Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents

Tara Man Kadayat; Dong Eun Kim; Sang Bong Lee; Kyungjin Jung; Sang Eun Park; Ji Ye Hong; Jina Kim; Aarajana Shrestha; Dong Su Kim; Hongchan An; Nayeon Kim; Su Jeong Lee; Sugyeong Kwon; Suhui Kim; Jun Yeon Hwang; Shinae Kim; Dongyup Hahn; Hyukjae Choi; Sang Jip Nam; Yong Hyun Jeon; Jung Jin Hwang; Sung Jin Cho; Jungwook Chin

doi:10.1016/j.bioorg.2021.105027

Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents

Tara Man Kadayat, Dong Eun Kim, Sang Bong Lee, Kyungjin Jung, Sang Eun Park, Ji Ye Hong, Jina Kim, Aarajana Shrestha, Dong Su Kim, Hongchan An, Nayeon Kim, Su Jeong Lee, Sugyeong Kwon, Suhui Kim, Jun Yeon Hwang, Shinae Kim, Dongyup Hahn, Hyukjae Choi, Sang Jip Nam, Yong Hyun JeonJung Jin Hwang, Sung Jin Cho, Jungwook Chin

Department of Chemistry & Nanoscience

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

2 Scopus citations

Abstract

Psiguadial B (8), and its fluoro- (8a), chloro- (8b), and bromo- (8c) derivatives were synthesized using a sodium acetate-catalyzed single step coupling of three components: β-caryophyllene (5), diformylphloroglucinol (11), and benzaldehyde (12). These compounds efficiently and dose-dependently decreased H₂O₂-induced cell death, a quantitative marker of cell death, in primary cultures of mouse cortical neurons. Psiguadial B also decreased neuronal death and accumulation of ROS induced by FeCl₂ in cortical cultures. The in vitro effects of these compounds in lipopolysaccharide (LPS)-induced expression of nitric oxide (NO), and TNF-α and IL-6 by suppressing the NF-κB pathway in immune cells demonstrated their antioxidative and anti-inflammatory activity. The present findings warrant further research on the development of psiguadial B-based neuroprotective agents for the treatment of neurodegenerative diseases, acute brain injuries and immunological disorders.

Original language	English
Article number	105027
Journal	Bioorganic Chemistry
Volume	113
DOIs	https://doi.org/10.1016/j.bioorg.2021.105027
State	Published - Aug 2021

Bibliographical note

Publisher Copyright:
© 2021 Elsevier Inc.

Keywords

Anti-inflammatory effect
Antioxidative effect
Neuroprotective agent
Psiguadial B
Reactive oxygen species
Short synthetic route

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10.1016/j.bioorg.2021.105027

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Man Kadayat, T., Eun Kim, D., Bong Lee, S., Jung, K., Eun Park, S., Hong, J. Y., Kim, J., Shrestha, A., Kim, D. S., An, H., Kim, N., Lee, S. J., Kwon, S., Kim, S., Yeon Hwang, J., Kim, S., Hahn, D., Choi, H., Nam, S. J., ... Chin, J. (2021). Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents. Bioorganic Chemistry, 113, Article 105027. https://doi.org/10.1016/j.bioorg.2021.105027

@article{d06252f00979403f9f4c3d0b22ebcdb0,

title = "Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents",

abstract = "Psiguadial B (8), and its fluoro- (8a), chloro- (8b), and bromo- (8c) derivatives were synthesized using a sodium acetate-catalyzed single step coupling of three components: β-caryophyllene (5), diformylphloroglucinol (11), and benzaldehyde (12). These compounds efficiently and dose-dependently decreased H2O2-induced cell death, a quantitative marker of cell death, in primary cultures of mouse cortical neurons. Psiguadial B also decreased neuronal death and accumulation of ROS induced by FeCl2 in cortical cultures. The in vitro effects of these compounds in lipopolysaccharide (LPS)-induced expression of nitric oxide (NO), and TNF-α and IL-6 by suppressing the NF-κB pathway in immune cells demonstrated their antioxidative and anti-inflammatory activity. The present findings warrant further research on the development of psiguadial B-based neuroprotective agents for the treatment of neurodegenerative diseases, acute brain injuries and immunological disorders.",

keywords = "Anti-inflammatory effect, Antioxidative effect, Neuroprotective agent, Psiguadial B, Reactive oxygen species, Short synthetic route",

author = "{Man Kadayat}, Tara and {Eun Kim}, Dong and {Bong Lee}, Sang and Kyungjin Jung and {Eun Park}, Sang and Hong, {Ji Ye} and Jina Kim and Aarajana Shrestha and Kim, {Dong Su} and Hongchan An and Nayeon Kim and Lee, {Su Jeong} and Sugyeong Kwon and Suhui Kim and {Yeon Hwang}, Jun and Shinae Kim and Dongyup Hahn and Hyukjae Choi and Nam, {Sang Jip} and {Hyun Jeon}, Yong and {Jin Hwang}, Jung and {Jin Cho}, Sung and Jungwook Chin",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Inc.",

year = "2021",

month = aug,

doi = "10.1016/j.bioorg.2021.105027",

language = "English",

volume = "113",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

publisher = "Academic Press Inc.",

}

Man Kadayat, T, Eun Kim, D, Bong Lee, S, Jung, K, Eun Park, S, Hong, JY, Kim, J, Shrestha, A, Kim, DS, An, H, Kim, N, Lee, SJ, Kwon, S, Kim, S, Yeon Hwang, J, Kim, S, Hahn, D, Choi, H, Nam, SJ, Hyun Jeon, Y, Jin Hwang, J, Jin Cho, S & Chin, J 2021, 'Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents', Bioorganic Chemistry, vol. 113, 105027. https://doi.org/10.1016/j.bioorg.2021.105027

TY - JOUR

T1 - Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents

AU - Man Kadayat, Tara

AU - Eun Kim, Dong

AU - Bong Lee, Sang

AU - Jung, Kyungjin

AU - Eun Park, Sang

AU - Hong, Ji Ye

AU - Kim, Jina

AU - Shrestha, Aarajana

AU - Kim, Dong Su

AU - An, Hongchan

AU - Kim, Nayeon

AU - Lee, Su Jeong

AU - Kwon, Sugyeong

AU - Kim, Suhui

AU - Yeon Hwang, Jun

AU - Kim, Shinae

AU - Hahn, Dongyup

AU - Choi, Hyukjae

AU - Nam, Sang Jip

AU - Hyun Jeon, Yong

AU - Jin Hwang, Jung

AU - Jin Cho, Sung

AU - Chin, Jungwook

PY - 2021/8

Y1 - 2021/8

N2 - Psiguadial B (8), and its fluoro- (8a), chloro- (8b), and bromo- (8c) derivatives were synthesized using a sodium acetate-catalyzed single step coupling of three components: β-caryophyllene (5), diformylphloroglucinol (11), and benzaldehyde (12). These compounds efficiently and dose-dependently decreased H2O2-induced cell death, a quantitative marker of cell death, in primary cultures of mouse cortical neurons. Psiguadial B also decreased neuronal death and accumulation of ROS induced by FeCl2 in cortical cultures. The in vitro effects of these compounds in lipopolysaccharide (LPS)-induced expression of nitric oxide (NO), and TNF-α and IL-6 by suppressing the NF-κB pathway in immune cells demonstrated their antioxidative and anti-inflammatory activity. The present findings warrant further research on the development of psiguadial B-based neuroprotective agents for the treatment of neurodegenerative diseases, acute brain injuries and immunological disorders.

AB - Psiguadial B (8), and its fluoro- (8a), chloro- (8b), and bromo- (8c) derivatives were synthesized using a sodium acetate-catalyzed single step coupling of three components: β-caryophyllene (5), diformylphloroglucinol (11), and benzaldehyde (12). These compounds efficiently and dose-dependently decreased H2O2-induced cell death, a quantitative marker of cell death, in primary cultures of mouse cortical neurons. Psiguadial B also decreased neuronal death and accumulation of ROS induced by FeCl2 in cortical cultures. The in vitro effects of these compounds in lipopolysaccharide (LPS)-induced expression of nitric oxide (NO), and TNF-α and IL-6 by suppressing the NF-κB pathway in immune cells demonstrated their antioxidative and anti-inflammatory activity. The present findings warrant further research on the development of psiguadial B-based neuroprotective agents for the treatment of neurodegenerative diseases, acute brain injuries and immunological disorders.

KW - Anti-inflammatory effect

KW - Antioxidative effect

KW - Neuroprotective agent

KW - Psiguadial B

KW - Reactive oxygen species

KW - Short synthetic route

UR - http://www.scopus.com/inward/record.url?scp=85108736253&partnerID=8YFLogxK

U2 - 10.1016/j.bioorg.2021.105027

DO - 10.1016/j.bioorg.2021.105027

M3 - Article

C2 - 34098398

AN - SCOPUS:85108736253

SN - 0045-2068

VL - 113

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

M1 - 105027

ER -

Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents

Abstract

Bibliographical note

Keywords

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