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Antioxidant and Cytotoxic Diarylheptanoids Isolated from Zingiber officinale Rhizomes

Antioxidant and Cytotoxic Diarylheptanoids Isolated from Zingiber officinale Rhizomes
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摘要 One new diarylheptanoid, namely (4E,6E)-7-(3,4-dihydroxy-5-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)- hepta-4,6-dien-3-one (1), was isolated from the rhizomes of Zingiber officinale, along with ten known ones, tetra- hydrocurcumin (2), curcumin (3), 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (4), gingerenone A (5), 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one (6), (E)-1,7-bis(4-hydroxy- 3-methoxyphenyl)hept-1-ene-3,5-dione (7), (E)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hept-l-ene- 3,5-dione (8), shogasulfonic acid A (9), 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxy-3- methoxyphenyl)heptane (10), and (3S, SS)-3,5-diacetoxy-1,7-bis(3,4-dihydroxyphenyl)heptane (11). Their structures were elucidated on the basis of spectral evidence and comparisons with literature data. The free radical scavenging activity of 1--11 was evaluated by the 1,l-diphenyl-2-picrylhydrazyl (DPPH) assay. Most of the isolated com- pounds were found to be better antioxidants than the positive control ascorbic acid. These compounds were also evaluated for their cytotoxicity against HeLa and MNK-45 cells using the MTT assay. Our results suggest that com- pounds 3 and 5-8 inhibited HeLa cells, and 3, 5, 7 and 8 inhibited MNK-45 cells. It was found that compound 5 was markedly cytotoxic against HeLa and MNK-45 cell lines with ICs0 values of 6.4 and 7.8 μmol/L, respectively. One new diarylheptanoid, namely (4E,6E)-7-(3,4-dihydroxy-5-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)- hepta-4,6-dien-3-one (1), was isolated from the rhizomes of Zingiber officinale, along with ten known ones, tetra- hydrocurcumin (2), curcumin (3), 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (4), gingerenone A (5), 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one (6), (E)-1,7-bis(4-hydroxy- 3-methoxyphenyl)hept-1-ene-3,5-dione (7), (E)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hept-l-ene- 3,5-dione (8), shogasulfonic acid A (9), 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxy-3- methoxyphenyl)heptane (10), and (3S, SS)-3,5-diacetoxy-1,7-bis(3,4-dihydroxyphenyl)heptane (11). Their structures were elucidated on the basis of spectral evidence and comparisons with literature data. The free radical scavenging activity of 1--11 was evaluated by the 1,l-diphenyl-2-picrylhydrazyl (DPPH) assay. Most of the isolated com- pounds were found to be better antioxidants than the positive control ascorbic acid. These compounds were also evaluated for their cytotoxicity against HeLa and MNK-45 cells using the MTT assay. Our results suggest that com- pounds 3 and 5-8 inhibited HeLa cells, and 3, 5, 7 and 8 inhibited MNK-45 cells. It was found that compound 5 was markedly cytotoxic against HeLa and MNK-45 cell lines with ICs0 values of 6.4 and 7.8 μmol/L, respectively.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2012年第6期1351-1355,共5页 中国化学(英文版)
关键词 Zingiber officinale DIARYLHEPTANOID NMR spectroscopy structure elucidation antioxidant and cyto-toxic activities Zingiber officinale, diarylheptanoid, NMR spectroscopy, structure elucidation, antioxidant and cyto-toxic activities
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