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Bio-guided isolation of the cytotoxic terpenoids from the roots of Euphorbia kansui against human normal cell lines L-O2 and GES-1.

Zhang L, Gao L, Li Z, Yan X, Yang Y, Tang Y, Cao Y, Ding A - Int J Mol Sci (2012)

Bottom Line: The 95% ethanol extract showed a significant inhibition of cell proliferation against human normal cell lines L-O2 and GES-1.Bioassay-guided separation of the 95% ethanol extract from the roots of E. kansui led to the isolation of 12 diverse terpenoids whose structures were identified by (1)H, (13)C NMR spectroscopy and ESI-MS as kansuinine A (1), kansuinine B (2), kansuinine C (3), kansuiphorin C (4), 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol (5), 3-O-(2'E,4'Edecadienoyl)-20-O-acetylingenol (6), 3-O-(2'E,4'Z-decadienoyl)-20-deoxyingenol (7), 3-O-benzoyl-20-deoxyingenol (8), 5-O-benzoyl-20-deoxyingenol (9), kansenone (10), epi-kansenone (11), euphol (12).These results will be significantly helpful to reveal the mechanism of toxicity of kansui and to effectively guide safer clinical application of this herb.

View Article: PubMed Central - PubMed

Affiliation: Jiangsu Key Laboratory for High Technology Research of TCM Formulae, Nanjing University of Chinese Medicine, Nanjing 210046, China; E-Mails: zhangli@njutcm.edu.cn (L.Z.); gaolan1000@126.com (L.G.); lizhengjun404@126.com (Z.L.); yanxiaojing963@163.com (X.Y.); candy-jing@qq.com (Y.Y.); raindc@163.com (Y.C.).

ABSTRACT
The dried roots of Euphorbia kansui (kansui) have been used for centuries in China as a herbal medicine for edema, ascites, and asthma. The 95% ethanol extract showed a significant inhibition of cell proliferation against human normal cell lines L-O2 and GES-1. Bioassay-guided separation of the 95% ethanol extract from the roots of E. kansui led to the isolation of 12 diverse terpenoids whose structures were identified by (1)H, (13)C NMR spectroscopy and ESI-MS as kansuinine A (1), kansuinine B (2), kansuinine C (3), kansuiphorin C (4), 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol (5), 3-O-(2'E,4'Edecadienoyl)-20-O-acetylingenol (6), 3-O-(2'E,4'Z-decadienoyl)-20-deoxyingenol (7), 3-O-benzoyl-20-deoxyingenol (8), 5-O-benzoyl-20-deoxyingenol (9), kansenone (10), epi-kansenone (11), euphol (12). All these 12 terpernoids were evaluated in vitro for cytotoxicity on L-O2 and GES-1 cell lines. Most ingenane-type diterpenoids and 8-ene-7-one triterpenoids (5-11) exhibited a relatively lower IC(50) value; therefore, these compounds had stronger cytotoxicity against human normal cell lines L-O2 and GES-1 with dose-dependent relationships. These results will be significantly helpful to reveal the mechanism of toxicity of kansui and to effectively guide safer clinical application of this herb.

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The chemical structures of compounds 1–12.
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f1-ijms-13-11247: The chemical structures of compounds 1–12.

Mentions: On the basis of cytotoxicity assay results of different extracts and pure compounds against human normal cell lines L-O2 and GES-1 (Table 4), 12 terpenoids were isolated from the EtOAc extract of kansui. By spectral and physiochemical data analysis and/or comparison with literatures data, their structures were elucidated as kansuinines A, B, C (1–3) [17,21], kansuiphorin C (4) [20], 3-O-(2′E,4′Zdecadienoyl)-20-O-acetylingenol (5) [17], 3-O-(2′E,4′E-decadienoyl)-20-O-acetylingenol (6) [17], 3-O-(2′E,4′Z-decadienoyl)-20-deoxyingenol (7) [17,23], 3-O-benzoyl-20-deoxyingenol (8) [22], 5-O-benzoyl-20-deoxyingenol (9) [17], kansenone (10) [17], epi-kansenone (11) [17], and euphol (12) [17,21] (Figure 1). This was the first report of the bio-guided isolation of different fractions and pure terpenoids from kansui extracts by the gastrointestinal and hepatic cytotoxicity assay against human normal cell lines L-O2 and GES-1.


Bio-guided isolation of the cytotoxic terpenoids from the roots of Euphorbia kansui against human normal cell lines L-O2 and GES-1.

Zhang L, Gao L, Li Z, Yan X, Yang Y, Tang Y, Cao Y, Ding A - Int J Mol Sci (2012)

The chemical structures of compounds 1–12.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3472742&req=5

f1-ijms-13-11247: The chemical structures of compounds 1–12.
Mentions: On the basis of cytotoxicity assay results of different extracts and pure compounds against human normal cell lines L-O2 and GES-1 (Table 4), 12 terpenoids were isolated from the EtOAc extract of kansui. By spectral and physiochemical data analysis and/or comparison with literatures data, their structures were elucidated as kansuinines A, B, C (1–3) [17,21], kansuiphorin C (4) [20], 3-O-(2′E,4′Zdecadienoyl)-20-O-acetylingenol (5) [17], 3-O-(2′E,4′E-decadienoyl)-20-O-acetylingenol (6) [17], 3-O-(2′E,4′Z-decadienoyl)-20-deoxyingenol (7) [17,23], 3-O-benzoyl-20-deoxyingenol (8) [22], 5-O-benzoyl-20-deoxyingenol (9) [17], kansenone (10) [17], epi-kansenone (11) [17], and euphol (12) [17,21] (Figure 1). This was the first report of the bio-guided isolation of different fractions and pure terpenoids from kansui extracts by the gastrointestinal and hepatic cytotoxicity assay against human normal cell lines L-O2 and GES-1.

Bottom Line: The 95% ethanol extract showed a significant inhibition of cell proliferation against human normal cell lines L-O2 and GES-1.Bioassay-guided separation of the 95% ethanol extract from the roots of E. kansui led to the isolation of 12 diverse terpenoids whose structures were identified by (1)H, (13)C NMR spectroscopy and ESI-MS as kansuinine A (1), kansuinine B (2), kansuinine C (3), kansuiphorin C (4), 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol (5), 3-O-(2'E,4'Edecadienoyl)-20-O-acetylingenol (6), 3-O-(2'E,4'Z-decadienoyl)-20-deoxyingenol (7), 3-O-benzoyl-20-deoxyingenol (8), 5-O-benzoyl-20-deoxyingenol (9), kansenone (10), epi-kansenone (11), euphol (12).These results will be significantly helpful to reveal the mechanism of toxicity of kansui and to effectively guide safer clinical application of this herb.

View Article: PubMed Central - PubMed

Affiliation: Jiangsu Key Laboratory for High Technology Research of TCM Formulae, Nanjing University of Chinese Medicine, Nanjing 210046, China; E-Mails: zhangli@njutcm.edu.cn (L.Z.); gaolan1000@126.com (L.G.); lizhengjun404@126.com (Z.L.); yanxiaojing963@163.com (X.Y.); candy-jing@qq.com (Y.Y.); raindc@163.com (Y.C.).

ABSTRACT
The dried roots of Euphorbia kansui (kansui) have been used for centuries in China as a herbal medicine for edema, ascites, and asthma. The 95% ethanol extract showed a significant inhibition of cell proliferation against human normal cell lines L-O2 and GES-1. Bioassay-guided separation of the 95% ethanol extract from the roots of E. kansui led to the isolation of 12 diverse terpenoids whose structures were identified by (1)H, (13)C NMR spectroscopy and ESI-MS as kansuinine A (1), kansuinine B (2), kansuinine C (3), kansuiphorin C (4), 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol (5), 3-O-(2'E,4'Edecadienoyl)-20-O-acetylingenol (6), 3-O-(2'E,4'Z-decadienoyl)-20-deoxyingenol (7), 3-O-benzoyl-20-deoxyingenol (8), 5-O-benzoyl-20-deoxyingenol (9), kansenone (10), epi-kansenone (11), euphol (12). All these 12 terpernoids were evaluated in vitro for cytotoxicity on L-O2 and GES-1 cell lines. Most ingenane-type diterpenoids and 8-ene-7-one triterpenoids (5-11) exhibited a relatively lower IC(50) value; therefore, these compounds had stronger cytotoxicity against human normal cell lines L-O2 and GES-1 with dose-dependent relationships. These results will be significantly helpful to reveal the mechanism of toxicity of kansui and to effectively guide safer clinical application of this herb.

Show MeSH
Related in: MedlinePlus