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
The fowers of Chrysanthemum indicum,i.e.Ye-ju-hua recorded in the Chinese Pharmacopoeia,has been widely used in China as an important heat-clearing and detoxifying herb for the treatment of infammation,headache,and ve...The fowers of Chrysanthemum indicum,i.e.Ye-ju-hua recorded in the Chinese Pharmacopoeia,has been widely used in China as an important heat-clearing and detoxifying herb for the treatment of infammation,headache,and vertigo.A phytochemical investigation of this herb has led to the isolation of two new eudesmane sesquiterpenoids,7-epi-eudesm4(15),11(13)-diene-1β,3β-diol(1)and 7-epi-1β-hydroxy-β-eudesmol(2).The molecular structures of these new sesquiterpenoids were established based on the comprehensive spectroscopic analyses,including NMR,MS,and IR,and comparing with the literatures.展开更多
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 facile synthetic route to two seco-eudesmane, 4, 5-dioxo-10-epi-4, 5-seco-γ- eudesmane (1) and 4, 5-dioxo-10-epi-4, 5-seco-γ-eudesmol (2) from (+)-dihydrocarvone has been described. Avoiding expensive reagents, th...A facile synthetic route to two seco-eudesmane, 4, 5-dioxo-10-epi-4, 5-seco-γ- eudesmane (1) and 4, 5-dioxo-10-epi-4, 5-seco-γ-eudesmol (2) from (+)-dihydrocarvone has been described. Avoiding expensive reagents, this highly economic method especially suits for the synthesis of 4, 5-seco-eudesman-type and ophianon-type sesquiterpenes with a double bond at position 11 and 12.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
The first total synthesis of （+）-5α-hydroxy-isopterocarpolone （1）, an oxygenated eudesmane isolated from Chinese folk medicine Artemisia eriopoda, starting from （+）-dihydrocarvone（2） was described. Compound 4...The first total synthesis of （+）-5α-hydroxy-isopterocarpolone （1）, an oxygenated eudesmane isolated from Chinese folk medicine Artemisia eriopoda, starting from （+）-dihydrocarvone（2） was described. Compound 4 was stereoselectively prepared from compound 2 in three steps according to reference-. The treatment of tosylhydrazone 5, which was formed via the reaction of compound 4 and TsNHNH2 catalyzed by BF3-5Et2O, with an excess of n-butyllithium gave triene 6. Oxidation of triene 6 with singlet oxygen afforded the desired endo-peroxide 7 as a single product. Reductive cleavage of peroxide 7 with K2CO3 gave α-rotunol 3, a natural eudesmane firstly isolated in 1969. Hydrolysis of α-rotunol 3 with 10% sulfuric acid afforded （+）-5α-hydroxy-isopterocarpolone （1）. The structures of all the compounds were confirmed by IR, MS and NMR spectra.展开更多
3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity.For the purpose of pharmacological activity ...3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity.For the purpose of pharmacological activity research on natural product 1 and its derivatives,a facile total synthesis of compound 1 starting from(+)-dihydrocarvone(2) was completed in an overall yield of 24%.The structures of all intermediates and product 1 were confirmed via 1H NMR,13C NMR,MS and IR techniques.The NMR data of compound 1 are in agreement with those of natural products.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.
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 National Natural Science Foundation of China(Nos.81673325,81711540311,and 21705156)the International Partnership Program of CAS(No.153631KYSB20160004)+1 种基金Gansu Province Key International S&T Cooperation Project(No.18YF1WA127)CAS Pioneer Hundred Talents Program.
文摘The fowers of Chrysanthemum indicum,i.e.Ye-ju-hua recorded in the Chinese Pharmacopoeia,has been widely used in China as an important heat-clearing and detoxifying herb for the treatment of infammation,headache,and vertigo.A phytochemical investigation of this herb has led to the isolation of two new eudesmane sesquiterpenoids,7-epi-eudesm4(15),11(13)-diene-1β,3β-diol(1)and 7-epi-1β-hydroxy-β-eudesmol(2).The molecular structures of these new sesquiterpenoids were established based on the comprehensive spectroscopic analyses,including NMR,MS,and IR,and comparing with the literatures.
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 financially supported by the National Natural Science Foundation of China(No.20272021).
文摘A facile synthetic route to two seco-eudesmane, 4, 5-dioxo-10-epi-4, 5-seco-γ- eudesmane (1) and 4, 5-dioxo-10-epi-4, 5-seco-γ-eudesmol (2) from (+)-dihydrocarvone has been described. Avoiding expensive reagents, this highly economic method especially suits for the synthesis of 4, 5-seco-eudesman-type and ophianon-type sesquiterpenes with a double bond at position 11 and 12.
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.
文摘The first total synthesis of （+）-5α-hydroxy-isopterocarpolone （1）, an oxygenated eudesmane isolated from Chinese folk medicine Artemisia eriopoda, starting from （+）-dihydrocarvone（2） was described. Compound 4 was stereoselectively prepared from compound 2 in three steps according to reference-. The treatment of tosylhydrazone 5, which was formed via the reaction of compound 4 and TsNHNH2 catalyzed by BF3-5Et2O, with an excess of n-butyllithium gave triene 6. Oxidation of triene 6 with singlet oxygen afforded the desired endo-peroxide 7 as a single product. Reductive cleavage of peroxide 7 with K2CO3 gave α-rotunol 3, a natural eudesmane firstly isolated in 1969. Hydrolysis of α-rotunol 3 with 10% sulfuric acid afforded （+）-5α-hydroxy-isopterocarpolone （1）. The structures of all the compounds were confirmed by IR, MS and NMR spectra.
文摘3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity.For the purpose of pharmacological activity research on natural product 1 and its derivatives,a facile total synthesis of compound 1 starting from(+)-dihydrocarvone(2) was completed in an overall yield of 24%.The structures of all intermediates and product 1 were confirmed via 1H NMR,13C NMR,MS and IR techniques.The NMR data of compound 1 are in agreement with those of natural products.
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.
