17 new guaiane-type sesquiterpenoid dimers(GSDs),artemzhongdianolides B1—B17(1—17),were isolated from Artemisia zhongdianensis under the guidance of bioassay,and elucidated by spectral analyses(HRESIMS,1D and 2D NMR...17 new guaiane-type sesquiterpenoid dimers(GSDs),artemzhongdianolides B1—B17(1—17),were isolated from Artemisia zhongdianensis under the guidance of bioassay,and elucidated by spectral analyses(HRESIMS,1D and 2D NMR,IR,ECD).The absolute configuration of compounds 1,3,7,9,10,and 13 was determined by single-crystal X-ray diffraction analyses.Structurally,artemzhongdianolides B1(1)and B2(2)were the first example of the GSDs fused via a C-13/C-13'single bond,and artemzhongdianolides B3—B17 were[4+2]Diels–Alder adducts of two monomeric guaianolides.Most of the compounds showed antihepatoma cytotoxicity with IC_(50) values ranging from 9.9 to 170.1μmol/L.Importantly,artemzhongdianolide B9(9)was the most active one against three hepatoma cell lines with IC_(50) values of 13.1μmol/L(HepG2),19.5μmol/L(Huh7),and 19.5μmol/L(SK-Hep-1),and dose-dependently inhibited cell migration and invasion,induced G1 cell cycle arrest and cell apoptosis in HepG2 cells.Compound 9 might suppress HepG2 cells via affecting the p38MAPK signaling pathway suggested by machine learning approach,and significantly upregulated expression of phosphorylated p38 validated by Western blot assay.展开更多
Four new glycosides including a eudesmane-type sesquiterpenoid（1）, a guaiane-type sesquiterpenoid（2）, and two C_（14）-polyacetylenes（3, 4） were isolated from the rhizomes of Atractylodes lancea. Their structure...Four new glycosides including a eudesmane-type sesquiterpenoid（1）, a guaiane-type sesquiterpenoid（2）, and two C_（14）-polyacetylenes（3, 4） were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses（UV, IR, 1D and 2D NMR, and HR-ESIMS）. The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism（ECD）, whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of10μmmolL^（-1）.展开更多
Eight new guaiane-type sesquiterpenoid trimers,artemsieverolactones A—H,possessing unprecedented scaffolds via biocatalyzed[4+2]Diels−Alder cycloaddition reactions were identified from Artemisia sieversiana.Their str...Eight new guaiane-type sesquiterpenoid trimers,artemsieverolactones A—H,possessing unprecedented scaffolds via biocatalyzed[4+2]Diels−Alder cycloaddition reactions were identified from Artemisia sieversiana.Their structures were determined by comprehensive spectroscopic data,single-crystal X-ray diffraction analyses,and ECD calculations.In terms of structure,artemsieverolactones A—H are first examples of sesquiterpenoid trimers from guaiane-type sesquiterpenoid through four different[4+2]Diels−Alder cycloaddition models.Antihepatic fibrosis assay suggested that five compounds exhibited activity against HSC-LX2 with IC_(50)values ranging from 37.8 to 117.1μmol/L.The most active artemsieverolactone B(2)displayed significant inhibitory activity against HSC-LX2 with IC_(50)value of 37.8μmol/L,which was 3 times more active than the positive drug silybin(IC_(50),139.7μmol/L).Preliminary mechanism study revealed that artemsieverolactone B could inhibit the deposition of human collagen typeⅠ(ColⅠ),human hyaluronic acid(HA),and human laminin(HL)with IC_(50)values of 40.4μmol/L(Col I),55.1μmol/L(HL),47.3μmol/L(HA),which was 2 to 3-fold more potent than silybin.展开更多
A new guaiane-type sesquiterpene, wiksphyllamin A （1） with C-10 and C-11 connected, along with fifteen known compounds were isolated from the stems of Wiks＇troemia scytophylla Diels. All these compounds were iso- l...A new guaiane-type sesquiterpene, wiksphyllamin A （1） with C-10 and C-11 connected, along with fifteen known compounds were isolated from the stems of Wiks＇troemia scytophylla Diels. All these compounds were iso- lated for the first time from Wikstroemia scytophylla. The structures of 1--16 were identified using spectroscopic methods.展开更多
基金supported by the Key Program of National Natural Science Foundation of China(22137008)the Xingdian Yingcai Project(YNWR-KJLJ-2019-002)+1 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).
文摘17 new guaiane-type sesquiterpenoid dimers(GSDs),artemzhongdianolides B1—B17(1—17),were isolated from Artemisia zhongdianensis under the guidance of bioassay,and elucidated by spectral analyses(HRESIMS,1D and 2D NMR,IR,ECD).The absolute configuration of compounds 1,3,7,9,10,and 13 was determined by single-crystal X-ray diffraction analyses.Structurally,artemzhongdianolides B1(1)and B2(2)were the first example of the GSDs fused via a C-13/C-13'single bond,and artemzhongdianolides B3—B17 were[4+2]Diels–Alder adducts of two monomeric guaianolides.Most of the compounds showed antihepatoma cytotoxicity with IC_(50) values ranging from 9.9 to 170.1μmol/L.Importantly,artemzhongdianolide B9(9)was the most active one against three hepatoma cell lines with IC_(50) values of 13.1μmol/L(HepG2),19.5μmol/L(Huh7),and 19.5μmol/L(SK-Hep-1),and dose-dependently inhibited cell migration and invasion,induced G1 cell cycle arrest and cell apoptosis in HepG2 cells.Compound 9 might suppress HepG2 cells via affecting the p38MAPK signaling pathway suggested by machine learning approach,and significantly upregulated expression of phosphorylated p38 validated by Western blot assay.
基金funded by the National Science and Technology Project of China(No.2012ZX09301002-001003)
文摘Four new glycosides including a eudesmane-type sesquiterpenoid（1）, a guaiane-type sesquiterpenoid（2）, and two C_（14）-polyacetylenes（3, 4） were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses（UV, IR, 1D and 2D NMR, and HR-ESIMS）. The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism（ECD）, whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of10μmmolL^（-1）.
基金supported by the Key Program of National Natural Science Foundation of China(22137008)the Xingdian Yingcai Project(YNWR-KJLJ-2019-002)+1 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).
文摘Eight new guaiane-type sesquiterpenoid trimers,artemsieverolactones A—H,possessing unprecedented scaffolds via biocatalyzed[4+2]Diels−Alder cycloaddition reactions were identified from Artemisia sieversiana.Their structures were determined by comprehensive spectroscopic data,single-crystal X-ray diffraction analyses,and ECD calculations.In terms of structure,artemsieverolactones A—H are first examples of sesquiterpenoid trimers from guaiane-type sesquiterpenoid through four different[4+2]Diels−Alder cycloaddition models.Antihepatic fibrosis assay suggested that five compounds exhibited activity against HSC-LX2 with IC_(50)values ranging from 37.8 to 117.1μmol/L.The most active artemsieverolactone B(2)displayed significant inhibitory activity against HSC-LX2 with IC_(50)value of 37.8μmol/L,which was 3 times more active than the positive drug silybin(IC_(50),139.7μmol/L).Preliminary mechanism study revealed that artemsieverolactone B could inhibit the deposition of human collagen typeⅠ(ColⅠ),human hyaluronic acid(HA),and human laminin(HL)with IC_(50)values of 40.4μmol/L(Col I),55.1μmol/L(HL),47.3μmol/L(HA),which was 2 to 3-fold more potent than silybin.
文摘A new guaiane-type sesquiterpene, wiksphyllamin A （1） with C-10 and C-11 connected, along with fifteen known compounds were isolated from the stems of Wiks＇troemia scytophylla Diels. All these compounds were iso- lated for the first time from Wikstroemia scytophylla. The structures of 1--16 were identified using spectroscopic methods.
