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Journal articles on the topic 'Limonin'

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Author: Grafiati

Published: 4 June 2021

Last updated: 21 February 2023

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1

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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2

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 2Ã—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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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.

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11

Breksa, Andrew P., and Gary D. Manners. "Evaluation of the Antioxidant Capacity of Limonin, Nomilin, and Limonin Glucoside." Journal of Agricultural and Food Chemistry 54, no. 11 (May 2006): 3827–31. http://dx.doi.org/10.1021/jf060901c.

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12

Mesquita, Estela, Eliane Barbosa, Maria Rita Olivati Estevam, Daniela Kharfan, Alberto José Cavalheiro, and Magali Monteiro. "The influence of rootstock and extraction setting on the Limonin and Flavonoids levels in orange juice during ripeness." Brazilian Journal of Development 8, no. 11 (November 24, 2022): 74904–20. http://dx.doi.org/10.34117/bjdv8n11-281.

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The influence of rootstock, maturity and extraction settings on limonin, hesperidin and narirutin levels of orange juice was evaluated. A liquid chromatographic method to determine limonin was developed and validated. The linear range was 0.410 to 61.5 µg.mL-1, with a linear correlation coefficient higher than 0.999. The limit of detection was 0.144 µg.mL-1and limit of quantification 0.363 µg; precision showed RSD≤5.0% and accuracy was from 92.6 to 100.4%. Limonin was identified in Pêra-Rio orange juices from Cleopatra mandarin and Rangpur lime rootstocks extracted in the NFC and FCOJ settings during the 2013 harvest. Limonin levels in Pêra-Rio orange juices ranged from 0.86 to 3.94 µg.mL-1 and flavonoids hesperidin and narirutin levels ranged from 12.00 to 26.02 µg.mL-1 for narirutin and from 122.12 to 175.01 µg.mL-1 for hesperidin. Principal component analysis was able to differentiate the juices from Cleopatra mandarin and Rangpur lime rootstocks according to ripeness, as well as extraction settings. Limonin and flavonoid levels reduced during maturation. Limonin levels were more expressive at the beginning of the harvest, especially in juice obtained with the FCOJ extraction setting. Hesperidin levels were about ten times higher than narirutin levels in all juices.

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13

Yamashita, Shuji, Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, and Masahiro Hirama. "Total Synthesis of Limonin." Angewandte Chemie 127, no. 29 (June 3, 2015): 8658–61. http://dx.doi.org/10.1002/ange.201503794.

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14

Yamashita, Shuji, Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, and Masahiro Hirama. "Total Synthesis of Limonin." Angewandte Chemie International Edition 54, no. 29 (June 3, 2015): 8538–41. http://dx.doi.org/10.1002/anie.201503794.

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15

Salom, S. M., J. A. Carlson, B. N. Ang, D. M. Grosman, and E. R. Day. "Laboratory Evaluation of Biologically-Based Compounds as Antifeedants for the Pales Weevil, Hylobius pales (Herbst) (Coleoptera: Curculionidae)." Journal of Entomological Science 29, no. 3 (July 1, 1994): 407–19. http://dx.doi.org/10.18474/0749-8004-29.3.407.

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Twenty plant-produced compounds or mixtures and one insect-produced semiochemical were evaluated as potential antifeedants for the pales weevil, Hylobius pales (Herbst). Initially, a choice laboratory feeding bioassay was conducted to screen the compounds and identify antifeedant activity. This was followed by a no-choice dose-response bioassay to further evaluate the most active compounds from the choice test. In the choice test, nine compounds inhibited feeding by H. pales on white pine, Pinus strobus L., twigs after 24 h: borneol, bornyl acetate, cucurbitacin, limonin, myrcene, neem extract, S (+) and R (−) carvone, and verbenone. Five of these compounds remained active after 48 h: borneol, limonin, neem extract, and both carvone isomers. In the no-choice test, 10% concentrations of S (+) carvone and limonin were the most active compounds for both males and females after 24 h. Borneol, verbenone, and R (−) carvone were active for males only. After 48 h, limonin and S (+) carvone remained most active compounds for males, with cucurbitacin and verbenone also showing activity. However, only limonin was active for females. Dose responses (0.1–10% concentrations) were strong for limonin and both carvone isomers. Cucurbitacin, diluted from a 0.3% concentrate, exhibited similar responses at all three doses, indicating that a more concentrated formulation may have potential as an antifeedant for H. pales. Limonin, both carvone isomers, and verbenone also show promise and will be further evaluated in future studies.

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16

Nurhaliza, Nurhaliza Nurhaliza, Rudiyansyah Rudiyansyah, and Harlia Harlia. "PERBANDINGAN METODE EKSTRAKSI TERHADAP KANDUNGAN LIMONIN PADA EKSTRAK METANOL BIJI JERUK SAMBAL (Citrus microcarpa Bunge) (COMPARISON OF EXTRACTION METHODS FOR LIMONIN CONTENT IN METHANOL EXTRACT OF SEEDS OF Citrus microcarpa Bunge)." Indonesian Journal of Pure and Applied Chemistry 5, no. 1 (April 30, 2022): 20. http://dx.doi.org/10.26418/indonesian.v5i1.53663.

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Limonin is a limonoid compound belonging to a terpenoid and it is found in Citrus plants including in the seeds of C. microcarpa. According to literature, limonin has been isolated by different methods from various Citrus plants with variable concentration. In this study, three extraction methods, maceration, soxhletation, and sonication were compared to examine a limonin concentration from the seeds of C. microcarpa. The purpose of this study is to determine the best extraction method which is able to give the highest concentration of limonin in the methanol extract. On the basis of phytochemical screening with the Liebermann-Burchard reagent and TLC data, it was found that the extracts from maceration, soxhletation, and sonication were positive for the triterpenoid. Further, based on the quantitative analysis, the average concentration of terpenoids obtained from the maceration, soxhletation, and sonication were 55.329%, 75.413%, and 83.473%, respectively. In conclusion, a sonication is the best method to extract a limonin by using terpenoid content.

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17

Phucharoenrak, Pakkapong, Chawanphat Muangnoi, and Dunyaporn Trachootham. "A Green Extraction Method to Achieve the Highest Yield of Limonin and Hesperidin from Lime Peel Powder (Citrus aurantifolia)." Molecules 27, no. 3 (January 26, 2022): 820. http://dx.doi.org/10.3390/molecules27030820.

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Green extraction is aimed at reducing energy consumption by using renewable plant sources and environmentally friendly bio-solvents. Lime (Citrus aurantifolia) is a rich source of flavonoids (e.g., hesperidin) and limonoids (e.g., limonin). Manufacturing of lime products (e.g., lime juice) yields a considerable amount of lime peel as food waste that should be comprehensively exploited. The aim of this study was to develop a green and simple extraction method to acquire the highest yield of both limonin and hesperidin from the lime peel. The study method included ethanolic-aqueous extraction and variable factors, i.e., ethanol concentrations, pH values of solvent, and extraction temperature. The response surface methodology was used to optimize extraction conditions. The concentrations of limonin and hesperidin were determined by using UHPLC-MS/MS. Results showed that the yields of limonin and hesperidin significantly depended on ethanol concentrations and extraction temperature, while pH value had the least effect. The optimal extraction condition with the highest amounts of limonin and hesperidin was 80% ethanol at pH 7, 50 °C, which yields 2.072 and 3.353 mg/g of limonin and hesperidin, respectively. This study illustrates a green extraction process using food waste, e.g., lime peel, as an energy-saving source and ethanol as a bio-solvent to achieve the highest amount of double bioactive compounds.

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18

Li, Yi, Runan Zhao, Yan Li, and Zhiqin Zhou. "Limonin Enhances the Antifungal Activity of Eugenol Nanoemulsion against Penicillium Italicum In Vitro and In Vivo Tests." Microorganisms 9, no. 5 (April 30, 2021): 969. http://dx.doi.org/10.3390/microorganisms9050969.

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Penicillium italicum, the cause of citrus blue mold, is a pathogenic fungus that seriously affects the postharvest quality of citrus fruit and causes serious economic loss. In this study, a eugenol nanoemulsion containing limonin, an antimicrobial component from citrus seeds, was prepared using a high-pressure microfluidizer and the antifungal activity of the nanoemulsions against P. italicum was evaluated based on the conidial germination rate, mycelial growth, and scanning electron microscopy analysis. The results showed that the minimum inhibitory concentration and the inhibition rate of limonin-loaded eugenol nanoemulsion was 160 μg/mL and 59.21%, respectively, which was more potent than that of the limonin-free eugenol emulsion. After treatment with the nanoemulsions, the integrity of the P. italicum cell membrane was disrupted, the cell morphology was abnormal, and the leakage of nucleic acid and protein was observed. In addition, the challenge test on citrus fruits revealed that the limonin-loaded eugenol emulsion inhibited citrus infection for longer periods, with an infection rate of 29.2% after 5 days. The current research shows that nanoemulsions containing limonin and eugenol have effective antifungal activity against P. italicum, and may be used as a substitute for inhibiting blue mold in citrus fruits.

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19

Widayanti, Setyo, Rudiyansyah Rudiyansyah, and Andi Hairil Alimuddin. "PENENTUAN STRUKTUR SENYAWA ANTIOKSIDAN LIMONOID DARI BIJI JERUK SAMBAL (Citrus microcarpa Bunge) KALIMANTAN BARAT." Indonesian Journal of Pure and Applied Chemistry 1, no. 3 (July 12, 2019): 77. http://dx.doi.org/10.26418/indonesian.v1i3.34193.

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Limonoid has been isolated from orange seeds of Citrus microcarpa Bunge using extraction and partitioning methods. It is a yellowish-white crystal with a melting point of 276-277 oC. Based on the phytochemical analysis and FTIR spectroscopy, 1H NMR and compared with the literature, the compound is limonin which is a triterpenoid. The purpose of this study was to determine the structure and evaluate antioxidant activity of the limonin. The antioxidant activity by DPPH obtained IC50 value of limonin was 199.18 ppm. Whereas, the test antioxidant activity by FRAP method using a comparative solution of ascorbic acid showed that there was an increasingly blue color change, which meant that antioxidant activity was stronger with activity value of 11.88 mgAAE /g sample.

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20

Shimizu, S., G. Fujii, R. Nakanishi, W. Onuma, Y. Ozaki, M. Mutoh, and T. Yano. "Suppression of intestinal carcinogenesis in APC-mutant mice by the citrus limonoid limonin." Journal of Nutrition & Intermediary Metabolism 1 (December 2014): 42–43. http://dx.doi.org/10.1016/j.jnim.2014.10.156.

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21

RAM, BHANU P., LARRY JANG, LORELEI MARTINS, and PRITHIPAL SINGH. "An Improved Enzyme Immunoassay for Limonin." Journal of Food Science 53, no. 1 (January 1988): 311–12. http://dx.doi.org/10.1111/j.1365-2621.1988.tb10245.x.

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22

Yamashita, Shuji, Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, and Masahiro Hirama. "ChemInform Abstract: Total Synthesis of Limonin." ChemInform 46, no. 38 (September 2015): no. http://dx.doi.org/10.1002/chin.201538199.

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23

Jia, Chengshu, Bin Hu, Yingying Ji, Yourui Su, Guoqing Gong, Qihua Zhu, and Yungen Xu. "Synthesis of Limonin Derivatives with Improved Anti-inflammatory and Analgesic Properties." Letters in Drug Design & Discovery 17, no. 3 (March 27, 2020): 285–99. http://dx.doi.org/10.2174/1570180816666181113102359.

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Background: Limonoids represent an important class of natural products which possess a broad range of biological activities. Albeit their enormous potentials as therapeutic candidates, they usually suffer from low bioavailability, poor aqueous solubility and relatively weak biological activities which result in significant challenges in the clinic applications. Therefore, the exploration and development of novel limonin derivatives with improved drug-like properties through the structural modifications recently have attracted great attention in the biological and medicinal chemistry field. Methods: Based on the structural modifications of C17-furan ring in limonin, a series of limonin derivatives was designed, synthesized and screened for their anti-inflammatory and analgesic activities in vivo. Results and Conclusion: Preliminary pharmacological studies revealed that most tested compounds exhibited more potent anti-inflammatory and analgesic efficacies than lead molecule limonin. Especially, for compound 3f, it exhibited a stronger anti-inflammatory effect than that of naproxen and comparable analgesic potency with aspirin. In the formalin test, 3f showed an obviously attenuated phase-II pain response which indicated that it may produce an anti-inflammatory effect in the periphery. Furthermore, the significantly low hERG inhibition (IC50 >100 μM) and high LD50 value of target molecule 3f further demonstrated it as a promising analgesic/anti-inflammatory candidate with excellent drug-like profiles.

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24

Yang, Qi, Feng Zhang, Shou-Hong Gao, Lian-Na Sun, and Wan-Sheng Chen. "Determination of Bioactive Compounds in Cortex Phellodendri by High-Performance Liquid Chromatography." Journal of AOAC INTERNATIONAL 93, no. 3 (May 1, 2010): 855–61. http://dx.doi.org/10.1093/jaoac/93.3.855.

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Abstract An HPLC method combined with a photodiode array detector was developed for quantitative determination of five bioactive compounds that belong to two subclasses, including limonin, phellodendrine, jatrorrhizine, palmatine, and berberine in Cortex Phellodendri. The analysis was performed on an Agilent Diamonsil C18 column (4.6 250 mm, 5 m) using a gradient of acetonitrile and 0.3 aqueous diethylamine phosphate (v/v), a flow rate of 0.8 mL/min, and a detection wavelength of 220 nm. The calibration curve was linear over the range of 2.5100.0 g/mL for both phellodendrine and jatrorrhizine, 5.0200.0 g/mL for palmatine, and 7.5300.0 g/mL for both berberine and limonin. The average recoveries ranged from 97.56 to 102.53 with RSD 1.00. Samples from different geographical locations were analyzed to evaluate the applicability of the established method, and the results indicated that the method was efficient, sensitive, and reliable for determining limonin and four alkaloids in Cortex Phellodendri.

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25

Breksa III, Andrew P., Marlene B. Hidalgo, and Rosalind Y. Wong. "Stability of limonin glucoside in beverage matrices." Journal of the Science of Food and Agriculture 88, no. 12 (September 2008): 2194–200. http://dx.doi.org/10.1002/jsfa.3344.

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26

Liang, Y., L. Xie, X. D. Liu, Y. Z. Hu, T. Lu, and G. J. Wang. "Gender differences in limonin pharmacokinetics in rats." European Journal of Drug Metabolism and Pharmacokinetics 30, no. 4 (December 2005): 243–48. http://dx.doi.org/10.1007/bf03190627.

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27

Mart�nez-Madrid, C., A. Manj�n, and J. L. Iborra. "Degradation of limonin by entrappedRhodococcus fascians cells." Biotechnology Letters 11, no. 9 (September 1989): 653–58. http://dx.doi.org/10.1007/bf01025277.

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Matsumoto, Ryoji, Daisuke Ikematsu, Terutaka Yoshioka, and Masashi Yamamoto. "Quantification of Limonin Glucoside, Phytonutrient Component, in Citrus by Means of an Enzyme Immunoassay Using Anti-limonin Antiserum." Horticultural Research (Japan) 7, no. 4 (2008): 481–89. http://dx.doi.org/10.2503/hrj.7.481.

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Gu, Min, Jin Sun, Ce Qi, Xiaokun Cai, Timothy Goulette, Mingyue Song, Xiaomeng You, David A. Sela, and Hang Xiao. "The gastrointestinal fate of limonin and its effect on gut microbiota in mice." Food & Function 10, no. 9 (2019): 5521–30. http://dx.doi.org/10.1039/c9fo01274e.

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30

Zhang, Aihua, Huiyu Wang, Hui Sun, Yue Zhang, Na An, Guangli Yan, Xiangcai Meng, and Xijun Wang. "Metabolomics strategy reveals therapeutical assessment of limonin on nonbacterial prostatitis." Food & Function 6, no. 11 (2015): 3540–49. http://dx.doi.org/10.1039/c5fo00489f.

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31

Glabasnia, Anneke, and Thomas Hofmann. "On the non-enzymatic liberation of limonin and C17-epilimonin from limonin-17-β-d-glucopyranoside in orange juice." European Food Research and Technology 228, no. 1 (June 17, 2008): 55–63. http://dx.doi.org/10.1007/s00217-008-0906-y.

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32

Muñoz, Mariela, Jessica Holtheuer, Lorena Wilson, and Paulina Urrutia. "Grapefruit Debittering by Simultaneous Naringin Hydrolysis and Limonin Adsorption Using Naringinase Immobilized in Agarose Supports." Molecules 27, no. 9 (April 30, 2022): 2867. http://dx.doi.org/10.3390/molecules27092867.

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Naringin and limonin are the two main bitter compounds of citrus products such as grapefruit juice. The aim of this investigation was to evaluate the reduction in both bitter components simultaneously using a combined biochemical and physical approach. The proposed strategy was based on the use of heterofunctional supports with glyoxyl groups that allow for the covalent immobilization of naringinase, which hydrolyses naringin and alkyl groups that allow for the adsorption of limonin. The supports were butyl-glyoxyl agarose (BGA) and octyl-glyoxyl agarose (OGA), which were characterized in terms of aldehyde group quantification and FTIR analysis. The optimal pH and temperature of free and immobilized enzymes were assessed. The maximum enzyme loading capacity of supports was analyzed. Debittering of grapefruit juice was evaluated using soluble enzyme, enzyme-free supports, and immobilized catalysts. Enzyme immobilized in BGA reduced naringin and limonin concentrations by 54 and 100%, respectively, while the use of catalyst immobilized in OGA allowed a reduction of 74 and 76%, respectively, obtaining a final concentration of both bitter components under their detection threshold. The use of OGA biocatalyst presented better results than when soluble enzyme or enzyme-free support was utilized. Biocatalyst was successfully applied in juice debittering in five repeated batches.

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33

Deng, Yujie, Yudong Fu, Shumin Xu, Ping Wang, Nailong Yang, Chengqian Li, and Qing Yu. "Detection and Structural Characterization of Nucleophiles Trapped Reactive Metabolites of Limonin Using Liquid Chromatography-Mass Spectrometry." Journal of Analytical Methods in Chemistry 2018 (2018): 1–9. http://dx.doi.org/10.1155/2018/3797389.

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Limonin (LIM), a furan-containing limonoid, is one of the most abundant components of Dictamnus dasycarpus Turcz. Recent studies demonstrated that LIM has great potential for inhibiting the activity of drug-metabolizing enzymes. However, the mechanisms of LIM-induced enzyme inactivation processes remain unexplored. The main objective of this study was to identify the reactive metabolites of LIM using liquid chromatography-mass spectrometry. Three nucleophiles, glutathione (GSH), N-acetyl cysteine (NAC), and N-acetyl lysine (NAL), were used to trap the reactive metabolites of LIM in in vitro and in vivo models. Two different types of mass spectrometry, a hybrid quadrupole time-of-flight (Q-TOF) mass spectrometry and a LTQ velos Pro ion trap mass spectrometry, were employed to acquire structural information of nucleophile adducts of LIM. In total, six nucleophile adducts of LIM (M1–M6) with their isomers were identified; among them, M1 was a GSH and NAL conjugate of LIM, M2–M4 were glutathione adducts of LIM, M5 was a NAC and NAL conjugate of LIM, and M6 was a NAC adduct of LIM. Additionally, CYP3A4 was found to be the key enzyme responsible for the bioactivation of limonin. This metabolism study largely facilitates the understanding of mechanisms of limonin-induced enzyme inactivation processes.

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Malik, Meenakshi, Abhijit Ganguli, and Moushumi Ghosh. "Enhancement of bioconversion efficiency of limonin byPseudmonas putidaG7." International Journal of Food Sciences and Nutrition 63, no. 1 (July 6, 2011): 59–65. http://dx.doi.org/10.3109/09637486.2011.596823.

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35

Ramos-Ibarra, J. R., E. Arriola-Guevara, G. Toriz, G. M. Guatemala-Morales, and R. I. Corona-González. "Enzymatic extraction of limonene, limonin and other relevant compounds from Citrus sinensis (orange) and Citrus aurantiifolia (lime) by-products." Revista Mexicana de Ingeniería Química 20, no. 3 (June 1, 2021): 1–11. http://dx.doi.org/10.24275/rmiq/bio2404.

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36

Wang, Shaochi, Xueqing Han, Yun Yang, Rui Chen, Zhaoyi Guo, Qihua Zhu, and Yungen Xu. "A practical synthesis of amino limonin/deoxylimonin derivatives as effective mitigators against inflammation and nociception." RSC Medicinal Chemistry 11, no. 7 (2020): 843–47. http://dx.doi.org/10.1039/d0md00117a.

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37

Liu, Qi Zhi, He Qin Li, and Zhi Long Liu. "Nematocidal Constituents from the Ethanol Extract ofEvodia rutaecarpaHort Unripe Fruits." Journal of Chemistry 2013 (2013): 1–5. http://dx.doi.org/10.1155/2013/939215.

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The ethanol extract of Chinese medicinal herb,Evodia rutaecarpaHort unripe fruits, was found to possess nematocidal activity against the root-knot nematodes,Meloidogyne incognita, during the screening program for new agrochemicals from local wild plants and Chinese medicinal herbs. Bioactivity-guided chromatographic separation of the ethanol extract ofE. rutaecarpaon repeated silica gel columns led to isolate five constituent components (two limonoids, evodol and limonin; three alkaloids, evodiamine, rutaecarpine, and wuchuyuamide I). Evodiamine (LC50=73.55 μg/mL) and rutaecarpine (LC50=120.85 μg/mL) exhibited stronger nematocidal activity againstM. incognitathan the crude ethanol extract ofE. rutaecarpa(LC50=131.54 μg/mL). Wuchuyuamide I, evodol, and limonin also possessed nematocidal activity againstM. incognitawith LC50values of 147.87 μg/mL, 155.02 μg/mL, and 197.37 μg/mL, respectively, but weaker than the crude ethanol extract ofE. rutaecarpa.

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38

Breksa, Andrew P., and Klaus Dragull. "Development and validation of a decigram-scale method for the separation of limonin from limonin glucoside by C-18 flash chromatography." Food Chemistry 113, no. 4 (April 2009): 1308–13. http://dx.doi.org/10.1016/j.foodchem.2008.08.046.

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39

Tsukuda, Kana, Masaki Mogi, Li-Juan Min, Fei Jing, Kosei Ohshima, Hirotomo Nakaoka, Harumi Kan-no, et al. "Limonin, A Citrus Limonoid, had no Apparent Effect on Cognitive Dysfunction in Mice with Chronic Cerebral Hypoperfusion." Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry 13, no. 2 (April 1, 2013): 139–43. http://dx.doi.org/10.2174/1871522211313020008.

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40

Cakrawati, D., and M. N. Handayani. "Microencapsulation of Limonin From Orange Juice Waste Using Maltodextrin." IOP Conference Series: Materials Science and Engineering 180 (March 2017): 012096. http://dx.doi.org/10.1088/1757-899x/180/1/012096.

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41

Herman, Z. "Limonin biosynthesis from obacunone via obacunoate in Citrus limon." Phytochemistry 23, no. 12 (November 26, 1985): 2911–13. http://dx.doi.org/10.1016/s0031-9422(00)80603-2.

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Halder, Debasish, Nando Dulal Das, Kyoung Hwa Jung, Mi Ran Choi, Moo Sung Kim, Sang Rin Lee, and Young Gyu Chai. "Cyclodextrin-Clathrated Limonin Suppresses Diet-Induced Obesity in Mice." Journal of Food Biochemistry 38, no. 2 (July 22, 2013): 216–26. http://dx.doi.org/10.1111/jfbc.12040.

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43

Herman, Zareb, and Shin Hasegawa. "Limonin biosynthesis from obacunone via obacunoate in Citrus limon." Phytochemistry 24, no. 12 (November 1985): 2911–13. http://dx.doi.org/10.1016/0031-9422(85)80025-x.

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44

Chinapongtitiwat, Vaniya, Saranya Jongaroontaprangsee, Naphaporn Chiewchan, and Sakamon Devahastin. "Important flavonoids and limonin in selected Thai citrus residues." Journal of Functional Foods 5, no. 3 (July 2013): 1151–58. http://dx.doi.org/10.1016/j.jff.2013.03.012.

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45

Lee, Da-Hye, Eun-Joo Jeon, Jiyun Ahn, Jin-Taek Hwang, Jinyoung Hur, Tae-Youl Ha, Chang Hwa Jung, and Mi Jeong Sung. "Limonin enhances osteoblastogenesis and prevents ovariectomy-induced bone loss." Journal of Functional Foods 23 (May 2016): 105–14. http://dx.doi.org/10.1016/j.jff.2016.02.008.

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46

Piyapolrungroj, Nusara, Panadda Phattanawasin, Uthai Sotanaphun, and May Phyu Thein Maw. "Role of Citrus Limonoid as a Possible Bioavailability Enhancer." Key Engineering Materials 859 (August 2020): 132–38. http://dx.doi.org/10.4028/www.scientific.net/kem.859.132.

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The oral delivery is the most practical route to deliver drugs into the body, however drug-metabolizing enzymes and drug transporters can play important roles in modulating drug absorption. This study intended to find a natural bioenhancer for improving drug bioavailability. Two limonoids, including limonin deepoxy and nomilin, isolated from pomelo pulp were studied and the inhibition effects on human CYP3A4 and P-gp were investigated. Testosterone 6β-hydroxylation was performed in recombinant human CYP3A4 to discover the effects on CYP activity. Daunorubicin transport in Caco-2 and calcein-AM uptake in LLC-PK1 and LLC-GA5-COL300 were conducted to evaluate the effects on P-gp function. The results show that both limonin deepoxy and nomilin could inhibit CYP3A4 and only nomilin exhibited mechanism-based inhibition. Nomilin was able to inhibit human P-gp in the concentration-dependent manner. Taken together, nomilin demonstrated strong activities on both CYP3A4 and P-gp, indicating that nomilin could possibly be used as a bioavailability enhancer.

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47

Khalil, Ashraf T., Galal T. Maatooq, and Khalid A. El Sayed. "Limonoids from Citrus reticulata." Zeitschrift für Naturforschung C 58, no. 3-4 (April 1, 2003): 165–70. http://dx.doi.org/10.1515/znc-2003-3-403.

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The seeds of Citrus reticulata afforded the new limonoid derivative, isolimonexic acid methyl ether, in addition to the the previously isolated limonin, deacetylnomilin, obacunone and ichangin. The structure elucidation was achieved primarily through 1D and 2-D-NMR analyses. The marginal antimalarial activity of isolimonexic acid methyl ether is reported.

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48

FELLERS, P. J., R. D. CARTER, and G. de JAGER. "Influence of Limonin on Consumer Preference of Processed Grapefruit Juice." Journal of Food Science 52, no. 3 (May 1987): 741–43. http://dx.doi.org/10.1111/j.1365-2621.1987.tb06716.x.

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49

Saraf, Nileshi, Swetha Barkam, Madison Peppler, Anna Metke, Abraham Vázquez-Guardado, Sushant Singh, Clarence Emile, Adrian Bico, Corey Rodas, and Sudipta Seal. "Microsensor for limonin detection: An indicator of citrus greening disease." Sensors and Actuators B: Chemical 283 (March 2019): 724–30. http://dx.doi.org/10.1016/j.snb.2018.12.067.

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RAHMAN, ATIQUR, MINKYUN NA, and SUN CHUL KANG. "ANTILISTERIAL POTENTIAL OF IMPERATORIN AND LIMONIN FROM PONCIRUS TRIFOLIATA RAFIN." Journal of Food Biochemistry 36, no. 2 (December 12, 2011): 217–23. http://dx.doi.org/10.1111/j.1745-4514.2010.00528.x.

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