Synthesis and biological evaluation of ambradiolic acid as an inhibitor of glycogen phosphorylase

Jie Liu; Hengyuan Zhang; Peiqing Zhu; Xiaoming Wu; Hequan Yao; Wencai Ye; Jieyun Jiang; Jinyi Xu

doi:10.1016/j.fitote.2014.11.014

Synthesis and biological evaluation of ambradiolic acid as an inhibitor of glycogen phosphorylase

Jie Liu, Hengyuan Zhang, Peiqing Zhu, Xiaoming Wu, Hequan Yao, Wencai Ye, Jieyun Jiang, Jinyi Xu

Microbiology, Immunology, and Molecular Genetics

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Ambradiolic acid (3) with oleanane skeleton is a natural pentacyclictriterpene. The first synthesis of 3 starting from 23-hydroxybetulinic acid (2) has been accomplished in 12-steps with a total yield of 18.1% in our study. Compound 3 was further biologically evaluated and found to exhibit significant inhibitory activity against rabbit muscle glycogen phosphorylase (GP) with an IC50 value of 12.4 μM, suggesting it could be a potential lead compound for the development of hypoglycemic drugs.

Original language	English
Pages (from-to)	50-55
Number of pages	6
Journal	Fitoterapia
Volume	100
DOIs	https://doi.org/10.1016/j.fitote.2014.11.014
State	Published - Jan 2015

Bibliographical note

Funding Information:
The project was funded by the National Natural Science Foundation of China (No. 81273377 ), Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Ministry of Education of China (No. CMEMR2013-B05 ) and the Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University (No. SKLNMZZCX201404 ).

Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.

Keywords

23-Hydroxybetulinic acid
Ambradiolic acid
First synthesis
Glycogen phosphorylase (GP)

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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10.1016/j.fitote.2014.11.014

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title = "Synthesis and biological evaluation of ambradiolic acid as an inhibitor of glycogen phosphorylase",

abstract = "Ambradiolic acid (3) with oleanane skeleton is a natural pentacyclictriterpene. The first synthesis of 3 starting from 23-hydroxybetulinic acid (2) has been accomplished in 12-steps with a total yield of 18.1% in our study. Compound 3 was further biologically evaluated and found to exhibit significant inhibitory activity against rabbit muscle glycogen phosphorylase (GP) with an IC50 value of 12.4 μM, suggesting it could be a potential lead compound for the development of hypoglycemic drugs.",

keywords = "23-Hydroxybetulinic acid, Ambradiolic acid, First synthesis, Glycogen phosphorylase (GP)",

author = "Jie Liu and Hengyuan Zhang and Peiqing Zhu and Xiaoming Wu and Hequan Yao and Wencai Ye and Jieyun Jiang and Jinyi Xu",

note = "Funding Information: The project was funded by the National Natural Science Foundation of China (No. 81273377 ), Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Ministry of Education of China (No. CMEMR2013-B05 ) and the Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University (No. SKLNMZZCX201404 ). Publisher Copyright: {\textcopyright} 2014 Elsevier B.V. All rights reserved.",

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language = "English",

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AU - Liu, Jie

AU - Zhang, Hengyuan

AU - Zhu, Peiqing

AU - Wu, Xiaoming

AU - Yao, Hequan

AU - Ye, Wencai

AU - Jiang, Jieyun

AU - Xu, Jinyi

N1 - Funding Information: The project was funded by the National Natural Science Foundation of China (No. 81273377 ), Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Ministry of Education of China (No. CMEMR2013-B05 ) and the Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University (No. SKLNMZZCX201404 ). Publisher Copyright: © 2014 Elsevier B.V. All rights reserved.

PY - 2015/1

Y1 - 2015/1

N2 - Ambradiolic acid (3) with oleanane skeleton is a natural pentacyclictriterpene. The first synthesis of 3 starting from 23-hydroxybetulinic acid (2) has been accomplished in 12-steps with a total yield of 18.1% in our study. Compound 3 was further biologically evaluated and found to exhibit significant inhibitory activity against rabbit muscle glycogen phosphorylase (GP) with an IC50 value of 12.4 μM, suggesting it could be a potential lead compound for the development of hypoglycemic drugs.

AB - Ambradiolic acid (3) with oleanane skeleton is a natural pentacyclictriterpene. The first synthesis of 3 starting from 23-hydroxybetulinic acid (2) has been accomplished in 12-steps with a total yield of 18.1% in our study. Compound 3 was further biologically evaluated and found to exhibit significant inhibitory activity against rabbit muscle glycogen phosphorylase (GP) with an IC50 value of 12.4 μM, suggesting it could be a potential lead compound for the development of hypoglycemic drugs.

KW - 23-Hydroxybetulinic acid

KW - Ambradiolic acid

KW - First synthesis

KW - Glycogen phosphorylase (GP)

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JO - Fitoterapia

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Synthesis and biological evaluation of ambradiolic acid as an inhibitor of glycogen phosphorylase

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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