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1180-71-8,MFCD00075922
Catalog No.:AA003936

1180-71-8 | Limonin

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50mg
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100mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003936
Chemical Name:
Limonin
CAS Number:
1180-71-8
Molecular Formula:
C26H30O8
Molecular Weight:
470.5116
MDL Number:
MFCD00075922
SMILES:
O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1cocc1)C)C)(C)C
Properties
Computed Properties
 
Complexity:
1010  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
8  
Rotatable Bond Count:
1  
XLogP3:
1.8  

Literature

Title: Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds.

Journal: Food chemistry 20121201

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Quantification of limonin in human urine using solid-phase extraction by LC-MS/MS.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20121015

Title: Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae).

Journal: Parasitology research 20120901

Title: Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.

Journal: Journal of food science 20120901

Title: Metabolomic analysis of citrus infection by 'Candidatus Liberibacter' reveals insight into pathogenicity.

Journal: Journal of proteome research 20120803

Title: Modeling of permeabilization process in Pseudomonas putida G7 for enhanced limonin bioconversion.

Journal: Applied microbiology and biotechnology 20120701

Title: 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: Journal of experimental botany 20120501

Title: Gene expression in Citrus sinensis fruit tissues harvested from huanglongbing-infected trees: comparison with girdled fruit.

Journal: Journal of experimental botany 20120501

Title: Enhancement of bioconversion efficiency of limonin by Pseudmonas putida G7.

Journal: International journal of food sciences and nutrition 20120201

Title: [Transport of limonin in rat intestine in situ and Caco-2 cells in vitro].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20120201

Title: Cancer chemoprevention by citrus pulp and juices containing high amounts of β-cryptoxanthin and hesperidin.

Journal: Journal of biomedicine & biotechnology 20120101

Title: Flavonoids Isolated from Korea Citrus aurantium L. Induce G2/M Phase Arrest and Apoptosis in Human Gastric Cancer AGS Cells.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Current approaches toward production of secondary plant metabolites.

Journal: Journal of pharmacy & bioallied sciences 20120101

Title: Secondary Metabolites from Plants Inhibiting ABC Transporters and Reversing Resistance of Cancer Cells and Microbes to Cytotoxic and Antimicrobial Agents.

Journal: Frontiers in microbiology 20120101

Title: In vitro cellular uptake of evodiamine and rutaecarpine using a microemulsion.

Journal: International journal of nanomedicine 20120101

Title: Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer.

Journal: Journal of nutrigenetics and nutrigenomics 20120101

Title: Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20111201

Title: Structure-function relationships of citrus limonoids on p38 MAP kinase activity in human aortic smooth muscle cells.

Journal: European journal of pharmacology 20111116

Title: Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities.

Journal: Journal of Asian natural products research 20111001

Title: Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet.

Journal: Biochemical and biophysical research communications 20110708

Title: Mosquito larvicidal activity of citrus limonoids against Aedes albopictus.

Journal: Parasitology research 20110701

Title: A sensitive liquid chromatographic-mass spectrometric method for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma.

Journal: Analytical and bioanalytical chemistry 20110701

Title: Juice blends--a way of utilization of under-utilized fruits, vegetables, and spices: a review.

Journal: Critical reviews in food science and nutrition 20110701

Title: [Identification of Cortex Phellodendri by Fourier-transform infrared spectroscopy and principal component analysis].

Journal: Guang pu xue yu guang pu fen xi = Guang pu 20110501

Title: Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis.

Journal: Journal of agricultural and food chemistry 20110323

Title: Antiviral activity of seed extract from Citrus bergamia towards human retroviruses.

Journal: Bioorganic & medicinal chemistry 20110315

Title: [Optimization of a HPLC determination method for Evodia rutaecarpa].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110201

Title: Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra.

Journal: Journal of separation science 20110101

Title: Different influences on tacrolimus pharmacokinetics by coadministrations of zhi ke and zhi shi in rats.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Anti-inflammatory and anti-infectious effects of Evodia rutaecarpa (Wuzhuyu) and its major bioactive components.

Journal: Chinese medicine 20110101

Title: Evaluation of the genotoxic and antigenotoxic potential of Melissa officinalis in mice.

Journal: Genetics and molecular biology 20110101

Title: Evodia rutaecarpa and Three Major Alkaloids Abrogate Influenza A Virus (H1N1)-Induced Chemokines Production and Cell Migration.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Regulation of apoptotic effects by erythrocarpine E, a cytotoxic limonoid from Chisocheton erythrocarpus in HSC-4 human oral cancer cells.

Journal: PloS one 20110101

Title: Secondary metabolites of ponderosa lemon (Citrus pyriformis) and their antioxidant, anti-inflammatory, and cytotoxic activities.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20110101

Title: Enhanced transdermal delivery of evodiamine and rutaecarpine using microemulsion.

Journal: International journal of nanomedicine 20110101

Title: Electronic noses and tongues: applications for the food and pharmaceutical industries.

Journal: Sensors (Basel, Switzerland) 20110101

Title: Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics.

Journal: Journal of separation science 20101101

Title: Limonoids from Dictamnus dasycarpus protect against glutamate-induced toxicity in primary cultured rat cortical cells.

Journal: Journal of molecular neuroscience : MN 20100901

Title: Obaculactone suppresses Th1 effector cell function through down-regulation of T-bet and prolongs skin graft survival in mice.

Journal: Biochemical pharmacology 20100715

Title: Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata.

Journal: Chemical & pharmaceutical bulletin 20100701

Title: [Everted intestinal sac method for quick finding absorption ingredients of Wuzhuyu decoction].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100601

Title: Effect of Liberibacter infection (huanglongbing or 'greening' disease) of citrus on orange juice flavor quality by sensory evaluation.

Journal: Journal of food science 20100501

Title: Chemical characterization of orange juice from trees infected with citrus greening (Huanglongbing).

Journal: Journal of food science 20100301

Title: Effect of liberibacter infection (huanglongbing disease) of citrus on orange fruit physiology and fruit/fruit juice quality: chemical and physical analyses.

Journal: Journal of agricultural and food chemistry 20100127

Title: Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines.

Journal: European journal of pharmacology 20100125

Title: Transmission blocking activity of a standardized neem (Azadirachta indica) seed extract on the rodent malaria parasite Plasmodium berghei in its vector Anopheles stephensi.

Journal: Malaria journal 20100101

Title: Determination of bioactive compounds in Cortex Phellodendri by high-performance liquid chromatography.

Journal: Journal of AOAC International 20100101

Title: In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids.

Journal: BMC complementary and alternative medicine 20100101

Title: Bioactive compounds from Mexican lime ( Citrus aurantifolia ) juice induce apoptosis in human pancreatic cells.

Journal: Journal of agricultural and food chemistry 20091125

Title: Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase.

Journal: Journal of agricultural and food chemistry 20090624

Title: [Studies on chemical constituents of Evodia rutaecarpa].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090101

Title: Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.

Journal: European journal of pharmacology 20081214

Title: Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection.

Journal: Journal of pharmaceutical and biomedical analysis 20081201

Title: Influence of electron-beam irradiation on bioactive compounds in grapefruits ( Citrus paradisi Macf.).

Journal: Journal of agricultural and food chemistry 20081126

Title: Oxidative burst inhibitory and cytotoxic indoloquinazoline and furoquinoline alkaloids from Oricia suaveolens.

Journal: Journal of natural products 20081101

Title: Molecular analysis of post-harvest withering in grape by AFLP transcriptional profiling.

Journal: Journal of experimental botany 20081101

Title: [Studies on ethyl acetate soluble constituents of Huanglian Jiedutang].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080901

Title: Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula.

Journal: Journal of ethnopharmacology 20080723

Title: Isolation and identification of the first C-17 limonin epimer, epilimonin.

Journal: Journal of agricultural and food chemistry 20080723

Title: Antimalarial activity of anthothecol derived from Khaya anthotheca (Meliaceae).

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20080601

Title: [Mass spectrometric analysis of quinazoline alkaloid and limonin from Fructus Evodiae].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080501

Title: Neuroprotective limonoids of root bark of Dictamnus dasycarpus.

Journal: Journal of natural products 20080201

Title: Flavonoid glycosides and limonoids from Citrus molasses.

Journal: Journal of natural medicines 20080101

Title: Citrus genomics.

Journal: International journal of plant genomics 20080101

Title: Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101

Title: A New coumarin from Citrus paradisi Macf.

Journal: Indian journal of pharmaceutical sciences 20080101

Title: Colorimetric method for the estimation of total limonoid aglycones and glucoside contents in citrus juices.

Journal: Journal of agricultural and food chemistry 20070627

Title: Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography.

Journal: Analytica chimica acta 20070508

Title: The debittering of navel orange juice using polymeric films.

Journal: Journal of food science 20070501

Title: Modulation of P-glycoprotein activity by acridones and coumarins from Citrus sinensis.

Journal: Phytotherapy research : PTR 20070401

Title: Isolation of limonoids and alkaloids from Phellodendron amurense and their multidrug resistance (MDR) reversal activity.

Journal: Archives of pharmacal research 20070101

Title: Red Mexican grapefruit: a novel source for bioactive limonoids and their antioxidant activity.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20070101

Title: A new limonoid from the fruits of Evodia rutaecarpa (Juss.) Benth.

Journal: Die Pharmazie 20061201

Title: Evidence of indigenous NAH plasmid of naphthalene degrading Pseudomonas putida PpG7 strain implicated in limonin degradation.

Journal: Journal of microbiology (Seoul, Korea) 20061001

Title: Supercritical fluid extraction of limonoid glucosides from grapefruit molasses.

Journal: Journal of agricultural and food chemistry 20060809

Title: Suppression of colon carcinogenesis by bioactive compounds in grapefruit.

Journal: Carcinogenesis 20060601

Title: Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside.

Journal: Journal of agricultural and food chemistry 20060531

Title: [Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20060401

Title: [Determination of bitter components in citrus juice by high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20060301

Title: Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom.

Journal: Biological & pharmaceutical bulletin 20060201

Title: Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells.

Journal: Nutrition and cancer 20060101

Title: Determination of limonin in rat plasma by liquid chromatography-electrospray mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20051004

Title: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.

Journal: Current drug metabolism 20051001

Title: Antioxidant activity of citrus limonoids, flavonoids, and coumarins.

Journal: Journal of agricultural and food chemistry 20050323

Title: Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract.

Journal: Drug metabolism and pharmacokinetics 20050201

Title: Effects of Maharishi Amrit Kalash 5 as an Ayurvedic herbal food supplement on immune functions in aged mice.

Journal: BMC complementary and alternative medicine 20050101

Title: Quantitative analysis of 23-hydroxybetulinic acid in mouse plasma using electrospray liquid chromatography/mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20050101

Title: Gender differences in limonin pharmacokinetics in rats.

Journal: European journal of drug metabolism and pharmacokinetics 20050101

Title: [Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20040801

Title: Determination of limonin D-ring lactone hydrolase activity by solid phase extraction with indirect fluorescence detection.

Journal: Journal of agricultural and food chemistry 20040616

Title: Characterization of limonin glucoside metabolites from human prostate cell culture medium using high-performance liquid chromatography/electrospray ionization mass spectrometry and tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20040101

Title: Mass spectrometry and tandem mass spectrometry of citrus limonoids.

Journal: Analytical chemistry 20031015

Title: Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells.

Journal: Planta medica 20031001

Title: Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity.

Journal: Journal of natural products 20030901

Title: Bioavailability of citrus limonoids in humans.

Journal: Journal of agricultural and food chemistry 20030702

Title: Analysis of bitter limonoids in citrus juices by atmospheric pressure chemical ionization and electrospray ionization liquid chromatography-mass spectrometry.

Journal: Journal of agricultural and food chemistry 20030618

Title: [Studies on chemical constituents in the peels of Citrus changshan-huyou (I)].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20030301

Title: Limonoids from Citrus reticulata.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101

Title: Electron ionization mass spectrometry of citrus limonoids.

Journal: Rapid communications in mass spectrometry : RCM 20030101

Title: Constituents of the fruits and leaves of Euodia daniellii.

Journal: Archives of pharmacal research 20021201

Title: Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study.

Journal: Journal of agricultural and food chemistry 20021106

Title: Apotirucallane triterpenoids from Luvunga sarmentosa (Rutaceae).

Journal: Phytochemistry 20020801

Title: Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts.

Journal: Journal of agricultural and food chemistry 20011201

Title: Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue.

Journal: Journal of agricultural and food chemistry 20010901

Title: Effect of compound sequence on bitterness enhancement.

Journal: Chemical senses 20010501

Title: Limonoids from Citrus sudachi.

Journal: Chemical & pharmaceutical bulletin 20010501

Title: Inhibition of azoxymethane-induced colon carcinogenesis in male F344 rats by the citrus limonoids obacunone and limonin.

Journal: Carcinogenesis 20010101

Title: Limonoids from the endemic Brazilian species Raulinoa echinata.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20010101

Title: Differential inhibition of human cancer cell proliferation by citrus limonoids.

Journal: Nutrition and cancer 20010101

Title: The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan.

Journal: Biological & pharmaceutical bulletin 19981201

Title: Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes.

Journal: Biochemical pharmacology 19910601

Title: Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Journal: Journal of natural products 19910101

Title: Han YL, Yu HL, Li D, et al. Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro. Toxicol In Vitro. 2011 Dec;25(8):1828-33.

Title: Kotamballi N. Chidambara Murthy, Jayaprakasha, Vinod Kumar, et al. Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis. J. Agric. Food Chem., 2011, 59 (6):2314-2323.

Title: Mahmoud Zaki El-Readi, Dalia Hamdana, Nawal Farrag, et al. Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines. European Journal of Pharmacology. 2010,626 (2-3): 139-145.

Title: Battinelli L, Mengoni F, Lichtner M, et al. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta Med. 2003 Oct;69(10):910-3.

Title: Tanaka T, Kohno H, Tsukio Y, et al. Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. Biofactors. 2000;13(1-4):213-8.

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Tags:1180-71-8 Molecular Formula|1180-71-8 MDL|1180-71-8 SMILES|1180-71-8 Limonin