Antioxidative and Melanogenesis‐Inhibitory Activities of Caffeoylquinic Acids and Other Compounds from Moxa. Issue 3 (13th March 2013)

• Record Type: Journal Article
• Authors: Akihisa, Toshihiro; Kawashima, Kohta; Orido, Masashi; Akazawa, Hiroyuki; Matsumoto, Masahiro; Yamamoto, Ayako; Ogihara, Eri; Fukatsu, Makoto; Tokuda, Harukuni; Fuji, Jizaemon
• Is Part Of: Chemistry & biodiversity. Volume 10:Issue 3(2013:Mar.)
• Page Start: 313
• Page End: 327
• Publication Date: 2013-03-13
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201200357
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The MeOH extract of moxa, the processed leaves of <italic>Artemisia princeps</italic><sc>Pamp</sc>. (Asteraceae), exhibited potent 1, 1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical‐scavenging activity and melanogenesis‐inhibitory activity in <italic>α</italic>‐melanocyte‐stimulating hormone (<italic>α</italic>‐MSH)‐stimulated B16 melanoma cells. Eight caffeoylquinic acids, <bold>1</bold> and <bold>6</bold>–<bold>12</bold>, five flavonoids, <bold>13</bold>–<bold>17</bold>, two benzoic acid derivatives, <bold>18</bold> and <bold>19</bold>, three coumarin derivatives, <bold>20</bold>–<bold>22</bold>, four steroids, <bold>23</bold>–<bold>26</bold>, and six triterpenoids, <bold>27</bold>–<bold>32</bold>, were isolated from the MeOH extract. Upon evaluation of compounds <bold>1, 6</bold>–<bold>23</bold>, and four semisynthetic caffeoylquinic acid esters, <bold>2</bold>–<bold>5</bold>, for their DPPH radical‐scavenging activity, 15 compounds, <bold>1</bold>–<bold>13, 17</bold>, and <bold>19</bold>, showed potent activities (<italic>IC</italic><sub>50</sub> 3.1–16.8 μ<sc>M</sc>). The 15 compounds exhibited, moreover, potent inhibitory activities (51.1–92.5% inhibition) against peroxidation of linoleic acid emulsion at 10 μg/ml concentration. In addition, when 27 compounds, <bold>1</bold>–<bold>8, 10, 12, 13, 15</bold>–<bold>18, 20</bold>–<bold>25</bold>, and <bold>27</bold>–<bold>32</bold>, were evaluated for their inhibitory activity against melanogenesis in <italic>α</italic>‐MSH‐stimulated B16 melanoma cells, five caffeoylquinic acids, <italic>i.e.</italic>, chlorogenic acid (<bold>1</bold>), ethyl chlorogenate (<bold>3</bold>), propyl chlorogenate (<bold>4</bold>), isopropyl chlorogenate (<bold>5</bold>), and butyl chlorogenate (<bold>6</bold>), along with homoorientin (<bold>17</bold>) and vanillic acid (<bold>18</bold>), exhibited inhibitory activities with 33–62% reduction of melanin content at 100 μ<sc>M</sc> concentration with no or almost no toxicity to the cells (89–114% of cell viability at 100 μ<sc>M</sc>). <italic>Western</italic> blot analysis showed that compound <bold>6</bold> reduced the protein levels of microphtalmia‐associated transcription factor (MITF), tyrosinase, tyrosine‐related protein 1 (TRP‐1), and TRP‐2 mostly in a concentration‐dependent manner, suggesting that this compound inhibits melanogenesis on <italic>α</italic>‐MSH‐stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of tyrosinase, TRP‐1, and TRP‐2. Furthermore, four compounds, <bold>13, 15, 16</bold>, and <bold>30</bold>, exhibited cytotoxicities against HL60 human leukemia cell line (<italic>IC</italic><sub>50</sub> 7.0–11.1 μ<sc>M</sc>), and nine compounds, <bold>14</bold>–<bold>16, 23, 26</bold>–<bold>28, 31</bold>, and <bold>32</bold>, showed inhibitory effects (<italic>IC</italic><sub>50</sub> 272–382 mol ratio/32 pmol 12‐<italic>O</italic>‐tetradecanoylphohrbol‐13‐acetate (TPA)) against <italic>EpsteinBarr</italic> virus early antigen (EBV‐EA) activation induced by TPA in <italic>Raji</italic> cells.</p> </abstract>