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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-?M IC₅₀ values, while unnatural C2-hydroxy analogues exhibited more potent, sub-?M activity.

SUBMITTER: Verano AL

PROVIDER: S-EPMC5571482 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.

Verano Alyssa L AL Tan Derek S DS

Chemical science 20170315 5

The pyranose spiroketal natural products pollenopyrroside A and shensongine A (also known as xylapyrroside A, <i>ent</i>-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 p ...[more]

PMID: 28845229

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