Bornyl Acetate

Drying Induced Impact on Composition and Oil Quality of Rosemary Herb, Rosmarinus Officinalis Linn.[Pubmed:32575415]

Molecules. 2020 Jun 19;25(12). pii: molecules25122830.

The natural drying of Rosmarinus officinalis Linn. herbs severely affects its volatile oil quality and yields, which is reported here for the first time. The oils obtained through hydrodistillation from fresh, one, two, and three-weeks dried herbs were analyzed by gas chromatography-mass spectroscopy (GC-MS) and gas chromatography-flame ionization detector (GC-FID), and the yields were 198 +/- 3.45, 168.7 +/- 5.11, and 97.8 +/- 1.27 mg, respectively, as compared to the internal referral standard of 327 +/- 5.91 mg yield of the one-week dried herbs' oil. Camphor, the major constituent, significantly depleted from 20.96% to 13.84%, while Bornyl Acetate yields increased from 1.42% to 12.46% (p values < 0.0001) in three-weeks drying, reflecting the redox processes undergoing within the oil during drying. Several constituents (25) were found in one-week dried herbs' oil as compared to the fresh, two-, and three-weeks oils, which consisted of 23, 19, and 14 constituents, respectively, leading to the recommendation of the one-week drying of the herb for maximum oil yield. The DPPH (2, 2-diphenyl-1-picryl-hydrazyl) reactivity was highest for the two- and three-weeks dried herb-based oils, followed by the one-week dried- and fresh-herb-based oils (p < 0.0001), again indicating major chemical changes during herbs' dryings, affecting the free-radical scavenging capacity of these batches of oils obtained after different drying times.

GC-MS Analysis, Antioxidant and Antimicrobial Activities of Achillea Odorata Subsp. Pectinata and Ruta Montana Essential Oils and Their Potential Use as Food Preservatives.[Pubmed:32455872]

Foods. 2020 May 22;9(5). pii: foods9050668.

In order to discover new natural resources with biological properties, the chemical composition, the antioxidant and antimicrobial activities, and the potential use as food preservative of essential oils of Moroccan Achillea odorata subsp. pectinata (AOpEO) and Ruta montana (RMEO) were studied. Gas chromatography-mass spectrometry (GC-MS) analysis revealed the presence of 21 and 25 compounds in AOpEO and RMEO, respectively. The results showed that the major compounds of AOpEO are camphor (45.01%), Bornyl Acetate (15.07%), borneol (11.33%), beta-eudesmol (4.74%), camphene (3.58%), and 1.8-cineole (eucalyptol) (2.96%), whereas 2-undecanone (63.97%), camphor (3.82%) and cyclopropanecarboxylic acid (3.66%) were the main components of RMEO. The antioxidant activities were evaluated by diphenylpicrylhydraziyl radical (DPPH) and reducing power assays. The antimicrobial activities of essential oils were tested against bacterial strains and food contaminant yeast using agar disc diffusion and microdilution methods. A significant antimicrobial activity of AOpEO was observed against Bacillus subtilis, Proteus mirabilis and Candida albicans, compared to RMEO. The efficacy of AOpEO was also evaluated in model food systems (cabbage and barley) artificially inoculated during storage. The results found that the adding of a minimal inhibitory concentration (MIC) and 4x MIC were potent in decreasing the Proteus mirabilis growth in food model systems. Our findings suggested that AOpEO may be potentially used as an alternative food preservative.

Efficacy-directed discrimination of the essential oils of three Juniperus species based on their in-vitro antimicrobial and anti-inflammatory activities.[Pubmed:32439404]

J Ethnopharmacol. 2020 Sep 15;259:112971.

ETHNOPHARMACOLOGICAL RELEVANCE: Juniperus plants are considered important sources of cedar-wood oil which is used widely in folk medicine as antiseptic and in treatment of inflammatory disorders such as, rheumatoid arthritis but there is not enough scientific evidence to support the claimed uses and there is no specification of a certain Juniperus species as the most active. AIM OF THE STUDY: The aim of this study is volatiles profiling of three Juniperus species; J. communis, J. horizontalis and J. chinensis in addition to efficacy-directed discrimination of the three studied essential oils based on their antimicrobial, and anti-inflammatory activities in LPS (lipopolysaccharide)-stimulated WBCs (White blood cells) to investigate the inter-specific variability effect on the biological activities of each oil. MATERIALS AND METHODS: Volatile components profiling of the three studied plants volatile oils was achieved using GC-FID (Gas chromatography - flame ionization detector) and GC-MS (Gas chromatography - mass spectrometry). The antimicrobial activity of the studied essential oils was investigated and the minimum inhibitory concentration (MIC) was determined for oils. The production of the pro-inflammatory cytokines was evaluated by ELISA (Enzyme linked immunosorbent assay). Identification of the biomarkers responsible for each activity was attempted through construction of orthogonal projection to latent structures model using multivariate statistical analysis. RESULTS: Forty five components were identified in the volatile oils of the three studied plants. J. horizontalis oil displayed the highest activity against E. coli while J. communis showed the highest activity against S. aureus. OPLS model biplot showed the in-between class discrimination of J. chinensis oil sample from J. communis and J. horizontalis. The three oils were found to significantly decrease the production of the pro-inflammatory cytokines tumour necrosis factor (TNF)- alpha, interleukin (IL)-1beta, and gamma interferon (INF- gamma) in lipopolysaccharide-activated white blood cells. All studied oils were similar in reduction of TNF-alpha, and INF-gamma, while J. chinensis oil possessed the highest potency against IL-1beta. The coefficient plots of TNF-alpha and INF-gamma pro-inflammatory mediators showed that 1-terpineol, 4-terpineol, Bornyl Acetate, dl-limonene and alpha-pinene positive contributors to both activities while beta-thujone, 3-carene and gamma-muurolene were the positive contributors to IL-1beta inhibitory activity. CONCLUSION: The differences observed in the volatile profiles among the three studied oils demonstrate the effect of inter-specific variability on the biological activities of the tested oils. It was shown that the tested oils possessed good antibacterial activities against E.coli and S. aureus justifying its folk use as an a topical antiseptic while the observed anti-inflammatory effects in human WBCs is due at least in part to their inhibitory effect on the production of pro-inflammatory cytokines.

In vitro antimicrobial combinatory effect of Cinnamomum cassia essential oil with 8-hydroxyquinoline against Staphylococcus aureus in liquid and vapour phase.[Pubmed:32350955]

J Appl Microbiol. 2020 Apr 29.

AIMS: The objective of the study was to evaluate the antimicrobial interactions between two volatile agents, Cinnamomum cassia essential oil (CCEO) and 8-hydroxyquinoline (8-HQ) against Staphylococcus aureus strains in liquid and vapour phases. METHODS AND RESULTS: In vitro antimicrobial effect of CCEO in combination with 8-HQ was evaluated against 12 strains of S. aureus by broth volatilization chequerboard method. Results show additive effects against all S. aureus strains for both phases. In several cases, sums of fractional inhibitory concentration values of our test combinations were lower than 0.6, which can be considered as a strong additive interaction. Moreover, composition of CCEO was analysed by gas chromatography-mass spectrometry analysis. In the CCEO, 26 compounds in total were identified, where (E)-cinnamaldehyde was the predominant compound, followed by cinnamyl acetate, alpha-copaene, Bornyl Acetate and caryophyllene. CONCLUSIONS: Results showed additive in vitro growth-inhibitory effect of CCEO and 8-HQ combination against various standard strains and clinical isolates of S. aureus. SIGNIFICANCE AND IMPACT OF THE STUDY: This is the first report on antibacterial effect of 8-HQ and CCEO combination in liquid and vapour phases. Results of the study suggest these agents as potential candidates for development of new anti-staphylococcal applications that can be used in the inhalation therapy against respiratory infections.

Development of a comprehensive quality control method for the quantitative analysis of volatiles and lignans in Magnolia biondii Pamp. by near infrared spectroscopy.[Pubmed:31982656]

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Apr 5;230:118080.

The quality of drug is vital to its curative effect, thus it is important to develop a comprehensive quality control method for commonly used drugs. In this study, we developed a Gas chromatography-mass spectrometry separation method for the qualitative and quantitative analysis of volatiles, together with a High-performance liquid chromatography-mass spectrometry separation method for lignans in Magnolia biondii Pamp.. 79 volatiles and 11 lignans were identified via comparing their chromatographic behavior and mass spectra data with those in the literature. The methods were then used to determine the contents of volatiles (1, 8-cineole, d-Limonene, alpha-terpineol, linalool, L-camphor brain and Bornyl Acetate) and lignans (epieudesmin, magnolin, epi-magnolin A and fargesin) in Magnolia biondii Pamp.. Subsequently, 13 qualitative models including volatiles (1, 8-cineole, d-Limonene, alpha-terpineol, linalool, L-camphor brain and Bornyl Acetate), water-soluble extractive, lignans (pinoresinol dimethyl ether, magnolin, epi-magnolin A and fargesin) and moisture were developed by Near-Infrared Spectroscopy based on partial least square regression herein. The reference values were obtained by High-performance liquid chromatography, Gas chromatography and etc., while the predicted values were attained from the NIR spectrum. Compared with the traditional detection methods, NIR technique methodology significantly improved the ability to evaluate the quality of Magnolia biondii Pamp., which had the advantages of convenience, celerity, highly efficiency, low cost, no harm to samples, no reagent consumption, and no pollution to the environment. Moreover, the systematic analysis method combined pharmaceutical analysis with pharmacochemistry was proposed to prepare volatiles, water-soluble extractive and lignans parts from the same sample. This way could extract more index components to be beneficial in the quality control of Magnolia biondii Pamp. roundly.

Use of Autochthonous Lactobacilli to Increase the Safety of Zgougou.[Pubmed:31877880]

Microorganisms. 2019 Dec 22;8(1). pii: microorganisms8010029.

Seeds of Pinus halepensis are used for preparing zgougou, a spontaneously fermented matrix giving juice and seeds debris, consumed in many Arabian countries, including Tunisia. In the same way as all the food processes based on spontaneous fermentation, zgougou hides health risks due to eventual pathogenic microorganisms and derived toxins. This study aimed at investigating the effect of the use of autochthonous Lactobacillus paraplantarum A1 and Lactobacillus plantarum A2, as fermentation starters, on the microbiological characteristics, profiles of volatile organic compounds (VOC), antibacterial and antioxidant activities of juice and seeds debris from zgougou. The starter lactobacilli inhibited undesired bacteria (e.g., Enterobacter and Aeromonas) and coccus-shaped lactic acid bacteria, as shown by culture-dependent and-independent methods. The inhibitory effect was more evident in juice than in seeds debris. Some VOC (ethanol, acetoin, phenol,2-methoxy and caryophyllene) were present at higher concentrations in juice and seeds obtained upon spontaneous fermentation, compared to the samples deriving from fermentation with lactobacilli. The latter samples were characterized by higher concentrations of acetic acid, decane, 1-nonanol, Bornyl Acetate and bornyl formate. In addition, they showed a wider spectrum of antibacterial activity than spontaneously fermented juice and seeds. The use of autochthonous lactobacilli did not relevantly affect the antioxidant activity of zgougou. When juice from lactobacilli-driven fermentation was used to prepare a traditional Tunisian pudding ("Assidat-Zgougou"), it improved color and odor with respect to the pudding containing juice from spontaneous fermentation. This study showed that the use, at laboratory scale, of autochthonous lactobacilli is a feasible biotechnological tool to outgrow undesired bacteria, thus improving the safety of zgougou juice. Future studies should be undertaken to confirm the observed benefits at industrial scale.

Contact toxicity and repellent efficacy of Valerianaceae spp. to three stored-product insects and synergistic interactions between two major compounds camphene and bornyl acetate.[Pubmed:31877546]

Ecotoxicol Environ Saf. 2020 Mar 1;190:110106.

In this work, the essential oil (EO) and supercritical CO2 fluid extract (SF extract) of four Valerianaceae plants (Valeriana officinalis L., Valeriana officinalis L. var. latifolia Miq., Valeriana jatamansi Jones and Nardostachys chinensis Bat.) were chemically characterized. GC-MS analysis identified 74 compounds, representing 35.2%-82.4% of the total EOs and SF extracts. The EO was dominated by low-molecular-weight components while the SF extract was rich in fatty acids. Bornyl Acetate and camphene were the characteristic compounds in EO and SF extracts. The efficacy of six extracts against three stored-product insects was investigated. In contact assays, V. officinalis exhibited strongest toxicity to red flour beetle (LD50 = 10.0 mug/adult), and V. jatamansi EO was the most active one against the cigarette beetle (LD50 = 17.6 mug/adult), while V. officinalis var. latifolia EO showed outstanding efficacy against the booklouse (LD50 = 40.2 mug/cm(2)). Binary mixtures of two major compounds (camphene and Bornyl Acetate) were assessed for the contact toxicity to the red flour beetle. Additive effect existed in the natural proportion of V. officinalis, and synergism was observed in that of V. officinalis var. latifolia. This work confirmed the insecticidal efficacy of the species of the Valerianaceae family, and it would offer some information for the development of botanical insecticide.

Chemical Composition of Ambrosia trifida Essential Oil and Phytotoxic Effect on Other Plants.[Pubmed:31692228]

Chem Biodivers. 2020 Jan;17(1):e1900508.

This study aimed to identify the main components of an essential oil produced from leaves of Ambrosia trifida and to evaluate its potential allelopathic effect on seed germination and seedling growth of lettuce, watermelon, cucumber and tomato. The essential oil was obtained by hydrodistillation and characterized chemically by gas chromatography (GC) coupled with both mass spectrometry (MS) and flame ionization detector (FID). Total 69 compounds were identified, with limonene (20.7 %), Bornyl Acetate (15.0 %), borneol (14.7 %) and germacrene D (11.6 %) as the major components. The working solutions of the essential oil emulsified with Tween 20 and dissolved in distilled water were prepared at four concentration levels (0.01, 0.1, 0.5 % and 1 %, v/v). The results obtained showed that increase in essential oil concentration leads to decrease in seed germination, as well as shoot and radical length of lettuce, watermelon, cucumber and tomato. The obtained data revealed a highly significant effect (p<0.05) between control and 1 % and 0.5 % oil concentrations in all treatments. The essential oil of A. trifida exhibited more powerful phytotoxic effects on lettuce, watermelon and tomato than on cucumber regarding germination and early seedling growth.

Terpenes and Phenylpropanoids as Acetyl- and Butyrylcholinesterase Inhibitors: A Comparative Study.[Pubmed:31660828]

Curr Alzheimer Res. 2019;16(10):963-973.

BACKGROUND: Cholinesterase inhibitors are routinely applied in the treatment of Alzheimer's disease, and seeking new cholinesterase inhibitors is a priority. OBJECTIVES: Twenty seven compounds were compared, including ones not previously tested. An attempt was undertaken to precisely describe the role of alcohol in the inhibitory activity. This paper underlines the role of a "false positive" blank sample in the routine analysis. METHODS: The inhibition of cholinesterase was measured using Ellman's colorimetric method with a few modifications designed by the authors (including the "false-positive" effect). The inhibitory role of ethanol and methanol was also carefully evaluated. The present and past results were compared taking the source of enzyme and alcohol content into consideration. RESULTS: For the first time, new inhibitors were identified, namely: methyl jasmonate, 1R-(-)-nopol ((anti-acetyl-(AChE) and butyrylcholinesterase (BChE) activity)) and 1,4-cineole, allo-aromadendrene, nerolidol, beta-ionone, and (R)-(+)-pulegone (anti-BChE activity). Oleanolic acid and (+)-beta-citronellene (not previously studied) proved to be inefficient inhibitors. For a number of well-known inhibitors (such as nerol, (-)-menthol, (+)-menthol, isoborneol, (-)-Bornyl Acetate, limonene, alpha-pinene, beta-pinene, alpha- ionone, and eugenol) some serious discrepancies were observed between our findings and the results of previous studies. Ethanol and methanol showed no anti-AChE activity up to 0.29% (v/v) and 0.23% (v/v), respectively. Similarly, ethanol up to 0.33% (v/v) and methanol up to 0.29% (v/v) did not inhibit the activity of BChE. CONCLUSION: It can be stated that the impact of alcohol should be precisely determined and that blank "false-positive" samples should be processed together with test samples. Furthermore, the effect of the enzyme origin on the result of this test must be taken into consideration.

Comparative study of the morphological and phytochemical characterization of Romanian Solidago species.[Pubmed:31608876]

Pak J Pharm Sci. 2019 Jul;32(4):1571-1579.

In the present study, three indigenous species of Solidago genus (Solidago gigantea, Solidago virgaurea and Solidago canadensis) have been analyzed for the assessment of polyphenolic, phenyl propane derivates and essential oil contents. In addition, a comparative morphological study was also described. The leaves and the flowers of the three Solidago species were studied by scanning electron microscopy (SEM). The qualitative and quantitative characterizations of the main polyphenolic compounds from the hydrolyzed extracts were carried out by using high performance liquid chromatography with UV detection (HPLC-UV), high performance liquid chromatography coupled with mass spectrometry (HPLC-MS) and gas chromatography coupled with mass spectrometry (GC-MS) for the essential oil determination. The dominant flavonoidic aglycone found for all three species was quercetol with its highest concentration registered in Solidago canadensis. Four components, alpha-pinene, mircene, Bornyl Acetate and germacrene D, were detected in all the analyzed samples of essential oils. According to the comparative morphological analysis, morphoanatomical differences were observed for the tryhomes, stomata and flowers of the studied Romanian Solidago species.

Comparison of Chemical Composition of the Essential Oils from Different Botanical Organs of Pinus mugo Growing in Poland.[Pubmed:31475763]

Chem Biodivers. 2019 Oct;16(10):e1900397.

The essential oils from needles, twigs, bark, wood, cones and young shoots of Pinus mugo were analyzed by GC, GC/MS, and (1) H-NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were 3-carene (23.8 %), myrcene (22.3 %), and alpha-pinene (10.3 %). The needle oil contained mainly alpha-pinene (18.6 %), 3-carene (11.3 %), and Bornyl Acetate (8.3 %). The oils from twigs without needles, young shoots, bark, and wood were dominated by 3-carene (28.6 %, 15.0 %, 18.5 %, and 34.6 %, respectively) and myrcene (23.4 %, 24.0 %, 24.6 %, and 9.4 %, respectively). In the cone oil (E)-beta-caryophyllene was the main constituent (24.0 %).

Effects of processing and storage conditions on volatile composition and odor characteristics of blackcurrant (Ribes nigrum) juices.[Pubmed:31151596]

Food Chem. 2019 Sep 30;293:151-160.

Blackcurrant juices were prepared without enzyme (NEB-juice) and with conventional enzyme-aided berry pressing (EB-juice). Juices were pasteurized and stored at ambient temperature (in light and dark conditions) and at +4 degrees C for a 1-year period of time. Volatile composition and odor attributes were followed by HS-SPME-GC-MS and a sensory panel, respectively. Volatiles were decreased in the EB-juice, showing 100-fold lower contents of the main terpenoids, e.g., alpha-pinene, delta-3-carene, limonene, terpinolene, Bornyl Acetate and beta-caryophyllene; whereas esters, such as methyl butanoate and ethyl butanoate, showed 2- and 4-fold lower contents for the EB-juice. Pasteurization produced minor changes in both juices. Volatiles decreased during storage at room temperature while at +4 degrees C esters and eucalyptol were kept at 100%. The descriptive sensory analysis reported a significant decrease (p<0.05) of the berry-like odor after 12-month storage at RT. Storage at +4 degrees C for 12months did not affect the odor quality.

Comparison of Volatile Oil between the Fruits of Amomum villosum Lour. and Amomum villosum Lour. var. xanthioides T. L. Wu et Senjen Based on GC-MS and Chemometric Techniques.[Pubmed:31035329]

Molecules. 2019 Apr 28;24(9). pii: molecules24091663.

Fructus Amomi (FA) is usually regarded as the dried ripe fruit of Amomum villosum Lour. (FAL) or Amomum villosum Lour. var. xanthioides T. L. Wu et Senjen (FALX.). However, FAL, which always has a much higher price because of its better quality, is often confused with FALX. in the market. As volatile oil is the main constituent of FA, a strategy combining gas chromatography-mass spectrometry (GC-MS) and chemometric approaches was applied to compare the chemical composition of FAL and FALX. The results showed that the oil yield of FAL was significantly higher than that of FALX. Total ion chromatography (TIC) showed that cis-nerolidol existed only in FALX. Bornyl Acetate and camphor can be considered the most important volatile components in FAL and FALX., respectively. Moreover, hierarchical cluster analysis (HCA) and principal component analysis (PCA) successfully distinguished the chemical constituents of the volatile oils in FAL and FALX. Additionally, Bornyl Acetate, alpha-cadinol, linalool, beta-myrcene, camphor, d-limonene, terpinolene and borneol were selected as the potential markers for discriminating FAL and FALX. by partial least squares discrimination analysis (PLS-DA). In conclusion, this present study has developed a scientific approach to separate FAL and FALX. based on volatile oils, by GC-MS combined with chemometric techniques.

Efficacy of bornyl acetate and camphene from Valeriana officinalis essential oil against two storage insects.[Pubmed:30972667]

Environ Sci Pollut Res Int. 2019 Jun;26(16):16157-16165.

The essential oil was extracted from the roots of Valeriana officinalis L. by hydrodistillation. The qualitative and quantitative analysis of its chemical constituents was conducted on GC-MS and GC-FID in this study. Seventeen compounds were detected and the major constituents included Bornyl Acetate (48.2%) and camphene (13.8%). The toxic and repellent effects of the essential oil and its two major constituents were evaluated on Liposcelis bostrychophila and Tribolium castaneum. The results of bioassays indicated that the essential oil showed the promising fumigant and contact toxicity against L. bostrychophila (LC50 = 2.8 mg/L air and LD50 = 50.9 mug/cm(2), respectively) and the notable contact effect on T. castaneum (LD50 = 10.0 mug/adult). Meanwhile, the essential oil showed comparable repellent effect on T. castaneum at all testing concentrations. Bornyl Acetate and camphene also exhibited strong fumigant and contact toxicity against both species of pests (LC50 = 1.1, 10.1 mg/L air and LD50 = 32.9, 701.3 mug/cm(2) for L. bostrychophila; > 126.3, 4.1 mg/L air, and 66.0, 21.6 mug/adult for T. castaneum). Bornyl Acetate and camphene showed moderate repellent effect on T. castaneum and conversely showed attractant effect on L. bostrychophila. This work highlights the insecticidal potential of V. officinalis, which has been noted as a traditional medicinal plant.

Antimicrobial Activity and Chemical Composition of Essential Oil Extracted from Solidago canadensis L. Growing Wild in Slovakia.[Pubmed:30934783]

Molecules. 2019 Mar 27;24(7). pii: molecules24071206.

Plant essential oils (EOs) are one of the most relevant natural products due to their biological, medicinal, and nutritional properties. The promising biological effects of many plants EOs encourage researchers to study their biochemical properties to be used as possible natural alternatives for commercial pesticides and not only as herbal medicines. The current research has been conducted to study the microbicide effect of Solidago canadensis L. EO to control some common plant diseases caused by several postharvest phytopathogenic fungi (Monilinia fructicola, Botrytis cinerea, Aspergillus niger, and Penicillium expansum) in comparison with Azoxystrobin as a large spectrum fungicide. The antibacterial activity has been carried out against some phytopathogenic bacteria (Bacillus megaterium and Clavibacter michiganensis (G+ve) and Xanthomonas campestris, Pseudomonas fluorescens, and Pseudomonas syringae pv. phaseolicola (G-ve)) compared to the synthetic antibiotic Tetracycline. Minimum inhibitory concentration was carried out to determine the lowest effective EO dose using a 96-well microplate. The cell membrane permeability was also evaluated by measuring the electric conductivity (EC) to examine the possible mechanisms of action of S. canadensis EO. Chemical characterization of EO has been carried out using gas chromatography and mass spectrometry (GC-MS). Thirty-two identified components in S. canadensis EO presented 97.7% of total compounds in EO. The principal compounds were identified as germacrene D (34.9%), limonene (12.5%), alpha-pinene (11.6%), beta-elemene (7.1%), and Bornyl Acetate (6.3%). In addition, S. canadensis EO demonstrated promising in vitro antimicrobial activities against the majority of tested phytopathogens at all tested concentrations.