Abstract
Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)3. Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3.
Keywords:
Antitumor; Condensation; Lewis acid; Polyphenol; Procyanidin gallate.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / pharmacology*
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Biflavonoids / chemical synthesis
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Biflavonoids / chemistry*
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Biflavonoids / pharmacology*
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Catechin / chemical synthesis
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Catechin / chemistry*
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Catechin / pharmacology*
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Cell Line, Tumor
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Gallic Acid / chemical synthesis
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Gallic Acid / chemistry
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Gallic Acid / pharmacology
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Humans
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Male
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Mesylates / chemistry*
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Organometallic Compounds / chemistry*
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Proanthocyanidins / chemical synthesis
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Proanthocyanidins / chemistry*
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Proanthocyanidins / pharmacology*
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Prostatic Neoplasms / drug therapy
Substances
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Antineoplastic Agents
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Biflavonoids
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Mesylates
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Organometallic Compounds
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Proanthocyanidins
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procyanidin B2
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procyanidin B3
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ytterbium(III) triflate
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Gallic Acid
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Catechin