Barbigerone

Barbigerone
Other names

Barubigeron; 2′,4′,5′-trimethoxy-6″,6″-dimethylpyrano(2″,3″:7,8)isoflavone
Identifiers
CAS number 75425-27-3 Y=
PubChem 156793
ChemSpider 138031 Y
Jmol-3D images Image 1
Properties
Molecular formula C23H22O6
Molar mass 394.42 g mol−1
Exact mass 394.14163 u
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

References

  1. ^ Vilain C (1980). "Barbigerone,next term a new pyranoisoflavone from seeds of Tephrosia barbigera". Phytochemistry 19 (5): 988–989. doi:10.1016/0031-9422(80)85162-4. 
  2. ^ Gong T, Wang DX, Chen RY, Liu P, Yu DQ. (2009). "Novel benzil and isoflavone derivatives from Millettia dielsiana". Planta Med 75 (3): 236–242. doi:10.1055/s-0028-1112203. PMID 19140097. 
  3. ^ Dagne E, Bekele A (1990). "C-prenylated isoflavones from Millettia ferruginea". Phytochemistry 29 (8): 2679–2682. doi:10.1016/0031-9422(90)85212-X. 
  4. ^ Yenesew A, Midiwo JO, Waterman PG (1998). "Rotenoids, isoflavones and chalcones from the stem bark of Millettia usaramensis subspecies usaramensis". Phytochemistry 47 (2): 295–300. doi:10.1016/S0031-9422(97)00424-X. 
  5. ^ Ye H, Zhong S, Li Y, Tang M, Peng A, Hu J, Shi J, He S, Wu W, Chen L (2010). "Enrichment and isolation of barbigerone from Millettia pachycarpa Benth. using high-speed counter-current chromatography and preparative HPLC". J Sep Sci 33 (8): 1010–7. doi:10.1002/jssc.200900641. PMID 20187026. http://www3.interscience.wiley.com/journal/123301902/abstract. 
  6. ^ Wangensteen H, Alamgir M, Rajia S, Samuelsen AB, Malterud KE (2005). "Rotenoids and isoflavones from Sarcolobus globosus". Planta Med 71 (8): 754–758. doi:10.1055/s-2005-864182. PMID 16142641. 
  7. ^ 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.2006.03.0171. PMID 16701962. 
  8. ^ 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. 
  9. ^ 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". Cell Physiol Biochem. 24 (1–2): 95–104. doi:10.1159/000227817. PMID 19590197. 

External links

Isoflavones and their glycosides
Isoflavones
Daidzein | Genistein | Irilone |Orobol | Pseudobaptigenin | Anagyroidisoflavone A and B
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Bidwillol A | Derrubone | Luteone | Wighteone
Pyranoisoflavones
Alpinumisoflavone | Barbigerone | Di-O-methylalpinumisoflavone | 4'-methyl-alpinumisoflavone
Misc
Synthetic