Phylogeny in Chloranthus Swartz (Chloranthaceae) Inferred from Sequence Analysis of nrDNA ITS Region

The internal transcribed spacer (ITS) regions of nuclear ribosomal DNA from ten species of Chloranthus Swartz and two outgroup species of Sarcandra Gardn. were sequenced. The regions ranged in length from 654 to 663 bp, with ITS1 (285-290 bp) slightly longer than ITS2 (205-211 bp). Of the 669 aligned positions, 109 sites (56 in ITS1, 52 in ITS2, and one in 5.8S region) were phylogenetically informative. Only one most parsimonious tree of 252 steps was obtained in PAUP analysis when gaps were treated as the fifth state. The traditional division of Chloranthus on the basis of habit seems to be quite unnatural. Evidence from the sequence of ITS region, just as that from cytology and anatomy, strongly suggested the separation of the genus into two groups according to the characteristics of androecial organs: one contains C. angustifolius, C. nervosus, C. japonicus and C. fortunei, and the other comprises the remaining species.

A new tetrahydrophenanthrene from Chloranthus henryi

A new tetrahydrophenanthrene named henryin A(1) was isolated from the leaves of Chloranthus henryi.Its structure was determined to be(S)-4,6,9-trimethyl-5,6,7,8-tetrahydrophenanthrene-1,2-diol on the basis of IR,MS,1D and 2D NMR spectral.

Terpenoids from Chloranthus elatior

Two new eudesmane-type sesquiterpenoid lactones,named chlorelactone A(1)and chlorelactone B(2),and one new labdane-type diterpenoid,named elatiorlabdane(3),along with seven known sesquiterpenoids and one known disesquiterpenoid were isolated from the whole plants of Chloranthus elatior.Their structures and relative configurations were established on the basis of extensive spectroscopic analysis.

Chemical Composition and Antimicrobial Activity of <i>Pituranthos chloranthus</i>(Benth.) Hook and <i>Pituranthos tortu-osus</i>(Coss.) Maire Essential Oils from Southern Tunisia

Essential oils (EO) from fresh and dry aerial parts of Pituranthos chloranthus (Benth.) Hook and Pituranthos tortuosus (Coss.) Maire were isolated by hydrodistillation and analyzed by GC/MS. The main constituents of the EO obtained from fresh herb of P. chloranthus were found to be α-pinene, sabinene, cis-ocimene and myrcene. In dry biomass, a significant increase of the content of some compounds such as α-phellandrene, △,3-carene and β-phellandrene characterized the oil. Minor changes in the chemical composition of the P. tortuosus EOs obtained from fresh or dry herbs and the major constituents were found to be sabinene and myrcene with equilibrate amounts of α-pinene, p-cymene, cis-ocimene, limonene, trans-β-ocimene, γ-terpinene and cis-verbenol. The paper disc diffusion method was used to evaluate the antibacterial activity and results showed an important inhibitory effect of oils obtained from fresh herb against most tested bacteria.

Research review on the main chemical constituents and pharmacological effects of Chloranthus japonicus Sieb.

Chloranthus japonicus Sieb.,belonging to the Chloranthaceae family,is a perennial herb widely distributed in East Asia,including China,Japan and Korea.Previous phytochemical studies have revealed the presence of a variety of secondary metabolites,such as terpenoids,phenylpropanoids and phenolic derivatives.Among them,sesquiterpenes and dimers,as the main chemical constituents and research focus in this plant,have a variety of biological activities.This review mainly focuses on the research progress of pharmacological activity of sesquiterpenes in this plant,which will lay the foundation for the development and utilization of its medicinal value in the future.

Chlorajaponins A—Q,Lindenane-Related Sesquiterpenoid Dimers from Chloranthus japonicus and Their Biological Activities

Seventeen undescribed lindenane-related sesquiterpenoid dimers,chlorajaponins A—Q(1—17),and 13 reported analogs(18—30)were isolated from Chloranthus japonicus Sieb.Compound 1 possesses an unprecedented 3/5/7/5/5/6/5/3 fused octacyclic scaffold,featuring a 6(5→4)-abeo-lindenane monomer,while 2 exhibits a 3/5/6/6/5/6/5/3 fused octacyclic scaffold.Their structures were determined through a combination of spectroscopic analyses and X-ray crystallography.Compounds 1,2,and 18 demonstrated significant inhibitory effects on lipid accumulation and effectively reduced the levels of triglycerides and total cholesterol,as well as the levels of aspartate aminotransferase and alanine aminotransferase in a HepG2 cell model.In addition,compounds 1,2,and 18 significantly suppressed the protein expression of the fatty acid synthase(FASN)and the sterol regulatory element-binding protein 1(SREBP1).Moreover,the anti-inflammatory assay showed that compounds 19—22 and 25 inhibited the NO production induced by lipopolysaccharide in RAW 264.7 macrophages with IC50 values of 7.89±0.44,6.25±0.46,2.98±0.29,10.77±0.60,and 3.60±0.28μmol/L.

Spirolindemers A and B,Lindenane Sesquiterpenoid Oligomers Equipped with Oxaspiro[4.5]decane from Chloranthus henryi

Spirolindemers A and B,unprecedented lindenane sesquiterpenoid dimer(1)and trimer(2)equipped with oxaspiro[4.5]decane unit,were discovered from the medicinal plant Chloranthus henryi.Their structures including absolute configurations were achieved by HRMS,NMR,ECD,X-ray diffraction analyses,and quantum chemical calculations.Biogenetically,hetero-and homo-Diels-Alder additions may dominate the formation of oxaspiro[4.5]decane and spiro[4.5]decane skeletons,respectively.Compound 1 showed anti-inflammatory activity by inhibiting the expression of iNOS and COX-2.

Sesquiterpenoids from Chloranthus spicatus （Thunb.） Makino

Two new sesquiterpenoids, namely 1β,4β-dihydroxy-5 α,8β（H）-eudesm-7（11）Z-en-8,12-olide （1） and 1β,4α-dihydroxy-5α,8β（H）-eudesm-7（11）Z-en-8,12-olide （2）, along with six known ones, homalomenol A （3）, oplodiol （4）, 5α,7α（H）-6,8-cycloeudesma-1β,4β-diol （5）, oplopanone （6）, 4β,10α-dihydroxyaromadendrane （7） and spathulenol （8）, were isolated from the aerial part of Chloranthus spicatus （Thunb.） Makino, and their structures were established by spectroscopic methods.

Sesquiterpenoids from Chloranthus spicatus

Five new sesquiterpenoids （1-5）, namely chlospicates A--E （1-5）, along with ten known sesquiterpenoids and three known sesquiterpenoid dimers, were isolated from the whole plant of Chloranthus spicatus. Their struc- tures were elucidated on the basis of spectroscopic data.

Structurally Diverse Sesquiterpenoids from Chloranthus henryi var.hupehensis and Their Anti-inflammatory Activities

In this study,27 new sesquiterpenoids:twenty monomers and seven dimers,with diverse structures,along with one known chlora-japonilide F(25)were isolated from the aerial parts of Chloranthus henryi var.hupehensis.Structurally,chlorahupetolides A(1)and B(2),two eudesmane-type merosesquiterpenoids with an undescribed C18 carbon framework,and chlorahupetene E(18)are the first example of dimers comprising two eudesmane sesquiterpenoids bridged by a four-membered ring in the Chloranthus.Their struc-tures were characterized by nuclear magnetic resonance(NMR),electronic circular dichroism(ECD),and X-ray diffraction analysis.In the RAW264.7 macrophages model of inflammation induced by LPS,compounds 12,18,and 25 significantly reduced NO production in a dose dependent manner and without cytotoxicity.The mRNA expression of COX-2 was considerably inhibited by treatments with compounds 12,18,and 25.

Sesquiterpenoids from the Whole Plants of Chloranthus holostegius and Their Anti-inflammatory Activities

Five new sesquiterpenoids(1-5),chloranholides A-E,along with three known compounds(6-8),were isolated from the whole plants of Chloranthus holostegius.Their structures were elucidated using the spectroscopic methods(IR,UV,HR-ESI-MS,ID and 2D NMR),and their absolute configurations were determined by the X-ray crystallography and ECD calculation.Compounds 1-8 were evaluated for their anti-inflammatory effects on LPS-induced RAW 264.7 macrophage cells.Especially,compound 4 exhibited the most significant anti-inflammatory activity with the secretion levels of TNF-α and IL-6 at 15.52%and 5.98%,respectively,better than that of dexamethasone.

Chlospicenes A and B,cyclopropane cracked lindenane sesquiterpenoid dimers with anti-nonalcoholic steatohepatitis activity from Chloranthus henryi

Guided by MS/MS molecular networks strategy,chlospicenes A and B(1 and 2),the first example of cyclopropane moiety cracked lindenane sesquiterpene Michael addition dimers,along with their biogenetic analogues(3 and 4),were targetedly discovered from the roots of Chloranthus henryi.Their structures including absolute configurations were characterized by NMR,ECD and X-ray diffraction analysis.The plausible biogenic pathway speculation indicated that cyclopropylcarbinyl rearrangement may dominate the key crack of cyclopropane moiety.In addition,compounds 1 and 2 showed significant anti-nonalcoholic steatohepatitis(NASH)activity in free fatty acid(FFA)-induced HepG2 cells by decreasing intracellular lipid accumulation.