Three new sesquiterpene glycosides,named codonopsesquilosides A C(1 3),were isolated from an aqueous extract of the dried roots of Codonopsis pilosula.Their structures including absolute configurations were determined...Three new sesquiterpene glycosides,named codonopsesquilosides A C(1 3),were isolated from an aqueous extract of the dried roots of Codonopsis pilosula.Their structures including absolute configurations were determined by spectroscopic and chemical methods.These glycosides are categorized as C_(15) carotenoid(1),gymnomitrane(2),and eudesmane(3)types of sesquiterpenoids,respectively.Compound 1 is the first diglycoside of C_(15) carotenoids to be reported.Compound 2 represents the second reported example of gymnomitrane-type sesquiterpenoids from higher plants.The absolute configurations were supported by comparison of the experimental circular dichroism(CD)spectra with the calculated electronic CD(ECD)spectra of 13,their aglycones,and model compounds based on quantummechanical time-dependent density functional theory.The influences of the glycosyls on the calculated ECD spectra of the glycosidic sesquiterpenoids,as well as some nomenclature and descriptive problems with gymnomitrane-type sesquiterpenoids are discussed.展开更多
Three eudesmane sesquiterpene lactones, namely artemivestinolides A-C （1-3）, along with three known 11-epimeric lactones （4-6）, were isolated from the aerial parts ofArtemisia vestim. Their structures were elucida...Three eudesmane sesquiterpene lactones, namely artemivestinolides A-C （1-3）, along with three known 11-epimeric lactones （4-6）, were isolated from the aerial parts ofArtemisia vestim. Their structures were elucidated on the basis of extensive spectroscopic analyses （IR, HR-ESIMS, 1D NMR and 2D NMR）, and the absolute configurations were determined by single-crystal X-ray diffraction （with copper radiation）. Furthermore, in an in vitro assay, the three new compounds exhibited a moderate inhibition of the lipopolysaccharide （LPS）-induced nitric： oxide （NO） production in BV-2 microglial cells.展开更多
Two new eudesmane sesquiterpene lactones were isolated from the stalk of Lactuca sativa vat anagustata L and their structures were elucidated by means of spectroscopic methods, including 2D NMR （1H-1H COSY, HMBC and ...Two new eudesmane sesquiterpene lactones were isolated from the stalk of Lactuca sativa vat anagustata L and their structures were elucidated by means of spectroscopic methods, including 2D NMR （1H-1H COSY, HMBC and NOESY） as 1β-O-β-D- glucopyranosyl-4α-hydroxyl-5α, 6β, 11βH-eudesma-12, 6α-olide （1） and 1β-hydroxyl-15-O-（p-methoxyphenylacetyl）-5α, 6β, 11 βH-eudesma-3-en- 12, 6a-olide （2）.展开更多
A new furanoeremophilane and a new eudesmane were isolated from the roots of Ligularia veitchiana. Their structures were elucidated as 1b, 10b-epoxy-6b-isobutyryloxy-9-oxo-furanoeremophilane and 8a-hydroxy-4 (15), 11...A new furanoeremophilane and a new eudesmane were isolated from the roots of Ligularia veitchiana. Their structures were elucidated as 1b, 10b-epoxy-6b-isobutyryloxy-9-oxo-furanoeremophilane and 8a-hydroxy-4 (15), 11-eudesmadiene by spectroscopic methods.展开更多
A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including 12-hydroxy-α-cyperone（1）, 1β,6α-dihydroxyeudesma-4（15）-en...A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including 12-hydroxy-α-cyperone（1）, 1β,6α-dihydroxyeudesma-4（15）-ene（2）, carainterol A（3）, oplodiol（4）, douglanin（5）, 1α-hydroxyisodauc-4-en-15-al（6）, 3α,6α-dihydroxybisabola-4,10-diene（7）, 4α,5β-dihydroxybisabola-2,10-diene（8）, opposit-4（15）-ene-1β,7-diol（9）, and saniculamoid D（10）, respectively. Their structures were elucidated by analysis of the MS and NMR spectroscopic data and comparison with the literature. All the isolates were obtained from A. giraldii var. longipedunculata for the first time, and five of them were obtained from the genus Artemisia for the first time. Additionally, the 13 C NMR data of 1 were fully assigned based on the 2 D NMR data for the first time.展开更多
A facile and efficient diastereoselective synthesis of methyl 3β-hydroxyeudesmane-4,11(13)-dien-12-oicate starting from (+)-dihydrocarvone has been carried out in 9 steps at the first time.
Two new eudesmane derivatives were isolated from the leaves and flowers of Verbesina virginica,along with the known 6-O-β-E -p-coumaroyl-4α-hydroxyeudesmane(1).Their structures were determined as 6-O-β-Z-p-coumaroy...Two new eudesmane derivatives were isolated from the leaves and flowers of Verbesina virginica,along with the known 6-O-β-E -p-coumaroyl-4α-hydroxyeudesmane(1).Their structures were determined as 6-O-β-Z-p-coumaroyl-4α-hydroxyeudesmane(2) and 6-O-α-E-p-coumaroyl-1β-4α-dihydroxyeudesmane(3) by spectroscopic methods.展开更多
A new eudesmane sesquiterpene glycoside, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-4（15）-ene-6-O-β-D-glucopyranoside （2）, together with a known analogue compound, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-3-ene-6-O-β-D-...A new eudesmane sesquiterpene glycoside, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-4（15）-ene-6-O-β-D-glucopyranoside （2）, together with a known analogue compound, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-3-ene-6-O-β-D-glucopyranoside （1）, were isolated from the roots of Parepigynumfuningense. The structure of 2 was determined by 1D and 2D NMR spectroscopy. Compound 1 was isolated from this plant for the first time.展开更多
A new sesquiterpene: 11,12,13-trihydroxy-4(15),7(8)-eudesmdien-9-one was isolated from Saussurea parviflora. The structure was elucidated on the basis of spectral evidence.
The first total synthesis of natural 6β-cinnamoyloxy-1α-hydroxy-5, 10-bis-epi- eudesm-4-en-3-one （1）, a highly complex natural eudesmane, was described.
基金Financial support from the National Natural Sciences Foundation of China(NNSFC,Grant Nos.30825044 and 20932007)the Program for Changjiang Scholars and Innovative Research Team in University(PCSIRT,Grant No.IRT1007)the National Science and Technology Project of China(Nos.2012ZX09301002-002 and 2011ZX09307-002-01)
文摘Three new sesquiterpene glycosides,named codonopsesquilosides A C(1 3),were isolated from an aqueous extract of the dried roots of Codonopsis pilosula.Their structures including absolute configurations were determined by spectroscopic and chemical methods.These glycosides are categorized as C_(15) carotenoid(1),gymnomitrane(2),and eudesmane(3)types of sesquiterpenoids,respectively.Compound 1 is the first diglycoside of C_(15) carotenoids to be reported.Compound 2 represents the second reported example of gymnomitrane-type sesquiterpenoids from higher plants.The absolute configurations were supported by comparison of the experimental circular dichroism(CD)spectra with the calculated electronic CD(ECD)spectra of 13,their aglycones,and model compounds based on quantummechanical time-dependent density functional theory.The influences of the glycosyls on the calculated ECD spectra of the glycosidic sesquiterpenoids,as well as some nomenclature and descriptive problems with gymnomitrane-type sesquiterpenoids are discussed.
基金financially supported by the grants from the National Natural Science Foundation of China(No.30973629)National Key Technology R&D Program‘‘New Drug Innovation’’of China(Nos.2012ZX09301002-002-002,2012ZX09304-005)
文摘Three eudesmane sesquiterpene lactones, namely artemivestinolides A-C （1-3）, along with three known 11-epimeric lactones （4-6）, were isolated from the aerial parts ofArtemisia vestim. Their structures were elucidated on the basis of extensive spectroscopic analyses （IR, HR-ESIMS, 1D NMR and 2D NMR）, and the absolute configurations were determined by single-crystal X-ray diffraction （with copper radiation）. Furthermore, in an in vitro assay, the three new compounds exhibited a moderate inhibition of the lipopolysaccharide （LPS）-induced nitric： oxide （NO） production in BV-2 microglial cells.
基金financed by the Science Foundation of Zhejiang Sci-Tech University(No.0613266-Y)the Talents Training Foundation of Key Laboratory of Advanced Textile Materials and Manufacturing Technology (Zhejiang Sci-Tech University),Ministry of Education(No.2006QN04)
文摘Two new eudesmane sesquiterpene lactones were isolated from the stalk of Lactuca sativa vat anagustata L and their structures were elucidated by means of spectroscopic methods, including 2D NMR （1H-1H COSY, HMBC and NOESY） as 1β-O-β-D- glucopyranosyl-4α-hydroxyl-5α, 6β, 11βH-eudesma-12, 6α-olide （1） and 1β-hydroxyl-15-O-（p-methoxyphenylacetyl）-5α, 6β, 11 βH-eudesma-3-en- 12, 6a-olide （2）.
基金supported by the National Natural Science Foundation of China(No.29972017)
文摘A new furanoeremophilane and a new eudesmane were isolated from the roots of Ligularia veitchiana. Their structures were elucidated as 1b, 10b-epoxy-6b-isobutyryloxy-9-oxo-furanoeremophilane and 8a-hydroxy-4 (15), 11-eudesmadiene by spectroscopic methods.
基金National Natural Science Foundation of China(NSFC,Grant No.81373294)National Key Technology R&D Program"New Drug Innovation"of China(Grant No.2018ZX09711001-008-003)
文摘A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including 12-hydroxy-α-cyperone（1）, 1β,6α-dihydroxyeudesma-4（15）-ene（2）, carainterol A（3）, oplodiol（4）, douglanin（5）, 1α-hydroxyisodauc-4-en-15-al（6）, 3α,6α-dihydroxybisabola-4,10-diene（7）, 4α,5β-dihydroxybisabola-2,10-diene（8）, opposit-4（15）-ene-1β,7-diol（9）, and saniculamoid D（10）, respectively. Their structures were elucidated by analysis of the MS and NMR spectroscopic data and comparison with the literature. All the isolates were obtained from A. giraldii var. longipedunculata for the first time, and five of them were obtained from the genus Artemisia for the first time. Additionally, the 13 C NMR data of 1 were fully assigned based on the 2 D NMR data for the first time.
文摘A facile and efficient diastereoselective synthesis of methyl 3β-hydroxyeudesmane-4,11(13)-dien-12-oicate starting from (+)-dihydrocarvone has been carried out in 9 steps at the first time.
基金supported by the China Scholarship Council,the United States NIH,NIAID,Division of AIDS(No.AI 27094)the USDA Agricultural Research Service Specific Cooperative Agreement(No.58-6408-2-0009)
文摘Two new eudesmane derivatives were isolated from the leaves and flowers of Verbesina virginica,along with the known 6-O-β-E -p-coumaroyl-4α-hydroxyeudesmane(1).Their structures were determined as 6-O-β-Z-p-coumaroyl-4α-hydroxyeudesmane(2) and 6-O-α-E-p-coumaroyl-1β-4α-dihydroxyeudesmane(3) by spectroscopic methods.
文摘A new eudesmane sesquiterpene glycoside, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-4（15）-ene-6-O-β-D-glucopyranoside （2）, together with a known analogue compound, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-3-ene-6-O-β-D-glucopyranoside （1）, were isolated from the roots of Parepigynumfuningense. The structure of 2 was determined by 1D and 2D NMR spectroscopy. Compound 1 was isolated from this plant for the first time.
基金This work was financed by The NNSFC (No. 29972017) and the FMEC (No. 98073003).
文摘A new sesquiterpene: 11,12,13-trihydroxy-4(15),7(8)-eudesmdien-9-one was isolated from Saussurea parviflora. The structure was elucidated on the basis of spectral evidence.
基金This work was financially supported by the National Natural Science Foundation of China （No 20272021）.
文摘The first total synthesis of natural 6β-cinnamoyloxy-1α-hydroxy-5, 10-bis-epi- eudesm-4-en-3-one （1）, a highly complex natural eudesmane, was described.
