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Revision as of 02:43, 18 November 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit Latest revision as of 19:27, 29 April 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits move systematic name 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 431672894 | verifiedrevid = 461217985
| ImageFile = Barbigerone.png | ImageFile = Barbigerone.png
| ImageSize = 200px | ImageSize = 200px
| IUPACName = 3-(2,4,5-Trimethoxyphenyl)-8,8-dimethyl-4''H'',8''H''-benzodipyran-4-one | IUPACName = 2′,4′,5′-Trimethoxy-6′′,6′′-dimethyl-6′′''H''-pyranoisoflavone
| SystematicName = 8,8-Dimethyl-3-(2,4,5-trimethoxyphenyl)-4''H'',8''H''-benzodipyran-4-one
| IUPACName_hidden = yes
| OtherNames = Barubigeron; 2′,4′,5′-trimethoxy-6″,6″-dimethylpyrano(2″,3″:7,8)isoflavone | OtherNames = Barubigeron
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}= | CASNo_Ref = {{cascite|correct|??}}=
| CASNo = 75425-27-3 | CASNo = 75425-27-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | MESH = C543999
| PubChem = 156793 | UNII = 9BE3F2B4GD
⚫ | MeSHName = C543999
⚫ | ChemSpiderID = 138031
| PubChem = 156793
| SMILES = O=C3C(=C/Oc2c1\C=C/C(Oc1ccc23)(C)C)\c4cc(OC)c(OC)cc4OC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | 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
⚫ | ChemSpiderID = 138031
⚫ | InChIKey = OBIUGMGQVQMVSK-UHFFFAOYAE
| 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 | 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
| StdInChIKey = OBIUGMGQVQMVSK-UHFFFAOYSA-N | 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 |Section2={{Chembox Properties
| C=23 | H=22 | O=6 | C=23 | H=22 | O=6
| MolarMass = 394 g/mol | MolarMass = 394 g/mol
| ExactMass = 394.14163 u
| Appearance = | Appearance =
| Density = | Density =
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| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


'''Barbigerone''' is one of a few ]s among several groups of ]. It was first isolated from the seed of a ] ''Tephrosia barbigera''; hence the name "barbigerone".<ref>{{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 |pages=988–989 |doi=10.1016/0031-9422(80)85162-4}}</ref> Members of the ] '']'' are now known to be rich in barbigerone, including ''M. dielsiena'',<ref>{{cite journal |doi=10.1055/s-0028-1112203 |author=Gong T, Wang DX, Chen RY, Liu P, Yu DQ. |year=2009 |title=Novel benzil and isoflavone derivatives from ''Millettia dielsiana'' |journal=Planta Med |volume=75 |issue=3 |pages=236–242 |pmid=19140097}}</ref> ''M. ferruginea'',<ref>{{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}}</ref> ''M. usaramensis'',<ref>{{cite journal |author=Yenesew A, Midiwo JO, Waterman PG |year=1998 |title=Rotenoids, isoflavones and chalcones from the stem bark of ''Millettia usaramensis'' subspecies ''usaramensis'' |journal=Phytochemistry |volume=47 |issue=2 |pages=295–300 |doi=10.1016/S0031-9422(97)00424-X}}</ref> and '']''.<ref>{{cite journal |author=Ye H, Zhong S, Li Y, Tang M, Peng A, Hu J, Shi J, He S, Wu W, Chen L |year=2010 |pages=1010–7 |issue=8 |title=Enrichment and isolation of barbigerone from ''Millettia pachycarpa'' Benth. using high-speed counter-current chromatography and preparative HPLC |volume=33 |journal=J Sep Sci |pmid=20187026 |doi=10.1002/jssc.200900641 |url=http://www3.interscience.wiley.com/journal/123301902/abstract}}</ref> It has also been isolated from the medicinal plant '']''.<ref>{{cite journal |doi=10.1055/s-2005-864182 |author=Wangensteen H, Alamgir M, Rajia S, Samuelsen AB, Malterud KE |year=2005 |title=Rotenoids and isoflavones from ''Sarcolobus globosus'' |journal=Planta Med |volume=71 |issue=8 |pages=754–758 |pmid=16142641}}</ref> Barbigerone from ''S. globosus'' is validated to have significant ] property.<ref>{{cite journal |author=Wangensteen H, Miron A, Alamgir M, Rajia S, Samuelsen AB, Malterud KE |year=2006 |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.2006.03.0171}}</ref> Barbigerone exhibits profound antiplasmodial activity against the ] '']''.<ref>{{cite journal |doi=10.1016/S0031-9422(03)00373-X |author=Yenesew A, Derese S, Midiwo JO, Oketch-Rabah HA, Lisgarten J, Palmer R, Heydenreich M, Peter MG, Akala H, Wangui J, Liyala P, Waters NC |year=2003 |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}}</ref> It is also demonstrated that it has ] potential as it causes ] of ] ].<ref>{{cite journal |doi=10.1159/000227817 |author=Li ZG, Zhao YL, Wu X, Ye HY, Peng A, Cao ZX, Mao YQ, Zheng YZ, Jiang PD, Zhao X, Chen LJ, Wei YQ |year=2009 |title=Barbigerone, a natural isoflavone, induces apoptosis in murine lung-cancer cells via the mitochondrial apoptotic pathway |journal=Cell Physiol Biochem. |volume=24 |issue=1–2 |pages=95–104 |pmid=19590197}}</ref> '''Barbigerone''' is one of a few ]s among several groups of ]. It was first isolated from the seed of a ] ''Tephrosia barbigera''; hence the name "barbigerone".<ref>{{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}}</ref> Members of the ] '']'' are now known to be rich in barbigerone, including ''M. dielsiena'',<ref>{{cite journal |doi=10.1055/s-0028-1112203 |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}}</ref> ''M. ferruginea'',<ref>{{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}}</ref> ''M. usaramensis'',<ref>{{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}}</ref> and '']''.<ref>{{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 |url-status=dead |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}}</ref> It has also been isolated from the medicinal plant '']''.<ref>{{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}}</ref> Barbigerone from ''S. globosus'' is validated to have significant ] property.<ref>{{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}}</ref> Barbigerone exhibits profound antiplasmodial activity against the ] '']''.<ref>{{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}}</ref> It is also demonstrated that it has ] potential as it causes ] of ] ].<ref>{{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|doi-access=free }}</ref>


== References == == References ==
{{Reflist}} {{Reflist}}


== External links == ==External links==
*{{Commonscat-inline}}
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{{isoflavone}} {{isoflavone}}


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