Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives - Investigations on identified and putative vitamin K2 metabolites

Shinya Fujii; Akitaka Shimizu; Noriaki Takeda; Kazuki Oguchi; Tomoko Katsurai; Hitoshi Shirakawa; Michio Komai; Hiroyuki Kagechika

doi:10.1016/j.bmc.2015.03.070

Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives - Investigations on identified and putative vitamin K₂ metabolites

Shinya Fujii, Akitaka Shimizu, Noriaki Takeda, Kazuki Oguchi, Tomoko Katsurai, Hitoshi Shirakawa, Michio Komai, Hiroyuki Kagechika

AGR - Agricultural Chemistry

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

24 Citations (Scopus)

Abstract

Vitamin K is an essential nutrient for blood coagulation and bone homeostasis, and also functions in many physiological processes including inflammation and cancer progression. However, the nature and activities of its metabolites remain unclear. We report here systematic synthesis of ω-carboxylated derivatives of menaquinone (vitamin K₂), including previously identified metabolites 5, K acid I (10), and K acid II (12), and evaluation of their inhibitory activity toward LPS-stimulated induction of inflammatory cytokines. These results should contribute to an improved understanding of the biochemistry and pharmacology of vitamin K.

Original language	English
Pages (from-to)	2344-2352
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	23
Issue number	10
DOIs	https://doi.org/10.1016/j.bmc.2015.03.070
Publication status	Published - 2015 May 15

Keywords

Anti-inflammatory activity
Menaquinone
Metabolite
Vitamin K

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.bmc.2015.03.070

Cite this

Fujii, S., Shimizu, A., Takeda, N., Oguchi, K., Katsurai, T., Shirakawa, H., Komai, M., & Kagechika, H. (2015). Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives - Investigations on identified and putative vitamin K₂ metabolites. Bioorganic and Medicinal Chemistry, 23(10), 2344-2352. https://doi.org/10.1016/j.bmc.2015.03.070

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title = "Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives - Investigations on identified and putative vitamin K2 metabolites",

abstract = "Vitamin K is an essential nutrient for blood coagulation and bone homeostasis, and also functions in many physiological processes including inflammation and cancer progression. However, the nature and activities of its metabolites remain unclear. We report here systematic synthesis of ω-carboxylated derivatives of menaquinone (vitamin K2), including previously identified metabolites 5, K acid I (10), and K acid II (12), and evaluation of their inhibitory activity toward LPS-stimulated induction of inflammatory cytokines. These results should contribute to an improved understanding of the biochemistry and pharmacology of vitamin K.",

keywords = "Anti-inflammatory activity, Menaquinone, Metabolite, Vitamin K",

author = "Shinya Fujii and Akitaka Shimizu and Noriaki Takeda and Kazuki Oguchi and Tomoko Katsurai and Hitoshi Shirakawa and Michio Komai and Hiroyuki Kagechika",

note = "Funding Information: We are grateful to Nisshin Pharma Inc. for providing MK-4. This study was partially supported by JSPS KAKENHI Grant No. 25460146 (S.F.), No. 23380070 (H.S.), Nos. 22136013 and 23659051 (H.K.), JSPS Core-to-Core Program, A. Advanced Research Networks, and MEXT Platform for Drug Discovery, Informatics, and Structural Life Science, Japan. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

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doi = "10.1016/j.bmc.2015.03.070",

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Fujii, S, Shimizu, A, Takeda, N, Oguchi, K, Katsurai, T, Shirakawa, H, Komai, M & Kagechika, H 2015, 'Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives - Investigations on identified and putative vitamin K₂ metabolites', Bioorganic and Medicinal Chemistry, vol. 23, no. 10, pp. 2344-2352. https://doi.org/10.1016/j.bmc.2015.03.070

Systematic synthesis and anti-inflammatory activity of ω-carboxylated menaquinone derivatives - Investigations on identified and putative vitamin K₂ metabolites. / Fujii, Shinya; Shimizu, Akitaka; Takeda, Noriaki et al.
In: Bioorganic and Medicinal Chemistry, Vol. 23, No. 10, 15.05.2015, p. 2344-2352.

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

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AU - Fujii, Shinya

AU - Shimizu, Akitaka

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AU - Oguchi, Kazuki

AU - Katsurai, Tomoko

AU - Shirakawa, Hitoshi

AU - Komai, Michio

AU - Kagechika, Hiroyuki

N1 - Funding Information: We are grateful to Nisshin Pharma Inc. for providing MK-4. This study was partially supported by JSPS KAKENHI Grant No. 25460146 (S.F.), No. 23380070 (H.S.), Nos. 22136013 and 23659051 (H.K.), JSPS Core-to-Core Program, A. Advanced Research Networks, and MEXT Platform for Drug Discovery, Informatics, and Structural Life Science, Japan. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/5/15

Y1 - 2015/5/15

N2 - Vitamin K is an essential nutrient for blood coagulation and bone homeostasis, and also functions in many physiological processes including inflammation and cancer progression. However, the nature and activities of its metabolites remain unclear. We report here systematic synthesis of ω-carboxylated derivatives of menaquinone (vitamin K2), including previously identified metabolites 5, K acid I (10), and K acid II (12), and evaluation of their inhibitory activity toward LPS-stimulated induction of inflammatory cytokines. These results should contribute to an improved understanding of the biochemistry and pharmacology of vitamin K.

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