The University of Southampton
University of Southampton Institutional Repository

Green tea polyphenolic antioxidants oxidize hydrogen sulfide to thiosulfate and polysulfides: A possible new mechanism underpinning their biological action

Green tea polyphenolic antioxidants oxidize hydrogen sulfide to thiosulfate and polysulfides: A possible new mechanism underpinning their biological action
Green tea polyphenolic antioxidants oxidize hydrogen sulfide to thiosulfate and polysulfides: A possible new mechanism underpinning their biological action

Matcha and green tea catechins such as (-)-epicatechin (EC), (-)-epigallocatechin (EGC) and (-)-epigallocatechin gallate (EGCG) have long been studied for their antioxidant and health-promoting effects. Using specific fluorophores for H2S (AzMC) and polysulfides (SSP4) as well as IC-MS and UPLC-MS/MS-based techniques we here show that popular Japanese and Chinese green teas and select catechins all catalytically oxidize hydrogen sulfide (H2S) to polysulfides with the potency of EGC > EGCG >> EG. This reaction is accompanied by the formation of sulfite, thiosulfate and sulfate, consumes oxygen and is partially inhibited by the superoxide scavenger, tempol, and superoxide dismutase but not mannitol, trolox, DMPO, or the iron chelator, desferrioxamine. We propose that the reaction proceeds via a one-electron autoxidation process during which one of the OH-groups of the catechin B-ring is autooxidized to a semiquinone radical and oxygen is reduced to superoxide, either of which can then oxidize HS- to thiyl radicals (HS•) which react to form hydrogen persulfide (H2S2). H2S oxidation reduces the B-ring back to the hydroquinone for recycling while the superoxide is reduced to hydrogen peroxide (H2O2). Matcha and catechins also concentration-dependently and rapidly produce polysulfides in HEK293 cells with the potency order EGCG > EGC > EG, an EGCG threshold of ~300 nM, and an EC50 of ~3 μM, suggesting green tea also acts as powerful pro-oxidant in vivo. The resultant polysulfides formed are not only potent antioxidants, but elicit a cascade of secondary cytoprotective effects, and we propose that many of the health benefits of green tea are mediated through these reactions. Remarkably, all green tea leaves constitutively contain small amounts of H2S2.

Antioxidants/pharmacology, Catechin/pharmacology, Chromatography, Liquid, HEK293 Cells, Humans, Hydrogen Peroxide, Hydrogen Sulfide, Sulfides, Tandem Mass Spectrometry, Tea, Thiosulfates
2213-2317
2213-2217
Olson, Kenneth R
82b73d34-60b6-4915-9328-c50805bea090
Briggs, Austin
69d3fae3-99fd-4995-92db-045330e43e33
Devireddy, Monesh
1aafe73c-2fb8-4159-85be-63937f6f9b77
Iovino, Nicholas A
a0bd79f4-4f8e-492c-a085-ccd0878a8c91
Skora, Nicole C
eecdb9d8-016e-44be-a03c-31c2b32d903c
Whelan, Jenna
fba43eb6-48b0-4300-99d0-6cd0aebaafc9
Villa, Brian P
a67fc5d8-c71b-471d-9e76-660cecb9ae9a
Yuan, Xiaotong
dcf9c337-fa50-4764-8c04-54129ed316f9
Mannam, Varun
91f2380a-d8ad-40be-87fd-20427347450f
Howard, Scott
977c84c4-b1e4-4acc-ae5a-fb9f576ac28f
Gao, Yan
23154085-596b-483e-8c31-79916fca87ea
Minnion, Magdalena
ab23b32b-9f8e-4876-aaf5-99cb6a725a2f
Feelisch, Martin
8c1b9965-8614-4e85-b2c6-458a2e17eafd
Olson, Kenneth R
82b73d34-60b6-4915-9328-c50805bea090
Briggs, Austin
69d3fae3-99fd-4995-92db-045330e43e33
Devireddy, Monesh
1aafe73c-2fb8-4159-85be-63937f6f9b77
Iovino, Nicholas A
a0bd79f4-4f8e-492c-a085-ccd0878a8c91
Skora, Nicole C
eecdb9d8-016e-44be-a03c-31c2b32d903c
Whelan, Jenna
fba43eb6-48b0-4300-99d0-6cd0aebaafc9
Villa, Brian P
a67fc5d8-c71b-471d-9e76-660cecb9ae9a
Yuan, Xiaotong
dcf9c337-fa50-4764-8c04-54129ed316f9
Mannam, Varun
91f2380a-d8ad-40be-87fd-20427347450f
Howard, Scott
977c84c4-b1e4-4acc-ae5a-fb9f576ac28f
Gao, Yan
23154085-596b-483e-8c31-79916fca87ea
Minnion, Magdalena
ab23b32b-9f8e-4876-aaf5-99cb6a725a2f
Feelisch, Martin
8c1b9965-8614-4e85-b2c6-458a2e17eafd

Olson, Kenneth R, Briggs, Austin, Devireddy, Monesh, Iovino, Nicholas A, Skora, Nicole C, Whelan, Jenna, Villa, Brian P, Yuan, Xiaotong, Mannam, Varun, Howard, Scott, Gao, Yan, Minnion, Magdalena and Feelisch, Martin (2020) Green tea polyphenolic antioxidants oxidize hydrogen sulfide to thiosulfate and polysulfides: A possible new mechanism underpinning their biological action. Redox Biology, 37, 2213-2217, [101731]. (doi:10.1016/j.redox.2020.101731).

Record type: Article

Abstract

Matcha and green tea catechins such as (-)-epicatechin (EC), (-)-epigallocatechin (EGC) and (-)-epigallocatechin gallate (EGCG) have long been studied for their antioxidant and health-promoting effects. Using specific fluorophores for H2S (AzMC) and polysulfides (SSP4) as well as IC-MS and UPLC-MS/MS-based techniques we here show that popular Japanese and Chinese green teas and select catechins all catalytically oxidize hydrogen sulfide (H2S) to polysulfides with the potency of EGC > EGCG >> EG. This reaction is accompanied by the formation of sulfite, thiosulfate and sulfate, consumes oxygen and is partially inhibited by the superoxide scavenger, tempol, and superoxide dismutase but not mannitol, trolox, DMPO, or the iron chelator, desferrioxamine. We propose that the reaction proceeds via a one-electron autoxidation process during which one of the OH-groups of the catechin B-ring is autooxidized to a semiquinone radical and oxygen is reduced to superoxide, either of which can then oxidize HS- to thiyl radicals (HS•) which react to form hydrogen persulfide (H2S2). H2S oxidation reduces the B-ring back to the hydroquinone for recycling while the superoxide is reduced to hydrogen peroxide (H2O2). Matcha and catechins also concentration-dependently and rapidly produce polysulfides in HEK293 cells with the potency order EGCG > EGC > EG, an EGCG threshold of ~300 nM, and an EC50 of ~3 μM, suggesting green tea also acts as powerful pro-oxidant in vivo. The resultant polysulfides formed are not only potent antioxidants, but elicit a cascade of secondary cytoprotective effects, and we propose that many of the health benefits of green tea are mediated through these reactions. Remarkably, all green tea leaves constitutively contain small amounts of H2S2.

This record has no associated files available for download.

More information

e-pub ahead of print date: 18 September 2020
Published date: 1 October 2020
Additional Information: © 2020 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY-NC-ND license
Keywords: Antioxidants/pharmacology, Catechin/pharmacology, Chromatography, Liquid, HEK293 Cells, Humans, Hydrogen Peroxide, Hydrogen Sulfide, Sulfides, Tandem Mass Spectrometry, Tea, Thiosulfates

Identifiers

Local EPrints ID: 457858
URI: http://eprints.soton.ac.uk/id/eprint/457858
ISSN: 2213-2317
PURE UUID: 94656ddb-a4ba-487b-80b6-64bfe291d279
ORCID for Martin Feelisch: ORCID iD orcid.org/0000-0003-2320-1158

Catalogue record

Date deposited: 20 Jun 2022 17:01
Last modified: 04 Aug 2022 01:46

Export record

Altmetrics

Contributors

Author: Kenneth R Olson
Author: Austin Briggs
Author: Monesh Devireddy
Author: Nicholas A Iovino
Author: Nicole C Skora
Author: Jenna Whelan
Author: Brian P Villa
Author: Xiaotong Yuan
Author: Varun Mannam
Author: Scott Howard
Author: Yan Gao
Author: Magdalena Minnion
Author: Martin Feelisch ORCID iD

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×