Structure Elucidation of Two Intriguing Neo-Debromoaplysiatoxin Derivatives from Marine Cyanobacterium Lyngbya sp. Showing Strong Inhibition of Kv1.5 Potassium Channel and Differential Cytotoxicity.
Structure Elucidation of Two Intriguing Neo-Debromoaplysiatoxin Derivatives from Marine Cyanobacterium Lyngbya sp. Showing Strong Inhibition of Kv1.5 Potassium Channel and Differential Cytotoxicity.
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DOI：
10.3390/molecules28062786
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发表时间：
2023-03-20
期刊：
影响因子：
--
通讯作者：
Han B
中科院分区：
文献类型：
--
作者：
Chen Z;Chen N;Fu P;Wang W;Bian S;Zhang H;Shen S;Han B
从海洋蓝藻lyngbya sp.中分离得到2个新脱溴青霉毒素I(neo-debromoaplysiatoxin I)和新脱溴青霉毒素J(neo-debromoaplysiatoxin J)。采自南洋中国海域。通过光谱分析，结合Giao核磁共振位移计算和DP4+分析，确定了它们的结构，包括绝对构型。新脱溴海藻毒素I和新脱溴海藻毒素J分别含有一个十氢-5H-吡喃并[2，3，4-de]色满-5-酮6/6/6环骨架和一个有趣的过氧化桥基团，这是海藻毒素中前所未有的结构支架和基序。两个化合物对Kv1.5K+通道具有相似的抑制活性，IC50值分别为2.59±0.37μM(1)和1.64±0.15μM(2)，但呈现不同的细胞毒作用。值得注意的是，含有过氧化桥的新脱溴青霉毒素J与人正常细胞株相比，对SW480、SGC7901、LoVo和PC-9等四种癌细胞具有显著的细胞毒作用。
Two aplysiatoxin derivatives, neo-debromoaplysiatoxin I (1) and neo-debromoaplysiatoxin J (2), were isolated from marine cyanobacterium Lyngbya sp. collected from the South China Sea. Their structures including absolute configurations were assigned by spectroscopic analysis, in combination with GIAO NMR shift calculation and DP4+ analysis. Structures of neo-debromoaplysiatoxin I and neo-debromoaplysiatoxin J contained a decahydro-5H-pyrano [2,3,4-de] chromen-5-one 6/6/6 ring skeleton and an intriguing peroxide bridge group, respectively, which are unprecedented structure scaffold and motif in aplysiatoxins. Two compounds displayed comparable inhibitory activities against Kv1.5 K+ channel with IC50 values of 2.59 ± 0.37 μM (1) and 1.64 ± 0.15 μM (2); however, they presented differential cytotoxic effects. It is worth noting that neo-debromoaplysiatoxin J, containing a peroxide bridge, showed remarkable cytotoxicity against four cancer cell lines including SW480, SGC7901, LoVo and PC-9 compared to the human normal cell line.
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影响因子：
5.4
作者：
Shen S;Wang W;Chen Z;Zhang H;Yang Y;Wang X;Fu P;Han B
通讯作者：
Han B
影响因子：
3.5
作者：
Ashida, Yoshiki;Yanagita, Ryo C.;Irie, Kazuhiro
通讯作者：
Irie, Kazuhiro
影响因子：
7.7
作者：
Fattorusso, Ernesto;Taglialatela-Scafati, Orazio
通讯作者：
Taglialatela-Scafati, Orazio
蓝藻毒素和神经系统。
影响因子：
4.2
作者：
Metcalf JS;Tischbein M;Cox PA;Stommel EW
通讯作者：
Stommel EW
影响因子：
5.1
作者：
Hamilton TL;Bryant DA;Macalady JL
通讯作者：
Macalady JL