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...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.展开更多
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 stru...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.展开更多
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 absolut...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.展开更多
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...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.展开更多
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/...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.展开更多
Two lindenane-type sesquiterpene(LDS)trimers with unprecedented carbon skeletons,holotrichones A(1)and B(2),were obtained from the whole plant of Chloranthus holostegius var.trichoneurus by a ultra performance liquid ...Two lindenane-type sesquiterpene(LDS)trimers with unprecedented carbon skeletons,holotrichones A(1)and B(2),were obtained from the whole plant of Chloranthus holostegius var.trichoneurus by a ultra performance liquid chromatography-photodiode array detector-mass spectrometry(UPLC-PDA-MS)-guided isolation strategy.Compound 1 represents the first LDS trimer incorporating a unique 3/5/6/6-fused framework,in which a lindenane-type monomer and the 2-methylbutyryl substituent of an LDS dimer is bridged by a six-membered ring system.Compound 2 is the first hetero-trimer fused by an LDS dimer with a p-benzoquinone-meroterpenoid,featuring an unusual 3/5/6/6/3/5/6/6/6 nonacyclic system fused by the sesquiterpenoid unit and a 2-geranyl-6-methyl-2,5-cyclohexadien-1,4-dione moiety.In compound 2,the dimeric LDS moiety is equipped with a rare oxaspiro[4.5]decane system.Their structures,including absolute configurations,were established by spectroscopic methods,GIAO NMR calculations and DP4+probability analyses,electronic circular dichroism(ECD)calculations,and single-crystal X-ray diffraction analysis.The plausible biogenetic pathway speculation indicated that hetero-and homo-DielsAlder additions may dominate the formation of these highly fused polycyclic frameworks.Both compounds 1 and 2 induced the human acute myeloid leukemia MV-4–11 cell death via apoptosis induction,which deserves further investigation on this new chemical class of LDS oligomers for their anti-leukemic potential.展开更多
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 b...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.展开更多
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.Struc...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.展开更多
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 t...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.展开更多
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(I...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.展开更多
文摘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.
文摘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.
基金The authors acknowledge supports from the National Natural Science Foundation of China(No.32070389)the"Double First-Class"University project(CPU2018GY08).
文摘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.
基金the National Natural Science Foundation of China(No.20462004) for financial support
文摘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.
基金supported by the National Natural Science Foundation of China(Nos.22177044 and 22077058)The computational resources of this work were supported by the Supercomputing Center of Lanzhou University(China).
文摘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.
基金supported by grants from the National Natural Science Foundation of China(Nos.21772025,21937002)。
文摘Two lindenane-type sesquiterpene(LDS)trimers with unprecedented carbon skeletons,holotrichones A(1)and B(2),were obtained from the whole plant of Chloranthus holostegius var.trichoneurus by a ultra performance liquid chromatography-photodiode array detector-mass spectrometry(UPLC-PDA-MS)-guided isolation strategy.Compound 1 represents the first LDS trimer incorporating a unique 3/5/6/6-fused framework,in which a lindenane-type monomer and the 2-methylbutyryl substituent of an LDS dimer is bridged by a six-membered ring system.Compound 2 is the first hetero-trimer fused by an LDS dimer with a p-benzoquinone-meroterpenoid,featuring an unusual 3/5/6/6/3/5/6/6/6 nonacyclic system fused by the sesquiterpenoid unit and a 2-geranyl-6-methyl-2,5-cyclohexadien-1,4-dione moiety.In compound 2,the dimeric LDS moiety is equipped with a rare oxaspiro[4.5]decane system.Their structures,including absolute configurations,were established by spectroscopic methods,GIAO NMR calculations and DP4+probability analyses,electronic circular dichroism(ECD)calculations,and single-crystal X-ray diffraction analysis.The plausible biogenetic pathway speculation indicated that hetero-and homo-DielsAlder additions may dominate the formation of these highly fused polycyclic frameworks.Both compounds 1 and 2 induced the human acute myeloid leukemia MV-4–11 cell death via apoptosis induction,which deserves further investigation on this new chemical class of LDS oligomers for their anti-leukemic potential.
文摘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.
基金supported by grants from the Natural Science Foundation of Hebei Province(Program No.H2022209046)Nanjing Special Fund of Traditional Chinese Medicine(Program No.ZYYB202203)the Natural Science Foundation of Hebei Province(Program No.H2022209053).
文摘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.
文摘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.
基金the National Key R&D Program of China(No.2017YFC1703800)the National Natural Science Foundation of China(Nos.81973190,81803376)+3 种基金the Guangdong Basic and Applied Basic Research Foundation(No.2020B1515020033)the Natural Science Foundation of Guangdong Province(No.2018B030311020)the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(No.2017BT01Y036)the high performance public computing service platform of Jinan University.
文摘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.
