Viequeamide A, a cytotoxic member of the kulolide superfamily of cyclic depsipeptides from a marine button cyanobacterium.
Viequeamide A, a cytotoxic member of the kulolide superfamily of cyclic depsipeptides from a marine button cyanobacterium.
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DOI：
10.1021/np300321b
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发表时间：
2012-09-28
影响因子：
5.1
通讯作者：
Gerwick WH
中科院分区：
文献类型：
--
作者：
Boudreau PD;Byrum T;Liu WT;Dorrestein PC;Gerwick WH
VIQEAIADIES是一个含有环状脱脂肽的2，2-二甲基-3-羟基-7-辛酸(DOYA)家族，它是从浅潮下采集的一种‘纽扣’蓝藻(Riugaria sp.)来自波多黎各别克斯岛附近。两个主要化合物维奎酰胺A(1)和维奎酰胺B(2)的平面结构通过2D-核磁共振波谱和质谱学得到确证，而绝对构型的确定是通过传统的水解法、衍生物法和层析法确定的。此外，还用高分辨质谱仪(HRMS)对一系列相关的次生代谢产物--维奎酰胺C-F(3-6)进行了表征。别克酰胺A对H460人肺癌细胞有较强的毒性(IC50=60±10 nM)，而B-F混合物对H460人肺癌细胞无活性。从更广泛的角度来看，VIQEACEAMIES有助于定义相关蓝藻天然产物的“超级家族”，其中第一个被发现的是‘kulolide’。在kulolide超家族中，观察到了生物学特性的广泛差异，已报道的产生菌株也高度不同，这引发了关于结构-活性关系和这种代谢物类别的进化起源的几个有趣的问题。
The viequeamides, a family of 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya) containing cyclic depsipeptides, were isolated from a shallow subtidal collection of a ‘button’ cyanobacterium (Rivularia sp.) from near the island of Vieques, Puerto Rico. Planar structures of the two major compounds, viequeamide A (1) and viequeamide B (2), were elucidated by 2D-NMR spectroscopy and mass spectrometry, whereas absolute configurations were determined by traditional hydrolysis, derivative formation, and chromatography in comparison with standards. In addition, a series of related minor metabolites, viequeamide C–F (3–6), were characterized by high resolution mass spectroscopic (HRMS) fragmentation methods. Viequeamide A was found to be highly toxic to H460 human lung cancer cells (IC50 = 60 ± 10 nM), whereas the mixture of B–F was inactive. From a broader perspective, the viequeamides help to define a “superfamily” of related cyanobacterial natural products, the first of which to be discovered was ‘kulolide’. Within the kulolide superfamily, a wide variation in biological properties is observed, and the reported producing strains are also highly divergent, giving rise to several intriguing questions about structure-activity relationships and the evolutionary origins of this metabolite class.
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影响因子：
3.8
作者：
Montaser R;Paul VJ;Luesch H
通讯作者：
Luesch H
影响因子：
3.2
作者：
Pereira, Alban R.;Kale, Andrew J.;Fenley, Andrew T.;Byrum, Tara;Debonsi, Hosana M.;Gilson, Michael K.;Valeriote, Frederick A.;Moore, Bradley S.;Gerwick, William H.
通讯作者：
Gerwick, William H.
影响因子：
5.1
作者：
Mevers E;Liu WT;Engene N;Mohimani H;Byrum T;Pevzner PA;Dorrestein PC;Spadafora C;Gerwick WH
通讯作者：
Gerwick WH
影响因子：
3.6
作者：
Han, BN;Goeger, D;Gerwick, WH
通讯作者：
Gerwick, WH
影响因子：
3.6
作者：
Nakao, Y;Yoshida, WY;Scheuer, PJ
通讯作者：
Scheuer, PJ