Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation

Dahong Li; Shengtao Xu; Hao Cai; Lingling Pei; Hengyuan Zhang; Lei Wang; Hequan Yao; Xiaoming Wu; Jieyun Jiang; Yijun Sun; Jinyi Xu

doi:10.1016/j.ejmech.2013.04.012

Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation

Dahong Li, Shengtao Xu, Hao Cai, Lingling Pei, Hengyuan Zhang, Lei Wang, Hequan Yao, Xiaoming Wu, Jieyun Jiang, Yijun Sun, Jinyi Xu

Microbiology, Immunology, and Molecular Genetics

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

36 Scopus citations

Abstract

A series of enmein-type diterpenoid analogs (11-20) derived from natural kaurene-type diterpenoid oridonin were synthesized and biologically evaluated. All target compounds showed improved anti-proliferative activities against four human cancer cell lines compared with natural oridonin and parent compound 10. Some compounds were more potent than positive control Taxol. Furthermore, mechanistic investigation showed that the representative compound 17 affected cell cycle and induced apoptosis at low micro-molar level in human hepatoma Bel-7402 cells, via an oxidative stress triggered mitochondria-related caspase-dependent pathway.

Original language	English
Pages (from-to)	215-221
Number of pages	7
Journal	European Journal of Medicinal Chemistry
Volume	64
DOIs	https://doi.org/10.1016/j.ejmech.2013.04.012
State	Published - 2013

Bibliographical note

Funding Information:
This study was supported by a grant from the National Natural Science Foundation (No. 30973610 ), Specialized Research Fund for the Doctoral Program of Higher Education (No. 20100096110001 ), Project for Research and Innovation of Graduates in Universities of Jiangsu Province ( CXZZ11-0800 ), the Fundamental Research Funds for the Central Universities ( JKY2011030 ) and Key Fund of Ministry of Education of China (No. 108069 ) for financial assistance.

Keywords

Anti-proliferative activity
Apoptosis
Cell cycle analysis
Enmein-type diterpenoid
Oridonin

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.ejmech.2013.04.012

Cite this

@article{07e6e573c58c41df860548f9e3507558,

title = "Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation",

abstract = "A series of enmein-type diterpenoid analogs (11-20) derived from natural kaurene-type diterpenoid oridonin were synthesized and biologically evaluated. All target compounds showed improved anti-proliferative activities against four human cancer cell lines compared with natural oridonin and parent compound 10. Some compounds were more potent than positive control Taxol. Furthermore, mechanistic investigation showed that the representative compound 17 affected cell cycle and induced apoptosis at low micro-molar level in human hepatoma Bel-7402 cells, via an oxidative stress triggered mitochondria-related caspase-dependent pathway.",

keywords = "Anti-proliferative activity, Apoptosis, Cell cycle analysis, Enmein-type diterpenoid, Oridonin",

author = "Dahong Li and Shengtao Xu and Hao Cai and Lingling Pei and Hengyuan Zhang and Lei Wang and Hequan Yao and Xiaoming Wu and Jieyun Jiang and Yijun Sun and Jinyi Xu",

note = "Funding Information: This study was supported by a grant from the National Natural Science Foundation (No. 30973610 ), Specialized Research Fund for the Doctoral Program of Higher Education (No. 20100096110001 ), Project for Research and Innovation of Graduates in Universities of Jiangsu Province ( CXZZ11-0800 ), the Fundamental Research Funds for the Central Universities ( JKY2011030 ) and Key Fund of Ministry of Education of China (No. 108069 ) for financial assistance. ",

year = "2013",

doi = "10.1016/j.ejmech.2013.04.012",

language = "English",

volume = "64",

pages = "215--221",

}

TY - JOUR

T1 - Enmein-type diterpenoid analogs from natural kaurene-type oridonin

T2 - Synthesis and their antitumor biological evaluation

AU - Li, Dahong

AU - Xu, Shengtao

AU - Cai, Hao

AU - Pei, Lingling

AU - Zhang, Hengyuan

AU - Wang, Lei

AU - Yao, Hequan

AU - Wu, Xiaoming

AU - Jiang, Jieyun

AU - Sun, Yijun

AU - Xu, Jinyi

N1 - Funding Information: This study was supported by a grant from the National Natural Science Foundation (No. 30973610 ), Specialized Research Fund for the Doctoral Program of Higher Education (No. 20100096110001 ), Project for Research and Innovation of Graduates in Universities of Jiangsu Province ( CXZZ11-0800 ), the Fundamental Research Funds for the Central Universities ( JKY2011030 ) and Key Fund of Ministry of Education of China (No. 108069 ) for financial assistance.

PY - 2013

Y1 - 2013

N2 - A series of enmein-type diterpenoid analogs (11-20) derived from natural kaurene-type diterpenoid oridonin were synthesized and biologically evaluated. All target compounds showed improved anti-proliferative activities against four human cancer cell lines compared with natural oridonin and parent compound 10. Some compounds were more potent than positive control Taxol. Furthermore, mechanistic investigation showed that the representative compound 17 affected cell cycle and induced apoptosis at low micro-molar level in human hepatoma Bel-7402 cells, via an oxidative stress triggered mitochondria-related caspase-dependent pathway.

AB - A series of enmein-type diterpenoid analogs (11-20) derived from natural kaurene-type diterpenoid oridonin were synthesized and biologically evaluated. All target compounds showed improved anti-proliferative activities against four human cancer cell lines compared with natural oridonin and parent compound 10. Some compounds were more potent than positive control Taxol. Furthermore, mechanistic investigation showed that the representative compound 17 affected cell cycle and induced apoptosis at low micro-molar level in human hepatoma Bel-7402 cells, via an oxidative stress triggered mitochondria-related caspase-dependent pathway.

KW - Anti-proliferative activity

KW - Apoptosis

KW - Cell cycle analysis

KW - Enmein-type diterpenoid

KW - Oridonin

UR - http://www.scopus.com/inward/record.url?scp=84877025427&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84877025427&partnerID=8YFLogxK

U2 - 10.1016/j.ejmech.2013.04.012

DO - 10.1016/j.ejmech.2013.04.012

M3 - Article

C2 - 23644204

AN - SCOPUS:84877025427

SN - 0223-5234

VL - 64

SP - 215

EP - 221

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this