Piperhancins A and B, Two Pairs of Antineuroinflammatory Cycloneolignane Enantiomers from Piper hancei.

Abstract

Two pairs of cycloneolignane enantiomers, piperhancins A and B (1 and 2, respectively), along with two enantiomeric pairs of biosynthetic related neolignanes, hancinone C (3) and piperhancin C (4), were isolated from the stems of Piper hancei. Compound 1 is an unprecedented 1',2:1,2'-dicyclo-8,3'-neolignane. Their structures and absolute configurations were elucidated by spectroscopic analyses, X-ray diffraction, and electronic circular dichroism calculations. Among all of the isolates, compounds (+)-1, (-)-1, (+)-2, (-)-2, and (+)-3 could significantly inhibit the production of nitric oxide secreted by lipopolysaccharide (LPS)-induced neuroinflammation in BV-2 microglial cells, with IC50 values of 1.1-26.3 μM. In addition, compound (-)-1 could decrease the mRNA levels of iNOS, IL-6, and TNF-α induced by LPS in BV-2 microglial cells.

• Authors: Fan Yang, Bao-Jun Su, Ya-Jie Hu, Jin-Long Liu, Hua Li, Ya-Qi Wang, Hai-Bing Liao, Dong Liang
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 86 Issue 7 Pg. 5284-5291 (04 02 2021) ISSN: 1520-6904 [Electronic] United States
• PMID: 33755467 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Lipopolysaccharides
• Nitric Oxide

Topics

• Lipopolysaccharides
• Microglia
• Molecular Structure
• Nitric Oxide
• Piper
• Stereoisomerism