@conference{
author = "Samardžić, Stevan and Maksimović, Zoran and Đorđić, Marija and Stanojković, Tatjana and Petković, Miloš",
year = "2021",
abstract = "INTRODUCTION:
False indigo-bush (Amorpha fruticosa L., Fabaceae) is an invasive shrub native to central and eastern North America. In Serbia,
it can be found along roads, railways, and riverbeds, where it spreads easily. Previous studies have shown that A. fruticosa
contains several classes of secondary metabolites (e.g. rotenoids, isoflavonoids, prenylflavanones, chalcones, and stilbe-
noids) and exhibits various biological activities (e.g. antioxidant, anti-inflammatory, antidiabetic, insecticidal).
OBJECTIVES:
This study aimed to examine the in vitro cytotoxic activity of prenylated phenolic constituents of false indigo-bush.
METHOD / DESIGN:
An aliquot (0.82 g) of ethanol-soluble part of n-hexane fruit extract (1:10, m/V) was loaded onto silica gel column (3 × 43 cm)
and eluted with mixtures of n-hexane and ethyl acetate (100:0 _ 0:100, V/V). 96 Fractions were collected, analyzed by silica
gel TLC and combined based on chemical composition similarity. Compound 1 (6.9 mg) precipitated as the white powder
during solvent removal from the united fractions 59–69. The pooled fractions 89–92 (80.6 mg) and 95–96 (59.6 mg) gave
compounds 2 (29.8 mg, Rf = 0.5) and 3 (5.8 mg, Rf = 0.53), respectively, after separation by preparative silica gel TLC in a
solvent system consisting of n-hexane, ethyl acetate and formic acid (80:20:1, V/V/V). The structure determination of the iso-
lated prenylated phenols were based on their UV, MS, and 1
H and 13
C NMR spectra. MTT assay was employed to assess their
cytotoxicity against human tumor cell lines (HeLa, HT-29
, HCT-116
, LS174) derived from the cervix adenocarcinoma and colorec-
tal carcinomas, as well as human fetal lung fibroblasts (MRC-5). cis-Diamminedichloroplatinum (CDDP) was used as a control
substance. The activity is expressed as the IC 50 value, i.e. the concentration of the tested substance that led to 50% inhibition
of survival, compared to the vehicle-treated control group. The statistical analysis was performed using the Student’s t-test.
RESULTS:
Based on a comparison of recorded spectral data and literature data, compound 1 was identified as 5,7-dihydroxy-8-gera-
nylflavanone, compound 2 as 2-carboxy-3,5-dihydroxy-4-geranylbibenzyl, and compound 3 as 2-carboxy-3-hydroxy-4-pre-
nyl-5-metoxybibenzyl (amorfrutin A). All tested constituents showed cytotoxicity with the IC50 values in the range 10.55–
166.11 μg/mL. The non-selectivity of compounds 2 and 3 could be observed. On the other hand, compound 1 was selective
and exhibited pronounced activity against the HeLa cell line (IC 50 = 10.55 μg/mL). HT-29 (IC 50 = 122.28 μg/mL) and HCT-116
(IC 50 = 147.09 μg/mL) cancer cell lines, as well as normal cell line MRC-5 (IC50 = 166.11 μg/mL), were less susceptible to the action of compound 1, whereas the survival of LS174 cell line was not affected at all by compound 1 in the tested concen-
tration range. The effectiveness of the control substance CDDP in reducing the survival of the HeLa cancer cell line was the
highest (IC50 = 5.20 μg/mL). It should be emphasized that CDDP, among tested substances, was also the most toxic against
the MRC-5 cell line (IC 50 = 8.28 μg/mL). IC 50 values ranges of compounds 2 and 3 were 31.97–56.29 μg/mL and 35.67–53.21
μg/mL, respectively.
CONCLUSIONS:
5,7-Dihydroxy-8-geranylflavanone, the constituent of false indigo-bush fruit, exhibited strong and selective activity against
the human cervix adenocarcinoma cell line in the MTT assay, therefore, its cytotoxic potential can be considered significant.
Further studies are needed to fully assess the demonstrated effect.",
publisher = "University Prince of Songkla, Thailand, University of Novi Sad, Faculty of Sciences, Serbia, Novi Sad",
journal = "The International Bioscience Conference and the 8th International PSU – UNS Bioscience Conference - IBSC2021 Book of Abstracts",
title = "Cytotoxic prenylated phenols of false indigo-bush (Amorpha fruticosa L.)",
pages = "126-127",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5104"
}
