Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense

Jaeyoung Kwon; Min Jee Kim; Dong Cheol Kim; Haeun Kwon; Seung Mok Ryu; Sang Hee Shim; Yuanqiang Guo; Seung Beom Hong; Joung Han Yim; Youn Chul Kim; Hyuncheol Oh; Dongho Lee

doi:10.1016/j.bioorg.2021.105012

Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense

Jaeyoung Kwon, Min Jee Kim, Dong Cheol Kim, Haeun Kwon, Seung Mok Ryu, Sang Hee Shim, Yuanqiang Guo, Seung Beom Hong, Joung Han Yim, Youn Chul Kim, Hyuncheol Oh, Dongho Lee

Department of Biosystems and Biotechnology

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

6 Citations (Scopus)

Abstract

Inflammation is a vital process that maintains tissue homeostasis. However, it is widely known that uncontrolled inflammation can contribute to the development of various diseases. This study aimed to discover anti-inflammatory metabolites from Penicillium bialowiezense. Seven spiroditerpenoids, including two new compounds, breviones P and Q (1 and 2), were isolated and characterized by various spectroscopic and spectrometric methods. All isolated compounds were initially tested for their inhibitory effects against lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages. Of these, brevione A (3) exhibited this activity with a half-maximal inhibitory concentration value of 9.5 μM. Further mechanistic studies demonstrated that 3 could suppress the expression of pro-inflammatory cytokines and mediators, such as NO, prostaglandin E₂, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12 by inhibiting the activation of nuclear factor-kappa B and c-Jun N-terminal kinase.

Original language	English
Article number	105012
Journal	Bioorganic Chemistry
Volume	113
DOIs	https://doi.org/10.1016/j.bioorg.2021.105012
Publication status	Published - 2021 Aug

Keywords

Anti-inflammatory effect
Brevione
Penicillium bialowiezense
Spiroditerpenoid

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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title = "Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense",

abstract = "Inflammation is a vital process that maintains tissue homeostasis. However, it is widely known that uncontrolled inflammation can contribute to the development of various diseases. This study aimed to discover anti-inflammatory metabolites from Penicillium bialowiezense. Seven spiroditerpenoids, including two new compounds, breviones P and Q (1 and 2), were isolated and characterized by various spectroscopic and spectrometric methods. All isolated compounds were initially tested for their inhibitory effects against lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages. Of these, brevione A (3) exhibited this activity with a half-maximal inhibitory concentration value of 9.5 μM. Further mechanistic studies demonstrated that 3 could suppress the expression of pro-inflammatory cytokines and mediators, such as NO, prostaglandin E2, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12 by inhibiting the activation of nuclear factor-kappa B and c-Jun N-terminal kinase.",

keywords = "Anti-inflammatory effect, Brevione, Penicillium bialowiezense, Spiroditerpenoid",

author = "Jaeyoung Kwon and Kim, {Min Jee} and Kim, {Dong Cheol} and Haeun Kwon and Ryu, {Seung Mok} and Shim, {Sang Hee} and Yuanqiang Guo and Hong, {Seung Beom} and Yim, {Joung Han} and Kim, {Youn Chul} and Hyuncheol Oh and Dongho Lee",

note = "Funding Information: This research was funded by Korea University, Korea Polar Research Institute (Grant: PE21150), National Research Foundation of Korea (NRF-2019R1A2C1006226 and NRF-2019R1A4A1020626), Korea Institute of Science and Technology Program (2Z06482 and 2E31300), and Rural Development Administration (PJ01354902). Publisher Copyright: {\textcopyright} 2021 Elsevier Inc.",

year = "2021",

month = aug,

doi = "10.1016/j.bioorg.2021.105012",

language = "English",

volume = "113",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

publisher = "Academic Press Inc.",

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T1 - Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense

AU - Kwon, Jaeyoung

AU - Kim, Min Jee

AU - Kim, Dong Cheol

AU - Kwon, Haeun

AU - Ryu, Seung Mok

AU - Shim, Sang Hee

AU - Guo, Yuanqiang

AU - Hong, Seung Beom

AU - Yim, Joung Han

AU - Kim, Youn Chul

AU - Oh, Hyuncheol

AU - Lee, Dongho

N1 - Funding Information: This research was funded by Korea University, Korea Polar Research Institute (Grant: PE21150), National Research Foundation of Korea (NRF-2019R1A2C1006226 and NRF-2019R1A4A1020626), Korea Institute of Science and Technology Program (2Z06482 and 2E31300), and Rural Development Administration (PJ01354902). Publisher Copyright: © 2021 Elsevier Inc.

PY - 2021/8

Y1 - 2021/8

N2 - Inflammation is a vital process that maintains tissue homeostasis. However, it is widely known that uncontrolled inflammation can contribute to the development of various diseases. This study aimed to discover anti-inflammatory metabolites from Penicillium bialowiezense. Seven spiroditerpenoids, including two new compounds, breviones P and Q (1 and 2), were isolated and characterized by various spectroscopic and spectrometric methods. All isolated compounds were initially tested for their inhibitory effects against lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages. Of these, brevione A (3) exhibited this activity with a half-maximal inhibitory concentration value of 9.5 μM. Further mechanistic studies demonstrated that 3 could suppress the expression of pro-inflammatory cytokines and mediators, such as NO, prostaglandin E2, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12 by inhibiting the activation of nuclear factor-kappa B and c-Jun N-terminal kinase.

AB - Inflammation is a vital process that maintains tissue homeostasis. However, it is widely known that uncontrolled inflammation can contribute to the development of various diseases. This study aimed to discover anti-inflammatory metabolites from Penicillium bialowiezense. Seven spiroditerpenoids, including two new compounds, breviones P and Q (1 and 2), were isolated and characterized by various spectroscopic and spectrometric methods. All isolated compounds were initially tested for their inhibitory effects against lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages. Of these, brevione A (3) exhibited this activity with a half-maximal inhibitory concentration value of 9.5 μM. Further mechanistic studies demonstrated that 3 could suppress the expression of pro-inflammatory cytokines and mediators, such as NO, prostaglandin E2, interleukin (IL)-1β, tumor necrosis factor-α, IL-6, and IL-12 by inhibiting the activation of nuclear factor-kappa B and c-Jun N-terminal kinase.

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KW - Brevione

KW - Penicillium bialowiezense

KW - Spiroditerpenoid

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Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense

Abstract

Keywords

ASJC Scopus subject areas

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