Limonin (BioDeep_00000372638)

Main id: BioDeep_00000000269

Secondary id: BioDeep_00000018142

natural product PANOMIX_OTCML-2023


代谢物信息卡片


11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR-(2aalpha,4abeta,4bR,5aalpha,8alpha,8aalpha,10aalpha,10bR*,14aalpha))-

化学式: C26H30O8 (470.194058)
中文名称: 吴茱萸内酯, 柠檬苦素, 柠檬苦素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.47%

分子结构信息

SMILES: C(C721)(CCC(C(C)57)(C(C6)(C4([H])CC(O6)=O)C(CC5=O)([H])C(C)(C)O4)[H])(C(c(c3)coc3)OC(=O)C(O2)1)C
InChI: InChI=1S/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

描述信息

Limonin is a limonoid, an epoxide, a hexacyclic triterpenoid, a member of furans, an organic heterohexacyclic compound and a lactone. It has a role as a metabolite, an inhibitor and a volatile oil component.
Limonin is a natural product found in Citrus tankan, Flacourtia jangomas, and other organisms with data available.
Limonin is a triterpenoid compound rich in citrus fruits that has antiviral and antitumor activities.
Limonin is a triterpenoid compound rich in citrus fruits that has antiviral and antitumor activities.

同义名列表

48 个代谢物同义名

11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR-(2aalpha,4abeta,4bR,5aalpha,8alpha,8aalpha,10aalpha,10bR*,14aalpha))-; rel-(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4,3:3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione; (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4,3:3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione; 11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)-; (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4,3:3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione; (4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4,3:3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione; (4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(3-furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4,3:3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione; (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione; (4aS,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4,3:3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione; 11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furyl)decahydro-2,2,4a,8a-tetramethyl-; Limone; Citrolimonin; Evodine; Dictamnolactone; Obaculactone; Limonin, from citrus seeds, >90\\% (HPLC); limonoic acid 3,19:16,17-dilactone; Limonoic acid 3,19:16,17 dilactone; Limonoic acid, di-.delta.-lactone; Limonoic acid di-.delta.-lactone; 7,16-dioxo-7,16-dideoxylimondiol; Limonoic acid, di-delta-lactone; limonoic acid di-delta-lactone; 3-furyl(tetramethyl)[?]trione; Limonin, analytical standard; KBDSLGBFQAGHBE-MSGMIQHVSA-N; limonin from citrus seeds; Limonoate D-ring-lactone; Spectrum2_001728; Spectrum4_001140; Spectrum3_001012; Spectrum5_000935; Dictamnolactone; UNII-L0F260866S; Tox21_111513_1; KBio3_001983; Citrolimonin; obaculactone; LIMONIN [MI]; Tox21_111513; ACon1_001996; Evodia fruit; L0F260866S; AI3-37932; 1ST157590; Limonine; Limonin; Linonin; Limone; Limoni; Evodin; NCGC00178483-05_C26H30O8_1H,3H-Oxireno[c]pyrano[4,3:2,3]furo[3,4:5,6]naphtho[1,2-d]pyran-3,8,10(6H,9aH)-trione, 12-(3-furanyl)decahydro-6,6,8a,12a-tetramethyl-, (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-



数据库引用编号

43 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

52 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Di Sun, Yifan Liu, Zihui Jin, Bo Xu, Yaqi Jin, Qiyang Zhao, Yue He, Jing Li, Yaohai Zhang, Yongliang Cui. Preparation of limonin monoclonal antibody and establishment of a sensitive icELISA for analyzing limonin in citrus and herbal samples. Food chemistry. 2024 Jul; 447(?):138989. doi: 10.1016/j.foodchem.2024.138989. [PMID: 38492297]
  • Wanling Yang, Yiyao Liang, Yujie Liu, Yunan Yao, Zhiqian Yu, Baizhong Chen, Yi Cai, Minyan Wei, Guodong Zheng. Enhancement of hepatoprotective activity of limonin from citrus seeds against acetaminophen-induced liver injury by HSCCC purification and liposomal encapsulation. Fitoterapia. 2024 Jun; 175(?):105899. doi: 10.1016/j.fitote.2024.105899. [PMID: 38471575]
  • Yadie Xiang, Xianke Zhou, Hong Zhou, Dier Li, Menghua Zhong, Xue Hong, Dongyan Song, Yinyi Long, Xi Zeng, Yudan Chen, Jiayi Zhou, Dongning Liang, Haiyan Fu. Limonin ameliorates cisplatin-induced acute liver injury by inhibiting 11β-hydroxysteroid dehydrogenase type 1. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Oct; 168(?):115680. doi: 10.1016/j.biopha.2023.115680. [PMID: 37832403]
  • Shan Jiang, Xiao-Mei Zhao, Jie Guo, Jia-Ping Wang, Xiao-Qian Liu, Wei-Hong Feng, Li-Hua Yan, Zhi-Min Wang. [Hot water washing processing technology of Euodiae Fructus based on change laws of active components and tastes]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Jul; 48(13):3485-3497. doi: 10.19540/j.cnki.cjcmm.20230403.301. [PMID: 37475001]
  • Ghulam Mustafa, Shumaila Younas, Hafiza Salaha Mahrosh, Mohammed Fahad Albeshr, Eijaz Ahmed Bhat. Molecular Docking and Simulation-Binding Analysis of Plant Phytochemicals with the Hepatocellular Carcinoma Targets Epidermal Growth Factor Receptor and Caspase-9. Molecules (Basel, Switzerland). 2023 Apr; 28(8):. doi: 10.3390/molecules28083583. [PMID: 37110817]
  • Pakkapong Phucharoenrak, Chawanphat Muangnoi, Dunyaporn Trachootham. Metabolomic Analysis of Phytochemical Compounds from Ethanolic Extract of Lime (Citrus aurantifolia) Peel and Its Anti-Cancer Effects against Human Hepatocellular Carcinoma Cells. Molecules (Basel, Switzerland). 2023 Mar; 28(7):. doi: 10.3390/molecules28072965. [PMID: 37049726]
  • Jie Pan, Chutian Wu, Rong Tan, Yufen Liao, Guode Zhao, Wei Li, Ying Peng, Weiwei Li, Jiang Zheng. Difference in hepatotoxicity of furan-containing components in cortex dictamni correlates the efficiency of their metabolic activation. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Mar; 114(?):154778. doi: 10.1016/j.phymed.2023.154778. [PMID: 36996529]
  • Bo Jia, Leyi Zhao, Pengpeng Liu, Meng Li, Zhilei Tian. Limonin ameliorates indomethacin-induced intestinal damage and ulcers through Nrf2/ARE pathway. Immunity, inflammation and disease. 2023 Feb; 11(2):e787. doi: 10.1002/iid3.787. [PMID: 36840501]
  • Wei Wang, Li Yang, Minjie Hu, Yonglin Yang, Qiang Ma, Jiayu Chen. Network Pharmacology to Reveal the Molecular Mechanisms of Rutaceous Plant-derived Limonin Ameliorating Non-alcoholic Steatohepatitis. Critical reviews in immunology. 2023; 43(5):11-23. doi: 10.1615/critrevimmunol.2023050080. [PMID: 37831520]
  • Seshu Vardhan, Suban K Sahoo. Computational studies on the interaction of SARS-CoV-2 Omicron SGp RBD with human receptor ACE2, limonin and glycyrrhizic acid. Computers in biology and medicine. 2022 05; 144(?):105367. doi: 10.1016/j.compbiomed.2022.105367. [PMID: 35247766]
  • Pakkapong Phucharoenrak, Chawanphat Muangnoi, Dunyaporn Trachootham. A Green Extraction Method to Achieve the Highest Yield of Limonin and Hesperidin from Lime Peel Powder (Citrus aurantifolia). Molecules (Basel, Switzerland). 2022 Jan; 27(3):. doi: 10.3390/molecules27030820. [PMID: 35164083]
  • Nur Iliyani Mohd Ishak, Suhaila Mohamed, Iffah Nadhira Madzuki, Noordin Mohamed Mustapha, Norhaizan Mohd Esa. Limonin modulated immune and inflammatory responses to suppress colorectal adenocarcinoma in mice model. Naunyn-Schmiedeberg's archives of pharmacology. 2021 09; 394(9):1907-1915. doi: 10.1007/s00210-021-02101-6. [PMID: 34009457]
  • Wei Zhang, Mengjiao Wang, Huijie Song, Chengfeng Gao, Dongmei Wang, Huiming Hua, Yingni Pan, Xiaoqiu Liu. CYP3A4 inducer aggravates big flower Evodiae Fructus-induced hepatotoxicity whereas limonin attenuates its hepatotoxicity. Journal of ethnopharmacology. 2021 Jan; 264(?):113277. doi: 10.1016/j.jep.2020.113277. [PMID: 32810616]
  • Yulin Ren, A Douglas Kinghorn. Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones. Journal of medicinal chemistry. 2020 12; 63(24):15410-15448. doi: 10.1021/acs.jmedchem.0c01449. [PMID: 33289552]
  • Youtian Cui, Steven D Allmon, Justin B Siegel. Functional characterization and reclassification of an enzyme previously proposed to be a limonoid UDP-glucosyltransferase. Journal of the science of food and agriculture. 2020 Oct; 100(13):4870-4878. doi: 10.1002/jsfa.10547. [PMID: 32483918]
  • Runyu Yang, Changqin Song, Jiaxi Chen, Lvqi Zhou, Xiubo Jiang, Xiaomei Cao, Yang Sun, Qi Zhang. Limonin ameliorates acetaminophen-induced hepatotoxicity by activating Nrf2 antioxidative pathway and inhibiting NF-κB inflammatory response via upregulating Sirt1. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Apr; 69(?):153211. doi: 10.1016/j.phymed.2020.153211. [PMID: 32259676]
  • Li-Jun Li, Wan-Seng Tan, Wen-Jing Li, Yan-Bing Zhu, Yi-Sheng Cheng, Hui Ni. Citrus Taste Modification Potentials by Genetic Engineering. International journal of molecular sciences. 2019 Dec; 20(24):. doi: 10.3390/ijms20246194. [PMID: 31817978]
  • Cuike Gong, Lei Qi, Yanxia Huo, Shiran Zhang, Xuecong Ning, Linlin Bai, Zhihua Wang. Anticancer effect of Limonin against benzo(a)pyrene-induced lung carcinogenesis in Swiss albino mice and the inhibition of A549 cell proliferation through apoptotic pathway. Journal of biochemical and molecular toxicology. 2019 Dec; 33(12):e22374. doi: 10.1002/jbt.22374. [PMID: 31702096]
  • Shunming Fan, Chunling Zhang, Ting Luo, Jiaqi Wang, Yu Tang, Zhimin Chen, Lingying Yu. Limonin: A Review of Its Pharmacology, Toxicity, and Pharmacokinetics. Molecules (Basel, Switzerland). 2019 Oct; 24(20):. doi: 10.3390/molecules24203679. [PMID: 31614806]
  • Shijia Liu, Shufang Zhang, Xiangyu Lv, Jiawei Lu, Cong Ren, Zhiqin Zeng, Lufeng Zheng, Xianke Zhou, Haiyan Fu, Dong Zhou, Yugen Chen. Limonin ameliorates ulcerative colitis by regulating STAT3/miR-214 signaling pathway. International immunopharmacology. 2019 Oct; 75(?):105768. doi: 10.1016/j.intimp.2019.105768. [PMID: 31382166]
  • Yikun Liu, Wei Zhou, Zhenkun Mao, Zilin Chen. Analysis of Evodiae Fructus by capillary electrochromatography-mass spectrometry with methyl-vinylimidazole functionalized organic polymer monolilth as stationary phases. Journal of chromatography. A. 2019 Sep; 1602(?):474-480. doi: 10.1016/j.chroma.2019.06.011. [PMID: 31202495]
  • Min Gu, Jin Sun, Ce Qi, Xiaokun Cai, Timothy Goulette, Mingyue Song, Xiaomeng You, David A Sela, Hang Xiao. The gastrointestinal fate of limonin and its effect on gut microbiota in mice. Food & function. 2019 Sep; 10(9):5521-5530. doi: 10.1039/c9fo01274e. [PMID: 31418448]
  • Wei Zhao, Mingyuan Wu, Lijuan Cui, Wenxia Du. Limonin attenuates the stemness of cervical carcinoma cells by promoting YAP nuclear-cytoplasmic translocation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Mar; 125(?):621-628. doi: 10.1016/j.fct.2019.02.011. [PMID: 30738134]
  • Shijia Liu, Guoliang Dai, Luning Sun, Bingting Sun, Du Chen, Lei Zhu, Yao Wang, Li Zhang, Peidong Chen, Dong Zhou, Wenzheng Ju. Biotransformation and Metabolic Profile of Limonin in Rat Liver Microsomes, Bile, and Urine by High-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry. Journal of agricultural and food chemistry. 2018 Oct; 66(40):10388-10393. doi: 10.1021/acs.jafc.8b02057. [PMID: 30260225]
  • Noura A Hassan, Hany M El Bassossy, Ahmed Fahmy, Mona F Mahmoud. Limonin alleviates macro- and micro-vascular complications of metabolic syndrome in rats: A comparative study with azelnidipine. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Apr; 43(?):92-102. doi: 10.1016/j.phymed.2018.03.044. [PMID: 29747759]
  • Shijia Liu, Peidong Chen, Nongshan Zhang, Luning Sun, Guoliang Dai, Lei Zhu, Changyin Li, Yang Zhao, Li Zhang, Haiyan Fu, Wenzheng Ju. Comprehensive characterization of the in vitro and in vivo metabolites of limonin in human samples using LC-Q-TOF/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Nov; 1068-1069(?):226-232. doi: 10.1016/j.jchromb.2017.10.035. [PMID: 29107222]
  • Zaizhi Liu, Yuangang Zu, Lei Yang. A process to preserve valuable compounds and acquire essential oils from pomelo flavedo using a microwave irradiation treatment. Food chemistry. 2017 Jun; 224(?):172-180. doi: 10.1016/j.foodchem.2016.12.027. [PMID: 28159252]
  • Fusheng Wang, Xiaohan Yu, Xiaona Liu, Wanxia Shen, Shiping Zhu, Xiaochun Zhao. Temporal and spatial variations on accumulation of nomilin and limonin in the pummelos. Plant physiology and biochemistry : PPB. 2016 Sep; 106(?):23-9. doi: 10.1016/j.plaphy.2016.04.039. [PMID: 27135815]
  • Yeo Cho Yoon, Sung-Hee Kim, Min Jung Kim, Hye Jeong Yang, Mee-Ra Rhyu, Jae-Ho Park. Limonin, a Component of Dictamni Radicis Cortex, Inhibits Eugenol-Induced Calcium and cAMP Levels and PKA/CREB Signaling Pathway in Non-Neuronal 3T3-L1 Cells. Molecules (Basel, Switzerland). 2015 Dec; 20(12):22128-36. doi: 10.3390/molecules201219840. [PMID: 26690397]
  • Arabinda Das, Rickey Miller, Philip Lee, Chrysanthe Alyssa Holden, Scott M Lindhorst, Jerry Jaboin, William A Vandergrift, Naren L Banik, Pierre Giglio, Abhay K Varma, Jeffery J Raizer, Sunil J Patel. A novel component from citrus, ginger, and mushroom family exhibits antitumor activity on human meningioma cells through suppressing the Wnt/β-catenin signaling pathway. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine. 2015 Sep; 36(9):7027-34. doi: 10.1007/s13277-015-3388-0. [PMID: 25864108]
  • Taijun Yin, Guanyi Yang, Yong Ma, Beibei Xu, Ming Hu, Ming You, Song Gao. Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B). Journal of ethnopharmacology. 2015 Aug; 172(?):195-201. doi: 10.1016/j.jep.2015.06.019. [PMID: 26099633]
  • Xueqiang Pan, Manyuan Wang, Yanchuan Wu, Xuran Lu, Yawen Shang, Yongsong Xu, Yongsong Zhai, Jing Li, Zhaoxia Li, Muxin Gong. Identification of active ingredients in Wuzhuyu decoction improving migraine in mice by spectral efficiency association. Molecular medicine reports. 2015 Jul; 12(1):1524-34. doi: 10.3892/mmr.2015.3506. [PMID: 25815775]
  • Cuihua Liu, Fuhua Yan, Huijun Gao, Min He, Zhuang Wang, Yunjiang Cheng, Xiuxin Deng, Juan Xu. Features of citrus terpenoid production as revealed by carotenoid, limonoid and aroma profiles of two pummelos (Citrus maxima) with different flesh color. Journal of the science of food and agriculture. 2015 Jan; 95(1):111-9. doi: 10.1002/jsfa.6689. [PMID: 24723118]
  • Wei Ren, Yan Li, Ran Zuo, Hong-Jie Wang, Nan Si, Hai-Yu Zhao, Ling-Yu Han, Jian Yang, Bao-Lin Bian. Species-related difference between limonin and obacunone among five liver microsomes and zebrafish using ultra-high-performance liquid chromatography coupled with a LTQ-Orbitrap mass spectrometer. Rapid communications in mass spectrometry : RCM. 2014 Nov; 28(21):2292-300. doi: 10.1002/rcm.7026. [PMID: 25279742]
  • Nan Yang, Julie Wang, Changda Liu, Ying Song, Shuwei Zhang, Jiachen Zi, Jixun Zhan, Madhan Masilamani, Amanda Cox, Anna Nowak-Wegrzyn, Hugh Sampson, Xiu-Min Li. Berberine and limonin suppress IgE production by human B cells and peripheral blood mononuclear cells from food-allergic patients. Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology. 2014 Nov; 113(5):556-564.e4. doi: 10.1016/j.anai.2014.07.021. [PMID: 25155085]
  • Yu Xiang, Jinping Cao, Fenglei Luo, Dengliang Wang, Wei Chen, Xian Li, Chongde Sun, Kunsong Chen. Simultaneous purification of limonin, nomilin and isoobacunoic acid from pomelo fruit (Citrus grandis) segment membrane. Journal of food science. 2014 Oct; 79(10):C1956-63. doi: 10.1111/1750-3841.12581. [PMID: 25212475]
  • Elizabeth L Chin, Darya O Mishchuk, Andrew P Breksa, Carolyn M Slupsky. Metabolite signature of Candidatus Liberibacter asiaticus infection in two citrus varieties. Journal of agricultural and food chemistry. 2014 Jul; 62(28):6585-91. doi: 10.1021/jf5017434. [PMID: 24959841]
  • Shaojie Li, Zhuang Wang, Fan Ding, Da Sun, Zhaocheng Ma, Yunjiang Cheng, Juan Xu. Content changes of bitter compounds in 'Guoqing No.1' Satsuma mandarin (Citrus unshiu Marc.) during fruit development of consecutive 3 seasons. Food chemistry. 2014 Feb; 145(?):963-9. doi: 10.1016/j.foodchem.2013.09.040. [PMID: 24128570]
  • Xiaolong Tang, Zhifang Huang, Yan Chen, Yunhua Liu, Yuhong Liu, Junning Zhao, Jinhai Yi. Simultaneous determination of six bioactive compounds in Evodiae Fructus by high-performance liquid chromatography with diode array detection. Journal of chromatographic science. 2014 Feb; 52(2):149-56. doi: 10.1093/chromsci/bms261. [PMID: 23377650]
  • Pei Wang, Jianbo Sun, Enze Gao, Yunli Zhao, Wei Qu, Zhiguo Yu. Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jun; 928(?):44-51. doi: 10.1016/j.jchromb.2013.03.018. [PMID: 23611843]
  • Huarong Xu, Qing Li, Yidi Yin, Chunxiao Lv, Wanyang Sun, Bosai He, Ran Liu, Xiaohui Chen, Kaishun Bi. Simultaneous determination of three alkaloids, four ginsenosides and limonin in the plasma of normal and headache rats after oral administration of Wu-Zhu-Yu decoction by a novel ultra fast liquid chromatography-tandem mass spectrometry method: application to a comparative pharmacokinetics and ethological study. Journal of mass spectrometry : JMS. 2013 Apr; 48(4):519-32. doi: 10.1002/jms.3183. [PMID: 23584945]
  • Shi-jia Liu, Ling Zhou, Jun Zhang, Bo-yang Yu, Chang-yin Li, Zi-xiu Liu, Wen-zheng Ju. Determination of limonin in dog plasma by liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2013 Apr; 27(4):515-9. doi: 10.1002/bmc.2821. [PMID: 23018841]
  • Priyanka Chaudhary, G K Jayaprakasha, Ron Porat, Bhimanagouda S Patil. Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds. Food chemistry. 2012 Dec; 135(3):1667-75. doi: 10.1016/j.foodchem.2012.05.095. [PMID: 22953908]
  • Shijia Liu, Jun Zhang, Ling Zhou, Boyang Yu, Changyin Li, Zixiu Liu, Wenzheng Ju. Quantification of limonin in human urine using solid-phase extraction by LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Oct; 907(?):163-7. doi: 10.1016/j.jchromb.2012.08.038. [PMID: 22999474]
  • Ram M Uckoo, Guddadarangavvanahally K Jayaprakasha, V M Balasubramaniam, Bhimanagouda S Patil. Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques. Journal of food science. 2012 Sep; 77(9):C921-6. doi: 10.1111/j.1750-3841.2012.02865.x. [PMID: 22957912]
  • Zhi Long Liu, Qi Zhi Liu, Shu Shan Du, Zhi Wei Deng. Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae). Parasitology research. 2012 Sep; 111(3):991-6. doi: 10.1007/s00436-012-2923-9. [PMID: 22526296]
  • Anne M Slisz, Andrew P Breksa, Darya O Mishchuk, Greg McCollum, Carolyn M Slupsky. Metabolomic analysis of citrus infection by 'Candidatus Liberibacter' reveals insight into pathogenicity. Journal of proteome research. 2012 Aug; 11(8):4223-30. doi: 10.1021/pr300350x. [PMID: 22698301]
  • Ze Yun, Shuai Jin, Yuduan Ding, Zhuang Wang, Huijun Gao, Zhiyong Pan, Juan Xu, Yunjiang Cheng, Xiuxin Deng. Comparative transcriptomics and proteomics analysis of citrus fruit, to improve understanding of the effect of low temperature on maintaining fruit quality during lengthy post-harvest storage. Journal of experimental botany. 2012 May; 63(8):2873-93. doi: 10.1093/jxb/err390. [PMID: 22323274]
  • Hui-Ling Liao, Jacqueline K Burns. Gene expression in Citrus sinensis fruit tissues harvested from huanglongbing-infected trees: comparison with girdled fruit. Journal of experimental botany. 2012 May; 63(8):3307-19. doi: 10.1093/jxb/ers070. [PMID: 22407645]
  • Meenakshi Malik, Abhijit Ganguli, Moushumi Ghosh. Enhancement of bioconversion efficiency of limonin by Pseudmonas putida G7. International journal of food sciences and nutrition. 2012 Feb; 63(1):59-65. doi: 10.3109/09637486.2011.596823. [PMID: 21732728]
  • Yong-Tai Zhang, Zhe-Bin Huang, Su-Juan Zhang, Ji-Hui Zhao, Zhi Wang, Ying Liu, Nian-Ping Feng. In vitro cellular uptake of evodiamine and rutaecarpine using a microemulsion. International journal of nanomedicine. 2012; 7(?):2465-72. doi: 10.2147/ijn.s30616. [PMID: 22679361]
  • Md Sarfaraj Hussain, Sheeba Fareed, Saba Ansari, Md Akhlaquer Rahman, Iffat Zareen Ahmad, Mohd Saeed. Current approaches toward production of secondary plant metabolites. Journal of pharmacy & bioallied sciences. 2012 Jan; 4(1):10-20. doi: 10.4103/0975-7406.92725. [PMID: 22368394]
  • Eri Ono, Jun Inoue, Tsutomu Hashidume, Makoto Shimizu, Ryuichiro Sato. Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet. Biochemical and biophysical research communications. 2011 Jul; 410(3):677-81. doi: 10.1016/j.bbrc.2011.06.055. [PMID: 21693102]
  • Dalia Hamdan, Mahmoud Zaki El-Readi, Ahmad Tahrani, Florian Herrmann, Dorothea Kaufmann, Nawal Farrag, Assem El-Shazly, Michael Wink. Secondary metabolites of ponderosa lemon (Citrus pyriformis) and their antioxidant, anti-inflammatory, and cytotoxic activities. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2011 Jul; 66(7-8):385-93. doi: 10.1515/znc-2011-7-810. [PMID: 21950163]
  • Juanjuan Zhao, Xiao Han, Xu Zhao, Chao Wang, Qing Li, Xiaohui Chen, Kaishun Bi. A sensitive liquid chromatographic-mass spectrometric method for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma. Analytical and bioanalytical chemistry. 2011 Jul; 401(1):289-96. doi: 10.1007/s00216-011-5072-6. [PMID: 21573727]
  • Faisal Hafeez, Waseem Akram, Essam Abdel-Salam Shaalan. Mosquito larvicidal activity of citrus limonoids against Aedes albopictus. Parasitology research. 2011 Jul; 109(1):221-9. doi: 10.1007/s00436-010-2228-9. [PMID: 21212981]
  • Yu-feng Yuan, Zhan-hua Tao, Jun-xian Liu, Chang-hai Tian, Gui-wen Wang, Yong-qing Li. [Identification of Cortex Phellodendri by Fourier-transform infrared spectroscopy and principal component analysis]. Guang pu xue yu guang pu fen xi = Guang pu. 2011 May; 31(5):1258-61. doi: ". [PMID: 21800577]
  • Natália Cassettari de Carvalho, Maria Júlia Frydberg Corrêa-Angeloni, Daniela Dimer Leffa, Jeverson Moreira, Vanessa Nicolau, Patrícia de Aguiar Amaral, Angela Erna Rossatto, Vanessa Moraes de Andrade. Evaluation of the genotoxic and antigenotoxic potential of Melissa officinalis in mice. Genetics and molecular biology. 2011 Apr; 34(2):290-7. doi: 10.1590/s1415-47572011000200021. [PMID: 21734832]
  • Kotamballi N Chidambara Murthy, G K Jayaprakasha, Vinod Kumar, Keerti S Rathore, Bhimanagouda S Patil. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. Journal of agricultural and food chemistry. 2011 Mar; 59(6):2314-23. doi: 10.1021/jf104498p. [PMID: 21338095]
  • Zhifang Huang, Jinhai Yi, Yan Wu, Yunhua Liu, Yan Chen, Yuhong Liu. [Optimization of a HPLC determination method for Evodia rutaecarpa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Feb; 36(4):478-80. doi: 10.4268/cjcmm20110422. [PMID: 21598546]
  • Wen-Fei Chiou, Han-Chieh Ko, Bai-Luh Wei. Evodia rutaecarpa and Three Major Alkaloids Abrogate Influenza A Virus (H1N1)-Induced Chemokines Production and Cell Migration. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):750513. doi: 10.1093/ecam/nep238. [PMID: 21799692]
  • Yong-Tai Zhang, Ji-Hui Zhao, Su-Juan Zhang, Yang-Zi Zhong, Zhi Wang, Ying Liu, Feng Shi, Nian-Ping Feng. Enhanced transdermal delivery of evodiamine and rutaecarpine using microemulsion. International journal of nanomedicine. 2011; 6(?):2469-82. doi: 10.2147/ijn.s25258. [PMID: 22072882]
  • Yubo Li, Tiejun Zhang, Xiaolan Zhang, Haiyu Xu, Changxiao Liu. Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics. Journal of separation science. 2010 Nov; 33(21):3347-53. doi: 10.1002/jssc.201000426. [PMID: 21049522]
  • Jose L Perez, Guddarangavvanahally K Jayaprakasha, Adriana Cadena, Elvia Martinez, Hassan Ahmad, Bhimanagouda S Patil. In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids. BMC complementary and alternative medicine. 2010 Sep; 10(?):51. doi: 10.1186/1472-6882-10-51. [PMID: 20846448]
  • Jeong Seon Yoon, Hyekyung Yang, Seung Hyun Kim, Sang Hyun Sung, Young Choong Kim. Limonoids from Dictamnus dasycarpus protect against glutamate-induced toxicity in primary cultured rat cortical cells. Journal of molecular neuroscience : MN. 2010 Sep; 42(1):9-16. doi: 10.1007/s12031-010-9333-1. [PMID: 20155333]
  • Fangyuan Gong, Yan Shen, Qi Zhang, Yang Sun, Jiayu Tang, Feifei Tao, Qiang Xu. Obaculactone suppresses Th1 effector cell function through down-regulation of T-bet and prolongs skin graft survival in mice. Biochemical pharmacology. 2010 Jul; 80(2):218-25. doi: 10.1016/j.bcp.2010.03.028. [PMID: 20361943]
  • Tao Feng, Rui-Rui Wang, Xiang-Hai Cai, Yong-Tang Zheng, Xiao-Dong Luo. Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata. Chemical & pharmaceutical bulletin. 2010 Jul; 58(7):971-5. doi: 10.1248/cpb.58.971. [PMID: 20606349]
  • Muxin Gong, Yaxun Wang, Yafang Song, Zhimin Wang, Qiwei Zhang, Weihao Wang, Jingjing Zhu. [Everted intestinal sac method for quick finding absorption ingredients of Wuzhuyu decoction]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Jun; 35(11):1399-404. doi: . [PMID: 20822007]
  • Anne Plotto, Elizabeth Baldwin, Greg McCollum, John Manthey, Jan Narciso, Mike Irey. Effect of Liberibacter infection (huanglongbing or 'greening' disease) of citrus on orange juice flavor quality by sensory evaluation. Journal of food science. 2010 May; 75(4):S220-30. doi: 10.1111/j.1750-3841.2010.01580.x. [PMID: 20546425]
  • Leonardo Lucantoni, Rakiswendé S Yerbanga, Giulio Lupidi, Luciano Pasqualini, Fulvio Esposito, Annette Habluetzel. Transmission blocking activity of a standardized neem (Azadirachta indica) seed extract on the rodent malaria parasite Plasmodium berghei in its vector Anopheles stephensi. Malaria journal. 2010 Mar; 9(?):66. doi: 10.1186/1475-2875-9-66. [PMID: 20196858]
  • Lilibeth Dagulo, Michelle D Danyluk, Timothy M Spann, M Filomena Valim, Renée Goodrich-Schneider, Charles Sims, Russell Rouseff. Chemical characterization of orange juice from trees infected with citrus greening (Huanglongbing). Journal of food science. 2010 Mar; 75(2):C199-207. doi: 10.1111/j.1750-3841.2009.01495.x. [PMID: 20492226]
  • Elizabeth Baldwin, Anne Plotto, John Manthey, Greg McCollum, Jinhe Bai, Mike Irey, Randall Cameron, Gary Luzio. Effect of liberibacter infection (huanglongbing disease) of citrus on orange fruit physiology and fruit/fruit juice quality: chemical and physical analyses. Journal of agricultural and food chemistry. 2010 Jan; 58(2):1247-62. doi: 10.1021/jf9031958. [PMID: 20030384]
  • Jaiprakash R Patil, K N Chidambara Murthy, G K Jayaprakasha, Mahadev B Chetti, Bhimanagouda S Patil. Bioactive compounds from Mexican lime ( Citrus aurantifolia ) juice induce apoptosis in human pancreatic cells. Journal of agricultural and food chemistry. 2009 Nov; 57(22):10933-42. doi: 10.1021/jf901718u. [PMID: 19919125]
  • Yang Zhao, Zhangwan Li, Xin Zhou, Zongwei Cai, Xiaojian Gong, Chanyuan Zhou. Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection. Journal of pharmaceutical and biomedical analysis. 2008 Dec; 48(4):1230-6. doi: 10.1016/j.jpba.2008.08.035. [PMID: 18930617]
  • Zhao-Tang Ma, Xiu-Wei Yang. [Studies on ethyl acetate soluble constituents of Huanglian Jiedutang]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Sep; 33(18):2080-6. doi: . [PMID: 19160789]
  • Luping Qin, Ting Han, Qiaoyan Zhang, Dapeng Cao, Hua Nian, Khalid Rahman, Hanchen Zheng. Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula. Journal of ethnopharmacology. 2008 Jul; 118(2):271-9. doi: 10.1016/j.jep.2008.04.009. [PMID: 18501540]
  • Sung-Eun Lee, Mi-Ran Kim, Jeong-Han Kim, Gary R Takeoka, Tae-Wan Kim, Byeoung-Soo Park. Antimalarial activity of anthothecol derived from Khaya anthotheca (Meliaceae). Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Jun; 15(6-7):533-5. doi: 10.1016/j.phymed.2007.08.001. [PMID: 17913482]
  • Qiong-Feng Liao, Zhi-Yong Xie, Lei Zhang, Ya-Ting Deng, Chun Li, Cun-Fang Wei, Yuan Yao. [Mass spectrometric analysis of quinazoline alkaloid and limonin from Fructus Evodiae]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 May; 31(5):673-6. doi: ". [PMID: 18826141]
  • Jeong Seon Yoon, Sang Hyun Sung, Young Choong Kim. Neuroprotective limonoids of root bark of Dictamnus dasycarpus. Journal of natural products. 2008 Feb; 71(2):208-11. doi: 10.1021/np070588o. [PMID: 18198838]
  • Manuel Talon, Fred G Gmitter. Citrus genomics. International journal of plant genomics. 2008; 2008(?):528361. doi: 10.1155/2008/528361. [PMID: 18509486]
  • Anita Zamboni, Leone Minoia, Alberto Ferrarini, Giovanni Battista Tornielli, Elisa Zago, Massimo Delledonne, Mario Pezzotti. Molecular analysis of post-harvest withering in grape by AFLP transcriptional profiling. Journal of experimental botany. 2008; 59(15):4145-59. doi: 10.1093/jxb/ern256. [PMID: 19010774]
  • C Bayet, C Fazio, N Darbour, O Berger, I Raad, A Chaboud, C Dumontet, D Guilet. Modulation of P-glycoprotein activity by acridones and coumarins from Citrus sinensis. Phytotherapy research : PTR. 2007 Apr; 21(4):386-90. doi: 10.1002/ptr.2081. [PMID: 17236173]
  • Kranthi K Mandadi, Guddadarangavvanahally K Jayaprakasha, Narayan G Bhat, Bhimanagouda S Patil. Red Mexican grapefruit: a novel source for bioactive limonoids and their antioxidant activity. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 Mar; 62(3-4):179-88. doi: 10.1515/znc-2007-3-405. [PMID: 17542482]
  • Yong Deuk Min, Hak Cheol Kwon, Min Cheol Yang, Kyu Ha Lee, Sang Un Choi, Kang Ro Lee. Isolation of limonoids and alkaloids from Phellodendron amurense and their multidrug resistance (MDR) reversal activity. Archives of pharmacal research. 2007 Jan; 30(1):58-63. doi: 10.1007/bf02977779. [PMID: 17328243]
  • Jie Teng, Xiu-Wei Yang. A new limonoid from the fruits of Evodia rutaecarpa (Juss.) Benth. Die Pharmazie. 2006 Dec; 61(12):1038-40. doi: ". [PMID: 17283664]
  • Jun Yu, Deepak V Dandekar, Romeo T Toledo, Rakesh K Singh, Bhimanagouda S Patil. Supercritical fluid extraction of limonoid glucosides from grapefruit molasses. Journal of agricultural and food chemistry. 2006 Aug; 54(16):6041-5. doi: 10.1021/jf060382d. [PMID: 16881714]
  • Jairam Vanamala, Tety Leonardi, Bhimanagouda S Patil, Stella S Taddeo, Mary E Murphy, Leonard M Pike, Robert S Chapkin, Joanne R Lupton, Nancy D Turner. Suppression of colon carcinogenesis by bioactive compounds in grapefruit. Carcinogenesis. 2006 Jun; 27(6):1257-65. doi: 10.1093/carcin/bgi318. [PMID: 16387741]
  • Amit Roy, Shailendra Saraf. Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biological & pharmaceutical bulletin. 2006 Feb; 29(2):191-201. doi: 10.1248/bpb.29.191. [PMID: 16462017]
  • Yan Liang, Lin Xie, Xiao-Dong Liu, Tong Lu, Guang-Ji Wang, Yu-Zhu Hu. Determination of limonin in rat plasma by liquid chromatography-electrospray mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2005 Oct; 39(5):1031-5. doi: 10.1016/j.jpba.2005.06.012. [PMID: 16054321]
  • Y Liang, L Xie, X D Liu, Y Z Hu, T Lu, G J Wang. Gender differences in limonin pharmacokinetics in rats. European journal of drug metabolism and pharmacokinetics. 2005 Oct; 30(4):243-8. doi: 10.1007/bf03190627. [PMID: 16435568]
  • Ryoichi Inaba, Seyed Mohammad Mirbod, Haruo Sugiura. Effects of Maharishi Amrit Kalash 5 as an Ayurvedic herbal food supplement on immune functions in aged mice. BMC complementary and alternative medicine. 2005 Mar; 5(?):8. doi: 10.1186/1472-6882-5-8. [PMID: 15790423]
  • Hiroshi Iwata, Yasuhiro Tezuka, Shigetoshi Kadota, Akira Hiratsuka, Tadashi Watabe. Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract. Drug metabolism and pharmacokinetics. 2005 Feb; 20(1):34-45. doi: 10.2133/dmpk.20.34. [PMID: 15770073]
  • Min Yang, Guang Ji Wang, Su Jun Wang, Xiao Tian Li, Yu Ping Xu, Song Pei Wang, Jing De Xiang, Shang Ren Pan, Guo Xian Cao, Wen Cai Ye. Quantitative analysis of 23-hydroxybetulinic acid in mouse plasma using electrospray liquid chromatography/mass spectrometry. Rapid communications in mass spectrometry : RCM. 2005; 19(12):1619-23. doi: 10.1002/rcm.1961. [PMID: 15915449]
  • Qi-zhi Wang, Jing-yu Liang. [Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth]. Yao xue xue bao = Acta pharmaceutica Sinica. 2004 Aug; 39(8):605-8. doi: . [PMID: 15563061]
  • Lucia Battinelli, Fabio Mengoni, Miriam Lichtner, Gabriela Mazzanti, Antonina Saija, Claudio Maria Mastroianni, Vincenzo Vullo. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta medica. 2003 Oct; 69(10):910-3. doi: 10.1055/s-2003-45099. [PMID: 14648393]
  • Tian-Shung Wu, Meei-Yu Hsu, Ping-Chung Kuo, B Sreenivasulu, A G Damu, Chung-Ren Su, Chia-Ying Li, Hsien-Chang Chang. Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity. Journal of natural products. 2003 Sep; 66(9):1207-11. doi: 10.1021/np030034v. [PMID: 14510598]
  • Gary D Manners, Robert A Jacob, Andrew P Breksa, Thomas K Schoch, Shin Hasegawa. Bioavailability of citrus limonoids in humans. Journal of agricultural and food chemistry. 2003 Jul; 51(14):4156-61. doi: 10.1021/jf0300691. [PMID: 12822961]
  • Gary D Manners, Andrew P Breksa, Thomas K Schoch, Marlene B Hidalgo. Analysis of bitter limonoids in citrus juices by atmospheric pressure chemical ionization and electrospray ionization liquid chromatography-mass spectrometry. Journal of agricultural and food chemistry. 2003 Jun; 51(13):3709-14. doi: 10.1021/jf021124t. [PMID: 12797731]
  • Xue-mei Zhao, Xing-qian Ye, Yu-fang Xi, Da-yuan Zhu, Shan-hao Jiang. [Studies on chemical constituents in the peels of Citrus changshan-huyou (I)]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Mar; 28(3):237-9. doi: ". [PMID: 15015309]