Flavonoid constituents of Zingiber zerumbet Smith.

Constituents of Zingiber aromaticum and Their CYP3A4 and CYP2D6 Inhibitory Activity

“…Each fraction was separated by repeated column chromatography and preparative TLC to give 16 compounds. Their structures were elucidated on the basis of spectroscopic analyses, to be a new sesquiterpene [2,9-humuladien-6-ol-8-one (1)], three known humulane-type sesquiterpenes [zerumbone, 8,10) zerumbone epoxide, 10) tricyclohumuladiol 11) ], three gingerols [(S)-6-gingerol, 12,13) (S)-8-gingerol, 13) (S)-10-gingerol 13) ], two shogaols [trans-6-shogaol, 14) trans-10-shogaol 15) ], two flavonoids [kaempferol-3-O-methyl ether, 16) kaempferol-3,4Ј-di-O-methyl ether 16) ], two acetylated flavonol glycosides 17) b-sitosterol, 18) and b-sitosterol glucoside. 19) Among the known compounds, trycyclohumuladiol (2), (S)-8-gingerol (3), (S)-10-gingerol (4), trans-10-shogaol (5), and b-sitosterol glucoside (6) were found for the first time in this plant.…”

Secondary Metabolites in Fruits, Vegetables, Beverages and Other Plant‐based Dietary Components

“…Flavonoids do not generally exceed ∼0.2-0.4 g/kg in Lamiaceae herbs but reach ∼1.5-3 g/kg in Apiaceae herbs, ∼3.5 g/kg in cloves and ∼7 g/kg in bay leaf (Laurus nobilis) (Shan et al 2005). Flavonol glycosides are found in basil (Baritaux et al 1991) and ginger (Nakatani et al 1991;Kawabata et al 2003), glycosides and glucuronides of flavones in sage (Canigueral et al 1989), glycosides of the isoflavone genistein (up to 100 mg/kg) in some samples of cumin (Cuminum cymimum) (Clarke et al 2004) and glycosides of the relatively uncommon 6-hydroxyapigenin in marjoram and sage (Lu and Foo 2000;Miura et al 2002;Kawabata et al 2003). Lemongrass (Cymbopogon citratus) contains unusual C-glycosides of the flavones luteolin and chrysoeriol (Figure 7.49) as well as caffeic acid and chlorogenic acids (Cheel et al 2005).…”

Naturally Occurring Small‐Molecule Inhibitors of Hedgehog/GLI‐Mediated Transcription

“…We identified two sesquiterpenes and four bis-A C H T U N G T R E N N U N G indole alkaloids as inhibitors of GLI-mediated transcription (Scheme 1 A and B; Table 1). Sesquiterpenes zerumbone (1) [28] and zerumbone epoxide (2) [29] inhibited the transcriptional A C H T U N G T R E N N U N G activity of GLI1 with IC 50 values of 7.1 and 55 mm, respectively, whereas humulene (3), [30] buddledone A (4), [31] humulene epoxide-III (5), [32] 6-methoxy-(2E,9E)-humuladien-8-one (6), [33] humulene epoxide-II (7), [34] and humulene 2,3;6,7-diepoxide (8), [35] which have the same chemical skeletons as zerumbone, were inactive even at 25 mg mL À1 . Bisindole alkaloids staurosporinone (9), [36] 6-hydroxystaurosporinone (10), [36] arcryaflavin C (11), [37] and 5,6-dihydroxyarcyriaflavin A (12) [36] also inhibited the transcriptional activity of GLI1, with IC 50 values of 1.8, 3.6, 11.3 and 6.9 mm, respectively, whereas lycogarubin C (13), [38] lycogarubin B (14), [38] lycogarubic acid A (15), [39] and lycogarubic acid methyl ester (16) [40] were inactive even at 25 mg mL À1 .…”