Melanogenesis‐Inhibitory Saccharide Fatty Acid Esters and Other Constituents of the Fruits of Morinda citrifolia (Noni)

Chemistry & Biodiversity
2012.0

Abstract

<jats:title>Abstract</jats:title><jats:p>Five new saccharide fatty acid esters, named nonioside P (<jats:bold>3</jats:bold>), nonioside Q (<jats:bold>4</jats:bold>), nonioside R (<jats:bold>8</jats:bold>), nonioside S (<jats:bold>10</jats:bold>), and nonioside T (<jats:bold>14</jats:bold>), and one new succinic acid ester, butyl 2‐hydroxysuccinate (=4‐butoxy‐3‐hydroxy‐4‐oxobutanoic acid) (<jats:bold>31</jats:bold>), were isolated, along with 26 known compounds, including eight saccharide fatty acid esters, <jats:bold>1, 2, 5, 6, 7, 9, 12</jats:bold>, and <jats:bold>13</jats:bold>, three hemiterpene glycosides, <jats:bold>15, 17</jats:bold>, and <jats:bold>18</jats:bold>, six iridoid glycosides, <jats:bold>21</jats:bold>–<jats:bold>25</jats:bold>, and <jats:bold>27</jats:bold>, and nine other compounds, <jats:bold>20, 28, 29</jats:bold>, and <jats:bold>32</jats:bold>–<jats:bold>37</jats:bold>, from a MeOH extract of the fruit of <jats:italic>Morinda citrifolia</jats:italic> (<jats:italic>noni</jats:italic>). Upon evaluation of these and five other glycosidic compounds, <jats:bold>11, 16, 19, 26</jats:bold>, and <jats:bold>30</jats:bold>, from <jats:italic>M. citrifolia</jats:italic> fruit extract for their inhibitory activities against melanogenesis in B16 melanoma cells induced with <jats:italic>α</jats:italic>‐melanocyte‐stimulating hormone (<jats:italic>α</jats:italic>‐MSH), most of the saccharide fatty acid esters, hemiterpene glycosides, and iridoid glycosides showed inhibitory effects with no or almost no toxicity to the cells. These compounds were further evaluated with respect to their cytotoxic activities against two human cancer cell lines (HL‐60 and AZ521) and their inhibitory effects on <jats:italic>EpsteinBarr</jats:italic> virus early antigen (EBV‐EA) activation induced with 12‐<jats:italic>O</jats:italic>‐tetradecanoylphorbol‐13‐acetate (TPA) in <jats:italic>Raji</jats:italic> cells.

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