Inhibitory Effects on NO Production and DPPH Radicals and NBT Superoxide Activities of Diarylheptanoid Isolated from Enzymatically Hydrolyzed Ehthanolic Extract of Alnus sibirica
- PMID: 31137531
- PMCID: PMC6572109
- DOI: 10.3390/molecules24101938
Inhibitory Effects on NO Production and DPPH Radicals and NBT Superoxide Activities of Diarylheptanoid Isolated from Enzymatically Hydrolyzed Ehthanolic Extract of Alnus sibirica
Abstract
Alnus sibirica (AS) is geographically distributed in Korea, Japan, Northeast China, and Russia. Various anti-oxidant, anti-inflammation, anti-atopic dermatitis and anti-cancer biological effects of AS have been reported. Enzymatic hydrolysis decomposes the sugar bond attached to glycoside into aglycone which, generally, has a superior biological activity, compared to glycoside. Enzymatic hydrolysis of the extract (EAS) from AS was processed and the isolated compounds were investigated-hirsutanonol (1), hirsutenone (2), rubranol (3), and muricarpon B (4). The structures of these compounds were elucidated, and the biological activities were assessed. The ability of EAS and the compounds (1-4) to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and Nitroblue tetrazolium (NBT) superoxide, and to inhibit NO production was evaluated in vitro. EAS showed more potent antioxidant and anti-inflammatory activity than AS. All investigated compounds showed excellent antioxidant and anti-inflammatory activities.
Keywords: Alnus sibirica; anti-inflammatory; antioxidant; enzymatic hydrolysis; hirsutanonol; oregonin.
Conflict of interest statement
The authors declare no conflict of interest.
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References
-
- Lee S. Korean Folk Medicine. Pub. Center of Seoul National University; Seoul, Korea: 1966.
-
- Asakawa Y., Genjida F., Hayashi S., Matsuura T. A New Ketol from Alunus firma Sieb. Et Zucc.(Betulaceae) Tetrahedron Lett. 1969;10:3235–3237. doi: 10.1016/S0040-4039(01)88396-9. - DOI
-
- Terazawa M., Okuyama H., Miyake M. Isolation of hirsutanonol and hirsutenone, two new diarylheptanoids from the green bark of Keyamahannoki, Alnus hirsuta Turcz. Jap. Wood Res Soc. J. 1973;19:45–46.
-
- Karchesy J.J., Laver M.L., Barofsky D.F., Barofsky E. Structure of oregonin, a natural diarylheptanoid xyloside. J. Chem. Soc. Chem. Commun. 1974;16:649. doi: 10.1039/c39740000649. - DOI
-
- Nomura M., Tokoroyama T., Kubota T. Biarylheptanoids and other constituents from wood of Alnus japonica. Phytochemistry. 1981;20:1097–1104. doi: 10.1016/0031-9422(81)83035-X. - DOI
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