| 词条 | Barbigerone |
| 释义 |
| Watchedfields = changed | verifiedrevid = 461217985 | ImageFile = Barbigerone.png | ImageSize = 200px | IUPACName = 3-(2,4,5-Trimethoxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b :3,4-b ']dipyran-4-one | OtherNames = Barubigeron; 2′,4′,5′-trimethoxy-6″,6″-dimethylpyrano(2″,3″:7,8)isoflavone |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}}= | CASNo = 75425-27-3 | MeSHName = C543999 | PubChem = 156793 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 138031 | SMILES = O=C3C(=C/Oc2c1\\C=C/C(Oc1ccc23)(C)C)\\c4cc(OC)c(OC)cc4OC | InChI = 1/C23H22O6/c1-23(2)9-8-13-17(29-23)7-6-14-21(24)16(12-28-22(13)14)15-10-19(26-4)20(27-5)11-18(15)25-3/h6-12H,1-5H3 | InChIKey = OBIUGMGQVQMVSK-UHFFFAOYAE | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C23H22O6/c1-23(2)9-8-13-17(29-23)7-6-14-21(24)16(12-28-22(13)14)15-10-19(26-4)20(27-5)11-18(15)25-3/h6-12H,1-5H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OBIUGMGQVQMVSK-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=23 | H=22 | O=6 | MolarMass = 394 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone".[1] Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena,[2] M. ferruginea,[3] M. usaramensis,[4] and M. pachycarpa.[5] It has also been isolated from the medicinal plant Sarcolobus globosus.[6] Barbigerone from S. globosus is validated to have significant antioxidant property.[7] Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum.[8] It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.[9] References1. ^{{cite journal |author=Vilain C |year=1980 |title=Barbigerone, next term a new pyranoisoflavone from seeds of Tephrosia barbigera |journal=Phytochemistry |volume=19 |issue=5 |doi=10.1016/0031-9422(80)85162-4 |pages=988}} 2. ^{{cite journal |doi=10.1055/s-0028-1112203 |author= |title=Novel benzil and isoflavone derivatives from Millettia dielsiana |pages=236–242 |pmid=19140097 |year=2009 |last1=Gong |first1=Ting |last2=Wang |first2=Dong-Xiao |last3=Chen |first3=Ruo-Yun |last4=Liu |first4=Ping |last5=Yu |first5=De-Quan |journal=Planta Medica |volume=75 |issue=3}} 3. ^{{cite journal |author=Dagne E, Bekele A |year=1990 |title=C-prenylated isoflavones from Millettia ferruginea |journal=Phytochemistry |volume=29 |issue=8 |pages=2679–2682 |doi=10.1016/0031-9422(90)85212-X}} 4. ^{{cite journal |title=Rotenoids, isoflavones and chalcones from the stem bark of Millettia usaramensis subspecies usaramensis |journal=Phytochemistry |doi=10.1016/S0031-9422(97)00424-X |year=1998 |last1=Yenesew |first1=Abiy |last2=Midiwo |first2=Jacob O. |last3=Waterman |first3=Peter G. |volume=47 |issue=2 |pages=295}} 5. ^{{cite journal |title=Enrichment and isolation of barbigerone from Millettia pachycarpa Benth. using high-speed counter-current chromatography and preparative HPLC |pmid=20187026 |doi=10.1002/jssc.200900641 |url=http://www3.interscience.wiley.com/journal/123301902/abstract |archive-url=https://archive.today/20130105080935/http://www3.interscience.wiley.com/journal/123301902/abstract |dead-url=yes |archive-date=2013-01-05 |year=2010 |last1=Ye |first1=Haoyu |last2=Zhong |first2=Shijie |last3=Li |first3=Yanfang |last4=Tang |first4=Minghai |last5=Peng |first5=Aihua |last6=Hu |first6=Jia |last7=Shi |first7=Jie |last8=He |first8=Shicao |last9=Wu |first9=Wenshuang |last10=Chen |first10=Lijuan |journal=Journal of Separation Science |pages=1010–7 |volume=33 |issue=8}} 6. ^{{cite journal |title=Rotenoids and isoflavones from Sarcolobus globosus |pages=754–758 |pmid=16142641 |year=2005 |last1=Wangensteen |first1=H |last2=Alamgir |first2=M |last3=Rajia |first3=S |last4=Samuelsen |first4=AB |last5=Malterud |first5=KE |volume=71 |issue=8 |doi=10.1055/s-2005-864182 |journal=Planta Medica}} 7. ^{{cite journal |title=Antioxidant and 15-lipoxygenase inhibitory activity of rotenoids, isoflavones and phenolic glycosides from Sarcolobus globosus |journal=Fitoterapia |pmid=16701962 |volume=77 |issue=4 |pages=290–295 |doi=10.1016/j.fitote.2006.03.017 |year=2006 |last1=Wangensteen |first1=H |last2=Miron |first2=A |last3=Alamgir |first3=M |last4=Rajia |first4=S |last5=Samuelsen |first5=AB |last6=Malterud |first6=KE}} 8. ^{{cite journal |title=Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis |journal=Phytochemistry |volume=64 |issue=3 |pages=773–779 |pmid=13679101 |doi=10.1016/S0031-9422(03)00373-X |year=2003 |last1=Yenesew |first1=A |last2=Derese |first2=S |last3=Midiwo |first3=JO |last4=Oketch-Rabah |first4=HA |last5=Lisgarten |first5=J |last6=Palmer |first6=R |last7=Heydenreich |first7=M |last8=Peter |first8=MG |last9=Akala |first9=H |last10=Wangui |first10=J |last11=Liyala |first11=P |last12=Waters |first12=NC}} 9. ^{{cite journal |title=Barbigerone, a natural isoflavone, induces apoptosis in murine lung-cancer cells via the mitochondrial apoptotic pathway |volume=24 |issue=1–2 |pages=95–104 |pmid=19590197 |year=2009 |last1=Li |first1=ZG |last2=Zhao |first2=YL |last3=Wu |first3=X |last4=Ye |first4=HY |last5=Peng |first5=A |last6=Cao |first6=ZX |last7=Mao |first7=YQ |last8=Zheng |first8=YZ |last9=Jiang |first9=PD |last10=Zhao |first10=X |last11=Chen |first11=LJ |last12=Wei |first12=YQ |doi=10.1159/000227817 |journal=Cellular Physiology and Biochemistry}} External links
3 : Isoflavones|Flavonoid antioxidants|Chemopreventive agents |
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