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Journal articles on the topic "Limonin"
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Yang, Jingguo, Yuhong Hu, and Kuan Chang. "Limonin Derivatives via Hydrogenation: Structural Identification and Anti-Inflammatory Activity Evaluation." Applied Sciences 12, no. 21 (November 4, 2022): 11169. http://dx.doi.org/10.3390/app122111169.
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Limonin is a natural compound which is rich in the fruit of various plants of the Rutaceae family and demonstrated to have a wide range of biological activities. In this work, seven limonin derivatives were successfully synthesized by hydrogenation of limonin, using different reducing agents (sodium cyanoborohydride, lithium aluminum hydride, and sodium borohydride). The chemical structure of the seven derivatives was characterized and identified by a series of techniques, including HR-ESI-MS, 1H-NMR, 13C-NMR, 2D-NMR, and IR. Among the seven limonin derivatives, six limonin derivatives were found to be new compounds which have not been previously reported. Then, the anti-inflammatory activities of the seven synthesized limonin derivatives, as well as the anti-inflammatory activities of eight known natural limonins, were evaluated and compared. Natural limonins, 30-O-Acetylhainangranatumin E and Xylogranatin A, presented significantly better anti-inflammatory activity. Xylogranatin A could inhibit LPS-induced RAW264.7 cell inflammatory factors, with a 90.0% inhibition ratio of TNF-α and 63.77% inhibition ratio of NO release in LPS-induced BV2 cells at 10 μM. Other natural limonins showed poor anti-inflammatory activity. In comparison, all the synthetic limonin derivatives showed decent anti-inflammatory activities, with the highest inhibition ratio of TNF-α of 37.8% and inhibition ratio of NO release of 12.5% in LPS-induced BV2 cells at 10 μM.
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SETHI, A. P. S., M. SINGH, M. WADHWA, M. BAWA, R. WAGH, G. KAUR, K. S. PANNU, and R. S. SETHI. "Impact of kinnow peel and nano-limonin on the performance and meat quality of commercial broilers." Indian Journal of Animal Sciences 90, no. 6 (September 21, 2020): 917–22. http://dx.doi.org/10.56093/ijans.v90i6.105005.
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This study was taken up with the objective to assess the effect of limonin on the performance of commercial broilers and quality of meat. Day old chicks (200) were divided into 8 groups, each group contained 4 replicates of 6 chicks each in equal sex ratio. The iso-nitrogenous and iso-caloric diets were fed for 35 days, i.e. starter, grower and finisher phase. Kinnow peel powder (KPP) and solid lipid nanoparticles (SLN) of kinnow peel powder containing 7.47 mg limonin/g was added in the required quantity of feed to supply 0, 0.5, 1.0 and 1.5 mg limonin/bird/day. The data was analyzed using 2×4 factorial design. The data revealed that the birds fed diet supplemented with SLN consumed more feed in comparison to those fed diet supplemented with KPP, resulting in higher gain in weight, but without affecting feed conversion ratio (FCR). The digestibility of CP was lower and that of CF was higher when diet was supplemented with SLN in comparison to the one supplemented with KPP. As compared to control diet, limonin up to 1% level did not have any adverse effect on the digestibility of nutrients, but it was depressed beyond 1% level of limonin supplementation. The limonin beyond 1% depressed the dressing percentage. It was concluded that nano-formulations @ 1.0 mg/bird/d is an effective carrier of limonins, leading to improved growth, health characteristics in broilers and meat enriched with limonin.
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Fan, Zhang, Luo, Wang, Tang, Chen, and Yu. "Limonin: A Review of Its Pharmacology, Toxicity, and Pharmacokinetics." Molecules 24, no. 20 (October 12, 2019): 3679. http://dx.doi.org/10.3390/molecules24203679.
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Limonin is a natural tetracyclic triterpenoid compound, which widely exists in Euodia rutaecarpa (Juss.) Benth., Phellodendron chinense Schneid., and Coptis chinensis Franch. Its extensive pharmacological effects have attracted considerable attention in recent years. However, there is no systematic review focusing on the pharmacology, toxicity, and pharmacokinetics of limonin. Therefore, this review aimed to provide the latest information on the pharmacology, toxicity, and pharmacokinetics of limonin, exploring the therapeutic potential of this compound and looking for ways to improve efficacy and bioavailability. Limonin has a wide spectrum of pharmacological effects, including anti-cancer, anti-inflammatory and analgesic, anti-bacterial and anti-virus, anti-oxidation, liver protection properties. However, limonin has also been shown to lead to hepatotoxicity, renal toxicity, and genetic damage. Moreover, limonin also has complex impacts on hepatic metabolic enzyme. Pharmacokinetic studies have demonstrated that limonin has poor bioavailability, and the reduction, hydrolysis, and methylation are the main metabolic pathways of limonin. We also found that the position and group of the substituents of limonin are key in affecting pharmacological activity and bioavailability. However, some issues still exist, such as the mechanism of antioxidant activity of limonin not being clear. In addition, there are few studies on the toxicity mechanism of limonin, and the effects of limonin concentration on pharmacological effects and toxicity are not clear, and no researchers have reported any ways in which to reduce the toxicity of limonin. Therefore, future research directions include the mechanism of antioxidant activity of limonin, how the concentration of limonin affects pharmacological effects and toxicity, finding ways to reduce the toxicity of limonin, and structural modification of limonin—one of the key methods necessary to enhance pharmacological activity and bioavailability.
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Kang, Jung-Il, Youn Kyoung Choi, Sang-Chul Han, Hyeon Gyu Kim, Seok Won Hong, Jungeun Kim, Jae Hoon Kim, Jin Won Hyun, Eun-Sook Yoo, and Hee-Kyoung Kang. "Limonin, a Component of Immature Citrus Fruits, Activates Anagen Signaling in Dermal Papilla Cells." Nutrients 14, no. 24 (December 16, 2022): 5358. http://dx.doi.org/10.3390/nu14245358.
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Hair loss remains a significant problem that is difficult to treat; therefore, there is a need to identify safe natural materials that can help patients with hair loss. We evaluated the hair anagen activation effects of limonin, which is abundant in immature citrus fruits. Limonin increased the proliferation of rat dermal papilla cells (rDPC) by changing the levels of cyclin D1 and p27, and increasing the number of BrdU-positive cells. Limonin increased autophagy by decreasing phosphorylated mammalian target of rapamycin levels and increasing the phospho-Raptor, ATG7 and LC3B. Limonin also activated the Wnt/β-catenin pathway by increasing phospho-β-catenin levels. XAV939, a Wnt/β-catenin inhibitor, inhibited these limonin-induced changes, including induced autophagy, BrdU-positive cells, and cell proliferation. Limonin increased the phosphorylated AKT levels in both two-dimensional cultured rDPC and three-dimensional spheroids. Treatment with the PI3K inhibitor wortmannin inhibited limonin-induced proliferation, and disrupted other limonin-mediated changes, including decreased p27, increased BrdU-positive cells, induced autophagy, and increased ATG7 and LC3B levels. Wortmannin also inhibited limonin-induced cyclin D1 and LC3 expression in spheroids. Collectively, these results indicate that limonin can enhance anagen signaling by activating autophagy via targeting the Wnt/β-catenin and/or PI3K/AKT pathways in rDPC, highlighting a candidate nutrient for hair loss treatment.
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Jin, Jie, Xinhuang Lv, Ben Wang, Chenghao Ren, Jingtao Jiang, Hongyu Chen, Ximiao Chen, et al. "Limonin Inhibits IL-1β-Induced Inflammation and Catabolism in Chondrocytes and Ameliorates Osteoarthritis by Activating Nrf2." Oxidative Medicine and Cellular Longevity 2021 (November 9, 2021): 1–15. http://dx.doi.org/10.1155/2021/7292512.
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Osteoarthritis (OA), a degenerative disorder, is considered to be one of the most common forms of arthritis. Limonin (Lim) is extracted from lemons and other citrus fruits. Limonin has been reported to have anti-inflammatory effects, while inflammation is a major cause of OA; thus, we propose that limonin may have a therapeutic effect on OA. In this study, the therapeutic effect of limonin on OA was assessed in chondrocytes in vitro in IL-1β induced OA and in the destabilization of the medial meniscus (DMM) mice in vivo. The Nrf2/HO-1/NF-κB signaling pathway was evaluated to illustrate the working mechanism of limonin on OA in chondrocytes. In this study, it was found that limonin can reduce the level of IL-1β induced proinflammatory cytokines such as INOS, COX-2, PGE2, NO, TNF-α, and IL-6. Limonin can also diminish the biosynthesis of IL-1β-stimulated chondrogenic catabolic enzymes such as MMP13 and ADAMTS5 in chondrocytes. The research on the mechanism study demonstrated that limonin exerts its protective effect on OA through the Nrf2/HO-1/NF-κB signaling pathway. Taken together, the present study shows that limonin may activate the Nrf2/HO-1/NF-κB pathway to alleviate OA, making it a candidate therapeutic agent for OA.
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Takahashi, K., M. Obayashi, and M. Nakatani. "Structure of limonin." Acta Crystallographica Section C Crystal Structure Communications 46, no. 3 (March 15, 1990): 425–27. http://dx.doi.org/10.1107/s0108270189007225.
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Yu*, Jun, Romeo Toledo, Rakesh Singh, Leonard Pike, and Bhimanagouda Patil. "Supercritical Fluid Extraction of Limonoids from Grapefruit Seeds." HortScience 39, no. 4 (July 2004): 806D—806. http://dx.doi.org/10.21273/hortsci.39.4.806d.
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Grapefruit seeds were studied for the extraction of limonoids using supercritical CO2 extraction (SC-CO2) technique. Limonin aglycone was successfully extracted with SC-CO2 directly from grapefruit seeds; and the limonin glycoside was extracted using SC-CO2 and ethanol as co-solvent from the spent seeds after the extraction of limonin aglycone. In an effort to optimize the extraction conditions of limonin aglycone, pressure, temperature, time effects were investigated. Various times of extraction, CO2 flow rate and the feeding modes of CO2 were also employed to obtain the highest yield of limonin aglycone. Optimal conditions to achieve the highest limonin aglycone (0.63 mg/g seeds) were 48.3 MPa, 50°C and 60 min with CO2 bottom feeding, flow rate about 5 L/min. The extraction conditions for limonin glycoside to achieve highest yield were further optimized. The highest extraction yield (0.62 mg limonin glycoside/g seeds) were at 48.3 MPa, 50°C, 30% molar fraction of ethanol (XEth =0.30) and 40 min with CO2 top feeding, flow rate about 5 L/min. The results demonstrated that supercritical CO2 extraction of limonoids from grapefruit seeds, a citrus juice industry byproduct, has practical significance for commercial production.
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Liu, C., J. Liu, Y. Rong, N. Liang, and L. Rong. "Aqueous extraction of limonin from Citrus reticulate Blanco." Czech Journal of Food Sciences 30, No. 4 (June 13, 2012): 364–68. http://dx.doi.org/10.17221/108/2011-cjfs.
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The replacement of organic solutions in the extraction of limonin from citrus seeds with an alkaline solution was investigated. This method was based on the reversible conversion of limonin to limonoate A-ring lactone via ring-opening of D-ring lactone at different pH values. The extraction conditions, optimised using Taguchi experimental design, were as follows: pH 11, temperature 70°C, alkaline solution/seeds ratio 20:1 (v/w), ultrasonic power 800 W for 30 minutes. A yield of 7.5 mg/g (limonin/citrus seeds) of 98% pure limonin was obtained.
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Fernández-Mateos, A., P. Herrero Teijón, G. Pascual Coca, R. Rubio González, and M. S. J. Simmonds. "Synthesis of limonoid CDE fragments related to limonin and nimbinim." Tetrahedron 66, no. 36 (September 2010): 7257–61. http://dx.doi.org/10.1016/j.tet.2010.07.020.
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Zhang, Jun, Zhiqiang Yang, Yan Liang, Linyan Zhang, Wei Ling, Can Guo, Guangling Liang, Guotian Luo, Qin Ye, and Balian Zhong. "Effects of Postharvest Time, Heat Treatment, pH and Filtration on the Limonin Content in Newhall Navel Orange (Citrus sinensis Osbeck cv. Newhall) Juice." Molecules 23, no. 10 (October 19, 2018): 2691. http://dx.doi.org/10.3390/molecules23102691.
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Delayed bitterness causes severe economic loss in citrus juice industry worldwide, which is mostly due to the formation of limonoid compounds, especially limonin, in juice. In this study, effects of postharvest time of fruits, heat treatment, pH and filtration of juice on limonin content in Newhall navel orange (Citrus sinensis Osbeck cv. Newhall) juice were investigated. Our research indicated for the first time that: (1) limonin content in juice would gradually increase to a maximal level and then remained almost constant thereafter as storage time going on, whereas the maximum constant value (MCV) of limonin content in juice significantly (p < 0.05) decreased with the increment of postharvest time of fruits being juiced; (2) heat treatment and acidification of juice only speeded up the formation of limonin to the maximal level while without changing the MCV of limonin content; (3) the juice after filtration exhibited much lower MCV of limonin content compared with the unfiltered one. These experimental observations might not only provide useful information for the development of new debitterness method for navel orange juice, but also strongly support the acid-promoted delayed bitterness mechanism, suggesting the formation of delayed bitterness might primary due to the acid-promoted rather than the enzyme-catalyzed lactonization of limonoate A-ring lactone (LARL) to produce limonin in juice of navel orange.
Dissertations / Theses on the topic "Limonin"
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Rizza, Giorgio. "Citrus Limonoids: Functional Chemicals in Agriculture and Foods." Doctoral thesis, Università di Catania, 2016. http://hdl.handle.net/10761/4026.
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The search for limonoids started long back when scientists started looking for the factor responsible for bitterness in citrus. Studies showed that limonoids are highly oxygenated, modified terpenoids and have recently attracted attention because compounds belonging to this group have exhibited a range of biological activities like insecticidal, insect antifeedant and growth regulating activity on insects as well as antibacterial, antifungal, antimalarial, anticancer, antiviral and a number of other pharmacological activities on humans.
Based on this premise this paper has focused on technological, healthful and chemical aspects of the limonoids.
-TECHNOLOGICAL APPROACH:
Based on a project titled Enhancement of bioactive compounds isolated from agro-industrial wastes financially supported by the Italian Ministry of Education, a Sicilian juice company wanted to assess the possibility of transforming the waste by-product of citrus processing (pastazzo) in a resource trying to turn it into dietary fiber. To do that, the company has inserted a debittering line to the plant using an alkaline aqueous solution in order to extract flavanones and limonoids.
In the present paper the operational conditions of debittering were evaluated and optimized by determining the limonin content of samples from various stages of fiber production; It was also verified if the recovery of limonin extracted was economically viable.
-HEALTHFUL AND ORGANOLEPTIC CHARACTERISTICS:
It has been established that U.S. producers are turning to organic farming system as a potential way to lower input costs, decrease reliance on nonrenewable resources, capture high-value markets at premium price, and boost-farm income. Organic production agriculture is characterized by inputs of biologically (non-synthetic) based fertilizers and pest management practices that are sustainable.
In order to understand if the market source contributes to differences in bioactives content, the bio-actives content of fruits obtained from farmers' markets was compared to the content found in fruit purchased from retail grocery stores. Organoleptic properties, including Brix, TTA, color and pH were measured. Limonin, ascorbic acid and flavanoid contents were also determined.
-SYNTHESIS AND CHARACTERIZATION OF FUNCTIONAL COMPOUNDS:
Ehrlich s reagent, p-dimethylaminobenzaldehyde (DMBA) in hydrochloric acid, has a long history and is known as the coloring reagent of pyrrole. 2,3.
When a solution of limonoids is treated with p-dimethylaminobenzaldehyde in acid environment the solution immediately change to red-purple until dark blue. This reaction has named Ehrlich s reaction and the purple coloring is probably due to the presence of an adduct compound with an electron-rich trisubstituted furan ring.
In order to determine the structure of the limonin-DMBA and limonin glucoside-DMBA adducts, both compounds have been synthesized, purified and characterized. This project involves synthesis of the target compounds. MS analysis were conducted for the characterization of the isolated products.
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Kim, Wooki. "Molecular mechanisms of immunosuppressive effects of dietary n-3 pufa, curcumin and limonin on murine cd4+ t cells." [College Station, Tex. : Texas A&M University, 2008. http://hdl.handle.net/1969.1/ETD-TAMU-3212.
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Willrodt, Christian. "Synthetic biology for synthetic chemistry - Microbial production and selective functionalization of limonene." Doctoral thesis, Universitätsbibliothek Leipzig, 2016. http://nbn-resolving.de/urn:nbn:de:bsz:15-qucosa-201140.
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The progress in biotechnological disciplines such as metabolic engineering or synthetic biology increased the interest of chemical and pharmaceutical industries to implement microbial processes for chemical synthesis. However, most microorganisms, e.g., Escherichia coli or Saccharomyces cerevisiae, used in biotechnological applications are not evolved by nature for the production of industrially relevant compounds, which are often hydrophobic, non-charged, volatile, or toxic to the microbial organisms. Bioprocess design relies on an integrated approach addressing pathway, cellular, reaction, and process engineering to combine the results of natural evolution with the demands of industrial applicability.
In this thesis, the microbial de novo production and selective oxyfunctionalization of the highly volatile isoprenoid limonene has been investigated as a model system featuring reactants with challenging physicochemical characteristics. Key constraints that limit limonene biosynthesis and its oxyfunctionalization in recombinant E. coli, related to genetics, physiology, and reaction engineering, were identified and relieved.
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Graebin, Cedric Stephan. "Síntese e avaliação da atividade farmacológica in vitro de aminas derivadas do limoneno." reponame:Biblioteca Digital de Teses e Dissertações da UFRGS, 2008. http://hdl.handle.net/10183/76986.
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O limoneno é um produto natural da classe dos terpenos, encontrado abundantemente em plantas cítricas e relatado na literatura como um composto com atividades farmacológicas interessantes, entre elas antibacteriana, antifúngica, antileishmania, nociceptiva e citotóxica. A presente tese relata a funcionalização do limoneno utilizando a Síntese Orgânica em Fase Sólida e a Síntese Orgânica Clássica (em solução). A partir da síntese orgânica em solução, especialmente através das reações de hidroformilação e hidroaminometilação, obtiveram-se vinte compostos. Os compostos foram testados para várias atividades farmacológicas in vitro, a saber: antibacteriana, antifúngica, anti-tripanossoma e anti-leishmania. Destes, dezessete foram testados para a atividade anti-leishmania in vitro contra formas promastigotas de L. (V.) braziliensis e sete apresentaram atividade superior ao fármaco pentamidina, utilizado como padrão no teste, com valores de IC50 entre 11,5 e 35,6 μM.Limonene is a natural product from the terpene family, found in great proportions in citrical plants, being reported in the literature as having interesting pharmacological activities, such as antibacterial, antifungical, antileishmanial, nociceptive and citotoxic. This thesis reports the funcionalization of limonene via Solid-Phase Organic Synthesis and classical solution-phase synthesis. Twenty products were obtained from the solution-phase protocols, especially from reactions such as hydroformylation and hydroaminomethylation. The compounds were tested for several pharmacological activities, e.g.: antibacterial, antifungical, anti-tripanossomal and anti-leishmanial. Seventeen of those compounds were tested against in vitro promastigote strains of Leishmania (V.) braziliensis and seven compounds were found to have greater anti-leishmanial activity than pentamidine, the standard drug used in this test, presenting IC50 values ranging from 11,5 to 35,6 μM.
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Fayoux, Stéphane C. "Interactions between plasticised PVC films and citrus juice components." Thesis, View thesis, 2004. http://handle.uws.edu.au:8081/1959.7/35863.
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The study presented here consists in an original piece of work to better understand complex food packaging interactions. The majority of investigations on food polymer interactions related to orange juice and this provided a good base to our study (Literature reviews: cf. Chapters 1a and b). Additionally a rather remarkable finding in 1994 was that limonin, a trace bitter material found in some varieties of orange juice was rapidly absorbed by highly plasticised polyvinyl chloride (PVC plastisol) (Chapter 2). Several commercial absorbants are available for debittering, relying on limonin absorption on the large surface area of the highly porous absorbant pellets. However, the absorptive properties of the smooth plastisols apparently relied on a different mechanism. Limonin is a very large (470.5 g/mol) compound, but some preliminary experiments with another much smaller orange juice constituent d- of absorbates in plastisols, methods used earlier (Moisan 1980, Holland and Santangelo 1988) to measure solubilities and diffusion constants in packaging films could be advantageously used to survey these properties in a wide range of materials, including model compounds of various types, and a number of compounds which may be found in citrus juices (Chapters 3, 4 and 5). Experimentally, the method found most suitable was to use a ‘test film’ of pure
plastisol which was wrapped tightly on both sides by a similar ‘supply film’ blended with 1 Molar test material (also called ‘absorbate’), setting up a concentration gradient. The inner test film was removed at regular intervals (minutes to hours) to measure (mainly by weighing) the uptake of the test reagent with time. Rather unexpectedly, it was found in a number of cases that the test film lost weight, either from the beginning, or after a period of time. Three main types of behaviour were identified: Type A lost weight from the beginning and over a long period of time, Type B gained weight initially and then lost weight, and Type C gained weight until a steady state was reached. Often the maximum, or near maximum, mass increase occurred within around 100 minutes, indicating a very rapid, liquid-like diffusion mechanism, in harmony with the rapid uptake of d-limonene and limonin. The major parameters of interest with these compounds are their diffusion rates and their solubilities, and in the presence of aqueous media (orange juice and other foodstuffs) the partition coefficient between the plastisol and water, which is related to the hydrophobicity function LogP for the compound. The major complicating factor in these measurements is the observation that the plasticiser materials themselves also migrate, in the reverse direction, because of the lower effective concentration in the supply film. This effect tends to be small, but is one explanation for the mass loss observed above, and cannot be ignored over the long
term, nor in its practical applications to contamination in foods. There are many possible applications for the techniques described above. The removal or addition of compounds in food packaging itself is one. Upgrading foods, such as orange juice, commercially, is another. In many cases ‘scalping’ off-flavours or other minor components takes place exclusively through solid or liquid contact with the packaging. The removal from the headspace measured by the current gas permeation methods is irrelevant for the vast numbers of involatile, but easily diffusable compounds. For such compounds these novel applications are simple and rapid, require little specialised equipment, and fill a niche in the armoury of food and packaging chemists.
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Bonon, Anderson de Jesus 1986. "Obtenção de monômeros naturais através da epoxidação de limoneno." [s.n.], 2012. http://repositorio.unicamp.br/jspui/handle/REPOSIP/322678.
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Orientador: Rubens Maciel FilhoDissertação (mestrado) - Universidade Estadual de Campinas, Faculdade de Engenharia Química
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Resumo: Uma das olefinas de fontes renováveis de maior importância no Brasil é o Limoneno, terpeno que compõe cerca de 90% do óleo da casca da laranja. O Brasil é o maior produtor mundial de laranja, com uma produção, entre 2010-2011, de cerca de 15,33 milhões de toneladas do fruto, dos quais 89% da produção são destinadas à produção de suco, sendo a casca e o óleo fixo, resíduos do processo. A parte volátil do óleo é constituída majoritariamente de (R)-limoneno (90 %). Terpenos como o limoneno, podem ser submetidos a reações de oxidação catalítica nos quais os epóxidos são os principais produtos, e podem ser utilizados como precursores para uma ampla variedade de produtos como fármacos, fragrâncias e na fabricação de biopolímeros e resinas. Mediante ao exposto, este trabalho tem por objetivo o estudo da epoxidação de limoneno para a obtenção de epóxidos que possam ser utilizados como monômeros para a síntese de biomateriais para a construção de dispositivos médicos, sendo que avaliou-se sistemas epoxidativos contenho metiltrioxorênio, montmorilonita e alumina. O sistema mais promissor, utilizando H2O2 como oxidante, ?-Al2O3 como catalisador em acetato de etila, foi avaliado em condições reacionais brandas, a 80 °C em pressão atmosférica, caracterizando um sistema verde. As variações na concentração inicial de reagentes a fim de entender o sistema foram estudadas, o que direcionou o estudo para sua otimização via planejamento de experimentos, sendo atingida uma conversão de 100 % em 10 h de reação. A obtenção de limoneno por evaporação de passo curto do óleo de laranja também foi estudada e otimizada, chegando-se à pureza de 99,6 %. O ensaio nas condições ótimas de reação com o limoneno obtido do óleo de laranja mostrou-se idêntico ao limoneno comercial. Os resultados obtidos demonstram a eficácia tanto do processo de obtenção do limoneno, como do sistema reacional com uma produção limpa, uma característica imprescindível para biofabricação
Abstract: One of the most important olefins from a renewable source of in Brazil is limonene. The orange peel oil is about 90% limonene. Brazil is the largest producer of orange in the world wild, with a 2010-2011 production about 15.33 million tons of fruit. About 89% of the fruits are intended for the production of juice, which peel and fixed oil are residue from the process. The volatile oil portion is composed predominantly of (R)-limonene. Terpenes such as limonene, may be subjected to catalytic oxidation reactions where the epoxides are the main products, and can be used as precursors for a wide variety of products such as pharmaceuticals, fragrances and the manufacture of biopolymers and resins. By the above, this work is dedicated to study the epoxidation of limonene in order to obtaining epoxides that may be used as monomers for the synthesis of biomaterials with chemical quality to medical devices manufacturing. Thus, some systems like methyltrioxorhenium, montmorillonite and alumina were tested. The most promissory system, using H2O2 as oxidant, ?-Al2O3 as catalyst and ethyl acetate as solvent, was evaluated in mild reaction conditions, at 80 °C at atmospheric pressure, featuring a green system. It was carried out the initial concentration of the substrate, oxidant and catalyst variation studies in order to understand the system, which directed for the optimization by experimental design. It was achieved a 100% of conversion in 10 hours of reaction. It was also studied the limonene purification by short path evaporation of the orange oil. It was achieved a limonene with 99.6 % of purity. The optimum reaction conditions were performed with limonene obtained from orange oil, the comparative result showed and an identical behavior between the commercial and the distillated limonene. These results demonstrate the effectiveness of both the process, the limonene obtainment and the reaction system with a clean and no toxic production, an essential feature for biofabrication
Mestrado
Desenvolvimento de Processos Químicos
Mestre em Engenharia Química
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Wanderley, Kristine Bruce. "Recuperação de magnésio do licor de lixiviação de minério limonítico por cristalização." Universidade de São Paulo, 2018. http://www.teses.usp.br/teses/disponiveis/3/3137/tde-23052018-084841/.
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No processo de obtenção de níquel de fontes de minério limonita, a lixiviação ácida do minério resulta na dissolução de íons metálicos em uma solução aquosa. Com o uso da tecnologia apropriada, é possível recuperar esses íons metálicos em vez de descartá-los. O presente estudo tem como objetivo a recuperação de magnésio de uma solução contendo íons magnésio e sulfato utilizando-se a técnica da cristalização a alta temperatura. A aplicação da cristalização a alta temperatura para recuperar o magnésio na forma de sulfato de magnésio hidratado pode ser vantajosa uma vez que sua decomposição térmica resulta em MgO e SO2, produtos que podem ser reutilizados no processo de mineração da limonita. Isso reduz o volume de resíduo formado e custo de reagentes no processo. Foi projetado um sistema de cristalizador acoplado a filtração e foi verificado a influência da temperatura, tempo de residência e pH da solução na quantidade de magnésio cristalizado. A solução residual de cada batelada foi analisada por cromatografia de íons para quantificar o magnésio na solução. Os cristais formados foram analisados utilizando-se a técnica de difração de raios-X (DRX), por microscopia eletrônica de varredura (MEV-EDS) e agitamento de peneiras a fim de avaliar a composição química, morfologia e granulometria dos cristais. A solubilidade do sulfato de magnésio foi determinada experimentalmente com o intuito de ampliar a compreensão da solubilidade do sal e obter valores de Kps. Em 5 horas de tempo de residência o sistema foi estabilizado, indicando que não haverá mais crescimento cristalino em tempos de residência maiores que 5 horas. Em pH 5,7 a 230°C e em 5 horas de tempo de residência ocorreu a maior remoção de magnésio com cerca de 81% cristalizado. Os cristais apresentaram morfologia esférica com exceção do cristal obtido a 230 °C em pH 2, que apresentou formato retangular. A análise por DRX mostrou a presença de um produto constituído majoritariamente por sulfato de magnésio monohidratado.In the process of obtaining nickel from sources of limonite ore, the acid leaching of the ore results in the dissolution of metallic ions in solution. With the use of appropriate technology, it is possible to recover these metal ions instead of discarding them. The present study aims to recover magnesium from a solution containing magnesium and sulfate ions using high temperature crystallization. The application of high temperature crystallization to recover magnesium in the form of hydrated magnesium sulfate may be advantageous since its thermal decomposition results in MgO and SO2, products which can be reused in the limonite mining process. This reduces the volume of waste formed and the cost of reagents in the process. A crystallizer coupled to a filtration system was designed and the influence of the temperature, residence time and pH of the solution on the amount of crystallized magnesium from solution was investigated. The residual solution was analyzed by ion chromatography to quantify the magnesium in the solution. The crystals formed were analyzed by X-ray diffraction (XRD), Scanning Electron Microscopy (SEM-EDS) and sieve shakers in order to evaluate the chemical composition, morphology and grain size of the crystals. The solubility of magnesium sulphate was determined experimentally to increase the understanding of the solubility of the salt and obtain values of Kps. In 5 hours of residence time the system was stabilized, indicating that there will be no more crystalline growth at residence times greater than 5 hours. At pH 5.7 at 230 ° C and in 5 hours of residence time 81% of Mg crystallized. The crystals presented spherical morphology except for crystals obtained at 230 °C, at pH 2, which presented a rectangular shape. XRD analysis showed the presence of a product consisting mainly of magnesium sulphate monohydrate.
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Bicas, Juliano Lemos 1982. "Estudos de obtenção de bioaromas pela biotransformação de compostos terpenicos." [s.n.], 2009. http://repositorio.unicamp.br/jspui/handle/REPOSIP/256672.
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Orientador: Glaucia Maria PastoreTese (doutorado) - Universidade Estadual de Campinas, Faculdade de Engenharia de Alimentos
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Resumo: O objetivo do presente trabalho foi efetuar estudos de biotransformação de substratos terpênicos para a obtenção de compostos de aromas naturais, ou bioaromas, enfatizando os processos bioquímicos envolvidos nos procedimentos empregados e a otimização da produção para possíveis aplicações industriais. Assim, o estudo se iniciou com o isolamento de quase 300 linhagens, das quais 121 mostraram-se resistentes a concentrações de 2% de R-(+)-limoneno e 70 foram capazes de utilizar este substrato como única fonte de carbono. Dentre todas as linhagens potencialmente degradantes do R-(+)-limoneno, nenhuma mostrou acúmulo significativo de metabólito de interesse em concentrações que justificassem estudos de otimização. A seguir, o método de Superfície de Resposta foi empregado para otimizar os principais parâmetros do processo de produção de R-(+)-a-terpineol a partir do R-(+)-limoneno pelo fungo Fusarium oxysporum 152b. Dentre os 10 parâmetros analisados (concentração de glicose, peptona, extrato de malte e de levedura no meio de biotransformação; concentração de R-(+)- limoneno; concentração de biosurfactantes; temperatura; agitação; pH; tamanho do inóculo), três (concentração de substrato, temperatura e agitação) influenciaram significativamente (p < 0,10) a produção de R-(+)-a-terpineol, dentro das faixas estudadas. A otimização dessas variáveis por um Delineamento Composto Central Rotacional revelou que as condições ótimas para a biotransformação foram de 0,5% de R-(+)-limoneno, 26 °C e 240 rpm, resultando em uma concentração de cerca de 2,4 g.L-1 de R-(+)-a-terpineol ao final de 72 h de processo. Aproveitando-se do fato de essa linhagem fúngica ser reconhecida pela produção de lípase alcalina, um sistema integrado de produção foi posteriormente proposto a fim de explorar todo potencial biotecnológico do microrganismo. Assim, a biomassa resultante da produção de lipase, antes descartada, foi avaliada quanto à preservação da atividade de biotransformar o R-(+)- limoneno. Os resultados demonstraram ser possível a coprodução de lipase/R-(+)-a-terpineol, apesar de que o rendimento máximo do bioaroma foi cerca de 50% inferior quando comparado ao do procedimento convencional. Os estudos com duas linhagens bacterianas (Pseudomonas rhodesiae CIP 107491 e P. fluorescens NCIMB 11671) para a bioconversão de alguns monoterpenos indicaram a presença de uma via metabólica envolvendo ß-pineno, a-pineno, a-pineno oxido, isonovalal e ácido dimetil pentanóico para ambas espécies, além de outras duas vias de degradação do limoneno para P. fluorescens. Nesse caso, a bactéria usava o limoneno como única fonte de carbono e energia, passando por limoneno-1,2-diol, e também hidroxilava este substrato na posição 8 formando R-(+)-a-terpineol como forma de diminuir a toxicidade do substrato (metabolismo de xenobióticos). Essa última via ocorria em ausência de cofatores graças à ação de uma hidratase enantioespecífica capaz de converter anaerobicamente R-(+)-limoneno a R-(+)-a-terpineol e S-(¿)-limoneno a S-(¿)-a-terpineol em meios bifásicos, empregando n-hexadecano como fase orgânica. Foi posteriormente demonstrado que os rendimentos e produtividade poderiam ser significativamente elevados e que a produção poderia ser mais que duplicada (de ~10 para ~25 g.L-1) com o uso de fases orgânicas não convencionais, como óleos vegetais. Finalmente, estudos preliminares de avaliação do potencial bioativo do principal produto relatado nessa tese demonstraram que o a-terpineol revelou uma elevada capacidade de absorção de radical de oxigênio (ORAC) e atividade antiploriferativa contra cinco linhagens de células cancerosas, apesar da baixa atividade de captura de radical DPPH. Esses resultados abrem precedentes para que pesquisas in vivo sejam consideradas a fim de determinar o potencial funcional desse bioaroma, algo ainda praticamente inexplorado
Abstract: The objective of the present work was to study the biotransformation of terpene substrates to obtain natural flavor compounds (bioflavors), focusing the biochemical processes involved in the procedures investigated and optimization of production for possible industrial applications. Therefore, the study started with the isolation of more than 300 wild strains followed by the selection of 121 capable of resisting to 2% (v.v-1) of R-(+)-limonene and 70 that could use this terpene as sole carbon and energy source. None of the strains tested showed accumulation of intermediate metabolites in levels that justified further optimization studies. Subsequently, the Response Surface Methodology was employed to optimize the main parameters of the process of biotransformation of R-(+)-limonene to R-(+)-a-terpineol by the fungal strain Fusarium oxysporum 152b. Only three (R-(+)-limonene concentration, temperature and agitation) of the ten parameters tested (concentration of glucose, peptone, malt extract and yeast extract; substrate concentration; biosurfactant concentration; temperature; agitation; pH; inoculum size) influenced significantly (p < 0.1) the R-(+)-a-terpineol production. The optimization of these variables applying a Central Composite Design revealed that the optimal biotrasformation conditions were 0.5% of R-(+)-limonene, 26 °C and 240 rpm, resulting in a R- (+)-a-terpineol concentration close to 2,4 g.L-1 after a 72 h. Since this fungus has been recognized for its high alkaline lipase production, an integrated process was proposed to explore the full biotechnological potential of this microorganism. Therefore, the biomass resulting from the lipase production, which was previously discharded, was tested to evaluate the preservation of R-(+)-limonene-biotransformation activity. The results have shown that the co-production of lipase/R-(+)-a-terpineol was feasible, although the maximal yield of the bioflavor was approximately 50 % lower when compared to the conventional process. The studies with two pseudomonad strains (Pseudomonas rhodesiae CIP 107491 e P. fluorescens NCIMB 11671) for the conversion of some monoterpenes indicated the presence of one metabolic route involving ß-pinene a-pinene a-pinene oxide, isonovalal and dimethyl pentanoic acid for both species, besides two other pathways for the degradation of limonene by P. fluorescens. In this case, the bacterium used the substrate as sole carbon and energy source, with limonene-1,2-diol as intermediate, and also hydroxylated limonene in the position 8 to R-(+)-a- terpineol as a detoxifying strategy (xenobiotic metabolism). The last pathway occurred in the absence of cofactors due to the action of an enantiospecific hydratase capable of converting anaerobically R-(+)-limonene to R-(+)-a-terpineol and S-(¿)-limonene to S-(¿)-a-terpineol in biphasic mediums, employing n-hexadecane as organic phase. It was later demonstrated that the yields and productivities could be significantly enhanced and that the final concentration of the product could be more than duplicated (from ~10 to ~25 g.L-1) if unconventional organic phases (vegetable oils) were used. Finally, preliminary studies evaluating the bioactive potential of the main product reported in this thesis have revealed that the a-terpineol demonstrated an oxygen radical absorbance capacity (ORAC) and an antiproliferative activity against five cancer lines, although the DPPH radical scavenging activity was low. These results encourages in vivo research to determine the functional potential of this bioflavor, something practically unexplored
Doutorado
Doutor em Ciência de Alimentos
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Zhang, Yujie. "Copolymerization of Limonene." Thesis, Université d'Ottawa / University of Ottawa, 2014. http://hdl.handle.net/10393/31221.
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In this thesis, we explored the use of a renewable resource to produce more sustainable polymeric materials. Limonene, a monocyclic terpene existing in many essential oils extracted from citrus rinds, was the renewable monomer investigated. The d-limonene ((+)-limonene) isomer is a major component (~90%) of orange oils from orange juicing and peel processing. Having been used as a flavour and fragrance additive in cosmetics, foods and beverages, as well as a green solvent, limonene is of particular interest in polymerization, because it contains double bonds, which provide the bifunctionality necessary for polymerization. Limonene is also an allylic monomer (CH2=CH-CH2Y), which presents challenges in free-radical homopolymerization and thus, copolymerization was investigated herein to overcome this difficulty.
2-Ethylhexyl acrylate (EHA) and n-butyl methacrylate (BMA) were used in two separate projects, as comonomers with limonene. Using bulk free-radical copolymerization at 80℃, with benzoyl peroxide (BPO) as the initiator, high molecular weight (>100,000) EHA/limonene and BMA/limonene copolymers were produced. Reactivity ratios, important parameters used in the prediction of copolymer composition, were estimated and shown to accurately predict the copolymer composition of subsequent experiments. These can now be used for the application of appropriate semi-batch policies to further enhance limonene incorporation into the copolymers.
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Charbonneau, Luc. "Époxydation du limonène." Doctoral thesis, Université Laval, 2018. http://hdl.handle.net/20.500.11794/33260.
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Le limonène a été souligné comme molécule clé pour le développement de polymères biosourcés comme alternative aux monomères classiques provenant de sources pétrolières, mais la polymérisation directe de celui-ci conduit à des plastiques de basse qualité. Cependant, ses produits d’époxydation tels que le 1,2-oxyde de limonène et le dioxyde de limonène sont essentiels pour la production de polycarbonates verts et de polyuréthanes sans l’utilisation d’isocyanate et par conséquent la production de ces deux molécules devient un enjeu majeur. Tout d’abord, l’époxydation du limonène a été effectuée en présence d’un catalyseur au titane de basse coordination supporté sur une silice mésoporeuse de type SBA-16 en présence de TBHP dans le décane comme agent oxydant. La conversion en limonène a été de 80% avec une sélectivité en 1,2-oxyde de limonène de 79% ainsi que de 21% en 8,9-oxyde de limonène après 24 h de temps de réaction. Les conditions réactionnelles ont été optimisées et la réaction doit être effectuée en présence de 300 mg du catalyseur à 75oC dans l’acétonitrile comme solvant avec un rapport molaire TBHP/limonène de 11/6,2. Toutefois, l’utilisation d’un catalyseur au titane supporté sur une silice mésoporeuse s'est avérée inefficace pour la double époxydation du limonène en dioxyde de limonène. Différentes alternatives ont été considérées afin de produire cette molécule. Une approche relativement verte consiste à effectuer la double époxyadtion dans des conditions semi-continues en employant le DMDO généré in situ par la réaction de l’acétone avec une solution aqueuse d’Oxone® à température ambiante. Deux méthodes ont été étudiées et comparées. Tout d’abord la réaction a été effectuée dans un système biphasique conventionnel eau-solvant organique à température ambiante. L’acétate d’éthyle a été employé comme phase organique dans cette étude. La conversion obtenue dans ces conditions a été de 95% avec un rendement de 33% pour le dioxyde de limonène. Lorsque cette même réaction a été effectuée en excès d’acétone, la conversion obtenue a été de 100% et un rendement de 97% en dioxyde de limonène en seulement 1,5h. Les conditions de la réaction ont été optimisées. La réaction doit être effectuée avec un débit de solution aqueuse d’Oxone® de 4 mL min-1 et un excès stoechiométrique de 33% avec un temps de réaction de 45 min à température ambiante. Le caractère multiphasique de la réaction d’époxydation du limonène entraîne des limitations du transfert de matière du DMDO de la phase aqueuse à la phase acétone. Pour pallier ce problème, les ultrasons ont été employés afin d’accélérer ce processus de transfert de matière et réduire le temps de la réaction. La double époxydation du limonène en présence d’ultrasons avec une puissance nominale de 50W a permis d’obtenir un rendement de 100% en dioxyde de limonène avec un temps de réaction de seulement 4,5 min à température ambiante. À partir de ces résultats, d’autres terpènes ont aussi été époxydés afin de généraliser la technique. Les deux isomères du pinène ont été convertis à 100% en leur époxyde respectif en seulement 4 min. Le farnésol, un tri-alcène, a lui été converti à 100% en tri-époxyde de farnésol en 8 min. Le carvéol, un dérivé du limonène a été converti à 100% après 5 min de temps de réaction. Le rendement en diépoxyde était supérieur à 95%. Les sous-produits de la réaction consistaient aux deux monoépoxydes du carvéol et la présence de carvone a aussi été détectée. Le carvone, un autre dérivé du limonène a lui aussi été converti à 100% après 5 min de temps de réaction, seulement le 7,8-époxyde carvone, un monoépoxyde, a été produitLimonene has been highlighted as a key molecule for the development of bio-based polymers as an alternative to conventional monomers from petroleum sources, but the direct polymerization of this leads to low quality plastics. However, its epoxidation products such as 1,2-limonene oxide and limonene dioxide are essential to produce green polycarbonates and polyurethanes without the use of isocyanate, therefore the production of these two molecules becomes a major issue. First, the epoxidation of limonene was carried out using low coordination titanium catalyst supported on a SBA-16 mesoporous silica in the presence of TBHP in the decane as oxidizing agent. The conversion to limonene was 80% with a selectivity of 79% 1,2-oxide of limonene and 21% of 8,9-limonene oxide after 24 hours of reaction time. The reaction conditions were optimized, and the reaction should be carried out in the presence of 300 mg of the catalyst at 75 ° C in acetonitrile as solvent with a molar ratio TBHP / limonene of 11 / 6.2. However, the use of a titanium catalyst supported on a mesoporous silica has proved ineffective for the double epoxidation of limonene to limonene dioxide. Different alternatives have been considered in order to produce this molecule. A relatively green approach is to perform the double epoxydation under semi-continuous conditions using DMDO generated in situ by the reaction of acetone with an aqueous solution of Oxone® at room temperature. Two methods have been studied and compared. First, the reaction was carried out in a conventional biphasic water-organic solvent system phase at room temperature. Ethyl acetate was used as the organic phase. The conversion obtained under these conditions was 95% with a yield of 33% for limonene dioxide. When the same reaction was carried out in excess of acetone, the obtained conversion of limonene was 100% leading to 97% of limonene dioxide in only 1.5 hours. The conditions of the reaction have been optimized. The reaction must be carried out with a flow rate of Oxone® aqueous solution of 4 mL min-1 and a stoichiometric excess of 33% with a reaction time of 45 min at room temperature. On the other hand, the multiphasic nature of this reaction causes limitations in the mass transfer of DMDO from the aqueous phase to the acetone phase. Ultrasound has been used to accelerate the mass transfer. process of DMDO and thereby reduce the reaction time. The double epoxidation of limonene in the presence of ultrasound with a nominal power of 50W achieved a yield of 100% of limonene dioxide with a reaction time of only 4.5 min at room temperature. From these results, other terpenes have also been epoxidized to generalize the technique. Both isomers of pinene were converted to 100% in their respective epoxide in just 4 min. Farnesol, a tri-alkene, has been converted to 100% farnesol tri-epoxide in 8 min. Carveol, a derivative of limonene was converted to 100% after 5 min of reaction time. The diepoxide yield was higher than 95%. The by-products of the reaction consisted of both carveol monoepoxide and the presence of carvone was also detected. Carvone, another derivative of limonene, was also converted to 100% after 5 min of reaction time. Only 7,8-epoxide carvone, a monoepoxide, was produced.
Books on the topic "Limonin"
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Limoniana, ili Neizvestnyĭ Limonov. Moskva: Zebra E, 2012.
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Kekeliże, Besik. Limoni: Krebuli. Tʻbilisi: Gamomcʻemloba "Pvoriti", 2001.
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Ḥol ṿe-limonim. Tel Aviv: ʻAm ʻoved, 2006.
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Marín, Mario Arango. Limonium. Bogotá, Colombia: Ediciones Hortitecnia Ltda, 2001.
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Balabanian, Olivier. Limousin. Paris: Bonneton, 2000.
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Carrère, Emmanuel. Limonov. Paris: P.O.L., 2011.
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Sof ʻonat ha-limonim. Yerushalayim: Keter, 2007.
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Limousin cattle in the United Kingdom. East Molesey: Keystock Associates, 1986.
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Zagrebelʹnyĭ, M. P. Ėduard Limonov. Kharʹkov: Folio, 2010.
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(Firm), Pneu Michelin. Berry, Limousin. Paris: Pneu Michelin, 1987.
Find full textBook chapters on the topic "Limonin"
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Schomburg, Dietmar, and Margit Salzmann. "Limonin-D-ring-lactonase." In Enzyme Handbook 3, 155–57. Berlin, Heidelberg: Springer Berlin Heidelberg, 1991. http://dx.doi.org/10.1007/978-3-642-76463-9_32.
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Hasegawa, Shin. "Limonin Bitterness in Citrus Juices." In Flavor Chemistry, 89–106. Boston, MA: Springer US, 1999. http://dx.doi.org/10.1007/978-1-4615-4693-1_9.
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Hasegaw, S., C. Suhayda, M. Omura, and M. Berhow. "Creation of Transgenic Citrus Free from Limonin Bitterness." In ACS Symposium Series, 79–87. Washington, DC: American Chemical Society, 1996. http://dx.doi.org/10.1021/bk-1996-0637.ch007.
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Lam, Luke K. T., Shin Hasegawa, Carl Bergstrom, Sylvia H. Lam, and Patrick Kenney. "Limonin and Nomilin Inhibitory Effects on Chemical-Induced Tumorigenesis." In ACS Symposium Series, 185–200. Washington, DC: American Chemical Society, 2000. http://dx.doi.org/10.1021/bk-2000-0758.ch014.
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Azimova, Shakhnoza S., and Anna I. Glushenkova. "Citrus limonum Burm. (C. limonia Osbeck.)." In Lipids, Lipophilic Components and Essential Oils from Plant Sources, 805. London: Springer London, 2012. http://dx.doi.org/10.1007/978-0-85729-323-7_2633.
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Mansell, R. L., and C. A. McIntosh. "Citrus spp.: In Vitro Culture and the Production of Naringin and Limonin." In Biotechnology in Agriculture and Forestry, 193–210. Berlin, Heidelberg: Springer Berlin Heidelberg, 1991. http://dx.doi.org/10.1007/978-3-642-84071-5_12.
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Bährle-Rapp, Marina. "Limonen." In Springer Lexikon Kosmetik und Körperpflege, 322. Berlin, Heidelberg: Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/978-3-540-71095-0_6015.
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Lim, T. K. "Limonia acidissima." In Edible Medicinal And Non-Medicinal Plants, 884–89. Dordrecht: Springer Netherlands, 2012. http://dx.doi.org/10.1007/978-94-007-4053-2_101.
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Widmer, W. W., and C. A. Haun. "Analysis of Limonin and Flavonoids in Citrus Juices and Byproduct Extracts by Direct Injection and In-Line Sample Clean-Up." In ACS Symposium Series, 60–72. Washington, DC: American Chemical Society, 2000. http://dx.doi.org/10.1021/bk-2000-0758.ch005.
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McIntosh, C. A. "Quantification of Limonin and Limonoate A-Ring Monolactone During Growth and Development of Citrus Fruit and Vegetative Tissues by Radioimmunoassay." In ACS Symposium Series, 73–95. Washington, DC: American Chemical Society, 2000. http://dx.doi.org/10.1021/bk-2000-0758.ch006.
Full textConference papers on the topic "Limonin"
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Agisimanto, Dita, Farida Yulianti, and Hidayatul Arisah. "Cells density affects cell production of Citrus limonia in flask and air-lift bioreactor cultures and limonin farming." In THE SECOND INTERNATIONAL CONFERENCE ON GENETIC RESOURCES AND BIOTECHNOLOGY: Harnessing Technology for Conservation and Sustainable Use of Genetic Resources for Food and Agriculture. AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0075651.
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Ghanem, Fred. "Juice Debittering: Basic Science, Optimization, and Recent Advances." In ASME 2012 Citrus Engineering Conference. American Society of Mechanical Engineers, 2012. http://dx.doi.org/10.1115/cec2012-5701.
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Bitterness such as Naringin in Grapefruits and Limonin in all Citrus fruits have a strong influence on consumers’ choices for their favorite juices. There have been many methods from ultrafiltration to biocatalysis used to lower such bitter compounds and make the juices more desirable by the consumer. One major tool for such debittering operation is the use of synthetic adsorbents which will be discussed in this paper. Ion exchange resins and adsorbents have been used for over a century in various food applications to concentrate flavors, decolorize juices, and enhance the quality of the final product. These types of resins are being synthesized to specific parameters to distinguish them from other tools. Mitsubishi Chemical’s work on optimizing their synthetic adsorbents for high bitterness removal from citrus juice was investigated. Parameters such as the base matrix structure, pore size and distribution, as well as the effect of surface area were studied. As the FDA has strict definitions about the appropriate resin chemistry that can be used in a food application (21 CFR 173.65), progress in new resin chemistry was limited by such regulations. This paper discusses the use of the original Sepabeads SP70 which was introduced into the market about 20 years ago, to the high capacity resin, Sepabeads SP700, which was introduced 10 years ago, and finally, to the Sepabeads SP710, which is the current optimized version of 20 years of research work. Mitsubishi Chemical’s resins were compared to other resins in the industry for the removal of naringin, limonin, and 8-hydroxyfuranocoumarin (furanocoumarins are compounds that affects the proper absorption of certain medications). Proper regeneration and rejuvenation of these resins were outlined. Paper published with permission.
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OSSEIRAN, Noureddin, Therese Huet, Manuel Goubet, Pascal Dréan, and Annunziata Savoia. "MICROWAVE SPECTROSCOPY STUDY SUPPORTED BY QUANTUM CHEMISTRY CALCULATIONS OF LIMONA KETONE, A KEY OXIDATION PRODUCT OF LIMONENE." In 2021 International Symposium on Molecular Spectroscopy. Urbana, Illinois: University of Illinois at Urbana-Champaign, 2021. http://dx.doi.org/10.15278/isms.2021.re07.
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Odio, Carlos. "d-Limonene Recovery." In ASME 1996 Citrus Engineering Conference. American Society of Mechanical Engineers, 1996. http://dx.doi.org/10.1115/cec1996-4204.
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Oils have become an increasingly important by-product of the citrus processing industry. At the high prices reached last year and with good rates of recovery, one could get a dollar’s worth of oil out of a box of Valencia oranges, as shown in Table 1. No other commercially produced by-product of citrus processing comes close to these figures. Paper published with permission.
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McBride, Joseph J. "Limonene: A Versatile Chemical." In ASME 1990 Citrus Engineering Conference. American Society of Mechanical Engineers, 1990. http://dx.doi.org/10.1115/cec1990-3605.
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Following a brief review of the chemistry and properties of limonene as a chemical entity, d-limonene recovered as a by-product in the processing of citrus fruit is discussed in more detail. The largest use of d-limonene, the production of tackifying resins for the adhesive industry, is given special attention, although other important uses, such as in the synthesis of I-carvone, and in specialty solvents and cleaners are also discussed. d-Limonene’s price history is compared with those of its competitors in the resin market, piperylene and sulfate turpentine. Its current relative position in the large and growing market is explained and estimates of its future availability and potential use in the market are proposed. Paper published with permission.
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Mathews, Tanya Ann, Jairo Cortes, and Berna Hascakir. "Evaluation of Environmentally Friendly Green Solvents for the Recovery of Heavy Oils." In SPE Improved Oil Recovery Conference. SPE, 2022. http://dx.doi.org/10.2118/209433-ms.
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Abstract Solvent injection recovery processes were introduced as a more energy-efficient and environmentally friendly alternative to Steam injection processes. However, BTX chemicals (Benzene, Toluene, and Xylene), commonly used for crude oil recovery due to their strong solvency and low asphaltene precipitation, are acutely toxic and harmful to the environment. These chemicals are easily soluble in water causing groundwater contamination. This paper evaluates the recovery efficiency of two green solvents, Limonene, and beta-pinene, on two samples of Californian heavy oil (C1 has an 874.8 cP viscosity and C2 has 178500 cP viscosity). On both C1 and C2, 5 core flood experiments were conducted, in total 10 experiments were run. CO2, limonene, and Beta-pinene were tested as solvents on both oils. Limonene and beta-pinene were both chosen due to their ready availability in the State of California. Both these solvents are plant-derived, non-toxic, and biodegradable. They also have much higher flash points than BTX solvents allowing for safer handling. They have been either injected as sole solvents or co-injected with CO2 during the experiments. Limonene and beta-pinene were injected at 2 mL/min while CO2 was injected at 2000 ml/min with a back pressure of 45-55 psi. Core packs were prepared by filling the pore space of Ottawa sand with 60% PV oil samples and 40% PV water by volume. Produced oil and water samples were collected every 20 min during the experiments. Thermogravimetric analyses (TGA/DSC) were conducted on these samples to identify oil, water, and solvent percentages. Because CO2 is insoluble in these types of high viscosity crude oils, CO2 flooding resulted in immiscibility with almost no oil production. Since both limonene and beta-pinene are aromatic solvents, by sole limonene or beta-pinene injection miscible flooding was achieved. Limonene achieved 35 and 23 vol. % oil recovery from a total of 60% oil for C1 and C2 respectively while Pinene achieved 31 and 27 vol. %. Co-injections of green solvents with CO2 are expected to yield higher recovery due to the presence of two active drive mechanisms namely miscible and immiscible. Co-injection of limonene and CO2 provided the greatest recovery with 45 vol. %, however, recovery efficiencies of pinene and CO2 had comparable recoveries with that of pinene possibly due to phase trapping. Produced samples analysis showed that oil percentages in produced samples were higher for Limonene than Pinene. Our results indicated that limonene and beta-pinene are very promising solvents for heavy oil recovery. Because these solvents are citrus-based, they are both easy to handle and non-toxic. Hence, we believe that our study can be a breakthrough for many heavy oil and bitumen reservoirs all around the world.
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Julie Anne R, BACAYO, EVIO Esteven G, PELAYO David Manfred S, Deang Michael Sean P, and Tumolva Terence P. "Dissolution Kinetics of Low-Density Polyethylene in D-Limonene/Xylene Solutions for the Chemical Recycling of Waste Plastic Laminates." In 7th GoGreen Summit 2021. Technoarete, 2021. http://dx.doi.org/10.36647/978-93-92106-02-6.11.
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The dissolution-precipitation method has been identified as a potentially viable solution to plastic waste recycling in the Philippines. In this study, the effect of solvent temperature and composition on the dissolution kinetics of low-density polyethylene (LDPE) in D-limonene/xylene were determined. Dissolution temperature was varied within 100°-120°C with solvent composition of 0-100 wt% D-limonene for both 2-layer and 3-layer laminates of LDPE and polyethylene terephthalate (PET). The data were fitted to the Korsmeyer-Peppas model and the kinetic parameters were determined. Based on the experimental data, it was observed that there is no definitive relation between the dissolution rate and temperature for all solvent composition except at pure xylene, where the behavior at 110°C and 120°C appeared to be identical. It was also observed that introducing even a small amount of D-limonene to the solvent solution significantly increases the rate of dissolution, with a 1:3 limonene-to-xylene ratio having a K value that is 0.075 higher than that of pure xylene. Dissolution in D-limonene was observed to best fit the Fickian model, while that in xylene generally followed the non-Fickian model. Lastly, the 2-layer laminates showed to follow anomalous transport, wherein solvent diffusion and disentanglement of chains have comparable rates.
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Aloisa, K., and J. Kenny. "399. An Analytical Method for Limonene." In AIHce 1996 - Health Care Industries Papers. AIHA, 1999. http://dx.doi.org/10.3320/1.2765078.
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Mathews, Tanya Ann, Paul Azzu, Jairo Cortes, and Berna Hascakir. "Effective Extraction of a Heavy Oil Resource by an Environmentally Friendly Green Solvent: Limonene." In SPE Annual Technical Conference and Exhibition. SPE, 2022. http://dx.doi.org/10.2118/210138-ms.
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Abstract Global oil consumption is predicted to increase by 15% from 2021 to 2050. The increasing oil demand and decreasing conventional oil supply force us to find alternate energy supplies. The key to this problem lies with the vast untapped heavy oil and bitumen resources. In this study, we investigate the effectiveness of an environmentally friendly solvent, limonene, in recovering heavy oil. Three core flood experiments representing three different recovery methods were carried out. These include steam flooding (E1), solvent flooding (E2), and solvent-steam co-injections (E3). The green solvent, limonene, is a citrus-based non-toxic solvent. It was chosen due to its high organic solvency and ready availability. Throughout the experiments, steam was injected at a cold water equivalent of 18 ml/min, while limonene was injected at 2 ml/min. The experiments were run with a back pressure of 45-55 psi. The core pack was prepared by filling the pore space of Ottawa sand with a 60% heavy oil sample and 40% water by volume (including water percentage in oil). Produced oil and water samples were collected every 20 min during the experiments. These samples were further analyzed by emulsion characterization to determine emulsion stability and oil quality. Spent rock analyses were done to calculate the displacement efficiency of each of the experiments. In addition, an economic analysis was done to determine the optimal recovery method. Spent rock analysis showed that a sole injection of limonene (E2) had the highest oil recovery. This confirms the high organic solvency of limonene achieved miscible flooding producing about 46 vol % from a total of 60 vol % initial oil. Steam flooding (E1), on the other hand, did not perform as well, producing around 29 vol %. The post-mortem sample from E1 indicated asphaltene precipitation which could have lowered oil recovery. Co-injection of limonene and steam was expected to yield the highest recovery due to the presence of two active drive mechanisms, thermal and miscible flooding. However, it performed comparatively less (41 vol %) than a sole injection of limonene (E2). This is further explained with emulsion characterization results. Experiments involving steam (E1 and E2) revealed strong emulsions in the oil produced, indicating a lower quality. Furthermore, it was seen that the solvent-steam process produced weaker emulsions compared to steam flooding alone. On the other hand, solvent flooding (E2) produced high-quality oil with little to no emulsions. These results along with the economic analysis, indicate that the optimal recovery method would be solvent flooding (E2). Our results prove that limonene is a promising organic solvent. Limonene is non-toxic, readily available, and safe to handle. As a result, it can be a safe green alternative to commonly used toxic organic solvents such as toluene.
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Widmer, Wilbur, Weiyang Zhou, and Karel Grohmann. "Converting Citrus Waste to Ethanol and Other Co-Products." In ASME 2009 Citrus Engineering Conference. American Society of Mechanical Engineers, 2009. http://dx.doi.org/10.1115/cec2009-5502.
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Conversion of citrus processing waste (CPW) generated during juice production into value added co-products is an important aspect of the juice industry as it offers a solution to waste disposal issues. Currently the practice of drying citrus waste to produce citrus pulp pellets (CPP) for use as cattle feed is profitable. However, until the recent rise in value, CPP value was marginal and often did not meet production costs. Another concern has been volatile organic emissions during CPP production. Only one third of the residual peel oil present in citrus waste is recovered during CPP production with most being vented to the atmosphere during drying and is a growing environmental concern. Improvements in limonene recovery and development of alternative value added co-products obtained from CPW could add substantial value to the citrus crop. For current CPP production, the energy required to dry CPW is the major cost involved and approximately 25 lb of limonene are obtained per ton of CPP produced. Since limonene is recovered during evaporation/concentration of pressed peel juice using a waste heat evaporator, little additional cost is associated with limonene recovery. The concentrated citrus molasses produced may be added back to the press cake or fermented to make ethanol, but only contains a third of the sugars in CPW that are fermentable by conventional yeast. While utilizing the entire CPW stream for ethanol using hydrolysis and fermentation is more involved, three times the amount of ethanol can be obtained compared to using press liquor alone. Most of the limonene must be removed as it inhibits fermentation. In the process developed 85–95% of the limonene contained in CPW can be removed and recovered by steam stripping. This greatly reduces concerns associated with the release of volatile organic compounds (VOCs) during processing of CPW and the limonene recovered has a value equal or greater than stripping costs. Using a mixture of enzymes and yeast, the CPW is then hydrolyzed and fermented simultaneously to produce ethanol followed by distillation to remove and recover the ethanol. Enzyme costs to hydrolyze and liquefy CPW have been reduced to less than a dollar per gallon of ethanol produced, and the economics for distillation are still being optimized. The distillation residues contain half the solids of raw citrus waste that can still be utilized as a CPP product. Other uses for the residues such as incorporation of the pectic materials into building product and paper additives, and ion exchange materials for wastewater remediation are also in development. Paper published with permission.
Reports on the topic "Limonin"
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Naim, Michael, Andrew Spielman, Shlomo Nir, and Ann Noble. Bitter Taste Transduction: Cellular Pathways, Inhibition and Implications for Human Acceptance of Agricultural Food Products. United States Department of Agriculture, February 2000. http://dx.doi.org/10.32747/2000.7695839.bard.
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Historically, the aversive response of humans and other mammals to bitter-taste substances has been useful for survival, since many toxic constituents taste bitter. Today, the range of foods available is more diverse. Many bitter foods are not only safe for consumption but contain bitter constituents that provide nutritional benefits. Despite this, these foods are often eliminated from our current diets because of their unacceptable bitterness. Extensive technology has been developed to remove or mask bitterness in foods, but a lack of understanding of the mechanisms of bitterness perception at the taste receptor level has prevented the development of inhibitors or efficient methods for reducing bitterness. In our original application we proposed to: (a) investigate the time course and effect of selected bitter tastants relevant to agricultural products on the formation of intracellular signal molecules (cAMP, IP3, Ca2+) in intact taste cells, in model cells and in membranes derived therefrom; (b) study the effect of specific bitter taste inhibitors on messenger formation and identify G-proteins that may be involved in tastant-induced bitter sensation; (c) investigate interactions and self-aggregation of bitter tastants within membranes; (d) study human sensory responses over time to these bitter-taste stimuli and inhibitors in order to validate the biochemical data. Quench-flow module (QFM) and fast pipetting system (FPS) allowed us to monitor fast release of the aforementioned signal molecules (cGMP, as a putative initial signal was substituted for Ca2+ ions) - using taste membranes and intact taste cells in a time range below 500 ms (real time of taste sensation) - in response to bitter-taste stimulation. Limonin (citrus) and catechin (wine) were found to reduce cellular cAMP and increase IP3 contents. Naringin (citrus) stimulated an IP3 increase whereas the cheese-derived bitter peptide cyclo(leu-Trp) reduced IP3 but significantly increased cAMP levels. Thus, specific transduction pathways were identified, the results support the notion of multiple transduction pathways for bitter taste and cross-talk between a few of those transduction pathways. Furthermore, amphipathic tastants permeate rapidly (within seconds) into liposomes and taste cells suggesting their availability for direct activation of signal transduction components by means of receptor-independent mechanisms within the time course of taste sensation. The activation of pigment movement and transduction pathways in frog melanophores by these tastants supports such mechanisms. Some bitter tastants, due to their amphipathic properties, permeated (or interacted with) into a bitter tastant inhibitor (specific phospholipid mixture) which apparently forms micelles. Thus, a mechanism via which this bitter taste inhibitor acts is proposed. Human sensory evaluation experiments humans performed according to their 6-n-propyl thiouracil (PROP) status (non-tasters, tasters, super-tasters), indicated differential perception of bitterness threshold and intensity of these bitter compounds by different individuals independent of PROP status. This suggests that natural products containing bitter compounds (e.g., naringin and limonin in citrus), are perceived very differently, and are in line with multiple transduction pathways suggested in the biochemical experiments. This project provides the first comprehensive effort to explore the molecular basis of bitter taste at the taste-cell level induced by economically important and agriculturally relevant food products. The findings, proposing a mechanism for bitter-taste inhibition by a bitter taste inhibitor (made up of food components) pave the way for the development of new, and perhaps more potent bitter-taste inhibitors which may eventually become economically relevant.
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Roth, R., D. Ebert, and T. J. Shepodd. The evaluation of potential limonene scavengers. Office of Scientific and Technical Information (OSTI), January 1995. http://dx.doi.org/10.2172/10114752.
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Somer, T. A. Aging of D-limonene-cleaned assemblies. Office of Scientific and Technical Information (OSTI), April 1994. http://dx.doi.org/10.2172/10170070.
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Somer, T. A. Aging of d-Limonene-cleaned assemblies. Final report. Office of Scientific and Technical Information (OSTI), August 1995. http://dx.doi.org/10.2172/95178.
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Taiz, Lincoln. Regulation of Vacuolar pH in Citrus limon. Office of Scientific and Technical Information (OSTI), June 2005. http://dx.doi.org/10.2172/841076.
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Lee, Jungjae, Hailin Su, Rohan L. Fernando, Dorian J. Garrick, and Jeremy Taylor. Characterization of the F94L Double Muscling Mutation in Pure- and Crossbred Limousin Animals. Ames (Iowa): Iowa State University, January 2015. http://dx.doi.org/10.31274/ans_air-180814-1278.
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Droby, Samir, Tim R. Gottwald, Richard Stange, Efraim Lewinsohn, and T. Gregory McCollum. Characterization of the biochemical basis of host specificity of Penicillium digitatum and Penicillium italicum on citrus fruit. United States Department of Agriculture, May 2008. http://dx.doi.org/10.32747/2008.7587726.bard.
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l. This research demonstrates that citrus fruit volatiles play an important role in host recognition by P. digitatum and P. italicum. 2. Volatiles derived from non-host fruits and vegetables (apple, pear, tomato, pepper, strawberry and avocado) had no effect on promotion of spore germination and growth of citrus pathogens. 3. Citrus volatiles have a specific stimulatory effect solely on P. digitatum and P. italicum. Non-citrus pathogens such as P. expansum and B. cinerea not affected orinhibited by the volatile materials. The specific stimulatory effect of fruit peelvolatiles on citrus pathogens and inhibitory effect on non-pathogens indicateimport ant role of volatile compounds in the host selectivity of citrus postharvestpathogens. 4. Comparative CG-MS quantification was per formed and identification of volatileconstituents of citrus commercial oils, peel extracts and the headspace of thewounded fruits was completed. Monoterpenehydrocarbons (limonene, a-pinene,sabinene, and myrcene) were the most abundant in all volatiles regardless of thesource. 5. Our results demonstrated stimulation of germination and germ tube growth in both P. digitatum and P. italicum by limonene, myrcene, a-pinene, and b-pinene). Limonenewas show n to be the most efficient in induction of germination and growth in bothpathogens. 6. P. digitatum spores placed on the surface of lemon fruit, adjacent to a wounded oil gland, were induced to germinate and grow, thus supporting all the in vitro results and demonstrating that the phenomenon of stimulation of germination and growth occurs on the fruit. 7. We established that P. digitatum is capable of biotransformation of limonene to a terpineol. a-terpinel was proved to be involved in induction of fungal sporulation process. 8. Chemotropism (directional growth) of P. digitatum towards the volatiles released from the oil glands on fruit surface was demonstrated. 9. Citrus germplasm screening work for fruit susceptibility/resistance for P. digitatum infection showed no definitive results regarding host range and susceptibility.Although the sour orange selections appear to show higher resistance to infection and decay development. 10. We demonstrated that P. expansum, non citrus pathogen, is capable of germinating in citrus fruit surface wounds, but it strongly induced host resistance mechanisms which restrict it growth and prevented decay development. The host (citrus fruit) reacted strongly by production of ROS. On the other hand, P. digitatum seems to actively suppress host natural resistance mechanisms possibly through inhibiting the production of ROS production.
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Historic trail map of the Limon 1 degree x 2 degrees Quadrangle, Colorado and Kansas. US Geological Survey, 1994. http://dx.doi.org/10.3133/i2468.
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