Natural Products Containing Hydrogen Sulfide Releasing Moieties

Michael D. Pluth; T. Spencer Bailey; Matthew D. Hammers; Matthew D. Hartle; Hillary A. Henthorn; Andrea K. Steiger

doi:10.1055/s-0035-1560638

Synlett, Table of Contents

Synlett 2015; 26(19): 2633-2643
DOI: 10.1055/s-0035-1560638

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Natural Products Containing Hydrogen Sulfide Releasing Moieties

Michael D. Pluth*

Department of Chemistry and Biochemistry, Institute of Molecular Biology, Materials Science Institute, University of Oregon, Eugene, OR 97403, USA Email: pluth@uoregon.edu

,

T. Spencer Bailey

Department of Chemistry and Biochemistry, Institute of Molecular Biology, Materials Science Institute, University of Oregon, Eugene, OR 97403, USA Email: pluth@uoregon.edu

,

Matthew D. Hammers

Department of Chemistry and Biochemistry, Institute of Molecular Biology, Materials Science Institute, University of Oregon, Eugene, OR 97403, USA Email: pluth@uoregon.edu

,

Matthew D. Hartle

Department of Chemistry and Biochemistry, Institute of Molecular Biology, Materials Science Institute, University of Oregon, Eugene, OR 97403, USA Email: pluth@uoregon.edu

,

Hillary A. Henthorn

Department of Chemistry and Biochemistry, Institute of Molecular Biology, Materials Science Institute, University of Oregon, Eugene, OR 97403, USA Email: pluth@uoregon.edu

,

Andrea K. Steiger

Department of Chemistry and Biochemistry, Institute of Molecular Biology, Materials Science Institute, University of Oregon, Eugene, OR 97403, USA Email: pluth@uoregon.edu

› Author Affiliations

Abstract

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Abstract

Hydrogen sulfide (H₂S) is now recognized as an important biological molecule that plays diverse roles in various (patho)physiological conditions. Endogenous H₂S, or its misregulation, has been associated with a variety of aspects of human health, including diabetes, hypertension, atherosclerosis, inflammation, neurodegeneration, sepsis, and asthma. Motivated by the potential use of H₂S-donating molecules as both investigative and therapeutic tools, researchers are developing new types of slow-releasing H₂S donor molecules that mimic the slow, continuous H₂S release characteristic of enzymatic production. In addition to synthetic H₂S donors, many natural products contain functional groups well known to release sulfide. Here we provide an overview of natural products that contain such functional groups, with an emphasis on organic polysulfides, to highlight the diversity of these structures and also to outline possible areas of future research on pharmacologically relevant H₂S donors derived from natural products.

1 Introduction

2 Polysulfide-Containing Natural Products

2.1 Linear Polysulfides

2.2 Cyclic Polysulfides

2.3 Epidithiodioxopiperazines

2.4 Enediyne-Containing Trisulfides

3 Leinamycin

4 Other Disulfides and Thiols Implicated in Hydrogen Sulfide Generation

5 Conclusions and Prospects

Key words

hydrogen sulfide - polysulfides - bioorganic chemistry - sulfur - redox chemistry

Full Text

References

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