Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects

Chung Ju; Sumi Song; Sunyoung Hwang; Chorong Kim; Minkyoung Kim; Jail Gu; Yu Kyoung Oh; Kyeong Lee; Jinsun Kwon; Kiho Lee; Won Ki Kim; Yongseok Choi

doi:10.1016/j.bmcl.2013.07.038

Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects

Chung Ju, Sumi Song, Sunyoung Hwang, Chorong Kim, Minkyoung Kim, Jail Gu, Yu Kyoung Oh, Kyeong Lee, Jinsun Kwon, Kiho Lee, Won Ki Kim, Yongseok Choi

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

19 Citations (Scopus)

Abstract

A series of novel (1S)-(-)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen-glucose deprivation-induced neuronal injury and N-methyl-d-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore, compound 3f was identified as a potent anti-ischemic agent in an in vitro ischemic model, potentially due to the inhibition of N-methyl-d-aspartic acid-evoked excitotoxicity and oxidative/nitrosative stress.

Original language	English
Pages (from-to)	5421-5425
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2013.07.038
Publication status	Published - 2013 Oct 1

Keywords

Anti-excitotoxic activity
Anti-ischemic activity
Anti-oxidant activity
Cerebral ischemia
Verbenone

ASJC Scopus subject areas

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

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@article{4f3796b09925498d8e220cbdb4ec9087,

title = "Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects",

abstract = "A series of novel (1S)-(-)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen-glucose deprivation-induced neuronal injury and N-methyl-d-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore, compound 3f was identified as a potent anti-ischemic agent in an in vitro ischemic model, potentially due to the inhibition of N-methyl-d-aspartic acid-evoked excitotoxicity and oxidative/nitrosative stress.",

keywords = "Anti-excitotoxic activity, Anti-ischemic activity, Anti-oxidant activity, Cerebral ischemia, Verbenone",

author = "Chung Ju and Sumi Song and Sunyoung Hwang and Chorong Kim and Minkyoung Kim and Jail Gu and Oh, {Yu Kyoung} and Kyeong Lee and Jinsun Kwon and Kiho Lee and Kim, {Won Ki} and Yongseok Choi",

note = "Funding Information: This research was supported by the Korea Health Technology R&D Project, the Ministry of Health & Welfare ( #A100766 to W.-K.K.) and by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( #2011-0026325 to Y.C.), Republic of Korea. We are grateful to Dr. In-Young Choi for helpful scientific information regarding (S)-cis-verbenol and Dr. Paul L. Prather (University of Arkansas) for careful reading. ",

year = "2013",

month = oct,

day = "1",

doi = "10.1016/j.bmcl.2013.07.038",

language = "English",

volume = "23",

pages = "5421--5425",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects

AU - Ju, Chung

AU - Song, Sumi

AU - Hwang, Sunyoung

AU - Kim, Chorong

AU - Kim, Minkyoung

AU - Gu, Jail

AU - Oh, Yu Kyoung

AU - Lee, Kyeong

AU - Kwon, Jinsun

AU - Lee, Kiho

AU - Kim, Won Ki

AU - Choi, Yongseok

N1 - Funding Information: This research was supported by the Korea Health Technology R&D Project, the Ministry of Health & Welfare ( #A100766 to W.-K.K.) and by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( #2011-0026325 to Y.C.), Republic of Korea. We are grateful to Dr. In-Young Choi for helpful scientific information regarding (S)-cis-verbenol and Dr. Paul L. Prather (University of Arkansas) for careful reading.

PY - 2013/10/1

Y1 - 2013/10/1

N2 - A series of novel (1S)-(-)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen-glucose deprivation-induced neuronal injury and N-methyl-d-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore, compound 3f was identified as a potent anti-ischemic agent in an in vitro ischemic model, potentially due to the inhibition of N-methyl-d-aspartic acid-evoked excitotoxicity and oxidative/nitrosative stress.

AB - A series of novel (1S)-(-)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen-glucose deprivation-induced neuronal injury and N-methyl-d-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore, compound 3f was identified as a potent anti-ischemic agent in an in vitro ischemic model, potentially due to the inhibition of N-methyl-d-aspartic acid-evoked excitotoxicity and oxidative/nitrosative stress.

KW - Anti-excitotoxic activity

KW - Anti-ischemic activity

KW - Anti-oxidant activity

KW - Cerebral ischemia

KW - Verbenone

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DO - 10.1016/j.bmcl.2013.07.038

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AN - SCOPUS:84883487187

SN - 0960-894X

VL - 23

SP - 5421

EP - 5425

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects

Abstract

Keywords

ASJC Scopus subject areas

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