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.
Twenty-four new phenylpropanoid esters of sucrose, phanerosides A–X (1–24), were isolated from an EtOH extract of the rattans of Phanera championii Benth. (Fabaceae). Their structures were elucidated on the basis of comprehensive spectroscopic data analysis. A wide range of structural analogues were presented due to the different numbers and positions of acetyl substituents and the structures of phenylpropanoid moieties. Phenylpropanoid esters of sucrose were isolated from the Fabaceae family for the first time. Biologically, the inhibitory effects of compounds 6 and 21 on NO production in LPS-induced BV-2 microglial cells were better than that of the positive control, with IC50 values of 6.7 and 5.2 μM, respectively. The antioxidant activity assay showed that compounds 5, 15, 17, and 24 displayed moderate DPPH radical scavenging activity, with IC50 values ranging from 34.9 to 43.9 μM.
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