Type-I Hemins and Free Porphyrins from a Western Australian Sponge Isabela sp.

被引:5
|
作者
Sala, Samuele [1 ,2 ,3 ]
Moggach, Stephen A. [1 ]
Nealon, Gareth L. [1 ,4 ]
Fromont, Jane [5 ]
Gomez, Oliver [5 ]
Vuong, Daniel [6 ]
Lacey, Ernest [6 ]
Flematti, Gavin R. [1 ]
机构
[1] Univ Western Australia, Sch Mol Sci, Crawley, WA 6009, Australia
[2] Murdoch Univ, Australian Natl Phenome Ctr, Harry Perkins Bldg, Perth, WA 6150, Australia
[3] Murdoch Univ, Hlth Futures Inst, Ctr Computat & Syst Med, Harry Perkins Bldg, Perth, WA 6150, Australia
[4] Univ Western Australia, Ctr Microscopy Characterisat & Anal, Crawley, WA 6009, Australia
[5] Western Australian Museum, Collect & Res, Welshpool, WA 6106, Australia
[6] Microbial Screening Technol Pty Ltd, Smithfield, NSW 2164, Australia
基金
澳大利亚研究理事会; 中国国家自然科学基金;
关键词
porphyrin; Isabela; hemin; X-ray diffraction; NOESY NMR; cytotoxic; DEMOSPONGE CORALLISTES-SP; CORAL SEA; BIOSYNTHESIS;
D O I
10.3390/md21010041
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two novel free porphyrins, isabellins A and B, as well as the known compounds corallistin D and deuteroporphyrin IX were isolated from a marine sponge Isabela sp. LC-MS analysis of the crude extract revealed that the natural products were present both as free porphyrins and iron(III) coordinated hemins, designated isabellihemin A, isabellihemin B, corallistihemin D and deuterohemin IX, respectively. Structures were determined via high-resolution mass spectrometry, UV-Vis spectroscopy and extensive NOESY NMR spectroscopic experiments. The type-I alkyl substitution pattern of isabellin A and isabellihemin A was assigned unambiguously by single crystal X-ray diffraction. Biological evaluation of the metabolites revealed potent cytotoxicity for isabellin A against the NS-1 murine myeloma cell line.
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页数:11
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