Synthesis and anticancer activity of novel oleanolic acid derivatives

Ye Ding; Zhen Zhen Zhang; Zhang Jian Huang; Yi Mou; Hui Ji; Yi Sheng Lai; Yi Hua Zhang

Synthesis and anticancer activity of novel oleanolic acid derivatives

Ye Ding, Zhen Zhen Zhang, Zhang Jian Huang, Yi Mou, Hui Ji, Yi Sheng Lai, Yi Hua Zhang

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

Abstract

Starting from oleanolic acid (OA), the target compounds (10a-10i) were synthesized via introducting α,β-unsaturated ketone moiety to OA by 7-step successive reactions including benzylation, acetylation, oxidization, bromine substitution-elimination, etc., followed by coupling of C28-carboxyl with substituted furoxans via a glycine linker. All the target compounds were identified by IR, MS and ¹H NMR. MTT assay results showed that compounds 10a-10i displayed much stronger inhibitory effects than OA on the proliferation of four human tumor cell lines. The anti-proliferative activity of 10a-10e and 10i against human hepatoma HepG2 cell was comparable to that of the positive control 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester (CDDO-Me).

Original language	English (US)
Pages (from-to)	385-391
Number of pages	7
Journal	Journal of China Pharmaceutical University
Volume	42
Issue number	5
State	Published - Oct 2011
Externally published	Yes

Keywords

Anticancer activity
Furoxan
NO donor
Oleanolic acid
α,β-unsaturated ketone

ASJC Scopus subject areas

Pharmacology
Pharmaceutical Science

Cite this

@article{f55e6b6999624d3781b007443a99be0c,

title = "Synthesis and anticancer activity of novel oleanolic acid derivatives",

abstract = "Starting from oleanolic acid (OA), the target compounds (10a-10i) were synthesized via introducting α,β-unsaturated ketone moiety to OA by 7-step successive reactions including benzylation, acetylation, oxidization, bromine substitution-elimination, etc., followed by coupling of C28-carboxyl with substituted furoxans via a glycine linker. All the target compounds were identified by IR, MS and 1H NMR. MTT assay results showed that compounds 10a-10i displayed much stronger inhibitory effects than OA on the proliferation of four human tumor cell lines. The anti-proliferative activity of 10a-10e and 10i against human hepatoma HepG2 cell was comparable to that of the positive control 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester (CDDO-Me).",

keywords = "Anticancer activity, Furoxan, NO donor, Oleanolic acid, α,β-unsaturated ketone",

author = "Ye Ding and Zhang, {Zhen Zhen} and Huang, {Zhang Jian} and Yi Mou and Hui Ji and Lai, {Yi Sheng} and Zhang, {Yi Hua}",

year = "2011",

month = oct,

language = "English (US)",

volume = "42",

pages = "385--391",

journal = "Journal of China Pharmaceutical University",

issn = "1000-5048",

publisher = "China Pharmaceutical University",

number = "5",

}

TY - JOUR

T1 - Synthesis and anticancer activity of novel oleanolic acid derivatives

AU - Ding, Ye

AU - Zhang, Zhen Zhen

AU - Huang, Zhang Jian

AU - Mou, Yi

AU - Ji, Hui

AU - Lai, Yi Sheng

AU - Zhang, Yi Hua

PY - 2011/10

Y1 - 2011/10

N2 - Starting from oleanolic acid (OA), the target compounds (10a-10i) were synthesized via introducting α,β-unsaturated ketone moiety to OA by 7-step successive reactions including benzylation, acetylation, oxidization, bromine substitution-elimination, etc., followed by coupling of C28-carboxyl with substituted furoxans via a glycine linker. All the target compounds were identified by IR, MS and 1H NMR. MTT assay results showed that compounds 10a-10i displayed much stronger inhibitory effects than OA on the proliferation of four human tumor cell lines. The anti-proliferative activity of 10a-10e and 10i against human hepatoma HepG2 cell was comparable to that of the positive control 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester (CDDO-Me).

AB - Starting from oleanolic acid (OA), the target compounds (10a-10i) were synthesized via introducting α,β-unsaturated ketone moiety to OA by 7-step successive reactions including benzylation, acetylation, oxidization, bromine substitution-elimination, etc., followed by coupling of C28-carboxyl with substituted furoxans via a glycine linker. All the target compounds were identified by IR, MS and 1H NMR. MTT assay results showed that compounds 10a-10i displayed much stronger inhibitory effects than OA on the proliferation of four human tumor cell lines. The anti-proliferative activity of 10a-10e and 10i against human hepatoma HepG2 cell was comparable to that of the positive control 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester (CDDO-Me).

KW - Anticancer activity

KW - Furoxan

KW - NO donor

KW - Oleanolic acid

KW - α,β-unsaturated ketone

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M3 - Article

AN - SCOPUS:82455166781

SN - 1000-5048

VL - 42

SP - 385

EP - 391

JO - Journal of China Pharmaceutical University

JF - Journal of China Pharmaceutical University

IS - 5

ER -

Synthesis and anticancer activity of novel oleanolic acid derivatives

Abstract

Keywords

ASJC Scopus subject areas

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