Prenylated Dibenzoylmethane Derivatives from the Root of Glycyrrhiza inflata(Xinjiang Licorice).

A dibenzoylmethane derivative protects dopaminergic neurons against both oxidative stress and endoplasmic reticulum stress

“…DBM and its derivatives are small ␤-diketone compounds and are minor constituents of licorice (8). Several beneficial bioactivities of DBM, such as anti-tumor activity (21,27,31), anti-inflammatory activity (18), anti-mutagenesis (7), and iron chelation (44), have previously been reported.…”

An Efficient and Concise Synthesis of Biologically Interesting Natural Flemichapparin A, Flemingin A, Flemingin D, and Their Non-natural Analogues

“…To a solution of 24 (69 mg, 0.2 mmol) in ethanol (10 mL) was added potassim hydroxide (56 mg, 1.0 mmol) and 25 (50 mg, 0.3 mmol) at room temperature. The reaction mixture was stirred at room temperature for 48 h. Evaporation of ethanol and extraction with ethyl acetate (3 × 50 mL), washing with 2 N HCl solution and brine, drying over MgSO 4 and removal of the solvent followed by flash column chromatography on silica gel gave 28 (74 mg, 75%) as an oil: 1 H NMR (300 MHz, CDCl 3 ) δ 13.56 (1H, s), 8.18 (1H,d,J = 15.4 Hz), (2H, m), 7.52 (1H,s),7.34 (1H,t,J = 7.6 Hz),7.17 (1H,d,J = 7.6 Hz),7.03 (1H,t,J = 8. 2928,1634,1568,1476,1362,1283,1157,1082,1046,988,926,756 2928, 1636, 1568, 1510, 1474, 1372, 1289, 1242, 1155, 1082, 1046, 995, 926, 831, 731 cm 9, 155.2, 147.2, 144.3, 136.7, 134.8, 132.2, 130.6, 129.0, 128.9, 128.5, 128.4, 127.0, 123.5, 120.4, 116.6, 113.5, 112.7, 109.3, 81.7, 41.5, 27.2, 25.6, 22.7, 17.6;IR (KBr) 3418, 2971, 2926, 1644, 1576, 1478, 1394, 1296, 1169 Flemingin A (5). To a solution of 28 (54 mg, 0.11 mmol) in methanol (10 mL) was added 3 N HCl (10 drops) and the reaction mixture was heated at 50 o C for 1 h. 192.9, 156.0, 155.2, 147.4, 140.5, 136.6, 132.1, 131.8, 130.0, 126.9, 123.5, 122.1, 121.0, 120.8, 116.6, 116.5, 113.9, 112.8, 109.3, 81.7, 41.5, 27.2, 25.6, 22.7, 17.6;IR (KBr) 3385, 2972, 1626, m 1479, 1395…”

Phenolic Constituents of Licorice (Glycyrrhiza Species)

“…A prenylflavone, licoflavone C (227),* and a dibenzoylmethane, glycyrdione B (228), have also been isolated together with two reversely constructed chalcones, licochalcones C (229) and D (230), by KAJIYAMA et al (302)(303)(304). A prenylated pyranochalcone (231) and a neoflavone, inflacoumarin A (232), have also been reported (305-307).…”

“…Glyinflanin D (219) G. inflata root (295) Glyinflanin E (220) G. inflata root (299) Glyinflanin F (221) G. inflata root (299) Glycyrdione B (228) G. inflata root (303) Kanzonol A (236) G. eurycarpa root (294) 5'-Prenyllicodione (243) G. inflata root (303) G. eurycarpa root (294) G. echinata (callus) (86,366) 2'-O-Methyllicodione (246) G. pallidiflora root (312,315) synthesis (314) synthesis (CMR) (365) Licodione (305) C. echinata (callus) (364,367) C. pallidiflora root (315) synthesis (CMR)…”

“…Glepidotin B (303) G. lepidota whole part (360) (3-H ydroxyflavanone) Eriodictyol (316) G. eurycarpa aerial part (359) No name (309) G. eurycarpa aerial part (359) '" No name (337) G. glabra (hairy root culture)…”