9 カルモジュリン依存性ホスホジエステラーゼ阻害物質KS-501およびKS-502の構造決定(ポスター発表の部)

概要

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Two new phenolic glycosides, named KS-501(1) and KS-502(2), are inhibitors of calmoduline-dependent cyclic nucleotide phosphodiesterase (IC_<50>=0.99μg/ml and 2.8μg/ml, respectively) isolated from the culture broth of Sporothrix sp. The physico-chemical properties of 1 and 2 are summarized in Table 1. The ^1H and ^<13>C NMR spectra of 1 showed the presence of tri- and tetra-substituted benzene rings, two n-heptyl side chains, two hydoxy groups, one ester carbonyl group and one furanose-type sugar moiety (Table 2). Additional one carboxy group was present on the aromatic ring of 2. Methanolysis of 1 furnished an aglycone (3) and methyl D-galactopyranoside (4). Further methanolysis of 3 provided 3-heptyl resolcinol (6) and methyl 2,4-dihydroxy-6-heptyl benzoate (7), confirming the structure of 3. The location of the sugar moiety in 1 was determined to be at C-2' by the LSPD experiment of 1(Fig. 2) and the NOE experiment of methylate (8) (Fig. 3). The structure of 2 is different from that of 1 with respect to the aglycone moiety. The aglycone (9) of 2 was composed of two molecules of 7. The position of ester and glycosidic linkage was confirmed by the NOE experiment of methylate (10) shown in Fig. 4. The structure of 9 was also confirmed by methanolysis of 10 to furnish two methylate 11 and 12 (Fig. 5).
天然有機化合物討論会の論文
1988-09-26