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Biological Activities of Triterpenoids and Phenolic Compounds from <i>Myrica</i> <i>cerifera</i> Bark

Jie ZhangDepartment of Natural Medicine Chemistry China Pharmaceutical University 24 Tongjiaxiang Nanjing 210009 P. R. ChinaSatoshi YamadaCollege of Science and Technology Nihon University 1‐8‐14 Kanda Surugadai Chiyoda‐ku, Tokyo 101‐8308 JapanEri OgiharaCollege of Science and Technology Nihon University 1‐8‐14 Kanda Surugadai Chiyoda‐ku, Tokyo 101‐8308 JapanMasahiro KuritaCollege of Science and Technology Nihon University 1‐8‐14 Kanda Surugadai Chiyoda‐ku, Tokyo 101‐8308 JapanNorihiro BannoIchimaru Pharcos Company Ltd. 318‐1 Asagi Motosu‐shi, Gifu 501‐0475 JapanWei QuDepartment of Natural Medicine Chemistry China Pharmaceutical University 24 Tongjiaxiang Nanjing 210009 P. R. ChinaFeng FengDepartment of Natural Medicine Chemistry China Pharmaceutical University 24 Tongjiaxiang Nanjing 210009 P. R. ChinaToshihiro AkihisaAkihisa Medical Clinic 1086‐3 Kamo Sanda‐shi, Hyogo 669‐1311 Japan
2016en
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Seven triterpenoids, 1 – 7 , two diarylheptanoids, 8 and 9 , four phenolic compounds, 10 – 13 , and three other compounds, 14 – 16 , were isolated from the hexane and Me OH extracts of the bark of Myrica cerifera L. (Myricaceae). Among these compounds, betulin ( 1 ), ursolic acid ( 3 ), and myricanol ( 8 ) exhibited cytotoxic activities against HL 60 (leukemia), A549 (lung), and SK ‐ BR ‐3 (breast) human cancer cell lines ( IC 50 3.1 – 24.2 μ m ). Compound 8 induced apoptotic cell death in HL 60 cells ( IC 50 5.3 μ m ) upon evaluation of the apoptosis‐inducing activity by flow cytometric analysis and by Hoechst 33342 staining method. Western blot analysis on HL 60 cells revealed that 8 activated caspases‐3, ‐8, and ‐9 suggesting that 8 induced apoptosis via both mitochondrial and death receptor pathways in HL 60. Upon evaluation of the melanogenesis‐inhibitory activity in B16 melanoma cells induced with α ‐melanocyte‐stimulating hormone ( α ‐ MSH ), erythrodiol ( 7 ), 4‐hydroxy‐2‐methoxyphenyl β ‐ d ‐glucopyranoside ( 13 ), and butyl quinate ( 15 ) exhibited inhibitory effects (65.4 – 86.0% melanin content) with no, or almost no, toxicity to the cells (85.9 – 107.4% cell viability) at 100 μ m concentration. In addition, 8 , myricanone ( 9 ), myricitrin ( 10 ), protocatechuic acid ( 11 ), and gallic acid ( 12 ) revealed potent DPPH radical‐scavenging activities ( IC 50 6.9 – 20.5 μ m ).

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