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limonin
obaculactone

Supplier Sponsors

CAS Number: 1180-71-8Picture of molecule3D/inchi
Other(deleted CASRN):1392-24-1
FDA UNII: L0F260866S
MDL:MFCD00075922
XlogP3-AA:1.80 (est)
Molecular Weight:470.51870000
Formula:C26 H30 O8
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 298.00 °C. @ 760.00 mm Hg
Boiling Point: 668.36 °C. @ 760.00 mm Hg (est)
Flash Point: 676.00 °F. TCC ( 358.00 °C. ) (est)
logP (o/w): 0.474 (est)
Soluble in:
 water, 270.2 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Evodine 98%
BOC Sciences
For experimental / research use only.
Limonin >98%
Odor: characteristic
Use: Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.
Changsha Organic Herb
Limonin
Glentham Life Sciences
Limonin
Santa Cruz Biotechnology
For experimental / research use only.
Limonin
Sigma-Aldrich: Sigma
For experimental / research use only.
Limonin from citrus seeds, >90% (HPLC)
sds
TCI AMERICA
For experimental / research use only.
Limonin >95.0%(HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for limonin usage levels up to:
 not for fragrance use.
 
Recommendation for limonin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65071
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0001180718
RTECS:RR1122000 for cas# 1180-71-8
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):65071
Pubchem (sid):135021811
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C03514
HMDB (The Human Metabolome Database):HMDB35921
FooDB:FDB014715
Export Tariff Code:2932.20.4500
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 lemon fruit
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 lemon seed
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 mandarin pericarp
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 mandarin seed
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 orange bark
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 orange branches
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 orange fruit
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 orange fruit juice
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 orange root
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 orange seed
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 orange twig
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Synonyms:
 citrolimonin
 dictamnolactone
7,16-dioxo-7,16-dideoxylimondiol
 evodin
 limonine
 limonoic acid, di-delta-lactone
 obaculactone
 

Articles:

PubMed:[Study on pharmacological ingredients of wuzhuyu tang treating migraine by correlating absorption ingredients in everted intestinal sac and pharmacodynamics].
PubMed:Features of citrus terpenoid production as revealed by carotenoid, limonoid and aroma profiles of two pummelos (Citrus maxima) with different flesh color.
PubMed:Synthesis and pharmacological evaluation of novel limonin derivatives as anti-inflammatory and analgesic agents with high water solubility.
PubMed:New limonoids from Coptidis Rhizoma-Euodiae Fructus couple.
PubMed:Evaluation of Physiological Activities of the Citron (Citrus junos Sieb. ex TANAKA) Seed Extracts.
PubMed:Hepatoprotective effect of limonin, a natural limonoid from the seed of Citrus aurantium var. bigaradia, on D-galactosamine-induced liver injury in rats.
PubMed:[Analysis on component difference in Citrus reticulata before and after being processed with salt by UPLC-Q-TOF/MS].
PubMed:An overview on chemical aspects and potential health benefits of limonoids and their derivatives.
PubMed:Content changes of bitter compounds in 'Guoqing No.1' Satsuma mandarin (Citrus unshiu Marc.) during fruit development of consecutive 3 seasons.
PubMed:[Determination of obacunone and obaculactone in different processing products of Phellodendri amurensis cortex].
PubMed:Limonoid constituents of Euodia rutaecarpa var. bodinieri and their inhibition on NO production in lipopolysaccharide-activated RAW264.7 macrophages.
PubMed:Simultaneous Quantification of Limonin, Two Indolequinazoline Alkaloids, and Four Quinolone Alkaloids in Evodia rutaecarpa (Juss.) Benth by HPLC-DAD Method.
PubMed:Influence of limonin on Wnt signalling molecule in HepG2 cell lines.
PubMed: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.
PubMed:[One new chroman glycoside derivative from unmatured fruits of Citrus aurantium].
PubMed: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.
PubMed:Citrus limonoids and curcumin additively inhibit human colon cancer cells.
PubMed:Identification of novel dietary phytochemicals inhibiting the efflux transporter breast cancer resistance protein (BCRP/ABCG2).
PubMed:Larvicidal Activity of Citrus Limonoids against Aedes albopictus Larvae.
PubMed:Simultaneous determination of six bioactive compounds in Evodiae Fructus by high-performance liquid chromatography with diode array detection.
PubMed:Limonoids and their anti-proliferative and anti-aromatase properties in human breast cancer cells.
PubMed:Determination of limonin in dog plasma by liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study.
PubMed:Quantification of limonin in human urine using solid-phase extraction by LC-MS/MS.
PubMed:Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.
PubMed:Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds.
PubMed:Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer.
PubMed:Metabolomic analysis of citrus infection by 'Candidatus Liberibacter' reveals insight into pathogenicity.
PubMed:Modeling of permeabilization process in Pseudomonas putida G7 for enhanced limonin bioconversion.
PubMed:Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae).
PubMed:[Transport of limonin in rat intestine in situ and Caco-2 cells in vitro].
PubMed: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.
PubMed:Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro.
PubMed:Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities.
PubMed:Secondary metabolites of ponderosa lemon (Citrus pyriformis) and their antioxidant, anti-inflammatory, and cytotoxic activities.
PubMed:Juice blends--a way of utilization of under-utilized fruits, vegetables, and spices: a review.
PubMed:Structure-function relationships of citrus limonoids on p38 MAP kinase activity in human aortic smooth muscle cells.
PubMed:Chemical composition and biological activity of Citrus jambhiri Lush.
PubMed:Enhancement of bioconversion efficiency of limonin by Pseudmonas putida G7.
PubMed:Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet.
PubMed:[Optimization of a HPLC determination method for Evodia rutaecarpa].
PubMed:A sensitive liquid chromatographic-mass spectrometric method for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma.
PubMed:Effect of juice extraction methods and processing temperature-time on juice quality of Nagpur mandarin (Citrus reticulata Blanco) during storage.
PubMed:Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis.
PubMed:Antiviral activity of seed extract from Citrus bergamia towards human retroviruses.
PubMed:Elevation, rootstock, and soil depth affect the nutritional quality of mandarin oranges.
PubMed:Mosquito larvicidal activity of citrus limonoids against Aedes albopictus.
PubMed:Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra.
PubMed:Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics.
PubMed:[Everted intestinal sac method for quick finding absorption ingredients of Wuzhuyu decoction].
PubMed:Determination of bioactive compounds in Cortex Phellodendri by high-performance liquid chromatography.
PubMed:Effect of Liberibacter infection (huanglongbing or "greening" disease) of citrus on orange juice flavor quality by sensory evaluation.
PubMed:Apigenin and naringenin suppress colon carcinogenesis through the aberrant crypt stage in azoxymethane-treated rats.
PubMed:Chemical characterization of orange juice from trees infected with citrus greening (Huanglongbing).
PubMed:Obaculactone suppresses Th1 effector cell function through down-regulation of T-bet and prolongs skin graft survival in mice.
PubMed:Limonoids from Dictamnus dasycarpus protect against glutamate-induced toxicity in primary cultured rat cortical cells.
PubMed:Effect of liberibacter infection (huanglongbing disease) of citrus on orange fruit physiology and fruit/fruit juice quality: chemical and physical analyses.
PubMed:Bioactive compounds from Mexican lime ( Citrus aurantifolia ) juice induce apoptosis in human pancreatic cells.
PubMed:Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines.
PubMed:Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase.
PubMed:[Studies on chemical constituents of Evodia rutaecarpa].
PubMed:Dietary curcumin and limonin suppress CD4+ T-cell proliferation and interleukin-2 production in mice.
PubMed:[Studies on ethyl acetate soluble constituents of Huanglian Jiedutang].
PubMed:Influence of electron-beam irradiation on bioactive compounds in grapefruits ( Citrus paradisi Macf.).
PubMed:Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
PubMed:Citrus bioactive compounds improve bone quality and plasma antioxidant activity in orchidectomized rats.
PubMed:Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection.
PubMed:[Mass spectrometric analysis of quinazoline alkaloid and limonin from Fructus Evodiae].
PubMed:A New coumarin from Citrus paradisi Macf.
PubMed:Isolation and identification of the first C-17 limonin epimer, epilimonin.
PubMed:Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy.
PubMed:Flavonoid glycosides and limonoids from Citrus molasses.
PubMed:Neuroprotective limonoids of root bark of Dictamnus dasycarpus.
PubMed:The debittering of navel orange juice using polymeric films.
PubMed:Antimalarial activity of anthothecol derived from Khaya anthotheca (Meliaceae).
PubMed:Colorimetric method for the estimation of total limonoid aglycones and glucoside contents in citrus juices.
PubMed:Red Mexican grapefruit: a novel source for bioactive limonoids and their antioxidant activity.
PubMed:Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography.
PubMed:Isolation of limonoids and alkaloids from Phellodendron amurense and their multidrug resistance (MDR) reversal activity.
PubMed:A new limonoid from the fruits of Evodia rutaecarpa (Juss.) Benth.
PubMed:Modulation of P-glycoprotein activity by acridones and coumarins from Citrus sinensis.
PubMed:Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells.
PubMed:Evidence of indigenous NAH plasmid of naphthalene degrading Pseudomonas putida PpG7 strain implicated in limonin degradation.
PubMed:An improved HPLC method for the analysis of citrus limonoids in culture media.
PubMed:Supercritical fluid extraction of limonoid glucosides from grapefruit molasses.
PubMed:[Determination of bitter components in citrus juice by high performance liquid chromatography].
PubMed:Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside.
PubMed:Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom.
PubMed:Gender differences in limonin pharmacokinetics in rats.
PubMed:[Studies on chemical constituents in bark of dictamnus dasycarpus].
PubMed:Suppression of colon carcinogenesis by bioactive compounds in grapefruit.
PubMed:Determination of limonin in rat plasma by liquid chromatography-electrospray mass spectrometry.
PubMed:Quantitative analysis of 23-hydroxybetulinic acid in mouse plasma using electrospray liquid chromatography/mass spectrometry.
PubMed:Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract.
PubMed:Antioxidant activity of citrus limonoids, flavonoids, and coumarins.
PubMed:Characterization of limonin glucoside metabolites from human prostate cell culture medium using high-performance liquid chromatography/electrospray ionization mass spectrometry and tandem mass spectrometry.
PubMed:[Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth].
PubMed:Determination of limonin D-ring lactone hydrolase activity by solid phase extraction with indirect fluorescence detection.
PubMed:[Studies on chemical constituents in the peels of Citrus changshan-huyou (I)].
PubMed:Mass spectrometry and tandem mass spectrometry of citrus limonoids.
PubMed:Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells.
PubMed:Electron ionization mass spectrometry of citrus limonoids.
PubMed:Bioavailability of citrus limonoids in humans.
PubMed:Analysis of bitter limonoids in citrus juices by atmospheric pressure chemical ionization and electrospray ionization liquid chromatography-mass spectrometry.
PubMed:Limonoids from Citrus reticulata.
PubMed:[Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth. var. officinalis (Dode) Huang].
PubMed:Constituents of the fruits and leaves of Euodia daniellii.
PubMed:Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study.
PubMed:Apotirucallane triterpenoids from Luvunga sarmentosa (Rutaceae).
PubMed:Differential inhibition of human cancer cell proliferation by citrus limonoids.
PubMed:Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts.
PubMed:Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue.
PubMed:Limonoids from the endemic Brazilian species Raulinoa echinata.
PubMed:Limonoids from Citrus sudachi.
PubMed:Effect of compound sequence on bitterness enhancement.
PubMed:Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats.
PubMed:Inhibition of azoxymethane-induced colon carcinogenesis in male F344 rats by the citrus limonoids obacunone and limonin.
PubMed:Determination of Key Flavor Components in Methylene Chloride Extracts from Processed Grapefruit Juice.
PubMed:Calorimetric evidence of differentiated transport of limonin and nomilin through biomembranes.
PubMed:Inhibition of azoxymethane-induced colon cancer by orange juice.
PubMed:Antifungal activity of some tetranortriterpenoids.
PubMed:Molecular cloning and characterization of a novel gene encoding limonoid UDP-glucosyltransferase in Citrus.
PubMed:The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan.
PubMed:Antinociceptive and anti-inflammatory activities of limonin isolated from the fruits of Evodia rutaecarpa var. bodinieri.
PubMed:Grapefruit component interacting with rat and human P450 CYP3A: possible involvement of non-flavonoid components in drug interaction.
PubMed:Limonoids from Citrus reticulata and their moult inhibiting activity in mosquito Culex quinquefasciatus larvae.
PubMed:Antinociceptive activities of 70% methanol extract of evodiae fructus (fruit of Evodia rutaecarpa var. bodinieri) and its alkaloidal components.
PubMed:Limonoate dehydrogenase from Arthrobacter globiformis: the native enzyme and its N-terminal sequence.
PubMed:Studies on the constituents of edible and medicinal plants. III. Effects of seven limonoids on the sleeping time induced in mice by anesthetics.
PubMed:[Limonoids in Phellodendron amurense (Kihada)].
PubMed:Meliaceae and rutaceae limonoids as termite antifeedants evaluated usingReticulitermes speratus kolbe (Isoptera: Rhinotermitidae).
PubMed:Inhibition of hamster buccal pouch carcinogenesis by limonin 17-beta-D-glucopyranoside.
PubMed:Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes.
PubMed:Quantitative analysis of limonin in grapefruit juice using an enzyme-linked immunoassay: interlaboratory study.
PubMed:Isolation of limonin and obacunone from phellodendri cortex shorten the sleeping time induced in mice by alpha-chloralose-urethane.
PubMed:The effect of citrus limonoids on hamster buccal pouch carcinogenesis.
PubMed:Determination of limonin in grapefruit juice and other citrus juices by high-performance liquid chromatography.
PubMed:Inhibition of benzo[a]pyrene-induced forestomach neoplasia in mice by citrus limonoids.
PubMed:Quantitative determination of limonin in citrus juices by HPLC using computerized solvent optimization.
PubMed:Competitive solid phase enzyme-linked immunoassay for the quantification of limonin in citrus.
PubMed:The structure of amoorastatone and the cytotoxic limonoid 12-hydroxyamoorastatin.
PubMed:Metabolism of limonoids. Limonin D-ring lactone hydrolase activity in Pseudomonas.
PubMed:[Steroids and sexual hormones. Synthetic experiments in the limonin series lV. A new Westphalen-Lettré rearrangement in the 4,4-dimethyl-steroid series].
PubMed:[Synthetic experiments in the limonin-series III. Stereospecific alkoxy-and dialkoxy-alkylation of 19-hydroxy-testosterone acetate].
PubMed:A limonin-degrading enzyme in citrus albedo.
PubMed:Chemical assay of limonin, the bitter principle of oranges.
PubMed:[PONCIRUS TRIFOLIATA AND CITRUS MEYERI--NEW SOURCES OF LIMONIN].
PubMed:Some observations on the structure of limonin.
 
Notes:
responsible for the bitterness of citrus fruit products. Isol. from oranges and other citrus fruits (Citrus spp.). Limonin is a limonoid, and a bitter, white, crystalline substance found in orange and lemon seeds. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.
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