全 文 ：北京大学学报(自然科学版) ,第 39 卷, 第 2 期, 2003 年 3 月
Acta Scientiarum Naturalium
Universitatis Pekinensis, Vol. 39, No. 2 (Mar, 2003)
1) 通讯联系人 Tel. 86-10-62538501, Fax. 86-10-62538501, E-mai l: zhouyawe@public. bta. net. cn
收稿日期: 2002- 05- 27
Identification of Fatty Acids and Other
Volatile Components of Mulgedium tatarica
by GC-MS Spectrometry
RENYulin ZHOUYawei1) YE Yunhua
( Key Lab of Bioorganic Chemistry and Molecular Engineering of Ministry of Education ,
College of Chemistry and Molecular Engineering , Peking University, Beijing, 100871 )
Abstr act Fatty acids and other volatile components of Mulgedium tatarica was detected by GC-MS method for
the first time. 17 compounds have been identified from the whole plant of M. tatarica . Fatty acid and paraffin are
the main components. The content of fatty acid is 4117% , and the content of hexadecanoic acid is 2318% .
Key words GC-MS; volatile components; fatty acid; Mulgedium tatarica ; Compositae
0 Introduction
Lactuca genus is a great genus in Compositae family.The genus has been changed to several genuses
since 1980, such as Cicerbita , Mulgedium , Ixeris , Crepidiastrum and Lactuca . Mulgedium genus is a
small genus with 15 species,mainly distributed in Europe and Asia. There are 5 species, Mulgedium ge-
nus, Mulgedium umbrosum (Dunn) Shih. , M. lessertianum DC. , M. tatarica ( L) DC. , M. monoceph-
alum(Chang) Shih. and M. bracreatum Shih in China, distributed in Yunnan Province, Tibet Autonomous
Region and Inner Mongolia Autonomous Region [1 ] . M. tatarica ( L) DC is widely distributed in central
Asia. It is not only a medicinal plant but also awild vegetable. It was reported that this plant showed sev-
eral bioactivities, such as diuretic action, stimulating milk secretion, analgesia and curing haemorrhoidoly-
sis[2 ] . However, there is little attention to the chemical constituents of it. Kisiel studied the isolation of
some sesquiterpene lactones from the plant
[3]
. Asada reported that sesquiterpene lactone was the major bi-
ologically active constituents in Compositae [4] . The plants in Lactuca genus are often used as anticancer
agents in folk [5 ] , therefore,we are interested in systematic chemical and bioactive study of M. tatarica .
Isidordv reported that an example of the essential oil from Artimesia pallens had been detected effi-
ciently by GC-MS
[6 ]
.Harada investigated the essential oil in the different parts of Artimisia capillaries
[7 ]
.
As we aware, there is no report concerning the study of the volatile components of Mulgedium genus.
Therefore, we analyzed the fatty acids and other volatile components of M. tatarica byGC-MSmethod. 17
DOI：10.13209/j.0479-8023.2003.025
volatile components were determined, and fatty acid and paraffin are the main components.
1 Results and Discussion
Fatty acids and other volatile components of M. tatarica were detected, and a method of extracting
and purifying fatty acids in M. tatarica was searched. Figure 1 is the chromatogram of the petroleum ether
fraction of the ethanol extract of the whole plant. This figure shows that most constituents are well separat-
ed and identified by comparison of their MS with those of the literature [8] .Comparing the MS spectra ob-
tained from the experiment with those in the literature and library search (Wiley 138 library) , the data
generated in the GC-MS study showed that the same typical fragmentation patterns and only slight
differences in relative peak intensities exit, allowing direct spectra data recognition by computerized
Fig. 1 GC profile of petroleum ether fr action of
extract of Mulgedium tatarica
routine ( library search) .
From the petroleum ether fraction of
the ethanol extract of the whole plant of
Mulgedium tatarica , 21 main components
were determined and 17 were identified.
Fatty acid and paraffin are two main kinds
of components. 5 fatty acids, tetradecanoic
acid, hexadecanoic acid, ( Z, Z)-9, 12- octa-
decadienoic acid, 9, 12, 15-octadecatrienoic
acid and octadecanoic acid were deter-
mined.These fatty acids, especially unsatur-
ated fatty acids are good for human health.
As well as, it reveals that GC-MS represents
a powerful high- resolution method for the
identification of fatty acid and other volatile
components of M. tatarica . The method of
extracting and purifying fatty acid in this experiment is successful. The type specific MS fragmentation
patterns provided helpful information for identification of many volatile components from this plant. All
components determined by GC-MS are shown in Table 1.
2 Experimental
211 General Experimental Procedures
GC-MS analysis was performed using a Hewlett-Packard system (Model 5971) . The chromatography
(Hewlett- Packard 5890) was fitted with a capillary column (Hewlett-Packard 1: 25m@012mm) , coated
with 100% dimethyl polysiloxane ( gum) . The oven temperature was maintained at 40 e for 2 minutes,
then raised to 250 e at the rate of 4 e per minute. The detector temperature was kept at 250 e . The
carrier gas was helium at a flow- rate of 0144mLPmin. The MS was recorded using a selective quadrupole
type detector (Hewlett-Packard 5971) . Ionization was obtained at 70 eV. The identification of separated
168 北 京 大 学 学 报 (自 然 科 学 版) 第 39 卷
components were based on GC retention index values and comparing the fragmentation patterns with those
reported in the literature and library search (Wiley 138 library) .
Table 1 The vola tile components of Mulgedium tatarica by GC-MS
Peak No. trPmin Compound Relative ContentP% Similarity1)P%
1 28. 00 2, 6-bis( 1, 1. - dimethylethyl)-4-methyl- phenol 2. 46 96
2 28. 11 pentadecane 1. 63 93
3 30. 62 hexadecane 3. 03 91
4 33. 00 heptadecane 3. 38 96
5 33. 17 tetradecanoic acid methyl ester 5. 81 97
6 35. 24 hexatriacontane 3. 19 90
7 35. 54 tritetracontane 1. 32 90
8 35. 90 6, 10, 14-trimethyl-2- pentadecanone 1. 28 97
9 36. 05 neophytytadiene 3. 04 96
10 36. 61 octadecane 2. 22 90
11 36. 94 unknown 2. 33
12 37. 39 nonadecane 3. 63 92
13 37. 61 hexadecanoic acid methyl ester 23. 76 99
14 38. 73 unknown 2. 41
15 39. 42 eicosane 2. 05 99
16 40. 05 unknown 1. 70
17 40. 58 unknown 3. 82
18 40. 87 ( Z , Z )-9, 12-octadecadienoic acid 3. 52 99
19 40. 95 9, 12, 15-octadecatrienoic acid methyl ester 6. 55 97
20 41. 36 tricosane 1. 38 91
21 41. 55 octadecanoic acid methyl ester 2. 10 99
1) MS of compounds determined compared with those in Wiley 138 library.
212 Plant Material
Mulgedium tatarica was collected in Inner Mongolia of China in July 2001, and it was identified by
Professor CHEN Yilin ( Institute of Botany, Chinese Academy of Sciences, Beijing) . A voucher specimen is
deposited in the College of Chemistry and Molecular Engineering, Peking University ( Beijing) .
213 Extraction and Isolation
The dried whole plants of M. tatarica ( 1 kg) were ground and extractedwith 95% ethanol ( 10 L) ,
refluxed about 3 h. The liquid was leached, and ethanol was removed under vacuum to residue, which was
solved inwater, and extracted by petroleum ether. Petroleum ether was removed to residue, which was sep-
arated with silica gel column chromatography, gradient eluted with petroleum ether-EtOAc( 0B1~ 10B1) .
Yellow oil ( 1 g) was obtained. 10mL methanol and 011 mL H2SO4 were added to 015 g yellow oil, re-
fluxed about 1 h, then cooled to room temperature. 5 mL water was added, extracted with ether ( 1 mL@
3) ,merged and leached ether, anhydrous Na2SO4 was added, sealed.
References
1 Zeng Jianfei. The Dictionary of Chinese Botany (Vol. 80) . Beijing: the Press of Sciences, 1997. 70~ 71
2 Yao Kecheng. Food Botany. Beijing: the Press of People. s Health, 1994. 354~ 358
169 第 2 期 任玉琳等: 蒙山莴苣脂肪酸及其他挥发性成分 GC-MS的研究
3 Wanda Kisiel, Barbara Barcy, Edward Syneler. Sesquiterpene Lactones from Lactuca tatarica . Phytochemistry, 1997,
45(2) : 365~ 368
4 Hidehisa Asada, ToshioMiyase, Seigo Fukushima. Sesquiterpene Lactones from Ixeris tamayawaensis Kitam Ó . Chem
Pharm Bull, 1984, 32(9) : 3 402~ 3 409
5 Bi Zhiming, Wang Zhengtao, Xu Guojun, et al. Studies on the Chemical Constituents and Cytotoxic Activity of Lactuca
la ciniata (Houtt) Makino. Journal of China Pharmaceutical University, 1996, 27(11) : 649~ 651
6 Isidordv VA, Zenkevich I G, Krajewska U, et al. Gas Chromatographic Analysis of Essential Oils with Preliminary Par-
tition of Compounds. Phytochemical Analysis, 2001, 12(1) : 87~ 90
7 Rokuro Harada, Mariko Iwasaki. Volatile Components of Artemisia capilloris. Phytochemistry, 1982, 21( 8) : 2 009~
2 011
8 Cong Puzhu. The Handbook of Analysis Chemistry ( 9th) . Beijing: the Press of Sciences, 2000. 170~ 171
蒙山莴苣脂肪酸及其他挥发性成分 GC-MS的研究
任玉琳 周亚伟 叶蕴华
(北京大学化学与分子工程学院, 教育部生物有机与分子工程重点实验室, 北京, 100871)
摘 要 首次应用气相色谱-质谱分析技术, 对蒙山莴苣全草中脂肪酸和其他挥发性成分进行研
究。从蒙山莴苣全草中鉴定了 17个挥发性成分,其中, 脂肪酸和脂肪烷为主要成分。脂肪酸含量
达 4117% , 而正十六碳酸的含量达 2318%。
关键词 气相色谱-质谱; 挥发性组分; 脂肪酸; 蒙山莴苣 ; 菊科
中图分类号 O 657163
* * * * *
简 讯
以血管内皮细胞生长因子为靶点的肿瘤血管生成阻断剂的
研究获得新进展
北京大学临床肿瘤学院寿成超教授领导的研究小组开展的以血管内皮细胞因子( VEGF)为靶点的肿瘤血
管生成阻断剂的研究取得重大进展。在历时 5年的研究过程中,他们发现, 肿瘤细胞不仅能表达 VEGF,而且
能表达被传统观点认为仅在血管内皮细胞特异表达的 VEGF受体KDR和Fet-1, 用VEGF 能直接刺激肿瘤细胞
的生长,说明 VEGF在肿瘤生长中起到了能同时促进血管内皮细胞和肿瘤细胞增殖的双重作用。为了阻断
VEGF的功能, 他们首先克隆和表达了 VEGF受体, 然后用VEGF 受体为靶点, 通过噬菌体表面呈现肽库技术,
最终从十二肽库中筛选获得了 2个能与 VEGF 特异结合、并且能中和 VEGF活性、抑制鸡胚尿囊膜血管形成及
荷瘤小鼠的肿瘤生长和转移的活性小肽,显示出所获得的小肽具进一步开发研究的前景,经过进一步工作,以
期最终获得具自主知识产权的抗肿瘤小肽药物。相关的主要结果已在国际著名刊物/ 生物学化学杂志0( JBC)
发表(Vo1. 277(45) , Nov. 2002) ,引起国际同行的关注。
(摘自5北大校刊6 2003-01-15)
170 北 京 大 学 学 报 (自 然 科 学 版) 第 39 卷