Inhibitory activity of synthesized acetylated Procyanidin B1 analogs against HeLa S3 cells proliferation.
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.
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. me12a003@oecu.jp.
Syuhei
S
Okamoto
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. me12a002@oecu.jp.
Sayaka
S
Ishihara
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. me12a004@oecu.jp.
Taisuke
T
Okamoto
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. me12a008@oecu.jp.
Syoma
S
Doi
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. me13a012@oecu.jp.
Kota
K
Harui
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. me13a013@oecu.jp.
Yusuke
Y
Higashino
Department of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan. kawa0227@fc.ritsumei.ac.jp.
Takashi
T
Kawasaki
Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan. nori@pu-toyama.ac.jp.
Noriyuki
N
Nakajima
Graduate School of Engineering, Osaka Electro-communication University (OECU), 18-8 Hatsu-cho, Neyagawa-shi, Osaka 572-8530, Japan. a-saito@isc.osakac.ac.jp.
Akiko
A
Saito
D000107:Acetylation; D044946:Biflavonoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002392:Catechin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects*; D006367:HeLa Cells; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy* / Q000473:pathology; D011108:Polymers / Q000737:chemistry; D044945:Proanthocyanidins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013662:Tea / Q000737:chemistry
D044946:Biflavonoids; D011108:Polymers; D044945:Proanthocyanidins; D013662:Tea; C479579:procyanidin B1; D002392:Catechin; C045651:epigallocatechin gallate