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Barbigerone

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Barbigerone
Names
IUPAC name 3-(2,4,5-Trimethoxyphenyl)-8,8-dimethyl-4H,8H-benzodipyran-4-one
Other names Barubigeron; 2′,4′,5′-trimethoxy-6″,6″-dimethylpyrano(2″,3″:7,8)isoflavone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
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): 988–989. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

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