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

Producción científica: Article › revisión exhaustiva

36 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	215-221
Número de páginas	7
Publicación	European Journal of Medicinal Chemistry
Volumen	64
DOI	https://doi.org/10.1016/j.ejmech.2013.04.012
Estado	Published - 2013

Nota bibliográfica

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.

Financiación

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.

Financiadores	Número del financiador
Project for Research and Innovation of Graduates in Universities of Jiangsu Province	CXZZ11-0800
National Natural Science Foundation of China (NSFC)	30973610
Ministry of Education of the People's Republic of China	108069
Fundamental Research Funds for the Central Universities	JKY2011030
Specialized Research Fund for the Doctoral Program of Higher Education of China	20100096110001

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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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",

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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

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SN - 0223-5234

VL - 64

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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

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

ODS de las Naciones Unidas

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