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Antioxidative and Melanogenesis‐Inhibitory Activities of Caffeoylquinic Acids and Other Compounds from Moxa
Author(s) -
Akihisa Toshihiro,
Kawashima Kohta,
Orido Masashi,
Akazawa Hiroyuki,
Matsumoto Masahiro,
Yamamoto Ayako,
Ogihara Eri,
Fukatsu Makoto,
Tokuda Harukuni,
Fuji Jizaemon
Publication year - 2013
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201200357
Subject(s) - chemistry , tyrosinase , dpph , chlorogenic acid , linoleic acid , lupeol , biochemistry , antioxidant , food science , enzyme , fatty acid
Abstract The MeOH extract of moxa, the processed leaves of Artemisia princeps Pamp . (Asteraceae), exhibited potent 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical‐scavenging activity and melanogenesis‐inhibitory activity in α ‐melanocyte‐stimulating hormone ( α ‐MSH)‐stimulated B16 melanoma cells. Eight caffeoylquinic acids, 1 and 6 – 12 , five flavonoids, 13 – 17 , two benzoic acid derivatives, 18 and 19 , three coumarin derivatives, 20 – 22 , four steroids, 23 – 26 , and six triterpenoids, 27 – 32 , were isolated from the MeOH extract. Upon evaluation of compounds 1, 6 – 23 , and four semisynthetic caffeoylquinic acid esters, 2 – 5 , for their DPPH radical‐scavenging activity, 15 compounds, 1 – 13, 17 , and 19 , showed potent activities ( IC 50 3.1–16.8 μ M ). 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, 1 – 8, 10, 12, 13, 15 – 18, 20 – 25 , and 27 – 32 , were evaluated for their inhibitory activity against melanogenesis in α ‐MSH‐stimulated B16 melanoma cells, five caffeoylquinic acids, i.e. , chlorogenic acid ( 1 ), ethyl chlorogenate ( 3 ), propyl chlorogenate ( 4 ), isopropyl chlorogenate ( 5 ), and butyl chlorogenate ( 6 ), along with homoorientin ( 17 ) and vanillic acid ( 18 ), exhibited inhibitory activities with 33–62% reduction of melanin content at 100 μ M concentration with no or almost no toxicity to the cells (89–114% of cell viability at 100 μ M ). Western blot analysis showed that compound 6 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 α ‐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, 13, 15, 16 , and 30 , exhibited cytotoxicities against HL60 human leukemia cell line ( IC 50 7.0–11.1 μ M ), and nine compounds, 14 – 16, 23, 26 – 28, 31 , and 32 , showed inhibitory effects ( IC 50 272–382 mol ratio/32 pmol 12‐ O ‐tetradecanoylphohrbol‐13‐acetate (TPA)) against EpsteinBarr virus early antigen (EBV‐EA) activation induced by TPA in Raji cells.