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Molecules 2014, 19(2), 1775-1785; doi:10.3390/molecules19021775
Article

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

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Received: 19 November 2013; in revised form: 22 January 2014 / Accepted: 28 January 2014 / Published: 4 February 2014
(This article belongs to the Special Issue Structure-Activity Relationship of Flavonoids)
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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.
Keywords: condensed tannins; oligomeric flavonoid; synthesis; cancer cells proliferation; inhibitory activity condensed tannins; oligomeric flavonoid; synthesis; cancer cells proliferation; inhibitory activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Okamoto, S.; Ishihara, S.; Okamoto, T.; Doi, S.; Harui, K.; Higashino, Y.; Kawasaki, T.; Nakajima, N.; Saito, A. Inhibitory Activity of Synthesized Acetylated Procyanidin B1 Analogs against HeLa S3 Cells Proliferation. Molecules 2014, 19, 1775-1785.

AMA Style

Okamoto S, Ishihara S, Okamoto T, Doi S, Harui K, Higashino Y, Kawasaki T, Nakajima N, Saito A. Inhibitory Activity of Synthesized Acetylated Procyanidin B1 Analogs against HeLa S3 Cells Proliferation. Molecules. 2014; 19(2):1775-1785.

Chicago/Turabian Style

Okamoto, Syuhei; Ishihara, Sayaka; Okamoto, Taisuke; Doi, Syoma; Harui, Kota; Higashino, Yusuke; Kawasaki, Takashi; Nakajima, Noriyuki; Saito, Akiko. 2014. "Inhibitory Activity of Synthesized Acetylated Procyanidin B1 Analogs against HeLa S3 Cells Proliferation." Molecules 19, no. 2: 1775-1785.


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