HYDROLYSABLE TANNINS ISOLATED FROM SYZYGIUM AROMATICUM: STRUCTURE OF A NEW C-GLUCOSIDIC ELLAGITANNIN AND SPECTRAL FEATURES OF TANNINS WITH A TERGALLOYL GROUP
HYDROLYSABLE TANNINS ISOLATED FROM SYZYGIUM AROMATICUM: STRUCTURE OF A NEW C-GLUCOSIDIC ELLAGITANNIN AND SPECTRAL FEATURES OF TANNINS WITH A TERGALLOYL GROUP
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DOI：
10.3987/com-11-12392
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发表时间：
2012-02-01
期刊：
影响因子：
0.6
通讯作者：
Hatano, Tsutomu
中科院分区：
文献类型：
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作者：
Bao, Li-Ming;Eerdunbayaer;Hatano, Tsutomu
从丁香（Syzygium aromaticum Merr.）还有佩里。我们确定1具有没食子酸C-葡萄糖苷结构，基于光谱数据和从黄芩素（18）和没食子酸（20）的合成。这是具有没食子酸C-葡萄糖苷结构的可水解单宁的罕见实例。我们还报道了从S.芳香族化合物，基于其具有三苯甲酰基或其缩酚酮形式的结构。其余的已知化合物被鉴定为alunusnin A（5）、rugosin C（6）、1，2，3-三-O-没食子酰基-β-D-葡萄糖（7）、1，2，3，6-四-O-没食子酰基-β-D-葡萄糖（8）、tellimagrandin 11（9）、异甘草素（10）、异甘草素D（11）、rugosin D（12）、rugosin F（13）、euprostin A（14）、1，2-二-O-没食子酰基-3-O-二没食子酰基-4，6-O-（S）-六羟基联苯酰基-β-D-葡萄糖（15）、洋地黄苷B（16）、番石榴苷A（17）和18。水解单宁，9，12和18对念珠菌菌株的抗真菌作用也进行了描述。
Eighteen hydrolysable tannins, including a new C-glucosidic tannin named aromatinin A (1), were isolated from an aqueous acetone extract of dried flower buds of Syzygium aromaticum Merr. et Perry. We determined that 1 had a gallic acid C-glucoside structure, based on the spectral data and synthesis from casuarinin (18) and gallic acid (20). This is a rare example of hydrolysable tannins with gallic acid C-glucoside structure. We also report the H-1 nuclear magnetic resonance (NMR) spectral features of syzyginin A (2), bicornin (3), and platycaryanin A (4), which were also isolated from S. aromaticum, based on their structures with a tergalloyl group or its depsidone form. The remaining known compounds were identified as alunusnin A (5), rugosin C (6), 1,2,3-tri-O-galloyl-beta-D-glucose (7), 1,2,3,6-tetra-O-galloyl-beta-D-glucose (8), tellimagrandin 11 (9), casuarictin (10), heterophylliin D (11), rugosin D (12), rugosin F (13), euprostin A (14), 1,2-di-O-galloyl-3-O-digalloyl-4,6-O-(S)-hexahydroxydiphenoy-beta-D-glucose (15), alienanin B (16), squarrosanin A (17), and 18. The antifungal effects of hydrolysable tannins, 9, 12, and 18 against Candida strains are also described.