Barbigerone
| Barbigerone | |
|---|---|
| File:Barbigerone.png | |
| 3-(2,4,5-Trimethoxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b :3,4-b ']dipyran-4-one | |
| Other names Barubigeron; 2′,4′,5′-trimethoxy-6″,6″-dimethylpyrano(2″,3″:7,8)isoflavone | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 75425-27-3 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C23H22O6 |
| Molar mass | 394.42 g mol−1 |
| Exact mass | 394.14163 |
| 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
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- Jump up ↑ 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.
- Jump up ↑ 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. PMID 19140097.
- Jump up ↑ Dagne E, Bekele A (1990). "C-prenylated isoflavones from Millettia ferruginea". Phytochemistry. 29 (8): 2679–2682. doi:10.1016/0031-9422(90)85212-X.
- Jump up ↑ 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.
- Jump up ↑ 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. doi:10.1002/jssc.200900641. PMID 20187026. External link in
|title=(help) - Jump up ↑ Wangensteen H, Alamgir M, Rajia S, Samuelsen AB, Malterud KE (2005). "Rotenoids and isoflavones from Sarcolobus globosus". Planta Med. 71 (8): 754–758. PMID 16142641.
- Jump up ↑ 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.
- Jump up ↑ 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. PMID 13679101.
- Jump up ↑ 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. PMID 19590197.
