Isolation and characterization of a novel oligomeric proanthocyanidin with significant anti-cancer activities from grape stems (Vitis vinifera)

Kawahara Sei-Ichi; Kazuya Toda; Kiriko Matsumoto; Chisato Ishihara; Shuhei Nonobe; Chisato Matsunaga; Yoshika K Gomi; Shogo Senga; Koichiro Kawaguchi; Ayaka Yamamoto; Jutalak Suwannachot; Reiko Noda; Shuhei Kobayashi; Yasunori Hamauzu; Hidefumi Makabe; Hiroshi Fujii

doi:10.1038/s41598-019-48603-5

Isolation and characterization of a novel oligomeric proanthocyanidin with significant anti-cancer activities from grape stems (Vitis vinifera)

Sci Rep. 2019 Aug 19;9(1):12046. doi: 10.1038/s41598-019-48603-5.

Authors

Kawahara Sei-Ichi^{1

2}, Kazuya Toda³, Kiriko Matsumoto⁴, Chisato Ishihara⁴, Shuhei Nonobe⁴, Chisato Matsunaga³, Yoshika K Gomi³, Shogo Senga¹, Koichiro Kawaguchi¹, Ayaka Yamamoto⁴, Jutalak Suwannachot⁵, Reiko Noda⁵, Shuhei Kobayashi³, Yasunori Hamauzu^{1

5}, Hidefumi Makabe^{6

7

8}, Hiroshi Fujii^{9

10

11}

Affiliations

¹ Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan.
² St. Cousair Co., Ltd., 1260 Imogawa, Kami-minochi, Iizuna, Nagano, 389-1201, Japan.
³ Department of Bioscience and Biotechnology, Faculty of Agriculture, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan.
⁴ Graduate School of Science and Technology, Department of Biomedical Engineering, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan.
⁵ Graduate School of Science and Technology, Department of Agriculture, Division of Food Science and Biotechnology, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan.
⁶ Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan. makabeh@shinshu-u.ac.jp.
⁷ Graduate School of Science and Technology, Department of Agriculture, Division of Food Science and Biotechnology, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan. makabeh@shinshu-u.ac.jp.
⁸ Department of Interdisciplinary Genome Sciences and Cell Metabolism, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Minami-minowa, Kami-ina, Nagano, 399-4598, Japan. makabeh@shinshu-u.ac.jp.
⁹ Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan. hfujii@shinshu-u.ac.jp.
¹⁰ Graduate School of Science and Technology, Department of Biomedical Engineering, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano, 399-4598, Japan. hfujii@shinshu-u.ac.jp.
¹¹ Department of Interdisciplinary Genome Sciences and Cell Metabolism, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Minami-minowa, Kami-ina, Nagano, 399-4598, Japan. hfujii@shinshu-u.ac.jp.

Abstract

Novel proanthocyanidin fractions from grape stem extracts were purified using Amberlite XAD-1180N, Sephadex-LH-20, Toyopearl HW40F and reverse phase high-performance liquid chromatography. Two key compounds were estimated as epigallocatechin-(epicatechin)₇ gallate using electron-spray ionization time-of-flight mass spectrometry. Epigallocatechin-(epicatechin)₇ gallate (compound 1) showed significant anti-cancer activity in PC-3 prostate cancer cells. In particular, compound 1 suppressed the gene expression of fatty acid-binding protein 5 (FABP5), which is involved in promoting cell proliferation and metastasis in prostate cancer cells.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry*
Antineoplastic Agents, Phytogenic / isolation & purification
Cell Cycle Checkpoints / drug effects
Cell Line, Tumor
Cell Proliferation / drug effects
Chromatography, High Pressure Liquid
Fatty Acid-Binding Proteins / genetics
Gene Expression Regulation, Neoplastic / drug effects
Humans
Magnetic Resonance Spectroscopy
Plant Extracts / chemistry*
Plant Extracts / isolation & purification
Plant Stems / chemistry*
Polymers*
Proanthocyanidins / chemistry*
Proanthocyanidins / isolation & purification
Vitis / chemistry*

Substances

Antineoplastic Agents, Phytogenic
FABP5 protein, human
Fatty Acid-Binding Proteins
Plant Extracts
Polymers
Proanthocyanidins
proanthocyanidin