A new indole glycoside from Kitasatospora sp. MG372-hF19 carrying a 6-deoxy-α-l-talopyranose moiety
A new indole glycoside from Kitasatospora sp. MG372-hF19 carrying a 6-deoxy-α-l-talopyranose moiety
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来自 Kitasatospora sp. MG372-hF19 的新吲哚糖苷，带有 6-脱氧-α-l-吡喃糖部分。
DOI：
10.1038/s41429-019-0258-9
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Kawada M
中科院分区：
文献类型：
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作者：
Kohda Y;Sakamoto S;Otuka Y;Sawa R;Kubota Y;Igarashi M;Muramatsu H;Iijima M;Kawada M
小细胞肺癌（SCLC）是一种严重的恶性肿瘤，具有早期和广泛的转移，需要新的治疗药物。为了鉴定针对小细胞肺癌的细胞毒性天然化合物，我们使用几种肺癌细胞系筛选了微生物发酵液库。我们发现放线菌MG372-hF 19产生一种化合物，该化合物尚未从天然来源中分离出来，但以前是化学合成的，6-氯-1H-吲哚-3-甲醛（1），以及一种全新的化合物，命名为6-脱氧-α-L-吡喃塔罗糖1-（6-氯-1H-吲哚-3-羧酸酯）（2），以及瘦霉素。通过高分辨率电喷雾电离质谱法确定化合物的分子式分别为C9 H6 ClNO和C15 H16 ClNO 6，并通过详细核磁共振确定其结构。对化合物2的糖单元进行了绝对构型分析，发现化合物2中含有稀有的脱氧己糖6-脱氧-α-L-吡喃塔罗糖。这两种化合物对人肺癌细胞株均表现出较弱的生长抑制活性。
Small cell lung cancer (SCLC) is a severe malignancy with early and widespread metastasis, and novel therapeutic drugs are needed. To identify cytotoxic natural compounds against SCLC, we screened libraries of microbial fermentation broths using several lung cancer cell lines. We found that the actinomycete strain MG372-hF19 produces a compound that has not been isolated from natural sources but previously chemically synthesized, 6-chloro-1H-indole-3-carboxaldehyde (1), and an entirely new compound, named 6-deoxy-α-L-talopyranose 1-(6-chloro-1H-indole-3-carboxylate) (2), together with leptomycins. The molecular formulas of the compounds were established as C9H6ClNO and C15H16ClNO6, respectively, via high-resolution electrospray ionization mass spectrometry, and their structures were determined using detailed NMR. Absolute configurational analysis of the sugar unit of compound2revealed that the compound incorporates the rare deoxyhexose 6-deoxy-α-L-talopyranose. Both compounds exhibited weak growth-inhibiting activities against human lung cancer cell lines.