- Chemical synthesis, redox transformation, and identification of sonnerphenolic C, an antioxidant in Acer nikoense
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Sonnerphenolic C (3), which was predicted in a redox product of epirhododendrin (1) isolated from Acer nikoense, was synthesized for the first time via the epimeric separation of benzylidene acetal intermediates as a key step. From a similar synthetic route, 1 was obtained concisely. As a result of their antioxidative evaluation, only 3 revealed potent activity. The redox transformation of 1 into 3 was achieved in the presence of tyrosinase and vitamin C. Moreover, 3 was identified in the decoction of A. nikoense by HPLC analysis with the effective use of synthesized 3. Thus, a novel naturally occurring antioxidant 3 was developed through the sequential flow including redox prediction, chemical synthesis, evaluation of the activity, and identification as the natural product.
- Iwadate, Takehiro,Nihei, Ken-ichi
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- Synthesis of rhododendrin and epi-rhododendrin,
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The first synthesis of rhododendrin 1 and epi-rhododendrin 2 was achieved by starting from ethyl (S)-3-hydroxybutanoate 4, p-bromoanisole and D-glucose.Rhododendrin 1 is known as the hepatoprotective constituent of Taxus baccata L. Keywords: betuligenol / betuloside / epi-rhododendrin / rhododendrin / rhododendrol
- Mori, Kenji,Qian, Zhao-Hui
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p. 382 - 387
(2007/10/02)
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