Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali

In the present work, phytochemical study was conducted on M. triloba collected from Pasir Raja, Terengganu with the aim of isolating and identifying the flavonoids constituents from the flower of the plant. The phytochemical procedures adopted were vacuum liquid chromatography followed by column chr...

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Main Author:	Zakaria @ Ali, Ishak
Format:	Thesis
Language:	English
Published:	2011
Subjects:	Botanical chemistry Phytochemicals Medicinal plants (Culture only)
Online Access:	https://ir.uitm.edu.my/id/eprint/38015/1/38015.pdf
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spelling	my-uitm-ir.380152022-11-01T08:34:33Z Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali 2011 Zakaria @ Ali, Ishak Botanical chemistry. Phytochemicals Medicinal plants (Culture only) In the present work, phytochemical study was conducted on M. triloba collected from Pasir Raja, Terengganu with the aim of isolating and identifying the flavonoids constituents from the flower of the plant. The phytochemical procedures adopted were vacuum liquid chromatography followed by column chromatography, medium pressure liquid chromatography, radial chromatography and preparative thin layer chromatography. The structural elucidation was accomplished by spectroscopic methods such as 1D-NMR (!H, 13C, DEPT), 2D-NMR (COSY, HMQC, HMBC), UV, IR and MS and comparison with published data. Isolation and purification of the flower of M. triloba afforded seven compounds comprising of five flavonoids that are 6-prenyl-3'-methoxy-eriodictyol, nymphaeol-B, flavonoid DL 4, nymphaeol-C and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone and two coumarins that are 5,7- dihydroxycoumarin and scopoletin. Three flavonoids, 6-prenyl-3'-methoxyeriodictyol, flavonoid DL4 and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone were isolated for the first time from Macaranga genus. 6-Prenyl-3'-methoxy-eriodictyol, nymphaeol-B, nymphaeol-C and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone were tested for antioxidant, cytotoxic and antiplasmodial activity. The antioxidant activities were evaluated using the ferric thiocyanate (FTC) and thiobarbituric acid (TBA) method while the radical scavenging activity was measured by the 1,1- diphenylpicryl hydrazyl (DPPH). In FTC assay, the four flavonoids demonstrated high percent of inhibition with range of 98-100% while in TBA the percent of inhibition is slightly reduced to 81-92%. The DPPH test showed 6-farnesyl-3',4',5,7- tetrahydroxyflavanone had strong radical-scavenging activity with IC50 values of 12.2 (ig/ml followed by nymphaeol-B (13.5 ug/ml) and nymphaeol-C (16.5 ug/ml) while 6-prenyl-3'-methoxy-eriodictyol is a weak radical scavenger (155 fig/ml). The four flavonoids were also tested for cytotoxic activity against three cancer cell lines namely HeLa, HL60 and MCF-7. Three flavonoids showed significant cytotoxicity in the range 11.6 - 23.5 ug/ml. 6-Farnesyl-3',4',5,7-tetrahydroxyflavanone inhibited strongly the growth of HeLa, HL60 and MCF-7 cancer cell lines with IC50 values of 1.3 ug/ml, 3.3 ug/ml and 5.6 ug/ml respectively. Finally, for the antiplasmodial activity, 6-farnesyl-3',4',5,7-tetrahydroxyflavanone displayed the strongest inhibition activity with an IC50 value of 0.06 uM followed by nymphaeol-C and nymphaeol-B with the values of 2.04 uM and 4.02 uM. The results of these test indicated that 6- farnesyl-3',4',5,7-tetrahydoxyflavanone showed strong activities against antioxidant, cytotoxic and antiplasmodial suggesting the potential of this compound as cure for anticancer and antiplasmodial. 2011 Thesis https://ir.uitm.edu.my/id/eprint/38015/ https://ir.uitm.edu.my/id/eprint/38015/1/38015.pdf text en public masters Universiti Teknologi MARA (UiTM) Faculty of Applied Sciences Ahmat, Norizan
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Ahmat, Norizan
topic	Botanical chemistry Phytochemicals Medicinal plants (Culture only)
spellingShingle	Botanical chemistry Phytochemicals Medicinal plants (Culture only) Zakaria @ Ali, Ishak Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali
description	In the present work, phytochemical study was conducted on M. triloba collected from Pasir Raja, Terengganu with the aim of isolating and identifying the flavonoids constituents from the flower of the plant. The phytochemical procedures adopted were vacuum liquid chromatography followed by column chromatography, medium pressure liquid chromatography, radial chromatography and preparative thin layer chromatography. The structural elucidation was accomplished by spectroscopic methods such as 1D-NMR (!H, 13C, DEPT), 2D-NMR (COSY, HMQC, HMBC), UV, IR and MS and comparison with published data. Isolation and purification of the flower of M. triloba afforded seven compounds comprising of five flavonoids that are 6-prenyl-3'-methoxy-eriodictyol, nymphaeol-B, flavonoid DL 4, nymphaeol-C and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone and two coumarins that are 5,7- dihydroxycoumarin and scopoletin. Three flavonoids, 6-prenyl-3'-methoxyeriodictyol, flavonoid DL4 and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone were isolated for the first time from Macaranga genus. 6-Prenyl-3'-methoxy-eriodictyol, nymphaeol-B, nymphaeol-C and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone were tested for antioxidant, cytotoxic and antiplasmodial activity. The antioxidant activities were evaluated using the ferric thiocyanate (FTC) and thiobarbituric acid (TBA) method while the radical scavenging activity was measured by the 1,1- diphenylpicryl hydrazyl (DPPH). In FTC assay, the four flavonoids demonstrated high percent of inhibition with range of 98-100% while in TBA the percent of inhibition is slightly reduced to 81-92%. The DPPH test showed 6-farnesyl-3',4',5,7- tetrahydroxyflavanone had strong radical-scavenging activity with IC50 values of 12.2 (ig/ml followed by nymphaeol-B (13.5 ug/ml) and nymphaeol-C (16.5 ug/ml) while 6-prenyl-3'-methoxy-eriodictyol is a weak radical scavenger (155 fig/ml). The four flavonoids were also tested for cytotoxic activity against three cancer cell lines namely HeLa, HL60 and MCF-7. Three flavonoids showed significant cytotoxicity in the range 11.6 - 23.5 ug/ml. 6-Farnesyl-3',4',5,7-tetrahydroxyflavanone inhibited strongly the growth of HeLa, HL60 and MCF-7 cancer cell lines with IC50 values of 1.3 ug/ml, 3.3 ug/ml and 5.6 ug/ml respectively. Finally, for the antiplasmodial activity, 6-farnesyl-3',4',5,7-tetrahydroxyflavanone displayed the strongest inhibition activity with an IC50 value of 0.06 uM followed by nymphaeol-C and nymphaeol-B with the values of 2.04 uM and 4.02 uM. The results of these test indicated that 6- farnesyl-3',4',5,7-tetrahydoxyflavanone showed strong activities against antioxidant, cytotoxic and antiplasmodial suggesting the potential of this compound as cure for anticancer and antiplasmodial.
format	Thesis
qualification_level	Master's degree
author	Zakaria @ Ali, Ishak
author_facet	Zakaria @ Ali, Ishak
author_sort	Zakaria @ Ali, Ishak
title	Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali
title_short	Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali
title_full	Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali
title_fullStr	Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali
title_full_unstemmed	Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali
title_sort	chemical constituents from the flower of macaranga triloba / ishak zakaria @ ali
granting_institution	Universiti Teknologi MARA (UiTM)
granting_department	Faculty of Applied Sciences
publishDate	2011
url	https://ir.uitm.edu.my/id/eprint/38015/1/38015.pdf
_version_	1783734449165303808

Chemical constituents from the flower of Macaranga triloba / Ishak Zakaria @ Ali

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