(+)-
and (−)-Chlorahupetenes A (1a and 1b), B (2a and 2b), C (3a and 3b), and D (4a and 4b), four unique
enantiomeric pairs of eudesmane-type sesquiterpenoid
dimers with two new carbon skeletons, were isolated from the aerial
parts of Chloranthus henryi var. hupehensis. Compounds 1 and 2 possess
an unprecedented 6/6/5/6/6 pentacyclic carbon skeleton with a new
dimerization pattern of two eudesmane-type sesquiterpenoids. Compounds 3 and 4, which are fused with two eudesmane-type
sesquiterpenoids via an unprecedented five-membered O-heterocyclic ring, represent a new 6/6/5/5/6/6/5 heptacyclic ring
system. The structures of the compounds were determined through spectroscopic
data and X-ray crystallography. Compounds 1a–3b significantly inhibited NO production with IC50 values ranging from 9.62 to 12.91 μM. Moreover, compounds 1b and 3a suppressed the production of a proinflammatory
mediator (TNF-α) and enzyme expression (iNOS) at the mRNA level.
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