Synthesis of biflavones having a 6-O-7'' linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase

Haiyan Che; Byung Kyu Park; Hyun Lim; Hyun Pyo Kim; Hyeun Wook Chang; Jin Hyun Jeong; Haeil Park

doi:10.1016/j.bmcl.2008.11.017

Synthesis of biflavones having a 6-O-7'' linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase

Haiyan Che, Byung Kyu Park, Hyun Lim, Hyun Pyo Kim, Hyeun Wook Chang, Jin Hyun Jeong, Haeil Park

Department of Pharmacy

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

14 Citations (Scopus)

Abstract

In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7″ linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7″ biflavone) potently inhibited COX-2-mediated PGE₂ production (IC₅₀: < 2 μM), being less active on iNOS-mediated NO production (IC₅₀: > 50 μM) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7″) reduced the inhibitory activity of PGE₂ production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7″) may have a potential for new anti-inflammatory agent.

Original language	English
Pages (from-to)	74-76
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2008.11.017
Publication status	Published - 2009 Jan 1

Bibliographical note

Funding Information:
The present investigation was supported by Grant R01-2004-000-10134-0 from the Basic research program of the Korea Science and Engineering Foundation and post-BK21 project. The authors thank the Pharmacal Research Institute and the Central Laboratory of Kangwon National University for the use of analytical instruments.

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2008.11.017

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title = "Synthesis of biflavones having a 6-O-7'' linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase",

abstract = "In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7″ linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7″ biflavone) potently inhibited COX-2-mediated PGE2 production (IC50: < 2 μM), being less active on iNOS-mediated NO production (IC50: > 50 μM) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7″) reduced the inhibitory activity of PGE2 production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7″) may have a potential for new anti-inflammatory agent.",

author = "Haiyan Che and Park, {Byung Kyu} and Hyun Lim and Kim, {Hyun Pyo} and Chang, {Hyeun Wook} and Jeong, {Jin Hyun} and Haeil Park",

note = "Funding Information: The present investigation was supported by Grant R01-2004-000-10134-0 from the Basic research program of the Korea Science and Engineering Foundation and post-BK21 project. The authors thank the Pharmacal Research Institute and the Central Laboratory of Kangwon National University for the use of analytical instruments. ",

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AU - Lim, Hyun

AU - Kim, Hyun Pyo

AU - Chang, Hyeun Wook

AU - Jeong, Jin Hyun

AU - Park, Haeil

N1 - Funding Information: The present investigation was supported by Grant R01-2004-000-10134-0 from the Basic research program of the Korea Science and Engineering Foundation and post-BK21 project. The authors thank the Pharmacal Research Institute and the Central Laboratory of Kangwon National University for the use of analytical instruments.

PY - 2009/1/1

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N2 - In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7″ linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7″ biflavone) potently inhibited COX-2-mediated PGE2 production (IC50: < 2 μM), being less active on iNOS-mediated NO production (IC50: > 50 μM) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7″) reduced the inhibitory activity of PGE2 production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7″) may have a potential for new anti-inflammatory agent.

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Synthesis of biflavones having a 6-O-7'' linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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