Abstract
From the EtOAc-soluble fraction of a MeOH extract of the leaves of Breynia officinalis, five new compounds (1–5) along with 11 known compounds (6–16) were isolated. The structures of the new compounds were elucidated by spectroscopic methods and compounds 1–3 were found to be acylated hydroquinone apiofuranosylglucopyranosides, while compound 4 was an acylated hydroquinone glucopyranoside. Compound 5 was shown to be butyl p-coumarate and this seems to be its first isolation from a natural source. The tyrosinase inhibitory activity of all of the isolated compounds was assayed, and the activity was significant in p-coumarate derivatives. The most active compound, compound 3, also inhibited melanogenesis in an in vivo whole animal model, zebrafish.
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Acknowledgement
The authors are grateful for access to the superconducting NMR instrument (Brucker Avance III 600) at the Analytical Center of Molecular Medicine of the Hiroshima University Faculty of Medicine, and HR-ESI mass spectra were performed with LTQ Orbitrap XL spectrometer at the Analysis Center of Life Science of the Graduate School of Biomedical Sciences, Hiroshima University. This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and the Japan Society for the Promotion of Science (Nos. 22590006, 23590130, 25860078, 15H04651, and 17K08336). Thanks are also due to the Research Foundation for Pharmaceutical Sciences and the Takeda Science Foundation for the financial support. One of the authors (S.S.) thanks the Research Foundation for Pharmaceutical Sciences and the Cosmetology Research Foundation for the financial support.
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Sasaki, A., Yamano, Y., Sugimoto, S. et al. Phenolic compounds from the leaves of Breynia officinalis and their tyrosinase and melanogenesis inhibitory activities. J Nat Med 72, 381–389 (2018). https://doi.org/10.1007/s11418-017-1148-8
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DOI: https://doi.org/10.1007/s11418-017-1148-8