(+)-neo-olivil from roots of Urtica dioica

Lignans from the flowers of Osmanthus fragrans var. aurantiacus and their inhibition effect on NO production

“…The chemical structures of the compounds were determined by analysis of the 1 Hand 13 C-NMR spectra including DEPT, HSQC, HMBC, COSY, and NOESY experiments. Six known compounds 1-6 were identified to be (+)-phillygenin (1) (Rahman et al, 1990;Miyauchi and Ozawa, 1998), phillyrin (2) (Boyer et al, 2005;Li et al, 2008;Sakamoto et al, 2008), (−)-phillygenin (3) (Messiano et al, 2008), (−)-epipinoresinol-β-D-glucoside (4) (Schottner et al, 1997), taxiresinol (5) (Chattopadhyay et al, 2003;Erdemoglu et al, 2004;Veselova et al, 2007), and (−)-olivil (6) (Yeo et al, 2004) based on physical and spectroscopic evidences, and confirmed by comparing with published data. Compound 7 was revealed to be a new compound that had never been previously reported in nature.…”

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.…”

Antibacterial Activity of a Virgatusin-Related Compound

“…The relationship between antibacterial activity of tetra-substituted tetrahydrofuran lignans (1)(2)(3)(4) and their absolute configurations was tested. Only compound 4 among two virgatusins and two related compounds exhibited growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis, Staphylococcus aureus and Listeria denitrificans.…”

“…Some similar compounds have been isolated from plants. [3][4][5][6] Though the reversal of multidrug resistance by a similar tetrasubstituted tetrahydrofuran lignan has been reported, 7) the relationship between activity and stereochemistry was unknown. It is known that lignans have many kinds of biological activity 8,9) and some lignans had antibacterial activity, [8][9][10][11] however, biological research was performed by using compounds isolated from plants in many cases.…”