Saturday, February 18, 2012

Phytochemicals in Foods - 10 Health Benefits of Limonene

Limonene is a phytochemicals in the class of Monoterpenes, found abundantly in
cherries, citrus essential oils, spearmint, dill, garlic, celery, maize, rosemary, ginger, basil, etc.

Health benefits
1. Anti-inflammatory
In the investigation of the monoterpene D-limonene and its metabolites have been shown to exert chemopreventive and chemotherapeutic effects against different tumours in animal models and clinical trials, found that D-limonene is an effective inhibitor of lipopolysaccharide (LPS)-induced NO and prostaglandin E(2) production in RAW 264.7 cells. These inhibitory effects of D-limonene included dose-dependent decreases in the expression of iNOS and COX-2 proteins, according to "Limonene suppresses lipopolysaccharide-induced production of nitric oxide, prostaglandin E2, and pro-inflammatory cytokines in RAW 264.7 macrophages" by Yoon WJ, Lee NH, Hyun CG.(1)

2. Antibacterial effect
In the assessment that GC and MS were used for the analysis of Croatian Centaurium erythraea Rafn essential oil (obtained by hydrodistillation) and headspace (applying headspace solid-phase microextraction). The headspace contained numerous monoterpene hydrocarbons (the major ones were terpinene-4-ol, methone, p-cymene, γ-terpinene and limonene), found that the oil fractionation enabled identification of other minor compounds not found in total oil such as norisoprenoides, alk-1-enes or chromolaenin. The essential oil showed antimicrobial potential on Escherichia coli, Salmonella enteritidis, Staphylococcus aureus and Bacillus cereus. On the other hand, no antibacterial activity of the oil was observed on Pseudomonas fluorescens and Lysteria monocytogenes, according to "Volatile Organic Compounds from Centaurium erythraea Rafn (Croatia) and the Antimicrobial Potential of Its Essential Oil" by Jerković I, Gašo-Sokač D, Pavlović H, Marijanović Z, Gugić M, Petrović I, Kovač S(2)

3. Skin tumorigenesis
In the investigation of the effects of limonene on the growth of 7,12-dimethylbenz[a]anthracene (DMBA)-initiated and 12-O-tetradecanoylphorbol-13-acetate (TPA)-promoted skin tumor development, found that -limonene (50 and 100 mg/kg body weight) treatments to the mouse skin significantly reduced the TPA-induced (a) edema and hyperplasia (p < 0.001); (b) expression of cyclooxygenase-2; (c) ornithine decarboxylase activity (p < 0.001); and (d) [(3)H] thymidine incorporation into DNA (p < 0.001), In addition, treatment of -limonene effectively restored the level of reduced glutathione, glutathione peroxidase, glutathione reductase, glutathione S-transferase, catalase and malondialdehyde production in TPA-treated mouse skin. In a two-stage skin tumorigenesis study, limonene significantly reduced the tumor burden (p < 0.005) and tumor incidence as compared to DMBA/TPA-treated mice. -Limonene treatment also extended the latency period of tumor development from 4 to 9 weeks. Limonene treatment decreased the expression level of Ras, Raf and phosphorylation of extracellular signal-regulated protein kinase 1/2 in DMBA/TPA-induced tumors.according to "D-Limonene modulates inflammation, oxidative stress and Ras-ERK pathway to inhibit murine skin tumorigenesis" by Chaudhary SC, Siddiqui MS, Athar M, Alam MS.(3)

4. Antihyperlipidemic Effects
In the investigation of the antihyperlipidemic activities of the essential oil from the leaves of Pinus koraiensis SIEB (EOPK) that has been used as a folk remedy for heart disease, found that
EOPK up-regulated low density lipoprotein receptor (LDLR) at the mRNA level as well as negatively suppressed the expression of sterol regulatory element-binding protein (SREBP)-1c, SREBP-2, 3-hydroxy-3-methyl-glutaryl-CoA reductase (HMGCR), fatty acid synthase (FAS) and glycerol-3-phosphate acyltransferase (GPAT) involved in lipid metabolism in HepG2 cells. Also, western blotting showed that EOPK activated LDLR and attenuated the expression of FAS at the protein level in the cells. Consistently, EOPK significantly inhibited the level of human acylcoenzyme A: cholesterol acyltransferase (hACAT)1 and 2 and reduced the low-density lipoprotein (LDL) oxidation activity. Furthermore, chromatography-mass spectrometry (GC-MS) analysis showed that EOPK, an essential oil mixture, contained camphene (21.11%), d-limonene (21.01%), α-pinene (16.74%) and borneol (11.52%), according to "Essential Oil of Pinus koraiensis Leaves Exerts Antihyperlipidemic Effects via Up-regulation of Low-density Lipoprotein Receptor and Inhibition of Acyl-coenzyme A: Cholesterol Acyltransferase" by Kim JH, Lee HJ, Jeong SJ, Lee MH, Kim SH.(4)

5. Antioxidant effects
In the evaluation of evaluate the antioxidant capacity and the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity of the peel essential oils from three Citrus species, C. aurantifolia Swingle, C. aurantium L., and C. bergamia Risso & Poit, found that the demonstrated antioxidant activity and procholinesterase properties of Citrus essential oils suggested their use as a new potential source of natural antioxidant to added as extra-nutrient for using in food industries as a valuable new flavor with functional properties for food or nutraceutical products with particular relevance to supplements for the elderly, according to "Comparative study on the antioxidant capacity and cholinesterase inhibitory activity of Citrus aurantifolia Swingle, C. aurantium L., and C. bergamia Risso and Poit. peel essential oils" by Tundis R, Loizzo MR, Bonesi M, Menichini F, Mastellone V, Colica C, Menichini F.(5)

6. Anti cancers
In the review attempted to collect all available published scientific literature of eight naturally occurring terpenoids and their effect on inhibition of tumor progression, found that literature survey revealed that triterpenoids, such as glycyrrhizic acid, ursolic acid, oleanolic acid, and nomilin, the diterpene andrographolide, and the monoterpenoids like limonene and perillic acid had shown immunomodulatory and antitumor activities. All of them could induce apoptosis in various cancer cells by activating various proapoptotic signaling cascades. Many of these terpenoids found to inhibit metastatic progression and tumor-induced angiogenesis, according to "Inhibition of tumor progression by naturally occurring terpenoids" by Kuttan G, Pratheeshkumar P, Manu KA, Kuttan R.(6)

7. Antigenotoxic properties
In the evaluation of the chemical composition and the DNA protective effect of the essential oils (EOs) from Lippia alba against bleomycin-induced genotoxicity, found that the EOs were not genotoxic in the SOS chromotest, but one of the major compound (limonene) showed genotoxicity at doses between 97 and 1549 mM. Both EOs protected bacterial cells against bleomycin-induced genotoxicity. Antigenotoxicity in the two L. alba chemotypes was related to the major compounds, citral and carvone, respectively. The results were discussed in relation to the chemopreventive potential of L. alba EOs and its major compounds, according to "Chemical composition and antigenotoxic properties of Lippia alba essential oils" by López MA, Stashenko EE, Fuentes JL.(7)

8. Microbial Effects
In the assessment of the composition of hydro-distilled and SC-CO(2) extracted oils. Nineteen constituents, which accounted for 89.32% of total constituents in HD oil, represented by limonene (4.31%), (Z)-β-ocimene (3.69%), terpinolene (22.24%), neryl acetate (36.19%), nerol (9.51%) and p-cymene-8-ol (2.61%) were identified. In SC-CO(2) extracted oil, 24 constituents representing 89.95% of total constituents were identified. Terpinolene (5.08%), germacrene D (2.17%), neryl acetate (51.62%), nerol (9.78%), geranyl acetate (2.06%), α-bisabolol (2.48%) and 1-nonadecanol (4.96%) were the dominating constituents anf their anti microbial effects, found that the oil exhibited moderate to high antimicrobial activity against fungi C. albicans (MIC 625 µg ml(-1)), A. parasiticus (MIC 312.5 µg ml(-1)), A. sydowii (MIC 312.5 µg ml(-1)), T. rubrum (MIC 625 µg ml(-1)), Gram-positive bacteria B. subtilis (MIC 625 µg ml(-1)) and Gram-negative bacteria P. aeruginosa (MIC 312.5 µg ml(-1)), according to "Composition and antimicrobial activity of the essential oil of Heracleum thomsonii (Clarke) from the cold desert of the western Himalayas" by Guleria S, Saini R, Jaitak V, Kaul VK, Lal B, Rahi P, Gulati A, Singh B.(8)

9. Antioxidant and anticarcinogenic effects
In the evaluation of the efficacy of fennel seed methanolic extract (FSME), such as flavonoids, terpenoids, alkaloids, phenols, and sterols; estragole (71.099%), gallic acid (18.895%), and L-limonene was the most prevalent monoterpene hydrocarbon (11.967%). for its antioxidant, cytotoxic, and antitumor activities and for its capacity to serve as a nontoxic radioprotector in Swiss albino mice, found that FSME may have remarkable anticancer potential against a breast cancer cell line (MCF7) and liver cancer cell line (Hepg-2). It also showed strong free radical-scavenging activity (100%). Thus, FSME may reduce oxidative stress and protect mouse cells from damage caused by reactive oxygen species. In addition, it could be used as a safe, effective, and easily accessible source of natural antioxidants to improve the oxidative stability of fatty foods during storage. FSME also exhibited an antitumor effect by modulating lipid peroxidation and augmenting the antioxidant defense system in EAC-bearing mice with or without exposure to radiation, according to "Antioxidant and anticarcinogenic effects of methanolic extract and volatile oil of fennel seeds (Foeniculum vulgare)" by Mohamad RH, El-Bastawesy AM, Abdel-Monem MG, Noor AM, Al-Mehdar HA, Sharawy SM, El-Merzabani MM.(9)

10. DNA protection and Anti tumors
In the assessment of the nutraceutical value of orange and lemon juices as well as two of their active compounds: hesperidin and limonene performed at three levels to evaluate different biological health promoter activities, found that Life-span experiments revealed that the lower concentrations of orange juice, hesperidin, and limonene exerted a positive influence on the life span of Drosophila. Finally all substances showed cytotoxic activity, with hesperidin being least active. Taking into account the safety, antigenotoxicity, longevity, and cytotoxicity data obtained in the different assays, orange juice may be a candidate as a nutraceutical food as it (1) is not genotoxic, (2) is able to protect DNA against free radicals, and (3) inhibits growth of tumor cells, according to "Role of citrus juices and distinctive components in the modulation of degenerative processes: genotoxicity, antigenotoxicity, cytotoxicity, and longevity in Drosophila" by Fernández-Bedmar Z, Anter J, de La Cruz-Ares S, Muñoz-Serrano A, Alonso-Moraga A, Pérez-Guisado J.(10)



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