• Archives of Pharmacal Research
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• 제9권4호
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• pp.237-242
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• 1986

The Synthesis of E, E, E-12-fluorofarnesol and E, Z-6-fluorofarnesol which are key intermediates for the study of biosynthesis of some sesquiterpenes, is described. E, E-Farnesyl acetate is treated with selenium dioxide to give E, E, E-12-hydroxy farnesyl acetate, whih is transformed by DAST into E, E, E-12-hydroxy farnesyl acetate, which is transformed by DAST into E, E, E,-12-fluorofarnesylacetate. The latter compound is hydrolyzed to E, E, E,-12-fluorofarnesol. The reformatsky reaction of 6-methyl-5-hepten-2-one with ethyl bromofluoroacetate affords ethyl 2-fluoro-3-hydroxy-3, 7 dimethyl-6-octanoate. This ester is acetylated and eliminated to give ethyl (Z)-2-fluoro-3, 7-dimethylocta-2, 6-dienoate, which is transformed to allyl bromide via allylic alcohol. The allyl bromide is treated with dianion of methyl acetate to give-keto ester. The $\beta$-keto ester is converted to diethyl phosphoryloxy compound. The conjugate addition of lithium dimethylcuprate to the latter compound gives fluoro ester, which is treated with DIBAL to afford E, Z-6-fluorofarnesol.

• 약학회지
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• 제41권4호
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• pp.421-432
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• 1997

A new lectin was partially purified from starfish,Asterina pectinifera by means of physiological saline extraction, salt fractionation, ion exchange chromatography and hy droxyapatite chromatography, and it was named APL. The biochemical properties of the APL were characterized. In addition, its effects on lymphocyte mitogenicity and cancer cell agglutinability were tested. The APL agglutinated nonspecifically human erythrocytes and rabbit blood cells. Agglutinability was decreased to 30% of control activity below pH 5 and above pH 9 and was relatively unstable at increasing temperatures above 60$^{\circ}C$. The activity was reduced by addition of two kinds of metal ions, $Ba^{2+},\;Mn^{2+}$ and chelating agent, EDTA. APL was proved to be glycoproteins containing 9% sugars. For carbohydrate specificity, it was found that the activity of APL was inhibited by D(+)-glucosamine, D(+)-galactosamine, stachyose, N-acetyl-galactosamine and methyl-${\alpha}$-D-galactopyranoside among 35 sugars tested. In amino acid composition, the contents of acidic amino acids such as aspartic acid and glutamic acid were relatively high. This result suggest that the isoelectric point would be in a lower range. APL was found that it promotes the division of human lymphocytes. APL was proved to be a potent agglutinin for cancer cells such as HeLa, L929 and L1210 cells. Significant changes on the HeLa cell surfaces affected by APL were observed under the electron microscope.