Synthesis of okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity

Ryohei Kobayashi; Kengo Hanaya; Mitsuru Shoji; Shigeru Ohba; Takeshi Sugai

doi:10.1271/bbb.120966

Synthesis of okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity

Ryohei Kobayashi, Kengo Hanaya, Mitsuru Shoji, Shigeru Ohba, Takeshi Sugai

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity, was synthesized from ellagic acid. The regioselectivity, solubility, and high reactivity of the intermediates throughout the synthesis were obtained by the complementary use of triisopropylsilyl (TIPS) and methoxyethoxymethyl (MEM) protective groups on the aglycone skeleton.

Original language	English
Pages (from-to)	810-813
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	77
Issue number	4
DOIs	https://doi.org/10.1271/bbb.120966
Publication status	Published - 2013

Keywords

Ellagic acid
Glucoside
Okicamelliaside

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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title = "Synthesis of okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity",

abstract = "Okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity, was synthesized from ellagic acid. The regioselectivity, solubility, and high reactivity of the intermediates throughout the synthesis were obtained by the complementary use of triisopropylsilyl (TIPS) and methoxyethoxymethyl (MEM) protective groups on the aglycone skeleton.",

keywords = "Ellagic acid, Glucoside, Okicamelliaside",

author = "Ryohei Kobayashi and Kengo Hanaya and Mitsuru Shoji and Shigeru Ohba and Takeshi Sugai",

note = "Funding Information: We thank Professor Ken-ichi Onodera of Kochi University for valuable discussions. This work was supported by grant-aid for scientific research (no. 23580152) and the formation of a research center in cell signaling drug discovery for molecular targeting therapies: matching fund subsidy 2009–2013 was from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and is gratefully acknowledged with thanks.",

year = "2013",

doi = "10.1271/bbb.120966",

language = "English",

volume = "77",

pages = "810--813",

journal = "Bioscience, Biotechnology and Biochemistry",

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T1 - Synthesis of okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity

AU - Kobayashi, Ryohei

AU - Hanaya, Kengo

AU - Shoji, Mitsuru

AU - Ohba, Shigeru

AU - Sugai, Takeshi

N1 - Funding Information: We thank Professor Ken-ichi Onodera of Kochi University for valuable discussions. This work was supported by grant-aid for scientific research (no. 23580152) and the formation of a research center in cell signaling drug discovery for molecular targeting therapies: matching fund subsidy 2009–2013 was from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and is gratefully acknowledged with thanks.

PY - 2013

Y1 - 2013

N2 - Okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity, was synthesized from ellagic acid. The regioselectivity, solubility, and high reactivity of the intermediates throughout the synthesis were obtained by the complementary use of triisopropylsilyl (TIPS) and methoxyethoxymethyl (MEM) protective groups on the aglycone skeleton.

AB - Okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity, was synthesized from ellagic acid. The regioselectivity, solubility, and high reactivity of the intermediates throughout the synthesis were obtained by the complementary use of triisopropylsilyl (TIPS) and methoxyethoxymethyl (MEM) protective groups on the aglycone skeleton.

KW - Ellagic acid

KW - Glucoside

KW - Okicamelliaside

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SN - 0916-8451

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JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

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Synthesis of okicamelliaside, a glucoside of ellagic acid with potent anti-degranulation activity

Abstract

Keywords

ASJC Scopus subject areas

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