Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.

Phytochemical studies of Artocarpus lowii King, A. scortechinii King and A. teysmanii Miq. have resulted in the isolation of four new compounds and eight known compounds. Three new compounds have been successfully isolated from A. lowii King, i.e 2',4'-dihydroxy-4-methoxy-3'-prenyldih...

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Main Author:	Jamil, Shajarahtunnur
Format:	Thesis
Language:	English
Published:	2006
Subjects:	QK Botany QD Chemistry
Online Access:	http://eprints.utm.my/id/eprint/112/1/ShajarahtunnurJamilPFS2006.pdf
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id	my-utm-ep.112
record_format	uketd_dc
spelling	my-utm-ep.1122020-02-04T08:04:38Z Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ. 2006-05-03 Jamil, Shajarahtunnur QK Botany QD Chemistry Phytochemical studies of Artocarpus lowii King, A. scortechinii King and A. teysmanii Miq. have resulted in the isolation of four new compounds and eight known compounds. Three new compounds have been successfully isolated from A. lowii King, i.e 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone, 2',3,4',4-tetrahydroxy-3'- prenylchalcone and 2-hydroxyparatocarpin C. Three known compounds were identified as cycloheterophyllin, 2',4',4-trihydroxy-3'-prenylchalcone and 4-hydroxylonchocarpin. Methylation of 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone and 2',4',4- trihydroxy-3'-prenylchalcone gave 2',4',4-trimethoxy-3'-prenyldihydrochalcone and 2'-hydroxy-4',4-dimethoxy-3'-prenylchalcone, respectively while methylation of cycloheterophyllin gave mixtures of dimethoxy and trimethoxy derivatives. Acetylation of cycloheterophyllin afforded cycloheterophyllin diacetate. A new compound was isolated from A. scortechinii King and was identified as 2',4',5',5-tetrahydroxy-3-geranyl-7,8-(2,2-dimethyl-6H-pyrano)-6-prenylflavone together with three known compounds, i.e artonin E, artobiloxanthone and lupeol 3-acetate. Methylation of artonin E gave artonin E trimethyl ether while acetylation of artonin E afforded artonin E tetraacetate. Four known compounds were isolated from A. teysmanii Miq., which were identified as artonin E, artobiloxanthone, artonol B and cycloartobiloxanthone. The structures of all compounds were established based on spectral studies using nuclear magnetic resonance spectroscopy, mass spectrometry, infrared spectroscopy and ultraviolet spectroscopy. The biological studies on the crude extracts and pure compounds of these three species showed that several pure compounds have significant biological activity especially in the antioxidant, platelet aggregation and cytotoxicity assays. Cycloheterophyllin and artonin E showed high ability to act as free radical scavengers with scavenging concentration values of 51.6 ug/mL and 48.3 ug/mL, respectively. Cycloheterophyllin, artonin E, isobavachalcone and 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone totally inhibited adenosine diphosphate-induced platelet aggregation compared to standard aspirin which suppressed only 31.6% of the platelet aggregation. Cyloheterophyllin and artonin E were found to be active against breast cancer cell line, MCF7 comparable to the standard tamoxifen citrate. Finally, 2'- hydroxy-4,4',6'-trimethoxy-3'-prenylchalcone was synthesized through a three step synthesis. The steps involved Friedel-Crafts prenylation followed by methylation and Claisen-Schmidt condensation. Oxidative cyclization of this chalcone yielded an aldehyde-type chalcone derivative. 2'-Hydroxy-4-methoxy-4'-O-prenylchalcone was synthesized through a two steps synthesis involving Friedel-Crafts prenylation followed by Claisen-Schmidt condensation. Attempted Claisen rearrangement produced 4'-hydroxy-4-methoxy-2'-O-prenylchalcone as the major product. 2006-05 Thesis http://eprints.utm.my/id/eprint/112/ http://eprints.utm.my/id/eprint/112/1/ShajarahtunnurJamilPFS2006.pdf application/pdf en public phd doctoral Universiti Teknologi Malaysia, Faculty of Science Faculty of Science
institution	Universiti Teknologi Malaysia
collection	UTM Institutional Repository
language	English
topic	QK Botany QD Chemistry
spellingShingle	QK Botany QD Chemistry Jamil, Shajarahtunnur Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.
description	Phytochemical studies of Artocarpus lowii King, A. scortechinii King and A. teysmanii Miq. have resulted in the isolation of four new compounds and eight known compounds. Three new compounds have been successfully isolated from A. lowii King, i.e 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone, 2',3,4',4-tetrahydroxy-3'- prenylchalcone and 2-hydroxyparatocarpin C. Three known compounds were identified as cycloheterophyllin, 2',4',4-trihydroxy-3'-prenylchalcone and 4-hydroxylonchocarpin. Methylation of 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone and 2',4',4- trihydroxy-3'-prenylchalcone gave 2',4',4-trimethoxy-3'-prenyldihydrochalcone and 2'-hydroxy-4',4-dimethoxy-3'-prenylchalcone, respectively while methylation of cycloheterophyllin gave mixtures of dimethoxy and trimethoxy derivatives. Acetylation of cycloheterophyllin afforded cycloheterophyllin diacetate. A new compound was isolated from A. scortechinii King and was identified as 2',4',5',5-tetrahydroxy-3-geranyl-7,8-(2,2-dimethyl-6H-pyrano)-6-prenylflavone together with three known compounds, i.e artonin E, artobiloxanthone and lupeol 3-acetate. Methylation of artonin E gave artonin E trimethyl ether while acetylation of artonin E afforded artonin E tetraacetate. Four known compounds were isolated from A. teysmanii Miq., which were identified as artonin E, artobiloxanthone, artonol B and cycloartobiloxanthone. The structures of all compounds were established based on spectral studies using nuclear magnetic resonance spectroscopy, mass spectrometry, infrared spectroscopy and ultraviolet spectroscopy. The biological studies on the crude extracts and pure compounds of these three species showed that several pure compounds have significant biological activity especially in the antioxidant, platelet aggregation and cytotoxicity assays. Cycloheterophyllin and artonin E showed high ability to act as free radical scavengers with scavenging concentration values of 51.6 ug/mL and 48.3 ug/mL, respectively. Cycloheterophyllin, artonin E, isobavachalcone and 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone totally inhibited adenosine diphosphate-induced platelet aggregation compared to standard aspirin which suppressed only 31.6% of the platelet aggregation. Cyloheterophyllin and artonin E were found to be active against breast cancer cell line, MCF7 comparable to the standard tamoxifen citrate. Finally, 2'- hydroxy-4,4',6'-trimethoxy-3'-prenylchalcone was synthesized through a three step synthesis. The steps involved Friedel-Crafts prenylation followed by methylation and Claisen-Schmidt condensation. Oxidative cyclization of this chalcone yielded an aldehyde-type chalcone derivative. 2'-Hydroxy-4-methoxy-4'-O-prenylchalcone was synthesized through a two steps synthesis involving Friedel-Crafts prenylation followed by Claisen-Schmidt condensation. Attempted Claisen rearrangement produced 4'-hydroxy-4-methoxy-2'-O-prenylchalcone as the major product.
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Jamil, Shajarahtunnur
author_facet	Jamil, Shajarahtunnur
author_sort	Jamil, Shajarahtunnur
title	Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.
title_short	Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.
title_full	Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.
title_fullStr	Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.
title_full_unstemmed	Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.
title_sort	phytochemical and bioactivities of malaysian artocarpus lowii king, a. scortechinii king and a. teysmanii miq.
granting_institution	Universiti Teknologi Malaysia, Faculty of Science
granting_department	Faculty of Science
publishDate	2006
url	http://eprints.utm.my/id/eprint/112/1/ShajarahtunnurJamilPFS2006.pdf
_version_	1747814345973170176

Phytochemical and bioactivities of Malaysian Artocarpus lowii king, A. Scortechinii king and A. Teysmanii MIQ.

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