Steam Distillation-solvent Extraction Research Articles

Comparative chemical profiling of leaf essential oils from Cinnamomum kanehirae and related species using steam distillation and solvent extraction: Implications for plant-based classification

Cinnamomum kanehirae Hayata, belonging to Lauraceae family, is an indigenous and endangered species of considerable economic importance in Taiwan. It plays a crucial role as the host for the economically valuable saprotrophic fungus, Taiwanofungus camphorates. However, accurate species identification poses a challenge due to the similarity in morphological features and frequent natural hybridization with closely related species. Acquiring high-quality and pure leaf oils becomes imperative for precise species identification and producing superior goods. In this study, our objective was to establish methodologies for analyzing the chemical composition of leaf essential oils and subsequently apply this knowledge to differentiate among three Cinnamomum species. Gas chromatography-mass spectrometry (GC/MS) was employed to scrutinize the chemical makeup of leaf essential oils from three closely related species: C. kanehirae, C. micranthum, and C. camphora. We utilized Steam Distillation (SD) and steam distillation-solvent extraction (SDSE) methods, with the SDSE-Hexane approach chosen for optimization, enhancing extraction efficiency and ensuring essential oil purity. Through the SDSE-Hexane method, we identified seventy-four compounds distributed across three major classes: monoterpenes hydrocarbons (0.0–7.0 %), oxygenated monoterpenes (3.8–90.9 %), sesquiterpenes hydrocarbons (0.0–28.3 %), and oxygenated sesquiterpenes (1.6–88.1 %). Our findings indicated the presence of more than one chemotype in both C. kanehirae and C. camphora, whereas no specific chemotype could be discerned in C. micranthum. Furthermore, clustering based on chemotypes allowed for the differentiation of samples from the three species. Notably, we demonstrated that the chemical compositions of grafted C. kanehirae remained largely unaffected by the rootstock. Conversely, natural hybrids between C. kanehirae and C. camphora exhibited profiles more closely aligned with C. kanehirae. The optimized extraction method and the chemotype-based classification system established in this study present valuable tools for essential oil preparation, species identification, and further exploration into the genetic variation of Cinnamomum.

Physicochemical and sensory (aroma and colour) characterisation of a non-centrifugal cane sugar ("panela") beverage.

Non-centrifugal cane sugar (NCS), also called "panela", is a high carbohydrate-content food obtained by boil evaporation of the sugar cane juice. This study was undertaken to assess physicochemical properties and sensory characteristics of panela beverage at two different concentrations. Evaluation of pH, °Brix, and colour (tristimulus colorimetry) was carried out in all panela drink samples. In order to characterise the odour-active volatiles of the beverage, a simultaneous steam distillation-solvent extraction method was applied using a mixture of diethyl ether-pentane (1:1,w/w) as solvent. The Aroma Extract Dilution Analysis revealed the presence of six odour-active compounds, being 2-methyl pyrazine the key aroma compound of this beverage. PCA (Principal Component Analysis) showed that there were no differences in the aroma and physicochemical properties (pH and °Brix) with respect to the geographical origin of analysed samples; however colour depends on heating during processing of NCS.

Relationship between fruit ripening and aroma compounds of olives from Guercif area in Morocco

Green olives are characterized by a typical flavour mainly due to compounds formed during fruit ripening. Our previous studies have shown that the (Z)-3-hexenal, methional, guaiacol, (E,E)-2,4-decadienal and other terpenes such as α-farnesene significantly contribute to the olive aroma. In the present study, the impact of ripening stage on the aromatic composition of the green olives in Guercif area was evaluated. The extraction of flavours from samples collected at different stages of maturation was performed by simultaneous steam distillation-solvent extraction. The extracts were analyzed by GC-MS and GC-FID-O. The results showed that proportions of odorant compounds with sensory impact on the Moroccan green olives such as (Z)-3-hexenal/hexanal and methional, increased during fruit ripening. The olive fruit sam-ples from area of Guercif were characterized by the dominance of mono-and sesquiterpenes such as γ-terpinene, 3-carene, α-pinene, limonene, 3,7-dimethyl-1,3,7-octatriene, α-farnesene, β-caryophyllene and α-humulene. The monitoring of the aroma composition during olive ripening stage showed that the proportion of the 3,7-dimethyl-1,3,7-octatriene strongly decreases during maturation while the proportions of other monoterpenes characterized by olfactory notes of lemon, green and floral such as γ-terpinene, 3-carene and α-pinene are more important in the final stage of maturation. For the sesquiterpenes class, the formation of β-caryophyllene and α-humulene decreases in favour of the α-farnesene, important aroma compound of table olives. The comparison of volatile fraction of fresh olives at different stages of maturation showed that fruit ripening has an important impact on the formation of aromatic compounds and particularly the key flavours of green olives.

Comparative Study of Antioxidant Activity of Extracts and Essential Oils Composition of Artemisia absinthium L. Prepared by Two Different Methods

In this study, chemical compositions of the essential oils isolated from aerial parts of Artemisia absinthium L. by hydrodistillation (HD) and simultaneous steam distillation-solvent extraction (SDE) methods were compared quantitatively and qualitatively using GC-FID and GC-MS. β-Pinene, β-thujone and o-cymene were the major constituents in both cases but in different amounts. Antioxidant activities of various extracts from A. absinthuim were evaluated via DPPH radical scavenging, total phenolic content of the extracts were also evaluated using folin-ciocalteo reagent. Results reveal that although phenolic contents are not high significantly in this plant, water and ethanol extracts of this plant has considerable radical scavenging activity.

Characterisation of volatile compounds in a smoke flavouring from rice husk

An aqueous smoke flavouring from rice husk was obtained on a laboratory scale. The volatile compounds were isolated by simultaneous steam distillation–solvent extraction and its identification and quantitative composition was studied by GC–MS and GC–FID. A total of 93 compounds were isolated and 86 of them were positively identified. Major compounds (more than 5% GC area) were 2-furfural, phenol, 2-methoxyphenol, 4-ethyl-2-methoxyphenol, and 2,6-dimethoxyphenol. Application of aroma extract dilution analysis on the volatile fraction revealed that 2-methoxyphenol, 4-methyl-2-methoxyphenol, 2,6-dimethoxyphenol, 2-furfural, 2-acetylfuran, 3-methyl-1,2-cyclopentanedione, acetic acid, 5-methyl-2-furfural, 4-(2-propenyl)-2-methoxyphenol, 4-methyl-2,6-dimethoxyphenol, phenol, 2,6-dimethylphenol, 4-ethyl-2-methoxyphenol, 2-methylphenol were the most odour-active compounds.

Improved Method for the Extraction and Determination of Bromophenols in Seafoods by High-Performance Liquid Chromatography with Fluorescence Detection

A sensitive precolumn derivatization method using 10-methylacridone-2-sulfonyl chloride (MASC) as derivatizing reagent followed by high-performance liquid chromatography (HPLC) with fluorescence detection has been developed for the determination of naturally occurring bromophenols in seafoods. Instead of using a traditional complex steam distillation solvent extraction method, the extraction method was modified by using sulfuric acid hydrolysis followed by hexane extraction and subsequent alkaline back extraction to obtain good recoveries and fewer interferences. Batch analysis of bromophenols thus became more performable because the sample amount and analysis time were greatly reduced. The recoveries of the five bromophenols were >80% with a noticeable improvement for 4-BP, the recoveries of which were usually <40% when analyzed by traditional methods. The HPLC sensitivity for the determination of bromophenols was greatly enhanced through derivatization. Under optimal conditions, the quantification limits obtained by using 4.0 g of sample were in the range of 0.60-1.0 ng/g. This is the first time that derivatization was applied to enhance the HPLC sensitivity of bromophenols. The proposed method was successfully applied to the determination of the target compounds in seafoods with a much higher sensitivity than traditional HPLC method.

Fast Quality Assessment of German Chamomile (Matricaria chamomilla L.) by Headspace Solid-Phase Microextraction: Influence of Flower Development Stage

For an adequate quality evaluation of aromatic plants grown under different conditions, a rapid, simple and sensitive method for the analysis of volatile constituents is indispensable. The main objective of the present study was to compare fast screening of German chamomile (Matricaria chamomilla L.) by means of headspace solid-phase microextraction (HS-SPME) with conventional isolation of the essential oil (steam distillation-solvent extraction (SDSE)) for the differentiation of chamomile essential oil constituents. Flowers were harvested at two distinct development stages: stage I, when ligulate flowers start to develop and tubular flowers are still closed, and stage II, when tubular flowers are partially to completely opened. Dried chamomile flowers at two development stages were extracted by means of both SDSE and HS-SPME, followed by GC-MS analysis. Among 30 compounds detected, (E)-beta-farnesene (49%), artemisia ketone (10%) and germacrene D (9%) were the predominant volatile components in the HS-SPME-extract, while alpha-bisabolol oxide A (42%), chamazulene (21%) and (Z)-spiroether (8%) were the main essential oil constituents among the 13 compounds obtained by SDSE. After statistical analysis of the data, both techniques enabled the same conclusion: (E)-beta-farnesene was the only compound which showed significant differences between the two flower development stages. These results suggest that HS-SPME-GC-MS can be used as a sensitive technique for the rapid screening and quality assessment of M. chamomilla.

Comparative study of composition and biological activities of SDE prepared essential oils from flowers and fruits of two Hypericum species from central Iran

Essential oil (EO) compositions of flowers and fruits of Hypericum perforatum L. and Hypericum scabrum L. growing wild in Kashan, central Iran, were determined by simultaneous steam distillation-solvent extraction method and analysed using GC–MS technique. Analysis revealed 28 identified compounds for H. perforatum, with two main components being α-pinene (25.36%) and α-amorphene (12.12%). Thirty-five compounds were identified in H. scabrum L. representing 98.60% of the oil with α-pinene (70.21%) and p-mentha-1,5-dien-8-ol (2.89%) as main components. Some new compounds were found in significant quantities which were not found in other chemotypes. The antioxidant activities of the EOs evaluated for the first time in this study using β-carotene bleaching and DPPH assays seemed to be attributed directly to α-pinene contents in them. Antibacterial activities of both mentioned EOs were higher than that of their main constituent, α-pinene, against Staphylococcus aureus and Escherichia coli.

Identification of characteristic aroma-active compounds in steamed mangrove crab (Scylla serrata)

Mangrove crab (Scylla serrata) has delicate texture and flavor, high economic value, and is relatively easy to grow. With its total production reaching 177 million kg in 2008, mangrove crab has become one of the most important marine commercial crustaceans in China. The objective of this study was to evaluate the potent aroma-active compounds in steamed mangrove crab. Odorants of steamed crabmeat extracted by simultaneous steam distillation–solvent extraction were investigated by MS hyphenated to the GC–Olfactometry system with two olfactometric methods: detection frequency method and aroma extract dilution analysis. A total of 53 compounds were identified in steamed mangrove crab meat. 38 aroma-active components were further detected and 31 identified. The following 5 were the most important contributors to the aroma of steamed mangrove crab meat: 2,3-butanedione (creamy, caramel), 2,5-dimethylpyrazine (roasted, nutty), 3-methylbutanal (chocolate), 2-acetyl-1-pyrroline (popcorn, nutty), 2-acetylthiazole(roasted, sulfury).

Determination of best harvest time of German chamomile (Matricaria chamomilla L.) flowers based on solid-phase microextraction-GC-MS analysis data

Solid-phase microextraction (SPME) technique is a relatively simple, rapid, inexpensive and solvent-free sampling technique for the determination of volatiles in plant essential oils when compared to conventional sampling techniques like steam distillation solvent extraction (SDSE). Moreover, newer SPME can be automated and does not lead to thermal degradation of chemical components [1,2]. In order to determine best harvest times in terms of quality of chamomile (Matricaria chamomilla L.) grown in Belgium, SPME was applied. On April 15, 2005, 90 day old seedlings were transplanted into the field. At harvest, flowers were divided in two groups on the basis of development stage [3]. Stage I flowers corresponded to initial up to full development of the ligulate flowers, while tubular flowers were closed. Flowers were categorized as stage II when tubular flowers were partially (first circle) up to completely open. After drying, flower heads were analyzed by headspace SPME-GC-MS. Six marker compounds, i.e. (E)-β-farnesene, α-bisabolol oxide A and B, α-bisabolone oxide, (Z)-spiroether and spathulenol were identified and quantities compared statistically for the two different stages of flower development based on their GC peak area. Results indicate that most of the measured traits were not significantly influenced by the stage of development, except for (E)-β-farnesene. The peak area of this compound in stage I was significantly higher than in stage II. These results are in agreement with previous results obtained by SDSE. Therefore, SPME-GC-MS analysis is proposed to be a suitable technique for the differentiation in quality of chamomile flower development stages.

Volatile Compounds of the Fruits of Sipharuna thecaphora (Poepp. et Endl.) A. DC.

Volatile compounds were isolated from fruits of Siparuna thecaphora (Poepp. et Endl.) A. DC. by simultaneous steam distillation-solvent extraction. Compounds were identified by capillary GC/MS. One hundred and thirty compounds were identified, with the major representatives being atractylone (12.7% of the total volatiles) and curzerene (11.7% of the total volatiles). The significant amounts of neral and geranial, with their powerful lemon fragrances, contribute much to the typical fruit flavor.

Volatile Compounds Collected by Simultaneous Steam Distillation-Solvent Extraction from Hong Kong Salt-Dried Croakers

We compared the quality and quantity of volatile components in salt-dried croakers prepared by different methods and obtained from different locations. In total, 110 compounds were found among regular- and delay-type salt-dried croakers purchased from two locations in Hong Kong. The major chemical classes included miscellaneous compounds(17), pyrazines(16), alcohols(15), and sulfur-containing compounds(13). Fish obtained in different locations but prepared by the same method differed only slightly in the number of identified compounds. In general, fish prepared by the delay method had a larger number of compounds compared to fish prepared by the regular method. Further, a greater number and higher levels of compounds were found in the fish obtained from one of the two locations. Overall, the delay preparation method resulted in a greater number of compounds with stronger intensity compared to the regular method.

Roasted Chicory Aroma Evaluation by Gas Chromatography/Mass Spectrometry/Olfactometry

Volatiles were isolated from roasted chicory by simultaneous steam distillation-solvent extraction (SDE) and dynamic headspace sampling (DHS). Many volatile components were identified in SDE (92) and DHS (64) extracts. Many pyrazines and N-furfurylpyrroles (N-furfurylpyrrole, N-furfuryl-2-formylpyrrole, and N-furfuryl-2-acetylpyrrole) were identified for the first time in roasted chicory. Aroma extract dilution analysis showed that those extracts from SDE and DHS were similar with respect to predominant aroma-active components. 2-Ethyl-3,5-dimethylpyrazine, 2,3-butanedione, 1-octen-3-one, 3-methylbutanal, and one unknown compound with a chicory- and burnt sugar-like note were the most intense aroma-active components found in roasted chicory.

Solid phase microextraction as a methodology in the detection of irradiation markers in ground beef

The usefulness of solid phase microextraction (SPME) to detect the occurrence of the irradiation markers 2-dodecylcyclobutanone (2-DCB) and 1,3-bis(1,1-dimethylethyl)benzene in irradiated ground beef was evaluated. To that aim, beef samples were irradiated with different irradiation doses and subsequently examined together with non-irradiated beef samples used as control samples. The SPME conditions applied were selected as a result of performing an optimization process including different fibers (PDMS, DVB/CAR/PDMS, polyacrylate and PDMS/DVB), as well as extraction times (10, 25 and 40min) and temperatures (40 and 60°C). For comparison, 2-DCB and 1,3-bis(1,1-dimethylethyl)benzene were additionally identified in some of the samples by steam distillation–solvent extraction (SDE). Although this study is a preliminary work, from the results obtained SPME seemed to be a rapid and valuable technique to determine 2-DCB and 1,3-bis(1,1-dimethylethyl)benzene in ground beef subjected to irradiation, offering advantages over other methods reported in the literature. In addition, SPME allowed to confirm the validity of 2-DCB as an useful marker to distinguish non-irradiated from irradiated ground beef. On the contrary, the occurrence of 1,3-bis(1,1-dimethylethyl)benzene was however established in both types of samples by SPME and SDE.

Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata

To investigate the active ingredient in fruiting bodies and to produce it with cultured mycelium in Antrodia camphorata (BCRC 35398). The volatile components from the fruiting bodies, the liquid cultured broth of A. camphorata and Cinnamomum kanehirae wood were separately isolated by steam distillation-solvent extraction and identified by gas chromatography-mass spectrometry. In the fruiting bodies, a COX-2 inhibitor 2,4,5-trimethoxybenzaldehyde (TMBA) was found to be the most abundant constituent, but was totally absent in its cultured broth and its natural host, C. kanehirae wood. On feeding with the acid-digested sawdust of C. kanehirae wood or vanillin to the broth for culture, TMBA was produced in both cultured broths. The TMBA identified in fruiting bodies was an active ingredient whose functions consisted with the reported experiences of this mushroom. Feeding vanillin to culture broth could produce TMBA containing mycelium product like its fruiting bodies did. This study found an active ingredient in fruiting bodies of A. camphorata and elucidated this compound derived from digested sawdust of C. kanehirae wood. A feasible method was also developed to produce TMBA containing mycelium by feeding vanillin.

V-SDE와 SPME법에 의한 꽃게(Portunus trituberculatus)육의 휘발성 향기성분 비교

Volatile flavor compounds in meat of the blue crab Portunus trituberculatus were compared using vacuum simultaneous steam distillation-solvent extraction (V-SDE) and solid phase microextraction (SPME)/ gas chromatography (GC)/ mass selective detection (MSD) methods. A total of 100 volatile flavor compounds were identified by both methods: 77 by V-SDE and 59 by SPME. These compounds were composed of 17 aldehydes, 12 ketones, 19 alcohols, 5 esters, 4 sulfur-containing compounds, 6 nitrogen-containing compounds, 23 aromatic compounds, 6 hydrocarbons, 2 terpenes, and 6 miscellaneous compounds. Although more compounds were detected using V-SDE than using SPME, the levels of all groups detected, except esters, were higher using SPME than using V-SDE. In addition to trimethylamine, aldehydes, and aromatic compounds, the S- and N-containing compounds with low thresholds are thought to have positive roles for flavors in the meat of the blue crab.

Volatile Components of Sapote [Pouteria sapota (Jacq.) H. E. Moore et Stern] Fruit

Volatile compounds were isolated from sapote fruit by simultaneous steam distillation-solvent extraction according to Likens-Nickerson. Compounds were identified by capillary GC and GC/MS. Twenty-four components were identified in the aroma concentrate, from which benzaldehyde, hexanal and hexadecanoic acid were found to be the major constituents.

Determination of simple bromophenols in marine fishes by reverse-phase high performance liquid chromatography (RP-HPLC)

Brominated phenols 2- and 4-bromophenol (2-BP and 4-BP); 2,4- and 2,6-dibromophenol (2,4-DBP and 2,6-DBP) and 2,4,6-tribromophenol (2,4,6-TBP) have been identified as key flavor compounds found in seafoods. Depending on their concentrations, they were responsible for marine or ocean flavor (shrimp/crab/fish/sea salt-like) or for phenolic/iodine/iodoform-like off-flavor. In this work a new analytical methodology was developed to determine, simultaneously, such bromophenols in fish meats, based on reversed-phased high-performance liquid chromatographic separation (RP-HPLC). The separation of bromophenols was made onto a Lichrospher 100 RP-18 column using water:acetonitrile gradient at a flow rate of 1.0 mL min −1, using absorbance detection at 286 nm, were the 2-BP, 4-BP, 2,4- and 2,6-DBP show significant absorbtivity values and at 297 nm for 2,4,6-TBP. They were separated in 20 min with a good chromatographic resolution (Rs) for the isomeric compounds: 2- and 4-BP, Rs = 1.23; 2,4- and 2,6-DBP, Rs = 1.63. The calibration curves were linear in the bromophenols concentration range of 200.0–1000 ng mL −1. Under optimized conditions, the detection limit of the HPLC method was 127 ng mL −1 for 2-BP; 179 ng mL −1 for 4-BP; 89.0 ng mL −1 for 2,4-DBP; 269 ng mL −1 for 2,6-DBP and 232 ng mL −1 for 2,4,6-TBP. This method has been applied in determination of bromophenols, isolated by combined steam distillation-solvent extraction with 2 mL of pentane/diethyl ether (6:4), from Brazilian fishes samples, collected on the Atlantic coast of Bahia (13°01′S and 38°31′W), Brazil. The concentration range determined were 0.20 ng g −1 (2-BP) to 299 ng g −1 (2,4,6-TBP). The method proposed here is rapid and suitable for simultaneous quantification of simple bromophenols in fish meat. As long as we know, it is the first analytical methodology, using RP-HPLC/UV, which was developed to determine simple bromophenols in fish meat.

Volatile constituents of genipap (Genipa americana L.) fruit from Cuba

Volatile constituents were isolated from genipap (Genipa americana L.) fruit by simultaneous steam distillation–solvent extraction according to Likens–Nickerson. Compounds were identified by capillary GC-MS. Ninety-eight compounds were identified in the aroma concentrate, of which hexadecanoic acid, octadecanoic acid, tetradecanoic acid, linalool and limonene were found to be the major constituents. Carboxylic acids, with their acidic and harsh notes, should play an important role in the flavor of the fruit. Copyright © 2005 John Wiley & Sons, Ltd.

Evaluation of four isolation techniques for honey aroma compounds

AbstractThe analysis of the volatile fraction of honey provides useful information for the determination of the botanical and geographical origin. However, the results obtained vary greatly upon the extraction procedure employed. Four different isolation techniques were compared, that is hydrodistillation (HD), micro‐simultaneous steam distillation–solvent extraction (MSDE), ultrasound‐assisted extraction (USE) and solid‐phase microextraction (SPME). From the data obtained, USE and SPME seem to be more suitable for the isolation of potent marker compounds. HD and MSDE have main drawbacks because of the drastic conditions used that lead to the formation of artefacts and the degradation of sensitive compounds. These drawbacks are avoided when employing USE and SPME. Copyright © 2004 Society of Chemical Industry