Nitric oxide is synthesized by the NO synthase (NOS) and it plays a important role as physiological and useful substance in human body. However, the excess production of NO, caused by various stimuli such as cytokines, oxidants, and viruses, is involved in the various inflammatory diseases. In the c...
Nitric oxide is synthesized by the NO synthase (NOS) and it plays a important role as physiological and useful substance in human body. However, the excess production of NO, caused by various stimuli such as cytokines, oxidants, and viruses, is involved in the various inflammatory diseases. In the course of search for NO inhibitory plants, Dalbergia odorifera and Vitex rotundifolia were selected by first screening assay about 300 medicinal plants. In the bioactivity-guided fractionation and isolation of NO inhibitory compounds, two new isoflavanones, (3S)-3,7-dihydroxy-2′,4′-dimethoxyiso -flavanone (1) and (3R)-7-hydroxy-2′,4′,5′-trimethoxyisoflavanone, (13) along with twenty five known flavonoid, 2′,3′,7-trihydroxy-4′-methoxyisoflavanone, (2) violanone, (3) 3-O-methyl-violanone, (4) daidzein, (5) formononetin, (6) 2′-O-methylformononetin, (7) olibergin, (8) sativanone, (9) pinostrombin, (10) 2,4,3′,4′-tetrahydroxychalcone, (11) 2,4,4′-trihydroxychalcone, (12) 4′,6-dihydroxy-7-methoxyflavanone, (14) orobol, (15) 5,7,3,5′-tetrahydroxyflavanone, (16) melanettin, (17) 3′-hydroxymelanettin, (18) latifolin, (19) 3′-hydroxy-2,4,5-trimethoxydalbergiquinol, (20) 5-O-methyllatifolin, (21) 2-hydroxy-4,5- dimethoxydalbergiquinol, (22) α,3,4,2′,4′-pentahydroxydihydrochalcone, (23) α,4,2′,4′- tetrahydroxydihydrochalcone, (24) medicarpin, (26) and pinocembrin (27) and one known xanthone, 3-hydroxy-2-methoxyxanthone, (25) were isolated from the EtOAc-soluble fraction of the heartwood of D. odorifera. Among them, compounds 5, 6, 8, 10-12, 15, 17-22, 26, and 27 showed inhibitory effects on LPS-induced NO production in RAW 264.7 cells with IC50 values from 35.1 M to 99.8 M. These results suggested that flavonoids possessed a C-2,3 double bond or 5,7-dihydroxy in A ring were more active than compounds lacked these groups. Repeated and continued column chromatography of the MeOH extract from the fruits of V. rotundifolia led to the isolation of a new halimane-type and two new labdane-type diterpenes (rel 6S,7R,8S,9R)-7-hydroxy-6-methoxy-5(10),14-halimadien-13-ol, (35) (rel 5S,8R,9R,10S)-9-hydroxy-13(14)-labden-16,15-olide, (42) and (rel 3S,5S,8R,9R, 10S)-3-acetyloxy-9-hydroxy-13(14)-labden-16,15-olide, (44) two new diconiferyl alcohol lignans 9′-methoxydehydrodiconiferyl alcohol, (46) and 9′-dimethoxydehydrodiconiferyl alcohol, (47) and fourteen known diterpenes, vitexilactone, (28) 6β-acetoxy-9α-hydroxy-13(14)-labden-16,15-olide, (29) viteagnusin Ι, (30) vitetrifolin D, (31) vitetrifolin E, (32) vitetrifolin F, (33) vitetrifolin G, (34) 9,13-epoxy-16-norlabda-13E-en-15-al, (36) 13-epi-2-oxo-kolavelool, (37) isolophanthin A, (38) vitedoin B, (39) viteagnusin F, (40) viteagnusin G, (41) and 3β,9-dihydroxy-13(14)-labden-16,15-olide, (43) four known lignans, dihydrodehydrodiconiferyl alcohol, (45) ficusal, (48) lariciresinol, (49) and fiscusesquilignan, (50) and a known polymethoxyflavanone, casticin (51). Among them, compounds 28-31, 34-36, 40, 41, 45-51 showed potent inhibition of NO production in LPS-induced RAW 264.7 cells with IC50 values ranging 11.3 M to 49.1 M while aminoguanidine, a positive control, showed an IC50 value of 16.6 M. Accordingly, flavonoids, diterpenes, and lignans isolated from D. odorifera and V. rotundifolia are worthy of further investigation for their potential as anti-inflammatory agents.
Nitric oxide is synthesized by the NO synthase (NOS) and it plays a important role as physiological and useful substance in human body. However, the excess production of NO, caused by various stimuli such as cytokines, oxidants, and viruses, is involved in the various inflammatory diseases. In the course of search for NO inhibitory plants, Dalbergia odorifera and Vitex rotundifolia were selected by first screening assay about 300 medicinal plants. In the bioactivity-guided fractionation and isolation of NO inhibitory compounds, two new isoflavanones, (3S)-3,7-dihydroxy-2′,4′-dimethoxyiso -flavanone (1) and (3R)-7-hydroxy-2′,4′,5′-trimethoxyisoflavanone, (13) along with twenty five known flavonoid, 2′,3′,7-trihydroxy-4′-methoxyisoflavanone, (2) violanone, (3) 3-O-methyl-violanone, (4) daidzein, (5) formononetin, (6) 2′-O-methylformononetin, (7) olibergin, (8) sativanone, (9) pinostrombin, (10) 2,4,3′,4′-tetrahydroxychalcone, (11) 2,4,4′-trihydroxychalcone, (12) 4′,6-dihydroxy-7-methoxyflavanone, (14) orobol, (15) 5,7,3,5′-tetrahydroxyflavanone, (16) melanettin, (17) 3′-hydroxymelanettin, (18) latifolin, (19) 3′-hydroxy-2,4,5-trimethoxydalbergiquinol, (20) 5-O-methyllatifolin, (21) 2-hydroxy-4,5- dimethoxydalbergiquinol, (22) α,3,4,2′,4′-pentahydroxydihydrochalcone, (23) α,4,2′,4′- tetrahydroxydihydrochalcone, (24) medicarpin, (26) and pinocembrin (27) and one known xanthone, 3-hydroxy-2-methoxyxanthone, (25) were isolated from the EtOAc-soluble fraction of the heartwood of D. odorifera. Among them, compounds 5, 6, 8, 10-12, 15, 17-22, 26, and 27 showed inhibitory effects on LPS-induced NO production in RAW 264.7 cells with IC50 values from 35.1 M to 99.8 M. These results suggested that flavonoids possessed a C-2,3 double bond or 5,7-dihydroxy in A ring were more active than compounds lacked these groups. Repeated and continued column chromatography of the MeOH extract from the fruits of V. rotundifolia led to the isolation of a new halimane-type and two new labdane-type diterpenes (rel 6S,7R,8S,9R)-7-hydroxy-6-methoxy-5(10),14-halimadien-13-ol, (35) (rel 5S,8R,9R,10S)-9-hydroxy-13(14)-labden-16,15-olide, (42) and (rel 3S,5S,8R,9R, 10S)-3-acetyloxy-9-hydroxy-13(14)-labden-16,15-olide, (44) two new diconiferyl alcohol lignans 9′-methoxydehydrodiconiferyl alcohol, (46) and 9′-dimethoxydehydrodiconiferyl alcohol, (47) and fourteen known diterpenes, vitexilactone, (28) 6β-acetoxy-9α-hydroxy-13(14)-labden-16,15-olide, (29) viteagnusin Ι, (30) vitetrifolin D, (31) vitetrifolin E, (32) vitetrifolin F, (33) vitetrifolin G, (34) 9,13-epoxy-16-norlabda-13E-en-15-al, (36) 13-epi-2-oxo-kolavelool, (37) isolophanthin A, (38) vitedoin B, (39) viteagnusin F, (40) viteagnusin G, (41) and 3β,9-dihydroxy-13(14)-labden-16,15-olide, (43) four known lignans, dihydrodehydrodiconiferyl alcohol, (45) ficusal, (48) lariciresinol, (49) and fiscusesquilignan, (50) and a known polymethoxyflavanone, casticin (51). Among them, compounds 28-31, 34-36, 40, 41, 45-51 showed potent inhibition of NO production in LPS-induced RAW 264.7 cells with IC50 values ranging 11.3 M to 49.1 M while aminoguanidine, a positive control, showed an IC50 value of 16.6 M. Accordingly, flavonoids, diterpenes, and lignans isolated from D. odorifera and V. rotundifolia are worthy of further investigation for their potential as anti-inflammatory agents.
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