Barbigerone

Last updated
Barbigerone
Barbigerone.png
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
3D model (JSmol)
ChemSpider
MeSH C543999
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: OBIUGMGQVQMVSK-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C3C(=C/Oc2c1\C=C/C(Oc1ccc23)(C)C)\c4cc(OC)c(OC)cc4OC
Properties
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Related Research Articles

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

<span class="mw-page-title-main">Tephrosin</span> Chemical compound

Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of Tephrosia purpurea and T. vogelii.

<span class="mw-page-title-main">Daidzin</span> Chemical compound

Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu and from soybean leaves.

<span class="mw-page-title-main">Ononin</span> Chemical compound

Ononin is an isoflavone glycoside, the 7-O-β-D-glucopyranoside of formononetin, which in turn is the 4'-O-methoxy derivative of the parent isoflavone daidzein.

<span class="mw-page-title-main">Apigeninidin</span> Chemical compound

Apigeninidin is a chemical compound belonging to the 3-deoxyanthocyanidins and that can be found in the Patagonian plant Ephedra frustillata and in the soybean. Apigeninidin is one of the principal pigments found in sorghum. Extremely high level of apigeninidin (49 mg/g) has been documented in sorghum leaf sheath. Like all anthocyanidins it exists in a variety of tautomers depending on pH and hydration, several of these bare the distinctive pyrylium core.

<span class="mw-page-title-main">Taxifolin</span> Chemical compound

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

<span class="mw-page-title-main">Irigenin</span> Chemical compound

Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily, and Iris kemaonensis.

The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.

<span class="mw-page-title-main">Prenylflavonoid</span>

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.

<span class="mw-page-title-main">Ergosterol peroxide</span> Chemical compound

Ergosterol peroxide (5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a steroid derivative. It has been isolated from a variety of fungi, yeast, lichens and sponges, and has been reported to exhibit immunosuppressive, anti-inflammatory, antiviral, trypanocidal and antitumor activities in vitro.

<span class="mw-page-title-main">Retusin (isoflavone)</span> Chemical compound

Retusin is an O-methylated isoflavone, a type of flavonoid. It can be found in Fabaceae species like Dipteryx odorata, in Dalbergia retusa and in Millettia nitida. It can also be found in Maackia amurensis cell cultures.

<span class="mw-page-title-main">Calycosin</span> Chemical compound

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L..

<span class="mw-page-title-main">Eupalitin</span> Chemical compound

Eupalitin is an O-methylated flavonol. It can be found in Ipomopsis aggregata.

<i>Millettia pachycarpa</i> Species of legume

Millettia pachycarpa is a perennial climbing shrub belonging to the genus Millettia. It is one of the most well known among ~150 species of Millettia, as it is widely used in traditional practices, such as for poisoning fish, agricultural pesticide, blood tonic, and treatments of cancer and infertility. The bark fiber is used for making strong ropes.

<i>Sarcolobus globosus</i> Species of shrub

Sarcolobus globosus is a twining shrub native to tropical regions of Asia including India, China, Thailand, Malaysia, Myanmar-Burma, the Philippines and Indonesia.

<span class="mw-page-title-main">Rotenoid</span>

Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many have insecticidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones.

<span class="mw-page-title-main">Pterocarpan</span> Class of chemical compounds

Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes which can be formed by coupling of the B ring to the 4-one position.

<span class="mw-page-title-main">Astringin</span> Chemical compound

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis or Picea abies.

7-<i>O</i>-Methylluteone Chemical compound

7-O-Methylluteone is a prenylated isoflavone. It can be found in the bark of Erythrina burttii.

<span class="mw-page-title-main">Isorhapontin</span> Chemical compound

Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces, in the bark of Picea sitchensis or in white spruce.

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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.