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Revision as of 13:32, 20 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'UNII_Ref') per Chem/Drugbox validation (report errors or bugs)		Latest revision as of 09:44, 24 April 2024 edit HansVonStuttgart (talk | contribs)Extended confirmed users1,559 edits clarifyTag: 2017 wikitext editor
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			{{Cleanup rewrite|date=March 2020}}
	{{Chembox		{{Chembox
			| Watchedfields = changed
			| verifiedrevid = 403346640
	| Watchedfields = changed
			| Name =
	| verifiedrevid = 399504350
	| ImageFile = Amentoflavone.svg		| ImageFile = Hinokinin.png
			| ImageSize =
			| ImageAlt =
	| ImageSize =
			| ImageFile1 =
			| ImageAlt1 =
	| IUPACName = 8--5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
			| PIN = (3''R'',4''R'')-3,4-Bisoxolan-2-one
			| OtherNames = (3''R'',4''R'')-3,4-Bis(1,3-benzodioxol-5-ylmethyl)dihydro-2(3''H'')-furanone
	| OtherNames = Didemethyl-ginkgetin<br>3',8''-Biapigenin
			| Section1 = {{Chembox Identifiers
			| InChIKey = DDWGQGZPYDSYEL-LSDHHAIUSA-N
	| Section1 = {{Chembox Identifiers
	| InChIKey = YUSWMAULDXZHPY-UHFFFAOYAB
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H		| StdInChI = 1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = YUSWMAULDXZHPY-UHFFFAOYSA-N		| StdInChIKey = DDWGQGZPYDSYEL-LSDHHAIUSA-N
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 1617-53-4
			| CASNo = 26543-89-5
	| PubChem = 5281600		| PubChem = 442879
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 63354		| ChEMBL = 242011
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 391188
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| SMILES = C1C(C(C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
	| ChemSpiderID = 4444919
			| InChI = 1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1
			}}
	| SMILES = O=C1\C=C(/Oc2cc(O)cc(O)c12)c6cc(c5c(O)cc(O)c3c5O/C(=C\C3=O)c4ccc(O)cc4)c(O)cc6
			| Section2 = {{Chembox Properties
			| C=20| H=18 | O=6
	| InChI = 1/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
			| Appearance =
			| Density =
			| MeltingPt =
			| BoilingPt =
			| Solubility =
			}}
			| Section3 = {{Chembox Hazards
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
			}}
			| Section4 =
			| Section5 =
			| Section6 =
	}}		}}
			'''Hinokinin''' is a dibenzylbutyrolactone ], derived from various species of plants. It is a potential ] agent.<ref name=":0">{{Cite journal|last1=Marcotullio|first1=Maria|last2=Pelosi|first2=Azzurra|last3=Curini|first3=Massimo|date=2014-09-17|title=Hinokinin, an Emerging Bioactive Lignan|journal=Molecules|volume=19|issue=9|pages=14862–14878|doi=10.3390/molecules190914862|pmid=25232707|pmc=6271885|issn=1420-3049|doi-access=free}}</ref> '']'', it has been shown to have potential ] effects<ref>{{Cite journal|last1=Timple|first1=Julie Marie V.|last2=Magalhães|first2=Lizandra Guidi|last3=Souza Rezende|first3=Karen Cristina|last4=Pereira|first4=Ana Carolina|last5=Cunha|first5=Wilson Roberto|last6=Andrade e Silva|first6=Márcio Luis|last7=Mortensen|first7=Ole Valente|last8=Fontana|first8=Andréia C. K.|date=2013-10-10|title=The Lignan (−)-Hinokinin Displays Modulatory Effects on Human Monoamine and GABA Transporter Activities|journal=Journal of Natural Products|volume=76|issue=10|pages=1889–1895|doi=10.1021/np400452n|pmid=24112084|issn=0163-3864}}</ref> as well as ], anti-tumor, ] and ] properties.<ref>{{Cite journal|last1=Zhou|first1=Qi-Long|last2=Wang|first2=Hui-Jing|last3=Tang|first3=Pei|last4=Song|first4=Hao|last5=Qin|first5=Yong|date=October 2015|title=Total Synthesis of Lignan Lactone (–)-Hinokinin|journal=Natural Products and Bioprospecting|volume=5|issue=5|pages=255–261|doi=10.1007/s13659-015-0073-3|pmid=26458924|pmc=4607678|issn=2192-2195|doi-access=free}}</ref>
	| Section2 = {{Chembox Properties
			Hinokinin was isolated for the first time by Yoshiki and Ishiguro in 1933 from ] wood.<ref>{{Cite journal|last1=Yoshiki|first1=Y.|last2=Ishiguro|first2=T.|date=1933|title=Ueber die kristallisierten Bestandteile des Hinokiöls|journal=Yakugaku Zasshi|volume=53|issue=2|pages=73–151|doi=10.1248/yakushi1881.53.2_73|issn=0031-6903|doi-access=free}}</ref>
	| Formula = C<sub>30</sub>H<sub>18</sub>O<sub>10</sub>
	| MolarMass = 538.45 g/mol
	| ExactMass = 538.089997
			==Chemical properties==
	| Appearance =
			Hinokinin is a colourless crystalline compound.{{cn|date=January 2023}}
	| Density =
	| MeltingPt =
			It can be isolated from various species of '']'', '']'', '']'', '']'', '']'', '']'', '']'' and '']''. It is also synthesised from ].<ref name=":0" />
	| BoilingPt =
			==Biological effects==
	| Solubility =
			===Cytotoxic actions===
	}}
			Hinokinin has shown to induce ] and promote antitumor actions on various cancer cell lines ''in vitro''.<ref>{{Cite journal|last1=Cao|first1=Xue-li|last2=Xu|first2=Jing|last3=Bai|first3=Ge|last4=Zhang|first4=Hong|last5=Liu|first5=Yan|last6=Xiang|first6=Jun-feng|last7=Tang|first7=Ya-lin|date=June 2013|title=Isolation of anti-tumor compounds from the stem bark of Zanthoxylum ailanthoides Sieb. & Zucc. by silica gel column and counter-current chromatography|journal=Journal of Chromatography B|volume=929|pages=6–10|doi=10.1016/j.jchromb.2013.04.006|pmid=23660246|issn=1570-0232}}</ref>
			===Anti-inflammatory actions===
	| Section3 = {{Chembox Hazards
			Hinokinin has been shown to inhibit the generation of superoxide molecules by ]s and also decreases ] secretion from neutrophils.<ref>{{Cite journal|last1=Chen|first1=JJ|last2=Chung|first2=CY|last3=Hwang|first3=TL|last4=Chen|first4=JF|date=July 2009|title=Amides and Benzenoids from Zanthoxylum ailanthoides with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils|journal=Planta Medica|volume=75|issue=9|doi=10.1055/s-0029-1234991|issn=0032-0943}}</ref> It has also shown to reduce LPS induced ] production from ]s.The ] property of hinokinin is mediated by the ] signalling mechanism.<ref>{{Cite journal|last1=Desai|first1=Dattatraya C.|last2=Jacob|first2=Jeenu|last3=Almeida|first3=Asha|last4=Kshirsagar|first4=Rajendra|last5=Manju|first5=S.L.|date=2014-05-23|title=Isolation, structural elucidation and anti-inflammatory activity of astragalin, ( − )hinokinin, aristolactam I and aristolochic acids (I & II) fromAristolochia indica|journal=Natural Product Research|volume=28|issue=17|pages=1413–1417|doi=10.1080/14786419.2014.905563|pmid=24854204|s2cid=20632496|issn=1478-6419}}</ref>
			===Anti-parasitic actions===
	| MainHazards =
			Hinokinin has been shown to be an antitrypanosomal agent. Its use as a treatment for ] is still being researched.<ref>{{Cite journal|last1=Saraiva|first1=Juliana|last2=Lira|first2=Ana Amélia Moreira|last3=Esperandim|first3=Viviane Rodrigues|last4=da Silva Ferreira|first4=Daniele|last5=Ferraudo|first5=Antônio Sérgio|last6=Bastos|first6=Jairo Kenupp|last7=e Silva|first7=Márcio Luís Andrade|last8=de Gaitani|first8=Cristiane Masetto|last9=de Albuquerque|first9=Sérgio|last10=Marchetti|first10=Juliana Maldonado|date=2010-01-28|title=(−)−Hinokinin-loaded poly(<small>D</small>,<small>L</small>-lactide-co-glycolide) microparticles for Chagas disease|journal=Parasitology Research|volume=106|issue=3|pages=703–708|doi=10.1007/s00436-010-1725-1|pmid=20107838|s2cid=31990739|issn=0932-0113}}</ref>
			===Anti-viral actions===
	| FlashPt =
			It has shown significant antiviral activity against human ] virus, ] and ].<ref>{{Cite journal|last1=Wen|first1=Chih-Chun|last2=Kuo|first2=Yueh-Hsiung|last3=Jan|first3=Jia-Tsrong|last4=Liang|first4=Po-Huang|last5=Wang|first5=Sheng-Yang|last6=Liu|first6=Hong-Gi|last7=Lee|first7=Ching-Kuo|last8=Chang|first8=Shang-Tzen|last9=Kuo|first9=Chih-Jung|last10=Lee|first10=Shoei-Sheng|last11=Hou|first11=Chia-Chung|date=August 2007|title=Specific Plant Terpenoids and Lignoids Possess Potent Antiviral Activities against Severe Acute Respiratory Syndrome Coronavirus|journal=Journal of Medicinal Chemistry|volume=50|issue=17|pages=4087–4095|doi=10.1021/jm070295s|pmid=17663539|issn=0022-2623|url=http://ntur.lib.ntu.edu.tw/bitstream/246246/162827/1/05.pdf }}</ref>
			==See also==
	| Autoignition =
			* ]
	}}
	}}
	'''Amentoflavone''' is a constituent of a number of plants with medicinal properties, including ] and ] (St. John’s Wort).<ref>{{cite journal |author=Pan X, Tan N, Zeng G, Zhang Y, Jia R |title=Amentoflavone and its derivatives as novel natural inhibitors of human Cathepsin B |journal=Bioorg. Med. Chem. |volume=13 |issue=20 |pages=5819–25 |year=2005 |month=October |pmid=16084098 |doi=10.1016/j.bmc.2005.05.071 |url=}}</ref>
	It is a biflavonoid (bis-] coupled at 8 and 3' positions).
	Amentoflavone can interact with many other medications by being a potent inhibitor of ] and ], which are proteins used for drug metabolism in the body.<ref>{{cite journal |author=Kimura Y, Ito H, Ohnishi R, Hatano T |title=Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity |journal=Food Chem. Toxicol. |volume=48 |issue=1 |pages=429–35 |year=2010 |month=January |pmid=19883715 |doi=10.1016/j.fct.2009.10.041 |url=}}</ref>
	==References==		==References==
	{{Reflist}}		{{Reflist}}
	]		]
	]		]
			]
			]
	{{Medicine-stub}}
			]
	{{Polyphenol-stub}}
			]
			]