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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MSK Authors
  1. Derek S Tan
    68 Tan
  2. Alyssa Verano
    2 Verano