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异叶青兰挥发油成分分析



全 文 :异叶青兰挥发油成分分析
陆 曼 , 田 暄*
(兰州大学应用有机化学国家重点实验室 , 兰州 730000)
摘要 目的:对维族 、藏族传统用药异叶青兰挥发油成分进行分析研究。 方法:用水蒸汽蒸馏法提取异叶青兰
挥发油并通过气相色谱/质谱技术对其进行分析鉴定。结果:已鉴定出 86 种成分 , 含有大量萜类化合物。并对其药
效进行初步分析。挥发油中具有平喘 ,镇咳 、杀菌等功效的药用成分约占总量的 60%, 其中香茅醇含量高达 50.7%,
其次为芳樟醇 、香茅醛 、桉油精 、石竹烯等。结论:异叶青兰不仅具有重要的药用价值 , 而且还是一种可开发利用的
经济型香料植物。
关键词 气相色谱/质谱;异叶青兰
  异叶青兰[ 1] (Dracocephalum heterophy llum
Benth)系唇形科植物 ,又名白甜蜜蜜 、白花枝子花
等 ,其气味香甜清润 ,闻之令人神清气爽 ,是维族 、藏
族用于治疗咳喘病和胃病的传统用药。有明显的平
喘镇咳作用 ,更以花香浓郁者效果显著。但对其挥
发油成分的研究至今未见报道 。本工作采用水蒸汽
蒸馏法提取异叶青兰挥发油 ,并利用 GC/MS 技术
对其成分进行分析鉴定 ,对照文献资料对其药效进
行了初步分析。
材 料 和 方 法
仪器与药品 HP 6890/5973 GC/MS 仪(美国
HP 公司);异叶青兰采自青海省玉树县 ,由中国科
学院西北高原生物研究所芦学锋副研究员鉴定;所
用溶剂均为分析纯。
萃取方法  将干燥粉碎的异叶青兰地上部分
350 g ,用 25%NaCl溶液室温冷浸 24 h后置于自制
的压力共沸蒸馏器中蒸馏 3 ~ 4 h ,收集馏出液 ,食盐
饱和后用乙醚萃取 3 次 , 萃取液浓缩后再经无水
Na2SO4 干燥得黄色透明具有浓郁芳香味的精油
2.485 g ,精油产率 0.7%。
色谱条件 HP-5 (30 m ×0.25 mm)弹性石英
毛细管柱(相似于 SE-54);柱温:60℃·min-1升至
收稿日期:1999-04-15
*联系人 Tel:(0931)8912410 , Fax:(0931)8912582 ,
E-mail:Xuant@lzu.edu.cn
280℃,气化室:300℃, 离子源:250℃, 色质界面:
280℃,分流比:40∶1 ,He气流速:1.2 mL·min-1 ,EI
源 ,倍增器1 400 V 。
图谱检索  G 1033A NIST PBM 谱图库;G
1036A NIST 结构数据库。
结 果 与 讨 论
异叶青兰水蒸汽蒸馏得精油的气相色谱/质谱
总离子流图见图 1 ,已鉴定出的各组分的名称 、含
量 、保留时间等见表 1。
Fig 1  Diag ram of total ion current of the
essential oil of Dracocephalum heterophllum
Benth.
·925·药学学报 Acta Pharmaceutica Sinica 1999 , 34(12)∶925 ~ 927
DOI :10.16438/j.0513-4870.1999.12.010
Tab 1 Chemical constituents in essential oil of Dracocephalum heterophllum Benth
Peak
No.
Retention
time/min Compound
Content/
%
 Peak
 No.
Retention
t ime/min Compound
Content/
%
1 3.20 Ethylbenzene 0.2 42 17.62 Acetophenone , 4 -methoxy- 0.2
2 3.29 1 , 3-Dimethyl-benzene 0.7 43 17.74 cis-2 , 6-dimethyl-2 , 6-Octadiene 1.3
3 4.23 1-Methylethyl-benzene <0.1 44 17.82 Phenol , 2-methoxy-3-(2-propenyl)- 1.4
4 4.38 3-Buten-2-ol 0.1 45 18.72 Cyclobuta [ 1 , 2:3 , 4] dicyclopentene , 0.3
5 4.99 Benzaldehyde 7.3 decahydro-3a-methyl-6-methylene-1-
6 5.36 1-Octen-3-ol 0.3 (1-methylethyl)-[ 1S-(1 ,α, 3a ,α,
7 5.69 5-Hepten-2-ol , 6-methyl- <0.1 3b , β , 6a , β , 6b , a)]
8 5.76 5-E thyl-3-methylhept-1-en-4-ol <0.1 46 18.80 Geranylacetate 0.3
9 6.17 2 , 4-Heptadienal ,(E , E)- <0.1 47 19.92 Garyophyllene 0.4
10 6.67 Limonene 0.3 48 20.44 γ-Elemene 0.1
11 6.75 Eucalyptol 0.9 49 20.78 γ-Cadinene 0.3
12 6.80 Benzyl alcohol 0.2 50 21.09 α-Caryophyllene 0.5
13 7.09 Benzeneacetaldehyde <0.1 51 21.26 β-S esquiphellandrene <0.1
14 7.22 1 , 3 , 7-Octat riene , 3 , 7-dimethyl <0.1 52 21.43 Epi-bicyclosesquiphellandrene 0.7
15 7.95 2-Furanmethanol , 5-ethenyltetrahydro-α, 0.3 53 22.03 Germacrene D 0.2
α, 5-t rimethyl-cis 54 22.26 3-Buten-2-one , 4-(2 , 6 , 6-trimethyl- 0.1
16 8.79 Linalool 2.2 1-cyclohexen-1-yl)-
17 9.16 1H-pyran , t et rahydro-4-methyl-2-(2- 2.4 55 22.56 Cyclohexane , 1-ethenyl-1-methyl-2-(1- 1.5
methyl-1-propenyl)- methylethenyl)-4-(1-methylethylidene)-
18 9.23 Benzylethyl alcohol 0.5 56 23.50 δ-Cadinene 0.2
19 9.47 2-Cyclohexen-1-ol , 1-methyl-4-(1- 0.1 57 23.65 2(4H)-Benzofuranone , 5 , 6 , 7 , 7a- 0.2
methyethenyl)-, t rans- tet rahydro-4 , 4 , 7a-t rimethyl-
20 10.30 Cyclohexanol , 5-methyl-2-(1-methylethenyl)- 0.3 58 25.26 Spathulenol 0.6
21 10.58 Citronellal 0.9 59 25.42 Caryophyllene oxide 0.5
22 10.81 Bicyclo[ 3 , 1 , 1] heptan-3-one , 2 , 6 , 6- 2.3 60 25.86 3-Cyclohexene-1-menthol ,α, 4-dimethyl- 0.1
t rimethyl-(1α, 2α,5α)- α-(4-methyl-3-pentenyl)-[ R-(R*, R*)]-
23 10.90 Bicyclo[ 2 , 2 , 1] heptan-3-one , 6 , 6- 0.2 61 26.07 Ledol <0.1
dimethyl-2-methylene- 62 26.27 12-Oxabicyclo[ 9 , 1 , 0] dodeca-3 , 7-diene , 0.2
24 11.38 3-Cyclohexen-1-ol , 4-methyl-1-(1- 0.1 1 , 5 , 5 , 8-tet ramethyl-[ 1R-(1R *, 3E ,
methylethyl)-,(R)- 7E , 11R*)]-
25 11.52 Azulene 0.1 63 26.58 Diphenylamine 1.1
26 11.61 Ethanone , 1-(4-methylphenyl)- 0.1 64 27.72 α-Cadinol 0.2
27 11.71 2-Cyclohexen-1-one , 4-(1-methylethyl)- 0.1 65 29.18 Heptadecane <0.1
28 11.86 3-Cyclohexene-1-methanol ,α,α, 4- 0.2 66 31.04 Benzyl Benzoate <0.1
t rimethyl-(α-terpinol) 67 31.14 Phenanth rene <0.1
29 12.07 Bicyclo[ 3 , 1 , 1] hept-2-ene-2-methanol , 0.6 68 32.18 Octadecane <0.1
6 , 6-dimethyl- 69 33.49 2-Pentadecanone , 6 , 10 , 14-t rimethyl- 0.1
30 13.46 Citronellol 50.7 70 34.03 Benzoic acid 2-hydroxy-phenylmethyl ester <0.1
31 13.90 2-Cyclohexen-1-one , 2-methyl-5-(1- 0.4 71 34.12 Dibutyl ph thalate <0.1
methylethenyl)-(S)(carvone) 72 35.05 Nonadecane <0.1
32 14.78 2 , 6-Octadienal , 3 , 7-dimethyl-, 0.5 73 35.70 Cit ronellol propanoate 0.2
(Z)-(neral) 74 37.78 Eicoane <0.1
33 14.94 Citronellyl formate 0.1 75 40.42 Heneicosane <0.1
34 15.55 2-p-Cymenol 0.2 76 40.73 Phytol <0.1
35 15.64 3-Cyclohexene-1-ethanol , β , 4-dimethyl 0.4 77 42.93 Docosane <0.1
[ R-(R *, R *)]- 78 43.41 1-Naphthalenamine , N-phenyl- <0.1
36 16.04 4-Hydroxy-3-methylacetophenone <0.1 79 45.33 Tricosane <0.1
37 16.15 3-Cyclohexene-1-acetalhyde ,α,4-dimethyl- 0.3 80 47.65 Tet racosane <0.1
38 16.66 Benzeneacetonit rile ,α,-hydroxy- 2.3 81 49.90 Pentacosane 0.1
39 16.81 1 , 4-Cyclohexadiene-1-methanol , 4-(1- 0.1 82 54.11 Heptacosane 0.3
methylethyl)- 83 55.65 9-Borabicyclo[ 3 , 3 , 1] nonane 9-(2- <0.1
40 16.99 Cyclohexanol , 2-(2-hyd roxy-2-propyl)- 0.2 iodo-1-hexenyl),(Z)
5-methyl- 84 56.12 Octacosane <0.1
41 17.07 Cyclohexanemethanol , 4-hyd roxy-α,α, 0.6 85 58.06 Nonacosane 0.1
4-t rimethyl- 86 59.94 Triacontane <0.1
·926· 药学学报 Acta Pharmaceutica Sinica 1999 , 34(12)∶925 ~ 927
  由表 1显示 ,异叶青兰挥发油的成分复杂 ,已鉴
定出化合物 86个 ,含有大量萜类化合物 。其中单萜
26个 ,倍半萜 17 个。此外还含有脂肪酸代谢生成
的脂肪烷烃等 。通过查阅文献资料[ 2] 可知异叶青
兰挥发油平喘镇咳效用与其含大量具有平喘 、镇咳 、
抗菌 、消毒的有效成分密切相关 。如:香茅醇
(50.7%),香茅醛(0.9%),芳樟醇(2.2%)等都有抗
菌 、抑菌 、抗病毒的功用;而桉油精(0.9%),宁烯
(0.3%), α-松油醇(0.29%),香芹酮(0.4%),石竹
烯(0.8%)等则都有平喘 、镇咳 、祛痰 、杀菌 、消毒的
作用 。这些药用成分在异叶青兰挥发油总含量中约
占60%,由此可见异叶青兰挥发油的药用价值较
大。同时 ,我们也看到异叶青兰发油中含有大量香
料成分[ 3] ,如:香茅醇(50.7%),香茅醛(0.9%),芳
樟醇(2.2%),橙花醛(0.5%),乙酸香叶酯(0.3%),
甲酸香茅酯(0.1%),桉油精(0.9%),宁烯(0.3%),
α-松油醇(0.2%),香芹酚(0.2%),苯乙醛(0.5%),
菲兰烯(0.8%)等 ,正是这些香料成分使异叶青兰具
有浓郁的芬芳。其中香茅醇(玫瑰油的主要成分)含
量竟达 50%以上。因此 ,异叶青兰不仅具有大的药
用价值 ,而且还是一种可开发利用的经济型香料植
物 。
References
1 Institute of Medicinal Plant Development , Institute of
Ma teria Medica, Chinese Academy of Medical Sciences.
The Annals of Chinese Medicinal Herb IV.2nd edition.
Beijing:People s Health P ress , 1988.57 ~ 60
2 Jiang JW , Xiao QX , eds.The Manual of Active Principle
of Medcinal Plants.Beijing:People s Health P ress , 1986
3 Zhu RH , Xue QC , Li Z , eds.The Manual of Synthetic
Edible Per fume.Beijing:Light Industry P ress , 1989
ANALYSISOF ESSENTIAL OIL OF
DRACOCEPHALUM HETEROPHYLLUM BENTH
Lu Man(Lu M)and Tian Xuan(Tian X)
(National Laboratory of Applied Organic Chem istry , Lanzhou Universi ty , Lanzhou 730000)
ABSTRACT AIM:To study the chemical components of essential oil of the Chinese medicinal herb
Dracocephalum heterophyllum Benth.METHODS:The essential oil w as ex tracted by steam dist illation and
analy zed by GC/MS.RESULTS:86 compounds have been ident if ied w hich contains a large number of terpenes.
The medicinal ef fects of these compounds have been analyzed preliminarily .CONCLUSION:Of the total
composi tions , the essential oil of Dracocephalum heterophy llum Benth contains about 60% medicinal
compounds , w ith ant iasthmatic , anticoughing and disinfectant actions.Among them the content of cit ronellol
reached 50.7%, then follow ed by linalool , cit ronellal , eucalyptol and caryophy llene etc.Therefore ,
Dracocephalum heterophyl lum Benth is a kind of valuable plant not only for its medicinal value but also for it s
economical benef it.
KEYWORDS GC/MS;Dracocephalum heterophy llum Benth
·927·药学学报 Acta Pharmaceutica Sinica 1999 , 34(12)∶925 ~ 927