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

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.

Citation

Fan Yang, Bao-Jun Su, Ya-Jie Hu, Jin-Long Liu, Hua Li, Ya-Qi Wang, Hai-Bing Liao, Dong Liang. Piperhancins A and B, Two Pairs of Antineuroinflammatory Cycloneolignane Enantiomers from Piper hancei. The Journal of organic chemistry. 2021 Apr 02;86(7):5284-5291

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PMID: 33755467

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