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Limonin

CAS No.:
1180-71-8
Catalog Number:
AG00395Y
Molecular Formula:
C26H30O8
Molecular Weight:
470.5116
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25mg
98%(HPLC)
In Stock USA
United States
$54
- +
50mg
98%(HPLC)
In Stock USA
United States
$82
- +
100mg
98%(HPLC)
In Stock USA
United States
$139
- +
500mg
98%(HPLC)
In Stock USA
United States
$519
- +
1g
98%(HPLC)
In Stock USA
United States
$832
- +
Product Description
Catalog Number:
AG00395Y
Chemical Name:
Limonin
CAS Number:
1180-71-8
Molecular Formula:
C26H30O8
Molecular Weight:
470.5116
MDL Number:
MFCD00075922
IUPAC Name:
(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
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
InChI Key:
KBDSLGBFQAGHBE-MSGMIQHVSA-N
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
UNII:
L0F260866S
Properties
Complexity:
1010  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
470.194g/mol
Formal Charge:
0
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
470.518g/mol
Monoisotopic Mass:
470.194g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
105A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8  
Literature
Title Journal
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Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
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 20121015
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Modeling of permeabilization process in Pseudomonas putida G7 for enhanced limonin bioconversion. Applied microbiology and biotechnology 20120701
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Gene expression in Citrus sinensis fruit tissues harvested from huanglongbing-infected trees: comparison with girdled fruit. Journal of experimental botany 20120501
Enhancement of bioconversion efficiency of limonin by Pseudmonas putida G7. International journal of food sciences and nutrition 20120201
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In vitro cellular uptake of evodiamine and rutaecarpine using a microemulsion. International journal of nanomedicine 20120101
Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer. Journal of nutrigenetics and nutrigenomics 20120101
Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro. Toxicology in vitro : an international journal published in association with BIBRA 20111201
Structure-function relationships of citrus limonoids on p38 MAP kinase activity in human aortic smooth muscle cells. European journal of pharmacology 20111116
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Mosquito larvicidal activity of citrus limonoids against Aedes albopictus. Parasitology research 20110701
A sensitive liquid chromatographic-mass spectrometric method for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma. Analytical and bioanalytical chemistry 20110701
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Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. Journal of agricultural and food chemistry 20110323
Antiviral activity of seed extract from Citrus bergamia towards human retroviruses. Bioorganic & medicinal chemistry 20110315
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Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra. Journal of separation science 20110101
Different influences on tacrolimus pharmacokinetics by coadministrations of zhi ke and zhi shi in rats. Evidence-based complementary and alternative medicine : eCAM 20110101
Anti-inflammatory and anti-infectious effects of Evodia rutaecarpa (Wuzhuyu) and its major bioactive components. Chinese medicine 20110101
Evaluation of the genotoxic and antigenotoxic potential of Melissa officinalis in mice. Genetics and molecular biology 20110101
Evodia rutaecarpa and Three Major Alkaloids Abrogate Influenza A Virus (H1N1)-Induced Chemokines Production and Cell Migration. Evidence-based complementary and alternative medicine : eCAM 20110101
Regulation of apoptotic effects by erythrocarpine E, a cytotoxic limonoid from Chisocheton erythrocarpus in HSC-4 human oral cancer cells. PloS one 20110101
Secondary metabolites of ponderosa lemon (Citrus pyriformis) and their antioxidant, anti-inflammatory, and cytotoxic activities. Zeitschrift fur Naturforschung. C, Journal of biosciences 20110101
Enhanced transdermal delivery of evodiamine and rutaecarpine using microemulsion. International journal of nanomedicine 20110101
Electronic noses and tongues: applications for the food and pharmaceutical industries. Sensors (Basel, Switzerland) 20110101
Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics. Journal of separation science 20101101
Limonoids from Dictamnus dasycarpus protect against glutamate-induced toxicity in primary cultured rat cortical cells. Journal of molecular neuroscience : MN 20100901
Obaculactone suppresses Th1 effector cell function through down-regulation of T-bet and prolongs skin graft survival in mice. Biochemical pharmacology 20100715
Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata. Chemical & pharmaceutical bulletin 20100701
[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 20100601
Effect of Liberibacter infection (huanglongbing or 'greening' disease) of citrus on orange juice flavor quality by sensory evaluation. Journal of food science 20100501
Chemical characterization of orange juice from trees infected with citrus greening (Huanglongbing). Journal of food science 20100301
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 20100127
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 20100125
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 20100101
Determination of bioactive compounds in Cortex Phellodendri by high-performance liquid chromatography. Journal of AOAC International 20100101
In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids. BMC complementary and alternative medicine 20100101
Bioactive compounds from Mexican lime ( Citrus aurantifolia ) juice induce apoptosis in human pancreatic cells. Journal of agricultural and food chemistry 20091125
Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase. Journal of agricultural and food chemistry 20090624
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Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection. Journal of pharmaceutical and biomedical analysis 20081201
Influence of electron-beam irradiation on bioactive compounds in grapefruits ( Citrus paradisi Macf.). Journal of agricultural and food chemistry 20081126
Oxidative burst inhibitory and cytotoxic indoloquinazoline and furoquinoline alkaloids from Oricia suaveolens. Journal of natural products 20081101
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Isolation and identification of the first C-17 limonin epimer, epilimonin. Journal of agricultural and food chemistry 20080723
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[Mass spectrometric analysis of quinazoline alkaloid and limonin from Fructus Evodiae]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080501
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Evidence of indigenous NAH plasmid of naphthalene degrading Pseudomonas putida PpG7 strain implicated in limonin degradation. Journal of microbiology (Seoul, Korea) 20061001
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Determination of limonin D-ring lactone hydrolase activity by solid phase extraction with indirect fluorescence detection. Journal of agricultural and food chemistry 20040616
Characterization of limonin glucoside metabolites from human prostate cell culture medium using high-performance liquid chromatography/electrospray ionization mass spectrometry and tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20040101
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Properties