| 词条 | Tangeretin |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444133047 | Name = Tangeretin (Tangeritin) | ImageFile = Tangeritin.svg | ImageSize = 220 | ImageAlt = Skeletal formula | ImageFile1 = Tangeritin molecule ball.png | ImageSize1 = 220 | ImageAlt1 = Ball-and-stick model | IUPACName = 5,6,7,8-tetramethoxy-2- |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 481-53-8 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 9400 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I4TLA1DLX6 | SMILES = O=C2C1=C(OC)C(OC)=C(OC)C(OC)=C1OC(C3=CC=C(OC)C=C3)=C2 | EINECS = 207-570-1 | PubChem = 68077 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 61389 | InChI = 1/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3 | InChIKey = ULSUXBXHSYSGDT-UHFFFAOYAG | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = ULSUXBXHSYSGDT-UHFFFAOYSA-N | RTECS = | MeSHName = | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C10190 |Section2={{Chembox Properties | Formula = C20H20O7 | MolarMass = 372.37 g/mol | Density = 1.244 ± 0.06 g/cm3[1] | BoilingPtC = 565.3 +/- 50.0 | BoilingPt_ref = [1] | MeltingPtC = 155 to 156 | MeltingPt_notes = }}Tangeretin is an O-polymethoxylated flavone that is found in tangerine and other citrus peels. Tangeretin strengthens the cell wall and acts as a plant's defensive mechanism against disease-causing pathogens.[2] It has also been used as a marker compound to detect contamination in citrus juices.[2] Although few randomized, double-blind human studies have been done, animal research shows the potential of tangeretin as a cholesterol lowering agent.[3] A study on rats demonstrated potential protective effects against Parkinson's disease.[4] Tangeretin also shows enormous potential as an anti cancer agent. In in vitro studies, tangeretin appears to counteract some of the adaptations of cancer cells. Tangeretin induced apoptosis in leukemia cells while sparing normal cells.[5] In a study on two human breast cancer cell lines and one colon cancer cell line, tangeretin blocked cell cycle progression at the G1 (growth) phase in all three cell lines, without inducing apoptosis in the tumor cell lines. Once tangeretin was removed from the tumor cells, their cell cycle progression returned to normal.[6] Tangeretin also counteracts tumor suppression of gap junction intercellular signaling.[7] In summary, in vitro studies show antimutagenic,[8] antiinvasive[9] and antiproliferative[10] effects. One caveat is that tangeretin appears to counteract the anticancer drug tamoxifen and to suppress the activity of natural killer cells.[11] The following is a list of methods used to extract tangeretin from citrus peels:
However, methods for tangeretin extraction are currently being tested to maximize efficiency and percent yields as its uses in treatment of cancer and other diseases are becoming better understood.[2] Tangeretin is commercially available as a dietary supplement. References1. ^1 SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8). {{flavone}}2. ^1 2 Uckoo, RM; et al. Sep. Purif. Technol. 2011. 3. ^{{cite journal |vauthors=Kurowska EM, Manthey JA |title=Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced hypercholesterolemia |journal=J. Agric. Food Chem. |volume=52 |issue=10 |pages=2879–86 |date=May 2004 |pmid=15137829 |doi=10.1021/jf035354z }} 4. ^{{cite journal |vauthors=Datla KP, Christidou M, Widmer WW, Rooprai HK, Dexter DT |title=Tissue distribution and neuroprotective effects of citrus flavonoid tangeretin in a rat model of Parkinson's disease |journal=NeuroReport |volume=12 |issue=17 |pages=3871–5 |date=December 2001 |pmid=11726811 |doi=10.1097/00001756-200112040-00053 }} 5. ^{{cite journal |vauthors=Hirano T, Abe K, Gotoh M, Oka K |title=Citrus flavone tangeretin inhibits leukaemic HL-60 cell growth partially through induction of apoptosis with less cytotoxicity on normal lymphocytes |journal=Br. J. Cancer |volume=72 |issue=6 |pages=1380–8 |date=December 1995 |pmid=8519648 |pmc=2034105 |doi=10.1038/bjc.1995.518}} 6. ^Morley, KL; et al. Cancer Lett. 2007. 7. ^{{cite journal |vauthors=Chaumontet C, Droumaguet C, Bex V, Heberden C, Gaillard-Sanchez I, Martel P |title=Flavonoids (apigenin, tangeretin) counteract tumor promoter-induced inhibition of intercellular communication of rat liver epithelial cells |journal=Cancer Lett. |volume=114 |issue=1–2 |pages=207–10 |date=March 1997 |pmid=9103293 |doi=10.1016/S0304-3835(97)04664-8 }} 8. ^{{cite journal |vauthors=Calomme M, Pieters L, Vlietinck A, Vanden Berghe D |title=Inhibition of bacterial mutagenesis by Citrus flavonoids |journal=Planta Med. |volume=62 |issue=3 |pages=222–6 |date=June 1996 |pmid=8693033 |doi=10.1055/s-2006-957864 }} 9. ^{{cite journal |vauthors=Bracke ME, Vyncke BM, Van Larebeke NA, etal |title=The flavonoid tangeretin inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro |journal=Clin. Exp. Metastasis |volume=7 |issue=3 |pages=283–300 |year=1989 |pmid=2924447 |doi=10.1007/BF01753681 }} 10. ^{{cite journal |vauthors=Kandaswami C, Perkins E, Soloniuk DS, Drzewiecki G, Middleton E |title=Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro |journal=Cancer Lett. |volume=56 |issue=2 |pages=147–52 |date=February 1991 |pmid=1998943 |doi=10.1016/0304-3835(91)90089-Z }} 11. ^{{cite journal |vauthors=Depypere HT, Bracke ME, Boterberg T, etal |title=Inhibition of tamoxifen's therapeutic benefit by tangeretin in mammary cancer |journal=Eur. J. Cancer |volume=36 |issue=Suppl 4|pages=S73 |date=September 2000 |pmid=11056327 |doi=10.1016/S0959-8049(00)00234-3 }} 2 : O-Methylated flavones|Flavonoids found in Rutaceae |
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