Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

Peng Wang; Jun Wang; Tian Tian Guo; Yingxia Li

doi:10.1016/j.carres.2010.01.002

Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

Peng Wang
, Jun Wang
, Tian Tian Guo
, Yingxia Li

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

25 Scopus citations

Abstract

Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by ¹H NMR and ¹³C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl β-d-GluNAc showed significant cytotoxicity against HL-60 and BGC-823.

Original language	English
Pages (from-to)	607-620
Number of pages	14
Journal	Carbohydrate Research
Volume	345
Issue number	5
DOIs	https://doi.org/10.1016/j.carres.2010.01.002
State	Published - 30 Mar 2010
Externally published	Yes

Keywords

Cytotoxic activity
N-Acetylglucosamine
Oleanolic acid
Saponin
Ursolic acid

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10.1016/j.carres.2010.01.002

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title = "Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins",

abstract = "Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by 1H NMR and 13C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl β-d-GluNAc showed significant cytotoxicity against HL-60 and BGC-823.",

keywords = "Cytotoxic activity, N-Acetylglucosamine, Oleanolic acid, Saponin, Ursolic acid",

author = "Peng Wang and Jun Wang and Guo, \{Tian Tian\} and Yingxia Li",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (No. 30701046 ). We would like to thank Dr. Jingrong Cui in State Key Laboratory of Natural and Biomimeti c Drugs for evaluating the antitumour activity of these syntheti c saponins. ",

year = "2010",

month = mar,

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doi = "10.1016/j.carres.2010.01.002",

language = "English",

volume = "345",

pages = "607--620",

journal = "Carbohydrate Research",

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T1 - Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

AU - Wang, Peng

AU - Wang, Jun

AU - Guo, Tian Tian

AU - Li, Yingxia

N1 - Funding Information: This work was supported by the National Natural Science Foundation of China (No. 30701046 ). We would like to thank Dr. Jingrong Cui in State Key Laboratory of Natural and Biomimeti c Drugs for evaluating the antitumour activity of these syntheti c saponins.

PY - 2010/3/30

Y1 - 2010/3/30

N2 - Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by 1H NMR and 13C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl β-d-GluNAc showed significant cytotoxicity against HL-60 and BGC-823.

AB - Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by 1H NMR and 13C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl β-d-GluNAc showed significant cytotoxicity against HL-60 and BGC-823.

KW - Cytotoxic activity

KW - N-Acetylglucosamine

KW - Oleanolic acid

KW - Saponin

KW - Ursolic acid

UR - https://www.scopus.com/pages/publications/77649179061

U2 - 10.1016/j.carres.2010.01.002

DO - 10.1016/j.carres.2010.01.002

M3 - Article

C2 - 20116049

AN - SCOPUS:77649179061

SN - 0008-6215

VL - 345

SP - 607

EP - 620

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 5

ER -

Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

Abstract

Keywords

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