Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives

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 thei...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2011-11, Vol.21 (21), p.6245-6248
Main Authors: Lee, Eunyoung, Ahamed, V.S. Jamal, Kumar, Mahto Sanjeev, Rhee, Seog Woo, Moon, Surk-Sik, Hong, In Seok
Format: Article
Language:English
Subjects:
1,4- O-Diferuloylsecoisolariciresinol
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Biological and medical sciences
Cell Line, Tumor
chemistry
Cytotoxic lignans
Cytotoxicity
Drug Screening Assays, Antitumor
ferulic acid
General aspects
Hanultarin
Humans
Immunocytochemical analysis
Inhibitory Concentration 50
lignans
Lignans - chemical synthesis
Lignans - pharmacology
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Pharmacology. Drug treatments
seeds
Spectroscopy, Fourier Transform Infrared
Trichosanthes kirilowii
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 7.1–9.8 μM 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2011.09.014