词条 | Flavones | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
释义 |
Flavones are common in the food supply, mainly from spices, and red–purple fruits and vegetables.[1] Common flavones include apigenin (4',5,7-trihydroxyflavone), luteolin (3',4',5,7-tetrahydroxyflavone), tangeritin (4',5,6,7,8-pentamethoxyflavone), chrysin (5,7-dihydroxyflavone), and 6-hydroxyflavone.[1] Intake and eliminationFlavones are mainly found in spices and red or purple plant foods.[1] The estimated daily intake of flavones is about 2 mg per day.[1] Flavones have no proven physiological effects in the human body and no antioxidant food value.[1][3] Following ingestion and metabolism, flavones, other polyphenols, and their metabolites are absorbed poorly in body organs and are rapidly excreted in the urine, indicating mechanisms influencing their presumed absence of metabolic roles in the body.[1][4] Drug interactionsFlavones have effects on CYP (P450) activity [5][6] which are enzymes that metabolize most drugs in the body. Organic chemistryIn organic chemistry several methods exist for the synthesis of flavones:
Another method is the dehydrative cyclization of certain 1,3-diaryl diketones.[7] {{anchor|Wessely-Moser rearrangement}} Wessely–Moser rearrangementThe Wessely–Moser rearrangement (1930)[8] has been an important tool in structure elucidation of flavonoids. It involves the conversion of 5,7,8-trimethoxyflavone into 5,6,7-trihydroxyflavone on hydrolysis of the methoxy groups to phenol groups. It also has synthetic potential for example:[9] This rearrangement reaction takes place in several steps: A ring opening to the diketone, B bond rotation with formation of a favorable acetylacetone-like phenyl-ketone interaction and C hydrolysis of two methoxy groups and ring closure. Common flavones
References1. ^1 2 3 4 5 6 {{cite web|url=http://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/flavonoids|title=Flavonoids|publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR|date=November 2015|accessdate=30 March 2018}} 2. ^{{cite web|url=http://www.chemspider.com/Chemical-Structure.10230.html|title=Flavone|publisher=ChemSpider, Royal Society of Chemistry|date=2015|accessdate=30 March 2018}} 3. ^{{cite journal |last1=Lotito |first1=S |last2=Frei |first2=B |title=Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: Cause, consequence, or epiphenomenon? |journal=Free Radical Biology and Medicine |volume=41 |issue=12 |pages=1727–46 |year=2006 |pmid=17157175 |doi=10.1016/j.freeradbiomed.2006.04.033}} 4. ^{{cite web|url=http://www.eurekalert.org/pub_releases/2007-03/osu-sfn030507.php|title=Studies force new view on biology of flavonoids|author=David Stauth|publisher=EurekAlert!; Adapted from a news release issued by Oregon State University|date=5 March 2007}} 5. ^Cermak R, Wolffram S., The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms,Curr Drug Metab. 2006 Oct;7(7):729-44. 6. ^{{cite journal |vauthors=Si D, Wang Y, Zhou YH |title=Mechanism of CYP2C9 inhibition by flavones and flavonols |journal=Drug Metab. Dispos. |volume=37 |issue=3 |pages=629–34 |date=March 2009 |pmid=19074529 |doi=10.1124/dmd.108.023416 |url=http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=19074529|display-authors=etal}} 7. ^{{cite journal |vauthors=Sarda SR, Pathan MY, Paike VV, Pachmase PR, Jadhav WN, Pawar RP |title=A facile synthesis of flavones using recyclable ionic liquid under microwave irradiation |journal=Arkivoc |volume=xvi |issue= 16|pages=43–8 |year=2006 |doi= 10.3998/ark.5550190.0007.g05|url=http://www.arkat-usa.org/ARKIVOC/JOURNAL_CONTENT/manuscripts/2006/06-2210HP%20as%20published%20mainmanuscript.pdf}} 8. ^{{cite journal |vauthors=Wessely F, Moser GH |title=Synthese und Konstitution des Skutellareins |journal=Monatsh. Chem. |volume=56 |issue=1 |pages=97–105 |date=December 1930 |doi=10.1007/BF02716040 |url=http://www.springerlink.com/content/p61843913k3350l3/?p=b310e8658f3c400c8b382dbd980a1cdd&pi=7}} 9. ^{{cite journal |vauthors=Larget R, Lockhart B, Renard P, Largeron M |title=A convenient extension of the Wessely-Moser rearrangement for the synthesis of substituted alkylaminoflavones as neuroprotective agents in vitro |journal=Bioorg. Med. Chem. Lett. |volume=10 |issue=8 |pages=835–8 |date=April 2000 |pmid=10782697 |url=http://linkinghub.elsevier.com/retrieve/pii/S0960-894X(00)00110-4 |doi=10.1016/S0960-894X(00)00110-4}} 10. ^{{Cite book|title=The Flavonoids - Springer|doi=10.1007/978-1-4899-2909-9|year = 1975|isbn = 978-0-12-324602-8|last1 = Harborne|first1 = Jeffrey B.|last2=Marby|first2=Helga|last3=Marby|first3=T. J.}} External links
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