Effects of Thai Local Ingredient Odorants,Litsea cubeba and Garlic Essential Oils,on Brainwaves and Moods

The functional food market is growing with a compound annual growth rate of 7.9%. Thai food recipes use several kinds of herbs. Lemongrass, garlic, and turmeric are ingredients used in Thai curry paste. Essential oils released in the preparation step create the flavor and fragrance of the famous tom yum and massaman dishes. While the biological activities of these ingredients have been investigated, including the antioxidant, anti-inflammatory, and antimicrobial activities, there is still a lack of understanding regarding the responses to the essential oils of these plants. To investigate the effects of essential oil inhalation on the brain and mood responses, electroencephalography was carried out during the non-task resting state, and self-assessment of the mood state was performed. The essential oils were prepared in several dilutions in the range of the supra-threshold level. The results show that Litsea cubeba oil inhalation showed a sedative effect, observed from alpha and beta wave power reductions. The frontal and temporal regions of the brain were involved in the wave alterations. Garlic oil increased the alpha wave power at lower concentrations; however, a sedative effect was also observed at higher concentrations. Lower dilution oil induced changes in the fast alpha activity in the frontal region. The alpha and beta wave powers were decreased with higher dilution oils, particularly in the temporal, parietal, and occipital regions. Both Litsea cubeba and turmeric oils resulted in better positive moods than garlic oil. Garlic oil caused more negative moods than the others. The psychophysiological activities and the related brain functions require further investigation. The knowledge obtained from this study may be used to design functional food products.     

An Overview on Total Valorization of Litsea cubeba as a New Woody Oil Plant Resource toward a Zero-Waste Biorefinery

With the increasing global demand for edible oils and the restriction of arable land minimum in China, woody oil plants have gradually become the optimal solution to cover the shortage of current edible oil supply and to further improve the self-sufficiency rate. However, due to the lack of knowledge and technique, problems like “how to make full use of these plant resources?” and “how to guide consumers with reasonable data?” limit the development of woody oilseed industry towards a sustainable circular economy. In this review, several emerging unique woody oil plants in China were introduced, among which Litsea cubeba as a new woody oil plant was highlighted as a reference case based on its current research progress. Unlike other woody oil plants, essential oil rather than oil from Litsea cubeba has always been the main product through the years due to its interesting biological activities. Most importantly, its major component, citral, could be the base for other synthesized perfume compounds with added value. Moreover, the sustainable biorefinery of large amounts of waste residual after Litsea cubeba essential oil processing is now technically feasible, which could inspire a total valorization pathway for other woody oil plants to make more competitive plant-based products with both economic, social, and ecological benefits.     

Flavonoid Composition in the Leaves of Twelve Litsea and Neolitsea Plants

This study was aimed to study the chemodiversity of flavonoids in the Formosan Litsea and Neolitsea plants. Applications of LC‐SPE‐NMR and LC/MS hyphenated techniques in analyzing polar constituents from the leaves of L. acuminata, L. hypophaea, N. acuminatissima, and N. konishii led to the identification of 13 known flavonoids and one new flavonol dioside, quercetin 3‐O‐(2‐O‐β‐D ‐apiofuranosyl)‐α‐L ‐rhamnopyranoside. The quantity and variety of flavonoid composition in the leaves of 12 Litsea and Neolitsea plants were examined to enable more effective utilization of such bioactive ingredients. Of these, N. acuminatissima was found to contain the most quantity of flavonoids (ca. 0.24%leaves).     

Chemical Constituents from the Leaves of Litsea Acutivena

Continuous investigation of the CHCl₃‐soluble and n‐hexane fractions of the leaves of Litsea acutivena Hayata (Lauraceae) led to the isolation of one new butanolide, acutilactone ( 1 ), one new lactone, 4‐nonacosyl‐dihydrofuran‐2‐one ( 2 ), together with 15 known compounds. The known compounds included one butanolide, one norisoprenoid, one quinone, two steroids, one triterpenoid, one coumarin, two fatty acids, one amide, and five other compounds. The structures of these compounds were determined by means of spectral analyses.     

Authenticity control of essential oils containing citronellal and citral by chiral and stable-isotope gas-chromatographic analysis

Enantioselective capillary GC on a Supelco β-DEX 225 column (heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin SPB 20poly—20% diphenyl, 80% dimethylsiloxane) and isotope-ratio mass spectrometry, coupled online with capillary GC on an HP5 column have been used for origin-specific analysis and authenticity control of essential oils, for example lemon (Citrus limon), lemongrass (Cymbopogon citratus and Cymbopogon flexuosus), citronella (Cymbopogon nardus L.—Ceylon type and Cymbopogon winterianus—Java type), Litsea cubeba, Lippia citriodora, lemon myrtle (Backhousia citriodora), lemon gum (Eucalyptus citriodora), and, especially, precious lemon balm oil (Melissa officinalis L.). Isotope data (δ¹³C_PDB and δ²H_V-SMOW) for citral (neral + geranial) and citronellal from on-line GC–C/Py–IRMS and chiral data for citronellal in these essential oils are reported. The possibility of using these data to determine the origin of these essential oils and to detect adulteration is discussed. Principal-components analysis (PCA) of specific compounds in two essential oils of lemongrass and Litsea cubeba was performed as a practical statistical method for distinguishing between these two types of oil.     

Stonebrood and chalkbrood in Apis mellifera causing fungi: in vitro sensitivity to some essential oils

Aim of the present study was to evaluate the in vitro antimycotic activity of 17 chemically defined essential oils (EOs) both alone and as a mixture, against agents responsible for stonebrood caused by Aspergillus flavus, and chalkbrood caused by Ascosphaera apis in European honeybees. Cinnamomum zeylanicum yielded the lowest MIC value against A. flavus, but was not effective against A. apis, while Litsea cubeba and Pelargonium graveolens appeared to be effective against all checked fungi. Aspergillus niger showed the lower sensitivity. Two mixtures composed by L. cubeba, C. zeylanicum and Cymbopogon flexuosus (M1) and by L. cubeba, C. zeylanicum, P. graveolens and C. flexuosus (M2), respectively, were tested, both resulting effective. The components of M1 showed a synergistic effect. The use of mixtures allowed to decrease the total amount of EOs. The use of these products could be of interest for an alternative natural approach in honeybee disease management.     

Litseaglutinan A and Lignans from Litsea glutinosa

A new abscisic acid derivative, named litseaglutinan A ( 1 ), and a new arylnaphthalene‐type lignan, (7′S,8R,8′S)‐4,4′,9‐trihydroxy‐3,3′,5‐trimethoxy‐9′‐O‐β‐D ‐xylopyranosyl‐2,7′‐cyclolignan ( 2 ), were isolated from the AcOEt extract of Litsea glutinosa, together with nine known lignans. Their structures were established by spectroscopic methods.     

Secondary Metabolites from the Leaves of Litsea lii var. nunkao‐tahangensis

Investigation of the leaves extract of Litsea lii var. nunkao‐tahangensis led to the isolation of five new butanolides, litsealiicolide A ( 1 ), isolitsealiicolide A ( 2 ), litsealiicolide B ( 3 ), isolitsealiicolide B ( 4 ), and isolitsealiicolide C ( 5 ), along with 17 known compounds. Their structures were determined through in‐depth spectroscopic and mass‐spectrometric analyses. Among the isolates, compounds 1 and 2 were cytotoxic against MCF‐7, NCI‐H460, and SF‐268 cell lines in vitro. Compound 5 and isolinderanolide B ( 6 ) showed marginal cytotoxic activity against these three cell lines in vitro.     

Secondary Metabolites from the Stem Bark of Litsea akoensis and Their Cytotoxic Activity

Six new butanolides, litseadioxanins A and B ( 1 and 2 , resp.) bearing a 1,2‐dioxane moiety, litseatrinolides A and B ( 3 and 4 , resp.), and litseakolides D₁ and D₂ ( 5 and 6 , resp.), were isolated from the stem bark of Litsea akoensis, together with six known compounds. The structures of the new compounds were characterized by in‐depth NMR‐spectroscopic and mass‐spectrometric analyses. Butanolides 1 – 4 , and a mixture of 6 and litsenolide E₂, and litsenolide B₁ were tested against human tumor cells, including MCF‐7 (human breast adenocarcinoma), NCI‐H460 (non‐small‐cell lung cancer), and SF‐268 (glioblastoma) cell lines. Among the tested compounds, litsenolide B₁ exhibited marginal cytotoxic activity against MCF‐7, NCI‐H460, and SF‐268 cell lines in vitro.     

Characterization and simultaneous quantification of biological aporphine alkaloids in Litsea cubeba by HPLC with hybrid ion trap time‐of‐flight mass spectrometry and HPLC with diode array detection

The root and rhizome of Litsea cubeba (Lour) Pers., named ‘Dou‐chi‐jiang’ in Chinese, has been traditionally used for treatment of cardiovascular and cerebrovascular diseases, rheumatic arthralgia, and other diseases in China. Aporphine alkaloids are its characteristic ingredients and responsible for its bioactivities, especially anti‐inflammatory and analgesic effects. A sensitive and reliable high‐performance liquid chromatography with diode array detection‐tandem mass spectrometry method was developed for characterization and simultaneous determination of biological aporphine alkaloids in ‘Dou‐chi‐jiang’. The optimized chromatographic conditions were performed on an Eclipse XDB C₁₈ column with a gradient of acetonitrile/water containing 0.1% formic acid as the mass spectrometry mobile phase and acetonitrile/water containing 0.2% diethylamine (pH 3.10, adjusted by acetic acid) as the liquid chromatography mobile phase. The fragmentation pathways by loss of CO, ·CH₃, ·NH₃, and ·NH₂CH₃ were detected as characteristic for aporphine alkaloids. Based on these characteristics, total 12 analogues were identified. The quantification method was validated in terms of linearity, precision, and accuracy for six major aporphine alkaloids, which was successfully applied for simultaneous determination in ten batches of samples. The established method is simple, rapid, and specific for characterization and quantitation of aporphine alkaloids in ‘Dou‐chi‐jiang’ and other traditional Chinese medicines rich in this kind of ingredient.     

Composition and antimicrobial activity of the leaf and twig oils of Litsea mushaensis and L. linii from Taiwan

The hydrodistilled essential oils of the leaves and twigs of Litsea mushaensis and L. linii were analyzed. Sixty-nine and ninety compounds were identified in the leaf and twig oils, respectively, of L. mushaensis. The main components of the leaf oil were beta-eudesmol (24.2%), tau-cadinol (10.2%), alpha-humulene (10.1%), alpha-pinene (9.7%), and trans-beta-ocimene (6.5%), whereas the main components of the twig oil were trans-beta-ocimene (19.5%), alpha-pinene (12.8%) and cis-beta-ocimene (7.7%). With L. linii, 72 and 78 compounds were respectively identified in the leaf and twig oils. The main components of the leaf oil were beta-selinene (15.7%), alpha-selinene (15.5%), beta-caryophyllene (12.2%), alpha-humulene (7.2%), and delta-cadinene (5.6%), and of the twig oil trans-beta-ocimene (20.8%), beta-selinene (11.4%), alpha-cadinol (6.0%), delta-cadinene (5.8%), tau-cadinol (5.4%) and beta-eudesmol (5.2%). L. mushaensis leaf oil was shown to have excellent antimicrobial and anti-wood-decay fungal activity, superior to the other oils.     

Additional Isoquinoline Alkaloids from Lltsea Cubeba

By combination of centrifugal partition chromatography (CPC) and common separation methods, seven additional known bases were isolated and characterized from the reinvestigation of L. cubeba besides three previously isolated bases- isocorydine (10), N-methyllaurotetanine (9), and boldine (2). They are laurolitsine (1), laurotetanine (3), isoboldine (4), norisocorydine (5), N-methyllindcarpine (7), isodomesticine (8), and glaziovine (6). Among these, compound 9 is the most abundant (7.5 × 10^?4) and will be modified for pharmacological tests. This work will be of value for chemotaxonomy.     

Two New Aporphine Alkaloids from Litsea glutinosa

Chemical examination of the BuOH extract of the leaves and twigs of Litsea glutinosa collected from Xishuangbanna resulted in the isolation of two new aporphine alkaloids, namely litseglutine A ( 1 ) and B ( 2 ), along with two known aporphine alkaloids, boldine ( 3 ) and laurolitsine ( 4 ). The structures of the new alkaloids have been elucidated on the basis of spectra analysis as 6‐demethyl‐9‐methoxy‐1,2‐(methylenedioxy)aporphin‐10‐ol (=6,7,7a,8‐tetrahydro‐10‐methoxy‐5H‐benzo[g]‐1,3‐benzodioxolo[6,5,4‐de]quinolin‐11‐ol; 1 ) and 1,10,11‐trimethoxyaporphin‐2‐ol (=5,6,6a,7‐tetrahydro‐1,10,11‐trimethoxy‐6‐methyl‐4H‐dibenzo[de,g]quinolin‐2‐ol; 2 ).     

Composition and antimicrobial activity of the leaf and twig oils of Litsea acutivena from Taiwan

The chemical composition, and antimicrobial and anti-wood-decay fungal activities of the essential oils isolated from the leaves and twigs of Litsea acutivena of Taiwan were investigated. The essential oils from the fresh leaves and twigs were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Ninety-five and fifty-two compounds were identified in the leaf and twig oils, respectively. The main components of the leaf oil were gamma-patchoulene (11.0%), delta-cadinene (6.3%), trans-muurola-3,5-diene (5.9%), and beta-selinene (5.3%), whereas the main components of the twig oil were tau-cadinol (13.1%), beta-selinene (9.6%), trans-beta-ocimene (6.2%) and alpha-cadinol (7.7%). Bioactivity studies demonstrated that twig oil had excellent antimicrobial and anti-wood-decay fungal activities, superior to those of the leaf oil. For the antimicrobial and anti-wood-decay fungal activities of the twig oil, the active compounds were determined to be tau-cadinol and alpha-cadinol.     

Chemical composition of essential oils of Litsea cubeba harvested from its distribution areas in China

Litsea cubeba (Lour.) Pers. is a promising industrial crop with fruits rich in essential oils. The chemical composition of essential oils of L. cubeba (EOLC) were determined for fruits harvested from eight regions in China. The overall essential oil content, obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS), ranged from 3.04% to 4.56%. In total, 59 compounds were identified, the dominant components being monoterpenes (94.4-98.4%), represented mainly by neral and geranial (78.7-87.4%). D-Limonene was unexpectedly a lesser constituent (0.7-5.3%) in fruits, which differed from previous reports (6.0-14.6%). Several components were only detected in certain regions and compounds such as o-cymene and eremophilene have never before been reported in EOLC. These results demonstrate significant regional variation in the chemical composition of EOLC. This investigation provides important information with regard to the bioactivity, breeding work and industrial applications of L. cubeba.     

Composition, antioxidant and antimicrobial activities of leaf and twig essential oils of Litsea akoensis from Taiwan

This study analyzed the hydrodistilled essential oils in the leaves and twigs of Litsea akoensis to determine composition and yield. Seventy-one and 40 compounds were identified in the leaf and twig oils, respectively. The main components of leaf oil were limonene (18.5%), thymol (10.1%), p-cymene (9.6%), beta-caryophyllene (8.9%), and carvacrol (8.2%). The main components of twig oil were beta-phellandrene (43.7%) and trans-beta-ocimene (10.4%). The results demonstrated that leaf oil had excellent antioxidant and antimicrobial activities, superior to those of twig oil.     

Chemical composition and variability of the volatile components from inflorescences of Cirsium species

The present study aimed to investigate the chemical composition of the essential oils of inflorescences Cirsium spp. (Asteraceae) by GC/MS method. Essential oils were extracted from the inflorescences of Cirsium pannonicum (Link), Cirsium ligulare Boiss., Cirsium heterophyllum (L.) Hill., Cirsium acaule (L.) Scop., Cirsium oleraceum (L.) Scop., Cirsium dissectum (L.) Hill., Cirsium decussatum (Janka) and Cirsium eriophorum (L.) Scop., using the steam distillation method. A gas chromatography–mass spectrometry method was employed for the analysis of essential oils. Our study shows the differences in chemical composition of volatile oils in the inflorescences of Cirsium spp. The main components of the essential oil were ketones and aldehydes with a long carbon side-chain. Volatile oils also contained small amounts of terpenes: thymol, β-linalool, eugenol, carvacrol and fatty acids with odd number of carbon atoms–waxes. The compounds in the essential oils obtained from inflorescences Cirsium L. species have been identified for the first time.     

Reporting effective extraction methodology and chemical characterization of bioactive components of under explored Platycladus orientalis (L.) Franco from semi-arid climate

The bioactive ingredients of many essential oils are complex and difficult to reproduce synthetically. In the present study, the influence of extraction method on relative extraction of bioactive compounds of essential oil of Platycladus orientalis (L.) Franco (Thuja orientalis L. is a synonym of it) leaves gathered from semi-arid climate was studied. A higher yield of essential oil was obtained by hydrodistillation (0.1%) as compared to steam distillation (0.07%) under newly optimized conditions. Initial analysis of these oils by TLC showed the presence of different polarity groups ranging from non-polar terpene hydrocarbons to polar terpenoid alcohols. GC-MS analysis revealed that major component of hydrodistilled essential oil of Platycladus orientalis (L.) Franco leaves was α-pinene (17.83%) and steam distilled essential oil contained α-cedrol (12.44%). The results obtained in the present study emphasize that suitable extraction technique should be used to obtain particular component of interest.     

Essential oils of the leaves of grafts ofCitrus unshiu

The compositions of the essential oils obtained by steam distillation from the leaves of frost-resistant stocks of trifoliate orange (P. trifoliata (L.) Raf.) and Yunos-Yuzu citrus (Citrus ionos (Sieb.) and grafts of the mandarin orangeC. unshiu Marc —P. trifoliata +C. unshiu andC. ionos +C. unshiu — have been investigated with the aid of vacuum distillation, GLC, chromatography on an alumina column, and IR spectroscopy. The leaves were collected in the period of the flowering of the plants. The essential oils of grafts of the unshiu mandarin on trifoliate orange and Yunos-Yuzu citrus differed from one another with respect to the amounts of the components.Institute of Plant Biochemistry, Academy of Sciences of the Georgian SSR, Tbilisi, Batumi Botanical Garden, Academy of Sciences of the Georgian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 607–610, September–October, 1984.     

Effectiveness of the Influence of Selected Essential Oils on the Growth of Parasitic Fusarium Isolated from Wheat Kernels from Central Europe

The aim of the study was to determine the effectiveness of selected seven commercial essential oils (EsO) (grapefruit, lemongrass, tea tree (TTO), thyme, verbena, cajeput, and Litsea cubeba) on isolates of common Central European parasitic fungal species of Fusarium obtained from infected wheat kernels, and to evaluate the oils as potential natural fungicides. The study was conducted in 2 stages. At each stage, the fungicidal activity of EsO (with concentrations of 0.025; 0.05; 0.125; 0.25; 0.50; 1.0, and 2.0%) against Fusarium spp. was evaluated using the disc plate method and zones of growth inhibition were measured. At the first stage, the fungistatic activity of EsO was evaluated against four species of Fusarium from the Polish population (F. avenaceum FAPL, F. culmorum FCPL, F. graminearum FGPL and F. oxysporum FOPL). The correlation coefficient between the mycelial growth rate index (T) and the fungistatic activity (FA) was calculated. At the second stage, on the basis of the mycelium growth rate index, the effectiveness of the EsO in limiting the development of Fusarium isolates from the German population (F. culmorum FC1D, F. culmorum FC2D, F. graminearum FG1D, F. graminearum FG2D and F. poae FP0D) was assessed. The first and second stage results presented as a growth rate index were then used to indicate essential oils (as potential natural fungicides) effectively limiting the development of various common Central European parasitic species Fusarium spp. Finally, the sensitivity of four Fusarium isolates from the Polish population and five Fusarium isolates from the German population was compared. The data were compiled in STATISTICA 13.0 (StatSoft, Inc, CA, USA) at the significance level of 0.05. Fusarium isolates from the German population were generally more sensitive than those from the Polish population. The sensitivity of individual Fusarium species varied. Their vulnerability, regardless of the isolate origin, in order from the most to the least sensitive, is as follows: F. culmorum, F. graminearum, F. poae, F. avenaceum and F. oxysporum. The strongest fungicidal activity, similar to Funaben T, showed thyme oil (regardless of the concentration). Performance of citral oils (lemongrass and Litsea cubeba) was similar but at a concentration above 0.025%.