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A simple aqueous host:guest sensing array can selectively discriminate between different types of citrus varietal from peel extract samples. It can also distinguish between identical citrus samples at varying stages of ripening. The discrimination effects stem from detection of changes in the terpenoid composition of the peel extracts by the host:guest array, despite the overwhelming excess of a single component, limonene, in each sample. The hosts are insensitive to limonene but bind other monoterpenes strongly, even though they are similar in structure to the major limonene component. This work demonstrates the capability of host:guest arrays in sensing target molecules in environments with the competing agents present at high abundances in the sample matrix.

Bergamot (Citrus bergamia Risso) is not consumed as fresh fruit as other members of Citrus. Bergamot essential oil has a unique aroma. Bergamot essential oil is a very valuable product used in perfumery, cosmetics, aromatherapy and food industry due to its beautiful scent and functional properties. As with other Citrus species, the composition of bergamot essential oil can vary according to harvest time, climate and extraction technology. Bergamot essential oil could be obtained by cold press extraction or distillation method. Within the scope of the study, the effect of four different hydrodistillation (HD) times (5, 10, 60 and 120 min) on the composition of bergamot essential oil obtained from Turkish fruits was investigated. In the first 60 min, 96.11% of the total essential oil was obtained. Research findings have shown that the distillation time is quite effective in the composition of bergamot essential oil. Limonene, linalool and linalyl acetate, which are the main components of bergamot essential oil, varied in the range, 42.36%–53.25%, 5.59%–12.18% and 20.84%–26.73%, respectively, with respect to distillation time. In cold press method, bergamot essential oil has lower linalool/linalyl acetate ratio (0.15) compared to HD method and a higher quality essence was obtained. [ABSTRACT FROM AUTHOR]

Copyright of Shipin Kexue/ Food Science is the property of Food Science Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Copyright of Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas is the property of Universidad de Santiago de Chile and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Background Objectives Patients and Methods Results Conclusions Propolis was added to the European baseline series (EBS) in 2019.To investigate the frequency and relevance of positive patch tests to propolis in the EBS and to study co‐reactivities.Retrospective study in patients patch tested between June 2019 and November 2023 in a university hospital in Amsterdam, The Netherlands.Of 3134 consecutive patients, 299 (9.5%) had a positive reaction to propolis 10% pet. Only nine reactions (3%) were judged to be clinically relevant. There were significant co‐reactivities to Myroxylon pereirae resin (balsam of Peru), colophonium, fragrance mixes 1 and 2, and to limonene and linalool hydroperoxides. A steep increase in rates of positive reactions to propolis was observed from 2020 to 2023. This was highly likely the result of the replacement of Chinese propolis with Brazilian propolis by the manufacturer.Positive patch tests for propolis are very frequent in Amsterdam, but only a few of these reactions are relevant. Most are probably (pseudo‐)cross‐reactions in patients with fragrance allergies. Propolis in the EBS has very limited value for dermatologists and patients in The Netherlands. Changes in patch test materials should be provided to all users to avoid misinterpretation of patch test results. [ABSTRACT FROM AUTHOR]

The essential oils derived from various coniferous species, including Cupressus torulosa, have been historically valued for their aromatic properties. In the present study, essential oil from C. torulosa needles (CTEO) was analyzed using Gas Chromatography (GC), Gas Chromatography-Mass Spectrometry (GC-MS), and Gas Chromatography-Olfactometry (GC-O) with Aroma Extract Dilution Analysis (AEDA). A total of 36 compounds were identified, with δ-3-carene (0.1824 ± 0.0084 mg/g), sabinene (0.1125 ± 0.036 mg/g), and terpinen-4-ol (0.0891 ± 0.0034 mg/g) as major constituents. Of these, 24 were odor-active. The aroma profile of CTEO featured top notes of green, fresh leafy, cool, fruity, and citrus scents, middle notes of dry woody tones, and base notes of spicy and dry characteristics. Predictive models including FD factor, Odor Activity Values, and Relative Flavor Activity highlighted α-pinene, α-terpinene, linalool, bornyl acetate, β-pinene, camphor, limonene, and terpinen-4-ol as key aroma contributors. This study provides valuable insights into the aromatic profile of CTEO, with potential applications in the aroma industry. [ABSTRACT FROM AUTHOR]

[(Bn-tpen)FeII(MeCN)](ClO4)2, containing the pentadentate Bn-tpen–N-benzyl-N,N′,N′-tris(2-pyridylmethyl)-1,2-diaminoethane ligand, was studied in the oxygenation of cyclohexene and limonene using low-pressure dioxygen (0.2 atm air or 1 atm pure O2) in acetonitrile. 2-Cyclohexen-1-one and 2-cyclohexen-1-ol are the main products of cyclohexene oxidations, with cyclohexene oxide as a minor product. Limonene is oxidized to limonene oxide, carvone, and carveol. Other oxidation products such as perillaldehyde and perillyl alcohol are found in trace amounts. This catalyst is slightly less active than the previously reported [(N4Py)FeII(MeCN)](ClO4)2 (N4Py–N,N-bis(2-pyridylmethyl)-N-(bis-2-pyridylmethyl)amine). Based on cyclic voltammetry experiments, it is postulated that [(Bn-tpen)FeIV=O]2+ is the active species. The induction period of approx. 3 h during cyclohexene oxygenation is probably caused by deactivation of the reactive Fe(IV)=O species by the parent Fe(II) complex. Equimolar mixtures of Fe(II) salt and the ligand (in situ-formed catalyst) gave catalytic performance similar to that of the synthesized catalyst. [ABSTRACT FROM AUTHOR]

Limonene, a dietary monocyclic monoterpene commonly found in citrus fruits and various aromatic plants, has garnered increasing interest as a gastrointestinal protectant. This study aimed to assess the effects of limonene on intestinal epithelial barrier function and investigate the involvement of cannabinoid receptor type‐1 (CB1R) in vitro. Additionally, the study focused on examining the metabolomic changes induced by limonene in the intestinal epithelial cells (Caco‐2). Initial analysis of transepithelial electrical resistance (TEER) revealed that both l‐limonene and d‐limonene, isomers of limonene, led to a dose‐ and time‐dependent increase in TEER in normal cells and those inflamed by pro‐inflammatory cytokines mixture (CytoMix). Furthermore, both types of limonene reduced CytoMix‐induced paracellular permeability, as demonstrated by a decrease in Lucifer yellow flux. Moreover, d‐limonene and l‐limonene treatment increased the expression of tight junction molecules (TJs) such as occludin, claudin‐1, and ZO‐1, at both the transcriptional and translational levels. d‐Limonene upregulates E‐cadherin, a molecule involved in adherens junctions (AJs). Mechanistic investigations demonstrated that d‐limonene and l‐limonene treatment significantly inhibited CB1R at the protein, while the mRNA level remained unchanged. Notably, the inhibitory effect of d‐limonene on CB1R was remarkably similar to that of pharmacological CB1R antagonists, such as rimonabant and ORG27569. d‐limonene also alters Caco‐2 cell metabolites. A substantial reduction in β‐glucose and 2‐succinamate was detected, suggesting limonene may impact intestinal epithelial cells' glucose uptake and glutamate metabolism. These findings suggest that d‐limonene's CB1R antagonistic property could effectively aid in the recovery of intestinal barrier damage, marking it a promising gastrointestinal protectant. [ABSTRACT FROM AUTHOR]

Volatile organic compounds (VOCs) in food are key factors constituting their unique flavor, while the characteristics of VOCs in air-dried yak meat (AYM) from various regions of the Tibetan Plateau and their inter-regional differences remain unclear. Therefore, this study conducted a comprehensive analysis of VOCs in the five-spice (FS), spicy and numbing (SN), and aromatic and spicy (AS) versions of AYM from four regions of the Tibetan Plateau (Gansu, Qinghai, Sichuan, and Tibet) using gas chromatography–ion mobility spectrometry (GC–IMS) A total of 58 VOCs were identified, with alcohols accounting for 28.40%, ketones 22.89%, aldehydes 18.85%, and terpenes 17.61%. Topographic plots, fingerprint profiles, and multivariate analysis not only distinguished AYM of the same flavor from different regions but also discriminated those of different flavors within the same region. Furthermore, 17 key VOCs were selected as the primary aroma characteristics of the 12 types of AYM, including linalool, 3-methylbutanal, acetone, and limonene. Meanwhile, the differential VOCs for each flavor were determined, with linalyl acetate being unique to the FS, (E)-ocimene and ethyl propanoate being specific to the SN, and 2-methyl-3-(methylthio)furan-D and Hexanal-D being characteristic of the AS flavor. Based on the above results, the flavor of AYM can be improved to suit the taste of most people and increase its consumption. [ABSTRACT FROM AUTHOR]

Pistacia palaestina Boiss. is a common tree in the Mediterranean maquis. The leaves of this plant accumulate defensive monoterpenes, whose levels greatly increase in galls induced by the aphid Baizongia pistaciae. We previously found a significant chemopolymorphism in monoterpene content among individual trees, but the chirality of these monoterpenes was unknown. Although most plant species specifically accumulate one enantiomeric form of a given compound, P. palaestina individuals display chemopolymorphism in the chirality of the key monoterpenes accumulated. We report here a marked enantiomeric variation for the limonene, α‐ and β‐pinene, camphene, sabinene, δ‐3‐carene, and terpene‐4‐ol content in leaves and galls of nine different naturally growing P. palaestina trees. Interestingly, insect‐induced gall monoterpene composition is an augmentation of the specific enantiopolymorphism originally displayed by each individual tree. [ABSTRACT FROM AUTHOR]

Monensin and essential oils have antimicrobial properties that may impact silage fermentation. The present study was divided into two trials to evaluate the effects of monensin (MON) and essential limonene oils (ELO) as additives in the ensiling of total mixed ration (TMR). In the first assay, TMR was tested with sheep in growth (65% dry matter—DM) using the following treatments: control (no additive), MON35 (35 mg of monensina per kg of DM), MON45 (45 mg of monensina per kg of DM), ELO300 (300 mg of essential limonene oil per kg of DM), and ELO600 (600 mg of essential limonene oil per kg of DM). In the second assay, the same treatments were used in TMR for lactating cows under two moisture conditions (30% and 40% DM). The parameters assessed included fermentative losses, short-chain fatty acid profiles, aerobic stability (hours needed for silage to reach 2 °C above ambient), chemical composition, and in vitro DM digestibility of the silages. Treatment averages were compared using the Scott–Knott test at 5% significance. In the first assay, the treatments with ELO had the lowest (p < 0.05) pH values and the highest (p < 0.05) lactic acid concentrations, with treatment ELO600 leading to the highest (p < 0.05) aerobic stability (297.88 h). Only the starch contents of the ELO treatments were lower (p < 0.05) than the others. In the second assay, the silages with the highest moisture contents and ELO600 exhibited the lowest (p < 0.05) values of DM recovery, lactic acid, and pH. The highest (p < 0.05) lactic acid:acetic acid ratios were observed in the silages with the most moisture added with MON35 and MON45. The use of MON and ELO increased aerobic stability, with the highest (p < 0.05) values observed for ELO600 and MON35. The treatments with MON and ELO resulted in silages with the lowest (p < 0.05) fiber contents and highest ether extract and starch contents when compared with control. Thus, MON and essential oils improve fermentative quality but ELO should be used in lower doses in humid silages to avoid negative fermentation impacts. [ABSTRACT FROM AUTHOR]

Mints are aromatic plants of Lamiaceae, globally known for the phytochemical-rich essential oils. Most of the cultivated mints are menthol-rich, whereas spearmint being the only dominant carvone-rich species. In this study, another carvone-rich mint Mentha rotundifolia (L.) Huds., a native of temperate region was assessed for its acclimation in sub-tropical environment to see any possible changes in specialized metabolite accumulation. Plants grown under open environment was compared with glasshouse grown plants where, temperature, humidity and photoperiods were uniformly maintained. Thickened leaves with increased cuticular wax load (2.82 folds) and anthocyanin accumulation (202.97 µg/g) in the widened stems were observed in plants grown in open environment, while higher chlorophyll contents were exhibited by the glasshouse-grown plants. Enhanced antioxidant capacity in open environment, correlated with elevated concentration (86.4% increase for caffeic acid) of wall-bound phenolics was observed. Increased proline, hydrogen peroxide and malondialdehyde contents in open environment indicated the plant's ability to cope up with abiotic stress. Higher amounts of terpenes like (-)-carvone (2.68 folds) and D-limonene (1.35 folds) were found in both internal volatile pool and essential oil of glasshouse-grown plants. Histochemical study of glandular trichomes also supported this finding. In conclusion, glasshouse-grown plants showed relatively better growth and higher terpene contents, nevertheless the plant survived well in warmer environment, with increased antioxidant capacities and phenolic contents. Future study includes mass propagation of this species in different geographical locations with distinct climatic variations to determine the suitable sub-tropical locations for cultivation as a potential alternative to spearmint for commercial-scale (-)-carvone production. [ABSTRACT FROM AUTHOR]

Plantar fasciitis is the most common cause of heel pain in adults with an overall prevalence of 0.85% in the adult population of the US, affecting over 2 million adults annually. Most current treatment modalities are not supported by sufficient evidence to recommend one particular strategy over another. Topical application of analgesics for soft tissue pain is well established, however the plantar fascia presents challenges in this regard due to thick skin, fibrotic tissue, and an often thickened fat pad. Sixty-two patients with plantar fasciitis were randomized to a placebo controlled trial testing the efficacy of a topical solution of plant terpenes containing camphor, menthol, eugenol, eucalyptol, and vanillin. Skin permeation of the mixture was enhanced with 15% dimethylsulfoxide (DMSO), 1% limonene, and rosemary oil. One ml of solution was applied topically twice daily, and pain scores evaluated on Day 0, Day 1, Day 3, and Day 10. Using the validated foot function index 78.1% of patients reported an 85% or greater decrease in their total pain score by day 10 while placebo treatment was without effect (One Way ANOVA, P < 0.01). This study adapts the treatment modality of topical analgesia for soft tissue pain to a problematic area of the body and shows therapeutic promise. ClinicalTrials.gov Identifier: NCT05467631 [ABSTRACT FROM AUTHOR]

This study was conducted to determine the sea fennel essential oil (SFEO) yield, composition, and antioxidant activity of leaves, stem, inflorescences, and umbels from seeds of wild sea fennel (SF) (Crithmum maritimum L.) from the Montenegro coast. The chemical composition of isolated essential oil was determined by GC/MS and GC/FID analyses. The antioxidant activity was determined using the DPPH assay. The maximum SFEO yield was found in umbels with seeds (4.77 mL/100 g p.m.). The leaves contained less EO (0.52 mL/100 g p.m.) than immature inflorescence (0.83 mL/100 g p.m.) The minimum EO content was found in the stem (0.08%). Twenty components were isolated from SFEO leaves, twenty-four from inflorescence, thirty-four components from the stem, and twenty-one components from umbels with seeds. Limonene (62.4–72.0%), γ-terpinene (9.5–14.0%), α-pinene (1.4–5.8%), and sabinene (1–6.5%) were found to be the main components of the SFEO from monoterpene hydrocarbons as dominant grouped components (86% to 98.1%). SF plant parts showed differences in chemical profiles, especially in specific and low-represented ingredients. (E)-anethole (4.4%), fenchone (0.5%), and trans-carveol (0.2%) were present only in umbel with seeds, while the β-longipipene (0.5%), (E)-caryophyllene (0.5%), and (2E)-decenal (0.2%) were found only in the stems. The degree of DPPH radical neutralization increased with incubation time. The SFEO isolated from the stems showed stronger antioxidant activity during the incubation times of 20 and 40 min (EC50 value of 5.30 mg/mL and 5.04 mg/mL, respectively) in comparison to the SFEO isolated from the other plant parts. The lowest antioxidant activity was obtained with the SFEO leaves (155.25 mg/mL and 58.30 mg/mL, respectively). This study indicates that SFEO possesses significant antioxidant activities and is animportant component in the food and pharmaceutical industries. It is important to preserve the existing gene pool and biodiversity with rational use SF for the extraction of high-quality essential oils. [ABSTRACT FROM AUTHOR]

Copyright of Science & Technology of Food Industry is the property of Science & Technology of Food Industry Editorial Office and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

The sterile insect technique (SIT) is used for the management of tephritid fruit fly pests. The South American fruit fly, Anastrepha fraterculus (Wiedemann) (Diptera: Tephritidae), is one potential pest to be targeted by means of SIT. The success of SIT depends, to a large extent, on the sexual performance of sterile males. Various approaches have been evaluated with the aim of improving their sexual performance. These include the exposure to plant‐derived compounds and/or the provision of protein sources in the adults' diet capable of stimulating male mating success. The present study aimed to determine whether exposure to volatiles of Citrus limon (L.) Burm. F. (Rutaceae) essential oil and limonene confers a mating advantage to A. fraterculus laboratory males fed two distinct dietary regimes when competing with wild males for wild females under field cage conditions. Dietary regimes were, one, with non‐hydrolysed brewer's yeast and sugar (1:3 ratio), and the other with brewer's yeast hydrolysate enzymatic and sugar (1:12 ratio). The effect was evaluated in four variables associated with mating success: number of copulas obtained, latency to mate, copula duration, and copula location. Exposure to volatiles did not affect the number of matings achieved, irrespective of the diet given to the males. When laboratory males were fed with brewer's yeast hydrolysate, the effect of volatile exposure was shown in latency to mate, copula duration, and copula location. When the laboratory males were fed with non‐hydrolysed brewer's yeast, the effect of volatile exposure was shown only in copula duration. Laboratory males fed brewer's yeast hydrolysate achieved the same number of matings as wild males, whereas laboratory males fed non‐hydrolysed brewer's yeast had lower performance. [ABSTRACT FROM AUTHOR]

Detecting volatile organic compounds (VOCs) emitted from different plant species and their organs can provide valuable information about plant health and environmental factors that affect them. For example, limonene emission can be a biomarker to monitor plant health and detect stress. Traditional methods for VOC detection encounter challenges, prompting the proposal of novel approaches. In this study, we proposed integrating electrospinning, molecular imprinting, and conductive nanofibers to fabricate limonene sensors. In detail, polyvinylpyrrolidone (PVP) and polyacrylic acid (PAA) served here as fiber and cavity formers, respectively, with multiwalled carbon nanotubes (MWCNT) enhancing conductivity. We developed one-step monolithic molecularly imprinted fibers, where S(−)-limonene was the target molecule, using an electrospinning technique. The functional cavities were fixed using the UV curing method, followed by a target molecule washing. This procedure enabled the creation of recognition sites for limonene within the nanofiber matrix, enhancing sensor performance and streamlining manufacturing. Humidity was crucial for sensor working, with optimal conditions at about 50% RH. The sensors rapidly responded to S(−)-limonene, reaching a plateau within 200 s. Enhancing fiber density improved sensor performance, resulting in a lower limit of detection (LOD) of 137 ppb. However, excessive fiber density decreased accessibility to active sites, thus reducing sensitivity. Remarkably, the thinnest mat on the fibrous sensors created provided the highest selectivity to limonene (Selectivity Index: 72%) compared with other VOCs, such as EtOH (used as a solvent in nanofiber development), aromatic compounds (toluene), and two other monoterpenes (α-pinene and linalool) with similar structures. These findings underscored the potential of the proposed integrated approach for selective VOC detection in applications such as precision agriculture and environmental monitoring. [ABSTRACT FROM AUTHOR]

Following a request from the European Commission, EFSA was asked to deliver a scientific opinion on the safety and efficacy of an essential oil obtained from the fruit of Apium graveolens L. (celery seed oil), when used as a sensory additive in feed and water for drinking for all animal species. The EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) Panel concluded that the use of celery seed oil is of no concern up to the following concentrations in complete feed: 1.6 mg/kg for chickens for fattening, 2.3 mg/kg for laying hens, 2.1 mg/kg for turkeys for fattening, 2.8 mg/kg for piglets, 3.3 mg/kg for pigs for fattening, 4.1 mg/kg for sows, 6.5 mg/kg for veal calves (milk replacer), 6.2 mg/kg for cattle for fattening, sheep, goats and horses, 4.0 mg/kg for dairy cows, 2.5 mg/kg for rabbits, 6.8 mg/kg for salmonids and 7.2 mg/kg for dogs. These conclusions were extrapolated to other physiologically related species. For cats, ornamental fish and other species, no conclusion can be drawn. The use of celery seed oil in animals feed is not expected to pose concern for the consumers and for the environment. The additive under assessment should be considered as an irritant to skin and eyes, and as a respiratory and skin sensitiser. When handling the essential oil, exposure of unprotected users to perillaldehyde and bergapten may occur. Therefore, to reduce the risk, the exposure of the users should be minimised. Since A. graveolens and its preparations were recognised to flavour food and its function in feed would be essentially the same as that in food, no further demonstration of efficacy was considered necessary. [ABSTRACT FROM AUTHOR]

Background: Limonene has a variety of applications in the foods, cosmetics, pharmaceuticals, biomaterials, and biofuels industries. In order to meet the growing demand for sustainable production of limonene at industry scale, it is essential to find an alternative production system to traditional plant extraction. A promising and eco-friendly alternative is the use of microbes as cell factories for the synthesis of limonene. Results: In this study, the oleaginous yeast Yarrowia lipolytica has been engineered to produce d- and l-limonene. Four target genes, l- or d-LS (limonene synthase), HMG (HMG-CoA reductase), ERG20 (geranyl diphosphate synthase), and NDPS1 (neryl diphosphate) were expressed individually or fused together to find the optimal combination for higher limonene production. The strain expressing HMGR and the fusion protein ERG20-LS was the best limonene producer and, therefore, selected for further improvement. By increasing the expression of target genes and optimizing initial OD, 29.4 mg/L of l-limonene and 24.8 mg/L of d-limonene were obtained. We also studied whether peroxisomal compartmentalization of the synthesis pathway was beneficial for limonene production. The introduction of d-LS and ERG20 within the peroxisome improved limonene titers over cytosolic expression. Then, the entire MVA pathway was targeted to the peroxisome to improve precursor supply, which increased d-limonene production to 47.8 mg/L. Finally, through the optimization of fermentation conditions, d-limonene production titer reached 69.3 mg/L. Conclusions: In this work, Y. lipolytica was successfully engineered to produce limonene. Our results showed that higher production of limonene was achieved when the synthesis pathway was targeted to the peroxisome, which indicates that this organelle can favor the bioproduction of terpenes in yeasts. This study opens new avenues for the efficient synthesis of valuable monoterpenes in Y. lipolytica. [ABSTRACT FROM AUTHOR]

The use of household bleach cleaning products results in emissions of highly oxidative gaseous species, such as hypochlorous acid (HOCl) and chlorine (Cl2). These species readily react with volatile organic compounds (VOCs), such as limonene, one of the most abundant compounds found in indoor enviroments. In this study, reactions of HOCl/Cl2 with limonene in the gas phase and on indoor relevant surfaces were investigated. Using an environmental Teflon chamber, we show that silica (SiO2), a proxy for window glass, and rutile (TiO2), a component of paint and self-cleaning surfaces, act as a reservoir for adsorption of gas-phase products formed between HOCl/Cl2 and limonene. Furthermore, high-resolution mass spectrometry (HRMS) shows that the gas-phase reaction products of HOCl/Cl2 and limonene readily adsorb on both SiO2 and TiO2. Surface-mediated reactions can also occur, leading to the formation of new chlorine- and oxygen-containing products. Transmission Fourier-transform infrared (FTIR) spectroscopy of adsorption and desorption of bleach and terpene oxidation products indicates that these chlorine- and oxygen-containing products strongly adsorb on both SiO2 and TiO2 surfaces for days, providing potential sources of human exposure and sinks for additional heterogeneous reactions.

Abstract Background Limonene has a variety of applications in the foods, cosmetics, pharmaceuticals, biomaterials, and biofuels industries. In order to meet the growing demand for sustainable production of limonene at industry scale, it is essential to find an alternative production system to traditional plant extraction. A promising and eco-friendly alternative is the use of microbes as cell factories for the synthesis of limonene. Results In this study, the oleaginous yeast Yarrowia lipolytica has been engineered to produce d- and l-limonene. Four target genes, l- or d-LS (limonene synthase), HMG (HMG-CoA reductase), ERG20 (geranyl diphosphate synthase), and NDPS1 (neryl diphosphate) were expressed individually or fused together to find the optimal combination for higher limonene production. The strain expressing HMGR and the fusion protein ERG20-LS was the best limonene producer and, therefore, selected for further improvement. By increasing the expression of target genes and optimizing initial OD, 29.4 mg/L of l-limonene and 24.8 mg/L of d-limonene were obtained. We also studied whether peroxisomal compartmentalization of the synthesis pathway was beneficial for limonene production. The introduction of d-LS and ERG20 within the peroxisome improved limonene titers over cytosolic expression. Then, the entire MVA pathway was targeted to the peroxisome to improve precursor supply, which increased d-limonene production to 47.8 mg/L. Finally, through the optimization of fermentation conditions, d-limonene production titer reached 69.3 mg/L. Conclusions In this work, Y. lipolytica was successfully engineered to produce limonene. Our results showed that higher production of limonene was achieved when the synthesis pathway was targeted to the peroxisome, which indicates that this organelle can favor the bioproduction of terpenes in yeasts. This study opens new avenues for the efficient synthesis of valuable monoterpenes in Y. lipolytica.

Kratai Cham (Adenosma indianum (Lour.) Merr.), similar to the camphor tree, produces fragrant essential oils rich in limonene found in glandular trichomes. These oils are renowned for their antibacterial, anti-inflammatory, and therapeutic properties in traditional medicine, particularly for neurodegenerative disorders. Recently, Kratai Cham has thrived in saline soils, prompting our investigation in Kalasin Province, Thailand, from 2019 to 2022. This research aimed to evaluate the influence of salinity on Kratai Cham, with particular relevance to its essential oils. The observation revealed that the life cycle of Kratai Cham spanned from July to February, and this cycle correlated with soil salinity, which ranged from 13.10 to 34.70 mmol Na/kg and 3.33 to 25.33 mmol Cl/kg. Salinity led to reduced stomatal size but increased numbers and indices of stomata and trichomes, notably the two glandular trichomes, capitate and peltate, on the lower epidermis. FTIR analysis revealed rising essential oil concentrations, particularly d-limonene, in response to salinity. Kratai Cham’s saline adaptations offer medical promise, underscoring the significance of this research for unlocking its potential.

Adenosine-5'-triphosphate (ATP), the primary energy currency in cellular processes, drives metabolic activities and biosynthesis. Despite its importance, understanding intracellular ATP dynamics' impact on bioproduction and exploiting it for enhanced bioproduction remains largely unexplored. Here, we harness an ATP biosensor to dissect ATP dynamics across different growth phases and carbon sources in multiple microbial strains. We find transient ATP accumulations during the transition from exponential to stationary growth phases in various conditions, coinciding with fatty acid (FA) and polyhydroxyalkanoate (PHA) production in Escherichia coli and Pseudomonas putida, respectively. We identify carbon sources (acetate for E. coli, oleate for P. putida) that elevate steady-state ATP levels and boost FA and PHA production. Moreover, we employ ATP dynamics as a diagnostic tool to assess metabolic burden, revealing bottlenecks that limit limonene bioproduction. Our results not only elucidate the relationship between ATP dynamics and bioproduction but also showcase its value in enhancing bioproduction in various microbial species. ATP dynamics influence bioproduction yet are largely unexplored in this context. Here, authors unravel ATP dynamics across various conditions, identify carbon sources which boost ATP levels and bioproduction, and uncover metabolic bottlenecks, shedding light on how ATP dynamics can be used to enhance bioproduction. [ABSTRACT FROM AUTHOR]

This study evaluated the chemical composition and anti-proliferative activity of essential oils (EOs) obtained by hydrodistillation from seven medicinal plants from Cachicadán, La Libertad Región, Perú. Limonene (0.64 to 44.43%) and linalool (0.36 to 2.12%) were identified in all EOs by gas chromatography coupled to mass spectrometry analysis. The major components (relative intensity ≥ 10%) were cis-dihydro carvone, carvone, and cis-piperitone epoxide for Minthostachys mollis leaves; β-pinene, limonene, and ledol for Lepechinia heteromorpha leaves; limonene, neral, and geranial for Aloysia citriodora, both leaves and flowers; α-pinene, and limonene for Myrcianthes myrsinoides leaves; and α-pinene, β-myrcene, and (E)-β-Ocimene for Dalea carthagenensis leaves. Constituted by (Z)-β-ocimene, dihydrotagetone, (Z)-tagetone, and car-3-en-2-one, EO of Tagetes minuta leaves induced an irreversible cytostatic effect against MCF-7 human breast tumor cells. Further in vivo studies must be carried out to establish the safe and efficient dose of T. minuta EO as adjuvant treatment in oncological therapies. [ABSTRACT FROM AUTHOR]

The present study is devoted to evaluate in vitro the chemical composition and the antioxidant and antibacterial properties of essential oils (Eo) extracted by hydrodistillation (HD) and microwave (MW) from the plant peels of Citrus sinensis. The extraction provided yields of 0.26% and 0.02%, respectively. The essential oils were analyzed by GC–MS whose major component is limonene that has a remarkable percentage (78.192% and 58.6%, respectively) for the essential oil extracted by HD and MW. The results of the antioxidant potential were noticeable in each of the essential oils with a higher priority to that extracted by hydrodistillation. The evaluation of the antioxidant power by the free radical scavenging method (DPPH) showed that the essential oils studied have good antioxidant activity, especially for the oil extracted by HD having presented an IC50 of (13.07 ± 0.169) mg/ml, while BHT and ascorbic acid showed very potent and effective anti-free radical activity with IC50 of the order of (19.54 ± 0.32) µg/ml and (1.17 ± 0.05) µg/ml respectively. According to the β-carotene/linoleic acid test, the oxidation of β-carotene was effectively inhibited by the two essential oils of Citrus sinensis peels with a percentage of inhibition of (56.46 ± 0.76) % and (31.39 ± 1.49) % respectively for HD and MW. Eo extracted by HD is more active than ascorbic acid (15.43%). In the antibacterial test, the activity was evaluated by the disc-diffusion method, the two types of sweet orange essential oils inhibited the growth of five bacterial strains out of six: The best activity was obtained against E. coli, Listeria monocytogenes, and Agrobacterium with a diameter of the zone of inhibition between 70 and 84 mm, with the exception of the strain of Bacillus subtilis, there is no zone of inhibition has been observed. [ABSTRACT FROM AUTHOR]

In the era of ecology and careful care for the environment, it becomes important to use renewable raw materials of plant origin, which are often more easily available and cheaper. One of the important and rapidly developing directions of research are works related to the use of waste plant biomass; an example of this trend is the production of activated carbons from food industry waste. One of the examples of the application of derived from biomass activated carbons can be using them as catalysts for the isomerization of terpene compounds. Carbons based on waste biomass are characterized by the minimal amount of waste formation during their manufacture, and their use in the isomerization reaction allows to obtain high conversion of organic raw material and high selectivities of transformation to the desired products, making these carbons environmentally friendly substitutes for the catalysts used usually in this process. In this work, obtained carbonaceous catalysts were tested in the process of isomerization of α-pinene to high value chemicals (mainly camphene and limonene). Under the most favorable conditions (activated carbon from sunflower husks content in reaction mixture 5 wt%, temperature 180 °C, and reaction time 100 min), α-pinene was completely converted (conversion 100 mol%) with high selectivity towards camphene (54 mol%). To prepare activated carbons, biomass precursors (orange peels, sunflower husks, spent coffee grounds) were activated with 85% H3PO4 through the chemical activation. The obtained materials were characterized by such methods as sorption N2 at − 196 °C, X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), scanning electron microscope (SEM), and X-ray fluorescence (XRF) to determine the relationship between their textural-chemical properties and catalysts activity in isomerization process. The synthesized materials were characterized by a specific surface area in the range of 930–1764 m2, total pore volume in the range of 0.551–1.02 cm3/g, and total acid-site concentrations in the range of 1.47–2.33 mmol/g. These results showed that textural parameters of the obtained activated carbons have the important role in the isomerization of α-pinene. [ABSTRACT FROM AUTHOR]

Terpenoids have extensive pharmacological activities and are extensively applied in the pharmaceutical, cosmetic, and food industries. Increasing the structural diversity of terpenoids would expand their potential applications. Noncanonical backbones can be generated by coexpressing the canonical mevalonate pathway and C-methyltransferases, or the lepidopteran mevalonate pathway, in engineered strains. The design and chemical synthesis of farnesyl pyrophosphate analogs to create unnatural terpenoids promises two advantages: it complements other methods of terpene synthesis and bypasses the task of engineering entire metabolic pathways to produce alternative substrates in vivo. The artificial metalloenzyme Ir(Me)-porphyrin IX CYP119 allows cyclopropanation of limonene to synthesize high titers of unnatural products with high diastereoselectivity. Terpenoids display chemical and structural diversities as well as important biological activities. Despite their extreme variability, the range of these structures is limited by the scope of natural products that canonically derive from interconvertible five-carbon (C5) isoprene units. New approaches have recently been developed to expand their structural diversity. This review systematically explores the combinatorial biosynthesis of noncanonical building blocks via the coexpression of the canonical mevalonate (MVA) pathway and C-methyltransferases (C-MTs), or by using the lepidopteran mevalonate (LMVA) pathway. Unnatural terpenoids can be created from farnesyl diphosphate (FPP) analogs by chemobiological synthesis and terpene cyclopropanation by artificial metalloenzymes (ArMs). Advanced technologies to accelerate terpene biosynthesis are discussed. This review provides a valuable reference for increasing the diversity of valuable terpenoids and their derivatives, as well as for expanding their potential applications. [ABSTRACT FROM AUTHOR]

Terpenoids are defense metabolites that are induced upon infection or wounding. However, their role in systemic‐induced resistance (SIR) is not known. Here, we explored the role of terpenoids in this phenomenon at a very early stage in the interaction between Austrian pine and the tip blight and canker pathogen Diplodia pinea. We induced Austrian pine saplings by either wounding or inoculating the lower stems with D. pinea. The seedlings were then challenged after 12 h, 72 h, or 10 days with D. pinea on the stem 15 cm above the induction. Lesion lengths and terpenoids were quantified at both induction and challenge locations. Key terpenoids were assayed for antifungal activity in in vitro bioassays. SIR increased with time and was correlated with the inducibility of several compounds. α‐Pinene and a cluster of β‐pinene, limonene, benzaldehyde, dodecanol, and n‐dodecyl acrylate were positively correlated with SIR and were fungistatic in vitro, while other compounds were negatively correlated with SIR and appeared to serve as a carbon source for D. pinea. This study shows that, overall, terpenoids are involved in SIR in this system, but their role is nuanced, depending on the type of induction and time of incubation. We hypothesize that some, such as α‐pinene, could serve in SIR signaling. Summary statement: Trees can resist recurring pathogenic attacks using memory of successful prior encounters with pest or pathogens. Here we show that pathogenic induction results in systemic and selective accumulation of certain terpenoids and other non‐terpenoids in trees conferring higher resistance against newer infection. [ABSTRACT FROM AUTHOR]

The goal of this work was to investigate the chemical composition of Aloysia citriodora essential oil and its biological activities as antioxidant, antibacterial, antifungal and anti-inflammatory potentials depending on the collection region. The highest essential oil yields were in Gabes and Kairouan at the Arid bioclimatic zone. Sixty volatile compounds were identified by GC-FID-MS. The major compounds were limonene and spathulenol in Gabes at the Middle Arid. However, (E)-citral (known as geranial) was the major compound of Belli and Kairouan belonging to the Upper Semi-Arid and Upper Arid areas, respectively. The essential oil extracted from the inferior sub-humid bioclimatic zone (Boussalem) had spathulenol and caryophyllene oxide as predominant components. Inversely to DPPH and ABTS, the antioxidant activities using reducing power assay of A. citriodora essential oils significantly increased from the inferior sub-humid (Boussalem) to the Upper Arid (Kairouan) bioclimatic areas. Independently of region, A. citriodora essential oil exhibited an interesting antibacterial, antifungal and anti-inflammatory potential. [ABSTRACT FROM AUTHOR]

Solidago virgaurea L. popularly called Goldenrod is a member of the Asteraceae family. S. virgaurea sample were obtained from Binsar, Almora (Indian state of Uttarakhand). The essential oil from the aerial part was distilled out using steam distillation, and GC and GC-MS were employed for analysis. A total of 27 constituents from aerial part were identified constituting 92.92% of total oil composition. The aerial parts of S. virgaurea were found to contain limonene (25.57%), α-humulene (12.19%), linalool oxide (8.65%), benzyl salicylate (6.40%), 1,4-cineole (6.22%) and humulene epoxide (II) (5.93%). The antibacterial activity of this essential oil was studied using disk diffusion and broth microdilution methods on five human pathogen bacteria and six plant pathogenic bacteria. There was moderate to good antibacterial activity in the oil sample extracted from the entire aerial portion of the plant. We did the antileishmanial activity of essential oils with Leishmania donovani (Dd8) promastigotes and intracellular amastigotes. EO was safer on the J774.A1 macrophages and lethal to promastigotes and intracellular amastigotes at different concentrations (10, 50, and 100 μg/ mL). These findings support the traditional uses of S. virgaurea and suggest its potential as a natural remedy for bacterial infections and leishmaniasis. [ABSTRACT FROM AUTHOR]

Essential oils isolated from leaves, twigs, fruit bark and seeds of Michelia tonkinensis collected in Muong Nhe Nature Reserve, Dien Bien province were obtained by hydrodistillation with yields of 1.5, 0.42, 0.16 and 4.6% respectively (v/w on dry weight basis). After analysis through GC, GC-MS and 13C NMR, 30, 34, 31 and 13 compounds (representing 96.4%, 96.8%, 97.1% and 99.9% of the whole composition, respectively) were identified in the leave, twig, fruit bark and seed essential oils. The main components were limonene (43.2%) and germacrene D (32.7%) in the leaf oil; limonene (67.1%) and germacrene D (10.4%) in the twig oil; limonene (66%) in the fruit bark oil; and safrole (90%) in the seed oil. Essential oils from the leaves and twigs showed strong inhibition against Staphyloccocus aureus. The fruit bark essential oil exhibited greater antibacterial potential against all 3 tested microorganisms (S. aureus, Escherichia coli and Candida albicans). The essential oil from seed displayed weak antibacterial activity against the three tested microorganisms. [ABSTRACT FROM AUTHOR]

Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae) is an insect pest with great socio-economic importance in different agricultural regions worldwide. This species is highly adaptive and polyphagous, feeding on wild and cultivated host plants. Successive pesticide applications, which negatively affect the environment, are mainly used for managing H. armigera. Studies have investigated alternative methods with low environmental and socioeconomic impacts, including using essential oils. Essential oils are secondary plant-derived metabolites with insecticidal activity in different insect pest populations. Thus, the objective of this study was to evaluate the insecticidal activity of essential oils of Citrus aurantium (Linnaeus) (Rutaceae) and Citrus sinensis (Linnaeus) (Rutaceae) as well as their major component limonene on the biology and reproduction of H. armigera. The essential oils were characterized using gas chromatography-mass spectrometry. Further, their toxicity and the effects of their lethal and sublethal concentrations in larvae and on biological and reproductive parameters in adults were evaluated. All treatments exhibited insecticidal activity and lethal and sub-lethal effects on the biology and reproduction of H. armigera. Therefore, these essential oils could be used to control H. armigera. [ABSTRACT FROM AUTHOR]

Essential oils (EOs) from Citrus sinensis (Rutaceae) possess diverse biological activities. However, a comprehensive comparison of their chemical composition and bioactivity across different plant parts has not been studied yet. The current research comparatively assesses the yield, chemical composition, chiral distribution, antioxidant properties, and larvicidal activity of EOs extracted from the peels, leaves, and flowers of C. sinensis. EOs extracted via hydro-distillation (HD) and steam distillation (SD) were analyzed by gas chromatography–mass spectrometry (GC-MS) and chiral GC-MS to explore their chemical composition and enantiomeric distribution. In addition, their larvicidal and antioxidant potentials were evaluated following standard protocols. Peels of C. sinensis exhibited significantly higher oil content (1.75–2.25%) compared to its leaves (0.75–0.78%) and flowers (0.20–0.25%). The GC-MS analysis identified around 60 compounds, including terpenoids, sesquiterpenoids, and oxygenated terpenoids in the HD and SD extractions. Higher concentrations of sabinene were found in flower extract (38.05–39.89%) and leaf extract (32.30–36.91%), while peel extract contained more than 90% limonene. The larvicidal activity of peel oil was primarily attributed to limonene, with an LC50 value of 0.0031 µL/mL. The current study reports the first chiral (GC-MS) analysis in the essential oil of the leaves and flowers of C. sinensis, paving the way for authenticity and purity. Furthermore, the chemical profiling of citrus EOs, particularly from the peel, demonstrates a safe and promising candidate for diverse biological applications. [ABSTRACT FROM AUTHOR]

The current technique to assess glove resistance to chemicals for worker protection relies on challenging a flat, 2.54 cm diameter glove piece at or near room temperature. This does not simulate a donned whole glove near the skin temperature subjected to work activity forces. Four different types of disposable nonpowdered unlined/unsupported nitrile gloves in triplicate were measured for thickness, porosity, and for the acrylonitrile content (A) of the challenge and collection sides. Limonene permeation at 35 °C through a whole glove on a clenching and nonclenching dextrous robot hand and with the standard ASTM F739 technique were facilitated by taking samples from the collection sides for GC-MS analysis. The standardized breakthrough time (SBT) when permeation reached 100 ng/cm2/min and the steady state permeation rate (SSPR) depended on A, thickness, and porosity. Only the thinnest glove (Lavender) showed statistically significant (p ≤ 0.05) increased average SSPR for the clenching hand relative to the nonclenching hand and for the ASTM technique. The ASTM test data for the three thickest gloves were not statistically different from those of the robot hand, but differed from the manufacturer's. More research with different chemicals and higher clenching forces is needed. Clenching forces can enhance the permeation. Workers wearing ultrathin disposable nitrile gloves have a higher potential for chemical penetration/permeation. Company glove permeation data obtained near room temperature may have a longer SBT and lower SSPR than in practice. Double gloving may be advisible in emergencies and for unknown chemicals when no appropriate thicker Chemical Protective glove is available. [ABSTRACT FROM AUTHOR]

Hagenia abyssinica and Artemisia absinthium are widely distributed tree species in Ethiopia and known for their traditional medicinal uses. The present study was conducted to determine the essential oil and smoke constituents of H. abyssinica and A. absinthium leaves using GC-MS. The main components of the A. absinthium essential oil were valencene (5.48%), bornyl acetate (5.15%), and trans-cinnamic acid (4.34%). 2-Bornanone (18.54%), o-cymene (12.80%), and nerolidol (7.04%) were the dominant components of the MeOH fraction of the smoke derived from the leaves of A. absinthium, while 2-propenoic acid butyl ester (46.49%), heptadecane (10.66%), and 9-octylheptadecane (7.78%) were the major components of the n-hexane fraction. The main components of the H. abyssinica essential oil were cis-davanone (14.73%), Aristolediene (9.31%), and cryptone (6.50%). β-Myrcene (12.59%), neophytadiene (11.54%), and limonene (11.27%) were the dominant components of the MeOH fraction of the smoke derived from the leaves of H. abyssinica. 1,3,5,7-Cyclooctatetraene (33.58%), prehnitene (7.01%), and heptadecane (5.46%) were the dominant components of the n-hexane fraction of the smoke derived from the leaves of H. abyssinica. The smoke components of A. absinthium and H. abyssinica were reported here for the first time. [ABSTRACT FROM AUTHOR]

Native and exotic fruits from the Amazon have varied characteristics, with aroma being a decisive factor in their acceptance for medicinal use as a nutraceutical supplement. This work aimed to analyze the chemical constituents of the volatile concentrates of some Myrtaceous fruit species sampled in the Brazilian Amazon. The fruit's pulps were subjected to simultaneous distillation–extraction, and gas chromatography–mass spectrometry was used to analyze their volatile chemical composition. In the volatile concentrate of Eugenia stipitata (Araçá-boi) α-pinene (17.5%), citronellyl butanoate (15.6%), and pogostol (13.5%) were identified as primary constituents; Eugenia uniflora (Ginja) concentrate comprised curzerene (30.5%), germacrone (15.4%), atractylone (13.1%), and (E)-β-ocimene (11.1%); in Myrciaria dubia (Camu-Camu), α-pinene (55.8%), (E)-β-ocimene (13.1%), and α-terpineol (10.0%) were present; in Psidium guajava (Goiaba) were (2E)-hexenal (21.7%), hexanal (15.4%), caryophylla-4(12),8(13)-dien-5-β-ol (10.5%), caryophyllene oxide (9.2%), and pogostol (8.3%); and in Psidium guineense (Araçá), limonene (25.2%), ethyl butanoate (12.1%), epi-β-bisabolol (9.8%), and α-pinene (9.2%) were the main constituents. The analyzed volatile concentrates of these fruit species presented a significant diversity of constituents with a predominance of functional groups, such as monoterpenes, sesquiterpenes, and fatty acid derivatives, originating from the plant's secondary metabolism and playing an important role in their nutritional and medicinal uses. [ABSTRACT FROM AUTHOR]

As part of our continuing interest in the essential oil compositions of gymnosperms, particularly the distribution of chiral terpenoids, we have obtained the foliar essential oils of Chamaecyparis lawsoniana (two samples), Thuja plicata (three samples), and Tsuga heterophylla (six samples) from locations in the state of Oregon, USA. The essential oils were obtained via hydrodistillation and analyzed by gas chromatographic techniques, including chiral gas chromatography—mass spectrometry. The major components in C. lawsoniana foliar essential oil were limonene (27.4% and 22.0%; >99% (+)-limonene), oplopanonyl acetate (13.8% and 11.3%), beyerene (14.3% and 9.0%), sabinene (7.0% and 6.5%; >99% (+)-sabinene), terpinen-4-ol (5.0% and 5.3%; predominantly (+)-terpinen-4-ol), and methyl myrtenate (2.0% and 5.4%). The major components in T. plicata essential oil were (−)-α-thujone (67.1–74.6%), (+)-β-thujone (7.8–9.3%), terpinen-4-ol (2.7–4.4%; predominantly (+)-terpinen-4-ol), and (+)-sabinene (1.1–3.5%). The major components in T. heterophylla essential oil were myrcene (7.0–27.6%), α-pinene (14.4–27.2%), β-phellandrene (6.6–19.3%), β-pinene (6.4–14.9%; >90% (−)-β-pinene), and (Z)-β-ocimene (0.7–11.3%). There are significant differences between the C. lawsoniana essential oils from wild trees in Oregon and those of trees cultivated in other geographical locations. The essential oil compositions of T. plicata are very similar, regardless of the collection site. There are no significant differences between T. heterophylla essential oils from the Oregon Coastal Range or those from the Oregon Cascade Range. Comparing essential oils of the Cupressaceae with the Pinaceae, there are some developing trends. The (+)-enantiomers seem to dominate for α-pinene, camphene, sabinene, β-pinene, limonene, terpinen-4-ol, and α-terpineol in the Cuppressaceae. On the other hand, the (−)-enantiomers seem to predominate for α-pinene, camphene, β-pinene, limonene, β-phellandrene, terpinen-4-ol, and α-terpineol in the Pinaceae. [ABSTRACT FROM AUTHOR]

Background: Neurodegeneration is a term describing an irreversible process of neuronal damage. In recent decades, research efforts have been directed towards deepening our knowledge of numerous neurodegenerative disorders, with a particular focus on conditions such as Alzheimer's disease (AD). Human transferrin (htf) is a key player in maintaining iron homeostasis within brain cells. Any disturbance in this equilibrium gives rise to the emergence of neurodegenerative diseases and associated pathologies, particularly AD. Limonene, a natural compound found in citrus fruits and various plants, has shown potential neuroprotective properties. Objective: In this study, our goal was to unravel the binding of limonene with htf, with the intention of comprehending the interaction mechanism of limonene with htf. Methods: Binding was scrutinized using fluorescence quenching and UV-Vis spectroscopic analyses. The binding mechanism of limonene was further investigated at the atomic level through molecular docking and extensive 200 ns molecular dynamic simulation (MD) studies. Results: Molecular docking uncovered that limonene interacted extensively with the deep cavity located within the htf binding pocket. MD results indicated that binding of limonene to htf did not induce substantial structural alterations, ultimately forming stable complex. The findings from fluorescence binding indicated a pronounced interaction between limonene and htf, limonene binds to htf with a binding constant (K) of 0.1×105 M–1. UV spectroscopy also advocated stable htf-limonene complex formation. Conclusions: The study deciphered the binding mechanism of limonene with htf, providing a platform to use limonene in AD therapeutics in context of iron homeostasis. [ABSTRACT FROM AUTHOR]

Monoterpenes and monoterpenoids such as (S)-limonene and geraniol are valuable chemicals with a wide range of applications, including cosmetics, pharmaceuticals, and biofuels. Saccharomyces cerevisiae has proven to be an effective host to produce various terpenes and terpenoids. (S)-limonene and geraniol are produced from geranyl pyrophosphate (GPP) through the enzymatic actions of limonene synthase (LS) and geraniol synthase (GES), respectively. However, a major hurdle in their production arises from the dual functionality of the Erg20, a farnesyl pyrophosphate (FPP) synthase, responsible for generating GPP. Erg20 not only synthesizes GPP by condensing isopentenyl pyrophosphate (IPP) with dimethylallyl pyrophosphate but also catalyzes further condensation of IPP with GPP to produce FPP. In this study, we have tackled this issue by harnessing previously developed Erg20 mutants, Erg20K197G (Erg20G) and Erg20F96W, N127W (Erg20WW), which enhance GPP accumulation. Through a combination of these mutants, we generated a novel Erg20WWG mutant with over four times higher GPP accumulating capability than Erg20WW, as observed through geraniol production levels. The Erg20WWG mutant was fused to the LS from Mentha spicata or the GES from Catharanthus roseus for efficient conversion of GPP to (S)-limonene and geraniol, respectively. Further improvements were achieved by localizing the entire mevalonate pathway and the Erg20WWG-fused enzymes in peroxisomes, while simultaneously downregulating the essential ERG20 gene using the glucose-sensing HXT1 promoter. In the case of (S)-limonene production, additional Erg20WWG-LS was expressed in the cytosol. As a result, the final strains produced 1063 mg/L of (S)-limonene and 1234 mg/L of geraniol by fed-batch biphasic fermentations with ethanol feeding. The newly identified Erg20WWG mutant opens doors for the efficient production of various other GPP-derived chemicals including monoterpene derivatives and cannabinoids. • Monoterpenes were produced in S. cerevisiae via enhancing GPP accumulation. • Erg20WWG (F96W, N127W and K197G) mutant increases GPP accumulation. • Erg20WWG fusion with geraniol or (S)-limonene synthase enhances target production. • Peroxisomal compartmentalization of the biosynthetic pathway increases production. • 1.23 g/L geraniol and 1.06 g/L (S)-limonene were produced with ethanol feeding. [ABSTRACT FROM AUTHOR]

Simple Summary: The two closely related maize and rice weevils exhibit differential host preferences among stored maize, wheat, and paddy grains. The maize weevil adults prefer to select maize, followed by paddy and wheat, while rice weevil adults mainly migrate towards wheat. The 2-ethylhexanol, piperitone, and (+)-Δ-cadiene are the major components in volatiles from both maize and wheat, but the abundance of these chemicals is much lower in maize than in wheat. The volatile limonene was only detected in paddy. The 2-ethylhexanol, piperitone, and (+)-Δ-cadiene were all attractive to both weevils, whereas limonene was attractive only to rice weevils. The different volatile profiles among the grains and the sensitivity of the two pest species towards these volatiles may explain the behavioral differences between maize and rice weevils in selecting host grains. The variance in sensitivity of maize and rice weevils towards host volatile chemicals with abundance differences is likely a determinant driving the two insect species to migrate towards different host grains. The Sitophilus zeamais (maize weevil) and Sitophilus oryzae (rice weevil) are two insect pests that have caused huge economic losses to stored grains worldwide. It is urgent to develop an environmentally friendly strategy for the control of these destructive pests. Here, the olfactory-mediated selection preference of the two weevil species to three stored grains was analyzed, which should help establish a pull–push system in managing them. Bioassays showed that maize weevil adults prefer to select maize, followed by paddy and wheat, while rice weevil adults mainly migrate towards wheat. Volatile analyses revealed that 2-ethylhexanol, piperitone, and (+)-Δ-cadiene are the major components in volatiles from both maize and wheat, but the abundance of these chemicals is much lower in maize than that in wheat. The volatile limonene was only detected in paddy. Y-tube bioassays suggest that 2-ethylhexanol, piperitone, and (+)-Δ-cadiene were all attractive to both weevils, whereas limonene was attractive only to rice weevils. Overall, maize weevil appeared more sensitive to the tested volatiles based on having much lower effective concentrations of these volatiles needed to attract them. The differences in volatile profiles among the grains and the sensitivity of the two species towards these volatiles may explain the behavioral differences between maize and rice weevils in selecting host grains. The differences in sensitivity of maize and rice weevils towards host volatile components with abundance differences are likely determinants driving the two insect species to migrate towards different host grains. [ABSTRACT FROM AUTHOR]

In this study, we investigate the reaction between water and the cis and trans limonene oxide mixture in the presence of ethyl carbamate ((R)-N-(α-methyl-benzyl)ethyl-carbamate), producing (1 R, 2 R, 4 R)-limonene-1,2-diol and trans limonene oxide. This study is carried out using the quantum mechanical density functional theory (DFT) method B3LYP-D3/6-31+G (d,p) to theoretically explain that 1,2-limonene diol is the hydrolysis product derived from cis limonene oxide, with trans limonene oxide not reacting (regioselectivity). For this reason, we exploit Fukui's frontier molecular orbital theory (FMO), local softness and local hardness ratios, transition states of the obtained products, the Fukui indices, and the thermodynamic quantities (enthalpy, entropy, free energy calculations). The theoretical results effectively elucidate the observed regioselectivity and corroborate the experimental findings. [ABSTRACT FROM AUTHOR]

Two commercial biopesticides were studied to determine their persistence in two soil types, such as sandy clay loam and clay loam soils. For this purpose, an orange oil–based biopesticide was used, being limonene its main ingredient. The other biopesticide was based on cinnamon extract and trans-cinnamaldehyde as its main component. Degradation of these compounds was monitored, and transformation products or metabolites were detected. Limonene and its metabolites were analyzed by gas chromatography (GC) and trans-cinnamaldehyde by ultra-high-performance liquid chromatography (UHPLC). Both techniques were coupled to a high-resolution mass (HRMS) analyzer, such as quadrupole (Q)-Orbitrap. Limonene and trans-cinnamaldehyde were rapidly degraded as result of first-order kinetics. Possible metabolites such as thymol, cymene, isoterpinolene and cymenene for limonene, and hydroxycinnamic acid for trans-cinnamaldehyde were tentatively identified. Moreover, four other metabolites of trans-cinnamaldehyde, some of them not previously described, were also detected. [ABSTRACT FROM AUTHOR]

The citrus plant is the general term for Citrus, Fortunella, and Poncirus, which includes oranges, tangerines, lemons, grapefruits, and citrons. Not only does it contain a variety of delicious fruits, but it is also an important part of traditional Chinese medicine. Citrus plant peels are rich in essential oils, the primary active component of which is limonene. Modern pharmacological research has revealed that limonene has many pharmacological effects, including antibacterial, anticancer, analgesic, immune regulation, neuroprotection, antioxidant, anti-inflammatory properties, and the treatment of metabolic diseases. It finds widespread application in a variety of industries, including cosmetics, food, personal care, medicine, pesticides, and others. This article reviews the pharmacological effects of limonene from citrus plants to build a scientific basis for future limonene research and application and also to lay the groundwork for developing functional foods for the prevention and management of linked disorders. [ABSTRACT FROM AUTHOR]

The pharmacological effects of limonene, especially their derivatives, are currently at the forefront of research for drug development and discovery as well and structure-based drug design using huge chemical libraries are already widespread in the early stages of therapeutic and drug development. Here, various limonene derivatives are studied computationally for their potential utilization against the capsid protein of Herpes Simplex Virus-1. Firstly, limonene derivatives were designed by structural modification followed by conducting a molecular docking experiment against the capsid protein of Herpes Simplex Virus-1. In this research, the obtained molecular docking score exhibited better efficiency against the capsid protein of Herpes Simplex Virus-1 and hence we conducted further in silico investigation including molecular dynamic simulation, quantum calculation, and ADMET analysis. Molecular docking experiment has documented that Ligands 02 and 03 had much better binding affinities (− 7.4 kcal/mol and − 7.1 kcal/mol) to capsid protein of Herpes Simplex Virus-1 than Standard Acyclovir (− 6.5 kcal/mol). Upon further investigation, the binding affinities of primary limonene were observed to be slightly poor. But including the various functional groups also increases the affinities and capacity to prevent viral infection of the capsid protein of Herpes Simplex Virus-1. Then, the molecular dynamic simulation confirmed that the mentioned ligands might be stable during the formation of drug-protein complexes. Finally, the analysis of ADMET was essential in establishing them as safe and human-useable prospective chemicals. According to the present findings, limonene derivatives might be a promising candidate against the capsid protein of Herpes Simplex Virus-1 which ultimately inhibits Herpes Simplex Virus-induced encephalitis that causes interventions in brain inflammation. Our findings suggested further experimental screening to determine their practical value and utility. [ABSTRACT FROM AUTHOR]

Orange peels (OPs) were valorized in a lab-scale biorefinery loop for the recovery of limonene and the subsequent production of volatile fatty acids (VFAs) and activated carbon (AC). Solid/liquid extraction of limonene was optimized using n-hexane at 85 °C with an OPs-to-solvent ratio of 2:1, allowing for a limonene recovery yield of 1.20% w/w. Then, post-extraction OPs were used for the production of both VFAs and AC. For VFA production, a hydraulic retention time (HRT) of 5 days and a total solid (TS) inlet content of 10% w/w were adopted leading to a VFA yield of about 43% gVFAs/gTS. Adsorption tests revealed that, among all the solid matrixes tested, only powdered activated carbon (PAC) was able to discriminate no-VFA compounds and allowed for VFA purification. For AC production, post-extraction OPs were firstly converted into biochar through slow pyrolysis at 550 °C for 1 h and then physically activated with CO2 at 880 °C for 1 h. Extraction did not appreciably affect OP properties, while pyrolysis increased the carbon content (from 43 to 83%) and the heating value (from 17 to 29 MJ/kg) of the material. Physical activation of OP biochar increased its surface area by almost ten times, from 40 to 326 m2/g, proving the effectiveness of the treatment. [ABSTRACT FROM AUTHOR]

Background: The fruity aromatic bouquet of coffee has attracted recent interest to differentiate high value market produce as specialty coffee. Although the volatile compounds present in green and roasted coffee beans have been extensively described, no study has yet linked varietal molecular differences to the greater abundance of specific substances and support the aroma specificity of specialty coffees. Results: This study compared four Arabica genotypes including one, Geisha Especial, suggested to generate specialty coffee. Formal sensory evaluations of coffee beverages stressed the importance of coffee genotype in aroma perception and that Geisha Especial-made coffee stood out by having fine fruity, and floral, aromas and a more balanced acidity. Comparative SPME–GC–MS analyses of green and roasted bean volatile compounds indicated that those of Geisha Especial differed by having greater amounts of limonene and 3-methylbutanoic acid in agreement with the coffee cup aroma perception. A search for gene ontology differences of ripening beans transcriptomes of the four varieties revealed that they differed by metabolic processes linked to terpene biosynthesis due to the greater gene expression of prenyl-pyrophosphate biosynthetic genes and terpene synthases. Only one terpene synthase (CaTPS10-like) had an expression pattern that paralleled limonene loss during the final stage of berry ripening and limonene content in the studied four varieties beans. Its functional expression in tobacco leaves confirmed its functioning as a limonene synthase. Conclusions: Taken together, these data indicate that coffee variety genotypic specificities may influence ripe berry chemotype and final coffee aroma unicity. For the specialty coffee variety Geisha Especial, greater expression of terpene biosynthetic genes including CaTPS10-like, a limonene synthase, resulted in the greater abundance of limonene in green beans, roasted beans and a unique citrus note of the coffee drink. [ABSTRACT FROM AUTHOR]

Nowadays, the effective processing of natural monoterpenes that constitute renewable biomass found in post-production waste into products that are starting materials for the synthesis of valuable compounds is a way to ensure independence from non-renewable fossil fuels and can contribute to reducing global carbon dioxide emissions. The presented research aims to determine, based on DFT calculations, the activity and reactivity of limonene, an organic substrate used in previous preparative analyses, in comparison to selected monoterpenes such as cymene, pinene, thymol, and menthol. The influence of the solvent model was also checked, and the bonds most susceptible to reaction were determined in the examined compounds. With regard to EHOMO, it was found that limonene reacts more easily than cymene or menthol but with more difficultly than thymol and pienene. The analysis of the global chemical reactivity descriptors "locates" the reactivity of limonene in the middle of the studied monoterpenes. It was observed that, among the tested compounds, the most reactive compound is thymol, while the least reactive is menthol. The demonstrated results can be a reference point for experimental work carried out using the discussed compounds, to focus research on those with the highest reactivity. [ABSTRACT FROM AUTHOR]

Essential oils have been identified as effective natural compounds to prevent bacterial infections and thus are widely proposed as bioactive agents for biomedical applications. Across the literature, various essential oils have been incorporated into electrospun fibres to produce materials with, among others, antibacterial, anti-inflammatory and antioxidant activity. However, limited research has been conducted so far on the effect of these chemical products on the physical characteristics of the resulting composite fibres for extended periods of time. Within this work, electrospun fibres of poly(lactic acid) (PLA) were loaded with the essential oil limonene, and the impact of storage conditions and duration (up to 12 weeks) on the thermal degradation, glass transition temperature and mechanical response of the fibrous mats were investigated. It was found that the concentration of the encapsulated limonene changed over time and thus the properties of the PLA–limonene fibres evolved, particularly in the first two weeks of storage (independently from storage conditions). The amount of limonene retained within the fibres, even 4 weeks after fibre generation, was effective to successfully inhibit the growth of model microorganisms Escherichia coli, Staphylococcus aureus and Bacillus subtilis. The results of this work demonstrate the importance of evaluating physical properties during the ageing of electrospun fibres encapsulating essential oils, in order to predict performance modification when the composite fibres are used as constituents of medical devices. [ABSTRACT FROM AUTHOR]

Epoxidized vegetable oils and limonene dioxide, a bis-epoxide derived from the terpene limonene, are photo-copolymerized to yield highly crosslinked networks with high conversion of all epoxide groups at ambient temperature. However, the slow polymerization of such biobased formulation polymerizes is not compatible for a use in a commercial SLA 3D printer. Adding an acrylated epoxidized vegetable oil to the bis-epoxide leads to a decrease of curing time and an increase in LDO conversion to polymer. For example, in a 60:40 wt:wt mixture of LDO and epoxidized soybean oil, the conversions of both exocyclic and endocyclic epoxide groups of LDO are ≥95%. These formulations were successfully used in SLA 3D printers, leading to generation of hard and dry complex objects using biobased formulations. [ABSTRACT FROM AUTHOR]

Terpenes are high-value chemicals which can be produced by engineered cyanobacteria from sustainable resources, solar energy, water and CO2. We previously reported that the euryhaline unicellular cyanobacteria Synechocystis sp. PCC 6803 (S.6803) and Synechococcus sp. PCC 7002 (S.7002) produce farnesene and limonene, respectively, more efficiently than other terpenes. In the present study, we attempted to enhance farnesene production in S.6803 and limonene production in S.7002. Practically, we tested the influence of key cyanobacterial enzymes acting in carbon fixation (RubisCO, PRK, CcmK3 and CcmK4), utilization (CrtE, CrtR and CruF) and storage (PhaA and PhaB) on terpene production in S.6803, and we compared some of the findings with the data obtained in S.7002. We report that the overproduction of RubisCO from S.7002 and PRK from Cyanothece sp. PCC 7425 increased farnesene production in S.6803, but not limonene production in S.7002. The overexpression of the crtE genes (synthesis of terpene precursors) from S.6803 or S.7002 did not increase farnesene production in S.6803. In contrast, the overexpression of the crtE gene from S.6803, but not S.7002, increased farnesene production in S.7002, emphasizing the physiological difference between these two model cyanobacteria. Furthermore, the deletion of the crtR and cruF genes (carotenoid synthesis) and phaAB genes (carbon storage) did not increase the production of farnesene in S.6803. Finally, as a containment strategy of genetically modified strains of S.6803, we report that the deletion of the ccmK3K4 genes (carboxysome for CO2 fixation) did not affect the production of limonene, but decreased the production of farnesene in S.6803. [ABSTRACT FROM AUTHOR]