Identification of Novel Gymnodimines and Spirolides from the Marine Dinoflagellate Alexandrium ostenfeldii.
Identification of Novel Gymnodimines and Spirolides from the Marine Dinoflagellate Alexandrium ostenfeldii.
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鉴定海洋鞭毛鞭毛盐Alexandrium ostenfeldii的新颖的体育胺和螺母。
DOI：
10.3390/md16110446
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发表时间：
2018-11-14
期刊：
影响因子：
5.4
通讯作者：
Tebben J
中科院分区：
文献类型：
--
作者：
Zurhelle C;Nieva J;Tillmann U;Harder T;Krock B;Tebben J
环亚胺毒素是由海洋甲藻产生的具有神经毒性的大环化合物。对天然浮游生物组合提取物的质谱学筛选显示，这类毒素具有高度的化学多样性，但结构上已知的毒素很少。在这里，我们报道了四种新的环亚胺类毒素(两种裸子酸酯(GYM)和两种螺内酯(SPX))的结构特征。经鉴定，m/z为510(1)的GYM为16-脱甲基GYM D。m/z为526的GYM为(1)的羟基化降解产物，C-17为外环亚甲基，C-18为烯丙基。该化合物被命名为健身房E(2)。进一步鉴定了m/z为694的SPX为20-羟基-13，19-二脱甲基SPX C(10)和m/z为696的SPX为20-羟基-13，19-二脱甲基SPX D(11)。这是首次报道D环上没有甲基的GYM和C-20位上有羟基的SPX。这些化合物可以被认为是同一新生聚酮链的衍生物，支持健身房和SPX是通过共同的生物合成基因产生的假说。在天然浮游生物组合的提取物中检测到两个新的健身器1和2(每毫升过滤海水分别为1：447pg、2：1250pg和11：40pg)。
Cyclic imine toxins are neurotoxic, macrocyclic compounds produced by marine dinoflagellates. Mass spectrometric screenings of extracts from natural plankton assemblages revealed a high chemical diversity among this toxin class, yet only few toxins are structurally known. Here we report the structural characterization of four novel cyclic-imine toxins (two gymnodimines (GYMs) and two spirolides (SPXs)) from cultures of Alexandrium ostenfeldii. A GYM with m/z 510 (1) was identified as 16-desmethylGYM D. A GYM with m/z 526 was identified as the hydroxylated degradation product of (1) with an exocyclic methylene at C-17 and an allylic hydroxyl group at C-18. This compound was named GYM E (2). We further identified a SPX with m/z 694 as 20-hydroxy-13,19-didesmethylSPX C (10) and a SPX with m/z 696 as 20-hydroxy-13,19-didesmethylSPX D (11). This is the first report of GYMs without a methyl group at ring D and SPXs with hydroxyl groups at position C-20. These compounds can be conceived as derivatives of the same nascent polyketide chain, supporting the hypothesis that GYMs and SPXs are produced through common biosynthetic genes. Both novel GYMs 1 and 2 were detected in significant amounts in extracts from natural plankton assemblages (1: 447 pg; 2: 1250 pg; 11: 40 pg per mL filtered seawater respectively).
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影响因子：
4.7
作者：
Molgó J;Marchot P;Aráoz R;Benoit E;Iorga BI;Zakarian A;Taylor P;Bourne Y;Servent D
通讯作者：
Servent D
影响因子：
11.9
作者：
Stivala CE;Benoit E;Aráoz R;Servent D;Novikov A;Molgó J;Zakarian A
通讯作者：
Zakarian A
影响因子：
2
作者：
Aasen, John A. B.;Hardstaff, William;Quilliam, Michael A.
通讯作者：
Quilliam, Michael A.
影响因子：
4.9
作者：
Furrer, Julien
通讯作者：
Furrer, Julien
影响因子：
5.1
作者：
Roach, Joy S.;LeBlanc, Patricia;MacKinnon, Shawna L.
通讯作者：
MacKinnon, Shawna L.