Tangeretin: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~444130959~~
			\| Watchedfields = changed
⚫	\| Name = Tangeritin
		⚫	\| verifiedrevid = 444133047
	\| ImageFile = Tangeritin_structure.png
		⚫	\| Name = Tangeretin (Tangeritin)
⚫	~~<!--~~ \| ImageSize = ~~200px -->~~
			\| ImageFile = Tangeritin.svg
	\| ImageName =
		⚫	\| ImageSize = 220
⚫	\| ~~IUPACName~~ = 5,6,7,8-~~tetramethoxy~~-2-~~<br />~~(4-methoxyphenyl)-4H-~~<br />~~1-benzopyran-4-one
			\| ImageAlt = Skeletal formula
⚫	\| Section1 = {{Chembox Identifiers
			\| ImageFile1 = Tangeritin molecule ball.png
⚫	\| CASNo = 481-53-8
			\| ImageSize1 = 220
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| ImageAlt1 = Ball-and-stick model
			\| IUPACName = 4′,5,6,7,8-Pentamethoxyflavone
		⚫	\| SystematicName = 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4''H''-1-benzopyran-4-one
		⚫	\|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		\| UNII = I4TLA1DLX6
	\| SMILES = O=C2C1=C(OC)C(OC)=C(OC)C(OC)~~<br />~~=C1OC(C3=CC=C(OC)C=C3)=C2		\| 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		\|Section2={{Chembox Properties
	\| Formula = C<sub>20</sub>H<sub>20</sub>O<sub>7</sub>		\| Formula = C<sub>20</sub>H<sub>20</sub>O<sub>7</sub>
	\| MolarMass = 372.37 g/mol		\| MolarMass = 372.37 g/mol
			\| Density = 1.244 ± 0.06 g/cm<sup>3</sup><ref name="SciFinder">SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8).</ref>
	\| MeltingPt = 155-156 °C
			\| Solubility = 0.037 g/L<ref name="SciFinder" />
			\| BoilingPtC = 565.3 +/- 50.0
			\| BoilingPt_ref = <ref name="SciFinder" />
			\| MeltingPtC = 155 to 156
			\| MeltingPt_notes =
	}}		}}
	}}		}}

	'''~~Tangeritin~~''' is an O-] that is found in ] and other ] peels. ~~Tangeritin~~ strengthens the cell wall and ~~protects~~ it ~~from~~ ~~invasion~~ ~~{{Citation~~ ~~needed\|date~~=~~January~~ ~~2008}}~~.		'''Tangeretin''' is an O-] that is found in ] and other ] peels. Tangeretin strengthens the cell wall and acts as a plant's defensive mechanism against disease-causing pathogens.<ref name = "Uckoo">Uckoo, RM; et al. Sep. Purif. Technol. 2011.</ref>

			It has also been used as a marker compound to detect contamination in citrus juices.<ref name="Uckoo" />
	Although few oj, double-blind human studies have been done, animal research shows the potential of tangeritin as a cholesterol lowering agent<ref>{{cite journal \|author=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 \|year=2004 \|month=May \|pmid=15137829 \|doi=10.1021/jf035354z }}</ref>. A hamster study showed potential protective effects against ]<ref>{{cite journal \|author=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 \|year=2001 \|month=December \|pmid=11726811 \|doi=10.1097/00001756-200112040-00053 }}</ref>. 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 ] in leukemia cells while sparing normal cells<ref>{{cite journal \|author=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 \|year=1995 \|month=December \|pmid=8519648 \|pmc=2034105 }}</ref>. It counteracts tumor suppression of ] ]<ref>{{cite journal \|author=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 \|year=1997 \|month=March \|pmid=9103293 \|doi=10.1016/S0304-3835(97)04664-8 }}</ref>. It acts to freeze cancer cells in phase ] of the cell cycle, preventing replication. In summary, ''in vitro'' studies show antimutagenic<ref>{{cite journal \|author=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 \|year=1996 \|month=June \|pmid=8693033 \|doi=10.1055/s-2006-957864 }}</ref>, antiinvasive<ref>{{cite journal \|author=Bracke ME, Vyncke BM, Van Larebeke NA, ''et al.'' \|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 }}</ref> and antiproliferative<ref>{{cite journal \|author=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 \|year=1991 \|month=February \|pmid=1998943 \|doi=10.1016/0304-3835(91)90089-Z }}</ref> effects. One caveat is that tangeritin appears to counteract the anticancer drug ] and to suppress the activity of natural killer cells<ref>{{cite journal \|author=Depypere HT, Bracke ME, Boterberg T, ''et al.'' \|title=Inhibition of tamoxifen's therapeutic benefit by tangeretin in mammary cancer \|journal=Eur. J. Cancer \|volume=36 \|issue=Suppl 4\|pages=S73 \|year=2000 \|month=September \|pmid=11056327 \|doi=10.1016/S0959-8049(00)00234-3 }}</ref>.

			The following is a list of methods used to extract tangeretin from citrus peels:
	Tangeritin is commercially available as a dietary supplement.
			* column chromatography
			* preparative-high performance liquid chromatography
			* super critical fluid chromatography
			* high speed counter current chromatography
			* a combination of vacuum flash silica gel chromatography and flash C<sub>8</sub> column chromatography
			* flash chromatography
			* isolation using ionic liquids and a cycle of centrifugation and decantation<ref name = "Mizuno, H. et al.">Mizuno, H.; Yoshikawa, H.; Usuki, T. Extraction of Nobiletin and Tangeretin From Peels of Shekwasha and Ponkan Using and Centrifugation. Natural Product Communications 2019, 14, 1-6.
			</ref>
			The low solubility of Tangeretin is one of the main reasons for the low bioavailability of Tangeretin (and other flavonoids in general), and has been reported as a major challenge when using the compound in laboratory procedures.<ref name = "Panche, A. N. et al.">Panche, A. N.; Diwan, A. D.; Chandra, S. R. Flavonoids: an overview. Journal of Nutritional Science. 2016, 5, 47.
			</ref>
			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.<ref name="Uckoo" />

			Tangeretin is commercially available as a dietary supplement. Tangeretin has also demonstrated beneficial applications in other pharmaceutical, nutraceutical, and cosmetic processes.<ref name = "Panche, A. N. et al."></ref>
⚫	==References==

			Tangeretin can be found as various synonyms throughout literature and research, including '''Tangeritin''' and '''5,6,7,8,4’-pentamethoxyflavone (VIII)'''.<ref name = "Mizuno, H. et al."></ref>

		⚫	== References ==
	{{reflist}}		{{reflist}}

	{{flavone}}		{{flavone}}

	]		]
	]		]
			]

	]
	]
	]

Latest revision as of 16:41, 23 September 2024

Tangeretin (Tangeritin)
Names


IUPAC name 4′,5,6,7,8-Pentamethoxyflavone
Systematic IUPAC name 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Identifiers
CAS Number	481-53-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9400
ChemSpider	61389
ECHA InfoCard	100.006.883
EC Number	207-570-1
KEGG	C10190
PubChem CID	68077
UNII	I4TLA1DLX6
CompTox Dashboard (EPA)	DTXSID30197417
InChI InChI=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,1-5H3Key: ULSUXBXHSYSGDT-UHFFFAOYSA-N 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,1-5H3Key: ULSUXBXHSYSGDT-UHFFFAOYAG
SMILES O=C2C1=C(OC)C(OC)=C(OC)C(OC)=C1OC(C3=CC=C(OC)C=C3)=C2
Properties
Chemical formula	C₂₀H₂₀O₇
Molar mass	372.37 g/mol
Density	1.244 ± 0.06 g/cm
Melting point	155 to 156 °C (311 to 313 °F; 428 to 429 K)
Boiling point	565.3 ± 50.0 °C (1,049.5 ± 90.0 °F; 838.4 ± 50.0 K)
Solubility in water	0.037 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

It has also been used as a marker compound to detect contamination in citrus juices.

The following is a list of methods used to extract tangeretin from citrus peels:

column chromatography
preparative-high performance liquid chromatography
super critical fluid chromatography
high speed counter current chromatography
a combination of vacuum flash silica gel chromatography and flash C₈ column chromatography
flash chromatography
isolation using ionic liquids and a cycle of centrifugation and decantation

The low solubility of Tangeretin is one of the main reasons for the low bioavailability of Tangeretin (and other flavonoids in general), and has been reported as a major challenge when using the compound in laboratory procedures. 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.

Tangeretin is commercially available as a dietary supplement. Tangeretin has also demonstrated beneficial applications in other pharmaceutical, nutraceutical, and cosmetic processes.

Tangeretin can be found as various synonyms throughout literature and research, including Tangeritin and 5,6,7,8,4’-pentamethoxyflavone (VIII).

References

^ SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8).
^ Uckoo, RM; et al. Sep. Purif. Technol. 2011.
^ Mizuno, H.; Yoshikawa, H.; Usuki, T. Extraction of Nobiletin and Tangeretin From Peels of Shekwasha and Ponkan Using and Centrifugation. Natural Product Communications 2019, 14, 1-6.
^ Panche, A. N.; Diwan, A. D.; Chandra, S. R. Flavonoids: an overview. Journal of Nutritional Science. 2016, 5, 47.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide

Acetylated

Artocarpetin A

Artoindonesianin P

Sulfated glycosides

Theograndin I and II

Polymers

Drugs

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