ent-Abietane-type lactones with anti-inflammatory activity from Euphorbia helioscopia

Hong-Ying Yang; Pei-Zhi Huang; Wei-Jiao Feng; Pei-Wei Si; Kun Gao; Jian-Jun Chen

doi:10.1016/j.phytochem.2024.114313

ent-Abietane-type lactones with anti-inflammatory activity from Euphorbia helioscopia

Phytochemistry. 2025 Jan:229:114313. doi: 10.1016/j.phytochem.2024.114313. Epub 2024 Oct 24.

Authors

Hong-Ying Yang¹, Pei-Zhi Huang¹, Wei-Jiao Feng¹, Pei-Wei Si¹, Kun Gao², Jian-Jun Chen³

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, People's Republic of China.
² State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, People's Republic of China. Electronic address: [email protected].
³ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, People's Republic of China. Electronic address: [email protected].

PMID: 39461493
DOI: 10.1016/j.phytochem.2024.114313

Abstract

Euphohelinodes D-I (1-6), six previously unreported ent-abietane lactones, along with two known analogues (7 and 8), were isolated from the anti-inflammatory fraction extracted from E. helioscopia by a bioactivity-guided isolation. Their structures were characterized using a combination of spectroscopic data interpretation, single-crystal X-ray diffraction and ECD analysis. The anti-inflammatory activity of these compounds was evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW264.7 macrophages. The most active candidate, euphohelinode H (5), had better inhibitory activity against NO production with an IC₅₀ value of 30.23 ± 2.33 μM. Further study revealed that 5 significantly suppressed the expressions of iNOS and COX-2 through the NF-κB signaling pathway.

Keywords: Anti-inflammatory activity; Euphohelinodes D–I; Euphorbia helioscopia L.; Euphorbiaceae; ent-Abietane lactones.

MeSH terms

Abietanes* / chemistry
Abietanes* / isolation & purification
Abietanes* / pharmacology
Animals
Anti-Inflammatory Agents* / chemistry
Anti-Inflammatory Agents* / isolation & purification
Anti-Inflammatory Agents* / pharmacology
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology
Cyclooxygenase 2 / metabolism
Dose-Response Relationship, Drug
Euphorbia* / chemistry
Lactones* / chemistry
Lactones* / isolation & purification
Lactones* / pharmacology
Lipopolysaccharides* / antagonists & inhibitors
Lipopolysaccharides* / pharmacology
Macrophages / drug effects
Macrophages / metabolism
Mice
Molecular Structure
NF-kappa B / antagonists & inhibitors
NF-kappa B / metabolism
Nitric Oxide Synthase Type II / antagonists & inhibitors
Nitric Oxide Synthase Type II / metabolism
Nitric Oxide* / antagonists & inhibitors
Nitric Oxide* / biosynthesis
RAW 264.7 Cells
Structure-Activity Relationship

Substances

Lactones
Abietanes
Nitric Oxide
Lipopolysaccharides
Anti-Inflammatory Agents
NF-kappa B
Nitric Oxide Synthase Type II
Cyclooxygenase 2
Anti-Inflammatory Agents, Non-Steroidal