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Bioorg Med Chem Lett. 2011 Nov 1;21(21):6245-8. doi: 10.1016/j.bmcl.2011.09.014. Epub 2011 Sep 10.

Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives.

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1
Department of Chemistry, Kongju National University, 182 Shinkwandong, Gongju 314-701, Republic of Korea.

Abstract

One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8μM except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect.

PMID:
21958542
DOI:
10.1016/j.bmcl.2011.09.014
[Indexed for MEDLINE]
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