Triterpenoids from Cyclocarya paliurus and their inhibitory effect on the secretion of apoliprotein B48 in Caco-2 cells

Zheng-Feng Wu; Fan-Cheng Meng; Lan-Jie Cao; Cui-Hua Jiang; Meng-Ge Zhao; Xu-Lan Shang; Sheng-Zuo Fang; Wen-Cai Ye; Qing-Wen Zhang; Jian Zhang; Zhi-Qi Yin

doi:10.1016/j.phytochem.2017.06.015

Triterpenoids from Cyclocarya paliurus and their inhibitory effect on the secretion of apoliprotein B48 in Caco-2 cells

Phytochemistry. 2017 Oct:142:76-84. doi: 10.1016/j.phytochem.2017.06.015. Epub 2017 Jul 6.

Authors

Zheng-Feng Wu¹, Fan-Cheng Meng², Lan-Jie Cao¹, Cui-Hua Jiang³, Meng-Ge Zhao¹, Xu-Lan Shang⁴, Sheng-Zuo Fang⁴, Wen-Cai Ye⁵, Qing-Wen Zhang⁶, Jian Zhang⁷, Zhi-Qi Yin⁸

Affiliations

¹ Department of Natural Medicinal Chemistry & State Key Laboratory of Natural Medicines, 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 Natural Medicinal Chemistry & State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, PR China; State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao SAR, PR China.
³ Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing, 210028, PR China.
⁴ College of Forestry, Nanjing Forestry University, Nanjing, 210037, PR China.
⁵ Institute of Traditional Chinese Medicine and Natural Products & Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Jinan University, Guangzhou, 510632, PR China.
⁶ State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao SAR, PR China.
⁷ Laboratory of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing, 210028, PR China. Electronic address: zhangjian@jsatcm.com.
⁸ Department of Natural Medicinal Chemistry & State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, PR China. Electronic address: cpu-yzq@cpu.edu.cn.

PMID: 28688991
DOI: 10.1016/j.phytochem.2017.06.015

Abstract

Five previously undescribed compounds including two triterpenoid aglycones, 3β,23-dihydroxy-1,12-dioxo-olean-28-oic acid and 3β,23,27-trihydroxy-1-oxo-olean-12-ene-28-oic acid, and three triterpenoid glucosides cyclocarioside L-N, along with 17 known compounds were isolated from a CH₃Cl-soluble extract of the leaves of Cyclocarya paliurus. Two 27-nor-triterpenoid glycosides were isolated from the genus for the first time. Furthermore, the characterized compounds were tested for the inhibitory effects on apoliprotein B48 secretion in Caco-2 cells. Seven triterpenoid aglycones together with four triterpenoid saponins significantly decreased the apoliprotein B48 oversecretion induced by oleic acid in Caco-2 cells.

Keywords: Apoliprotein B48; Cyclocarioside; Cyclocarya paliurus; Juglandaceae; Triterpenoids.

MeSH terms

Apolipoprotein B-48 / antagonists & inhibitors*
Caco-2 Cells
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification*
Drugs, Chinese Herbal / pharmacology*
Glycosides / chemistry
Glycosides / isolation & purification
Humans
Juglandaceae / chemistry*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oleic Acid / pharmacology
Plant Leaves / drug effects
Saponins / chemistry
Saponins / isolation & purification
Saponins / pharmacology
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / pharmacology*

Substances

Apolipoprotein B-48
Drugs, Chinese Herbal
Glycosides
Saponins
Triterpenes
cyclocarioside A
Oleic Acid