Tangeretin
| |
| Names | |
|---|---|
| IUPAC names
5,6,7,8-tetramethoxy-2-
(4-methoxyphenyl)-4H- 1-benzopyran-4-one | |
| Identifiers | |
3D model (JSmol)
|
|
| ECHA InfoCard | 100.006.883 |
CompTox Dashboard (EPA)
|
|
| |
| Properties | |
| C20H20O7 | |
| Molar mass | 372.37 g/mol |
| Melting point | 155-156 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Tangeritin is a polymethoxylated flavone that is found in tangerine and other citrus peels. Tangeritin strengthens the cell wall and protects it from invasion [citation needed].
Although few randomized, double-blind human studies have been done, animal research shows the potential of tangeritin as a cholesterol lowering agent[1]. A hamster study showed potential protective effects against Parkinson's disease[2]. Tangeritin shows potential as an anti cancer agent. In in vitro studies, tangeritin appears to counteract some of the adaptations of cancer cells. Tangeritin induced apoptosis in leukemia cells while sparing normal cells[3]. It counteracts tumor suppression of gap junction intercellular signaling[4]. It acts to freeze cancer cells in phase G1 of the cell cycle, preventing replication. In summary, in vitro studies show antimutagenic[5], antiinvasive[6] and antiproliferative[7] effects. One caveat is that tangeritin appears to counteract the anticancer drug tamoxifen and to suppress the activity of natural killer cells[8].
Tangeritin is commercially available as a dietary supplement.
See also
References
- ^ Kurowska EM, Manthey JA (2004). "Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced hypercholesterolemia". J. Agric. Food Chem. 52 (10): 2879–86. doi:10.1021/jf035354z. PMID 15137829.
{{cite journal}}: Unknown parameter|month=ignored (help) - ^ Datla KP, Christidou M, Widmer WW, Rooprai HK, Dexter DT (2001). "Tissue distribution and neuroprotective effects of citrus flavonoid tangeretin in a rat model of Parkinson's disease". Neuroreport. 12 (17): 3871–5. doi:10.1097/00001756-200112040-00053. PMID 11726811.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Hirano T, Abe K, Gotoh M, Oka K (1995). "Citrus flavone tangeretin inhibits leukaemic HL-60 cell growth partially through induction of apoptosis with less cytotoxicity on normal lymphocytes". Br. J. Cancer. 72 (6): 1380–8. PMID 8519648.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Chaumontet C, Droumaguet C, Bex V, Heberden C, Gaillard-Sanchez I, Martel P (1997). "Flavonoids (apigenin, tangeretin) counteract tumor promoter-induced inhibition of intercellular communication of rat liver epithelial cells". Cancer Lett. 114 (1–2): 207–10. doi:10.1016/S0304-3835(97)04664-8. PMID 9103293.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Calomme M, Pieters L, Vlietinck A, Vanden Berghe D (1996). "Inhibition of bacterial mutagenesis by Citrus flavonoids". Planta Med. 62 (3): 222–6. doi:10.1055/s-2006-957864. PMID 8693033.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Bracke ME, Vyncke BM, Van Larebeke NA; et al. (1989). "The flavonoid tangeretin inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro". Clin. Exp. Metastasis. 7 (3): 283–300. doi:10.1007/BF01753681. PMID 2924447.
{{cite journal}}: Explicit use of et al. in:|author=(help)CS1 maint: multiple names: authors list (link) - ^ Kandaswami C, Perkins E, Soloniuk DS, Drzewiecki G, Middleton E (1991). "Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro". Cancer Lett. 56 (2): 147–52. doi:10.1016/0304-3835(91)90089-Z. PMID 1998943.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Depypere HT, Bracke ME, Boterberg T; et al. (2000). "Inhibition of tamoxifen's therapeutic benefit by tangeretin in mammary cancer". Eur. J. Cancer. 36 (Suppl 4): S73. doi:10.1016/S0959-8049(00)00234-3. PMID 11056327.
{{cite journal}}: Explicit use of et al. in:|author=(help); Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link)