Phytochemical analysis of Aglaia macrophylla

The Meliaceae family, comprising of about 1400 species, is an important source of limonoids and tetranortriterpenoids. Aglaia is one of the genus within the family which has been the focus of phytochemical investigations due to its interesting biological activities. Certain species of Aglaia have tr...

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Main Author:	Yusof, Khairul Nazri
Format:	Thesis
Language:	English
Published:	2013
Subjects:	Meliaceae Botanical chemistry
Online Access:	http://psasir.upm.edu.my/id/eprint/67619/1/IB%202013%2029%20IR.pdf
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spelling	my-upm-ir.676192019-03-15T07:39:41Z Phytochemical analysis of Aglaia macrophylla 2013-10 Yusof, Khairul Nazri The Meliaceae family, comprising of about 1400 species, is an important source of limonoids and tetranortriterpenoids. Aglaia is one of the genus within the family which has been the focus of phytochemical investigations due to its interesting biological activities. Certain species of Aglaia have traditionally been used for their medicinal and healing properties, such as for the treatment of fever, diarrhoea, inflammation and wounds. Although there has been many previous investigations on the genus, thus far, the species A. macrophylla has not been put through any phytochemical investigation. This species is a common species in Peninsular Malaysia. This work describes the phytochemical investigation on the methanolic bark extract of Aglaia macrophylla, leading to the isolation and identification of three new apotirucallane triterpenoids in addition to a known seco-limonoid. All compounds were identified by a combination of spectroscopic methods including UV, IR, 1D and 2D NMR and ESI-MS as well as comparison with literature data. The air-ground barks of Aglaia macrophylla were cold extracted by macerating in MeOH for several hours and repetitive cycles. The concentrated methanolic extract was partitioned into hexane, ethyl acetate and aqueous fractions. The hexane and ethyl acetate fractions were subjected to various chromatographic procedures which included vacuum liquid chromatography (VLC), column chromatography (CC) and finally, repetitive semi-preparative High Performance Liquid Chromatography (HPLC). The bark extract yielded four triterpenoids, one of which is a known seco-protolimonoid with a hemiacetal C-17 side chain, identified as methyl-1,7-diacetoxy-23,24,25-trihydroxy-20,21,24-epoxy-3,4-seco-apotirucall-4(28),14(15)-diene-3-oate (56). The compound is a constituent of another Meliaceae species, Trichilia elegans. The other three compounds (57, 58 and 59) are new, all possessing the same 3-oxoapotirucallane skeleton and carrying highly oxygenated C-17 side chains. The compounds were identified as 3,5,6-trihydroxy-6-methyl-2-(4,4,8,10,13-pentamethyl-3-oxo-1H-cyclopenta[a]phenanthren-17-yl) heptanoic acid (57), 4,4,8,10,13-pentamethyl-17-(23,24,25-trihydroxy-20,21,24-epoxy)-2H-cyclopenta[a]phenanthren-3-one (58) and 4,4,8,10,13-pentamethyl-17-(3,5,6-trihydroxy-6-methylheptan-2-yl)-2H-cyclopenta[a]phenanthren-3-one (59). Compound 58 was obtained from the hexane soluble fraction of the methanolic extract. The side chain was similar to the known 56 except for the loss of the hydroxyl group on C-24. Meanwhile, compounds 57 and 59 were isolated from the ethyl acetate soluble fraction. Compound 59 appears to be the C-21 oxidation product of 57. Meliaceae Botanical chemistry 2013-10 Thesis http://psasir.upm.edu.my/id/eprint/67619/ http://psasir.upm.edu.my/id/eprint/67619/1/IB%202013%2029%20IR.pdf text en public masters Universiti Putra Malaysia Meliaceae Botanical chemistry
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English
topic	Meliaceae Botanical chemistry
spellingShingle	Meliaceae Botanical chemistry Yusof, Khairul Nazri Phytochemical analysis of Aglaia macrophylla
description	The Meliaceae family, comprising of about 1400 species, is an important source of limonoids and tetranortriterpenoids. Aglaia is one of the genus within the family which has been the focus of phytochemical investigations due to its interesting biological activities. Certain species of Aglaia have traditionally been used for their medicinal and healing properties, such as for the treatment of fever, diarrhoea, inflammation and wounds. Although there has been many previous investigations on the genus, thus far, the species A. macrophylla has not been put through any phytochemical investigation. This species is a common species in Peninsular Malaysia. This work describes the phytochemical investigation on the methanolic bark extract of Aglaia macrophylla, leading to the isolation and identification of three new apotirucallane triterpenoids in addition to a known seco-limonoid. All compounds were identified by a combination of spectroscopic methods including UV, IR, 1D and 2D NMR and ESI-MS as well as comparison with literature data. The air-ground barks of Aglaia macrophylla were cold extracted by macerating in MeOH for several hours and repetitive cycles. The concentrated methanolic extract was partitioned into hexane, ethyl acetate and aqueous fractions. The hexane and ethyl acetate fractions were subjected to various chromatographic procedures which included vacuum liquid chromatography (VLC), column chromatography (CC) and finally, repetitive semi-preparative High Performance Liquid Chromatography (HPLC). The bark extract yielded four triterpenoids, one of which is a known seco-protolimonoid with a hemiacetal C-17 side chain, identified as methyl-1,7-diacetoxy-23,24,25-trihydroxy-20,21,24-epoxy-3,4-seco-apotirucall-4(28),14(15)-diene-3-oate (56). The compound is a constituent of another Meliaceae species, Trichilia elegans. The other three compounds (57, 58 and 59) are new, all possessing the same 3-oxoapotirucallane skeleton and carrying highly oxygenated C-17 side chains. The compounds were identified as 3,5,6-trihydroxy-6-methyl-2-(4,4,8,10,13-pentamethyl-3-oxo-1H-cyclopenta[a]phenanthren-17-yl) heptanoic acid (57), 4,4,8,10,13-pentamethyl-17-(23,24,25-trihydroxy-20,21,24-epoxy)-2H-cyclopenta[a]phenanthren-3-one (58) and 4,4,8,10,13-pentamethyl-17-(3,5,6-trihydroxy-6-methylheptan-2-yl)-2H-cyclopenta[a]phenanthren-3-one (59). Compound 58 was obtained from the hexane soluble fraction of the methanolic extract. The side chain was similar to the known 56 except for the loss of the hydroxyl group on C-24. Meanwhile, compounds 57 and 59 were isolated from the ethyl acetate soluble fraction. Compound 59 appears to be the C-21 oxidation product of 57.
format	Thesis
qualification_level	Master's degree
author	Yusof, Khairul Nazri
author_facet	Yusof, Khairul Nazri
author_sort	Yusof, Khairul Nazri
title	Phytochemical analysis of Aglaia macrophylla
title_short	Phytochemical analysis of Aglaia macrophylla
title_full	Phytochemical analysis of Aglaia macrophylla
title_fullStr	Phytochemical analysis of Aglaia macrophylla
title_full_unstemmed	Phytochemical analysis of Aglaia macrophylla
title_sort	phytochemical analysis of aglaia macrophylla
granting_institution	Universiti Putra Malaysia
publishDate	2013
url	http://psasir.upm.edu.my/id/eprint/67619/1/IB%202013%2029%20IR.pdf
_version_	1747812490164568064

Phytochemical analysis of Aglaia macrophylla

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