Antioxidant and Cytotoxic Diarylheptanoids Isolated from Zingiber officinale Rhizomes

Abstract

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, tetrahydrocurcumin (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‐1‐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,5S)‐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 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) assay. Most of the isolated compounds 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 compounds 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 IC50 values of 6.4 and 7.8 µmol/L, respectively.

MS-Based Metabolite Profiling of Aboveground and Root Components of Zingiber mioga and Officinale

“…Diarylheptanoid (7-(3,4-dihydroxy-5-methoxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-heptanone or 1-(3,4-dihydroxy-5-methoxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-heptanone), tetrahydrocurcumin, gingerenone A, and galanganol C showed Pearson’s positive coefficient correlation value (0 < r < 1) correlations with antioxidant activity and TPC assay (Figure 4). The highest antioxidant activity was observed in the root part of Z. officinale due to the presence of metabolites such as tetrahydrocurcumin and diarylheptanoid which have antioxidant activity showing highly positive correlation [45,46]. Precursor (phenylalanine) relative contents were high in the aboveground parts of Zingiber species.…”

In vitro evaluation of cytotoxicity of n-hexane extract from Alnus sieboldiana male flowers on VERO and HEK293 cell lines

“…Multiple articles denote that diarylheptanoids from the genus Alnus, as well as from Zingiber officinale, Alpinia officinarum and Viscum cruciatum, are cytotoxic agents against many cancer cell lines. Similar to curcumin, which is a wellknown diarylheptanoid, they may prove to be useful not only in cancer chemoprevention but also in chemotherapy [18,20,21,22].…”

Synthesis of star‐shaped CuO nanoparticles supported on magnetic functionalized graphene: Catalytic and antibacterial activity

“…Among these solid supports, GO has strong hydrophilicity due to reactive oxygen functional groups (epoxide, hydroxyl, and carboxyl groups) on its edge and basal plans but has a tendency to agglomerate due to van der Waals interactions. [22][23][24][25] In continuation of our previous works, [11,26] to solve this problem and increase the number of active sites, GO has been functionalized and used as a support for the synthesis of CuO NPs. In addition, for easy separation of this catalyst from reaction mixture, it was magnetized with Fe 3 O 4 NPs.…”