Nineteen new cadinane-involving sesquiterpenoid dimers,artemordins A-S(1-—19),together with 13 known SDs(20-32)were isolated from Artemisia ordosica.Their structures and absolute configurations were established by co...Nineteen new cadinane-involving sesquiterpenoid dimers,artemordins A-S(1-—19),together with 13 known SDs(20-32)were isolated from Artemisia ordosica.Their structures and absolute configurations were established by comprehensive spectral analyses,X-ray single crystal diffraction,theoretical ECD,and NMR calculations.Chemically,artemordins A-F(1—6)were the first examples of two cadinane units constructed by unprecedented C-3−C-15′or C-3−C-13′single bond with an oxido-rearranged 6/5/6/6 fused ring system;artemordins G-K(7-11)were biogenetically connected by[4+2]cycloaddition reaction and artemordins G-J(7-10)possessed a novel 5/6/6/6/6/6/5-heptacyclic fused ring system.Artemordins L-S(12-19)were formed by esterification,which involved three different types of sesquiterpenoids.Antihepatoma assay suggested that the most active compounds,artemordins B and H(2 and 8),exhibited inhibitory activities on three hepatoma cell lines with IC50 values of 26.9 and 25.1μmol/L(HepG2),29.5 and 18.3μmol/L(Huh7),19.7 and 15.7μmol/L(SK-Hep-1).展开更多
Sarcandra glabra(Thunb.)Nakai is a perennial evergreen herb categorised within the Sarcandra Gardner genus under the Chloranthaceae family.Indigenous to tropical and subtropical regions of East Asia and India,this spe...Sarcandra glabra(Thunb.)Nakai is a perennial evergreen herb categorised within the Sarcandra Gardner genus under the Chloranthaceae family.Indigenous to tropical and subtropical regions of East Asia and India,this species is extensively distributed across China,particularly in the southern regions(Sichuan,Yunnan,and Jiangxi).In addition to its high ornamental value,S.glabra has a rich history of use in traditional Chinese medicine,evident through its empirical prescriptions for various ailments like pneumonia,dysentery,fractures,bruises,numbness,amenorrhea,rheumatism,and other diseases.Besides,modern pharmacological studies have revealed various biological activities,such as antitumour,anti-bacterial,anti-viral anti-inflammatory and immunomodulatory effects.The diverse chemical constituents of S.glabra have fascinated natural product researchers since the 1900s.To date,over 400 compounds including terpenoids,coumarins,lignans,flavonoids,sterols,anthraquinones,organic acids,and organic esters have been isolated and characterised,some featuring unprecedented structures.This review comprehensively examines the current understanding of S.glabra’s phytochemistry and pharmacology,with emphasis on the chemistry and biosynthesis of its unique chemotaxonomic marker,the lindenane-type sesquiterpenoids.展开更多
A pair of new tetrahydrofuran lignan enantiomers,(±)-schibiculatin A[(±)-1],a new enedione lignan,schibiculatin B(2),two new cadinane-type sesquiterpenoids,schibiculatins C(3)and D(4),along with two known se...A pair of new tetrahydrofuran lignan enantiomers,(±)-schibiculatin A[(±)-1],a new enedione lignan,schibiculatin B(2),two new cadinane-type sesquiterpenoids,schibiculatins C(3)and D(4),along with two known seco-cadinane-type sesquiterpenoids(5 and 6)and seven known miscellaneous lignans(7-13)were isolated from the stems of Schisandra bicolor var.tuberculata.The structures of 1-4 were elucidated by comprehensive analysis of their spectro-scopic data,quantum chemical calculations,as well as single-crystal X-ray diffraction.A few isolated compounds were tested for their protective activities against corticosterone-induced apoptosis in PC12 cells.Among them,compounds 5 and 6 showed moderate activities.展开更多
new aristolane sesquiterpenoid named rulepidol was isolated from the fruiting body of Russula lepida Fr. Its structure was elucidated as (1a alpha ,5 alpha ,7 alpha ,7a alpha, 7b alpha)-1, 1a,4,5,6,7,7a, 7b-octahydro-...new aristolane sesquiterpenoid named rulepidol was isolated from the fruiting body of Russula lepida Fr. Its structure was elucidated as (1a alpha ,5 alpha ,7 alpha ,7a alpha, 7b alpha)-1, 1a,4,5,6,7,7a, 7b-octahydro-5-hydroxy-1,1,7,7a-tetramethyl-5H-cyclopropa [alpha] naphthalen-2-one mainly by 1D and 2D-NMR techniques.展开更多
The carbon-13 nuclear magnetic resonance spectra of seventeen protoilludane ses- quiterpenoid aromatic esters from the artificially cultured mycelium of Armillaria mellea (Vahl.ex Fr.) Quel.have been analysed and assi...The carbon-13 nuclear magnetic resonance spectra of seventeen protoilludane ses- quiterpenoid aromatic esters from the artificially cultured mycelium of Armillaria mellea (Vahl.ex Fr.) Quel.have been analysed and assigned.All the ^(11)CNMR signals of the model compounds melleolide 5 and compounds 8,10,11,13,14,15,and 16 can be assigned on the basis of the multiplicity of the sig- nals in the off-resonance decoupled spectra or INEPT spectra.^(11)C-~1H COSY and long-range ^(13)C-~1H COSY.The assignments of the ^(13)CNMR spectra of other protoilludane sesquiterpenoid aromatic esters were completed by comparison with the model compounds as well as the electronic effects of substi- tuted group on the molecules.The present results indicate that ^(11)CNMR spectroscopy provides an ef- fective method for characterizing the protoilludane sesquiterpenoid aromatic esters.展开更多
A new eremophilane sesquiterpenoid, along with two known ones, was isolated from the ethyl acetate soluble fraction of the aerial part of Coleus xanthanthus C. Y. Wu et Y. C. Huang. Their structures were elucidate...A new eremophilane sesquiterpenoid, along with two known ones, was isolated from the ethyl acetate soluble fraction of the aerial part of Coleus xanthanthus C. Y. Wu et Y. C. Huang. Their structures were elucidated as 4,5,11_trimethyl_8,9_seco_1(10),7(11)_eremophiladien_8,12_olid_9_oic acid (1), 2,9_dioxoeuryopsin (2) and 9_oxoeuryopsin (3) by spectral methods. The 1H_NMR and 13 C NMR data of compounds 1, 2 and 3 were unambiguously assigned on the basis of two_dimensional NMR spectroscopy.展开更多
基金This work was financially supported by the Key Program of National Natural Science Foundation of China(22137008)the Xingdian Yingcai Project(YNWR-KJLJ-2019-002)+4 种基金the Youth Innovation Promotion Association,CAS(2020386)the Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province(202105AC160021)the High-Level Talent Program of Yunnan Province(YNQR-QNRC-2020-125)the Science and Technology Plan Projects in Yunnan Province(202201AT070143)State Key Laboratory of Phytochemistry and Plant Resources in West China(P2021-ZZ06).
文摘Nineteen new cadinane-involving sesquiterpenoid dimers,artemordins A-S(1-—19),together with 13 known SDs(20-32)were isolated from Artemisia ordosica.Their structures and absolute configurations were established by comprehensive spectral analyses,X-ray single crystal diffraction,theoretical ECD,and NMR calculations.Chemically,artemordins A-F(1—6)were the first examples of two cadinane units constructed by unprecedented C-3−C-15′or C-3−C-13′single bond with an oxido-rearranged 6/5/6/6 fused ring system;artemordins G-K(7-11)were biogenetically connected by[4+2]cycloaddition reaction and artemordins G-J(7-10)possessed a novel 5/6/6/6/6/6/5-heptacyclic fused ring system.Artemordins L-S(12-19)were formed by esterification,which involved three different types of sesquiterpenoids.Antihepatoma assay suggested that the most active compounds,artemordins B and H(2 and 8),exhibited inhibitory activities on three hepatoma cell lines with IC50 values of 26.9 and 25.1μmol/L(HepG2),29.5 and 18.3μmol/L(Huh7),19.7 and 15.7μmol/L(SK-Hep-1).
文摘Sarcandra glabra(Thunb.)Nakai is a perennial evergreen herb categorised within the Sarcandra Gardner genus under the Chloranthaceae family.Indigenous to tropical and subtropical regions of East Asia and India,this species is extensively distributed across China,particularly in the southern regions(Sichuan,Yunnan,and Jiangxi).In addition to its high ornamental value,S.glabra has a rich history of use in traditional Chinese medicine,evident through its empirical prescriptions for various ailments like pneumonia,dysentery,fractures,bruises,numbness,amenorrhea,rheumatism,and other diseases.Besides,modern pharmacological studies have revealed various biological activities,such as antitumour,anti-bacterial,anti-viral anti-inflammatory and immunomodulatory effects.The diverse chemical constituents of S.glabra have fascinated natural product researchers since the 1900s.To date,over 400 compounds including terpenoids,coumarins,lignans,flavonoids,sterols,anthraquinones,organic acids,and organic esters have been isolated and characterised,some featuring unprecedented structures.This review comprehensively examines the current understanding of S.glabra’s phytochemistry and pharmacology,with emphasis on the chemistry and biosynthesis of its unique chemotaxonomic marker,the lindenane-type sesquiterpenoids.
基金supported financially by the National Natural Science Foundation of China (No.81903520).
文摘A pair of new tetrahydrofuran lignan enantiomers,(±)-schibiculatin A[(±)-1],a new enedione lignan,schibiculatin B(2),two new cadinane-type sesquiterpenoids,schibiculatins C(3)and D(4),along with two known seco-cadinane-type sesquiterpenoids(5 and 6)and seven known miscellaneous lignans(7-13)were isolated from the stems of Schisandra bicolor var.tuberculata.The structures of 1-4 were elucidated by comprehensive analysis of their spectro-scopic data,quantum chemical calculations,as well as single-crystal X-ray diffraction.A few isolated compounds were tested for their protective activities against corticosterone-induced apoptosis in PC12 cells.Among them,compounds 5 and 6 showed moderate activities.
文摘new aristolane sesquiterpenoid named rulepidol was isolated from the fruiting body of Russula lepida Fr. Its structure was elucidated as (1a alpha ,5 alpha ,7 alpha ,7a alpha, 7b alpha)-1, 1a,4,5,6,7,7a, 7b-octahydro-5-hydroxy-1,1,7,7a-tetramethyl-5H-cyclopropa [alpha] naphthalen-2-one mainly by 1D and 2D-NMR techniques.
文摘The carbon-13 nuclear magnetic resonance spectra of seventeen protoilludane ses- quiterpenoid aromatic esters from the artificially cultured mycelium of Armillaria mellea (Vahl.ex Fr.) Quel.have been analysed and assigned.All the ^(11)CNMR signals of the model compounds melleolide 5 and compounds 8,10,11,13,14,15,and 16 can be assigned on the basis of the multiplicity of the sig- nals in the off-resonance decoupled spectra or INEPT spectra.^(11)C-~1H COSY and long-range ^(13)C-~1H COSY.The assignments of the ^(13)CNMR spectra of other protoilludane sesquiterpenoid aromatic esters were completed by comparison with the model compounds as well as the electronic effects of substi- tuted group on the molecules.The present results indicate that ^(11)CNMR spectroscopy provides an ef- fective method for characterizing the protoilludane sesquiterpenoid aromatic esters.
文摘A new eremophilane sesquiterpenoid, along with two known ones, was isolated from the ethyl acetate soluble fraction of the aerial part of Coleus xanthanthus C. Y. Wu et Y. C. Huang. Their structures were elucidated as 4,5,11_trimethyl_8,9_seco_1(10),7(11)_eremophiladien_8,12_olid_9_oic acid (1), 2,9_dioxoeuryopsin (2) and 9_oxoeuryopsin (3) by spectral methods. The 1H_NMR and 13 C NMR data of compounds 1, 2 and 3 were unambiguously assigned on the basis of two_dimensional NMR spectroscopy.
