Medicinal Flowers. XXVII. New Flavanone and Chalcone Glycosides, Arenariumosides I, II, III, and IV, and Tumor Necrosis Factor-.ALPHA. Inhibitors from Everlasting, Flowers of Helichrysum arenarium

Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium

“…11-13 (498 mg)]. Fraction 11-9 (590.0 mg) was further purified by HPLC [Cosmosil 5C 18 -MS-II, MeOH–H 2 O (30:70, v/v) and Wakopak Navi C30-5, MeOH–H 2 O (45:55, v/v)] to give arenariumoside VI ( 3 , 41.0 mg, 0.010 %) together with arenariumoside III (18.4 mg, 0.0046 %), 6-hydroxyluteolin 7- O - β -D-glucopyranoside ( 25 , 4.0 mg, 0.0010 %), kaempferol 3,4′-di- O - β -D-glucopyranoside ( 30 , 44.7 mg, 0.011 %), and quercetin 3,3′-di- O - β -D-glucopyranoside ( 34 , 6.0 mg, 0.0015 %), as reported previously [4]. Fraction 11-10 (255.0 mg) was purified by HPLC [Wakopak Navi C30-5, MeOH–H 2 O (45:55, v/v)] to give arenariumoside VIII ( 4 , 70.0 mg, 0.018 %).…”

“…11 (6.10 g), and Fr. 12 (17.10 g)], as reported previously [4–6]. Fraction 11 (5.0 g) was subjected to reversed-phase ODS CC [300 g, MeOH–H 2 O (10:90 → 60:40, v/v) → MeOH] to afford 13 fractions [Fr.…”

“…Several flavonoids, megastigmanes, α -pyrones, and phthalides have been isolated from the flowers [3–9], achenes [10], roots [11, 12], capitula, and leafy stems [13] of H. arenarium . In the course of our studies on bioactive constituents from the flowers of H. arenarium [4–6], we have reported that the methanol extract and several flavonoids showed inhibitory effects on tumor necrosis factor- α (TNF- α )-induced cytotoxicity in L929 cells [4]. We further evaluated the extract and its constituents and found that the methanol extract inhibited blood glucose elevation in sucrose-loaded mice.…”

Chemical Constituents from the Roots and Rhizomes of Asarum heterotropoides var. mandshuricum and the In Vitro Anti-Inflammatory Activity

“…They were 14 lignans: asarinin A ( 6 ) [35], (1 R , 2 S , 5 R , 6 R )-5′- O -methylpluviatilol ( 13 ) [26], (–)-asarinin ( 14 ) [3], (–)-sesamin ( 15 ) [3], xanthoxylol ( 16 ) [45], clemaphenol A ( 17 ) [46], epipinoresinol ( 18 ) [47], neo-olivil ( 19 ) [48], (–)-piperitol ( 20 ) [49], episesaminone ( 21 ) [50], (7′ R )-7′-hydroxylariciresinol ( 22 ) [51], tanegool ( 23 ) [35], (–)-tanegol ( 24 ) [52], morinols G ( 25 ) [53]; six flavanones: (2 S )-naringenin ( 26 ) [54], (2 S )-naringenin-5- O -β- d -glucopyranoside ( 27 ) [55], (2 S )-liquiritigenin-7- O -β- d -glucopyranoside ( 28 ) [56], (2 S )-naringenin-7- O -β- d -glucopyranoside ( 29 ) [57], (2 S )-naringenin-5, 7-di- O -β- d -glucopyranoside ( 30 ) [58], naringenin-5, 4′-di- O -β- d -glucopyranoside ( 31 ) [59]; four monoterpenes: 2-exo- O -β- d -glucosyl-5-hydroxy-borneol ( 32 ) [42], aisasarinol ( 33 ) [42], asiarinol A ( 34 ) [8], car-3-ene-2, 5-dione ( 35 ) [8]; four straight chain amide derivatives: N - trans -coumaroyltyramine ( 36 ) [60], asaramid ( 37 ) [42], pellitorine ( 38 ) [7], N -isobutyl-3,4-methylenedioxy cinnamide ( 39 ) [61]; seven benzene derivatives: 3-methoxyl-5-methylbenzene-1- O -β- d -glucopyranoside ( 12 ) [62],1-(3′,4′-dihydroxy) phenyl-6,7-dihydroxy-isochroman ( 40 ) [63], trans -ferulic acid ( 41 ) [64], 2-(3, 4-dihydroxy)-phenyl-ethyl- O -β- d -glucopyranoside ( 42 ) [65], vanillic acid 1- O -β- d -glucopyranoside ( 43 ) [66], 3-(3,4-methylenedioxyphenyl)-1,2-propanediol ( 44 ) [67], 2, 3-dihydro-2-methyl-6-hydroxybenzofuran-5-carboxylic acid ( 45 ) [68]; and two fatty glycerides: glyceryl- 1 -stearate ( 46 ) [69], 2, 3-dihydroxypropyl-16-hydroxyhexadecanoate ( 47 ) [70]. The 15 known compounds 17 , 19 , 22 – 25 , 28 , 31 , 36 , 40 , 42 , 43 , and 45 – 47 were isolated for the first time from the genus Asarum , and five known compounds 16 , 32 , 33 , 37 , and 39 were first reported from A. heterotropoides var.…”

Comparative profiles of Achyrocline alata (Kunth) DC. and A. satureioides (Lam.) DC., Asteraceae, applying HPLC-DAD-MS

“…The fractionation of the ethyl acetate fraction on silica gel column using CHCl 3 :MeOH gradient, furnished 4,2´,4´-trihydroxy-6´-methoxychalcone (10), besides other flavonoids already isolated previously (3-O-methylquercetin 9, quercetin 8, and gnaphalin 11). This chalcone was determined by 1D-and 2D-NMR spectrometry by a comparison of some models available in the literature (Morikawa et al, 2009, Puyvelde et al, 1989, Slimestad et al, 2008, and by UV and ESI-MS data. Spectral data of the other known flavonoids (UV, NMR) were also compared with those described in the literature (Agrawal et al, 1989).…”