Anti-inflammatory ent-cleistanthane-type diterpenoids from Phyllanthus rheophyticus

Hong-Ying Yang; Pei-Zhi Huang; Qian Ma; Yue Sun; Wei-Jiao Feng; Yi-Lin He; Jian-Jun Chen; Kun Gao

doi:10.1016/j.phytochem.2023.113723

Anti-inflammatory ent-cleistanthane-type diterpenoids from Phyllanthus rheophyticus

Phytochemistry. 2023 Aug:212:113723. doi: 10.1016/j.phytochem.2023.113723. Epub 2023 May 12.

Authors

Hong-Ying Yang¹, Pei-Zhi Huang¹, Qian Ma¹, Yue Sun¹, Wei-Jiao Feng¹, Yi-Lin He², Jian-Jun Chen³, Kun Gao⁴

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China.
² State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China; Research Institute, Lanzhou Jiaotong University, Lanzhou, 730070, People's Republic of China.
³ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China. Electronic address: chenjj@lzu.edu.cn.
⁴ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China. Electronic address: npchem@lzu.edu.cn.

PMID: 37182686
DOI: 10.1016/j.phytochem.2023.113723

Abstract

A bioactivity-guided isolation from the aerial parts of Phyllanthus rheophyticus obtained 17 undescribed ent-cleistanthane-type diterpenoids, namely phyllarheophols A-Q, as well as 12 known analogs. Their structures were characterized by a combination of spectroscopic data interpretation, single-crystal X-ray diffraction and ECD analysis. The anti-inflammatory activities of these compounds were evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW264.7 macrophages, and their preliminary structure-activity relationships were also discussed. Further study showed that promising compounds phyllarheophol D and phyacioid B significantly suppressed the expressions of cytokines and nitric oxide synthase through the NF-κB signaling pathway.

Keywords: Anti-inflammatory activities; Phyllanthaceae; Phyllanthus rheophyticus; Phyllarheophols A−Q; ent-cleistanthane-type diterpenoids.

MeSH terms

Animals
Anti-Inflammatory Agents* / chemistry
Anti-Inflammatory Agents* / isolation & purification
Anti-Inflammatory Agents* / pharmacology
Diterpenes* / chemistry
Diterpenes* / isolation & purification
Diterpenes* / pharmacology
Interleukin-6 / immunology
Interleukin-6 / metabolism
Lipopolysaccharides
Macrophages / drug effects
Macrophages / enzymology
Macrophages / immunology
Macrophages / metabolism
Mice
Molecular Structure
NF-kappa B / metabolism
Nitric Oxide / antagonists & inhibitors
Nitric Oxide Synthase Type II / metabolism
Phyllanthus* / chemistry
Plant Components, Aerial / chemistry
RAW 264.7 Cells
Structure-Activity Relationship
Tumor Necrosis Factor-alpha / immunology
Tumor Necrosis Factor-alpha / metabolism

Substances

Anti-Inflammatory Agents
Diterpenes
Lipopolysaccharides
Nitric Oxide
NF-kappa B
Tumor Necrosis Factor-alpha
Interleukin-6
Nitric Oxide Synthase Type II