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

Producción científica: Article › revisión exhaustiva

5 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	50-55
Número de páginas	6
Publicación	Fitoterapia
Volumen	100
DOI	https://doi.org/10.1016/j.fitote.2014.11.014
Estado	Published - ene 2015

Nota bibliográfica

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

Financiación

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 ).

Financiadores	Número del financiador
National Natural Science Foundation of China (NSFC)	81273377
Ministry of Education of the People's Republic of China	CMEMR2013-B05
Guangxi Normal University
State Key Laboratory of Natural Medicines, China Pharmaceutical University	SKLNMZZCX201404
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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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",

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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

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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M3 - Article

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AN - SCOPUS:84911890152

SN - 0367-326X

VL - 100

SP - 50

EP - 55

JO - Fitoterapia

JF - Fitoterapia

ER -

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

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

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