Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury

Yi MOU; Yan Lin JIAN; Tong CHEN; Zhang Jian HUANG; Yi Xue QIAO; Si Xun PENG; Da Yong ZHANG; Hui JI; Yi Hua ZHANG

doi:10.1016/S1875-5364(17)30055-9

Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury

Yi MOU, Yan Lin JIAN, Tong CHEN, Zhang Jian HUANG, Yi Xue QIAO, Si Xun PENG, Da Yong ZHANG, Hui JI^*, Yi Hua ZHANG

^*Corresponding author for this work

China Pharmaceutical University

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

3 Citations (Scopus)

Abstract

The present study was designed to synthesize 2-Cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide (1), a lactone derivative of oleanolic acid (OA) and evaluate its anti-inflammatory activity. Compound 1 significantly diminished nitric oxide (NO) production and down-regulated the mRNA expression of iNOS, COX-2, IL-6, IL-1β, and TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Further in vivo studies in murine model of LPS-induced acute lung injury (ALI) showed that 1 possessed more potent protective effects than the well-known anti-inflammatory drug dexamethasone by inhibiting myeloperoxidase (MPO) activity, reducing total cells and neutrophils, and suppressing inflammatory cytokines expression, and thus ameliorating the histopathological conditions of the injured lung tissue. In conclusion, compound 1 could be developed as a promising anti-inflammatory agent for intervention of LPS-induced ALI.

Original language	English
Pages (from-to)	347-354
Number of pages	8
Journal	Chinese Journal of Natural Medicines
Volume	15
Issue number	5
DOIs	https://doi.org/10.1016/S1875-5364(17)30055-9
Publication status	Published - May 2017
Externally published	Yes

Keywords

Acute lung injury
Anti-inflammation
Lactone
Oleanolic acid

Access to Document

10.1016/S1875-5364(17)30055-9

Cite this

MOU, Y., JIAN, Y. L., CHEN, T., HUANG, Z. J., QIAO, Y. X., PENG, S. X., ZHANG, D. Y., JI, H., & ZHANG, Y. H. (2017). Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury. Chinese Journal of Natural Medicines, 15(5), 347-354. https://doi.org/10.1016/S1875-5364(17)30055-9

@article{0da7adffc3e040c39f29f9c8b9c1d03d,

title = "Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury",

abstract = "The present study was designed to synthesize 2-Cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide (1), a lactone derivative of oleanolic acid (OA) and evaluate its anti-inflammatory activity. Compound 1 significantly diminished nitric oxide (NO) production and down-regulated the mRNA expression of iNOS, COX-2, IL-6, IL-1β, and TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Further in vivo studies in murine model of LPS-induced acute lung injury (ALI) showed that 1 possessed more potent protective effects than the well-known anti-inflammatory drug dexamethasone by inhibiting myeloperoxidase (MPO) activity, reducing total cells and neutrophils, and suppressing inflammatory cytokines expression, and thus ameliorating the histopathological conditions of the injured lung tissue. In conclusion, compound 1 could be developed as a promising anti-inflammatory agent for intervention of LPS-induced ALI.",

keywords = "Acute lung injury, Anti-inflammation, Lactone, Oleanolic acid",

author = "Yi MOU and JIAN, {Yan Lin} and Tong CHEN and HUANG, {Zhang Jian} and QIAO, {Yi Xue} and PENG, {Si Xun} and ZHANG, {Da Yong} and Hui JI and ZHANG, {Yi Hua}",

note = "Publisher Copyright: {\textcopyright} 2017 China Pharmaceutical University",

year = "2017",

month = may,

doi = "10.1016/S1875-5364(17)30055-9",

language = "English",

volume = "15",

pages = "347--354",

journal = "Chinese Journal of Natural Medicines",

issn = "1875-5364",

number = "5",

}

MOU, Y, JIAN, YL, CHEN, T, HUANG, ZJ, QIAO, YX, PENG, SX, ZHANG, DY, JI, H & ZHANG, YH 2017, 'Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury', Chinese Journal of Natural Medicines, vol. 15, no. 5, pp. 347-354. https://doi.org/10.1016/S1875-5364(17)30055-9

TY - JOUR

T1 - Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury

AU - MOU, Yi

AU - JIAN, Yan Lin

AU - CHEN, Tong

AU - HUANG, Zhang Jian

AU - QIAO, Yi Xue

AU - PENG, Si Xun

AU - ZHANG, Da Yong

AU - JI, Hui

AU - ZHANG, Yi Hua

PY - 2017/5

Y1 - 2017/5

N2 - The present study was designed to synthesize 2-Cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide (1), a lactone derivative of oleanolic acid (OA) and evaluate its anti-inflammatory activity. Compound 1 significantly diminished nitric oxide (NO) production and down-regulated the mRNA expression of iNOS, COX-2, IL-6, IL-1β, and TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Further in vivo studies in murine model of LPS-induced acute lung injury (ALI) showed that 1 possessed more potent protective effects than the well-known anti-inflammatory drug dexamethasone by inhibiting myeloperoxidase (MPO) activity, reducing total cells and neutrophils, and suppressing inflammatory cytokines expression, and thus ameliorating the histopathological conditions of the injured lung tissue. In conclusion, compound 1 could be developed as a promising anti-inflammatory agent for intervention of LPS-induced ALI.

AB - The present study was designed to synthesize 2-Cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide (1), a lactone derivative of oleanolic acid (OA) and evaluate its anti-inflammatory activity. Compound 1 significantly diminished nitric oxide (NO) production and down-regulated the mRNA expression of iNOS, COX-2, IL-6, IL-1β, and TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Further in vivo studies in murine model of LPS-induced acute lung injury (ALI) showed that 1 possessed more potent protective effects than the well-known anti-inflammatory drug dexamethasone by inhibiting myeloperoxidase (MPO) activity, reducing total cells and neutrophils, and suppressing inflammatory cytokines expression, and thus ameliorating the histopathological conditions of the injured lung tissue. In conclusion, compound 1 could be developed as a promising anti-inflammatory agent for intervention of LPS-induced ALI.

KW - Acute lung injury

KW - Anti-inflammation

KW - Lactone

KW - Oleanolic acid

UR - http://www.scopus.com/inward/record.url?scp=85019705595&partnerID=8YFLogxK

U2 - 10.1016/S1875-5364(17)30055-9

DO - 10.1016/S1875-5364(17)30055-9

M3 - Article

C2 - 28558870

AN - SCOPUS:85019705595

SN - 1875-5364

VL - 15

SP - 347

EP - 354

JO - Chinese Journal of Natural Medicines

JF - Chinese Journal of Natural Medicines

IS - 5

ER -

Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this