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limonene’s Bacteriostatic Activity against Ralstonia solanacearum by Compromised Membrane Integrity: A Transcriptomic and Metabolomic Analysis

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Journal of Agricultural Chemistry and Environment 2024年第3期13卷 312-324页

作者： Ruya Zhang Honghao Zhang Linfeng Li Yuchen Feng Lin Yang Jiaxin Liu Senfeng Gao Zihao Zhou Yong Yang Haibo Xiang Mei Li Jun Yu College of Life Sciences Hubei University Wuhan China State Key Laboratory of Biocatalysis and Enzyme Engineering College of Life Sciences Hubei University Wuhan China Tobacco Research Institute of Hubei Province Wuhan China

Ralstonia solanacearum, the causative agent of bacterial wilt, is a soil-borne pathogen that poses a widespread threat to plants in the Solanaceae family. To elucidate the mechanism by which limonene exerts its effects on R. solanacearum, we first assessed the impact of limonene on the physiological indicators of the pathogen and subsequently analyzed its transcriptome and metabolome. Our findings indicate that limonene has a potent inhibitory effect on R. solanacearum, and it also suppresses the formation of the bacterial community biofilm. limonene primarily regulates the terpene biosynthesis pathway in R. solanacearum, thereby potentially affecting signal transduction in the pathogen and disrupting its normal growth and development. These results significantly enhance our understanding of limonene’s response to the induction of bacterial wilt and provide a reference for further prevention and control of R. solanacearum.

关键词： limonene Transcriptome Metabolome Ralstonia solanacearum Terpenoid Backbone Biosynthesis

Safety and Feasibility of Topical Application of limonene as a Massage Oil to the Breast

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Journal of Cancer Therapy 2012年第5期3卷 749-754页

作者： Jessica A. Miller Patricia A. Thompson Iman A. Hakim Ana Maria Lopez Cynthia A. Thomson Wade Chew Chiu-Hsieh Hsu H.-H. Sherry Chow Mel & Enid Zuckerman College of Public Health The University of Arizona Tucson USA The University of Arizona Cancer Center Tucson USA

Background: limonene, a major component in citrus oil, has demonstrated anti-cancer effects in preclinical mammary cancer models. However, the effective oral dose translates to a human dose that may not be feasible for chronic dosing. We proposed to evaluate topical application of limonene to the breast as an alternative dosing strategy. Materials and Methods: We conducted a mouse disposition study to determine whether limonene would be bioavailable in the mammary tissue after topical application. SKH-1 mice received topical or oral administration of limonene in the form of orange oil every day for 4 weeks. Plasma and mammary pads were collected 4 hrs after the final dosing. We also conducted an exploratory clinical study to evaluate the safety and feasibility of topically applied limonene in the form of orange oil to the breast. Healthy women were recruited to apply orange oil containing massage oil to their breasts daily for four weeks. Safety and feasibility were assessed by reported adverse events, clinical labs, and usage compliance. Pre and post-intervention nipple aspirate fluid (NAF) and plasma were collected for limonene concentration determination. Results: The mouse disposition study showed that topical and oral orange oil administration resulted in similar mammary tissue disposition of limonene with no clinical signs of toxicity. In the clinical study, the topical application of limonene containing massage oil to the breast was found to be safe with high levels of usage compliance for daily application, although NAF and plasma limonene concentrations were not significantly changed after the massage oil application. Conclusions: Our studies showed that limonene is bioavailable in mammary tissue after topical orange oil application in mice and this novel route of administration to the breast is safe and feasible in healthy women.

关键词： limonene Topical Application Safety

Diversity in chemical compositions of essential oil of myrtle leaves from various natural habitats in south and southwest Iran

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Journal of Forestry Research 2015年第4期26卷 971-981页

作者： Abdollah Ghasemi Pirbalouti Lyle E.Craker Department of Medicinal Plants Islamic Azad UniversityShahrekord Branch Medicinal Plants Program Stockbridge School of AgricultureCollege of Natural SciencesUniversity of Massachusetts

Myrtle, Myrtus communis L. （Myrtaceae）, an evergreen shrub also known as wild myrtle, has a history of use as a culinary and medicinal plant. To determine the diversity within the species, plant leaves of myrtle were collected in 12 natural habitats in Iran for investigation of chemical constituents in the essential oil. Extraction of the essential oils produced yields ranging from 0.7 to 1.5 mL per 100 g dry tissue. An analysis of the oils by GC and GC/MS revealed 40 compounds, constituting 90.1-99.9 % of the essential oils. Chemical constituents varied with the site of sample origin, although the principal essential oil compo- nents from all populations, were pinene （17.5-37.1%）, 1,8-cineole （9.9-29.8 %）, linalool （7.0-23.1%）, and a-ter- pineol （5.3-8.3 %）. limonene （tr, 22.7 %） was a major constituent in three populations. Characterized chemotypes included Chemotype pinene/1,8-cineole/linalool, Chemotype II： a-pinene/linalool, Chemotype III： a-pinene/1,8- cineole, and Chemotype IV： pinene/1,8-cineole/*** main source of variabifity in chemical composition and oil yield appeared to be differences in environmental conditions and chemotypes as plant populations collected from close geographical areas could be classified in a cluster.

关键词： Chemotypes Myrtus communis limonene Linalool 1,8-Cineole Pinene Variation

Isolation and Identification of the Major Chemical Components Found in the Upper Parts of Teucrium Pofium Plants Grown in Khuzestan Province of Iran

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Chinese Journal of Chemistry 2007年第8期25卷 1171-1173页

作者： ASHNAGAR Alamdar GHARIB NASERI Nahid FOROOZANFAR Shahla School of Pharmacy Ahwaz Jundi Shapour University of Medical Sciences Ahwaz Iran Ahwaz Faculty of Petroleum Engineering Petroleum University of Technology Ahwaz Iran

Teucrium polium is a dwarf sub-shrub usually 30-60 cm high with many branches, which is fairly distributed throughout Iran, with its flowering being season mainly from April to July. The plant was collected during its flowering season in Baghmalek region in the North-East of Khuzestan province, Iran. After the identification of the genus, species and variety of the plant, the dried whole plant （flowers, fruits and the leaves） was steam distilled with different methods. The isolated essential oil was dried over anhydrous sodium sulphate and stored at 4-6 ℃. Analysis of the essential oil was carried out by GC-MS technique. At least 10 major components were identified （3-carene/α-pinene, β-phellandrene, limonene, germacrene, β-bourbonene, β-caryophylene, γ-muurolene, γ-elemene, spathulenol, β-eudesmol）（totally 97.02%）. Also, successive TLC and column chromatography of the essential oil resulted in the separation of four fractions. Based upon 1^H NMR, IR and mass spectra, the fractions with Rf=0.12 and 0.93 were determined as gualol and a mixture of α-pinene, β-phellandrene and limonene, respectively.

关键词： teucrium polium labiatae germander α-pinene β-phellandrene limonene guaiol GC-mass analysis

Caraway as Important Medicinal Plants in Management of Diseases

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Natural Products and Bioprospecting 2019年第1期9卷 1-11页

作者： Mohaddese Mahboubi Medicinal Plants Research Department Research and DevelopmentTabibDaru Pharmaceutical CompanyKashanIran

Carum carvi or caraway is traditionally used for treatment of indigestion,pneumonia,and as appetizer,galactagogue,and *** oil,fixed oil and many other valuable extractive compounds with industrial applications are prepared from *** review article has new deep research on caraway as medicinal *** preparing the manuscript,the information was extracted from accessible international databases(Google scholar,PubMed,Science direct,Springer,and Wiley),electronic resources and traditional books by key word of caraway or Carum *** results of traditional studies exhibited that the galactagogue and carminative effects of caraway fruits are superior to other ***,the traditional scholars used it as appetizer,while caraway was the main ingredient of anti-obesity drugs in traditional medicine,which has been confirmed in two modern clinical trials of human *** oil in combination with peppermint oil or menthol is used for treatment of functional dyspepsia in clinical *** oil topically on abdomen relieves the IBS symptoms in ***,the use of caraway oil is not recommended in adults under 18 years due to insufficient data,but it can topically use as anti-colic and carminative agent in children or *** antiaflatoxigenic,antioxidant and antimicrobial effects of caraway oil along with its reputation as spice help the industries to use it as natural preservatives and antioxidant agents.

关键词： Caraway Carum carvi Obesity Functional dyspepsia Preservative Carvone limonene

Essential oil from Zanthoxylum bungeanum Maxim. and its main components used as transdermal penetration enhancers: a comparative study

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2014年第11期15卷 940-952页

作者： Yi LAN Hui LI Yan-yan CHEN Ye-wen ZHANG Na LIU Qing ZHANG Qing WU School of Chinese Materia Medica Beijing University of Chinese Medicine

Our previous studies had confirmed that the essential oil from Zanthoxylum bungeanum Maxim. （Z. bungeanum oil） could effectively enhance the percutaneous permeation of drug molecules as a natural transdermal penetration enhancer. The aim of the present study is to investigate and compare the skin penetration enhancement effect of Z. bungeanum oil and its main components on traditional Chinese medicine （TCM） active components. Toxicities of Z. bungeanum oil and three selected terpene compounds （terpinen-4-ol, 1,8-cineole, and limonene） in epidermal keratinocytes （HaCaT） and dermal flbroblast （CCC-ESF-1） cell lines were measured using an MTT （3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyltetrazolium bromide） assay. Five model drugs in TCM external preparations, namely osthole （OT）, tetramethylpyrazine （TMP）, ferulic acid （FA）, puerarin （PR）, and geniposide （GP）, which were selected based on their lipophilicity denoted by IogKo^w, were tested using in vitro permeation studies in which vertical Franz diffusion ceils and rat abdominal skin were employed. The secondary structure changes of skin stratum corneum （SC） and drug thermodynamic activities were investigated to understand their mechanisms of action using Fourier transform infrared （FTIR） spectroscopy and saturation solubility studies, respectively. It was found that Z. bungeanum oil showed lower toxicities in both HaCaT cells and CCC-ESF-1 cells compared with three terpene compounds used alone. The enhancement permeation capacities by all tested agents were in the following increasing order： terpinen-4-ol=1,8-cineole〈limonene〈Z, bungeanum oil. The mechanisms of permeation enhancement suggested that these enhancers promoted the skin permeation of drugs mainly by affecting SC lipids. These results indicated that Z. bungeanum oil exhibited better performance in enhancing the skin permeation of active components in TCM preparations.

关键词： Zanthoxylum bungeanum Maxim. Essential oil limonene Fourier transform infrared (FTIR) spectroscopy Penetration enhancer HaCaT

Quantitative Surface Chirality Detection with Sum Frequency Generation Vibrational Spectroscopy： Twin Polarization Angle Approach

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Chinese Journal of Chemical Physics 2009年第6期22卷 592-600,J0001页

作者： Feng Wei Yan-yan Xu Yuan Guo Shi-lin Liu Hong-fei Wang Hefei National Laboratory for Physical Sciences at Microscale Department of Chemical PhysicsUniversity of Science and Technology of China Hefei 230025 China Beijing National Laboratory for Molecular Sciences Laboratory of Molecular Reaction Dynamics Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China

Here we report a novel twin polarization angle （TPA） approach in the quantitative chirality detection with the surface sum-frequency generation vibrational spectroscopy （SFG-VS）. Generally, the achiral contribution dominates the surface SFG-VS signal, and the pure chiral signal is usually two or three orders of magnitude smaller. Therefore, it has been difficult to make quantitative detection and analysis of the chiral contributions to the surface SFG- VS signal. In the TPA method, by varying together the polarization angles of the incoming visible light and the sum frequency signal at fixed s or p polarization of the incoming infrared beam, the polarization dependent SFG signal can give not only direct signature of the chiral contribution in the total SFG-VS signal, but also the accurate measurement of the chiral and achiral components in the surface SFG signal. The general description of the TPA method is presented and the experiment test of the TPA approach is also presented for the SFG-VS from the S- and R-limonene chiral liquid surfaces. The most accurate degree of chiral excess values thus obtained for the 2878 cm^-1 spectral peak of the S- and R-limonene liquid surfaces are （23.7±0.4）% and （-25.4±1.3）%, respectively.

关键词： Sum-frequency generation vibrational spectroscopy Twin polarization angle approach Surface Chirality limonene

Determination of Perillic Acid in Bioconversion Supernatants by Gas Chromatography

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American Journal of Analytical Chemistry 2017年第10期8卷 636-644页

作者： Eliane G. Carvalho Antonio C. Siani Igor C. Cardoso Virginia Garcia Correia Maria A. Ferrara Elba P. S. Bon Marcelo R. Romero Tappin Medicine and Drug Technology Institute Oswaldo Cruz Foundation Rio de Janeiro Brazil Chemistry Institute Federal University of Rio de Janeiro Rio de Janeiro Brazil

Perillic acid can be obtained from microbial oxidation of the exocyclic methyl group of limonene. Due to the pharmacological potential of such a metabolite, the biotransformation processes leading to its synthesis have been approached in recent studies. A robust analytical method is needed to assess the performance of such studies. An analytical method was developed and validated to determine perillic acid in the supernatants of a yeast-induced bioconversion of limonene, involving gas chromatography (GC) and an acid-induced precipitation during the sample preparation. GC analysis was performed using a column with polyethylene glycol as stationary phase (HP-Innowax) which resulted in higher loads and better peak shape. The sample preparation involved the supernatant initial filtration and precipitation with 0.6 M HCl followed by centrifugation and dissolution in ethyl acetate. GC analysis conditions were oven from 50°C to 250°C at 20°C·min-1, and then held 5 min (total runtime 15 min). Injector was set at 280°C, and detector at 300°C. Helium was the carrier gas at 1 ml·min-1. Injections of 1.0 μl were at the split ratio 25:1. The method was validated: Linearity with R2 of 0.9992, Accuracy of 98.3% in the range 190 - 950 μg·ml-1;Limit of detection of 10.4 μg·ml-1;Repeatability of 2.1% RSD. Thus, a complete methodology to determine perillic acid in a bioconversion supernatant was developed and validated. This overall approach may be useful for bioconversions of monoterpenes by other microorganisms that metabolize limonene.

关键词： limonene Perillic Acid Sample Preparation Gas Chromatography

Synthesis of the Prospective Anticancer Molecule Perillic Acid from Orange Essential Oil by the Yeast <i>Yarrowia lipolytica</i>

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Green and Sustainable Chemistry 2017年第2期7卷 172-184页

作者： Marcelo R. R. Tappin Felipe M. Knopp Igor C. Cardoso Roberta T. Santos Bruna S. Drummond Antonio C. Siani Elba P. S. Bon Maria Antonieta Ferrara Institute of Drug Technology Oswaldo Cruz Foundation Rio de Janeiro Brazil Chemistry Institute Federal University of Rio de Janeiro Rio de Janeiro Brazil

The bioconversion of the hydrophobic and volatile limonene to perillic acid, a potential anticancer agent, by the yeast Yarrowia lipolytica was studied in two steps. Firstly, experimental design was used for process optimization using high-purity limonene as substrate and secondly orange essential oil containing 89.1% limonene was used as substrate under the previously optimized conditions. limonene concentration and pH were identified by fractional factorial design as significant factors and were optimized by central composite design. Under optimized process conditions (0.16% (v/v) limonene;pH 6.9), the 24 h biotransformation process resulted in the accumulation of 0.368 g·L-1 of perillic acid corresponding to a molar yield of 23.1%. A subsequent substrate addition under the same reaction conditions doubled perillic acid concentration to 0.793 g·L-1 and a molar yield of 24.2%. The use of orange essential oil under the optimized reaction conditions increased both perillic acid accumulation and yield to 0.872 g·L-1 and 29.7%, respectively. The robustness of Y. lipolytica allowed the efficient biotransformation of a crude by-product of the citrus industry into a valuable fine chemical.

关键词： Yarrowia lipolytica Bioconversion Perillic Acid limonene Orange Essential Oil