Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by

Apr 5, 2019 - Around 380,000 years after the big bang, the plasma that was our universe cooled enough for nuclei and... BUSINESS CONCENTRATES ...
0 downloads 0 Views 781KB Size
Subscriber access provided by University of Victoria Libraries

Bioactive Constituents, Metabolites, and Functions

Sesamin catechol glucuronides exert anti-inflammatory effects by suppressing IFN-# and iNOS expression through the deconjugation in macrophage-like J774.1 cells Naomi Abe-Kanoh, Yumi Lee, Daisuke Takemoto, Yoshiko Ono, Hiroshi Shibata, Kohta Ohnishi, and Yoshichika Kawai J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.8b07227 • Publication Date (Web): 05 Apr 2019 Downloaded from http://pubs.acs.org on April 7, 2019

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 39

Journal of Agricultural and Food Chemistry

Sesamin catechol glucuronides exert anti-inflammatory effects by suppressing

and

iNOS expression through the deconjugation in macrophage-like J774.1 cells Naomi Abe-Kanoh*,†,‡, Yumi Lee§, Daisuke Takemoto , Yoshiko Ono*, , Hiroshi Shibata , Kohta Ohnishi†, , Yoshichika Kawai†



Department of Food Science, Institute of Biomedical Sciences, Tokushima University Graduate

School, Tokushima 770-8503, Japan ‡ Department

of Public Health and Applied Nutrition, Institute of Biomedical Sciences,

Tokushima University Graduate School, Tokushima 770-8503, Japan §

Department of Food Science, School of Medical Nutrition, Tokushima University, Tokushima

770-8503, Japan Institute for Health Care Science, Suntory Wellness, Ltd., 8-1-1 Seikadai, Seika-cho, Sorakugun, Kyoto 619-0284, Japan Department of Clinical Nutrition and Food Management, Institute of Biomedical Sciences, Tokushima University Graduate School, Tokushima 770-8503, Japan Corresponding author: *(Y O) E-mail: [email protected], Tel.: +81-774-66-1110. Fax: +81-774-98-6262. *(N A-K) E-mail: [email protected], Tel./Fax: +81-88-633-7450 1 ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 2 of 39

1

ABSTRACT

2

Sesamin, a representative sesame lignan, has health promoting activities. Sesamin is converted into

3

catechol derivatives and further into their glucuronides or sulfates in vivo, whereas the biological

4

activities of sesamin metabolites remain unclear. We examined the inhibitory effects of sesamin

5

metabolites on the lipopolysaccharide (LPS)-induced NO production in mouse macrophage-like

6

J774.1 cells and found that a mono-catechol derivative SC1, =-F -GF /F /GF>-3,4-dihydroxy-3’,4’-

7

methylenedioxy-7,9’:7’,9-diepoxylignane, has a much higher activity than sesamin and other

8

metabolites. The inhibitory effects of SC1 glucuronides were time-dependently enhanced,

9

associated with the intracellular accumulation of SC1 and the methylated form. SC1 glucuronides

10

and SC1 attenuated the expression of the inducible NO synthase (iNOS) and the upstream

11

#

H =&$

H> in the LPS-stimulated macrophages. The inhibitory effects of SC1

12

glucuronides against NO production were cancelled by the H 8(

13

by the catechol-O-methyltransferase inhibitor. Our results suggest that SC1 glucuronides exert the

14

anti-inflammatory effects by inhibiting the &$

15

mediated deconjugation.

16

KEYWORDS: Sesamin / Deconjugation / Macrophage / Anti-inflammation / Nitric oxide

HE

%

inhibitor and enhanced

signaling through the macrophage-

2 ACS Paragon Plus Environment

Page 3 of 39

17

Journal of Agricultural and Food Chemistry

INTRODUCTION

18

Seeds and oils of sesame (Sesamum indicum L.) have long been recognized as traditional

19

healthy foods in East Asian countries. Sesame seeds are a rich source of various nutrients, such as

20

lipids, proteins, vitamins and minerals

21

have attracted significant attention for their contribution to the biological activities and are

22

commercially available as nutraceuticals in the form of capsules for an antioxidant function. The

23

major sesame lignans are lipophilic sesamin and sesamolin in sesame oils and hydrophilic

24

sesaminol glucosides in sesame seed cakes 3.

25

Sesamin, =-F -GF /F /GF> 1