| Identification | Back Directory | [Name]
sigmoidin B | [CAS]
87746-47-2 | [Synonyms]
sigmoidin B
(S)-2-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-[3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-2,3-dihydro-5,7-dihydroxy-, (2S)- | [Molecular Formula]
C20H20O6 | [MOL File]
87746-47-2.mol | [Molecular Weight]
356.37 |
| Hazard Information | Back Directory | [Uses]
Sigmoidin B, a prenylated flavanone, is a selective 5-lipoxygenase inhibitor. Sigmoidin B is a potent scavenger of the DPPH radical. Sigmoidin B has antigenotoxic activity that inhibits genotoxicity induced by Aflatoxin B1 (HY-N6615), with an IC50 of 18.7 μg/mL. Sigmoidin B has anti-inflammatory activity and antioxidant properties[1][2]. | [Definition]
ChEBI: A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and a prenyl group at position 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant acti
ities. | [in vivo]
In the assay of phospholipase A2-induced mouse paw oedema, Sigmoidin B (5 mg/kg, ip) inhibits oedema formation at 60 min. In the Phorbol 12-myristate 13-acetate (PMA) (HY-18739) test, Sigmoidin B decreases the induced oedema by 83%[1]. | [IC 50]
5-Lipoxygenase | [References]
[1] Njamen D, et al. Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Planta Med. 2004 Feb;70(2):104-7. DOI:10.1055/s-2004-815484
[2] Zarev Y, et al. Antigenotoxic prenylated flavonoids from stem bark of Erythrina latissima. Phytochemistry. 2017 Sep;141:140-146. DOI:10.1016/j.phytochem.2017.06.003 |
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