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Abstract

Natural products obtained in dietary components may aid the prevention and treatment of a variety of diseases. Reports in the scientific literature have demonstrated that the consumption of terpenes is a successful alternative in the treatment of several diseases, triggering beneficial biological effects in clinical and preclinical studies. The monoterpene limonene is largely used in alimentary items, cleaning products, and it is one of the most frequent fragrances used in cosmetics formulation. The therapeutic effects of limonene have been extensively studied, proving anti-inflammatory, antioxidant, antinociceptive, anticancer, antidiabetic, antihyperalgesic, antiviral, and gastroprotective effects, among other beneficial effects in health. In this review, we collected, presented, and analyzed evidence from the scientific literature regarding the usage of limonene and its activities and underlying mechanisms involved in combating diseases. The highlighting of limonene applications could develop a useful targeting of innovative research in this field as well as the development of a limonene-based phytomedicine which could be used in a variety of conditions of health and disease.

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... Combination of high vapor pressure (190 Pa at 20°C) and low solubility in water, leads to a high Henry's law constant [the Henry's law volatility constant (k H )], which defines high vaporization rate of DL in aqueous systems (Filipsson, Åseda et al. 1998) and makes it a great flavoring agent. (Ciriminna et al., 2014) DL has been listed generally recognized as safe (GRAS) ingredient (Vieira, Beserra et al. 2018) as a flavoring agent under sections 201(s) and 409 of the Federal Food, Drug, and Cosmetic Act (the Act) and implementing regulations by the US Food and Drug Administration (FDA); so it is used as a flavoring agent in many food products (Sun 2007). Although, DL is a relatively stable component, and processes such as distillation can be done to isolate it from its sources, it degrades through oxidation at high temperatures and especially in the presence of oxygen. ...
... These therapeutic properties and health benefits can be summarized as anti-inflammatory (Hirota, Roger et al. 2010, d'Alessio, Ostan et al. 2013, Kummer, Fachini-Queiroz et al. 2013, Yu, Yan et al. 2017), antioxidant (Roberto, Micucci et al. 2010, Murali, Karthikeyan et al. 2013, anticancer (Yu, Lin et al. 2018, Ye, Liang et al. 2020 (Chi, Wei et al. 2013), and wound healing activity in preclinical or clinical studies. Several articles have reviewed some of these activities and health benefits (Vieira, Beserra et al. 2018). Some of the most important therapeutic properties and health benefits of DL have been summarized in Fig. 2 as a schematic representation. ...
Article
One of the major challenges in processing food products is preserving flavor-producing compounds. D-Limonene (DL) is a safe and common additive in the food and cosmetics industry. However, the high sensitivity of DL to oxidation reduces the intensity of its aroma and even the production of bad taste compounds, making the use of this additive problematic. Encapsulation may be an efficient way to introduce sensitive compounds such as DL into food products. In nanoencapsulation technology, by reducing the size of the carrier to nanometers, the surface-to-volume ratio increases dramatically, leading to increased encapsulation efficiency, improved bioavailability, and controlled release of encapsulated material. Hence, this review refers to updated information regarding DL nano-scaled delivery systems using different nanocarriers, its bioavailability, release rates as well as its application in functional food products and its toxicity when loaded into nanocarriers.
... However, the group of compounds with the greatest diversity of biological activities of interest are terpenes such as limonene, fucosterol, and dehydroabietic acid. These terpenes present antioxidant, anticancer, antiulcer, antihistaminic, antiadipogenic, antiphotodamaging, antimicrobial, antitumor, gastroprotective, hepatoprotective, antiviral, antihyperalgesic, anti-inflammatory, anticholinergic, anti-osteoporotic, antidiabetic, and antihyperlipidemic activities [49][50][51]. ...
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Ulomoides dermestoides are used as a broad-spectrum medical insect in the alternative treatment of various diseases. Preliminary volatilome studies carried out to date have shown, as the main components, methyl-1,4-benzoquinone, ethyl-1,4-benzoquinone, 1-tridecene, 1-pentadecene, and limonene. This work focused on the production of metabolites and their metabolic variations in U. dermestoides under stress conditions to provide additional valuable information to help better understand the broad-spectrum medical uses. To this end, VOCs were characterized by HS-SPME with PEG and CAR/PDMS fibers, and the first reported insect essential oils were obtained. In HS-SMPE, we found 17 terpenes, six quinones, five alkenes, and four aromatic compounds; in the essential oils, 53 terpenes, 54 carboxylic acids and derivatives, three alkynes, 12 alkenes (1-Pentadecene, EOT1: 77.6% and EOT2: 57.9%), 28 alkanes, nine alkyl disulfides, three aromatic compounds, 19 alcohols, three quinones, and 12 aldehydes were identified. Between both study approaches, a total of 171 secondary metabolites were identified with no previous report for U. dermestoides. A considerable number of the identified metabolites showed previous studies of the activity of pharmacological interest. Therefore, considering the wide variety of activities reported for these metabolites, this work allows a broader vision of the therapeutic potential of U. dermestoides in traditional medicine.
... Anethole has been analyzed for its antimicrobial, antifungal, anti-inflammatory, mutagenic, and cytotoxic activities [35,36]. Limonene exhibits antibacterial and cytotoxic activities [37]. Similarly, β-caryophyllene also possesses antibacterial, antioxidant, anti-inflammatory, and anticarcinogenic activities [36]. ...
Article
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Known for its high nutritional and medicinal value, okra (Abelmoschus esculentus) is commonly used for replacing plasma and expanding blood volume in humans. It is a major economic crop cultivated in tropical and subtropical regions worldwide. The present study aimed to investigate and evaluate the nutritional properties and prospective applications of the consumable parts of okra. The total ash content (mineral content), carbohydrate, crude fiber, fat, protein, and moisture fractions of okra pod aqueous extract were determined. The results show that okra aqueous extract contained 84.670–87.650% moisture, 1.514–1.197% ash, 7.857–8.261% carbohydrate, 2.367–3.410% crude protein, and 6.781–8.314% crude fiber. Okra was determined to have high nutritional value, with γ-tocopherol and α-tocopherol contents about 2.67 mg/100 g and 1.62 mg/100 g, respectively. High-performance liquid chromatography (HPLC) was performed to determine the sugars present in okra aqueous extract. The water-soluble polysaccharide content was 10.22–16.45 g/100 g. The tested aqueous extract was a rich source of total phenolic compounds in gallic acid equivalents (288.2–3426.2 mg/100 g), chlorophyll a (3.53 mg/100), chlorophyll b (2.43 mg/100), and carotenoids (1.3 mg/100 g). The detected minerals were Ca, Mg, Cu, Zn, Fe, K, Na, and Mn. Atomic absorption spectrometry analysis of these ashed minerals was performed. In addition to the nutritional benefits, okra pods exhibited antimicrobial, anticancer, and antioxidant properties. The aqueous extract was found to be potentially active against bacterial strains of Staphylococcus aureus (MIC value = 21.8 mg/mL), Escherichia coli (MIC value = 18.7 mg/mL), Bacillus cereus (MIC value = 20.7 mg/mL), and Klebsiella pneumoniae (MIC value = 20.2 mg/mL). Okra aqueous extract exhibited inhibitory activity against α-amylase (IC50 = 120 µg/mL) and α-glucosidase (IC50 = 115 µg/mL). The okra extract exhibited high anticancer activity, concentration-dependent and with an IC50 value of about 158.3 mg/mL. The results indicated that okra pods have nutritional and medicinal properties and, hence, can be used as a functional food and broad-spectrum nutraceutical supplement.
... The strong association of lemon aroma with model 9 was also unexpected, as lemon aroma is associated with limonene [49]. Limonene was not used in this study. ...
Article
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Cis-Rose oxide was found to be an important chiral compound in Gewürztraminer wine, with an enantiomeric ratio range from 76 to 58%. The enantiomeric ratio showed an important influence on white wine aroma when other monoterpenes were present. The aim of this study was to evaluate rose oxide at different ratios and changes to aroma perception, and the interaction of rose oxide with linalool and α-terpineol. A wine model was made based on Gewürztraminer wine. Twelve models were created with different ratios of rose oxide and concentrations of linalool and α-terpineol. Triangle tests, check-all-that-apply (CATA) and descriptive analysis were used to evaluate the aroma of the wines. Results show that the rose oxide ratios of 70:30 and 65:35 were statistically different. Additional descriptive analysis showed that the ratios altered aroma when linalool and α-terpineol were at low and medium concentrations. At high concentrations, linalool and α-terpineol masked any influence from rose oxide. Understanding how monoterpenes alter aroma perception of white wine when at different combinations and concentrations is important to achieving desired wine qualities and helps provide information on how flavor chemistry results can be interpreted without having to run sensory analysis.
... Recently, studies have shown that D-limonene (LIM), a natural monocyclic monoterpene widely found in citrus fruits, has powerful antioxidant and anti-inflammatory properties (Roberto et al., 2010;Santana et al., 2020;Vieira et al., 2018). In addition, Hirota et al. (2010) demonstrated that it anti-inflammatory effects involves cytokines and reactive oxygen species (ROS) inhibition and inactivation of eosinophil migration (Hirota et al., 2010). ...
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Background Despite some advances in the discovery of novel therapies, smoke inhalation injury remains a difficult to treat critical health issue due to its physiopathological complexity. Natural products, such as D-limonene (LIM), are becoming an important potential source of new treatments in many health problems. LIM has been shown to have antioxidant, anti-inflammatory and protective effects in respect of several diseases, including respiratory conditions Objective The aim of this study was to evaluate the effects of inhaled LIM on acute smoke-induced lung injury in rats Methods Thirty minutes after smoke inhalation, adult male Wistar rats were treated with vehicle or LIM (0.01 mg/kg) for 30 min. Blood samples, and the liver, lungs, and trachea were collected for analysis Results The results showed that LIM minimized the injuries, reducing oxidative and inflammatory damage by improving catalase (CAT) (p < 0.05), and superoxide dismutase (SOD) activities (trachea: p < 0.01; lung: p < 0.05) and reducing interleukin-1 beta (IL-1β) level (p < 0.01) caused by smoke inhalation. LIM was also able to ameliorate damage in both trachea and lung tissues Conclusions The results indicate that LIM has a beneficial effect on lung injury, mainly by reducing oxidative stress, anti-inflammatory response and histological damage.
... Electrospinning process Pullulan and βcyclodextrin [58] High amount of retention of limonene in freeze-drying might be achieved by homogenising the emulsion containing gum Arabic-sucrose-gelatin (1:1:1) at a single stage pressure of 100 MPa. Table 3 Effects and mechanisms of limonene in vitro and in vivo assay [85] References Mechanisms Assay Model Effect [86] Decreased thiobarbituric acid reactive substances (TBARS), enhanced superoxide dismutase, catalase, glutathione peroxidase, and glutathione transferase Streptozotocin-induced diabetes in Wistar rats In vivo Antioxidant activity [87] Inhibition of glycation by stabilizing protein structure through hydrophobic interactions Bovine serum albumin In vitro Antidiabetic activity [88] Lowered the expression of inducible nitric oxide synthase (iNOS), cyclooxygenase (COX), the production of prostaglandin E 2 (PGE 2 ) and the levels of interleukin 1 beta (IL-1β), interleukin 5 (IL-6), and tumor necrosis factor alpha (TNF-α) RAW 264.7 macrophages In vitro [89] Inhibited nitric oxide (NO) production, nuclear factor kappa B (NF-κB) and p38 activation, and decreased iNOS expression [92] Healing effect on stomach ulcer by enhancing cell proliferation, angiogenesis, and PGE 2 production Acetic acid-induced gastric ulcers in Wistar rats ...
... In particular, d-limonene (LIM), a monocyclic monoterpene present in a number of plants, and especially in essential oils extracted from the peel of citrus fruits such as lemons and oranges. LIM has been shown to have gastroprotective, antiarrhythmic, anti-inflammatory and analgesic properties (Araújo do Nascimento et al., 2019;Araújo-Filho et al., 2017a;Vieira et al., 2018), and an interesting substance with potential for study in respect of the reduction of orofacial pain. However, LIM is hydrophobic and susceptible to oxidative degradation, impairing its pharmaceutical applicability (Li and Chiang, 2012). ...
Article
Background Chronic orofacial pain is a serious public health problem with a prevalence of 7-11% in the population. This disorder has different etiologies and characteristics that make pharmacological treatment difficult. Natural products have been shown to be a promising source of treatments for the management of chronic pain, as an example the terpenes. Purpose The aim of this study was to evaluate the anti-nociceptive and anti-inflammatory effects of one of these terpenes, d-limonene (LIM - a common monoterpene found in citrus fruits) alone and complexed with hydroxypropyl-β-cyclodextrin (LIM/HPβCD) in preclinical animal models. Methods Orofacial pain was induced by the administration of hypertonic saline on the corneal surface, the injection of formalin into the temporomandibular joint (TMJ), or chronic constriction injury of the infraorbital nerve (CCI-IoN). The study used male Wistar rats and Swiss mice treated with LIM (50 mg/kg), LIM/HPβCD (50 mg/kg), vehicle (control), gabapentin or morphine, and eyes wiping (induced by hypertonic saline), face rubbing (formalin-induced in TMJ) or mechanical hyperalgesia (provoked by CCI-IoN) were assessed. Additionally, ELISA was used to measure TNF-α, and western blot analysis to assess levels of PKAcα, NFκB, p38MAPK and phosphorylated PKC substrates. Serum levels of aspartate aminotransferase (AST) and alanine transferase (ALT) were also evaluated. Results LIM and LIM/HPβCD significantly reduced (p<0.001) corneal nociception and formalin-induced TMJ nociception. In addition, both substances attenuated (p<0.001) mechanical hyperalgesia in the CCI-IoN model. The antinociceptive effect induced by LIM and HPβCD/LIM was associated with decreased TNF-α levels, downregulation of the NFκB and p38MAPK signalling pathways and reduced PKC substrate phosphorylation and PKA immunocontent. Moreover, the results demonstrated that complexation with HPβCD was able to decrease the therapeutic dose of LIM. Conclusion LIM was found to be a promising molecule for the treatment of orofacial pain due to its capacity to modulate some important mediators essential to the establishment of pain, and HPβCD can be a key tool to improve the profile of LIM.
... Coriander EO exhibited anti-inflammatory effects in an in vivo model of colitis as determined by histo-pathologic evaluation and myeloperoxidase activity [72]; meanwhile, its main constituent linalool was found to inhibit the production of pro-inflammatory cytokines (e.g., TNF-α, IL-1β, IL-6, IL-8) in both in vitro and in vivo settings [73,74]. Caraway EO has shown a protective activity in animal models of colitis and renal injury by the inhibition of cytokine production and the induction of endogenous antioxidant enzymatic systems [75,76]; its beneficial effects are mostly due to limonene and carvone as revealed by various in vitro and in vivo studies [77][78][79]. As for anise EO, it has proven in vitro anti-inflammatory propensities by the inhibition of IL-1β and IL-8 secretion in a bronchial epithelial cell line [80], while its main constituent, anethole was shown to decrease IL-6 and TNF-α serum concentrations in an animal model of chronic and obstructive pulmonary disease [81]. ...
Article
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Dermatophyte infections represent an important public health concern, affecting up to 25% of the world's population. Trichophyton rubrum and T. mentagrophytes are the predominant der-matophytes in cutaneous infections, with a prevalence accounting for 70% of dermatophytoses. Although terbinafine represents the preferred treatment, its clinical use is hampered by side effects, drug-drug interactions, and the emergence of resistant clinical isolates. Combination therapy, associating terbinafine and essential oils (EOs), represents a promising strategy in the treatment of der-matophytosis. In this study, we screened the potential of selected Apiaceae EOs (ajowan, coriander, caraway, and anise) to improve the antifungal activity of terbinafine against T. rubrum ATCC 28188 and T. mentagrophytes ATCC 9533. The chemical profile of EOs was analyzed by gas chromatography. The minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) of EOs/main compounds were determined according to EUCAST-AFST guidelines, with minor modifications. The checkerboard microtiter method was used to identify putative synergistic combinations of EOs/main constituents with terbinafine. The influence of EOs on the viability and pro-in-flammatory cytokine production (IL-1β, IL-8 and TNF-α) was determined using an ex vivo human neutrophils model. The binary associations of tested EOs with terbinafine were found to be syner-gistic against T. rubrum, with FICI values of 0.26-0.31. At the tested concentrations (6.25-25 mg/L), EOs did not exert cytotoxic effects towards human neutrophils. Anise EO was the most potent in-hibitor of IL-1β release (46.49% inhibition at 25 mg/L), while coriander EO displayed the highest inhibition towards IL-8 and TNF-α production (54.15% and 54.91%, respectively). In conclusion, the synergistic combinations of terbinafine and investigated Apiaceae EOs could be a starting point in the development of novel topical therapies against T. rubrum-related dermatophytosis.
... It has anti-inflammatory, antioxidant, and anticancer properties. It is commonly used as a natural food flavoring [17]. -Trans-anethole (trans-1-methoxy-4-propenyl-benzene), which is the main component of EOs extracted from more than 20 species including fennel, anise, and star anise. ...
Article
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Obesity is a complex disease caused by an excessive amount of body fat. Obesity is a medical problem and represents an important risk factor for the development of serious diseases such as insulin resistance, type 2 diabetes, cardiovascular disease, and some types of cancer. Not to be overlooked are the psychological issues that, in obese subjects, turn into very serious pathologies, such as depression, phobias, anxiety, and lack of self-esteem. In addition to modifying one’s lifestyle, the reduction of body mass can be promoted by different natural compounds such as essential oils (EOs). EOs are mixtures of aromatic substances produced by many plants, particularly in medicinal and aromatic ones. They are odorous and volatile and contain a mixture of terpenes, alcohols, aldehydes, ketones, and esters. Thanks to the characteristics of the various chemical components present in them, EOs are used in the food, cosmetic, and pharmaceutical fields. Indeed, it has been shown that EOs possess great antibiotic, anti-inflammatory, and antitumor powers. Emerging results also demonstrate the anti-obesity effects of EOs. We have examined the main data obtained in experimental studies and, in this review, we summarize the effect of EOs in obesity and obesity-related metabolic diseases.
... Through a decrease in β-hydroxy β-methylglutaryl-CoA (HMG-CoA) reductase activity and restoration of malondialdehyde (MDA) values, limonene had a lipid-lowering effect and alleviated cardiovascular disease caused by oxidative stress. It was also shown that limonene consumption decreased the oxidation of low-density lipoprotein (LDL), small dense low-density lipoprotein (sd-LDL), and large-buoyant low-density lipoprotein (lb-LDL) [46]. Squalene and diterpenoid (trans-geranylgeran) were present up to 5%. ...
Article
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Edible oils play a tremendous role in the human diet. The production and consumption of edible oils have extensively increased due to their nutritional and economic significance. As a result of exponential population growth, the demand for edible oil has prompted adulteration, which has become a global crisis. Adulteration causes a variation in the fatty acid profiles, unique to each oil. The addition of adulterants is associated with gallbladder cancer, epidemic dropsy, cardiovascular diseases, hypercholesterolemia, and several other life-threatening diseases. Hence, monitoring the purity of edible oils at regular intervals has become inevitable. This study is to evaluate the quality of edible oils such as sesame, groundnut, coconut, mustard, sunflower, soybean, and olive oils by screening their fatty acids and secondary metabolites composition using gas chromatography-mass spectrometry (GC–MS) and thereby identifying the adulterants in comparison between the unrefined and refined oils. The fatty acid profiles of the unrefined oils were found to be in accordance with the literature survey, whereas the commercially available refined oils were mainly adulterated with palmitic, palmitoleic, stearic, and myristic acids. Contrastingly, numerous health-promoting secondary metabolites have been detected in unrefined oil samples. In conclusion, unrefined oils have nutritional values, and authenticity used for human consumption rather than refined edible oils.
... Limonene is also an outstanding monoterpene, which can be easily perceived by its citrusy smell. This compound can be used to prevent many human disorders due to its anti-inflammatory, antioxidant, antiviral, anti-diabetic, and anticancer properties [25]. Another common monoterpene is sabinene, which has been acknowledged as having antimicrobial, antioxidant, angiostatic, and anti-angiogenic effects [26]. ...
Article
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Essential oils (EOs) of Clausena indica fruits, Zanthoxylum rhetsa fruits, and Michelia tonkinensis seeds were analyzed for their phytochemical profiles and biological activities, including anti-diabetes, anti-gout, and anti-leukemia properties. Sixty-six volatile compounds were identified by gas chromatography–mass spectrometry (GC–MS), in which, myristicin (68.3%), limonene (44.2%), and linalool (49.3%) were the most prominent components of EOs extracted from C. indica, Z. rhetsa, and M. tonkinensis, respectively. In addition, only EOs from C. indica inhibited the activities of all tested enzymes comprising α-amylase (IC50 = 7.73 mg/mL), α-glucosidase (IC50 = 0.84 mg/mL), and xanthine oxidase (IC50 = 0.88 mg/mL), which are related to type 2 diabetes and gout. Remarkably, all EOs from C. indica, Z. rhetsa (IC50 = 0.73 mg/mL), and M. tonkinensis (IC50 = 1.46 mg/mL) showed a stronger anti-α-glucosidase ability than acarbose (IC50 = 2.69 mg/mL), a known anti-diabetic agent. Moreover, the growth of leukemia cell Meg-01 was significantly suppressed by all EOs, of which, the IC50 values were recorded as 0.32, 0.64, and 0.31 mg/mL for EOs from C. indica, Z. rhetsa, and M. tonkinensis, respectively. As it stands, this is the first report about the inhibitory effects of EOs from C. indica and Z. rhetsa fruits, and M. tonkinensis seeds on the human leukemia cell line Meg-01 and key enzymes linked to diabetes and gout. In conclusion, the present study suggests that EOs from these natural spices may be promising candidates for pharmaceutical industries to develop nature-based drugs to treat diabetes mellitus or gout, as well as malignant hematological diseases such as leukemia.
... Limonene is a monoterpene of secondary metabolism mainly in plants of the genus Citrus [28]. It is found in the R-(+)-limonene and S-(-)-limonene isoforms [29]. ...
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Brazilian fish farming goes together with the emergence of numerous bacterial diseases, with Aeromonas hydrophila being the main bacterial pathogen. As a consequence, antimicrobials are excessively used. Considering that antimicrobials are relatively stable and nonbiodegradable, medicinal plants and their phytochemicals have been used as alternative treatments of bacteriosis in fish farming. Limonene is a monoterpene available in two enantiomers: R-(+)-limonene and S-(-)-limonene. This study analyzed the antibacterial activity of the phytochemicals S-(-)-limonene and R-(+)-limonene against some bacteria isolated from silver catfish (Rhamdia quelen). Furthermore, by means of spectrophotometry and atomic force microscopy, we also investigated the combination therapy of phytochemicals with antimicrobials and their activity in terms of inhibiting biofilm formation. Six clinical isolates and a standard strain were selected for antimicrobial activity testing. Biofilm formation was tested in 96-well plates and nylon cubes. The most sensitive of the strains tested was the A. hydrophila strain (MF 372510). S-(-)-limonene and R-(+)-limonene had high minimum inhibitory concentrations; however, they strongly inhibited A. hydrophila biofilm formation. R-(+)-limonene and S-(-)-limonene had an additive effect when combined with florfenicol and an antagonistic effect with oxytetracycline. In general, the phytochemicals tested showed strong antibiofilm activity against A. hydrophila, and when in combination therapy with florfenicol, they showed an additive effect against the treatment of A. hydrophila.
... For instance, carvone was identified as an effective potato sprout inhibitor [20] that accounts for the flavor and antiflatulence characteristics of dill [8]. Furthermore, limonene possesses a pleasant lemon flavor and is used as an antibacterial additive in common foods (e.g., fruit juices, sweets, and ice cream), and it is easily digested and absorbed by the GI tract [21,22]. ...
Article
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Fennel and dill are widely used as food additives owing to their various biological activities, such as antioxidants, antimicrobials, food-preservatives, and seasoning capacities. Herein, the nutritional composition and essential oil (EO) chemical profiles of fruits, umbels, stalks, and roots from one dill and two fennel cultivars were evaluated. The fruits had the highest content of crude protein (≥ 15%), crude fat (≥ 8%), and phosphorus (≥ 0.5%), and exhibited the highest total energy (≥ 20 MJ/kg) and EO yield (≥ 2%). Moreover, estragole (86.56% in Fdf), anethole (71.17% in Fhf), fenchone (16.74% in Fhf), limonene (50.19% in Agf), and carvone (42.41% in Agf) were the main components of the EOs generated from the fruits. The chemical profiles of EOs in the roots were significantly different from those of the aerial parts of the fennel and dill; thus, the roots and aerial parts could be distinguished based on myristicin (Variable Importance in Projection (VIP) = 1.90399) and apiol (VIP = 1.85922). The EO components of the aerial parts varied remarkably, and the chemical markers for differentiating these three cultivars were anethole (VIP = 1.36571), estragole (VIP = 1.30292), and carvone (VIP = 1.11947). Overall, our results provide a noteworthy chemical basis for further development of fennel and dill, especially as food additives.
... In cosmetics formulation, it is one of the wellknown cheap and frequently used fragrances. It can exist in different types of beauty products like shower gels, hair conditioners, shampoos, perfumes, and soaps (Vieira et al. 2018). Linalool is a monoterpene, which is found naturally in more than 200 oils derived from wood, flowers, leaves, and herb (Gershenzon and Dudareva 2007). ...
Chapter
In recent years, the interest of consumers around the world is increasing toward the use of herbal products for personal and beauty care. Essential oils (EOs) play a major role in cosmetic and personal health care industries. EOs are natural fragrance liquid that contains a natural chemical, which imparts the plants its essence. They have been isolated from different forest-based and elsewhere available plant species. Usually, they are obtained from different plant parts such as leaves (Cymbopogon jwarancusa and Cymbopogon citratus), flower (Lavandula angustifolia and Salvia rosmarinus), bark (Canella winterana and Cassia cinnamon), wood (Santalum album), roots (Valeriana officinalis, and Sassafras albidum), seeds (Myristica fragrans and Anethum graveolens), and fruits (Juniperus communis, Citrus limon, Citrus sinensis, and Citrus bergamia). The chemical composition of EOs may differ depending on the geographical location, climatic conditions, plant species, and so on. These oils find their application in cosmetic products, shampoo, soap, perfume, detergents, etc. Currently, approximately 3000 EOs are known; among this 17,500 aromatic flora or plants possess EOs. Some of the main plant families that contain EOs are Lamiaceae, Rutaceae, Myrtaceae, Zingiberaceae, and Asteraceae. This chapter provides an overview of the role of forest-based and elsewhere available plant species in terms of EOs production and their cosmetic and personal health care applications.
... Anti-inflammatory [64][65][66][67][68][69] Anticancer [64,65,70,71] Sedative [68,72,73] Limonene Anticancer [74][75][76][77][78] Anti-inflammatory [41,78] Terpinolene Anticancer [79] Anti-inflammatory [41,80] β-Pinene ...
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Multiple positive effects that forests have on human health and overall well-being have been reported widely in the literature. Still, multiple elements of this relationship remain unidentified and unexplained. In this study, the composition of leaf volatile organic compounds (BVOCs) content in three common coniferous species: the Austrian pine (Pinus nigra), Scots pine (Pinus sylvestris) and Spruce (Picea abies), was analyzed. The specificity of BVOCs content in the examined species and their genotypes is observed as a plant potential to evaporate these organic compounds and potentially improve human health and well-being. Principal component analysis applied on BVOCs content among species showed significant differences between compounds that have previously been characterized as having positive effects on human health by acting as anticancer, anti-inflammatory, antiviral and antibacterial. Variations among genotypes of the investigated species were observed in the content of BVOCs relevant for human health improvement, such as limonene, terpinolene, β-pinene, linalool, camphene, camphor, citronellol and α-cadinol. The observed intra- and inter-species variations in the BVOCs content provide an appropriate base for further research on the forest–human health relationship, breeding and selection of the most suitable genotypes for human health improvement, and could I mpact the sustainable management of forests.
... One possible explanation is the presence of many components which were identified in the leaf volatile oil only and reported to possess promising anti-inflammatory activity. For example; b-Ionone (Kang et al., 2013), Limonene which exerted promising anti-inflammatory activity either in vivo or in vitro (Vieira et al., 2018;de Souza et al., 2019), Phytol which was proved to attenuate the inflammatory response by decreasing the levels of proinflammatory cytokines (tumor necrosis factor-a (TNF-a) and interleukin-1b) and inhibiting neutrophil migration , and squalene which was proved to reduce intracellular levels of proinflammatory cytokines and pro-inflammatory enzymes with enhanced expression of the anti-inflammatory enzyme haem oxygenase-1 (HO-1) (C ardeno et al., 2015). These findings might suggest a synergistic effect between different components of leaf volatile oil with higher contribution of specific components to this activity. ...
Article
Brownea species were used in folk medicine for the treatment of tuberculosis in South America. Volatile oils prepared by hydro-distillation from fresh leaves and stems of Brownea grandiceps Jacq. (Fabaceae) collected in different seasons were analyzed separately by GC/MS. The anti-mycobacterial and anti-inflammatory activities of the volatile oils were also assessed. A total of 60 compounds were identified in the leaves and stems volatile oils accordingly. The most abundant components were methyl salicylate (53.06% - 9.56%), hexanal (38.27% - 0.26%), n-nonacosane (21.23% - 0.46%) and (E)-2-hexenal (31.2%- 0.91%). Results revealed a remarkable influence of the season of collection on the yield and chemical composition of the obtained oils. The leaf volatile oil exerted higher anti-mycobacterial and anti-inflammatory effects compared to stem volatile oil. The leaf volatile oil showed remarkable inhibition of M. tuberculosis ATCC 27294 (MIC 3.9 μg/mL) comparable to standard isoniazid. It also exerted a promising membrane stabilizing anti-inflammatory effect (IC50 value of 27.1 μg/mL) comparable to methyl salicylate and standard indomethacin. From these findings, it may be concluded that the leaf volatile oil represents a promising anti-mycobacterial and anti-inflammatory agent. To the best of our knowledge, the present study describes the first to characterize B. grandiceps volatile oils and to emphasize the great promise for treatment of tuberculosis and inflammatory disorders.
... Limonene (lmn) was one of the most evaluated compounds in the three variables considered in Figure 12, being a terpene present in several Citrus EOs, such as Citrus sinensis, which is a source of EOs with antibacterial activity against several foodborne pathogens (Evangelho et al., 2019;Vieira et al., 2018), followed by 1,8-cineole (cnl), αpinene (α-pin), thymol (thy), and carvacrol (crv), mainly related to antimicrobial variables. The presence of compounds such as thymol and carvacrol is highly associated with the antioxidant and antimicrobial activities of EOs in the literature, being some of the main active compounds that effectively inhibit the growth of bacteria and fungi (Bhavaniramya et al., 2019;Braga et al., 2006;Knobloch et al., 1985;Tariq et al., 2019); 1,8-cineole and α-pinene are also useful, they have less activity (Can Başer & Buchbauer, 2015;Mohamed et al., 2013). ...
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Essential oils (EOs) are commercially important products, sources of compounds with antioxidant and antimicrobial activities considered indispensable for several fields, such as the food industry, cosmetics, perfumes, pharmaceuticals, sanitary and agricultural industries. In this context, this systematic review and meta-analysis, a novel approach will be presented using chemometric tools to verify and recognize patterns of antioxidant, antibacterial, and antifungal activities of EOs according to their geographic, botanical, chemical, and microbiolog-ical distribution. Scientific papers were selected following the Preferred Reporting Items for Systematic Review and Meta-Analyses statement flow diagram, and the data were evaluated by the self-organizing map and hierarchical cluster analysis. Overall, this novel approach allowed us to draw an overview of antioxidants and antimicrobials activities of EOs reported in 2019, through 585 articles evaluated , obtaining a dataset with more than 10,000 data, distributed in more than 80 countries, 290 plant genera, 150 chemical compounds, 30 genera of bacteria, and 10 genera of fungi. The networks for geographic, botanical, chemical, and microbiological distribution indicated that Brazil, Asia, the botanical genus Thymus, species Thymus vulgaris L. "thyme," the Lamiaceae family, limonene, and the oxygenated monoterpene class were the most representative in the dataset, while the species Escherichia coli and Candida albicans were the most used to assess the antimicrobial activity of EOs. This work can be seen as a guide for the processing of metadata using a novel approach with non-conventional statistical methods. However, this preliminary approach with EOs can be extended to other sources or areas of food science.
... Limonene, a common monoterpene found as major component of the active complex of the genus Citrus [15], has been shown to exert anxiolytic, antinociceptive, antioxidant, and anti-inflammatory activity [16][17][18][19][20], as well as to display a protective effect against metabolic syndromes and gastrointestinal and respiratory tract diseases [21,22]. Interestingly, limonene has been suggested to act on the central nervous system, affecting the expression of adenylate cyclase 1 [15], which has been demonstrated to regulate cAMP levels. ...
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Many natural-derived compounds, including the essential oils from plants, are investigated to find new potential protective agents in several neurodegenerative disorders such as Alzheimer’s disease (AD). In the present study, we tested the neuroprotective effect of limonene, one of the main components of the genus Citrus, against the neurotoxicity elicited by Aβ1-42 oligomers, currently considered a triggering factor in AD. To this aim, we assessed the acetylcholinesterase activity by Ellman’s colorimetric method, the mitochondrial dehydrogenase activity by MTT assay, the nuclear morphology by Hoechst 33258, the generation of reactive oxygen species (ROS) by DCFH-DA fluorescent dye, and the electrophysiological activity of KV3.4 potassium channel subunits by patch-clamp electrophysiology. Interestingly, the monoterpene limonene showed a specific activity against acetylcholinesterase with an IC50 almost comparable to that of galantamine, used as positive control. Moreover, at the concentration of 10 µg/mL, limonene counteracted the increase of ROS production triggered by Aβ1-42 oligomers, thus preventing the upregulation of KV3.4 activity. This, in turn, prevented cell death in primary cortical neurons, showing an interesting neuroprotective profile against Aβ1-42-induced toxicity. Collectively, the present results showed that the antioxidant properties of the main component of the genus Citrus, limonene, may be useful to prevent neuronal suffering induced by Aβ1-42 oligomers preventing the hyperactivity of KV3.4.
... Cobrançosa (Portuguese cultivar) olive leaf at different harvesting times. Limonene is a common constituent of various plant essential oils ant it has been found to have numerous medicinal benefits (antioxidant properties, an excellent dietary source for cancer prevention and a slight cytotoxic activity toward normal cells) demonstrated both in human and animal studies [33][34]. ...
... This substance is reported in the literature as having antibacterial and antifungal activity against foodborne pathogens [29,30]. In the food industry, for example, it can be used as an inhibitor of yeast growth during the fermentation process [31], and, in addition, this component also presents anti-inflammatory, antioxidant and anticancer activities [32]. Another major component found in the essential oil of the EflA specimen was the oxygenated sesquiterpene spathulenol (10.94%), which was also observed in the EflB specimen (1.2%). ...
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Eugenia florida DC. belongs to the Myrtaceae family, which is present in almost all of Brazil. This species is popularly known as pitanga-preta or guamirim and is used in folk medicine to treat gastrointestinal problems. In this study, two specimens of Eugenia florida (Efl) were collected in different areas of the same region. Specimen A (EflA) was collected in an area of secondary forest (capoeira), while specimen B (EflB) was collected in a floodplain area. The essential oils (EOs) were extracted from both specimens of Eugenia florida by means of hydrodistillation. Gas chromatography coupled to mass spectrometry (GC/MS) was used to identify the volatile compounds present, and the antioxidant capacity of the EOs was determined by antioxidant capacity (AC-DPPH) and the Trolox equivalent antioxidant (TEAC) assay. For E. florida, limonene (11.98%), spathulenol (10.94%) and α-pinene (5.21%) were identified as the main compounds of the EO extracted from sample A, while sample B comprised selina-3,11-dien-6α-ol (12.03%), eremoligenol (11.0%) and γ-elemene (10.70%). This difference in chemical composition impacted the antioxidant activity of the EOs between the studied samples, especially in sample B of E. florida. This study is the first to report on the antioxidant activity of Eugenia florida DC. essential oils.
... In this category, a variation of two to six plants were observed in associated mixtures, with the presence of Citrus limon and Eucalyptus globulus standing out as the most indicated. The leaves (15) were prominent amongst the different plant parts (fruit, sap, bark, root and whole plant) most commonly used in the preparation of decoctions (Lemos et al., 2016;Vieira et al., 2018). The mixtures for this system were not repeated for any disease and also did not reach a consensus among the informants (ICF = 0.00). ...
Article
Introduction The use of mixtures of medicinal plants, when compared to the therapeutic objective of a particular plant, can show greater effectiveness in the cure or treatment of disorders or potentiate harmful effects to an organism. The present study aimed to verify the indications of medicinal plants, alone and in association. Methods Ethnobotanical information was obtained through semi-structured interviews, using the snowball technique, collecting information related to preparation, part of the plant used and therapeutic purposes of the mixtures. Results The experts highlighted a total of 58 mixtures indicated for 41 diseases grouped into ten body systems, among which respiratory system disorders covered a more significant number of mixtures (28) and obtained the second largest consensus among the informants (ICF = 0.44). Symptoms in this category included flu and cough with higher indications and higher frequency of use in associations for Plectranthus amboinicus (Lour.) Spreng. The Index of Taxon Usefulness in Mixtures (ITUM) ranged from 0.14 to 1.00. A total of 14 species showed values equal to 1.00, observed only in mixtures, highlighting Allium cepa L. with more indications of use. The mixtures showed no toxicity in the study. However, it is possible to observe some species with individual use that may confer antagonistic effects depending on their administration and dosage. Conclusions Therefore, the results of this research show that the mixtures most used by the community are prepared with an association of two to three plants. The mixtures have more restricted indications of use, demonstrating specificity in the treatment of illness. Further pharmacological bioprospecting studies are needed to confirm and validate the therapeutic benefit of these medicinal plant associations.
... Monoterpenes amounted for 3-7 % of the total volatiles in cruciferous leaves, with the highest level in cauliflower at 7.7%. Limonene (peak 153) a key compound of citrus oil, with a pleasant lemon-like aroma (Vieira, Beserra, Souza, Totti, & Rozza, 2018) was the major monoterpene. Unlike mono, sesquiterpenes were detected at trace levels in all cruciferous specimens represented by -caryophyllene and its isomer (peaks 176 & 178) suggestive that monoterpene biosynthesis is more activated in cruciferous leaves than sesquiterpenes. ...
Article
Cruciferous vegetables, also known as brassicaceae vegetables, are widely consumed worldwide for their nutritive and substantial health benefits. Compositional heterogeneity was explored in six cruciferous vegetables viz, cauliflower, turnip, broccoli, watercress, radish and cabbage leaves targeting their aroma and nutrients profile. A headspace solid-phase micro extraction (HS-SPME) technique combined with gas chromatography-mass spectrometry (GC-MS) was employed for metabolite profiling. Results revealed extensive variation in volatiles and nonvolatile profiles among the six cruciferous vegetables. A total of 55 nutrient metabolites were identified, whereas a total of 190 volatiles were detected. Aldehydes and ketones appeared as the most discriminatory among leaves, accounting for its distinct aroma. Furthermore, chemometric analysis of both datasets showed clear classification of the six vegetables, with several key novel markers. This study provides the first comparative study between edible and inedible parts of cruciferous vegetables, suggesting novel uses as functional foods.
... Anethole has been analyzed for its antimicrobial, antifungal, anti-inflammatory, mutagenic, and cytotoxic activities [35,36]. Limonene exhibits antibacterial and cytotoxic activities [37]. Similarly, β-caryophyllene also possesses antibacterial, antioxidant, anti-inflammatory, and anticarcinogenic activities [36]. ...
... The presence of aliphatic alcohols 1,3-butanediol (7.26%) and 2,3-butanediol (5.16%) suggests likely microbial fermentation of sugars abundant in the citrus peel (note that, in the case of C. aurantium, the fruits were not squeezed and the peel was removed by hand) [36]. Anti-inflammatory, antidiabetic, antioxidant, and anticarcinogenic limonene [37], in its turn, is by far the dominant volatile molecule of red orange IntegroPectin, with a percentage approaching 91%. For comparison, α-terpineol and terpinen-4-ol are the dominant terpenes in lemon IntegroPectin [5], whereas α-terpineol and linalool are the dominant terpenes in grapefruit IntegroPectin [5]. ...
Article
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DRIFT, HPLC-MS, and SPME-GC/MS analyses were used to unveil the structure and the main functional compounds of red (blood) orange (Citrus sinensis) and bitter orange (Citrus aurantium). The IntegroPectin samples show evidence that these new citrus pectins are comprised of pectin rich in RG-I hairy regions functionalized with citrus biophenols, chiefly flavonoids and volatile molecules, mostly terpenes. Remarkably, IntegroPectin from the peel of fresh bitter oranges is the first high methoxyl citrus pectin extracted via hydrodynamic cavitation, whereas the red orange IntegroPectin is a low methoxyl pectin. C. aurantium IntegroPectin has a uniquely high concentration of adsorbed flavonoids, especially the flavanone glycosides hesperidin, naringin, and eriocitrin.
... In C. sinensis EO, trans-p-2,8-Menthadien-1-ol, cis-limonene oxide, trans-limonene oxide, and trans-carveol were identified as the other four major compounds (5.0, 2.6, 2.3, and 2.9%). Limonene is a colorless terpene with a pleasant lemon-like odor [32,33]. The literature reported a nanoliposome containing limonene with a particle size of 100 nm; however, it was used as an antibacterial agent [34]. ...
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Background Mosquito-borne diseases such as malaria and encephalitis are still the cause of several hundred thousand deaths annually. The excessive use of chemical insecticides for transmission control has led to environmental pollution and widespread resistance in mosquitoes. Botanical insecticides' efficacies improvement has thus received considerable attention recently. Methods The larvicidal effects of three essential oils from the Citrus family and limonene (their major ingredient) were first investigated against malaria and filariasis mosquito vectors. An attempt was then made to improve their efficacies by preparing nanoliposomes containing each of them. Results The larvicidal effect of nanoformulated forms was more effective than non-formulated states. Nanoliposomes containing Citrus aurantium essential oil with a particle size of 52 ± 4 nm showed the best larvicidal activity (LC50 and LC90 values) against Anopheles stephensi (6.63 and 12.29 µg/mL) and Culex quinquefasciatus (4.9 and 16.4 µg/mL). Conclusion Due to the green constituents and high efficacy of nanoliposomes containing C. aurantium essential oil, it could be considered for further investigation against other mosquitoes’ populations and field trials.
... aurantium) flowers are limonene and linalool. D-Limonene shows antidepressant-like effects by influencing the neuroendocrine, neurotrophic, and monoaminergic systems [215]. In a cultivation-based in vitro study with 12 gut bacterial species, the essential oils of lavender and orange blossom showed preferential inhibitory activity against potentially pathogenic gut microorganisms while having a reduced impact on gut microbes regarded as beneficial [88]. ...
... aurantium) flowers are limonene and linalool. D-Limonene shows antidepressant-like effects by influencing the neuroendocrine, neurotrophic, and monoaminergic systems [215]. In a cultivation-based in vitro study with 12 gut bacterial species, the essential oils of lavender and orange blossom showed preferential inhibitory activity against potentially pathogenic gut microorganisms while having a reduced impact on gut microbes regarded as beneficial [88]. ...
Article
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Background: Various neurocognitive and mental health-related conditions have been associated with the gut microbiome, implicating a microbiome-gut-brain axis (MGBA). The aim of this systematic review was to identify, categorize, and review clinical evidence supporting medicinal plants for the treatment of mental disorders and studies on their interactions with the gut microbiota. Methods: This review included medicinal plants for which clinical studies on depression, sleeping disorders, anxiety, or cognitive dysfunction as well as scientific evidence of interaction with the gut microbiome were available. The studies were reported using the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) statement. Results: Eighty-five studies met the inclusion criteria and covered thirty mental health-related medicinal plants with data on interaction with the gut microbiome. Conclusion: Only a few studies have been specifically designed to assess how herbal preparations affect MGBA-related targets or pathways. However, many studies provide hints of a possible interaction with the MGBA, such as an increased abundance of health-beneficial microorganisms, anti-inflammatory effects, or MGBA-related pathway effects by gut microbial metabolites. Data for Panax ginseng, Schisandra chinensis, and Salvia rosmarinus indicate that the interaction of their constituents with the gut microbiota could mediate mental health benefits. Studies specifically assessing the effects on MGBA-related pathways are still required for most medicinal plants.
... Citrus essential oils have been extensively used in food applications and non-food applications such as cosmetics and cleaning as flavoring agents due to their pleasant odor, similar to lemon, which is typical of a low molecular weight terpene called limonene (Asbahani et al., 2015;Ravichandran et al., 2018). Apart from its use as flavor, limonene presents several bioactive properties such as anti-inflammatory, anticancer, antioxidant, antidiabetic, and antimicrobial (Vieira et al., 2018). However, its non-polar character, high volatility, and high susceptibility to oxidation arise as limitations of handling limonene as an ingredient. ...
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In this study, the effects of different concentrations of pea protein concentrate (PPC) in the physical properties, porosity features, and oxidative stability of maltodextrin-based spray-dried microparticles containing orange essential oil (OEO, rich in limonene) were evaluated. The use of PPC resulted in spray-dried microparticles with encapsulation efficiencies of about 99 wt%, without visible pores, and relatively high glass transition temperature (66,4 °C) at Aw ∼ 0.3. The nitrogen adsorption and positron annihilation lifetime spectroscopy measurements showed that the increase of PPC concentration from 2.4 to 4.8 wt% (g of PPC/100 g of emulsion) did not affect the porosity features of the microparticles. These results were confirmed by the profiles of OEO retention and limonene oxide production, which were similar for both samples throughout four weeks of storage. Based on these results, we verified that the lower amount of PPC we tested can effectively protect the OEO during storage, showing that a relatively cheaper orange flavor powder can be produced using less protein.
... Specifically, a significant reason for aromatherapy's effectiveness in treating mood disorders is the presence of desirable chemical components and biological activities in essential oils such as limonene, linalool, linalyl acetate, geraniol, citronellol, and more. These chemicals have been extensively studied and have shown anxiolytic and antidepressant properties (Setzer, 2009;Vieira et al., 2018;Zhang and Yao, 2019;Agatonovic-Kustrin et al., 2020;Soares et al., 2021). ...
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Mood disorders, also often referred to as affective disorders, are a group of psychiatric illnesses that severely impact mood and its related functions. The high medical expenditures have placed a significant financial burden on patients and their families. Aromatherapy is an alternative and complementary treatment that utilizes essential oils (EOs) or volatile oils (VOs) to achieve major therapeutic goals. In general, EOs are volatile chemicals that enter the body primarily through skin absorption and/or nasal inhalation. In addition, they can work through oral administration. Inhalation aromatherapy has shown unique advantages for treating mood disorders, especially depression, anxiety and mental disorders such as sleep disorder, which have been validated over the last decade through clinical and animal studies. Accumulating evidence has shown that EOs or VOs can bypass the blood-brain barrier to target brain tissue through the nasal-brain pathway. Subsequently, they act on the cerebral cortex, thalamus, and limbic system in the brain to improve symptoms of anxiety, depression and improve sleep quality. Here, we review the natural aromatic plants’ volatiles or essential oils used commonly as adjuncts to manage mood disorders and illustrate the mechanisms of inhalation aromatherapy, and mainly summarized the application of transnasal inhalation aromatherapy in depression, anxiety, and sleep disorders. We conclude that aromatherapy does not cause side-effects, which is vastly different from commonly used psychotropic drugs. Inhalation aromatherapy via brain-targeted nasal delivery offers potentially efficacious treatment for mental disorders and merits further study.
... Linarin, the major bioactive substance of C. zawadskii, has been reported to exhibit anti-inflammatory, antioxidant, hepatoprotective, antibacterial, and anticancer activities (31). Limonene, one of major ingredients of peppermint, has been reported to have anti-inflammatory, antioxidant, antibacterial, and anti-cancer effects (32). A previous study has shown that glycyrrhetinic acid exhibits anti-inflammatory effects through NO scavenging in LPS-stimulated RAW264.7 cells (33). ...
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The normal inflammatory reaction protects the body from harmful external factors, whereas abnormal chronic inflammation can cause various diseases, including cancer. The purpose of the present study was to investigate the anti‑inflammatory activity of a mixture of Chrysanthemum zawadskii, peppermint and Glycyrrhiza glabra (CPG) by analyzing the expression levels of inflammatory mediators, cytokines and transcription factors in lipopolysaccharide (LPS)‑stimulated Raw264.7 cells. A nitric oxide assay, ELISA, western blotting and immunofluorescence staining were performed to investigate the anti‑inflammatory activity of the CPG mixture. Pretreatment of Raw264.7 cells with CPG inhibited the increase of inflammatory mediators (inducible nitric oxide synthase, cyclooxygenase‑2 and IFN‑β) induced by LPS. Additionally, it inhibited the production of pro‑inflammatory cytokines (TNF‑α, IL‑6 and IL‑1β). CPG suppressed LPS‑induced phosphorylation of STAT1, AKT, Iκb and NF‑κB. Furthermore, CPG inhibited the translocation of NF‑κB into the nucleus. In summary, CPG could inhibit LPS‑induced inflammation, which occurs primarily through the AKT/Iκb/NF‑κB signaling pathway in RAW264.7 cells.
... Anethole has been analyzed for its antimicrobial, antifungal, anti-inflammatory, mutagenic, and cytotoxic activities [35,36]. Limonene exhibits antibacterial and cytotoxic activities [37]. Similarly, β-caryophyllene also possesses antibacterial, antioxidant, anti-inflammatory, and anticarcinogenic activities [36]. ...
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Known for its high nutritional and medicinal value, okra (Abelmoschus esculentus) is commonly used for replacing plasma and expanding blood volume in humans. It is a major economic crop cultivated in tropical and subtropical regions worldwide. The present study aimed to investigate and evaluate the nutritional properties and prospective applications of the consumable parts of okra. The total ash content (mineral content), carbohydrate, crude fiber, fat, protein, and moisture fractions of okra pod aqueous extract were determined. The results show that okra aqueous extract contained 84.670–87.650% moisture, 1.514–1.197% ash, 7.857–8.261% carbohydrate, 2.367–3.410% crude protein, and 6.781–8.314% crude fiber. Okra was determined to have high nutritional value, with γ-tocopherol and α-tocopherol contents about 2.67 mg/100 g and 1.62 mg/100 g, respectively. High-performance liquid chromatography (HPLC) was performed to determine the sugars present in okra aqueous extract. The water-soluble polysaccharide content was 10.22–16.45 g/100 g. The tested aqueous extract was a rich source of total phenolic compounds in gallic acid equivalents (288.2–3426.2 mg/100 g), chlorophyll a (3.53 mg/100), chlorophyll b (2.43 mg/100), and carotenoids (1.3 mg/100 g). The detected minerals were Ca, Mg, Cu, Zn, Fe, K, Na, and Mn. Atomic absorption spectrometry analysis of these ashed minerals was performed. In addition to the nutritional benefits, okra pods exhibited antimicrobial, anticancer, and antioxidant properties. The aqueous extract was found to be potentially active against bacterial strains of Staphylococcus aureus (MIC value = 21.8 mg/mL), Escherichia coli (MIC value = 18.7 mg/mL), Bacillus cereus (MIC value = 20.7 mg/mL), and Klebsiella pneumoniae (MIC value = 20.2 mg/mL). Okra aqueous extract exhibited inhibitory activity against α-amylase (IC50 = 120 µg/mL) and α-glucosidase (IC50 = 115 µg/mL). The okra extract exhibited high anticancer activity, concentration-dependent and with an IC50 value of about 158.3 mg/mL. The results indicated that okra pods have nutritional and medicinal properties and, hence, can be used as a functional food and broad-spectrum nutraceutical supplement.
... Limonene is a colorless liquid and exists as two optical isomers, d-limonene, which is the main compound in the essential oils of the peels of Citrus spp., and L-limonene, which is mainly found in the essential oils of Pinus and Mentha species. It is considered safe, presenting low toxicity to humans, an excellent solvent for cholesterol, and effective in the treatment of chronic heartburn or gastro-esophageal reflux disorder with an anticancer, antioxidant, and antidiabetic activity [14,15]. ...
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Background: Biofilms have been found growing on implantable medical devices. This can lead to persistent clinical infections. The highly antibiotic-resistant property of biofilms necessitates the search for both potent antimicrobial agents and novel antibiofilm strategies. Natural product-based anti-biofilm agents were found to be as efficient as chemically synthesized counterparts with fewer side effects. In the present study, the effects of limonene as an antibiofilm agent were evaluated on Pseudomonas aeruginosa and Staphylococcus aureus biofilm formed on different surfaces using the CDC model system in continuous flow. The flgK gene and the pilA gene expression in P. aeruginosa, and the icaA gene and eno gene in S. aureus, which could be considered as efficient resistance markers, were studied. Methods: Mono- and dual-species biofilms were grown on polycarbonate, polypropylene, and stainless-steel coupons in a CDC biofilm reactor (Biosurface Technologies, Bozeman, MT, USA). To evaluate the ability of limonene to inhibit and eradicate biofilm, a sub-MIC concentration (10 mL/L) was tested. The gene expression of P. aeruginosa and S. aureus was detected by SYBR Green quantitative Real-Time PCR assay (Meridiana Bioline, Brisbane, Australia). Results: The limonene added during the formation of biofilms at sub-MIC concentrations works very well in inhibiting biofilms on all three materials, reducing their growth by about 2 logs. Of the same order of magnitude is the ability of limonene to eradicate both mono- and polymicrobial mature biofilms on all three materials. Greater efficacy was observed in the polymicrobial biofilm on steel coupons. The expression of some genes related to the virulence of the two microorganisms was differently detected in mono- and polymicrobial biofilm. Conclusions: These data showed that the limonene treatment expressed different levels of biofilm-forming genes, especially when both types of strains alone and together grew on different surfaces. Our findings showed that limonene treatment is also very efficient when biofilm has been grown under shear stress causing significant and irreversible damage to the biofilm structure. The effectiveness of the sanitation procedures can be optimized by applying antimicrobial combinations with natural compounds (e.g., limonene).
... Limonene is one of the most common terpenes, being a major component of many coniferous species, responsible, among others, with the aromatic scents [70]. It is well-known for its several health benefits due to anti-inflammatory, antioxidant, antinociceptive, antiviral and possibly disease-preventing properties [71]. Another interesting compound found in needles is β-caryophyllene, which is known as the first "dietary cannabinoid" approved by the FDA for food use [72], with proved medicinal benefits. ...
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Valorization of renewable biomass forestry gains more and more interest due to the exhaustible nature of fossil based resources and their negative environment impact. Therefore, this study involves thoroughly characterization of bark, needles and cones from silver fir (Abies alba Mill.) of two different ages (40 and 100 years) to determine their potential use as source of valuable compounds. Proximate/ultimate and compositional analysis as well as thermal behavior showed that the studied materials are promising candidates for biomass valorization by torrefaction and pyrolysis. In addition, it was revealed that fir samples contain significant amounts of phenolic and flavonoid compounds. The extractive fractions were found to be rich in highly valuable compounds such as terpenes, paraffins, phenols, acids and derivatives of abietic acid. This induced good antioxidant activity of the extractive fractions, with fast scavenging of DPPH radicals. The PCA and hierarchical clustering used for exploratory data analysis offered the possibility to combine multiple information obtained from detailed characterization of samples into a global view of the system. This allowed us to observe and distinguish similarities and differences among samples according to source and age. Needles stand out from bark and cones due to the high content of terpenes in extractives. Paraffins were the main components in the extractives from cones. Saccharides were found, in small amounts, only in the extractives of bark. Differences by age were also observed. The resulted outcomes provide a promising starting point in selecting suitable sources and procedures for valorization of renewable biomass forestry into energy and value added materials.
... It has been demonstrated that this compound has a number of biological activities such as anticancer (by inducing the natural death of cancer cells and/or inhibiting their cell growth), herbicide, insecticide, in addition to being used as an industrial solvent, as well as a raw material in the manufacture of other chemical compounds, and in the production of pigments, paints, and adhesives. This compound is also used in the pharmaceutical and food industries as an aromatic and flavoring component, being used, for example, to obtain artificial mint and mint flavors, in the manufacturing of candies and chewing gums (Vieira et al., 2018). ...
Article
Antimicrobial resistance has emerged as a health public concern as the combat of resistant microorganisms has become increasingly challenging. Thus, considering the urgent need of developing new therapeutic alternatives, the present study aimed to investigate the chemical composition and evaluate the antimicrobial and drug enhancing potential of the essential oil obtained from the leaves of Piper xylosteoides (Kunth) Steud (EOLPx) against clinically relevant bacterial and fungal strains. Following collection, the leaves were dried at room temperature in a dark environment and the extraction was performed by hydrodistillation using a modified Clevenger-type apparatus. The oil was dried with anhydrous magnesium sulfate, filtered, concentrated in rotary evaporator, and 5 mL aliquots were stored in a refrigerator. The oil yield was expressed as a percentage of the dry weight of the plant material (w/w). The chemical characterization was performed by gas chromatography coupled to mass spectrometry (GC–MS) and flame ionization detector (FID). The antimicrobial analysis was carried out using the broth microdilution and half-maximal inhibitory concentrations (IC50), minimum inhibitory concentrations (MIC), and minimum fungicidal concentrations (MFC) were deterimined by subculture. To evaluate the drug enhancing potential, subinhibitory concentrations (MFC/16 and MIC/8) of the essential oil were combined with the antifungal drug fluconazole and the antibiotics norfloxacin, gentamicin and erythromycin. The impact of the in vitro treatment on fungal virulence was determined by observing morphological transition in wet chambers. The chemical analysis identified the presence of monoterpenes (58.8%) and sesquiterpenes (35.3%), including the monoterpene hydrocarbon myrcene (27.5%) as the major component. The in vitro treatment with the essential oil caused little impact on C. albicans growth, showing a weak fungicidal effect against the URM 4387 strain (at 8192 µg/mL), while the INCQS 40006 strain was not affected. In addition, the association of the EOLPx with fluconazole did not enhance the antifungal effect of this drug against none of the C. albicans strains. However, both the natural product and fluconazole inhibited fungal pleomorphism by both strains. While the essential oil MIC against all bacterial strains was higher than 813 μg/mL, it was found to enhance the activity of gentamicin against the SA and EC isolates as well as to potentiate the activity of erythromycin against the EC isolate. On the other hand, antagonistic effects were observed from its association with norfloxacin for both strains. In conclusion, the EOLPx showed antibiotic-enhancing effects in addition to inhibiting C. albicans morphological transition. Nevertheless, further research is required to better characterize the antimicrobial effects and mechanisms of action by the essential oil components.
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About a century ago when research into the nutritional components of food began, scientists were limited by the technology and physiological understanding of the time. Nonetheless, this pioneering research revealed the importance of many nutrients for the maintenance of life and prevention of overt deficiency diseases. Unfortunately, the necessary simplifications led to the unrecognized assumption that the constituents in food not required for life were not important. This justified growing food chemically rather than organically because essential nutrients were largely (but not entirely) conserved. However, as technology advanced-especially at the turn of this century-much was revealed. Nutrients considered single molecules when discovered were now realized to represent multiple variants and vitamers with significantly different physiological effects, and many of the molecules considered "unimportant" have huge impacts on health and resistance to disease.
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In traditional medicine, Ocimum gratissimum (scent leaf) is used in the treatment of various diseases such as diabetes, cancer, inflammation, anaemia, diarrhoea, pains, and fungal and bacterial infections. The present study reviewed the phytochemicals, essential oils, and pharmacological activities of O. gratissimum. The bioactive compounds extracted from O. gratissimum include phytochemicals (oleanolic acid, caffeic acid, ellagic acid, epicatechin, sinapic acid, rosmarinic acid, chlorogenic acid, luteolin, apigenin, nepetoidin, xanthomicrol, nevadensin, salvigenin, gallic acid, catechin, quercetin, rutin, and kaempfero) and essential oils (camphene, β-caryophyllene, α- and β-pinene, α-humulene, sabinene, β-myrcene, limonene, 1,8-cineole, trans-β-ocimene, linalool, α- and δ-terpineol, eugenol, α-copaene, β-elemene, p-cymene, thymol, and carvacrol). Various in vivo and in vitro studies have shown that O. gratissimum and its bioactive constituents possess pharmacological properties such as antioxidant, anti-inflammatory, anticancer, hepatoprotective, antidiabetic, antihypertensive, antidiarrhoeal, and antimicrobial properties. This review demonstrated that O. gratissimum has a strong preventive and therapeutic effect against several diseases. The effectiveness of O. gratissimum to ameliorate various diseases may be attributed to its antimicrobial and antioxidant properties as well as its capacity to improve the antioxidant systems. However, despite the widespread pharmacological activities of O. gratissimum, further experiments in human clinical trial studies are needed to establish effective and safe doses for the treatment of various diseases.
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This work investigated the extraction of bioactive compounds from citrus peels, an agri‐food waste. Carbon dioxide (CO2), an eco‐friendly solvent, was used under liquid and supercritical conditions to perform the extractions from orange, tangerine and lemon peels. The possibility of using ethanol as a cosolvent at small percentages up to 20% was also studied. The extraction yield, total polyphenolic content, individual polyphenolic profile, antiradical activity and volatile organic compounds of the extracts were evaluated. The highest yields were obtained when 20% ethanol was used as a cosolvent in both liquid (at 20 MPa and 20 °C) and supercritical (at 30 MPa and 60 °C) CO2 extraction. In addition, the extracts obtained with liquid CO2 + 20% ethanol showed the highest content of naringin (35.26, 44.05 and 19.86 mg g‐1 in orange, tangerine and lemon peel extracts, respectively) and terpenes, in particular limonene. This type of extract also showed the highest antiradical activity (31.78–59.51 µmolTE g‐1) as measured by both ABTS·+ and DPPH·. These findings show that the extraction with a liquid CO2 and ethanol mixture could be a valid alternative to traditional solvent extraction using 80% less organic solvent and producing extracts with high antiradical capacity and rich in volatile organic compounds. Extraction by liquid CO2 produced extracts with high antioxidant activity and high content of naringin, flavonoids, limonene and total polyphenols.
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Transport engineering strategies use altered expression of transporter proteins to change metabolite distribution within an organism. The production of plant specialized metabolites in microbial cell factories encounters a set of challenges that could benefit from the implementation of transport engineering technology. The range of challenges includes premature pathway termination due to secretion of intermediates, feedback inhibition due to inefficient export of final products, low yields in bioconversion processes due to inefficient import of precursors and poor connectivity between subcellular compartments expressing different parts of complex biosynthetic pathways. We highlight the latest examples of transport engineering in microbial cell factories producing plant specialized metabolites, identify the current knowledge gap, and propose future research for advancing the field.
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Liver cirrhosis, alcoholic liver diseases, non-alcoholic fatty liver and steatohepatitis are the major risk factors for liver damage leading to hepatocellular carcinoma. Oxidative stress and insulin resistance are the main pathogenetic mechanisms leading the hepatic cell injury and damage in these patients. The present review is the first attempt which focuses on the biological activities of Bergenia ciliata to explore its benefits and possible applications in the treatment of liver ailments. Bergenia ciliata is an evergreen herb belonging to the family saxifragaceae and is regarded as a miracle herb due to its wide medicinal applications. The data published in India and other nations are methodically reviewed and summarized in this article. It covers the facts collected from scientific journals, theses and online bibliographical databases: PubMed, Scopus, Google Scholar and Web of Science from year 1995–2020. The phytochemical studies on B. ciliata have shown the presence of many phytochemicals belonging to phenols, flavonoids, fatty acid, glycosides, terpenoids, etc. Due to the presence of a multitude of these bioactives, the whole plant of B. ciliata has numerous medicinal applications such as diuretic, antipyretic, α-glucosidase, antiviral, antibacterial, anti-inflammatory and insecticidal activity. Therefore in the present study, we invite the attention of scientists and researchers to carry out further clinical and toxicological studies on this valuable plant in order to discover and develop novel hepatoprotective medicine with fewer side effects on human beings.
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Limonene is a monoterpene confined to the family of Rutaceae, showing several biological properties such as antioxidant, anti-inflammatory, anticancer, antinociceptive and gastroprotective characteristics. Recently, there is notable interest in investigating the pharmacological effects of limonene in various chronic diseases due to its mitigating effect on oxidative stress and inflammation and regulating apoptotic cell death. There are several available studies demonstrating the neuroprotective role of limonene in neurodegenerative diseases, including Alzheimer’s disease, multiple sclerosis, epilepsy, anxiety, and stroke. The high abundance of limonene in nature, its safety profile, and various mechanisms of action make this monoterpene a favorable molecule to be developed as a nutraceutical for preventive purposes and as an alternative agent or adjuvant to modern therapeutic drugs in curbing the onset and progression of neurodegenerative diseases. This manuscript presents a comprehensive review of the available scientific literature discussing the pharmacological activities of limonene or plant products containing limonene which attribute to the protective and therapeutic ability in neurodegenerative disorders. This review has been compiled based on the existing published articles confined to limonene or limonene-containing natural products investigated for their neurotherapeutic or neuroprotective potential. All the articles available in English or the abstract in English were extracted from different databases that offer an access to diverse journals. These databases are PubMed, Scopus, Google Scholar, and Science Direct. Collectively, this review emphasizes the neuroprotective potential of limonene against neurodegenerative and other neuroinflammatory diseases. The available data are indicative of the nutritional use of products containing limonene and the pharmacological actions and mechanisms of limonene and may direct future preclinical and clinical studies for the development of limonene as an alternative or complementary phytomedicine. The pharmacophore can also provide a blueprint for further drug discovery using numerous drug discovery tools.
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Essential oil distilled from the leaves and twigs of Kunzea ambigua is in high demand for its ‘soft, medicinal and soothing aroma’ and claimed muscle relaxant properties. This study investigated the changes in oil colour and chemical composition of kunzea essential oil over eight months of storage in a freezer (-20°C), a refrigerator (4°C) and at room temperature (20°C), with and without ambient light. The oil colour was measured by a colourimeter, and chemical compositions were analysed using Gas Chromatography (GC) Mass Spectrometry (MS) and Flame Ionization Detection (FID). Samples were analysed at one-, three-, five- and eight-month intervals. The colour difference (Δ E*) was highest in oils stored in the light at room temperature for eight months (5.60 ± 0.03%), whilst samples kept in the dark were more stable with ΔE* at room temperature of 1.97 ± 0.00%, refrigeration at 1.55 ± 0.02%, and freezing temperatures at 1.08 ± 0.17%. Stored kunzea essential oil became darker in colour, becoming less yellow and decreasing in greenness, with extended storage periods. The monoterpenes, sesquiterpenes and total volatile compounds in oil stored for eight months in the freezer, refrigerator, and room temperature without light were overall generally stable compared to fresh oil. Significant interactions between storage period and temperature/light treatments were recorded for bicyclogermacrene, α-humulene, α-campholenal and linalool, showing a decrease in all oils under all conditions during extended storage periods, though changes were minimal in frozen oil. However, the oils exposed to the light showed a significant decrease in these components, particularly for germacrene D, β-caryophyllene and α-humulene, likely due to thermal isomerization, relative to fresh oil. Overall, kunzea essential oil stored in a freezer or refrigerator was the most stable and consistent in colour and chemical profile whereas there is evidence that some components may be oxidized when exposed to light with negative consequences for oil colour and quality.
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The antibacterial activity of citrus essential oils (EOs) in the context of combating Limosilactobacillus fermentum, one of the most important bacterial contaminants in the bioethanol production industry, has never been explored previously. Industrial processes usually utilize sulfuric acid for cell treatment to decrease bacterial contamination. However, due to the hazardous nature of sulfuric acid, an alternative to it is highly desirable. Therefore, in the present study, the efficacy of Fremont IAC 543 mandarin EO against a strain of L. fermentum (ATCC® 9338™) was evaluated under proliferative/non‐proliferative conditions, in both pure culture and co‐culture with an industrial strain of Saccharomyces cerevisiae. The mandarin EO exhibited higher effectiveness against L. fermentum compared to that against S. cerevisiae under non‐proliferative conditions (added to water rather than to culture medium). At the concentration of 0.05%, the EO was as effective as the acid solution with pH 2.0 in reducing the count of L. fermentum almost 5 log CFU mL–1 cycles, while the concentration of 0.1% led to the complete loss of bacterial culturability. When L. fermentum was co‐cultured with S. cerevisiae, the efficacy of the EO against the bacterial strain was reduced. However, despite this reduced efficacy in co‐culture, mandarin EO may be considered effective in combating L. fermentum and could be applied in processes where this bacterium proves to be unfavorable and does not interact with S. cerevisiae.
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To ensure food security for the continuously growing worldwide population, it is necessary to promote the use of underutilized foods in food products. In this context, we evaluated the effect of a protein defatting process, which was performed using n-hexane, on the physicochemical characteristics, thermal stabilities, and aromatic profiles of proteins extracted from an edible insect, Protaetia brevitarsis. The defatting process decreased the color values (L*, a*, b*; P < 0.01) and apparent viscosities of the solutions of the extracted proteins and increased their pH values (P < 0.01), but did not affect their thermal stabilities. Additionally, defatting reduced the cohesiveness, gumminess, and chewiness (P < 0.01), but did not affect the hardness or springiness of the product. Furthermore, it lowered the levels of alcohols, aldehydes formed by lipid oxidation, and some hydrocarbons that have a negative physiological effect or impart an off-flavor to this food. Moreover, a simultaneous increase in the number of hydrocarbons with a pleasant flavor was observed. Collectively, the defatting process had a beneficial effect. It altered the properties of the insect proteins, and could potentially promote the use of edible insects as a protein source in the food industry.
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In maxillofacial surgery and implantology clinical practice, infection processes are common during the healing and graft osseointegration. Microorganisms’ resistance to various antimicrobials has increased steadily through the widespread use of topical antibiotics, and new substances with antimicrobial properties are urgently necessary to avoid the infection processes in bone grafts. In the present study, bovine bone grafts (BG) for dental application were functionalized with silver nanoparticles (NPs) synthesized by the bioreduction technique using extracted (EEO) and commercial orange essential oil (CEO). The majoritarian compound identified in EEO and CEO was d-limonene, with a concentration up to 95%. The UV–Vis spectroscopy of NPs demonstrated the maximum absorbance peak around 400 nm and the average diameter obtained by transmission electron microscopy was 50 and 80 nm, respectively for NPs-EEO and NPs-CEO. The physicochemical stability of the NPs was studied for 60 days, at refrigerated temperature (6 ± 2 °C), and NPs-EEO presented better results of zeta potential, polydispersity index, and particle size during storage. The antioxidant activity was determined by the inhibition of DPPH and ABTS free radicals and by the Fe³⁺ reducing power (FRAP assay). NPs showed better results of antioxidant activity by DPPH and FRAP methods when compared to individualized essential oils. NPs and functionalized bone grafts showed greater antagonistic actions than individualized essential oils against the seven studied microorganisms. Therefore, it is possible to affirm the biological importance of the biosynthesized NPs for use as an antimicrobial agent in dental biomaterials, being a promising alternative to avoid the infection processes in bone grafts.
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From nanocellulose through poly(limonene carbonate), numerous transparent and good light guiding biopolymers are suitable for the fabrication of optical devices. Being renewable and generally biocompatible, this establishes the concept of sustainable optics in which oil-derived polymers used to fabricate optical components and structures are replaced by biopolymers. Is such a replacement feasible on large scale? What are the main obstacles that remain to be addressed prior to industrial uptake of these polymers in the optical industry? The answers to these questions have numerous implications also for the development of the emerging bioeconomy.
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The number of aroma compounds obtained by biotechnological process has increased tremendously in recent years and, as a result, are now being extensively employed in order to make products more attractive for consumers. In the present review, we inten to assess the wide range of reactions are catalyzed by fungal strains in regards to biotransformation of limonene and pinene for the aroma compounds production, their production rates/maximum concentrations and their biological potential. We comprehensively summarized in this review available data (2000–2021) regarding fungal biotransformation of limonene and pinene as biotechnological processes. Over the past years, has been paid to the biotransformation processes due to mild and environmentally friendly conditions applied. This review has shown that reports on the application of the fungi as a promising source of biocatalysts, mainly for stereoselective reactions such as hydroxylation and epoxidation. Studies have demonstrated the existence of promising monoterpenes used as substrates, which could be important from an industrial standpoint since this increases their importance as starting materials for obtaining aromatic molecules new. Moreover, biological (e.g.,antioxidant, anticancer) activities attributed to some monoterpene biotransformation products are increasingly being reported, indicating that their applications may transcend food, cosmetic and pharmaceutical industry.
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Terpenes are a major class of natural aromatic compounds in grapes and wines to offer the characteristic flavor and aroma, serving as important quality traits of wine products. Saccharomyces cerevisiae represents an excellent cell factory platform for large-scale bio-based terpene production. This review describes the biosynthetic pathways of terpenes in different organisms. The metabolic engineering of S. cerevisiae for promoting terpene biosynthesis and the alternative microbial engineering platforms including filamentous fungi and Escherichia coli are also elaborated. Additionally, the potential applications of the terpene products from engineered microorganisms in food and beverage industries are also discussed. This review provides comprehensive information for an innovative supply way of terpene via microbial cell factory, which could facilitate the development and application of this technique at the industrial scale.
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The biotechnological production of aroma compounds may be carried out using enzymatic methodologies or microbial approaches and different substrates. In this context, the use of low-cost monoterpenes such as limonene and pinene isomers and fungal biocatalysts can be considered a promising approach for the production of oxygenated derivatives with important aroma characteristics. Considering the diversity of fungi strains employed on the biotransformation processes, this review presents the most important strategies applied to the production of monoterpene-derived aromas using limonene and pinene isomers as substrates, summarizing the main structural modifications achieved as well as strategies for the screening of novel strains, optimization of process parameters and the biological potential of these aromas.
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Forest bathing has beneficial effects on human health via showering of forest aerosols as well as physical relaxation. Terpenes that consist of multiple isoprene units are the largest class of organic compounds produced by various plants, and one of the major components of forest aerosols. Traditionally, terpene-containing plant oil has been used to treat various diseases without knowing the exact functions or the mechanisms of action of the individual bioactive compounds. This review categorizes various terpenes easily obtained from forests according to their anti-inflammatory, anti-tumorigenic, or neuroprotective activities. Moreover, potential action mechanisms of the individual terpenes and their effects on such processes, which are described in various in vivo and in vitro systems, are discussed. In conclusion, the studies that show the biological effectiveness of terpenes support the benefits of forest bathing and propose a potential use of terpenes as chemotherapeutic agents for treating various human diseases.
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Aims: We have investigated the antihyperalgesic effects of limonene in mice that received intrathecal injection of gp120. Main methods: Male Swiss mice received gp120, IL-1β or TNF-α intrathecally or sterile saline as a control. A mechanicalsensitivity test was performed at 2 and 3h after the injection. Spinal cord and blood samples were isolated for protein quantification. Key findings: Intrathecal administration of gp120 increased mechanical sensitivity measured with an electronic Von Frey apparatus, at 2 and 3h after the injections. Limonene administered orally prior to gp120 administration significantly decreased this mechanical sensitivity at 3h after the gp120 injection. In addition, intrathecal injection of gp120 increased IL-1β and IL-10 in serum, and limonene prevented the ability of gp120 to increase these cytokines. Limonene also inhibited TNF-α and IL-1β-induced mechanical hyperalgesia. Western blot assay demonstrated limonene was capable of increasing SOD expression in the cytoplasm of cells from spinal cord at 4h after intrathecal IL-1β injection. Significance: These results demonstrate that gp120 causes mechanical hyperalgesia and a peripheral increase in IL-1β and IL-10, and that prior administration of limonene inhibits these changes. Also limonene modulates the activation of SOD expression in the spinal cord after spinal IL-1β application. The ability of limonene to inhibit the mechanical hyperalgesia induced by gp120, TNF-α and IL-1β emphasizes the anti-inflammatory action of limonene, specifically its ability to inhibit cytokine production and its consequences.
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Inhalation of indoor air pollutants may cause airway irritation and inflammation and is suspected to worsen allergic reactions. Inflammation may be due to mucosal damage, upper (sensory) and lower (pulmonary) airway irritation due to activation of the trigeminal and vagal nerves, respectively, and to neurogenic inflammation. The terpene, d-limonene, is used as a fragrance in numerous consumer products. When limonene reacts with the pulmonary irritant ozone, a complex mixture of gas and particle phase products is formed, which causes sensory irritation. This study investigated whether limonene, ozone or the reaction mixture can exacerbate allergic lung inflammation and whether airway irritation is enhanced in allergic BALB/cJ mice. Naïve and allergic (ovalbumin sensitized) mice were exposed via inhalation for three consecutive days to clean air, ozone, limonene or an ozone-limonene reaction mixture. Sensory and pulmonary irritation was investigated in addition to ovalbumin-specific antibodies, inflammatory cells, total protein and surfactant protein D in bronchoalveolar lavage fluid and hemeoxygenase-1 and cytokines in lung tissue. Overall, airway allergy was not exacerbated by any of the exposures. In contrast, it was found that limonene and the ozone-limonene reaction mixture reduced allergic inflammation possibly due to antioxidant properties. Ozone induced sensory irritation in both naïve and allergic mice. However, allergic but not naïve mice were protected from pulmonary irritation induced by ozone. This study showed that irritation responses might be modulated by airway allergy. However, aggravation of allergic symptoms was observed by neither exposure to ozone nor exposure to ozone-initiated limonene reaction products. In contrast, anti-inflammatory properties of the tested limonene-containing pollutants might attenuate airway allergy.
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We studied the R-limonene (LMN) metabolism and elimination kinetics in a human in vivo study. Four volunteers were orally exposed to a single LMN dose of 100–130 µg kg−1 bw. In each case, one pre-exposure and subsequently all 24 h post-exposure urine samples were collected. From two subjects, blood samples were drawn up to 5 h after exposure. The parent compound was analysed in blood using headspace GC–MS. The metabolites cis- and trans-carveol (cCAR), perillyl alcohol (POH), perillic acid (PA), limonene-1,2-diol (LMN-1,2-OH), and limonene-8,9-diol (LMN-8,9-OH) were quantified in both blood and urine using GC-PCI-MS/MS. Moreover, GC-PCI-MS full-scan experiments were applied for identification of unknown metabolites in urine. In both matrices, metabolites reached maximum concentrations 1–2 h post-exposure followed by rapid elimination with half-lives of 0.7–2.5 h. In relation to the other metabolites, LMN-1,2-OH was eliminated slowest. Nonetheless, overall renal metabolite elimination was completed within the 24-h observation period. The metabolite amounts excreted via urine corresponded to 0.2 % (cCAR), 0.2 % (tCAR), <0.1 % (POH), 2.0 % (PA), 4.3 % (LMN-1,2-OH), and 32 % (LMN-8,9-OH) of the orally administered dose. GC-PCI-MS full-scan analyses revealed dihydroperillic acid (DHPA) as an additional LMN metabolite. DHPA was estimated to account for 5 % of the orally administered dose. The study revealed that human LMN metabolism proceeds fast and is characterised by oxidation mainly of the exo-cyclic double bond but also of the endo-cyclic double bond and of the methyl side chain. The study results may support the prediction of the metabolism of other terpenes or comparable chemical structures.
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Oxidative stress, as mediated by ROS, is a significant factor in initiating the development of age-associated cataracts; D-limonene is a common natural terpene with powerful antioxidative properties which occurs naturally in a wide variety of living organisms. It has been shown to have antioxidant effect; we found that D-limonene can effectively prevent the oxidative damage caused by H 2 O 2 and propose that the main mechanism underlying the inhibitory effects of D-limonene is the inhibition of HLECs apoptosis. In the present study, we used confocal-fluorescence microscopy, flow cytometry analysis, Hoechst staining, H 2 DCFDA staining, transmission electron microscopy, and immunoblot analysis; the results revealed that slightly higher concentrations of D-limonene (125–1800 μ M) reduced the H 2 O 2 -induced ROS generation and inhibited the H 2 O 2 -induced caspase-3 and caspase-9 activation and decreased the Bcl-2/Bax ratio. Furthermore, it inhibited H 2 O 2 -induced p38 MAPK phosphorylation. Thus, we conclude that D-limonene could effectively protect HLECs from H 2 O 2 -induced oxidative stress and that its antioxidative effect is significant, thereby increasing the cell survival rate.
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Aim To study the effects of d- and l-limonene on pregnant rat myometrial contractility in vitro, and investigate how these effects are modified by other agents. D- and l-limonene (10−13-10−8 M) caused myometrial contraction in a dose-dependent manner. Methods Contractions of uterine rings from 22-day-pregnant rats were measured in an organ bath in the presence of d- or l-limonene (10−13-10−8 M) and nifedipine (10−8 M), tetraethyl-ammonium (10−3 M), theophylline (10−5 M), or paxilline (10−5 M). Uterine cyclic adenosine monophosphate (cAMP) level was detected by enzyme immunoassay. Oxidative damage was induced by methylglyoxal (3 × 10−2 M) and the alteration was measured via noradrenaline (1 × 10−9 to 3 × 10−5 M) -induced contractions. Results Pre-treatment with nifedipine (10−8 M), tetraethylammonium (10−3 M), and theophylline (10−5 M) attenuated the contracting effect of d- and l-limonene, while in the presence of paxilline (10−5 M) d- and l-limonene were ineffective. The two enantiomers decreased the myometrial cAMP level, but after paxilline pretreatment the cAMP level was not altered compared with the control value. Additionally, l-limonene (10−6 M) diminished consequences of oxidative damage caused by methylglyoxal (3 × 10−2 M) on contractility, whereas d-limonene was ineffective. Conclusion Our findings suggest that l-limonene has an antioxidant effect and that both d-and l-limonene cause myometrial contraction through activation of the A2A receptor and opening of the voltage-gated Ca²⁺ channel. It is possible that limonene-containing products increase the pregnant uterus contractility and their use should be avoided during pregnancy.
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Essential oils are complex mixtures containing compounds of several different functional- group classes. Depending on the structure, we can distinguish monoterpenes, phenylpropanes, and other components. Here in this study two monoterpene compounds of essential oils, i.e. β-pinene and limonene were examined for their antiviral activity against herpes simplex virus type 1 (HSV-1) in vitro. All antiviral assays were performed using RC-37 cells. Cytotoxicity was determined in a neutral red assay, antiviral assays were performed with HSV-1 strain KOS. The mode of antiviral action was evaluated at different periods during the viral replication cycle. Acyclovir was used as positive antiviral control. Beta-pinenene and limonenen reduced viral infectivity by 100 %. The mode of antiviral action has been determined, only moderate antiviral effects were revealed by monoterpenes when these drugs were added to host cells prior infection or after entry of HSV into cells. However, both monoterpenes exhibited high anti-HSV-1 activity by direct interaction with free virus particles. Both tested drugs interacted with HSV-1 in a dose-dependent manner thereby inactivating viral infection. These results suggest that monoterpenes in essential oils exhibit antiherpetic activity in the early phase of viral multiplication and might be used as potential antiviral agents.
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Increasing demand of cosmetics all over the world from teen to adult has increased awareness related to safety issue. The objective of this paper is to indicate the ingredients that possess health effect that can be found in cosmetics and personal care products. The ingredient was segmented to three parts which are preservatives, fragrances and heavy metal impurities. The related paper was reviewed in terms of the chemicals that commonly identified in the cosmetic and personal care product. This paper also highlighted the health risk possesses by such ingredients in the products. From the papers reviews, many chemicals remained arguable in term of safety and its presence in the products. The chemicals are either added for it intentional purposes or appears unintentionally due to the nature of chemical itself or due to the manufacturing processes. It is suggested that consumers aware over the ingredients used in their cosmetic and personal care products and the side effects it possesses.
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Abstract Osteoarthritis is a progressive joint disease and a major cause of disability for which no curative therapies are yet available. To identify compounds with potential anti-osteoarthritic properties, in this study, we screened one sesquiterpene, E-caryophyllene, and two monoterpene, myrcene and limonene, hydrocarbon compounds for anti-inflammatory, anti-catabolic and pro-anabolic activities in human chondrocytes. At non-cytotoxic concentrations, myrcene and limonene inhibited IL-1β-induced nitric oxide production (IC50=37.3 μg/ml and 85.3 µg/ml, respectively), but E-caryophyllene was inactive. Myrcene, and limonene to a lesser extent, also decreased IL-1β-induced NF-κB, JNK and p38 activation and the expression of inflammatory (iNOS) and catabolic (MMP-1 and MMP-13) genes, while increasing the expression of anti-catabolic genes (TIMP-1 and −3 by myrcene and TIMP-1 by limonene). Limonene increased ERK1/2 activation by 30%, while myrcene decreased it by 26%, relative to IL-1β-treated cells. None of the compounds tested was able to increase the expression of cartilage matrix-specific genes (collagen II and aggrecan), but both compounds prevented the increased expression of the non-cartilage specific, collagen I, induced by IL-1β. These data show that myrcene has significant anti-inflammatory and anti-catabolic effects in human chondrocytes and, thus, its ability to halt or, at least, slow down cartilage destruction and osteoarthritis progression warrants further investigation.
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Essential oils are complex mixtures isolated from aromatic plants which may possess antioxidant and anti-inflammatory activities of interest in thye food and cosmetic industries as well as in the human health field. In this work, a review was done on the most recent publications concerning their antioxidant and anti-inflammatory activities. At the same time a survey of the methods generally used for the evaluation of antioxidant activity and some of the mechanisms involved in the anti-inflammatory activities of essential oils are also reported.
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Objectives: Previous studies have shown that essential oil containing (R)-(+)-limonene and α-phellandrene, extracted from fruits of Schinus terebinthifolius Raddi, exhibit anti-inflammatory activity. This work aimed to verify the antihyperalgesic and antidepressive actions of (R)-(+)-limonene, α-phellandrene, and essential oil from S. terebinthifolius fruits in spared nerve injury (SNI) model of neuropathic pain in rats. Methods: In the present work, essential oil from fruits of S. terebinthifolius, as well as the pure (R)-(+)-limonene and α-phellandrene compounds, were assayed for their effects on SNI-induced mechanical and cold hyperalgesia, and depressive-like behavior (immobility in forced swim test) in rats. The locomotor activity was evaluated in open-field test. Results: Oral administration for up to 15 days of essential oil of S. terebinthifolius (100 mg/kg), (R)-(+)-limonene (10 mg/kg), α-phellandrene (10 mg/kg), and also subcutaneous 10 mg/kg dose of ketamine (positive control) significantly inhibited SNI-induced mechanical hyperalgesia and increased immobility in the forced swim test. On the 15th day of oral treatment, α-phellandrene, but neither the essential oil from S. terebinthifolius nor (R)-(+)-limonene, prevented the SNI-induced increase in sensitivity to a cold stimulus. The oral treatment with essential oil (100 mg/kg) or with compounds (10 mg/kg) did not interfere on locomotor activity. Discussion: Together, the results of the present work show that essential oil of S. terebinthifolius and compounds present in this oil, including (R)-(+)-limonene and α-phellandrene, exhibit antihyperalgesic effects against mechanical hyperalgesia, and are antidepressive, while only α-phellandrene inhibited cold hyperalgesia in SNI rats.
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d-limonene is a naturally occurring monoterpene and has been found to posses numerous therapeutic properties. In this study, we used d-limonene as a protective agent against the nephrotoxic effects of anticancer drug doxorubicin (Dox). Rats were given d-limonene at doses of 5% and 10% mixed with diet for 20 consecutive days. Dox was give at the dose of 20 mg/kg body weight intraperitoneally. The protective effects of d-limonene on Dox-induced oxidative stress and inflammation were investigated by assaying oxidative stress biomarkers, lipid peroxidation, serum toxicity markers, proinflammatory cytokines, and expression of nuclear factor kappa B (NFκB), cyclo-oxygenase-2 (COX-2), and inducible nitric oxide synthase (iNOS) and Nitrite levels. Administration of Dox (20 mg/kg body weight) in rats enhanced renal lipid peroxidation; depleted glutathione content and anti-oxidant enzymes; elevated levels of kidney toxicity markers viz. kidney injury molecule-1 (KIM-1), blood urea nitrogen (BUN), and creatinine; enhanced expression of NFκB, COX-2, and iNOS and nitric oxide. Treatment with d-limonene prevented oxidative stress by restoring the levels of antioxidant enzymes, further both doses of 5% and 10% showed significant decrease in inflammatory response. Both the doses of d-limonene significantly decreased the levels of kidney toxicity markers KIM-1, BUN, and creatinine. d-limonene also effectively decreased the Dox induced overexpression of NF-κB, COX-2, and iNOS and nitric oxide. Data from the present study indicate the protective role of d-limonene against Dox-induced renal damage.
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Abstract Previous studies have described the gastroprotective effects of essential oils that are derived from Citrus aurantium (OEC) and its main compound d-limonene (LIM) in a model of chemically induced ulcers in rats. However, these studies do not address the compound's healing effects on the gastric mucosa. Thus, the aim of this work was to evaluate the healing activity of OEC and LIM in acetic acid-induced gastric ulcers in rats, a model that reproduces human chronic ulcers. The obtained results demonstrated that lower effective doses of OEC (250 mg/kg) and LIM (245 mg/kg) induced gastric mucosal healing with a cure rate of 44% and 56%, respectively, compared with the control group (P<.05). During the 14 days of OEC or LIM treatment, none of the groups demonstrated toxicity in terms of body and organ weight or serum biochemical parameters. Both OEC and LIM treatment promoted an increase in epithelial healing, as confirmed by immunohistochemistry, which was greater in the animals that were treated with the positive control. In addition, both treatments increased cellular proliferation as measured by proliferating cell nuclear antigen and cyclooxygenase 2 expression in the gastric mucosa, vascular endothelial growth factor-mediated blood vessel formation in the margin of the ulcer, and production of gastric mucus, which fortifies the gastric protective barrier. We concluded that OEC and LIM, two common flavoring agents, promote gastric mucosal healing without any apparent toxic effect, resulting in better gastric epithelial organization in the treated rats.
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The genus Citrus (Rutaceae) includes several species of plants that produce some of the most cultivated fruits in the world, providing an appreciable content of essential oil. In folk medicine, they are used as a cholagogue, antipyretic, anti-inflammatory, sedative, and antitoxic effects. Lemon essential oil has been used since ancient times for its antiseptic, carminative, diuretic, and eupeptic effects. In this study, we investigated the anti-inflammatory activity of Citrus latifolia Tanaka essential oil (CLEO) and its main constituent LIM. In the cell viability assay, CLEO and LIM (3, 10, 30, and 90 μ g/mL) had low cytotoxicity. In zymosan-induced peritonitis, LIM (500 mg/kg) decreased the infiltration of peritoneal exudate leukocytes and decreased the number of polymorphonuclear leukocytes. In vitro chemotaxis revealed that CLEO and LIM (1, 3, and 10 µg/mL) promoted a significant reduction of neutrophil migration toward fMLP and LTB4. LIM (500 mg/kg) also reduced TNF- α levels but did not alter IL-10 levels in the peritoneal exudate. In conclusion, this study showed that LIM isolated from CLEO had potential anti-inflammatory effects, likely by inhibiting proinflammatory mediators present in inflammatory exudate and leukocyte chemotaxis.
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Disruption of lipid and carbohydrate homeostasis is an important factor in the development of prevalent metabolic diseases such as diabetes, obesity, and atherosclerosis. Therefore, small molecules that could reduce insulin dependence and regulate dyslipidemia could have a dramatic effect on public health. The grapefruit flavonoid naringenin has been shown to normalize lipids in diabetes and hypercholesterolemia, as well as inhibit the production of HCV. Here, we demonstrate that naringenin regulates the activity of nuclear receptors PPARα, PPARγ, and LXRα. We show it activates the ligand-binding domain of both PPARα and PPARγ, while inhibiting LXRα in GAL4-fusion reporters. Using TR-FRET, we show that naringenin is a partial agonist of LXRα, inhibiting its association with Trap220 co-activator in the presence of TO901317. In addition, naringenin induces the expression of PPARα co-activator, PGC1α. The flavonoid activates PPAR response element (PPRE) while suppressing LXRα response element (LXRE) in human hepatocytes, translating into the induction of PPAR-regulated fatty acid oxidation genes such as CYP4A11, ACOX, UCP1 and ApoAI, and inhibition of LXRα-regulated lipogenesis genes, such as FAS, ABCA1, ABCG1, and HMGR. This effect results in the induction of a fasted-like state in primary rat hepatocytes in which fatty acid oxidation increases, while cholesterol and bile acid production decreases. Our findings explain the myriad effects of naringenin and support its continued clinical development. Of note, this is the first description of a non-toxic, naturally occurring LXRα inhibitor.
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