Polyphenols in Ammania auriculata: Structures, antioxidative activity and cytotoxicity

Abstract

Chemical and biological investigations of the extract of Ammania auriculata (Lytheraceae) resulted in the identification of eight polyphenols (1 - 8) for the first time from this plant, including the gallotannin, 2,3,6-tri-O-galloyl-(?,?)-4C<inf>1</inf>-glucopyranose (8), for which 1D and 2D-NMR spectra were recorded and assigned for the first time. The structures of all isolates (1 - 8) were elucidated by conventional methods, spectroscopic analysis, including 1D and 2D NMR, and by HR-ESIMS as well. All of the isolated compounds were evaluated for their antioxidant activities, determined by the DPPH and ORAC methods and for their cytotoxicity against the keratinocyte cell line HaCaT using the neutral red assay (NRU) and cell cycle analysis. Compounds 1, 3, 4, 5, and 6 significantly inhibited reactive oxygen species production with ED<inf>50</inf> values between 3.22 and 9.79 ?g/ml. Compounds 1, 3, 4, and 5 showed cytotoxic activity against HaCaT cells with IC<inf>50</inf> values between 30.7 and 84.1 ?g/ml. The new galloyl glucose (8) was found not cytotoxic. Ellagitannins, 2,3-hexahydroxy-(?/?)-glucopyranose (1) and 1-O-galloyl 2,3-hexahydroxy-(?)-glucopyranose (5) possess remarkable antioxidative and comparably weak cytotoxic activity.