Barbigerone
Names
IUPAC name
2′,4′,5′-Trimethoxy-6′′,6′′-dimethyl-6′′H -pyranoisoflavone
Systematic IUPAC name
8,8-Dimethyl-3-(2,4,5-trimethoxyphenyl)-4H ,8H -benzodipyran-4-one
Other names
Barubigeron
Identifiers
CAS Number
3D model (JSmol )
ChemSpider
MeSH
C543999
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI
InChI=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,1-5H3Key: OBIUGMGQVQMVSK-UHFFFAOYSA-N 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,1-5H3Key: OBIUGMGQVQMVSK-UHFFFAOYAE
SMILES
O=C3C(=C/Oc2c1\C=C/C(Oc1ccc23)(C)C)\c4cc(OC)c(OC)cc4OC
Properties
Chemical formula
C23 H22 O6
Molar mass
394 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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Infobox references
Chemical compound
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". Members of the genus Millettia M. dielsiena , M. ferruginea , M. usaramensis , and M. pachycarpa Sarcolobus globosus S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum anti-cancer potential as it causes apoptosis of murine lung-cancer cells .
References
Vilain C (1980). "Barbigerone, next term a new pyranoisoflavone from seeds of Tephrosia barbigera ". Phytochemistry . 19 (5): 988. doi :10.1016/0031-9422(80)85162-4 .
Gong, Ting; Wang, Dong-Xiao; Chen, Ruo-Yun; Liu, Ping; Yu, De-Quan (2009). "Novel benzil and isoflavone derivatives from Millettia dielsiana ". Planta Medica . 75 (3): 236–242. doi :10.1055/s-0028-1112203 . PMID 19140097 .
Dagne E, Bekele A (1990). "C -prenylated isoflavones from Millettia ferruginea ". Phytochemistry . 29 (8): 2679–2682. doi :10.1016/0031-9422(90)85212-X .
Yenesew, Abiy; Midiwo, Jacob O.; Waterman, Peter G. (1998). "Rotenoids, isoflavones and chalcones from the stem bark of Millettia usaramensis subspecies usaramensis ". Phytochemistry . 47 (2): 295. doi :10.1016/S0031-9422(97)00424-X .
Ye, Haoyu; Zhong, Shijie; Li, Yanfang; Tang, Minghai; Peng, Aihua; Hu, Jia; Shi, Jie; He, Shicao; Wu, Wenshuang; Chen, Lijuan (2010). "Enrichment and isolation of barbigerone from Millettia pachycarpa Benth. using high-speed counter-current chromatography and preparative HPLC" . Journal of Separation Science . 33 (8): 1010–7. doi :10.1002/jssc.200900641 . PMID 20187026 . Archived from the original on 2013-01-05.
Wangensteen, H; Alamgir, M; Rajia, S; Samuelsen, AB; Malterud, KE (2005). "Rotenoids and isoflavones from Sarcolobus globosus ". Planta Medica . 71 (8): 754–758. doi :10.1055/s-2005-864182 . PMID 16142641 .
Wangensteen, H; Miron, A; Alamgir, M; Rajia, S; Samuelsen, AB; Malterud, KE (2006). "Antioxidant and 15-lipoxygenase inhibitory activity of rotenoids, isoflavones and phenolic glycosides from Sarcolobus globosus ". Fitoterapia . 77 (4): 290–295. doi :10.1016/j.fitote.2006.03.017 . PMID 16701962 .
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 (2003). "Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis ". Phytochemistry . 64 (3): 773–779. doi :10.1016/S0031-9422(03)00373-X . PMID 13679101 .
Li, ZG; Zhao, YL; Wu, X; Ye, HY; Peng, A; Cao, ZX; Mao, YQ; Zheng, YZ; Jiang, PD; Zhao, X; Chen, LJ; Wei, YQ (2009). "Barbigerone, a natural isoflavone, induces apoptosis in murine lung-cancer cells via the mitochondrial apoptotic pathway" . Cellular Physiology and Biochemistry . 24 (1–2): 95–104. doi :10.1159/000227817 . PMID 19590197 .
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Infobox references
Media related to Barbigerone at Wikimedia Commons