Sesquiterpene lactones from Montanoa leucantha subsp. Leucantha

Sesquiterpene Lactones from Montanoa hibiscifolia That Inhibit the Transcription Factor NF-κB

“…The molecular formula of compound 5 was deduced as C 20 H 24 O 6 from the HRCIMS (isobutane) data at m/z 361.1653 [M + H] + . 1 H NMR data agreed well with those reported for 8R-(2′-methylbutyryloxy)-9R-hydroxy-11,13dehydromontahibisciolide, 4 except for the acyl residue, which was derived from 2′,3′-epoxy-2′-methylbutyric acid. Its absolute configuration was deduced from the chemical shift of the C-4′ methyl group and tentatively assigned as 2′R,3′R.…”

“…(Asteraceae, tribe Heliantheae, subtribe Montanoinae), also called tree daisy, is an erect, little branched shrubby perennial originated from an area extending from Guatemala to Costa Rica . It is known for the occurrence of sesquiterpene lactones (Sls) of the germacranolide type as well as the unusual montahibisciolides. − In continuation of our search for Sls with potential antiinflammatory activity we reinvestigated the aerial parts of M. hibiscifolia collected in Costa Rica. The lipophilic extract was separated using common column chromatography (CC) in addition to low-pressure chromatography (see Experimental Section).…”

“…The reinvestigation of the aerial parts of Montanoa hibiscifolia afforded four new eudesmanolides (1)(2)(3)(4), three of them with a rare endoperoxide structural element and the fourth with a rare carbonyl function. It also afforded three unusual montabibisciolides (5)(6)(7), two (5 and 7) of which are new natural compounds.…”

“…The lipophilic extract was separated using common column chromatography (CC) in addition to lowpressure chromatography (see Experimental Section). Bioguided fractionation using the agar plate diffusion assay with Bacillus subtilis as well as the electrophoretic mobility shift assay (EMSA) with the transcription factor NF-κB as molecular target led to the isolation of 15 Sls: four new eudesmanolides (1)(2)(3)(4), three (1-3) of which contain an endoperoxide structural element; two new (5 and 7) and one known (6) montahibisciolide; 2 seven germacrolides (8-10 and 12-15); and one melampolide (11). Of these the trans,trans germacrolides 8 and 9 are new natural compounds and 15 is new for the genus Montanoa, 5 whereas 10 and 12-14 as well as the melampolide 11 have already been isolated from M. hibiscifolia.…”

Constituents of the Pollen of Crocus sativus L. and Their Tyrosinase Inhibitory Activity.

“…2) 3,5,5-trimethyl-4-hydroxy-1-cyclohexanon-2-ene (9), 2) methylparaben (10), 23) protocatechuic acid methyl ester (11), 24) 4-hydroxybenzoic acid (12), 25) kaempferid (13), 26) 4-hydroxyphenethyl alcohol (14), 27) benzoic acid (15), 28) pyridin-3-yl-methanol (16), 29) nicotinamide (17), 31) adenosine (19), 32) isorhamnetin-3,4Ј-diglucoside (20), 33) isorhamnetin-3-O-robinobioside (21), 34) isorhamnetin-3-b-D-glucoside (22), 35) 5-methyluracil (23) 36) and uracil (24) 37) were also isolated and identified by comparison of their spectroscopic data (UV, IR and mass spectroscopy) with literature values.…”