Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants Journal Article
| Authors: | Verano, A. L.; Tan, D. S. |
| Article Title: | Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants |
| Abstract: | The pyranose spiroketal natural products pollenopyrroside A and shensongine A (also known as xylapyrroside A, ent-capparisine B) have been synthesized by stereoselective spirocyclizations of a common C1-functionalized glycal precursor. In conjunction with our previously reported syntheses of the corresponding furanose isomers, this provides a versatile family-level synthesis of the pyrrolomorpholine spiroketal natural products and analogues. In rat mesangial cells, hyperglycemia-induced production of reactive oxygen species, which is implicated in diabetic nephropathy, was inhibited by pollenopyrroside A and shensongine A with mid-μM IC50 values, while unnatural C2-hydroxy analogues exhibited more potent, sub-μM activity. © 2017 The Royal Society of Chemistry. |
| Keywords: | reactive oxygen species; diabetic nephropathy; stereochemistry; functionalized; stereo-selective; natural products; stereoselectivity; isomers; biological evaluation; stereoselective synthesis; rat mesangial cell |
| Journal Title: | Chemical Science |
| Volume: | 8 |
| Issue: | 5 |
| ISSN: | 2041-6520 |
| Publisher: | Royal Society of Chemistry |
| Date Published: | 2017-05-01 |
| Start Page: | 3687 |
| End Page: | 3693 |
| Language: | English |
| DOI: | 10.1039/c6sc05505b |
| PROVIDER: | scopus |
| PMCID: | PMC5571482 |
| PUBMED: | 28845229 |
| DOI/URL: | |
| Notes: | Article -- Export Date: 2 August 2017 -- Source: Scopus |
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