Inhibitory Activity of Synthesized Acetylated Procyanidin B₁ Analogs against HeLa S3 Cells Proliferation

Author： Okamoto Syuhei Ishihara Sayaka Okamoto Taisuke Doi Syoma Harui Kota Higashino Yusuke Kawasaki Takashi Nakajima Noriyuki Saito Akiko

Publisher： MDPI

E-ISSN： 1420-3049|19|2|1775-1785

ISSN： 1420-3049

Source： Molecules, Vol.19, Iss.2, 2014-02, pp. : 1775-1785

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Abstract

Proanthocyanidins, also known as condensed tannins and/or oligomeric flavonoids, occur in many edible plants and have various interesting biological activities. Previously, we reported a synthetic method for the preparation of various procyanidins in pure form and described their biological activities. Here, we describe the synthesis of procyanidin B₁ acetylated analogs and discuss their inhibition activities against HeLa S3 cell proliferation. Surprisingly, the lower-unit acetylated procyanidin B₁ strongly inhibited the proliferation of HeLa S3 cells. This molecule showed much stronger inhibitory activity than did epigallocatechin-3-O-gallate (EGCG), green tea polyphenol, and dimeric compounds that included EGCG as a unit. This result suggests that the phenolic hydroxyl groups of the upper-units in flavan-3-ols are important for their inhibitory activity against cancer cell proliferation and that a hydrophobic lower unit dimer enhances this activity.