Sphingolipids and Glycerolipids. IV. Syntheses and Ionophoretic Activities of Several Analogues of Soya-cerebroside II, a Calcium Ionophoretic Sphingoglycolipid Isolated from Soybean
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概要
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For examination of the structure-activity relationship five analogues [(2'R)-2'-hydroxypalmitoyl (3), palmitoyl (4), (2'S)-2'-hydroxypalmitoyl (5), β-D-galactosyl (6), and 8,9-dihydro (7) relevancies] of soya-cerebroside II (2), which is a calcium ionophoretic sphingoglycolipid isolated from soybean, have been synthesized by using our previously reported synthetic method for sphingoglycolipids. Examinations by using a W-08 (liquid-membrane type) apparatus and by means of the human erythrocyte membrane method, have shown that the (2'R)-2'-hydroxypalmitoyl analogue (3) exhibits higher ion-binding and ion-permeation activities for calcium ion than soya-cerebroside II (2), which contains 3 as the major component. It has also been found that the other analogues(5,6,7,8) do not show those ionophoretic activities.An enantiomer (8) of the (2'R)-2'-hydroxypalmitoyl analogue (3) has been synthesized and its calcium ionophoretic activity examined. Compound 8 exhibits calcium ion-binding activity equal to that of 3,but 8 lacks the ability to support calcium ion-permeation through human erythrocyte membrane. Thus, human erythrocyte membrane precisely distinguishes the absolute configurations of 3 and 8 as regards calcium ionophoretic activity.
- 公益社団法人日本薬学会の論文
- 1993-09-15
著者
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北川 勲
Faculty of Pharmaceutical Sciences, Osaka University
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渋谷 博孝
Faculty of Pharmaceutical Sciences, Osaka University
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北川 勲
Faculty Of Pharmaceutical Sciences Osaka University
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黒須 三千夫
Faculty of Pharmaceutical Sciences, Osaka University
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黒須 三千夫
阪大薬
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皆川 和之
Faculty of Pharmaceutical Sciences, Osaka University
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皆川 和之
大阪大学薬学部
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片山 精司
大阪大学薬学部
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片山 精司
Faculty of Pharmaceutical Sciences, Osaka University
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黒須 三千夫
Faculty Of Pharmaceutical Sciences Osaka University
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