Assignment of Absolute Configuration of a New Hepatoprotective Schiartane-Type Nortriterpenoid Using X-Ray Diffraction

Xiaojuan Wang; Frank R Fronczek; Jiabao Chen; Jiabao Liu; Daneel Ferreira; Shuai Li; Mark T Hamann

doi:10.3390/molecules22010065

Assignment of Absolute Configuration of a New Hepatoprotective Schiartane-Type Nortriterpenoid Using X-Ray Diffraction

Molecules. 2017 Jan 2;22(1):65. doi: 10.3390/molecules22010065.

Authors

Xiaojuan Wang^{1

2}, Frank R Fronczek³, Jiabao Chen⁴, Jiabao Liu⁵, Daneel Ferreira⁶, Shuai Li⁷, Mark T Hamann⁸

Affiliations

¹ State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. xiaojuan2013@outlook.com.
² Department of Drug Discovery and Biomedical Sciences, College of Pharmacy, Medical University of South Carolina, Charleston, SC 29425, USA. xiaojuan2013@outlook.com.
³ Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA. ffroncz@lsu.edu.
⁴ State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. cjb427@hotmail.com.
⁵ State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. ljb_5021@hotmail.com.
⁶ Department of BioMolecular Sciences, Division of Pharmacognosy, and Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi 38677-1848, USA. dferreir@olemiss.edu.
⁷ State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. lishuai@imm.ac.cn.
⁸ Department of Drug Discovery and Biomedical Sciences, College of Pharmacy, Medical University of South Carolina, Charleston, SC 29425, USA. hamannm@musc.edu.

Abstract

A new schiartane-type nortriterpenoid, micrandilactone H was isolated from Kadsuralongipedunculata Finet et Gagnep. Its 2D (two dimension) structure was elucidated by NMR spectroscopic analysis, and it is similar to that of Kadnanolactones H and the absolute configuration was established through X-ray diffraction and ECD data analysis. This represents the first complete assignment of the absolute configuration of a schiartane-type nortriterpenoid by X-ray diffraction and the ECD method. Micrandilactone H showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with cell survival rates of 56.84% at 10 μM.

Keywords: X-ray; absolute configuration; hepatoprotective; schiartane-type nortriterpenoid.

MeSH terms

Acetaminophen / toxicity
Apoptosis / drug effects
Cell Proliferation / drug effects
Hep G2 Cells
Humans
Kadsura / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Extracts / chemistry
Plant Extracts / pharmacology
Triterpenes / chemistry*
Triterpenes / pharmacology*
X-Ray Diffraction

Substances

Plant Extracts
Triterpenes
schiartane
Acetaminophen

Grants and funding

R01 AT007318/AT/NCCIH NIH HHS/United States