Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants
Verano, AL; Tan, DS
| HERO ID | 5410469 |
|---|---|
| In Press | No |
| Year | 2017 |
| Title | Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants |
| Authors | Verano, AL; Tan, DS |
| Journal | Chemical Science |
| Volume | 8 |
| Issue | 5 |
| Page Numbers | 3687-3693 |
| 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. |
| Doi | 10.1039/c6sc05505b |
| Pmid | 28845229 |
| Wosid | WOS:000400553000046 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |