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)...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.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
Comprehensive Summary Alternative synthetic routes toward the tricyclic core of lindenane sesquiterpenoid are presented herein.The route A features an asymmetric organocatalysis enabling desymmetric silylation of diol...Comprehensive Summary Alternative synthetic routes toward the tricyclic core of lindenane sesquiterpenoid are presented herein.The route A features an asymmetric organocatalysis enabling desymmetric silylation of diol to establish the desired tertiary alcohol,while the route B consists of an acetate ring opening of chiral epoxy moiety.The common intermediate(16)in both routes can give rise to the core of lindenane sesquiterpenoid via an intramolecular cyclopropanation.展开更多
基金supports from the National Natural Science Foundation of China(No.32070389)the“Double First-Class”University Project(No.CPU2018GY08)。
文摘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.
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.
文摘Comprehensive Summary Alternative synthetic routes toward the tricyclic core of lindenane sesquiterpenoid are presented herein.The route A features an asymmetric organocatalysis enabling desymmetric silylation of diol to establish the desired tertiary alcohol,while the route B consists of an acetate ring opening of chiral epoxy moiety.The common intermediate(16)in both routes can give rise to the core of lindenane sesquiterpenoid via an intramolecular cyclopropanation.
