Suberitamides A–C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity

Chang-Kwon Kim; Dongdong Wang; Brice A. P. Wilson; Josep Sauri; Donna Voeller; Stanley Lipkowitz; Barry R. O'Keefe; Kirk R. Gustafson

doi:10.3390/md18110536

Suberitamides A–C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity

Chang-Kwon Kim, Dongdong Wang, Brice A. P. Wilson, Josep Sauri, Donna Voeller, Stanley Lipkowitz, Barry R. O'Keefe, Kirk R. Gustafson

Research output: Indexed journal article › Article › peer-review

5 Citations (Scopus)

Abstract

Three new aryl alkaloids named suberitamides A-C (1-3), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond H-1-C-13 spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 mu M.

Original language	English
Article number	536
Number of pages	11
Journal	Marine Drugs
Volume	18
Issue number	11
DOIs	https://doi.org/10.3390/md18110536
Publication status	Published - Nov 2020
Externally published	Yes

Keywords

Cbl-b ubiquitin ligase inhibition
Pip hsqmbc ipap
Pseudosuberites sp
Marine sponge
Suberitamides

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md18110536

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title = "Suberitamides A–C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity",

abstract = "Three new aryl alkaloids named suberitamides A-C (1-3), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond H-1-C-13 spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 mu M.",

keywords = "Cbl-b ubiquitin ligase inhibition, Pip hsqmbc ipap, Pseudosuberites sp, Marine sponge, Suberitamides",

author = "Chang-Kwon Kim and Dongdong Wang and Wilson, {Brice A. P.} and Josep Sauri and Donna Voeller and Stanley Lipkowitz and O'Keefe, {Barry R.} and Gustafson, {Kirk R.}",

year = "2020",

month = nov,

doi = "10.3390/md18110536",

language = "English",

volume = "18",

journal = "Marine Drugs",

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AU - Kim, Chang-Kwon

AU - Wang, Dongdong

AU - Wilson, Brice A. P.

AU - Sauri, Josep

AU - Voeller, Donna

AU - Lipkowitz, Stanley

AU - O'Keefe, Barry R.

AU - Gustafson, Kirk R.

PY - 2020/11

Y1 - 2020/11

N2 - Three new aryl alkaloids named suberitamides A-C (1-3), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond H-1-C-13 spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 mu M.

AB - Three new aryl alkaloids named suberitamides A-C (1-3), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond H-1-C-13 spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 mu M.

KW - Cbl-b ubiquitin ligase inhibition

KW - Pip hsqmbc ipap

KW - Pseudosuberites sp

KW - Marine sponge

KW - Suberitamides

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DO - 10.3390/md18110536

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JO - Marine Drugs

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Suberitamides A–C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity

Abstract

Keywords

UN SDGs

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