C9H16O 140 0.31 0.3
    37 14.602 醇2, 2, 6-TriMethyl-6-vinyltetrahydro-2H-pyran-3-ol C10H18O2 170 0.07 0.55 0.48
    38 14.732 1-壬醇1-Nonanol C9H20O 144 0.7
    39 15.057 (-)-4-萜品醇(-)-4-Terpineol C10H18O 154 3.48 0.09
    40 15.345 (R)-氧化柠檬烯(R)-Limonene oxide C10H16O 152 0.08
    41 15.516 2-羟基-4-甲基苯甲醛2-Hydroxy-4-methyl-benzaldehyd C8H8O2 136 0.21
    42 15.693 alpha-松油醇alpha-Terpineol C10H18O 154 11.3 10.51 0.91
    43 16.241 癸醛Capraldehyde C10H20O 156 0.16
    44 16.788 玫瑰醚Rose oxide C10H18O 154 2.93
    45 16.942 对伞花烃p-Cymene C10H14 134 0.14
    46 17.023 橙花醇Nerol C10H18O 154 2.74 2.64 0.43
    47 17.150 (R)-(+)-β-香茅醇(R)-(+)-beta geraniol C10H20O 156 0.53
    48 17.252 异香叶醇iso-Geraniol C10H18O 154 0.39
    49 17.592 (Z)-3, 7-二甲基-2, 6-辛二烯醛Geranial C10H16O 152 0.41
    50 18.183 香叶醇Geraniol C10H18O 154 10.78 10.41 9.63
    51 18.457 未知Unknown 未知Unknown 未知Unknown 0.05
    52 18.475 1, 10-癸二醇1, 10-Decanediol C10H22O2 174 0.11
    53 18.657 环癸酮Cyclodecanone C10H18O 154 0.32
    54 18.904 (E)-3, 7-二甲基-2, 6-辛二烯醛, (E)-3, 7-Dimethyl-2, 6-octadienal C10H16O 152 1.17
    55 19.175 1-癸醇1-Hydroxydecane C10H22O 158 0.28 0.71
    56 19.669 茴香脑Anethole C10H12O 148 0.19 0.3 0.1
    57 19.670 (E, E)-2, 4-十二碳二烯醛(E, E)-2, 4-Dodecadienal C10H12O 148 0.57
    58 20.273 香芹酚Carvacrol C10H14O 150 0.28 0.13 0.42
    59 20.483 十四烷Tetradecane C14H30 198 0.03
    60 20.505 2-十四烷醇2-Tetradecanol C14H30O 214 0.56
    61 20.671 2-甲氧基-4-乙烯基苯酚2-Methoxy-4-ethenylphenol C9H10O2 150 0.63
    62 20.837 乙酸壬酯Nonyl acetate C11H22O2 186 0.25 0.24
    63 21.084 反式-2, 4-癸二烯醛trans, trans-2, 4-Decadienal C10H16O 152 0.3 0.72
    64 21.105 未知Unknown 未知Unknown 未知Unknown 0.09
    65 21.878 3-壬烯-2-酮3-Nonen-2-one C9H16O 140 0.23
    66 22.397 香叶酸Geranic acid C10H16O2 168 0.25
    67 22.485 丁香酚Eugenol C10H12O2 164 0.43
    68 22.754 丙位壬内酯γ-Nonylactone C9H16O2 156 0.16
    69 23.024 2-醛基苯甲酸甲酯Methyl 2-formylbenzoate C9H8O3 164 1.01
    70 23.087 3, 4-二甲氧基苯乙烯3, 4-Dimethoxy styrene C10H12O2 164 3.64
    71 23.657 大马士酮beta-Damascenone C13H18O 190 0.75 0.78 1.12
    72 24.230 茉莉酮Jasmone C11H16O 164 0.02
    73 24.601 甲基丁香酚Methyleugenol C11H14O2 178 0.38
    74 24.692 未知Unknown 未知Unknown 未知Unknown 0.24
    75 26.591 香叶基丙酮Geranyl acetone C13H22O 194 0.09 0.23 0.4
    76 26.945 1, 10-癸二醇1, 10-Decanediol C10H22O2 174 0.44
    77 27.042 2, 5-二叔丁基-1, 4-苯醌2, 5-Di-tert-butyl-1, 4-benzoquinone C14H20O2 220 0.13
    78 27.786 beta-紫罗兰酮beta-Ionone C13H20O 192 0.18
    79 28.828 2, 6-二叔丁基对甲酚2, 6-Di-tert-butyl-4-methylphenol C15H24O 220 0.2
    80 28.968 未知Unknown 未知Unknown 未知Unknown 1.78
    81 29.063 二环己基甲酮Dicyclohexyl ketone C13H22O 194 1.75
    82 29.747 月桂酸甲酯Methyl laurate 3, 7, 11-三甲基-1, 3, 6, 10-十二碳-四烯 C13H26O2 214 0.24
    83 29.760 (3E, 6E)-3, 7, 11-Trimethyl-1, 3, 6, 10-dodecatetraene C15H24 204 0.05
    84 29.869 桉油烯醇Spathulenol C15H24O 220 0.09
    85 31.133 乙酸羽扇醇酯Lup-20-en-3-ol, acetate C32H52O2 468 0.09
    86 31.142 3, 7, 11-三甲基-1, 6, 10-十二烷三烯-3-醇乙酸酯Nerolidol acetate C17H28O2 264 0.29
    87 31.153 反式-橙花叔醇Trans-Nerolidol C15H26O 222 2.26
    88 31.221 月桂酸Lauric acid C12H24O2 200 0.21
    89 31.906 (E)-2-甲基-2-丁烯酸-2-苯乙酯2-Methyl-2-butenoicaci phenethyl ester C13H16O2 204 0.17
    90 33.469 二苯甲酮Benzophenone C13H10O 182 0.05
    91 34.547 beta-桉叶醇beta-Eudesmol C15H26O 222 0.41
    92 36.418 2, 2′, 5, 5′-四甲基联苯基2, 2′, 5, 5′- Methyl phenyl C16H18 210 0.08
    93 36.941 3, 7, 11-三甲基-2, 6, 10-十二烷三烯-1-醇; 3, 7, 11-Trimethyl-26, 10-dodecatrien-1-ol C15H26O 222 4.7
    94 36.960 正十五碳醛Pentadecana C15H30O 226 0.38
    95 37.258 1-石竹烯1-Caryophyllene C15H24 204 0.52
    96 37.329 十四酸甲酯Methyl myristate C15H30O2 242 0.36 0.52
    97 38.567 苯甲酸苄酯Benzyl benzoate C14H12O2 212 0.16 0.32 0.2
    98 38.796 菲Phenanthrene C14H10 178 0.19 0.67
    99 40.242 未知Unknown 未知Unknown 未知Unknown 0.1
    100 41.390 6, 10, 14-三甲基-2-十五烷酮6, 10, 14-Trimethyl-2-pentadecaone C18H36O 268 0.27 2.11
    101 41.819 邻苯二甲酸二异丁酯Diisobutyl phthalate C16H22O4 278 0.16 0.47 0.14
    102 42.714 十九醇Nonadecanol C19H40O 287 1.72
    103 43.402 十七烷酮Heptadecanone C17H34O 254 0.19
    104 43.433 (Z)-十六烯酸甲酯Methyl palmitoleate C17H32O2 268 0.12 0.42 0.24
    105 43.618 法尼基丙酮(E, E)-6, 10, 14-Trimethylpentadeca-5, 9, 13-trien-2-one C18H30O 262 0.17
    106 44.214 棕榈酸甲酯Methyl palmitate C17H34O2 270 0.81 2.97 0.18
    107 44.219 邻苯二甲酸二丁酯Dibutyl phthalate C16H22O4 278 0.39 21.45
    108 45.502 棕榈酸乙酯Ethyl palmitate C18H36O2 284 0.39 10.59
    109 47.236 十七酸甲酯Methyl margarate C18H36O2 284 0.13
    110 49.275 亚油酸甲酯Methyl linoleate C19H34O2 294 6.84 0.47
    111 49.276 9, 12, 15-十八烷三烯酸甲酯Methyl linolenate C19H32O2 292 0.09 15.59
    112 49.283 醋酸(Z)-9-十四烯酯(Z)-9-Tetradecene acetate C16H30O2 254 0.19
    113 49.626 叶绿醇Phytol C20H40O 296 0.11 0.34 1.61
    114 49.748 硬脂酸甲酯Methyl stearate C19H38O2 298 0.5 0.13
    115 49.952 醋酸(Z)-11-十四烯酯11-Tetradecen-1-yl acetate C16H30O2 254 1.02
    116 50.02 (Z)-氧代环十七碳-8-烯-2-酮Oxacycloheptadec-8-en-2-one C16H28O2 252 0.47 1.07
    117 50.409 亚麻酸乙酯Ethyl linolenate C20H34O2 306 3.02
    118 50.411 亚油酸乙酯Ethyl linoleate C20H36O2 308 0.92
    119 50.483 油酸乙酯Ethyl oleate C20H38O2 310 1.04 2.39
    120 50.681 香叶基香叶醇Geranylgeraniol C20H34O 290 0.5
    121 50.762 硬脂酸乙酯Ethyl stearate C20H40O2 312 0.07 0.26
    122 54.921 二十二烷酸甲酯Methyl behenate C23H46O2 354 0.83 0.25
    123 57.903 二十四酸甲酯Methyl lignocerate C25H50O2 382 0.08
    124 57.907 木蜡酸甲酯Methyl tetracosanoate C25H50O2 382 0.17
    125 58.809 反式角鲨烯(E, E, E, E)-Squalene C30H50 410 0.17
    下载: 导出CSV

    表  2  3种金银花共有物分析表

    Table  2.   Analysis in the same component of three kinds of honeysuckle

    化合物名称Compound name 分子式Formula 分子量Formula weight 相对百分含量Relative percentage content/%
    菰腺忍冬Lonicera hypoglauca 灰毡毛忍冬Lonicera macranthoides 黄褐毛忍冬Lonicera fulvotomentosa
    苯乙烯Styrene C8H8 104 0.11 0.12 0.12
    苯甲醛Benzaldehyde C7H6O 106 0.1 0.27 0.12
    芳樟醇Linalool C10H18O 154 48.45 43.36 4.58
    2, 2, 6-三甲基-6-乙烯基四氢-2H-呋喃-3-醇2, 2, 6-TriMethyl-6-vinyltetrahydro-2H-pyran-3-ol C10H18O2 170 0.07 0.55 0.48
    alpha-松油醇alpha-Terpineol C10H18O 154 11.3 10.51 0.91
    橙花醇Nerol C10H18O 154 2.74 2.64 0.43
    香叶醇Geraniol C10H18O 154 10.78 10.41 9.63
    茴香脑Anethole C10H12O 148 0.19 0.3 0.1
    香芹酚Carvacrol C10H14O 150 0.28 0.13 0.42
    大马士酮beta-Damascenone C13H18O 190 0.75 0.78 1.12
    香叶基丙酮Geranyl acetone C13H22O 194 0.09 0.23 0.4
    苯甲酸苄酯Benzyl benzoate C14H12O2 212 0.16 0.32 0.2
    邻苯二甲酸二异丁酯Diisobutyl phthalate C16H22O4 278 0.16 0.47 0.14
    (Z)-十六烯酸甲酯Methyl Palmitoleate C17H32O2 268 0.12 0.42 0.24
    棕榈酸甲酯Methyl palmitate C17H34O2 270 0.81 2.97 0.18
    叶绿醇Phytol C20H40O 296 0.11 0.34 1.61
    1-辛烯-3-醇1-Octen-3-ol C8H16O 128 - 0.18 0.23
    反式-2-壬烯醛(E)-Non-2-enal C9H16O 140 - 0.31 0.3
    1-癸醇1-Nonanol C10H22O 158 - 0.28 0.71
    反式-2, 4-癸二烯醛trans, trans-2, 4-Decadienal C10H16O 152 - 0.3 0.72
    十四酸甲酯Methyl myristate C15H30O2 242 - 0.36 0.52
    6, 10, 14-三甲基-2-十五烷酮6, 10, 14-Trimethyl-2-pentadecaone C18H36O 268 - 0.27 2.11
    棕榈酸乙酯Ethyl palmitate C18H36O2 284 - 0.39 10.59
    亚油酸甲酯Methyl linoleate C19H34O2 294 - 6.84 0.47
    硬脂酸甲酯Methyl stearate C19H38O2 298 - 0.5 0.13
    油酸乙酯Ethyl oleate C20H38O2 310 - 1.04 2.39
    硬脂酸乙酯Ethyl stearate C20H40O2 312 - 0.07 0.26
    右旋萜二烯D-Limonene C10H16 136 0.3 0.34 -
    (Z)-3, 7-二甲基-1, 3, 6-十八烷三烯(Z)- 3, 7-Dimethyl-1, 3, 6-octatrieneY C10H16 136 1.73 0.46 -
    (-)-4-萜品醇(-)-4-Terpineol C10H18O 154 3.48 0.09 -
    乙酸壬酯Nonyl acetate C11H22O2 186 0.25 0.24 -
    菲Phenanthrene C14H10 178 0.19 0.67 -
    (Z)-氧代环十七碳-8-烯-2-酮Oxacycloheptadec-8-en-2-one C16H28O2 252 0.47 1.07 -
    二十二烷酸甲酯Methyl behenate C23H46O2 354 0.83 0.25 -
    苯乙醛Phenylacetaldehyde C8H8O 120 1.12 - 0.89
    邻苯二甲酸二丁酯Dibutyl phthalate C16H22O4 278 0.39 - 21.45
    9, 12, 15-十八烷三烯酸甲酯Methyl linolenate C19H32O2 292 0.09 - 15.59
    下载: 导出CSV

    表  3  不同种类金银花精油成分比较

    Table  3.   Comparison in component of essential oil for different types of honeysuckle

    化合物种类及含量
    Compound types and content
    灰毡毛忍冬
    Lonicera macranthoides
    菰腺忍冬
    Lonicera hypoglauca
    黄褐毛忍冬
    Lonicera fulvotomentosa
    文献[15]
    Literature[15]
    酸类Acids 相对含量Relative content/% 0.25 0 0.48 0.8
    个数Number 1 0 2 1
    烃类Hydrocarbon 相对含量Relative content/% 6.15 5.01 0.12 22.53
    个数Number 8 15 1 21
    酮类Ketone 相对含量Relative content/% 2.52 1.57 6.11 5.49
    个数Number 5 6 7 4
    酯类Esters 相对含量Relative content/% 15.32 3.17 57.92 12.81
    个数Number 16 10 20 6
    酚类Phenols 相对含量Relative content/% 1.14 0.48 0.91 22.81
    个数Number 3 2 3 4
    醇类Alcohol 相对含量Relative content/% 71.17 86.32 25.69 25.18
    个数Number 11 13 23 8
    醛类Aldehydes 相对含量Relative content/% 2.13 1.22 5.58 3.00
    个数Number 7 2 11 4
    其他种类Other types 相对含量Relative content/% 1.32 2.23 3.19 1.19
    个数Number 3 6 3 1
    C5~C10 相对含量Relative content/% 78.28 84.84 34.28
    个数Number 27 22 41
    C11~C15 相对含量Relative content/% 3.5 8.84 6.27
    个数Number 8 13 13
    C16~C20 相对含量Relative content/% 17.48 3.11 59.33
    个数Number 15 11 15
    其他C Other C 相对含量Relative content/% 4 8 1
    个数Number 0.74 3.21 0.09
    下载: 导出CSV
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  • 收稿日期:  2016-06-03
  • 修回日期:  2016-09-23
  • 刊出日期:  2017-02-01

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