Investigation of Chemical Compositions and Biological Activities of Mentha suaveolens L. from Saudi Arabia

Mentha is an aromatic plant used since antiquity for its pharmaceutical virtues. The climate of Saudi Arabia favors the growth of aromatic plants including Mentha suaveolens L. The aim of this study is to analyze the volatile oils of different parts of fresh and dried Mentha suaveolens L. grown in Saudi Arabia (Aljouf area) using Gas Chromatography/Mass Spectrometry (GC/MS) and Gas Chromatography Flame Ionization Detector (GC/FID) techniques, to recognize the effect of drying on chemical composition, then to evaluate the antioxidant and antifungal activities of different extracts. In total, 118 compounds were identified via GC/MS and GC/FID, in which carvone is the main volatile constituent (stems, leaves, whole plant 45–64%). This investigation deduces that Mentha belonged to the carvone chemotype. Then, the analysis of non-volatile constituents of fresh and dried Mentha was performed by HPLC. The main phenolic compound of fresh and dried Mentha for different parts was rosmarinic acid (ranging from 28,002.5 to 6558 µg/g). The ethanolic extract of fresh stem showed the highest antifungal activity (53% inhibition) compared with miconazole (60% inhibition) but the ethanoic extract of dry stem showed no activity. Additionally, all ethanolic extracts, whether for fresh or dry Mentha, have antioxidant activity more than 90% while the antioxidant activity of whole plant volatile oil is equal to 53.33%. This research shows that M. suaveolens L. could be applied to manufacture natural antioxidants, antifungal, and flavoring agents.     

Identification of volatiles from pineapple (Ananas comosus L.) pulp by comprehensive two-dimensional gas chromatography and gas chromatography/mass spectrometry

Combining qualitative data from the chromatographic structure of 2-D gas chromatography with flame ionization detection (GC×GC-FID) and that from gas chromatography-mass spectrometry (GC/MS) should result in a more accurate assignment of the peak identities than the simple analysis by GC/MS, where coelution of analytes is unavoidable in highly complex samples (rendering spectra unsuitable for qualitative purposes) or for compounds in very low concentrations. Using data from GC×GC-FID combined with GC/MS can reveal coelutions that were not detected by mass spectra deconvolution software. In addition, some compounds can be identified according to the structure of the GC×GC-FID chromatogram. In this article, the volatile fractions of fresh and dehydrated pineapple pulp were evaluated. The extraction of the volatiles was performed by dynamic headspace extraction coupled to solid-phase microextraction (DHS-SPME), a technique appropriate for slurries or solid matrices. Extracted analytes were then analyzed by GC×GC-FID and GC/MS. The results obtained using both techniques were combined to improve compound identifications.     

Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity

Hydrodistillation (HD), simultaneous distillation solvent extraction (SDE), microwave-assisted hydrodistillation (MWHD), and supercritical fluid (CO2) extraction (SFE) were employed to isolate volatile secondary metabolites from fresh leaves and stems of Colombian Lippia alba (Mill.) N.E. Brown. Kovàts indices, mass spectra or standard compounds were used to identify around 40 components in the various volatile fractions. Carvone (40-57%) was the most abundant component, followed by limonene (24-37%), bicyclosesquiphellandrene (5-22%), piperitenone (1-2%), piperitone (ca. 1.0%), and beta-bourbonene (0.6-1.5%), in the HD, SDE, MWHD, and SFE volatile fractions. Static headspace (S-HS), simultaneous purge and trap in solvent (CH2Cl2) (P&T), and headspace solid-phase microextraction (HS-SPME) were used to sample volatiles from fresh L. alba stems and leaves. The main components isolated from the headspace of the fresh plant material were limonene (27-77%), carvone (14-30%), piperitone (0.3-0.5%), piperitenone (ca. 0.4%), and beta-bourbonene (0.5-6.5%). The in vitro antioxidant activity of L. alba essential oil, obtained by hydrodistillation was evaluated by determination of hexanal, the main carbonyl compound released by linoleic acid subjected to peroxidation (1 mm Fe2+, 37 degrees C, 12 h), and by quantification of this acid as its methyl ester. Under the same conditions, L. alba HD-essential oil and Vitamin E exhibited similar antioxidant effects.     

Volatile fingerprints of artemisinin-rich Artemisia annua cultivars by headspace solid-phase microextraction gas chromatography/ mass spectrometry

The cultivar Anamed (A3) is a hybrid of Artemisia annua with a high content of the secondary metabolite artemisinin, a well-known antimalarial drug. Here we report for the first time the volatile profile of fresh leaves of this hybrid in comparison with that of Artemisia annua L. wild-type species. Evaluation and comparison of the volatile profiles of A. annua genotypes with different content in artemisinin were carried out by headspace solid-phase microextraction (HS-SPME) coupled with gas chromatography/mass spectrometry (GC/MS) that was performed on fresh leaves of the plants under investigation using a polydimethylsiloxane (PDMS) fiber. The chromatograms obtained from hybrids with a high content of artemisinin (A. annua cv. Anamed A3 and A. annua cv. Artemis F2) reveal the total absence of artemisia ketone, one of the major and characteristic compounds of the wild-type A. annua L., along with a significantly lower variety of volatile compounds. In conclusion, HS-SPME coupled with GC/MS is a very useful, non-destructive and efficient method to describe the volatile pattern of Artemisia annua cultivars. It represents a rapid screening method for the evaluation of volatile biomarkers like artemisia ketone, whose absence is typical of artemisinin-rich A. annua cultivars.     

Hydrodistillation-adsorption method for the isolation of water-soluble, non-soluble and high volatile compounds from plant materials

Proposed method of hydrodistillation–adsorption (HDA) on activated carbon and hydrodistillation (HD) with solvent trap were compared for the isolation of water-soluble, non-soluble and high volatile compounds, such as acids, monoterpenes, isothiocyanates and others from carob (Certonia siliqua L.), rosemary (Rosmarinus officinalis L.) and rocket (Eruca sativa L.). Isolated volatiles were analyzed by GC and GC/MS. The main advantages of HDA method over ubiquitous HD method were higher yields of volatile compounds and their simultaneous separation in three fractions that enabled more detail analyses. This method is particularly suitable for the isolation and analysis of the plant volatiles with high amounts of water-soluble compounds. In distinction from previously published adsorption of remaining volatile compounds from distillation water on activated carbon, this method offers simultaneous hydrodistillation and adsorption in the same apparatus.     

Comparison of liquid-liquid extraction with headspace methods for the characterization of volatile fractions of commercial hydrolats from typically Mediterranean species

Chemical composition of volatile fractions of nine commercial hydrolats and corresponding essential oils obtained using an industrial process were studied. The hydrolat volatile fractions were reported for the first time. A comparative study of those obtained, on the one hand, by liquid-liquid extraction (LLE) and, on the other hand, using five solid-phase microextraction (SPME) fibers and also purge-and-trap-automatic thermal desorption (P&T-ATD) was conducted with analysis performed by GC and GC/MS. The use of various techniques has resulted in a change of chromatographic profile of the hydrolat volatile fractions. Quantitative differences were established between chemical compositions of headspace and those obtained by a conventional method (LLE). Statistical analyses were carried out to summarize the results.     

Essential oil from leaves of Lantana canescens and L. lopez-palacii grown in Colombia

The chemical composition of the volatile compounds from the leaves of Lantana canescens Kunth (Verbenaceae) and L. lopez-palacii Moldenke grown in Colombia were analyzed by GC and GC/MS. One hundred and thirty-nine volatile compounds were identified in L. canescens, of which the major ones were beta-caryophyllene (13.5%), germacrene D (10.3%) and 1-octen-3-ol (8.4%). In the oil obtained from L. lopez-palacii, eighty-three compounds were identified, of which the most prominent were 1-octen-3-ol (24.4%) and beta-caryophyllene (15.2%). The in vitro antibacterial activity of the L. lopez-palacii essential oil was studied against three bacterial strains using the disc diffusion method. No antimicrobial activity was found against Escherichia coli, Enterobacter sakazakii and Listeria monocytogenes.     

Isolation and identification of flower oil components from four <Emphasis Type="Italic">Staphylea</Emphasis> L. species

Chemical composition of the hydrodistilled volatile fraction from flowers of four Staphylea L. species (Staphylea colchica Stev., Staphylea elegans Zab., Staphylea holocarpa Hemsl., Staphylea pinnata L.) was determined by the GC/MS method. Compounds in fresh and dried flowers (stored for 1 year) were determined. Mostly, structures of different oxygenated aliphatic hydrocarbons in all four species were found. Different aldehydes, ketones, esters of higher fatty acids, and hexadecanoic acid were identified, with dominating content of tricosane, hexadecanoic acid and also of heneicosane, pentacosane, heptacosane, and nonacosane. In S. pinnata L. (fresh flowers) some nonaliphatic hydrocarbons, and in S. holocarpa Hemsl. (fresh flowers) esters of higher fatty acids were found.     

Essential oil of Turnera ulmifolia leaves from Cuba

The chemical composition of the volatile compounds from the leaves of Turnera ulmifolia L. (Turneraceae) from Cuba was studied by GC and GC/MS. Sixty-four volatile compounds were identified, of which the major ones were beta-caryophyllene (21.5%) and (Z)-3-hexen-1-ol (18.4%).     

Chemical composition of the essential oil of Thalectrum minus L. of Iran

The volatile constituents of the essential oil of Thalictrum minus L. growing wild in Kurdistan-Iran were investigated by GC and GC / MS technique. Twelve compounds, representing 100% of the total oil were identified. The main components were: Thymol (66.63%), para-Cymene (13.05%), gamma-Terpinene (7.32%), Carvacrol (3.70%), 1,8-Cineole (2.02%).     

小叶香樟新鲜树叶挥发性成分分析

采用水蒸汽蒸馏和乙醚萃取收集小叶香樟新鲜树叶挥发油,经气质联用分析鉴定出49个化合物,占峰面积的95.9%,挥发油得率为1.73%。主要化合物的类型为单萜(86.4%)、倍半萜(10.0%)、芳香族(1.41%)和脂肪族(1.13%)。其中质量分数最高的为L-芳樟醇(45.9%),其次为樟脑(28.5%)和橙花叔醇(4.66%)。     

GC and GC-MS Studies on the Essential Oil and Thiophenes from Tagetes patula L.

The production and the composition of the compounds (mono-, sesquiterpenes and acetylenic thiophenes) obtained by the steam distillation of Tagetes patula L. have been investigated. The volatile oil was produced by steam distillation. GC was carried out on three types of stationary phase using flame ionization and mass selective detection. Percentage data were calculated by the area normalization method with very good repeatability (RSD below 5%). Oils from flower-heads were rich in β-caryophyllene (53.5%) and the leaves contained terpinolene in high concentration (21.1%). The main volatile component of the hairy roots and intact roots was 5-(3-buten-1-ynyl)-2,2'-bithienyl (BBT) yielding 28.5% and 44.0% in the oils. Three new minor constituents were identified as α-gurjunene, β-caryophyllene and (E)-β-farnesene. A flash chromatographic method was developed for the isolation of thiophenes from a solvent extract of intact roots. The collected fractions were screened by TLC and analyzed by GC-MS. Three thiophene fractions were obtained containing BBT, 5-(4-acetoxy-1-butynyl)-2,2'-bithienyl (BBTOAc) and 5-(4-hydroxy-1-butynyl)-2,2'-bithienyl (BBTOH).     

Determination of extremely low percolation threshold electroactivity of the blend polyvinyl chloride/polyaniline doped with camphorsulfonic acid by cyclic voltammetry method

The percolation threshold of prepared blends of poly(vinyl chloride) (PVC) with doped polyaniline (PANi) from camphorsulfonic acid (CSA) was investigated by cyclic voltammetry. The blends were formed from N-methyl pyrrolidone (NMP) solutions and PANi-CSA/PVC with weight fractions from 0.1% to 0.005%. The film of blends were prepared by casting the above polymer solutions on a glass carbon (GC) electrode. Voltammograms were drew in a one-compartment cell fitted with a GC electrode, Pt electrode and SCE as working, auxiliary and reference electrode respectively, in 1 M perchloric acid as electrolytic solution. The obtained results showed that PANi-CSA/PVC blend onto 0.007% weight from PANi is electroactive. The structure and morphology of prepared blends were investigated by FT-IR spectra and optic microscope.     

Phytochemical analysis of Saponaria officinalis L. shoots and flowers essential oils

Phytochemical analysis by GC and GC/MS of the essential oil samples obtained from fresh shoots and flowers of Saponaria officinalis L. allowed the identification of 96 components in total, comprising 94.7% and 86.0% of the total oils compositions, respectively. Regarding the shoots essential oil, the major of 87 identified volatile compounds were phytol (14.1%), tricosane-6,8-dione (13.4%), patchouli alcohol (7.9%) and tricosane (7.2%), whereas patchouli alcohol (20.0%), heneicosane (11.5%) and tricosane (8.4%) were dominant among the 66 volatiles in the flower oil. Nonterpenoid compounds had the highest contribution in S. officinalis shoots essential oil (53.7%), while in the flower oil, constituents were almost evenly distributed between the oxygenated sesquiterpenoid (41.2%) and nonterpenoid compounds (39.5%).     

Headspace constituents of the tree remain of Cinnamomum camphora

The volatile ingredients isolated from a fresh tree of Cinnamomum camphora (camphor tree) and from a tree remain of C. camphora were collected by using headspace techniques and analyzed by means of gas chromatography/mass spectrometry (GC/MS). 99.77% of the constituents consisting 23 components from the fresh tree, 98.68% of the constituents consisting 24 components from the tree remain were identified. Of these ingredients, camphor was obtained as the most abundant component.     

Comparative Analysis of the Volatile Components in the Fresh Roots and Rhizomes of Curcuma wenyujin by Static Headspace Gas Chromatography Mass Spectrometry

Static headspace GC-MS method coupled with H/D exchange was firstly developed to determine and identifythe volatile components in the fresh root and rhizome of Curcuma wenyujin.The TIC chromatograms of 3 batchesof fresh roots harvested at different time showed significant difference in the volatile components:the constitutionwas the same but the content of them was different.More than 60 volatile components in fresh roots(Root of C.wenyujin)and rhizomes(Rhizome of C.wenyujin)of C.wenyujin were detected,of which 51 and 48 volatile com-ponents were identified respectively.The fresh roots and rhizomes of C.wenyujin were found to have the similarvolatile components.The contents of these components were calibrated by the response of β-elemene.In addition,the principal active component,β-elemene,was further confirmed and relatively quantified by its standard.γ-terpinene showed obvious allylic hydrogen/deuterium exchange using deuterium oxide which gave a new methodto identify some compounds containing allylic hydrogen.At the same time,the active hydrogen compounds werealso further confirmed.The results show that HS-GC-MS method is a fast,simple and efficient way for the analysisof volatile components from medical plants.     

气相色谱/质谱法分析曼陀罗果实挥发油的化学成分

用水蒸汽蒸馏法从曼陀罗果实中提取挥发油,并用气相色谱/质谱(GC/MS)联用技术对其化学成分进行分离和结构鉴定,用峰面积归一化法确定各成分的相对含量。结果确定了68种化合物,占挥发油总量的82.83%,其主要成分为6-戊基-5,6-二氢化吡喃-2-酮(9.13%)、3,7,11,15-四甲基-2-十六碳烯-1-醇(6.71%)、二苯酮(6.16%)和1-己醇(6.10%)等。     

A unique urinary constituent, 6-hydroxy-6-methyl-3-heptanone, is a pheromone that accelerates puberty in female mice.

BACKGROUND: Olfactorily mediated puberty acceleration in female mice (measured by an increase in uterine weight) has been observed since the 1960s without the active chemosignal being structurally identified. There are many controversies in the literature as to whether this male-originated pheromone is a volatile substance. We investigated the chemical nature of the urinary fractions that are responsible for the characteristic uterine weight increases. RESULTS: The active pheromone was identified as 5,5-dimethyl-2-ethyltetrahydrofuran-2-ol and/or its open-chain tautomer (6-hydroxy-6-methyl-3-heptanone). A series of cyclic vinyl ethers were isolated from chromatographically active fractions of the urine. Because these compounds did not accelerate puberty, we postulated that these ethers were degradation products of a lactol (5,5-dimethyl-2-ethyltetrahydrofuran-2-ol). The lactol was then detected directly in the mouse urine extract using a silylation agent. Synthetic 6-hydroxy-6-methyl-3-heptanone had strong biological activity, whereas its close structural analogs did not. CONCLUSIONS: The male house mouse excretes into its urine a large quantity of a volatile substance that has a unique lactol/hydroxyketone structure. This substance is capable of binding to the less volatile urinary constituents, such as proteins or peptides, and is active in puberty-acceleration bioassays. The controversies regarding the volatility of the puberty-accelerating pheromones can now be explained by considering a complex of volatile lactol/hydroxyketone and urinary proteins.     

黄荆子挥发性成分的分析

分别采用水蒸汽蒸馏法和超临界流体CO2萃取法提取黄荆子中的挥发性成分.利用气相色谱-质谱(GC/MS)联用技术对其化学成分进行了分析鉴定,并通过面积归一法测定了各成分的相对含量.对两种提取方法的结果进行了比较.结果表明,子午岭的黄荆子中含有多种药用成分,而超临界流体CO2萃取法更能有效地提取黄荆子中的有效成分.     

黑胡椒根萜类化合物的分析

报道了用蒸馏 萃取法提取黑胡椒根中挥发性物质,测得黑胡椒根挥发油的质量分数为3.1%,用GC/MS法从黑胡椒根挥发油中分离并确定出28种化学成分。其中主要成分为萜类化合物,占总检出量的82.48%。