Phytochemical Study On The Rhizomes Of Smilax Myosotiflora A. Dc. And Synthesis Of New Aurone Derivatives With Their Cytotoxic Activity
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Date
2015-09
Authors
ELHADI, ABOUBAKER ABDULNABI
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Abstract
Smilax myosotiflora, a climbing shrub belongs to Smeaealacace family. It is commonly known as Ubi Jaga in Malaysia, which has been long used in traditional food and medicine. In this study, the roots and rhizomes of this plant were extracted with different polarity of solvents; n-hexane, dichloromethane and methanol, using a Soxhlet apparatus. The methanol extract was partitioned with ethyl acetate then n-butanol. A successive column chromatography on these extracts afforded 10 isolated compounds from the roots and rhizomes of Smilax myosotiflora. Two triterpenoid glycosides, which were isolated from dichloromethane extract. p-Coumaric acid, two phenylpropanoid glycerides, two stilbenoids and three aurones, including one a new aurone were isolated from ethyl acetate extract. The structural modification study of the new isolated aurone compound was carried out to synthesize 14 new halo aurones in order to improve their biological activity. The isolated and synthesized compounds were fully characterized using the spectroscopic techniques including infrared, ultra violet, nuclear magnetic resonance and mass spectrometry, as well as crystallographic analysis. Total phenolic and total flavonoid contents were estimated for the extracts and further assayed for their antioxidant and anticancer activities. The results showed that the ethyl acetate extract has the highest phenolic and flavonoids contents. In addition, the antioxidant and cytotoxic activities of the isolated and synthesized compounds were also evaluated. Generally, the extracts and isolated compounds displayed a moderate to weak anti-proliferative effect, against human colon cancer (HCT 116), human breast cancer (MCF-7) and blood cancer (K 562),
except resveratrol which showed significant activity against MCF-7 tumor cells. In the present study, it was deduced that natural aurones isolated from S. myosotiflora (rhizomes) showed mild antiproliferative activity. In fact, the structure modification of natural aurone compound by addition of halogen atoms on both benzene ring-A and ring-B of aurone derivatives showed a promising anticancer activity, especially compounds 5,7,2'-trichloroaurone and 5,7-dichloro-4'-methylaurone as compared to standard drugs against three cell lines under investigation.
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Phytochemical Study On The Rhizomes Of Smilax Myosotiflora A. Dc , And Synthesis Of New Aurone Derivatives With Their Cytotoxic Activity