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

Samuele Sala; Stephen A. Moggach; Gareth L. Nealon; Jane Fromont; Oliver Gomez; Daniel Vuong; Ernest Lacey; Gavin R. Flematti

doi:10.3390/md21010041

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

Samuele Sala, Stephen A. Moggach, Gareth L. Nealon, Jane Fromont, Oliver Gomez, Daniel Vuong, Ernest Lacey, Gavin R. Flematti

Research output: Contribution to journal › Article › peer-review

6 Citations (Web of Science)

Abstract

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.

Original language	English
Article number	41
Journal	Marine Drugs
Volume	21
Issue number	1
DOIs	https://doi.org/10.3390/md21010041
Publication status	Published - Jan 2023

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title = "Type-I Hemins and Free Porphyrins from a Western Australian Sponge Isabela sp.",

abstract = "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.",

keywords = "cytotoxic, hemin, Isabela, NOESY NMR, porphyrin, X-ray diffraction",

author = "Samuele Sala and Moggach, {Stephen A.} and Nealon, {Gareth L.} and Jane Fromont and Oliver Gomez and Daniel Vuong and Ernest Lacey and Flematti, {Gavin R.}",

note = "Funding Information: S.A.M. thanks the Australian Research Council (ARC) for a Future Fellowship (FT200100243). Funding Information: This work was supported by the Natural Science Foundation of Jiangxi Province (20212BAB216016), National Natural Science Foundation of China (81900500, 81870395, 82170580), Doctoral Research Initiation Funding (701221002), and Young Medical Teacher Training Fund of Nanchang University (4209-16100009-PY201923). Publisher Copyright: {\textcopyright} 2023 by the authors.",

year = "2023",

month = jan,

doi = "10.3390/md21010041",

language = "English",

volume = "21",

journal = "Marine Drugs",

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publisher = "MDPI Multidisciplinary Digital Publishing Institute",

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T1 - Type-I Hemins and Free Porphyrins from a Western Australian Sponge Isabela sp.

AU - Sala, Samuele

AU - Moggach, Stephen A.

AU - Nealon, Gareth L.

AU - Fromont, Jane

AU - Gomez, Oliver

AU - Vuong, Daniel

AU - Lacey, Ernest

AU - Flematti, Gavin R.

N1 - Funding Information: S.A.M. thanks the Australian Research Council (ARC) for a Future Fellowship (FT200100243). Funding Information: This work was supported by the Natural Science Foundation of Jiangxi Province (20212BAB216016), National Natural Science Foundation of China (81900500, 81870395, 82170580), Doctoral Research Initiation Funding (701221002), and Young Medical Teacher Training Fund of Nanchang University (4209-16100009-PY201923). Publisher Copyright: © 2023 by the authors.

PY - 2023/1

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N2 - 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.

AB - 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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SN - 1660-3397

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JO - Marine Drugs

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

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Fill it, Squeeze it, Crush it: Extreme Gas Uptake in Microporous Materials

Chemical and biological investigations into the major secondary metabolites isolated from marine sponges of the Western Australian coast

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

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Fill it, Squeeze it, Crush it: Extreme Gas Uptake in Microporous Materials

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Chemical and biological investigations into the major secondary metabolites isolated from marine sponges of the Western Australian coast

Cite this