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Barbigerone

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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 C23H22O6
Molar mass 394 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) 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 are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.

References

  1. 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.
  2. 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.
  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, 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.
  5. 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.
  6. 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.
  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.2006.03.017. 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". Cellular Physiology and Biochemistry. 24 (1–2): 95–104. doi:10.1159/000227817. PMID 19590197.

External links

Isoflavones and their glycosides
Isoflavones
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
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