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
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
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.
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.
