Two cytotoxic stereoisomers of malyngamide C, 8-epi-malyngamide C and 8-O-acetyl-8-epi-malyngamide C, from the marine cyanobacterium Lyngbya majuscula.

Two cytotoxic stereoisomers of malyngamide C, 8-epi-malyngamide C and 8-O-acetyl-8-epi-malyngamide C, from the marine cyanobacterium Lyngbya majuscula.
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DOI:
10.1016/j.phytochem.2010.07.001
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发表时间:
2010-10
期刊:
影响因子:
3.8
通讯作者:
Gerwick WH
Gerwick WH
中科院分区:
生物学2区
文献类型:
--
作者:
Gross H;McPhail KL;Goeger DE;Valeriote FA;Gerwick WH

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从格林纳达海洋蓝细菌Lyngbya majuscula中分离出两种新的苹果酸酰胺C的差向异构体8-O-乙酰基-8-epi-malyngamide C(1)和8-epi-malyngamide C(3)以及已知化合物6-O-乙酰基苹果酸酰胺F(5)、H(6)、J(7)、K(8),并对其进行了表征。这些化合物的平面结构由1D-和2D-NMR和质谱数据解释推断。的绝对构型的CD-光谱,化学降解和变温Mosher的方法的组合确定。化合物1-5、7和8对NCI-H460人肺肿瘤和neuro-2a癌细胞系显示中等细胞毒性,IC 50值在0.5和20 μg/mL之间。
Two new epimers of malyngamide C, 8-O-acetyl-8-epi-malyngamide C (1) and 8-epi-malyngamide C (3) have been isolated along with known compounds 6-O-acetylmalyngamide F (5), H (6), J (7) K (8), and characterized from a Grenada field collection of the marine cyanobacterium Lyngbya majuscula. The planar structures of these compounds were deduced by 1D- and 2D-NMR and mass spectral data interpretation. The absolute configurations were determined by a combination of CD-spectroscopy, chemical degradation and the variable temperature Mosher’s method. Compounds 1–5, 7 and 8 displayed moderate cytotoxicity to NCI-H460 human lung tumor and neuro-2a cancer cell lines, with IC50 values ranging between 0.5 and 20 μg/mL.
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