Pentacyclic triterpenoids from Cyclocarya paliurus and their antioxidant activities in FFA-induced HepG2 steatosis cells

Hui-Min Yang; Zhi-Qi Yin; Meng-Ge Zhao; Cui-Hua Jiang; Jian Zhang; Ke Pan

doi:10.1016/j.phytochem.2018.03.010

Pentacyclic triterpenoids from Cyclocarya paliurus and their antioxidant activities in FFA-induced HepG2 steatosis cells

Phytochemistry. 2018 Jul:151:119-127. doi: 10.1016/j.phytochem.2018.03.010. Epub 2018 Apr 19.

Authors

Hui-Min Yang¹, Zhi-Qi Yin², Meng-Ge Zhao³, Cui-Hua Jiang⁴, Jian Zhang⁵, Ke Pan⁶

Affiliations

¹ Department of Natural Medicinal Chemistry, School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing 210009, PR China; Department of TCMs Pharmaceuticals, School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing 210009, PR China; Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing 210028, PR China.
² Department of TCMs Pharmaceuticals, School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing 210009, PR China.
³ Department of TCMs Pharmaceuticals, School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing 210009, PR China; Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing 210028, PR China.
⁴ Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing 210028, PR China.
⁵ Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing 210028, PR China. Electronic address: zhangjian@jsatcm.com.
⁶ Department of Natural Medicinal Chemistry, School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing 210009, PR China. Electronic address: pan.ke.nj@gmail.com.

PMID: 29679877
DOI: 10.1016/j.phytochem.2018.03.010

Abstract

Six undescribed pentacyclic triterpenoids including four triterpenoid aglycones, 1β,2a,3β,23-tetrahydroxyurs-12-en-28-ursolic acid, 2a,3a,6β,19α,23-pentahydroxyurs-12-en-28-ursolic acid, 2α,3α,20β,23-tetrahydroxyurs-12-en-28-ursolic acid and 1β,2a,3β,23-tetrahydroxyurs-12,20(30)-dien-28-ursolic acid, and two triterpenoid glucosides, 2a,3a,23-trihydroxy-12,20(30)-dien-28-ursolic acid 28-O-β-d-glucopyranoside and 1-oxo-3β,23-dihydroxyolean-12-en-28-oic acid 28-O-β-d-xylopyranoside, along with 5 known triterpenoids were isolated from a CH₃Cl-soluble extract of the leaves of Cyclocarya paliurus. Their structures were established on the basis of chemical and spectroscopic approaches. These compounds were assessed for their antioxidant effects on FFA-induced hepatic steatosis in HepG2 cells. The results revealed that three saponins and two aglycones markedly increased SOD activity and reduced MDA level.

Keywords: Antioxidant effects; Cyclocarya paliurus; FFA-induced hepatic steatosis; Juglandaceae; Pentacyclic triterpenoids.

MeSH terms

Antioxidants / chemistry
Antioxidants / isolation & purification
Antioxidants / pharmacology*
Cell Survival / drug effects
Dose-Response Relationship, Drug
Fatty Acids, Nonesterified
Hep G2 Cells
Hepatocytes / drug effects*
Hepatocytes / metabolism
Hepatocytes / pathology
Humans
Juglandaceae / chemistry*
Molecular Conformation
Oxidative Stress / drug effects
Pentacyclic Triterpenes / chemistry
Pentacyclic Triterpenes / isolation & purification
Pentacyclic Triterpenes / pharmacology*
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
Plant Leaves / chemistry
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Antioxidants
Fatty Acids, Nonesterified
Pentacyclic Triterpenes
Plant Extracts