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Chemical Variation in the Essential Oil of Ephedra Sinica from Northeastern China

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Chemical Variation in the Essential Oil of Ephedra Sinica from Northeastern China Food Chemistry Food Chemistry 98 (2006) 52–58 www.elsevier.com/locate/foodchem Chemical variation in the essential oil of Ephedra sinica from Northeastern China Qingbiao Wang a, Yong Yang b, Xiaomin Zhao a, Bin Zhu a, Peng Nan a, Jiayuan Zhao a, Li Wang a, Fan Chen c, Zhijun Liu d, Yang Zhong a,* a Ministry of Education Key Laboratory for Biodiversity Science and Ecological Engineering, School of Life Sciences, Fudan University, Shanghai 200433, China b Institute of Botany, The Chinese Academy of Sciences, Beijing 100933, China c Institute of Genetics and Developmental Biology, The Chinese Academy of Sciences, Beijing 100101, China d School of Renewable Natural Resources, Louisiana State University Agricultural Center, Baton Rouge, LA 70803, USA Received 13 December 2004; received in revised form 18 April 2005; accepted 18 April 2005 Abstract Hydro-distillated volatile oils of Ephedra sinica Stapf. from six populations of Inner Mongolia in Northeastern China were ana- lyzed by using GC/MS. Ninety-nine compounds were identified in the oils and a relatively high variation in their contents was found. The main constituents of the essential oils were a-terpineol (19.28–52.23%), p-vinylanisole (0.59–11.64%), 3-methyl-2- buten-1-ol (0–5.44%), tetramethylpyrazine (0.63–8.99%), terpine-4-ol (1.17–4.37%), a-linalool (1.62–5.15%), phytol (1.24– 15.73%), c-eudesmol (0–7.77%), and eudesm-7(11)-en-4-ol (0.41–6.13). Six populations were divided into two chemotypes based on cluster analysis and principal component analysis (PCA); one rich in a-terpineol and p-vinylanisole, and the other rich in phytol, c-eudesmol, and eudesm-7(11)-en-4-ol. Ó 2005 Published by Elsevier Ltd. Keywords: Ephedra sinica; Essential oils; GC/MS; Chemotype; Northeastern China 1. Introduction Many Ephedra species, e.g., Ephedra nevadensis, Ephedra trifurca, Ephedra geradinia, and Ephedra sinica, The family Ephedraceae consists of about 50 species have been used as important medicinal herbs worldwide in the world (Price, 1996). Most of these species are dis- for a long time. In particular, E. nevadensis and E. tri- tributed in temperate and subtropical regions of Asia, furca grown in southwest America were used to make Europe, and North and Central Americas. The genus ‘‘Mormon tea’’, ‘‘joint-fir’’, or ‘‘Squaw tea’’. They were Ephedra consists of a group of perennial and dioecious brewed by the natives not only to treat allergies and shrubby plants growing up to 4 feet tall, with slender other cold symptoms, but also as a stimulant. In India and joined stems. Their leaves are reduced to scales and Pakistan, E. geradinia was used to produce a special and grow in opposite pairs or whorls of three. They usu- drink called ‘‘soma’’, which was believed to promote ally grow on plains, sandy soil, dry slopes, and dry longevity and its stems were used to treat asthma. mountain sides. E. sinica, also known as ‘‘Mahuang’’, is an endemic spe- cies of Mongolian region and one of the most famous medicinal plants in the world. In Inner Mongolia of * Corresponding author. Tel.: +86 2165642263; fax: +86 Northeastern China, the annual production of E. sinica 2165642468. E-mail address: [email protected] (Y. Zhong). has reached more than 100,000 tons. Most of the raw 0308-8146/$ - see front matter Ó 2005 Published by Elsevier Ltd. doi:10.1016/j.foodchem.2005.04.033 Q. Wang et al. / Food Chemistry 98 (2006) 52–58 53 material of Ephedra extracts in the world come from this rica and Satureja spicigera (Sefidkon, Jamzad, & Mirza, region. 2004). Although the main constituents of E. sinica were Historically, E. sinica has been used as an important reported, few studies on chemistry of the essential oils medicinal herb in China for more than 5000 years. were carried out (Miyazawa et al., 1997), nor chemical During the period of the ancient Chinese Han Dynasty, variation in the essential oils of Ephedra sinica has been E. sinica had been used to treat the common cold, asth- investigated. In this study, we collected six E. sinica pop- ma, bronchitis, and arthritis. The most common prepa- ulations from east to west Inner Mongolia of Northeast- ration of E. sinica was as a tea. Its stems were dried in ern China at the end of September, 2004, when E. sinica the sun and cut into pieces, boiled in water for about was thought to be of the best quality by Chinese tradi- thirty minutes, and the liquid extract was then tional pharmacologists, for determining the constituents consumed. In the last century, E. sinica became a most of the essential oils and evaluating population variation popular plant for its extract was used as central nervous of the oils. system (CNS) stimulants and mood enhancers as well as dietary supplements in various health foods in the wes- tern countries (Gurley, Wang, & Gardner, 1998), which 2. Materials and methods are claimed to be effective for weight-loss or as energy booster. In the past decade, however, more and more 2.1. Plant materials evidence suggested that the misuses or abuses of the herb could cause possible hazards to public health, even Samples of E. sinica were collected at the end of Sep- lead to cardiovascular symptoms, stroke, and death tember, 2004 from six locations in Inner Mongolia, Chi- (Haller & Benowitz, 2000; Zaacks, Klein, Tan, Rodri- na (Fig. 1): Chifeng-Wusan (N: 42°150; E: 118°470), guez, & Leikin, 1999). In February 2004, after an intense Chifeng-Sanyanjing (N: 42°140; E: 118°550), Zheng- debate, the United States Food and Drug Administra- xiangbaiqi (N: 42°150; E: 114°560), Hohhot (N: 40°230; tion (FDA) announced to ban the retail sales of dietary E: 111°540), Baotou (N: 40°520; E: 110°040), and Erto- supplements containing any of the ephedra alkaloids. keqi (N: 39°050; E: 107°580). All six populations grew Despite of this setback in use in the United States, on dry slopes with similar environments and no obvious E. sinica remains to be one of the most important medic- morphological variation was found among them. These inal herbs, especially in China. samples were identified and voucher specimens were Although the pharmacological activities exerted by deposited in the MOE Laboratory for Biodiversity Sci- E. sinica are believed to come primarily from ephed- ence and Ecological Engineering, Fudan University. rine-like alkaloids, other types of constituents such as The aerial parts of all samples were dried and stored essential oils are medicinal as well. For example, at room temperature and subsequently cut into small 2,3,5,6-tetramethylpyrazine and terpineol were found pieces for distillation of their essential oils. in the essential oils of E. sinica (Miyazawa, Minamino, & Kameoka, 1997). The former is a kind of cardiovascu- 2.2. Isolation of the essential oils lar drug (Liu et al., 1990) and the latter is an important raw material in pharmaceutical industry. Few studies on The aerial parts of the six samples, i.e., Chifeng-Wu- chemistry of the essential oils of E. sinica were carried san (600 g), Chifeng-Sanyanjing (540 g), Zhengxiangbai- out (Miyazawa et al., 1997) and athough the main con- qi (325 g), Hohhot (525 g), Baotou (410 g), and Ertokeqi stituents of this species were reported as a-terpineol (480 g), were subjected to hydrodistillation for 3 h in a (13.0%), tetramethylpyrazine (3.9%), terpinen-4-ol Clevenger-type apparatus. Each sample was repeated (3.9%), linalool (3.2%), 2,3-dihydro-2-methylbenzo-fur- for four times. The essential oils were collected and then an (3.1%) and cis-p-menth-2-en-7-ol (3.1%). stored with anhydrous sodium sulfate in Eppendorf As a class of compounds in plants with important tubes at 4 °C until analyzed and tested. functions in the defense against pathogenic fungi and attraction of pollinators, the compositions of the essen- 2.3. Analysis of the oils tial oils from many plants such as Melaleuca alternifolia, Hyptis crenata,andJasminum sambac, are closely re- The essential oils from the aerial parts of E. sinica lated to their genotypes and growing environments were conducted as previously described (Nan et al., (Lee et al., 2002; Rao & Rout, 2003; Zoghbi et al., 2003). Briefly, GC analyses were carried out on a HP- 2002). However, for a small number of plants, there is 6890 gas chromatography equipped with a FID and a no significant difference among different populations. HP-5 capillary column (30 m in length, 0.25 mm in For example, three populations of Satureja sahendica diameter, 0.25 lm in film thickness) using N2 as carrier collected from three different provinces in Northwestern gas (1 ml/min). A 1 ll aliquot of oil was injected into the and Western Iran belonged to one chemotype and their column using a 10:1 split injection, with temperature set oil composition was similar to that of Satureja bachtia- at 250 °C. The GC program was initiated by a column 54 Q. Wang et al. / Food Chemistry 98 (2006) 52–58 Fig. 1. Six sampling locations of Ephedra sinica in Inner Mongolia of Northeastern China. temperature set at 60 °C for 2 min, increased to 250 °C group method using an arithmetic average (UPGMA) at a rate of 10 °C/min, and held for 10 min. with the NTSYSpc version 2.02. GC/MS analyses were performed on a combined GC/ MS instrument (Finnigan Voyager, San Jose, CA, USA) with a HP-5 fused silica capillary column (30 m in 3. Results and discussion length, 0.25 mm in diameter, 0.25 lm in film thickness) using He as carrier gas (1 ml/min).
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