Antioxidant and cytotoxic activities of naphthalene derivatives from Diospyros kaki

4,8-Dihydroxy-5-methoxy-2-naphthaldehyde (Compound I) was isolated from blackened heartwood of Diospyros kaki and was methylated with diazomethane. Antioxidant and cytotoxic activities of Compound I and two methylated derivatives [4-hydroxy-5,8-dimethoxy-2-(2-oxopropyl)-naphthalene (D-1) and 2-glyci...

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Veröffentlicht in:Journal of wood science 2011-04, Vol.57 (2), p.161-165
Hauptverfasser: Matsushita, Yasuyuki, Jang, In-Cheol, Imai, Takanori, Fukushima, Kazuhiko, Lee, Jeung-Min, Park, Hae-Ryong, Lee, Seung-Cheol
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Sprache:eng
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Zusammenfassung:4,8-Dihydroxy-5-methoxy-2-naphthaldehyde (Compound I) was isolated from blackened heartwood of Diospyros kaki and was methylated with diazomethane. Antioxidant and cytotoxic activities of Compound I and two methylated derivatives [4-hydroxy-5,8-dimethoxy-2-(2-oxopropyl)-naphthalene (D-1) and 2-glycidyl-4-hydroxy-5,8-dimethoxy naphthalene (D-2)] were evaluated. Compound I showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and reducing power than D-1 and D-2. However, D-1 and D-2 exhibited slightly stronger 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) + (ABTS + ) radical scavenging activity than Compound I. Compound I also exhibited stronger cytotoxic activity than D-1 and D-2 against the growth of HT-29 colon cancer cells. The results supported the hypothesis that methylation of naphthalene derivatives slightly increased ABTS + radical scavenging activity, but significantly decreased DPPH radical scavenging activity, reducing power, and cytotoxic activity.
ISSN:1435-0211
1611-4663
DOI:10.1007/s10086-010-1147-9