Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

Hong Cheng; Ran Liang; Rui-Min Han; Jian-Ping Zhang; Leif Horsfelt Skibsted

doi:10.1039/c3fo60519a

Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

Hong Cheng, Ran Liang, Rui-Min Han, Jian-Ping Zhang, Leif Horsfelt Skibsted

Fødevarekemi

4 Citationer (Scopus)

Abstract

The radical cation generated during photobleaching of β-carotene is scavenged efficiently by the anion of methyl salicylate from wintergreen oil in a second-order reaction approaching the diffusion limit with k₂ = 3.2 × 10⁹ L mol^-1 s^-1 in 9:1 v/v chloroform-methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 10⁸ L mol^-1 s^-1, but still of possible importance for light-exposed tissue. Surprisingly, acetylsalicylate, the aspirin anion, reacts with an intermediate rate in a reaction assigned to the anion of the mixed acetic-salicylic acid anhydride formed through base induced rearrangements. The relative scavenging rate of the β-carotene radical cation by the three salicylates is supported by DFT-calculations.

Originalsprog	Engelsk
Tidsskrift	Food & Function
Vol/bind	5
Udgave nummer	2
Sider (fra-til)	291-294
Antal sider	4
ISSN	2042-6496
DOI	https://doi.org/10.1039/c3fo60519a
Status	Udgivet - feb. 2014

Adgang til dokumentet

10.1039/c3fo60519a

Andre filer og links

Link to publication in Scopus

Citationsformater

@article{32730e0ca80c4152a06c8af00ae8b70c,

title = "Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates",

abstract = "The radical cation generated during photobleaching of β-carotene is scavenged efficiently by the anion of methyl salicylate from wintergreen oil in a second-order reaction approaching the diffusion limit with k2 = 3.2 × 109 L mol-1 s-1 in 9:1 v/v chloroform-methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 108 L mol-1 s-1, but still of possible importance for light-exposed tissue. Surprisingly, acetylsalicylate, the aspirin anion, reacts with an intermediate rate in a reaction assigned to the anion of the mixed acetic-salicylic acid anhydride formed through base induced rearrangements. The relative scavenging rate of the β-carotene radical cation by the three salicylates is supported by DFT-calculations.",

author = "Hong Cheng and Ran Liang and Rui-Min Han and Jian-Ping Zhang and Skibsted, {Leif Horsfelt}",

year = "2014",

month = feb,

doi = "10.1039/c3fo60519a",

language = "English",

volume = "5",

pages = "291--294",

journal = "Food & Function",

issn = "2042-6496",

publisher = "Royal Society of Chemistry",

number = "2",

}

TY - JOUR

T1 - Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

AU - Cheng, Hong

AU - Liang, Ran

AU - Han, Rui-Min

AU - Zhang, Jian-Ping

AU - Skibsted, Leif Horsfelt

PY - 2014/2

Y1 - 2014/2

N2 - The radical cation generated during photobleaching of β-carotene is scavenged efficiently by the anion of methyl salicylate from wintergreen oil in a second-order reaction approaching the diffusion limit with k2 = 3.2 × 109 L mol-1 s-1 in 9:1 v/v chloroform-methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 108 L mol-1 s-1, but still of possible importance for light-exposed tissue. Surprisingly, acetylsalicylate, the aspirin anion, reacts with an intermediate rate in a reaction assigned to the anion of the mixed acetic-salicylic acid anhydride formed through base induced rearrangements. The relative scavenging rate of the β-carotene radical cation by the three salicylates is supported by DFT-calculations.

AB - The radical cation generated during photobleaching of β-carotene is scavenged efficiently by the anion of methyl salicylate from wintergreen oil in a second-order reaction approaching the diffusion limit with k2 = 3.2 × 109 L mol-1 s-1 in 9:1 v/v chloroform-methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 108 L mol-1 s-1, but still of possible importance for light-exposed tissue. Surprisingly, acetylsalicylate, the aspirin anion, reacts with an intermediate rate in a reaction assigned to the anion of the mixed acetic-salicylic acid anhydride formed through base induced rearrangements. The relative scavenging rate of the β-carotene radical cation by the three salicylates is supported by DFT-calculations.

UR - http://www.scopus.com/inward/record.url?scp=84893224409&partnerID=8YFLogxK

U2 - 10.1039/c3fo60519a

DO - 10.1039/c3fo60519a

M3 - Journal article

C2 - 24336797

AN - SCOPUS:84893224409

SN - 2042-6496

VL - 5

SP - 291

EP - 294

JO - Food & Function

JF - Food & Function

IS - 2

ER -

Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

Abstract

Adgang til dokumentet

Andre filer og links

Fingeraftryk

Citationsformater