Elucidation of the interaction between flavan-3-ols and bovine serum albumin and its effect on their in-vitro cytotoxicity

Yasuyuki Fujii, Yoshitomo Suhara, Yusuke Sukikara, Tomohiro Teshima, Yoshihisa Hirota, Kenjiro Yoshimura, Naomi Osakabe

Research output: Contribution to journalArticle

Abstract

Flavan-3-ols (FLs), specifically catechin and its oligomer B-type procyanidins, are suggested to potently bind to bovine serum albumin (BSA). We examined the interaction between BSA and FLs by fluorescence quenching and found the following order of binding activities to BSA: cinnamtannin A2 (A2; tetramer) > procyanidin C1 (C1; trimer) ≈ procyanidin B2 (B2, dimer) > (-)epicatechin (EC, monomer). Docking simulations between BSA and each compound at the binding site showed that the calculated binding energies were consistent with the results of our experimental assay. FLs exerted cytotoxicity at 1000 μg/mL in F11 cell culture with fetal bovine serum containing BSA. In culture containing serum-free medium, FLs exhibited significant cell proliferation at 10-4 μg/mL and cytotoxicity was observed at concentrations greater than 10 μg/mL. Results of this study suggest that interactions between polyphenols and BSA should be taken into account when evaluating procyanidin in an in vitro cell culture system.

Original languageEnglish
Article number3667
JournalMolecules
Volume24
Issue number20
DOIs
Publication statusPublished - 2019 Oct 11

Fingerprint

Cytotoxicity
Bovine Serum Albumin
albumins
serums
Cell culture
Catechin
interactions
Proanthocyanidins
Serum-Free Culture Media
Cell proliferation
Polyphenols
Binding energy
Oligomers
Dimers
Quenching
Assays
trimers
Monomers
Fluorescence
Binding Sites

Keywords

  • B-type procyanidin
  • Bovine serum albumin
  • Cytotoxicity
  • Docking simulation
  • Flavan-3-ols

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Elucidation of the interaction between flavan-3-ols and bovine serum albumin and its effect on their in-vitro cytotoxicity. / Fujii, Yasuyuki; Suhara, Yoshitomo; Sukikara, Yusuke; Teshima, Tomohiro; Hirota, Yoshihisa; Yoshimura, Kenjiro; Osakabe, Naomi.

In: Molecules, Vol. 24, No. 20, 3667, 11.10.2019.

Research output: Contribution to journalArticle

@article{d285adf072d84f6cbcad2e18f23450f1,
title = "Elucidation of the interaction between flavan-3-ols and bovine serum albumin and its effect on their in-vitro cytotoxicity",
abstract = "Flavan-3-ols (FLs), specifically catechin and its oligomer B-type procyanidins, are suggested to potently bind to bovine serum albumin (BSA). We examined the interaction between BSA and FLs by fluorescence quenching and found the following order of binding activities to BSA: cinnamtannin A2 (A2; tetramer) > procyanidin C1 (C1; trimer) ≈ procyanidin B2 (B2, dimer) > (-)epicatechin (EC, monomer). Docking simulations between BSA and each compound at the binding site showed that the calculated binding energies were consistent with the results of our experimental assay. FLs exerted cytotoxicity at 1000 μg/mL in F11 cell culture with fetal bovine serum containing BSA. In culture containing serum-free medium, FLs exhibited significant cell proliferation at 10-4 μg/mL and cytotoxicity was observed at concentrations greater than 10 μg/mL. Results of this study suggest that interactions between polyphenols and BSA should be taken into account when evaluating procyanidin in an in vitro cell culture system.",
keywords = "B-type procyanidin, Bovine serum albumin, Cytotoxicity, Docking simulation, Flavan-3-ols",
author = "Yasuyuki Fujii and Yoshitomo Suhara and Yusuke Sukikara and Tomohiro Teshima and Yoshihisa Hirota and Kenjiro Yoshimura and Naomi Osakabe",
year = "2019",
month = "10",
day = "11",
doi = "10.3390/molecules24203667",
language = "English",
volume = "24",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "20",

}

TY - JOUR

T1 - Elucidation of the interaction between flavan-3-ols and bovine serum albumin and its effect on their in-vitro cytotoxicity

AU - Fujii, Yasuyuki

AU - Suhara, Yoshitomo

AU - Sukikara, Yusuke

AU - Teshima, Tomohiro

AU - Hirota, Yoshihisa

AU - Yoshimura, Kenjiro

AU - Osakabe, Naomi

PY - 2019/10/11

Y1 - 2019/10/11

N2 - Flavan-3-ols (FLs), specifically catechin and its oligomer B-type procyanidins, are suggested to potently bind to bovine serum albumin (BSA). We examined the interaction between BSA and FLs by fluorescence quenching and found the following order of binding activities to BSA: cinnamtannin A2 (A2; tetramer) > procyanidin C1 (C1; trimer) ≈ procyanidin B2 (B2, dimer) > (-)epicatechin (EC, monomer). Docking simulations between BSA and each compound at the binding site showed that the calculated binding energies were consistent with the results of our experimental assay. FLs exerted cytotoxicity at 1000 μg/mL in F11 cell culture with fetal bovine serum containing BSA. In culture containing serum-free medium, FLs exhibited significant cell proliferation at 10-4 μg/mL and cytotoxicity was observed at concentrations greater than 10 μg/mL. Results of this study suggest that interactions between polyphenols and BSA should be taken into account when evaluating procyanidin in an in vitro cell culture system.

AB - Flavan-3-ols (FLs), specifically catechin and its oligomer B-type procyanidins, are suggested to potently bind to bovine serum albumin (BSA). We examined the interaction between BSA and FLs by fluorescence quenching and found the following order of binding activities to BSA: cinnamtannin A2 (A2; tetramer) > procyanidin C1 (C1; trimer) ≈ procyanidin B2 (B2, dimer) > (-)epicatechin (EC, monomer). Docking simulations between BSA and each compound at the binding site showed that the calculated binding energies were consistent with the results of our experimental assay. FLs exerted cytotoxicity at 1000 μg/mL in F11 cell culture with fetal bovine serum containing BSA. In culture containing serum-free medium, FLs exhibited significant cell proliferation at 10-4 μg/mL and cytotoxicity was observed at concentrations greater than 10 μg/mL. Results of this study suggest that interactions between polyphenols and BSA should be taken into account when evaluating procyanidin in an in vitro cell culture system.

KW - B-type procyanidin

KW - Bovine serum albumin

KW - Cytotoxicity

KW - Docking simulation

KW - Flavan-3-ols

UR - http://www.scopus.com/inward/record.url?scp=85073425095&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85073425095&partnerID=8YFLogxK

U2 - 10.3390/molecules24203667

DO - 10.3390/molecules24203667

M3 - Article

C2 - 31614668

AN - SCOPUS:85073425095

VL - 24

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 20

M1 - 3667

ER -