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

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 sp. LC-MS analysis of the crude extract revealed that the natural products were present both as free porphyrins and iron(III) coordinated hemins, des...

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Bibliographic Details
Published in:Marine drugs 2023-01, Vol.21 (1), p.41
Main Authors: Sala, Samuele, Moggach, Stephen A, Nealon, Gareth L, Fromont, Jane, Gomez, Oliver, Vuong, Daniel, Lacey, Ernest, Flematti, Gavin R
Format: Article
Language:English
Subjects:
Analytical methods
Animals
Australia
Cell Line, Tumor
cytotoxic
Cytotoxicity
Enzymes
Experiments
Ferric Compounds
hemin
Hemin - metabolism
Iron
Isabela
Magnetic Resonance Spectroscopy
Marine invertebrates
Mass spectrometry
Mass spectroscopy
Metabolites
Mice
Multiple Myeloma
Myeloma
Natural products
NMR
NOESY NMR
Nuclear magnetic resonance
Porifera - metabolism
porphyrin
Porphyrins
Porphyrins - pharmacology
Single crystals
Toxicity
Ultraviolet spectroscopy
X-ray diffraction
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Summary: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 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.
ISSN:1660-3397
1660-3397
DOI:10.3390/md21010041