Composition comprising caffeoylshikimic acids, protocatechuic acid, hydroxytyrosol, hydroxybenzoic acid and their derivatives and method of preparation thereof
a technology of hydroxytyrosol and tamiflu, which is applied in the separation/purification of carboxylic acid esters, plant/algae/fungi/lichens ingredients, organic chemistry, etc., can solve the problems of hampered production of tamiflu
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example 1
Isolation and Pretreatment
[0032]Extract from oil palm, vegetation liquor from palm oil milling and palm oil mill effluent was prepared based on a filtration procedure.
Pre-Concentration Treatment
[0033]The sample was pre-concentrated with Sample Prep using “Sep pak” cartridges for solvent exchange. The selected chromatography used to concentrate the sample was preparative high performance liquid chromatography (HPLC).
[0034]The solvent exchange was carried out based on the following steps:[0035]a) Conditioning—involving the flushing the unused separation pack (C18) with methanol and subsequently with water.[0036]b) Sample Injection—involving injecting an amount of 2 ml of sample into the separation pack and then forced out with a suitable syringe,[0037]c) Washing—involving injecting 1 ml of water through the pack to remove any form of impurities from the sample.[0038]d) Eluting—involving injecting 2 ml of methanol through the separation pack so as to elute the remaining sample which ha...
example 2
Chemical Structure of Peaks
[0043]The molecular weights of the three peaks obtained can be obtained using MALDI Mass Spectra analysis. An amount of 1 μl of the sample was directly deposited onto the sample holder to determine (M-H). Results obtained from this analysis are shown in FIG. 3.
[0044]The UV spectrums of peaks 6, 7 and 8 were taken and it is found that the UV spectrums for all these compounds were similar, as suitably shown in FIG. 4.
NMR Analysis
[0045]The chemical structure of the compound based on these peaks was analysed using NMR analysis. Results obtained indicate that each molecule from peaks 6, 7 and 8 has 16 carbons with two carbonyls (ester or carboxyl) ten sp2 carbons whereby one aromatic ring with another two double bonds, three oxygenated methine carbons and a methylene carbon. It is further observed that the aliphatic protons in the molecule are in two spin systems. The chemical shifts of the carbons and the associated protons thereby indicate the structure of ca...
example 3
Profiling—Reverse Phase HPLC
[0048]As shown in FIG. 8, the sample contains at least one of the following compounds, hydroxytyrosol, protocatechuic acid, p-hydroxybenzoic acid, 5-0-caffeoylshikimic acid, 4-0-caffeoylshikimic acid and 3-0-caffeoylshikimic acid.
[0049]In order to carry out further HPLC analysis on the compounds, the sample was prepared as follows:[0050]a) Preparing 10 mg of alpha-cyano-4-hydroxycinnamic acid, 99% was added to 1 ml of ethanol;[0051]b) The internal standard solution (20 μl) was added to 980 μl of the sample; and[0052]c) 300 μl of this mixture was used for HPLC analysis.
[0053]A reverse phase HPLC was conducted based on the above conditions whereby an Exsil ODS 5 μm SGE column (250×4.6) was used with a flow rate of 0-8 ml / min and a photodiode detection of 280 nm. The injection volume was 20 μl. The mobile phase gradient for this analysis is shown below in TABLE 2 below:
Solvent B (10%Time (minutes)Solvent A (0.1% HOAC)water / ACN V / V)010001095545703050010055010...
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