Citrolimonin
limonin from citrus seeds
CAS: 1180-71-8
Molecular Formula: C26H30O8
Citrolimonin - Names and Identifiers
| Name | limonin from citrus seeds |
| Synonyms | LiMone Evodin Lemonin Limonin Limonine NSC 36508 AI3-37932 CCRIS 4047 Citrolimonin Obaculactone Lemon bitter Evodia lactone Dictamnolactone limonin from citrus seeds Limonoic acid, di-delta-lactone 7,16-Dioxo-7,16-dideoxylimondiol LiMonin, froM TetradiuM ruticarpuM LiMonin SynonyMs LiMonoate D-ring-lactone |
| CAS | 1180-71-8 |
| InChI | InChI=1/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 |
Citrolimonin - Physico-chemical Properties
| Molecular Formula | C26H30O8 |
| Molar Mass | 470.51 |
| Density | 1.39±0.1 g/cm3(Predicted) |
| Melting Point | 298 C |
| Boling Point | 67 °C |
| Specific Rotation(α) | D -128° (c = 1.21 in acetone) |
| Flash Point | 358°C |
| Solubility | It is easy to dissolve ester organic solvents, difficult to dissolve in water, and has high solubility in methanol and ethanol. |
| Vapor Presure | 9.96E-18mmHg at 25°C |
| Appearance | White crystal |
| Color | White to Off-White |
| Maximum wavelength(λmax) | 285nm(lit.) |
| Merck | 14,5494 |
| Storage Condition | 2-8°C |
| Refractive Index | 1.602 |
| MDL | MFCD00075922 |
| Physical and Chemical Properties | It is easy to dissolve ester organic solvents, difficult to dissolve in water, and has high solubility in methanol and ethanol. It is derived from the fruit of the Rutaceae plant Citrus aurantium. |
Citrolimonin - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | RR1122000 |
| HS Code | 29321900 |
Citrolimonin - Reference
| Reference Show more | 1. Feng Xin, Zhao Wenjun, Hou Ting, et al. Determination of 14 Components in Ermiao Powder Extract by UPLC-MS/MS [J]. Chinese Journal of Experimental Prescritique 2017 023(021):79-85. 2. Xu Hanglin, Deng Gang, Jiao Congcong, et al. Study on Separation of Limonin from Waste Residue of Bergamot Beverage [J]. Journal of Zhejiang Normal University (Natural Science Edition) 2012(03):322-325. 3. Zhang Hongmei, Li Guo, Song Long, et al. Pharmacognosy identification of Evodia rutaecarpa and counterfeit smelly spicy tree fruits [J]. Chinese herbal medicine 2016 (phase 3):515-518. 4. Liu Xuying, Wang Wenlan, Ge Zhaohui, et al. Quality Evaluation of Evodia rutaecarpa Based on Optimized Microquantitative Method [J]. Modern Chinese Traditional Chinese Medicine, 2018, 20(05):561-564. 5. Sun Xiaowen, Peng Ying, He Wanying, et al. Star Point Design-Effect Surface Methodology to Optimize Extraction Process of Limonin from Enocarp of Hovenia trifolia [J]. Food Industry Technology, 2018, v.39;No.402(10):175-179. 6. Tian Guangwen, Li Pengfei, Du Lihua, study on Optimization of Extraction Process of Antimicrobial Agents from Pomelo Peel [J]. Anhui Agricultural Sciences, 2015, 000(005):259-262,265. 7. Zhang Hongmei, Li Guo, Song Long, et al. Fingerprint Analysis and Content Determination of Evodia rutaecarpa from Guizhou and Zhejiang [J]. Chinese Journal of Experimental Prescritique, 2014, 20(017):69-73. 8. Shao Jinhua, dong Jiabao, Chen Li. Extraction and Purification of Limonin from Fragrant Pomelo Seeds [J]. Food and Fermentation Industry, 2012(11):189-192. 9. Li Yibing, Gong Guizhi, Peng Zhuchun, Wang Yanjie, Wang Jiong, Hong Qibin. Changes of Limonin Content in Juice of Different Sweet Orange Varieties [J]. Food and Fermentation Industry 2017 43(02):201-205. 10. Yu Meng, Liu Chunquan, Niu Liying, et al. Effect of debittering treatment on the quality of citron juice [J]. Jiangsu Agricultural Sciences, 2014, 42(002):211-214. 11. Zhang Shan, Huang Xuesong. Simultaneous Determination of Four Flavonoid Glycosides and Limonin in Pomelo by High Performance Liquid Chromatography [J]. Food and Machinery, 2021,37(03):58-63. 12. Zhou Jianxin, Shen Shuo, Du Maobo, Li Yujie, Sun Yi, He Aiping, Yao Yao, Wang Mingshuo, Liu Shuzhi, Yin Yongqin. Based on UPLC-Q-TOF-MS technology and integrated pharmacological methods to explore the molecular mechanism of transdermal components of Evodia rutaecarpa and its treatment of diarrhea [J]. Chinese journal of experimental prescriptions, 2021,27(07):112-120. 13. Zhang, Ying, et al. "Development and validation of a sensitive LC-MS/MS say for quantification of bruceine D in rat plasma." Biomedical Chromatography 30.11 (2016): 1873-1876.https:// doi.org/10.1002/bmc.3724 14. [IF = 4.411] Jun Zhang et al. "Effects of Postharvest Time, Heat Treatment, pH and Filtration on the Limonin Content in Newhall Navel Orange (Citrus sinensis Osbeck cv. Newhall) Juice." Molecules. 2018 Oct;23(10):2691 15. [IF = 1.902] Yining Zhang et al. "Development and validation of a sensitive LC-MS/MS say for quantification of bruceine D in rat plasma." Biomed Chromatogr. 2016 Nov;30(11): 1873-1876 16. [IF = 4.411] Liuyi Yu et al. "Systematic Detection and Identification of Bioactive Ingredients from Citrus aurantium L. var. amara Using HPLC-Q-TOF-MS Combined with a Screening Method." Molecules. 2020 Jan;25(2):357 17. [IF = 4.268] Runyu Yang et al. "Limonin ameliorates acetaminophen-induced hepatotoxicity by activating Nrf2 antioxidative pathway and inhibiting NF-κB inflammatory response via upregulating Sirt1." Phytomedicine. 2020 Apr;69:153211 18. [IF = 4.192] Runyu Yang et al. "Limonin Attenuates LPS-Induced Hepatotoxicity by Inhibiting Pyroptosis via NLRP3/Gasdermin D Signaling Pathway." J Agr Food Chem. 2021;69(3):982-991 19. [IF = 3.943] Changqin Song et al. "Limonin ameliorates dextran sulfate sodium-induced chronic colitis in ice by inhibiting PERK-ATF4-CHOP pathway of ER stress and NF-κB signaling." Int Immunopharmacol. 2021 Jan;90:107161 20. [IF = 3.463] Yun Liu et al. "Structural diversity and distribution of limonoids in pummelo (Citrus grandis) fruit revealed by comprehensive UHPLC-MS/MS analysis." Sci Hortic-Amsterdam. 2021 May;282:109996 21. [IF = 3] Qu Lala et al. "Phenotypic assessment and screening of ETA/ETB receptors with label-free dynamic mass redistribution say." N-S Arch Pharmacol. 2020 Jun;393(6):937-950 22. [IF = 2.408] Wei Ling et al. "Evaluation of Pomelo Seed Extracts as Natural Antioxidant, Antibacterial, Herbicidal Agents, and their Functional Components." Chemistry & Biodiversity. 2021 Oct 27 23. [IF = 4.556] Jingyi Zhang et al.Variations of the chemical composition of Citrus sinensis Osbeck cv. Newhall fruit in relation to the symptom severity of Huanglongbing.J Food Compos Anal. 2021 Nov;:104269 24. [IF = 5.81] Yunjia Li et al. "Limonin Alleviates Non-alcoholic Fatty Living Disease by Reducing Lipid Accumulation, Suppressing Inflammation and Oxidative Stress." Front Pharmacol. 2021; 12: 801730 |
Citrolimonin - Reference Information
| limonin compound | limonin compound is a triterpenoid derivative widely found in Rutaceae and Dunidae plants, and is one of the bitter ingredients of citrus juice. Glucose derivatives exist in mature fruits. Plant seeds are the main source of these compounds aglycones and glucosides, with the highest content in grape seeds. The average concentration of limonin glycoside was (320±48)mg/kg,8 grape juice was (190±36)mg/kg, and 4 lemon juice was (83±10)mg/kg. The content of glycosides in citrus fruit juice is very low, generally only about 2 mg/kg (Hasegawa 1994). The molecular structure of this type of compound is that the D ring contains furan molecules, which can induce glutathione S-transferase. From the specific compound point of view, the effect of limonin is not as strong as that of nomilin Nomilin. The former is inactive for the enzyme in the liver, and the latter can induce the enzyme as low as 5mg. Both are more active in the small intestine than in the liver. Nomilin can inhibit the formation of benzopyrene-DNA adducts in liver and target tissues, and inhibit benzopyrene-induced lung cancer. In the mouse test, the inhibition of DMBA-induced skin cancer was stronger than limonin in the initial stage, but not as good as it in the promotion stage. Other structurally related limonin compounds such as Yichang Silver (Ichangin), isoobacunor C and Phelloxanthone are also good inducers of glutathione S-transferase (GST). The above information was collected by Andy. |
| physical and chemical properties | limonin is a bitter crystal (dichloromethane + isopropanol or acetic acid). Insoluble in water, ether, soluble in methanol, ethanol, glacial acetic acid. Melting point 298 ℃, optical rotation -128 (c = 1.21, acetone). chemical structural formula of limonin |
| bitter ingredient of citrus juice | limonin, also known as phellodendron and evodiamine, is the bitter ingredient of citrus juice beverage. sweet orange is the most widely cultivated citrus variety in the world with good flavor and is widely used for juice processing except fresh food. Oranges are generally thinner, ranging from orange to yellow, and the quality of juice is good, so they are also suitable for juice processing. The bitter ingredients in citrus juice are flavonoids and limonin. Limonin has a strong bitter taste, and its threshold is about 1 mg/kg in pure water and 2 mg/kg in 10% sugar solution. Some citrus juices have a bitter taste when heated, because the non-bitter limonin monolactone, which is the precursor of limonin, breaks down into lactones and becomes bitter limonin when it comes into contact with acidic juice. Some fresh citrus juices also have a bitter taste, mainly from limonoid, which decreases as the fruit ripens. |
| pharmacological action | limonin analog has anti-tumor, insect antifeedant, antiviral, analgesic, anti-inflammatory, hypnotic and other biological activities. The physiological activity of limonin analogs was studied from the medicinal plants of the family. (1) analgesic and anti-inflammatory effects some studies have isolated limonin from rutaecarpa (evodiarutaecarpavar.bodinieri) and carried out corresponding experimental studies. For example, the experiment found that by giving 100mg/kg limonin to mice, the number of licks in mice can be significantly reduced. At the same time, through the experimental study of the vascular permeability of the acetic acid channel, the response to the foot swelling induced by bradykinin and the ear swelling induced by arachidonic acid, the product has obvious analgesic and anti-inflammatory effects. (2) anti-anxiety and sedative effects hypnotic test studies on anesthetized mice found that limonin, nomelin, obalidone, 7-obalidone, 70r lemon bitter alcohol and other limonin compounds can prolong the sleep time of mice caused by monochloraldose and uratan, and the sedative effect of nomelin is stronger. (3) insecticidal activity regarding the feeding resistance of limonin analogs, the activity of imidonin isolated from the seeds of a zadirach ta indica is high and has effect on more than 60 kinds of insects. Citrus limonin analogs (obalcone, nomelin, limonin) are also active against insects and termites. It is of great significance to develop and utilize these naturally occurring limonin analogs. (4) Other effects In addition to the above biological effects, it also has antioxidant activity, antibacterial property, HIV inhibition, cholesterol reduction, obvious diuretic effect, improvement of cardiovascular and cerebrovascular circulation, improvement of sleep, anti-virus, regulation of cytochrome and other effects, and has good health care functions. |
| anti-tumor effect | limonin is a crystalline substance extracted from citrus branches and leaves and grapefruit kernels of rutaceae plants. this substance has strong anti-cancer activity, can inhibit the carcinogenic effect of chemical carcinogens, and also has strong anti-cancer effect in the promoting stage. literature reports, citrus limonin compounds have obvious anti-tumor effect, the guinea pig oral administration of limonin and limelin compounds can enhance the small intestinal mucosa and liver glutathione transferase (GST) activity 3-4 times. Generally speaking, compounds that induce GST activity can inhibit the carcinogenesis of chemical carcinogens. Because limonin activates the activity of this enzyme, it inhibits the carcinogenesis of chemical carcinogens. For example, first take limonin and normilin to animals, and then use chemical carcinogens such as benzopyrene (benzopyrene) to induce the growth of tumors in experimental animals. It was found that animals that did not take limonin and normilin 100% form lung cancer, Gastric cancer, skin cancer, and taking this drug in advance, only 20-30% of animals get cancer. The literature also reports that citrus limonin compounds also have inhibitory effects on colon cancer and breast cancer, and the effect is stronger than that of anticancer drug tamoxifen (tamoxifen). The development of limonin has improved the quality of life of cancer patients, reduced cancer mortality, brought good news to many patients, and has a variety of antiviral biological activity effects. |
| clinical application | limonin analogs were studied to remove them from citrus fruits and to improve commodity value. However, with the continuous in-depth research on the physiological activities of limonin analogs, more and more attention has been paid to the research on the recovery, purification and application of limonin analogs from citrus. Limonin analogs have physiological activities such as tumor suppression and should be vigorously developed as functional food materials. Microherb after years of research, high purity 98% limonin has been successfully separated by advanced chromatographic separation technology, which is widely used in medicine, functional food supplements and biological pesticides. |
| artificial synthesis | at present, the main method of synthesizing limonin by biological means in China is starting from kanesane or Euphorbia alkane triterpene, through methyl migration, oxidation, side chain ring combined to remove 4 C to form a basic skeleton, and then through a series of post-modification reactions, A class of natural products with complex structure and rich types are formed. Because they originate from the tetra-cyclic triterpene skeleton and lose 4 C, they are also called tetra-descending triterpene. The complex structure of limonin compounds not only attracted the attention of natural product chemists, but also challenged the skills of organic synthesis. |
| chemical properties | easy to dissolve ester organic solvents, difficult to dissolve in water, and highly soluble in methanol and ethanol. It is derived from the fruit of the Rutaceae plant Citrus aurantium. |
| use | has anti-proliferative and anti-apoptotic activities on several tumor cell lines, and inhibits azomethane oxide (azoxymethane)-induced colon cancer in rats. By inhibiting the activity of HIV-1 protease, inhibiting the replication of HIV-1 virus in monocytes, macrophages and monocytes, used for the determination of limonin content in citrus products. |
| EPA chemical information | information provided by: ofmpub.epa.gov (external link) |
Last Update：2024-04-09 21:54:55
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