Phytochemical Characterization of Xerospermum Noronhianum
Xerospermum noronhianum, locally known as gigi buntal (globe-fish’s teeth) or rambutan pachat (leech’s rambutan) is a species belonging to the Sapindaceae family. The Sapindaceae are generally well known as a prolific source of plant saponins. However, to date, there has been no systematic phytoc...
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my-upm-ir.71672013-05-27T07:33:49Z Phytochemical Characterization of Xerospermum Noronhianum 2008-12 Tan, Pei Jean Xerospermum noronhianum, locally known as gigi buntal (globe-fish’s teeth) or rambutan pachat (leech’s rambutan) is a species belonging to the Sapindaceae family. The Sapindaceae are generally well known as a prolific source of plant saponins. However, to date, there has been no systematic phytochemical and biological evaluation on this particular species. In the present study, several known compounds have been successfully isolated from various plant parts and solvent fractions of Xerospermum noronhianum. Three new triterpenoid saponins have been purified from the ethyl acetate and aqueous fractions of both stem and leaf of the plant. Through the use of high field NMR and mass spectroscopy, these saponins have been identified to be those of the oleanane-type, i.e 3-O-{α-L-rhamnopyranosyl(1→2)-β-D-fucopyranosyl}-28-O-{[α-Lrhamnopyranosyl( 1→2)][α-L-rhamnopyranosyl(1→6)]}-β-D-glucopyranosyl oleanolic acid, 3-O-{α-L-rhamnopyranosyl(1→3)-β-D-fucopyranosyl}-28-O-{α-Lrhamnopyranosyl( 1→4)}-β-D-glucopyranosyl oleanolic acid and 3-O-{α-Lrhamnopyranosyl( 1→2)-[3’,4’-diacetoxy-β-D-fucopyranosyl]}-28-O-{α-L rhamnopyranosyl(1→2)}-β-D-glucopyranosyl oleanolic acid. Several known compounds have also been isolated and identified as the free triterpenes namely lupeol, oleanolic acid, friedelin, 3β-hydroxy-29-nor-20-lupenone, 3β-hydroxy-lup-20(29)en-30-al, mixture of 3β-hydroxyolean-12-en-11-one and 3β-hydroxyurs-12-en-11-one; the flavonoid glycosides kampferol-3-O-rhamnoside, quercetin-3-O-rhamnoside; the benzoic acid derivatives 3,5-dihydroxy-4-methoxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid; as well as scopoletin, lupeol palmitate, and palmitic acid, mixture of β-sitosterol and stigmasterol and mixture of their glycosides. Oxidation of the major compound, lupeol, successfully yielded lupenone as the product. The crude extracts and isolated pure compounds were also further evaluated for their anti-cholinesterase activity, against two enzymes; acetylcholinesterase and butyrylcholinesterase, using thin layer chromatography bioautographic method. The inhibition activities of the test samples were expressed as pMIQ values, which represents the negative logarithm of the minimal inhibitory quantity (in moles) that produced the spot with the least observable whiteness. Generally, the crude extracts of stem, leaf and bark parts, all showed inhibition in the preliminary screening by giving white observable inhibition spots against a yellow-coloured background. The enzyme inhibiting constituents were, in part, found to be due to the triterpenoidal saponins, the free triterpenes as well as the sterol and its glycosides. However, the tested compounds were considered to be weakly active due to their low pMIQ values. Compounds with pMIQ values ≥ 10.5 is considered to be bioactive. All of the tested compounds in this study gave pMIQ value in the range of 1.7 to 3.7. Plant cells and tissues Plant biotechnology 2008-12 Thesis http://psasir.upm.edu.my/id/eprint/7167/ http://psasir.upm.edu.my/id/eprint/7167/1/IB_2008_9a.pdf application/pdf en public phd doctoral Universiti Putra Malaysia Plant cells and tissues Plant biotechnology Institute Bioscience English |
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Universiti Putra Malaysia |
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PSAS Institutional Repository |
| language |
English English |
| topic |
Plant cells and tissues Plant biotechnology |
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Plant cells and tissues Plant biotechnology Tan, Pei Jean Phytochemical Characterization of Xerospermum Noronhianum |
| description |
Xerospermum noronhianum, locally known as gigi buntal (globe-fish’s teeth) or
rambutan pachat (leech’s rambutan) is a species belonging to the Sapindaceae family.
The Sapindaceae are generally well known as a prolific source of plant saponins.
However, to date, there has been no systematic phytochemical and biological evaluation
on this particular species. In the present study, several known compounds have been
successfully isolated from various plant parts and solvent fractions of Xerospermum
noronhianum. Three new triterpenoid saponins have been purified from the ethyl acetate
and aqueous fractions of both stem and leaf of the plant. Through the use of high field
NMR and mass spectroscopy, these saponins have been identified to be those of the
oleanane-type, i.e 3-O-{α-L-rhamnopyranosyl(1→2)-β-D-fucopyranosyl}-28-O-{[α-Lrhamnopyranosyl(
1→2)][α-L-rhamnopyranosyl(1→6)]}-β-D-glucopyranosyl oleanolic
acid, 3-O-{α-L-rhamnopyranosyl(1→3)-β-D-fucopyranosyl}-28-O-{α-Lrhamnopyranosyl(
1→4)}-β-D-glucopyranosyl oleanolic acid and 3-O-{α-Lrhamnopyranosyl(
1→2)-[3’,4’-diacetoxy-β-D-fucopyranosyl]}-28-O-{α-L rhamnopyranosyl(1→2)}-β-D-glucopyranosyl oleanolic acid. Several known compounds
have also been isolated and identified as the free triterpenes namely lupeol, oleanolic
acid, friedelin, 3β-hydroxy-29-nor-20-lupenone, 3β-hydroxy-lup-20(29)en-30-al,
mixture of 3β-hydroxyolean-12-en-11-one and 3β-hydroxyurs-12-en-11-one; the
flavonoid glycosides kampferol-3-O-rhamnoside, quercetin-3-O-rhamnoside; the
benzoic acid derivatives 3,5-dihydroxy-4-methoxybenzoic acid, 3,4-dihydroxybenzoic
acid, 3,4,5-trihydroxybenzoic acid; as well as scopoletin, lupeol palmitate, and palmitic
acid, mixture of β-sitosterol and stigmasterol and mixture of their glycosides. Oxidation
of the major compound, lupeol, successfully yielded lupenone as the product.
The crude extracts and isolated pure compounds were also further evaluated for their
anti-cholinesterase activity, against two enzymes; acetylcholinesterase and
butyrylcholinesterase, using thin layer chromatography bioautographic method. The
inhibition activities of the test samples were expressed as pMIQ values, which represents
the negative logarithm of the minimal inhibitory quantity (in moles) that produced the
spot with the least observable whiteness. Generally, the crude extracts of stem, leaf and
bark parts, all showed inhibition in the preliminary screening by giving white observable
inhibition spots against a yellow-coloured background. The enzyme inhibiting
constituents were, in part, found to be due to the triterpenoidal saponins, the free
triterpenes as well as the sterol and its glycosides. However, the tested compounds were
considered to be weakly active due to their low pMIQ values. Compounds with pMIQ
values ≥ 10.5 is considered to be bioactive. All of the tested compounds in this study
gave pMIQ value in the range of 1.7 to 3.7. |
| format |
Thesis |
| qualification_name |
Doctor of Philosophy (PhD.) |
| qualification_level |
Doctorate |
| author |
Tan, Pei Jean |
| author_facet |
Tan, Pei Jean |
| author_sort |
Tan, Pei Jean |
| title |
Phytochemical Characterization of Xerospermum Noronhianum |
| title_short |
Phytochemical Characterization of Xerospermum Noronhianum |
| title_full |
Phytochemical Characterization of Xerospermum Noronhianum |
| title_fullStr |
Phytochemical Characterization of Xerospermum Noronhianum |
| title_full_unstemmed |
Phytochemical Characterization of Xerospermum Noronhianum |
| title_sort |
phytochemical characterization of xerospermum noronhianum |
| granting_institution |
Universiti Putra Malaysia |
| granting_department |
Institute Bioscience |
| publishDate |
2008 |
| url |
http://psasir.upm.edu.my/id/eprint/7167/1/IB_2008_9a.pdf |
| _version_ |
1747810666830364672 |