Chemometrics-Assisted GC-MS Analysis of Volatile and Semi-Volatile Constituents of Elettaria cardamomum

Multivariate curve resolutions (MCR) along with other chemometric techniques are proposed to improve the analysis of Iranian Elettaria cardamomum (E. cardamom) essential oil with gas chromatography-mass spectrometry (GC-MS). In addition, multivariate curve resolution-alternating least squares (MCR-ALS) is used to obtain pure elution and mass spectral profiles for the components present in each chromatographic segment as well as their relative concentrations. This strategy was also used to overcome the problems of baseline offset, asymmetric peaks, retention time shifts, and overlapped and embedded peaks occurring during GC-MS analysis. The analysis of GC-MS data revealed that 42 components exist in the E. cardamom essential oil. However, with the help of MCR and different chemometric methods, this number was extended to 73 components. The most important components of the Iranian E. cardamom are α-terpineol acetate (11.78 %), linalool (10.15 %), nerolidol (8.82 %), α-pinene (8.11 %), geranyl acetate (3.47 %),1,8-cineole (4.25 %), and γ-terpinene (3.88 %).     

Headspace Adsorptive Microextraction Analysis of Oregano Fragrance Using Polyaniline-Nylon-6 Nanocomposite,GC-MS,and Multivariate Curve Resolution

Volatile components of oregano (Origanum vulgare L.) were extracted using headspace adsorptive microextraction and were analyzed by gas chromatography-mass spectrometry. Novel polyaniline-nylon-6 nanocomposite was used for headspace adsorptive microextraction due to its suitable characteristics. Multivariate curve resolution-alternating least square was applied for resolving the co-eluted gas chromatography-mass spectrometry peak clusters into pure chromatograms and mass spectra. Problems such as low signal-to-noise ratio of peaks and noisy data were handled with the aim of chemometrics. Chemicals of γ-terpinene, p-cymene, thymol, and carvacrol are the main components among 48 identified components of oregano fragrance. The volatile components of the fragrance and the essential oil of oregano were compared in term of chemical components and relative percentages points of view. The reproducibility in peak responses was investigated using three replicate experiments for the fragrance and the essential oil samples. The results proved that headspace adsorptive microextraction, gas chromatography-mass spectrometry, and multivariate curve resolution techniques could be useful to extract and analyze natural aromas and fragrances.     

Functional components,antidiabetic, anti-Alzheimer’s disease,and antioxidant activities of Salvia syriaca L.

Antidiabetic, anti-Alzheimer, general toxicity, and antioxidant activities of Salvia syriaca were evaluated. Phytochemical composition of the essential oil and methanolic extract of the plant were identified using gas chromatography-mass spectrometry and reverse-phase high-performance liquid chromatography-diode array detector techniques, respectively. Essential oil of S. syriaca exhibited strong cytotoxicity, antioxidant, α-amylase, and α-glucosidase inhibitory activities. Gas chromatography-mass spectrometry analysis showed that spathulenol (87.4%), isospathulenol (7.6%), and bornyl acetate (2.7%) are the major compounds in essential oil. High-performance liquid chromatography analysis indicated that rutin, quercetin, apigenin, rosmarinic acid, and ferulic acid are the most abundant phenolic components. S. syriaca could be considered as a valuable source of bioactive natural compounds for functional foods, medical, and pharmaceutical applications.     

Composition of the essential oil of Stachys sericantha,S. gaziantepensis,and S. mardinensis (Lamiaceae) from Turkey

The genus Stachys L. one of the largest genera of Lamiaceae and Stachys species are used by many people for the therapeutic value of their essential oils. In this study, water-distilled essential oil of three species of Stachys was analysed. The analysis was performed by using gas chromatography-flame ionisation detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS) systems simultaneously. The major components found were hexadecanoic acid (23.7%), dodecanoic acid (11.3%), and caryophyllene oxide (10.7%) for S. sericantha P.H. Davis (endemic); α-pinene (53%), β-pinene (8.2%) for S. gaziantepensis M. Dinc and S. Do?u (endemic); Menthyl acetate (15.3%), isomenthone (15.0%), pulegone (10%), spathulenol (7.0%), and caryophyllene oxide (6.7%) for S. mardinensis (Post) R. Mill.     

Chemistry and Antioxidant Properties of Essential Oil and Oleoresins Extracted from the Seeds of Tomer (Zanthoxylum armatum DC)*

The seeds of Zanthoxylum armatum DC, on hydrodistillation, yielded 1.2% of the essential oil. The oleoresins were extracted by a Soxhlet extractor using ethanol, ethyl acetate, and isopropyl alcohol. Gas chromatography-mass spectrometry analysis of the essential oil resulted in the identification of 38 components, of which linalool (62%) and limonene (18.1%) were the major components. The major components of oleoresins were linoleic acid, palmitoleic acid, and linalool. The antioxidant potential of essential oil and oleoresins were evaluated by 2,2′-diphenyl picrylhydrazyl radical scavenging, Fe²⁺ chelating, ferric thiocyanate method, and various lipid peroxidation assays. The essential oil showed maximum antioxidant potential, whereas oleoresins showed moderate antioxidant activity.     

三种植物精油的成分分析及其抑菌活性比较

为比较柠檬草、茉莉花、姜黄三种植物精油的组成成分及其抑菌活性,本试验采用气相色谱-质谱联用仪（GC-MS）分析样品成分,进而通过滤纸片法和梯度稀释法分析样品的抑菌能力。试验结果表明：姜黄精油主要特征成分为姜黄酮（12.87%）、芳姜黄酮（38.53%）和姜酮（20.36%）,具有抑菌活性的成分包括莰烯（2.38%）等;柠檬草精油的主要成分为柠蒙烯（12.72%）、柠檬醛（8.52%）和异松油烯（17.53%）,具有抑菌活性的成分包括柠檬醛（8.52%）等;茉莉精油的主要特征成分为芳樟醇（11.88%）、乙酸苄酯（9.31%）和肉桂醛（31.87%）,具有抑菌活性的成分包括肉桂醛（31.87%）等。柠檬草精油、茉莉精油、姜黄精油对金黄色葡萄球菌的抑菌圈直径分别为20.10 mm、10.22 mm、7.84 mm,阳性对照的乳酸链球菌素抑菌圈直径则为13.40 mm。上述三种植物精油均包含具有一定抑菌活性的物质,且在抑菌圈试验中表现出抑菌性,与乳酸链球菌素相比,抑菌效果从强到弱依次为柠檬草精油>茉莉精油>姜黄精油。     

Comparative GC-MS Analysis of Bay Leaf (Laurus nobilis L.) Essential Oils in Commercial Samples

Chemical composition of Laurus nobilis essential oils traded as spice and medicinal items was analyzed by gas chromatography-mass spectrometry. Sixty-four compounds accounting between 91–99% of the total oil was identified. Qualitative and quantitative differences were found among essential oils obtained from bay leaves used both for cooking and medicinal purposes. The oxygenated compounds were the principal fraction in all analyzed oils and consisted in oxygenated monoterpenes (73.13%), in medicinal essential oil and oxygenated monoterpenes (37.60 and 29.82%), oxygenated sesquiterpenes (15.98 and 22.99%), and phenylpropanoids (24.78 and 26.33%), respectively, in commercial food items. A high content of methyl eugenol (19 ± 4%; 21 ± 1%) and α-terpinyl acetate (18 ± 5%; 17 ± 7%) was found in commercial food items, whereas 1,8-cineole (51%) and α-terpinyl acetate (10%) were the main compounds in commercial pharmaceutical items.     

万寿菊叶精油的提取及化学成分分析

采用水蒸气蒸馏法提取黑龙江产万寿菊叶精油,通过单因素和正交试验,研究万寿菊叶精油提取的最佳工艺条件。结果表明：最佳工艺条件为料液比1:6、蒸馏时间5h、加热温度1 1 0 ℃,此条件下精油的产率为0.0944%。采用气相色谱- 质谱法对精油的化学成分进行分析,共分离出31 个峰,鉴定出其中的29 个化合物,占总峰面积的93.55%。主要成分有异松油烯(37.02%)、2- 异丙基-5- 甲基-3- 环己烯-1- 酮(14.08%)、柠檬烯(13.08%)、β- 罗勒烯(8.78%)、石竹烯(4.18%)。     

Volatile constituents of the essential oil of Monodora myristica (Gaertn) dunal

The essential oil of Monodora myristica was obtained by steam distillation with a yield of 45-6 g kg^?1. The composition of the oil was analysed by gas chromatography and gas chromatography-mass spectrometry. The oil was found to contain 75% monoterpene hydrocarbons; the major compounds being α-phellandrene (50–4%), α-pinene (5–5%) and myrcene (4–35%). There were also a few sesquiterpene hydrocarbons (3%) and oxygenated compounds such as germacrcne-D-4-ol (9–5%). Germacrene-D-4-ol, α-pinene, Δ²-carene, β-caryophyllene, valencene. γ-muurolol and carvacryl acetate have not previously been reported in M myristica.     

Chemical Composition and Antimicrobial Activity of Essential Oil of Matricaria recutita

Matricaria recutita is a herbaceous plant belonging to the Asteraceae family. The present study reports the chemical composition and antimicrobial activity of M. recutita essential oil and its main compounds. The essential oil was obtained from the aerial parts of the M. recutita by hydrodistillation and analyzed by gas chromatography-mass spectrometry. The major components were α-bisabolol oxide (38%), followed by camphene (9.11%), sabinene (4.87%), limonene (6%),1,8-cineole (7.12%), camphor (6.54%), and α-pinene (6%). Essential oil of chamomile was evaluated for its antibacterial activities against three gram-positive and four gram-negative pathogenic bacteria. The essential oil and its main compounds were particularly active against Bacillus cereus, with the lowest minimum inhibitory concentration and minimum bactericidal concentration value (0.022 and 1.5 μg /mL). In conclusion, these results support the use of the essential oil and its main compounds for their antimicrobial properties.     

野生糙苏籽挥发油化学成分的分析

用水蒸汽蒸馏法从野生糙苏籽中提取挥发油,利用气相色谱- 质谱联用技术对其挥发油中的化学成分进行分离和结构鉴定,运用气相色谱面积归一化法确定各个成分的相对百分含量。从糙苏籽的挥发油中鉴出56 种成分,其主要成分为α- 里哪醇(13.38%)、石竹烯氧化物(11.21%)、1- 辛烯-3- 醇(8.38%)、邻苯二甲酸二异丁酯(8.22%)、亚麻酸乙酯(6.21%)等。对糙苏籽的挥发油进行了抗氧化实验和抗菌实验,结果表明糙苏籽挥发油对·OH 有明显的清除作用,糙苏籽的挥发油对实验菌株均有明显的抑制和灭活作用,特别是大肠杆菌ATCC25922 株和肺炎球菌32201 株的抑制作用表现得更为显著。     

Chemical Composition and Antioxidant Activity of Essential Oil and Oleoresins of Nutmeg (Myristica fragrans Houtt.) Fruits

Essential oil and oleoresins (ethanol, ethyl acetate, and iso-propyl alcohol) of Myristica fragrans were extracted by using Clevenger and Soxhlet apparatus, respectively. Gas chromatography-mass spectrometry analysis of essential oil showed the presence of 38 components representing about 99.6% of the total weight. Sabinene (29.4%) was found to be a major component along with beta pinene (10.6%), alpha pinene (10.1%), terpene-4-ol (9.6%), and several other minor components. The major component of all oleoresins contained elemicin. It has been observed that the essential oil and ethanol oleoresin showed better activity compared to other tested oleoresins and synthetic antioxidants, butylated hydroxyl anisole and butylated hydroxyl toluene. Furthermore, the activity of essential oil and oleoresins was measured for the inhibition of primary and secondary oxidation products in mustard oil by using peroxide, thiobarbituric acid, and p-anisidine values. In addition, these experiments were further supported by other complementary antioxidant assays, such as ferric thiocyanate method in a linoleic acid system, reducing power, chelating effect, and scavenging effects on 1,1′-diphenyl-2-picrylhydrazyl radical. Hence, the essential oil and ethanol oleoresin of M. fragrans could be considered as a natural food preservative.     

Essential oils of Lavandula bipinnata and their antimicrobial activities

The essential oils from dried leaves of Lavandula bipinnata (Roth) Kuntze (Lamiaceae), obtained by soxhlet extraction was analysed by gas chromatography–mass spectrometry (GC–MS) and was evaluated for in vitro antimicrobial activity. The most common components usually found in lavender essential oils were present in the oil samples analysed, out of 43 peaks, 29 components, which constitute 72.38%, were identified in the essential oil. The major constituents were transcarveol (18.93%), pulegone (8.45%), camphor (7.09%) and menthol (5.89%). Other constituents present in fairly good amounts are pipertone (4.65%), caryophyllene oxide (3.68%), linalyl acetate (3.37%) and bicyclogermacrene (3.09%). The essential oil was screened for antimicrobial activity by disc diffusion assay and minimum inhibitory concentration (MIC) against bacteria and fungus. Results reveal that L. bipinnata essential oils are inhibitory against the tested bacteria and fungal strains.     

VARIATIONS IN ESSENTIAL OIL COMPOSITION DURING MATURATION OF CORIANDER (CORIANDRUM SATIVUM L.) FRUITS

The composition of volatile components of the essential oils extracted from fruits of coriander ( Coriandrum sativum L.) at four stages of maturity was studied by gas chromatography–flame ionization detector and gas chromatography-mass spectrometry. Essential oil yields showed marked increase during maturation process and 41 compounds were identified. Linalool was the main compound in all ripening stage amounting from 36.69 to 72.35%. Geranyl acetate (35.17%), β-caryophyllene (3.47%) and borneol (3.26%) were the main compounds at the first stage of maturity (immature fruits). At the second stage, geranyl acetate (8.21%), camphor (4.01%) and menthol (2.96%) were reported as the main constituents. In the third stage, geranyl acetate (20.66%), α-humulene (5.44%) and limonene (1.68%) were the main compounds. At the final stage of maturity (mature fruits), essential oil consist mainly on geranyl acetate (1.49%) and borneol (0.97%) in addition to linalool (72.35%). Additionally, accumulation of monoterpene alcohols was observed during maturation process of coriander fruit.

PRACTICAL APPLICATIONS

The chemical composition of the essential oil of coriander ( Coriandrum sativum L.) fruits is characterized by the occurrence of numerous components with great economical values. The oxygenated monoterpene and linalool were the most used ingredient in the cosmetic, perfume and food industries. On the other hand, the increasing market demands of the oxygenated components, widely present in this oil make it in the first rank of natural product. The formers were only obtained from the mature fruits. In this context, knowledge of their evolution during maturation process of the fruits seems to be a helpful tool for a better use of this economical potential.     

Antioxidant and antimicrobial activities of essential oil and various oleoresins of Elettaria cardamomum (seeds and pods)

BACKGROUND: This paper describes the chemical analysis of the essential oil and various oleoresins of Elettaria cardamomum (seeds and pods) by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) techniques. It also compares the effects of the different extraction solvents used (chloroform, methanol, ethanol and diethyl ether) on the antioxidant and antimicrobial activities of the essential oil and oleoresins. RESULTS: The essential oil was found to contain 71 compounds. The major components were α‐terpinyl acetate (44.3%), 1,8‐cineole (10.7%), α‐terpineol (9.8%) and linalool (8.6%). The chloroform and methanol oleoresins both contained α‐terpinyl acetate (21.8 and 25.9% respectively) as the main component, while 5‐hydroxymethylfurfural (28.9%) was the most abundant compound in the ethanol oleoresin. However, very few components (total 0.61%) were found in the diethyl ether oleoresin. The antioxidant activities of the essential oil and oleoresins, studied in mustard oil by monitoring the peroxide value of the oil substrate, were comparable to those of the synthetic antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) at 0.02% concentration. The essential oil exhibited strong antibacterial activity against the micro‐organisms Staphylococcus aureus, Bacillus cereus, Escherichia coli and Salmonella typhi at 3000 ppm by the agar well diffusion method. Antifungal activity was tested against the food‐borne fungi Aspergillus terreus, Penicillium purpurogenum, Fusarium graminearum and Penicillium madriti. The methanol and ethanol oleoresins gave the best results against A. terreus at 3000 ppm by the poison food method. CONCLUSION: This study provides important information about the chemistry and antioxidant and antimicrobial properties of E. cardamomum. Copyright © 2007 Society of Chemical Industry     

Fast profiling of food by analytical pyrolysis

The analytical application of direct pyrolysis (Py) field ionization (FI)-mass spectrometry (MS) und Curie-point pyrolysis gas chromatography-mass spectrometry (Py-GC/FIMS) to various whole foodstuffs is described for the first time. The former technique yields highly differentiated information from the sample in typically 15 min, namely the molecular weight distribution of released volatiles and pyrolysis products in a single spectrum which, owing to the good reproducibility and high significance of the resulting data, has previously been shown to be suitable for the application of chemometric methods. Such mass spectral peaks are further characterized and assigned by high resolution mass measurement and/or by electron ionization after Curie-point pyrolysis and gas chromatographic separation of the components. In this first report, typical results are presented for ground roasted coffee, rosehip tea, wheatmeal biscuit, chocolate drink powder and milk chocolate. The FI mass spectrum obtained from the latter sample is compared with those obtained using the complementary soft ionization techniques of chemical ionization (CI) and direct chemical ionization (DCI).     

基于GC-MS和GC-IMS联用法分析不同采收期广佛手精油挥发性成分

以不同采收期广佛手提取的精油为研究对象，采用气相色谱-质谱（gas chromatography-mass spectrometry，GC-MS）和气相色谱离子迁移谱（gas chromatography-ion mobility spectrometry，GC-IMS）技术分析广佛手精油含量和挥发性成分的变化。结果表明，广佛手精油含量在9月达到峰值。GC-MS和GC-IMS技术在5?个采收期广佛手精油中分别鉴定出54?种和61?种挥发性成分，主要为萜烯类，其次为醇类、醛类和酯类等化合物。GC-MS结果表明，醇类、醛类、酯类、烷烃类和酚类物质主要存在于8月、9月样品中，且含量较少。GC-IMS结果表明，醛类、酯类和酸类化合物主要存在于6月、7月和8月样品中。通过热图聚类和主成分分析化学计量法对5?个采收期广佛手精油进行区分。2?种技术的检测结果呈现一定的差异性，GC-MS技术检测出的大部分为大分子（C9～C21）高含量挥发性成分，而GC-IMS检测出的多为小分子（C2～C10）低含量挥发性成分。2?种技术相结合扩大了样品中挥发性组分的检测范围，更加全面直观地反映广佛手精油中挥发性成分的变化情况，为广佛手精油品质鉴别和其最佳采收时间的选取提供科学依据。     

江香薷挥发油的化学成分分析及其对金黄色葡萄球菌生物被膜的抑制作用

目的：研究江香薷挥发油的化学成分及其对金黄色葡萄球菌生物被膜的影响。方法：运用气相色谱-质谱（gas chromatography-mass spectrometry,GC-MS）技术鉴定江香薷挥发油的化学成分,并对其中相对含量较大的8 种化学成分的金黄色葡萄球菌生物被膜抑制作用进行研究。结果：GC-MS分析鉴定出29 种成分,其中相对含量比较大的成分为百里香酚、香荆芥酚、对聚伞花素、γ-松油烯、百里香酚乙酸酯、α-石竹烯、3-蒈烯和香荆芥酚乙酸酯。江香薷挥发油对金黄色葡萄球菌生物被膜形成的抑制率可达91.3%,对成熟的金黄色葡萄球菌生物被膜清除率为78.5%,香荆芥酚、3-蒈烯、香荆芥酚乙酸酯和α-石竹烯对金黄色葡萄球菌生物被膜的形成抑制作用显著,其中3-蒈烯的抑制率最高,为93.9%,而对聚伞花素和百里香酚乙酸酯对成熟的金黄色葡萄球菌生物被膜清除作用比较明显。结论：江香薷挥发油对金黄色葡萄球菌生物被膜形成有较强的抑制作用,也具有一定的成熟金黄色葡萄球菌生物被膜清除作用,这可能是江香薷挥发油中多种化学成分共同作用的结果。     

化学计量学法对紫苏叶与紫苏子挥发油共有组分分析

采用气相色谱-质谱(GC-MS)法分离测定紫苏叶与紫苏子挥发油成分,利用化学计量学解析法对重叠的色谱峰进行解析,得到各组分的纯色谱曲线和质谱,通过质谱库对解析的纯组分进行定性,紫苏叶挥发油的定性组分74个,占总含量的98.56%;紫苏子挥发油的定性组分85个,占总含量的97.92%。结果表明,紫苏叶与紫苏子挥发油共有组分数45个,分别占鉴定组分数的60.81%、52.94%;占鉴定组分量的66.38%、84.30%。相对含量较高的组分是柠檬烯、4,11,11-三甲基-8-亚甲基二环十一碳烯、2,6-二甲基-6-(4-甲基-3-戊烯基)双环庚-2-烯、石竹烯氧化物、1-(2-呋喃)-戊酮、3,6-二乙基-3,6-二甲基-三环己烷。     

微波辅助顶空固相微萃取法分析新疆洋葱籽挥发性成分

采用微波辅助萃取与顶空固相微萃取联合的方法萃取新疆洋葱籽挥发性成分,并用气相色谱-质谱联用技术分析对新疆洋葱籽中的挥发性成分进行了鉴定,共分离出50种成分,确认了其中的42种成分,占挥发性成分的95.46%。采用面积归一法确定各成分的相对百分含量,其中主要为萜类化合物及其衍生物。