Chloraserrtone A, a Sesquiterpenoid Dimer from Chloranthus serratus

Abstract

Chloraserrtone A (1), a new sesquiterpenoid dimer with two lindenane-type sesquiterpenoid monomers bridged by two six-membered rings, was obtained from Chloranthus serratus. A combination of UV, IR, NMR, HRESIMS, and X-ray diffraction data were used to elucidate the structure of 1. Compound 1 represents the first lindenane-type sesquiterpenoid dimer with extremely unique C-15–C-15′, C-4–C-6′, and C-6–C-11′ linkages to form two six-membered rings between the monomeric units. A plausible biosynthesis toward chloraserrtone A is proposed. This new compound (1), together with the known lindenane dimers (2–11), were assessed for their inhibitory effects on lipopolysaccharide-induced NO production in RAW264.7 cells. Compound 6 showed activity with an IC50 value of 3.7 μM.

Chlorahupetenes A–D, Four Eudesmane-Type Sesquiterpenoid Dimer Enantiomers with Two Unusual Carbon Skeletons from Chloranthus henryi Var. hupehensis

“…On the one hand, two pairs of enantiomers, 3a , 4a and 3b , 4b , are generated from B a and B b , respectively, via a reduction reaction. On the other hand, the intermediates B a and B b yield 1a , 2a and 1b , 2b , respectively, via hydrolysis of the ether bond and lactone ring, dehydration, deprotonation, Michael addition, and interesterification…”

Chlorfortunones A and B, Two Sesquiterpenoid Dimers, Possessing Dispiro[4,2,5,2]pentadecane-6,10,14-tren Moiety from Chloranthus fortunei

“…In addition, a senecioyl moiety connected to C-7 was suggested by HMBC cross-peaks from H-6 to C-11 and from H-13 to C-7 and C-12. 11 …”

A New Labdane Diterpene from the Aerial Parts of Chloranthus serratus

“…It is used for the treatment of bruises, furuncles, snakebites, and rheumatoid arthritis in Traditional Chinese Medicine (TCM) [1]. Previous investigations of the constituents of this species resulted in the isolation of lindenane sesquiterpenoids [2,3], eudesmane sesquiterpenoids [4], phenylpropanoids [2], and labdane diterpenoids [5], several sesquiterpenoids showed antimicrobial and anti-inflammatory effects.…”

“…All compounds were tested for inhibitions against NO production in LPS-activated RAW 264.7 macrophages following the same procedures in the literature [3], as results, compounds 2 and 6 exhibited moderate inhibitory effects with IC50 values of 45.2  1.2 and 35.3  0.9 M, while the positive control quercetin possessed an IC50 of 15.2±1.3 M.…”