Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.

John A. Kalaitzis; Priscila de Almeida Leone; John N. A. Hooper; Ronald J. Quinn

doi:10.1080/14786410701763411

Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.

John A. Kalaitzis, Priscila de Almeida Leone, John N. A. Hooper, Ronald J. Quinn^*

^*Corresponding author for this work

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

22 Citations (Scopus)

Abstract

The new compound ianthesine E (1) was isolated from the Great Barrier Reef marine sponge Pseudoceratina sp. along with the known metabolites 11-hydroxyaerothionin (2), aerothionin (3) and 11,19-dideoxyfistularin 3 (4). Structures were determined on the basis of their spectroscopic data. The compounds were tested for inhibition of [³H] DPCPX binding to adenosine A₁ receptors in a whole cell binding assay. At 100 μM, aerothionin was the most potent, inhibiting 67% of binding, followed by ianthesine E and 11-hydroxyaerothionin which inhibited 61% of binding, and 11,19-dideoxyfistularin which initiated 51% of binding Ianthesine E (EC₅₀ 60 μM), aerothionin (EC₅₀ 42 μM) and 11,19-dideoxyfistularin-3 (EC₅₀ 2.6 μM) exhibited moderate cytotoxicity against the HeLa cell line.

Original language	English
Pages (from-to)	1257-1263
Number of pages	7
Journal	Natural Product Research
Volume	22
Issue number	14
DOIs	https://doi.org/10.1080/14786410701763411
Publication status	Published - 20 Sept 2008
Externally published	Yes

Keywords

Ianthesine
Marine sponge
Pseudoceratina
Adenosine receptors

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10.1080/14786410701763411

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title = "Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.",

abstract = "The new compound ianthesine E (1) was isolated from the Great Barrier Reef marine sponge Pseudoceratina sp. along with the known metabolites 11-hydroxyaerothionin (2), aerothionin (3) and 11,19-dideoxyfistularin 3 (4). Structures were determined on the basis of their spectroscopic data. The compounds were tested for inhibition of [3H] DPCPX binding to adenosine A1 receptors in a whole cell binding assay. At 100 μM, aerothionin was the most potent, inhibiting 67% of binding, followed by ianthesine E and 11-hydroxyaerothionin which inhibited 61% of binding, and 11,19-dideoxyfistularin which initiated 51% of binding Ianthesine E (EC50 60 μM), aerothionin (EC50 42 μM) and 11,19-dideoxyfistularin-3 (EC50 2.6 μM) exhibited moderate cytotoxicity against the HeLa cell line.",

keywords = "Ianthesine, Marine sponge, Pseudoceratina, Adenosine receptors",

author = "Kalaitzis, {John A.} and {de Almeida Leone}, Priscila and Hooper, {John N. A.} and Quinn, {Ronald J.}",

year = "2008",

month = sep,

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doi = "10.1080/14786410701763411",

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AU - Kalaitzis, John A.

AU - de Almeida Leone, Priscila

AU - Hooper, John N. A.

AU - Quinn, Ronald J.

PY - 2008/9/20

Y1 - 2008/9/20

N2 - The new compound ianthesine E (1) was isolated from the Great Barrier Reef marine sponge Pseudoceratina sp. along with the known metabolites 11-hydroxyaerothionin (2), aerothionin (3) and 11,19-dideoxyfistularin 3 (4). Structures were determined on the basis of their spectroscopic data. The compounds were tested for inhibition of [3H] DPCPX binding to adenosine A1 receptors in a whole cell binding assay. At 100 μM, aerothionin was the most potent, inhibiting 67% of binding, followed by ianthesine E and 11-hydroxyaerothionin which inhibited 61% of binding, and 11,19-dideoxyfistularin which initiated 51% of binding Ianthesine E (EC50 60 μM), aerothionin (EC50 42 μM) and 11,19-dideoxyfistularin-3 (EC50 2.6 μM) exhibited moderate cytotoxicity against the HeLa cell line.

AB - The new compound ianthesine E (1) was isolated from the Great Barrier Reef marine sponge Pseudoceratina sp. along with the known metabolites 11-hydroxyaerothionin (2), aerothionin (3) and 11,19-dideoxyfistularin 3 (4). Structures were determined on the basis of their spectroscopic data. The compounds were tested for inhibition of [3H] DPCPX binding to adenosine A1 receptors in a whole cell binding assay. At 100 μM, aerothionin was the most potent, inhibiting 67% of binding, followed by ianthesine E and 11-hydroxyaerothionin which inhibited 61% of binding, and 11,19-dideoxyfistularin which initiated 51% of binding Ianthesine E (EC50 60 μM), aerothionin (EC50 42 μM) and 11,19-dideoxyfistularin-3 (EC50 2.6 μM) exhibited moderate cytotoxicity against the HeLa cell line.

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KW - Adenosine receptors

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JO - Natural Product Research

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ER -

Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.

Abstract

Keywords

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