Novel ninhydrin adduct of catechin with potent antioxidative activity

Kiyoshi Fukuhara; Akiko Ohno; Ikuo Nakanishi; Kohei Imai; Asao Nakamura; Kazunori Anzai; Naoki Miyata; Haruhiro Okuda

doi:10.1016/j.tetlet.2009.09.149

Novel ninhydrin adduct of catechin with potent antioxidative activity

Kiyoshi Fukuhara, Akiko Ohno, Ikuo Nakanishi, Kohei Imai, Asao Nakamura, Kazunori Anzai, Naoki Miyata, Haruhiro Okuda

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

The reaction of ninhydrin with (+)-catechin in the presence of TMSOTf resulted in condensation product 1, which consists of a 2:1 mixture of epimers at the C-2 position. The antioxidative radical-scavenging activity of 1 against the galvinoxyl radical, acting as an oxyl radical, was significantly enhanced compared to (+)-catechin. Our results offer a new method for chemical modification of a natural phenolic antioxidant.

Original language	English
Pages (from-to)	6989-6992
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2009.09.149
Publication status	Published - 2009 Dec 16

Keywords

Antioxidant
Catechin
Galvinoxyl radical
Ninhydrin
Radical scavenging

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.09.149

Cite this

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title = "Novel ninhydrin adduct of catechin with potent antioxidative activity",

abstract = "The reaction of ninhydrin with (+)-catechin in the presence of TMSOTf resulted in condensation product 1, which consists of a 2:1 mixture of epimers at the C-2 position. The antioxidative radical-scavenging activity of 1 against the galvinoxyl radical, acting as an oxyl radical, was significantly enhanced compared to (+)-catechin. Our results offer a new method for chemical modification of a natural phenolic antioxidant.",

keywords = "Antioxidant, Catechin, Galvinoxyl radical, Ninhydrin, Radical scavenging",

author = "Kiyoshi Fukuhara and Akiko Ohno and Ikuo Nakanishi and Kohei Imai and Asao Nakamura and Kazunori Anzai and Naoki Miyata and Haruhiro Okuda",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 20390038 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan .",

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T1 - Novel ninhydrin adduct of catechin with potent antioxidative activity

AU - Fukuhara, Kiyoshi

AU - Ohno, Akiko

AU - Nakanishi, Ikuo

AU - Imai, Kohei

AU - Nakamura, Asao

AU - Anzai, Kazunori

AU - Miyata, Naoki

AU - Okuda, Haruhiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 20390038 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan .

PY - 2009/12/16

Y1 - 2009/12/16

N2 - The reaction of ninhydrin with (+)-catechin in the presence of TMSOTf resulted in condensation product 1, which consists of a 2:1 mixture of epimers at the C-2 position. The antioxidative radical-scavenging activity of 1 against the galvinoxyl radical, acting as an oxyl radical, was significantly enhanced compared to (+)-catechin. Our results offer a new method for chemical modification of a natural phenolic antioxidant.

AB - The reaction of ninhydrin with (+)-catechin in the presence of TMSOTf resulted in condensation product 1, which consists of a 2:1 mixture of epimers at the C-2 position. The antioxidative radical-scavenging activity of 1 against the galvinoxyl radical, acting as an oxyl radical, was significantly enhanced compared to (+)-catechin. Our results offer a new method for chemical modification of a natural phenolic antioxidant.

KW - Antioxidant

KW - Catechin

KW - Galvinoxyl radical

KW - Ninhydrin

KW - Radical scavenging

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DO - 10.1016/j.tetlet.2009.09.149

M3 - Article

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EP - 6992

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

Novel ninhydrin adduct of catechin with potent antioxidative activity

Abstract

Keywords

ASJC Scopus subject areas

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