tangeretin
2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
 
Notes:
from citrus plants; inhibits invasion of mo4 mouse cells into embryonic chick heart in vitro. Isol. from tangerine peel and Fortunella japonica (round kumquat). Potential nutriceutical
  • O'Laughlin Industries
    • O'Laughlin Industries Inc.
      Manufacturer of Aroma
      Leading the Flavor and Fragrance Industry since 1980.
      O'Laughlin was established in 1980 by its owner and chief executive Michael O'Laughlin, when he moved to Beijing, China and established a small office. Since then it has grown to be a world class producer of chemicals, with significant production facilities in China, and distribution and sales in all major world markets.
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      774-7141 Tangeretin 70
       
  • TCI AMERICA
    • TCI AMERICA
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      We continuously strive to advance our technology.
      Tokyo Chemical Industry Co., Ltd. (TCI) is a leading worldwide manufacturer of specialty organic chemicals founded in 1946. TCI provides organic laboratory chemicals as well as pharmaceutical, cosmetic and functional materials. More than 60 years of synthesis experience and multi-purpose plants enable TCI to offer more than 27,000 products as well as custom synthesis. TCI established overseas facilities in North America, Europe, China and India to serve customers worldwide.
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      Product(s):
      T2708 Tangeretin >96.0%(HPLC)
       
Synonyms   Articles   Notes   Search
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one (Click)
CAS Number: 481-53-8Picture of molecule
ECHA EINECS - REACH Pre-Reg: 207-570-1
FDA UNII: I4TLA1DLX6
Nikkaji Web: J12.348J
Beilstein Number: 0351695
MDL: MFCD00017438
XlogP3-AA: 3.00 (est)
Molecular Weight: 372.37380000
Formula: C20 H20 O7
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants, skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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US Patents: Search
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PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 154.00 to  155.00 °C. @ 760.00 mm Hg
Boiling Point: 565.00 to  566.00 °C. @ 760.00 mm Hg (est)
Flash Point: 479.00 °F. TCC ( 248.40 °C. ) (est)
logP (o/w): 1.788 (est)
Soluble in:
 alcohol
 ethyl acetate
 water, 8.701 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
skin conditioning
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Suppliers:
BOC Sciences
For experimental / research use only.
Tangeretin >98%
ExtraSynthese
For experimental / research use only.
Tangeretin (HPLC) ≥95%
O'Laughlin Industries
Tangeretin 70
Santa Cruz Biotechnology
For experimental / research use only.
Tangeretin
Sigma-Aldrich: Sigma
For experimental / research use only.
Tangeretin ≥95% (HPLC)
TCI AMERICA
For experimental / research use only.
Tangeretin >96.0%(HPLC)
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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:
intraperitoneal-rat LD50  > 1000 mg/kg
Advances in Teratology. Vol. 3, Pg. 181, 1968.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants, skin conditioning
Recommendation for tangeretin usage levels up to:
 not for fragrance use.
 
Recommendation for tangeretin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 68077
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
Chemidplus: 0000481538
RTECS: DJ3102725 for cas# 481-53-8
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References:
 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 68077
Pubchem (sid): 135023454
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10190
HMDB (The Human Metabolome Database): HMDB30539
FooDB: FDB002412
Export Tariff Code: 2932.99.7000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 bay laurel
Search Trop  Picture
 fortunella japonica
Search Trop  Picture
 lemon pericarp
Search Trop  Picture
 mandarin fruit
Search Trop  Picture
 mandarin pericarp
Search Trop  Picture
 orange fruit
Search Trop  Picture
 orange fruit juice
Search Trop  Picture
 orange pericarp
Search Trop  Picture
 tangerine peel
Search Trop  Picture
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Synonyms:
2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
4',5,6,7,8-pentamethoxyflavone
5,6,7,8,4'-pentamethoxyflavone
 ponkanetin
 tangeritin
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms   Articles   Notes   Search   Top
Articles:
PubMed: Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.
PubMed: Citrus flavonoids and lipid metabolism.
PubMed: Antioxidant activity and effective compounds of immature calamondin peel.
PubMed: Chemical markers of shiikuwasha juice adulterated with calamondin juice.
PubMed: Protective effects of sweet orange (Citrus sinensis) peel and their bioactive compounds on oxidative stress.
PubMed: Anticancer effects of traditional Chinese herbs with phlegm-eliminating properties - An overview.
PubMed: Tangeretin enhances radiosensitivity and inhibits the radiation-induced epithelial-mesenchymal transition of gastric cancer cells.
PubMed: Viscoelastic Emulsion Improved the Bioaccessibility and Oral Bioavailability of Crystalline Compound: A Mechanistic Study Using in Vitro and in Vivo Models.
PubMed: Tangeretin triggers melanogenesis through the activation of melanogenic signaling proteins and sustained extracellular signal- regulated kinase in B16/F10 murine melanoma cells.
PubMed: Antioxidant, DNA protective efficacy and HPLC analysis of Annona muricata (soursop) extracts.
PubMed: Quality evaluation and pattern recognition analyses of marker compounds from five medicinal drugs of Rutaceae family by HPLC/PDA.
PubMed: Selecting bioactive phenolic compounds as potential agents to inhibit proliferation and VEGF expression in human ovarian cancer cells.
PubMed: Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
PubMed: Huanglongbing modifies quality components and flavonoid content of 'Valencia' oranges.
PubMed: Functional analysis of unfermented and fermented citrus peels and physical properties of citrus peel-added doughs for bread making.
PubMed: Stimulation effect of wide type CFTR chloride channel by the naturally occurring flavonoid tangeretin.
PubMed: Antitumor efficacy of tangeretin by targeting the oxidative stress mediated on 7,12-dimethylbenz(a) anthracene-induced proliferative breast cancer in Sprague-Dawley rats.
PubMed: Co-delivery of natural metabolic inhibitors in a self-microemulsifying drug delivery system for improved oral bioavailability of curcumin.
PubMed: Ingredients in fruit juices interact with dasatinib through inhibition of BCRP: a new mechanism of beverage-drug interaction.
PubMed: Chemical fingerprint and metabolic profile analysis of Citrus reticulate 'Chachi' decoction by HPLC-PDA-IT-MS(n) and HPLC-Quadrupole-Orbitrap-MS method.
PubMed: Tangeretin, a citrus pentamethoxyflavone, exerts cytostatic effect via p53/p21 up-regulation and suppresses metastasis in 7,12-dimethylbenz(α)anthracene-induced rat mammary carcinoma.
PubMed: Tangeretin ameliorates oxidative stress in the renal tissues of rats with experimental breast cancer induced by 7,12-dimethylbenz[a]anthracene.
PubMed: Hesperidin, nobiletin, and tangeretin are collectively responsible for the anti-neuroinflammatory capacity of tangerine peel (Citri reticulatae pericarpium).
PubMed: Pro-apoptotic effects of the novel tangeretin derivate 5-acetyl-6,7,8,4'-tetramethylnortangeretin on MCF-7 breast cancer cells.
PubMed: An investigation of molecular dynamics simulation and molecular docking: interaction of citrus flavonoids and bovine β-lactoglobulin in focus.
PubMed: Soluble and insoluble phenolic compounds and antioxidant activity of immature calamondin affected by solvents and heat treatment.
PubMed: Identification of the effective constituents for anti-inflammatory activity of Ju-Zhi-Jiang-Tang, an ancient traditional Chinese medicine formula.
PubMed: [Chemical constituents from leaves of Ilex latifolia].
PubMed: Tangeretin-loaded protein nanoparticles fabricated from zein/β-lactoglobulin: preparation, characterization, and functional performance.
PubMed: Effect of tangeretin, a polymethoxylated flavone on glucose metabolism in streptozotocin-induced diabetic rats.
PubMed: Tangeretin, a citrus polymethoxyflavonoid, induces apoptosis of human gastric cancer AGS cells through extrinsic and intrinsic signaling pathways.
PubMed: Sonochemical effects on 14 flavonoids common in citrus: relation to stability.
PubMed: Tangeretin exerts anti-neuroinflammatory effects via NF-κB modulation in lipopolysaccharide-stimulated microglial cells.
PubMed: Antiviral activity of polymethoxylated flavones from "Guangchenpi", the edible and medicinal pericarps of citrus reticulata 'Chachi'.
PubMed: Chemotherapeutic effect of tangeretin, a polymethoxylated flavone studied in 7, 12-dimethylbenz(a)anthracene induced mammary carcinoma in experimental rats.
PubMed: Tangeretin regulates platelet function through inhibition of phosphoinositide 3-kinase and cyclic nucleotide signaling.
PubMed: Application of the solvent extraction technique to investigation of the anti-inflammatory activity of adlay bran.
PubMed: Simultaneous determination of six bioactive flavonoids in Citri Reticulatae Pericarpium by rapid resolution liquid chromatography coupled with triple quadrupole electrospray tandem mass spectrometry.
PubMed: The ethanol extract isolated from Weiqi Decoction induces G₂/M arrest and apoptosis in AGS cells.
PubMed: Nobiletin and tangeretin ameliorate scratching behavior in mice by inhibiting the action of histamine and the activation of NF-κB, AP-1 and p38.
PubMed: 6-demethoxynobiletin, a nobiletin-analog citrus flavonoid, enhances extracellular signal-regulated kinase phosphorylation in PC12D cells.
PubMed: 5-demethyltangeretin inhibits human nonsmall cell lung cancer cell growth by inducing G2/M cell cycle arrest and apoptosis.
PubMed: Effect of a labile methyl donor on the transformation of 5-demethyltangeretin and the related implication on bioactivity.
PubMed: Tangeretin sensitizes SGS1-deficient cells by inducing DNA damage.
PubMed: Boehmeria nivea attenuates LPS-induced inflammatory markers by inhibiting p38 and JNK phosphorylations in RAW264.7 macrophages.
PubMed: [Determination of the active constituents in aurantii fructus from Jiangxi province at different harvest time by HPLC].
PubMed: Rapid screening of bioactive compounds from natural products by integrating 5-channel parallel chromatography coupled with on-line mass spectrometry and microplate based assays.
PubMed: Potent activity of nobiletin-rich Citrus reticulata peel extract to facilitate cAMP/PKA/ERK/CREB signaling associated with learning and memory in cultured hippocampal neurons: identification of the substances responsible for the pharmacological action.
PubMed: Simultaneous quantification of paeoniflorin, nobiletin, tangeretin, liquiritigenin, isoliquiritigenin, liquiritin and formononetin from Si-Ni-San extract in rat plasma and tissues by liquid chromatography-tandem mass spectrometry.
PubMed: Nobiletin attenuates metastasis via both ERK and PI3K/Akt pathways in HGF-treated liver cancer HepG2 cells.
PubMed: Naturally occurring flavonoids against human norovirus surrogates.
PubMed: Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.
PubMed: Antioxidant activity and effective compounds of immature calamondin peel.
PubMed: Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
PubMed: Protective effects of sweet orange (Citrus sinensis) peel and their bioactive compounds on oxidative stress.
PubMed: HPLC-PDA-MS and NMR characterization of a hydroalcoholic extract of Citrus aurantium L. var. amara peel with antiedematogenic activity.
PubMed: Polymethoxy flavonoids, nobiletin and tangeretin, prevent lipopolysaccharide-induced inflammatory bone loss in an experimental model for periodontitis.
PubMed: The composition of volatile aroma components, flavanones, and polymethoxylated flavones in Shiikuwasha (Citrus depressa Hayata) peels of different cultivation lines.
PubMed: Mild mitochondrial depolarization is involved in a neuroprotective mechanism of Citrus sunki peel extract.
PubMed: Polymethoxyflavonoids tangeretin and nobiletin increase glucose uptake in murine adipocytes.
PubMed: Suppression of AMF/PGI-mediated tumorigenic activities by ursolic acid in cultured hepatoma cells and in a mouse model.
PubMed: Natural products for cancer-targeted therapy: citrus flavonoids as potent chemopreventive agents.
PubMed: Tangeretin stimulates glucose uptake via regulation of AMPK signaling pathways in C2C12 myotubes and improves glucose tolerance in high-fat diet-induced obese mice.
PubMed: Phenolic constituents from the heartwood of Artocapus altilis and their tyrosinase inhibitory activity.
PubMed: Optimized assays for human UDP-glucuronosyltransferase (UGT) activities: altered alamethicin concentration and utility to screen for UGT inhibitors.
PubMed: Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities.
PubMed: Simultaneous quantification of polymethoxylated flavones and coumarins in Fructus aurantii and Fructus aurantii immaturus using HPLC-ESI-MS/MS.
PubMed: Tangeretin, a citrus flavonoid, inhibits PGDF-BB-induced proliferation and migration of aortic smooth muscle cells by blocking AKT activation.
PubMed: Quality control of Citri reticulatae pericarpium: exploratory analysis and discrimination.
PubMed: Chemical composition and biological activity of Citrus jambhiri Lush.
PubMed: Inhibition of citral degradation by oil-in-water nanoemulsions combined with antioxidants.
PubMed: Molecular structures of citrus flavonoids determine their effects on lipid metabolism in HepG2 cells by primarily suppressing apoB secretion.
PubMed: Suppression of hepatitis B virus x protein-mediated tumorigenic effects by ursolic Acid.
PubMed: Regulation of adipocytokine secretion and adipocyte hypertrophy by polymethoxyflavonoids, nobiletin and tangeretin.
PubMed: Tangeretin and its metabolite 4'-hydroxytetramethoxyflavone attenuate EGF-stimulated cell cycle progression in hepatocytes; role of inhibition at the level of mTOR/p70S6K.
PubMed: Pharmacokinetic study of nobiletin and tangeretin in rat serum by high-performance liquid chromatography-electrospray ionization-mass spectrometry.
PubMed: Tangeretin reduces ultraviolet B (UVB)-induced cyclooxygenase-2 expression in mouse epidermal cells by blocking mitogen-activated protein kinase (MAPK) activation and reactive oxygen species (ROS) generation.
PubMed: Binding Citrus flavanones to human serum albumin: effect of structure on affinity.
PubMed: Simultaneous determination of flavonoids in different parts of Citrus reticulata 'Chachi' fruit by high performance liquid chromatography-photodiode array detection.
PubMed: [Study on the contents of flavonoids in Citrus reticulata 'Chachi' from various habitats and different collecting periods].
PubMed: Induction of apoptosis in human cervical carcinoma HeLa cells by polymethoxylated flavone-rich Citrus grandis Osbeck (Dangyuja) leaf extract.
PubMed: Use of silkworms for identification of drug candidates having appropriate pharmacokinetics from plant sources.
PubMed: Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.
PubMed: Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells.
PubMed: Semisynthesis of natural flavones inhibiting tubulin polymerization, from hesperidin.
PubMed: Hepatoprotective effects of flavonoids from shekwasha (Citrus depressa) against D-galactosamine-induced liver injury in rats.
PubMed: Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook.
PubMed: The flavonoid tangeretin activates the unfolded protein response and synergizes with imatinib in the erythroleukemia cell line K562.
PubMed: Tangeretin sensitizes cisplatin-resistant human ovarian cancer cells through downregulation of phosphoinositide 3-kinase/Akt signaling pathway.
PubMed: Effects of naturally occurring polymethyoxyflavonoids on cell growth, p-glycoprotein function, cell cycle, and apoptosis of daunorubicin-resistant T lymphoblastoid leukemia cells.
PubMed: Simultaneous determination of five bioactive flavonoids in pericarpium Citri reticulatae from china by high-performance liquid chromatography with dual wavelength detection.
PubMed: Fingerprinting alterations of secondary metabolites of tangerine peels during growth by HPLC-DAD and chemometric methods.
PubMed: Semisynthesis and antiproliferative evaluation of a series of 3'-aminoflavones.
PubMed: UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii.
PubMed: Synthesis and biological evaluation of a series of tangeretin-derived chalcones.
PubMed: Suppressive effects of demethylated metabolites of nobiletin on phorbol ester-induced expression of scavenger receptor genes in THP-1 human monocytic cells.
PubMed: Investigation of heat treating conditions for enhancing the anti-inflammatory activity of citrus fruit (Citrus reticulata) peels.
PubMed: Activation of pregnane X receptor and induction of MDR1 by dietary phytochemicals.
PubMed: Inhibition of oral carcinogenesis by citrus flavonoids.
PubMed: Plant polyphenolics as anti-invasive cancer agents.
PubMed: Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells.
PubMed: Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water.
PubMed: Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.
PubMed: Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts.
PubMed: Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3.
PubMed: Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.
PubMed: Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass?
PubMed: Biotransformation of polymethoxylated flavonoids: access to their 4'-O-demethylated metabolites.
PubMed: Effects of various methoxyflavones on vincristine uptake and multidrug resistance to vincristine in P-gp-overexpressing K562/ADM cells.
PubMed: Chemopreventive effects of orange peel extract (OPE). II: OPE inhibits atypical hyperplastic lesions in rodent mammary gland.
PubMed: Chemopreventive effects of orange peel extract (OPE). I: OPE inhibits intestinal tumor growth in ApcMin/+ mice.
PubMed: Correlation between flavonoid content and the NO production inhibitory activity of peel extracts from various citrus fruits.
PubMed: Inhibitors of stress-activated protein/mitogen-activated protein kinase pathways.
PubMed: Quality control and discrimination of pericarpium citri reticulatae and pericarpium citri reticulatae viride based on high-performance liquid chromatographic fingerprints and multivariate statistical analysis.
PubMed: Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.
PubMed: Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.
PubMed: Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry.
PubMed: Tangeretin and nobiletin induce G1 cell cycle arrest but not apoptosis in human breast and colon cancer cells.
PubMed: [Chemical constituents from roots of Platycodon grandiflorum].
PubMed: TCDD-induced CYP1A1 expression, an index of dioxin toxicity, is suppressed by flavonoids permeating the human intestinal Caco-2 cell monolayers.
PubMed: Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.
PubMed: Tangeretin suppresses IL-1beta-induced cyclooxygenase (COX)-2 expression through inhibition of p38 MAPK, JNK, and AKT activation in human lung carcinoma cells.
PubMed: Efficient and scalable method in isolation of polymethoxyflavones from orange peel extract by supercritical fluid chromatography.
PubMed: Methoxyflavones protect cells against endoplasmic reticulum stress and neurotoxin.
PubMed: [Chemical constituents from roots of Ficus hirta].
PubMed: Liquid chromatography/mass spectrometry and liquid chromatography/nuclear magnetic resonance as complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residues from molecular distillation of orange peel oils (Citrus sinensis).
PubMed: Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities.
PubMed: Preparative isolation and purification of polymethoxylated flavones from Tangerine peel using high-speed counter-current chromatography.
PubMed: Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin.
PubMed: A safety study of oral tangeretin and xanthohumol administration to laboratory mice.
PubMed: Tangeretin inhibits extracellular-signal-regulated kinase (ERK) phosphorylation.
PubMed: Nobiletin, a citrus flavonoid isolated from tangerines, selectively inhibits class A scavenger receptor-mediated metabolism of acetylated LDL by mouse macrophages.
PubMed: Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux.
PubMed: Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: relationship between structure and activity.
PubMed: Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced hypercholesterolemia.
PubMed: Modulation of HepG2 cell net apolipoprotein B secretion by the citrus polymethoxyflavone, tangeretin.
PubMed: Steroid activities comparison of natural and food wrap compounds in human breast cancer cell lines.
PubMed: Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora.
PubMed: An assessment of udp-glucuronosyltransferase induction using primary human hepatocytes.
PubMed: Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice.
PubMed: Estrogenic effects of food wrap packaging xenoestrogens and flavonoids in female Wistar rats: a comparative study.
PubMed: In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s.
PubMed: Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol-3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes.
PubMed: Tangeretin induces cell-cycle G1 arrest through inhibiting cyclin-dependent kinases 2 and 4 activities as well as elevating Cdk inhibitors p21 and p27 in human colorectal carcinoma cells.
PubMed: [Studies on chemical constituents of processed green tangerine peel].
PubMed: The citrus methoxyflavone tangeretin affects human cell-cell interactions.
PubMed: Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels.
PubMed: Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones.
PubMed: Effects of several flavonoids on the growth of B16F10 and SK-MEL-1 melanoma cell lines: relationship between structure and activity.
PubMed: Inhibition of 11beta-hydroxysteroid dehydrogenase in guinea pig kidney by three bioflavonoids and their interactions with gossypol.
PubMed: Tissue distribution and neuroprotective effects of citrus flavonoid tangeretin in a rat model of Parkinson's disease.
PubMed: 8-Prenylnaringenin, the phytoestrogen in hops and beer, upregulates the function of the E-cadherin/catenin complex in human mammary carcinoma cells.
PubMed: Immunotoxicity of a standardized citrus polymethoxylated flavone extract.
PubMed: Evaluation of the effects of swainsonine, captopril, tangeretin and nobiletin on the biological behaviour of brain tumour cells in vitro.
PubMed: Mechanisms involved in the chemoprevention of flavonoids.
PubMed: Antibacterial activity of Citrus reticulata peel extracts.
PubMed: Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells.
PubMed: Inhibitors of 15-lipoxygenase from orange peel.
PubMed: Inhibition of tamoxifen's therapeutic benefit by tangeretin in mammary cancer.
PubMed: Biotransformation of the citrus flavone tangeretin in rats. Identification of metabolites with intact flavane nucleus.
PubMed: Lack of correlation between in vitro and in vivo studies on the effects of tangeretin and tangerine juice on midazolam hydroxylation.
PubMed: Polymethoxylated flavones in orange juice are inhibitors of P-glycoprotein but not cytochrome P450 3A4.
PubMed: A citrus flavonoid, nobiletin, suppresses production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts.
PubMed: Differential effects of dietary flavonoids on drug metabolizing and antioxidant enzymes in female rat.
PubMed: HL-60 differentiating activity and flavonoid content of the readily extractable fraction prepared from citrus juices.
PubMed: Influence of putative antiinvasive agents on matrix metalloproteinase secretion by human neoplastic glia in vitro.
PubMed: Antiproliferative activity of flavonoids on several cancer cell lines.
PubMed: Effect of citrus flavonoids on HL-60 cell differentiation.
PubMed: Inhibition of xenobiotic-induced genotoxicity in cultured precision-cut human and rat liver slices.
PubMed: Influence of tangeretin on tamoxifen's therapeutic benefit in mammary cancer.
PubMed: In vitro biotransformation of flavonoids by rat liver microsomes.
PubMed: Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography.
PubMed: Flavonoids (apigenin, tangeretin) counteract tumor promoter-induced inhibition of intercellular communication of rat liver epithelial cells.
PubMed: Time course of induction of rat hepatic drug-metabolizing enzyme activities following dietary administration of flavonoids.
PubMed: Comparative effects of flavonoids and model inducers on drug-metabolizing enzymes in rat liver.
PubMed: Regulation of the invasion suppressor function of the cadherin/catenin complex.
PubMed: Inhibition of bacterial mutagenesis by Citrus flavonoids.
PubMed: [Studies on the bioactive constituents of Aurantii Fructus Immaturus].
PubMed: Differential effects of nonhydroxylated flavonoids as inducers of cytochrome P450 1A and 2B isozymes in rat liver.
PubMed: Lack of tumor-promoting effects of flavonoids: studies on rat liver preneoplastic foci and on in vivo and in vitro gap junctional intercellular communication.
PubMed: The E-cadherin/catenin complex in invasion and metastasis.
PubMed: Isolation of anti-leukemia compounds from Citrus reticulata.
PubMed: Citrus flavone tangeretin inhibits leukaemic HL-60 cell growth partially through induction of apoptosis with less cytotoxicity on normal lymphocytes.
PubMed: Effects of bioflavonoids on hepatic P450 activities.
PubMed: Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes.
PubMed: Apigenin and tangeretin enhance gap junctional intercellular communication in rat liver epithelial cells.
PubMed: Effects of flavonoids on cytochrome P450-dependent acetaminophen metabolism in rats and human liver microsomes.
PubMed: Evidence for tangeretin O-demethylation by rat and human liver microsomes.
PubMed: Citrus flavonoids stimulate secretion by human colonic T84 cells.
PubMed: Differential inhibition of proliferation of human squamous cell carcinoma, gliosarcoma and embryonic fibroblast-like lung cells in culture by plant flavonoids.
PubMed: Inhibition of microsome-mediated binding of benzo[a]pyrene to DNA by flavonoids either in vitro or after dietary administration to rats.
PubMed: Dietary modification of drug-metabolizing enzyme activities: dose-response effect of flavonoids.
PubMed: Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro.
PubMed: Effect of catechins and citrus flavonoids on invasion in vitro.
PubMed: Induction of monooxygenase and transferase activities in rat by dietary administration of flavonoids.
PubMed: The flavonoid tangeretin inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro.
PubMed: Anti-invasive activities of experimental chemotherapeutic agents.
PubMed: C18 solid-phase isolation and high-performance liquid chromatography/ultraviolet diode array determination of fully methoxylated flavones in citrus juices.
PubMed: Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship.
PubMed: The effects of flavonoids on human lymphocyte proliferative responses.
PubMed: Some effects of flavonoids on lymphocyte proliferative responses.
PubMed: Flavonoid inhibition of human basophil histamine release stimulated by various agents.
PubMed: Inhibition of aflatoxin B1 carcinogenesis in rainbow trout by flavone and indole compounds.
PubMed: In vitro and in vivo activation of oxidative drug metabolism by flavonoids.
PubMed: Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids.
PubMed: Inhibition by quercetin of thyroid hormone stimulation in vitro of human red blood cell Ca2+-ATPase activity.
PubMed: Activation and inhibition of benzo(a)pyrene and aflatoxin B1 metabolism in human liver microsomes by naturally occurring flavonoids.
PubMed: Regulation of human drug metabolism by dietary factors.
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