Barbigerone

Barbigerone
Names
	IUPAC name 2′,4′,5′-Trimethoxy-6′′,6′′-dimethyl-6′′H-pyrano[2′′,3′′:7,8]isoflavone
	Systematic IUPAC name 8,8-Dimethyl-3-(2,4,5-trimethoxyphenyl)-4H,8H-benzo[1,2-b:3,4-b′]dipyran-4-one
	Other names Barubigeron
Identifiers
CAS Number	75425-27-3 =;
3D model (JSmol)	Interactive image;
ChemSpider	138031 ;
MeSH	C543999
PubChem CID	156793;
UNII	9BE3F2B4GD ;
CompTox Dashboard (EPA)	DTXSID30226352 ;
	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,1-5H3 Key: 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,1-5H3 Key: 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 [77 °F], 100 kPa). verify (what is ?) 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

^ 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.

External links

Media related to Barbigerone at Wikimedia Commons
Metabolome
J-Global

[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.

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