A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity

Roberta Bernini; Giampiero Gualandi; Claudia Crestini; Maurizio Barontini; Maria Cristina Belfiore; Stefan Willför; Patrik Christoffer Eklund; Raffaele Saladino

doi:10.1016/j.bmc.2009.06.010

A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity

Roberta Bernini, Giampiero Gualandi, Claudia Crestini, Maurizio Barontini, Maria Cristina Belfiore, Stefan Willför, Patrik Christoffer Eklund, Raffaele Saladino

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

19 Citations (Scopus)

Abstract

Highly oxidized lignans produced during the cytochrome P-450 metabolism in the cells show biological activities significantly different from those of their parent natural compounds. Lignans precursors of mammalian enterolignans were treated with a methyltrioxorhenium/hydrogen peroxide catalytic system to afford new compounds oxidized at benzylic as well as in arylic positions. The evaluation of the antioxidant and apoptogenic activity by in vivo protocols of these compounds showed some interesting structure-activity relationships related to the oxidation degree of the molecules. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	Undefined/Unknown
Pages (from-to)	5676–5682
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	15
DOIs	https://doi.org/10.1016/j.bmc.2009.06.010
Publication status	Published - 2009
MoE publication type	A1 Journal article-refereed

Keywords

Antioxidant activity
Apoptogenic activity
Lignans
Methyltrioxorhenium
Ethanol Oxidation

Access to Document

10.1016/j.bmc.2009.06.010

Cite this

Bernini, R., Gualandi, G., Crestini, C., Barontini, M., Cristina Belfiore, M., Willför, S., Eklund, P. C., & Saladino, R. (2009). A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity. Bioorganic and Medicinal Chemistry, 17(15), 5676–5682. https://doi.org/10.1016/j.bmc.2009.06.010

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abstract = "Highly oxidized lignans produced during the cytochrome P-450 metabolism in the cells show biological activities significantly different from those of their parent natural compounds. Lignans precursors of mammalian enterolignans were treated with a methyltrioxorhenium/hydrogen peroxide catalytic system to afford new compounds oxidized at benzylic as well as in arylic positions. The evaluation of the antioxidant and apoptogenic activity by in vivo protocols of these compounds showed some interesting structure-activity relationships related to the oxidation degree of the molecules. (C) 2009 Elsevier Ltd. All rights reserved.",

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author = "Roberta Bernini and Giampiero Gualandi and Claudia Crestini and Maurizio Barontini and {Cristina Belfiore}, Maria and Stefan Willf{\"o}r and Eklund, {Patrik Christoffer} and Raffaele Saladino",

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Bernini, R, Gualandi, G, Crestini, C, Barontini, M, Cristina Belfiore, M, Willför, S , Eklund, PC & Saladino, R 2009, 'A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity', Bioorganic and Medicinal Chemistry, vol. 17, no. 15, pp. 5676–5682. https://doi.org/10.1016/j.bmc.2009.06.010

A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity. / Bernini, Roberta; Gualandi, Giampiero; Crestini, Claudia et al.
In: Bioorganic and Medicinal Chemistry, Vol. 17, No. 15, 2009, p. 5676–5682.

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

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AU - Bernini, Roberta

AU - Gualandi, Giampiero

AU - Crestini, Claudia

AU - Barontini, Maurizio

AU - Cristina Belfiore, Maria

AU - Willför, Stefan

AU - Eklund, Patrik Christoffer

AU - Saladino, Raffaele

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KW - Antioxidant activity

KW - Apoptogenic activity

KW - Lignans

KW - Methyltrioxorhenium

KW - Ethanol Oxidation

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