Two new cyclic diarylheptanoids juglanin A (1) and juglanin B (2) were isolated from the pericarps of Juglans regia L. Their structures were elucidated by various spectroscopic methods including 2D NMR techniques ...Two new cyclic diarylheptanoids juglanin A (1) and juglanin B (2) were isolated from the pericarps of Juglans regia L. Their structures were elucidated by various spectroscopic methods including 2D NMR techniques (COSY, HMQC, HMBC, NOESY) and HR-ESIMS.展开更多
OBJECTIVE: To test if myricanone (02H2405), a cyclic diarylheptanoid, has anticancer effects on two different cancer cell lines HeLa and PC3. The present study was conducted with a note on the drug-DNA interaction ...OBJECTIVE: To test if myricanone (02H2405), a cyclic diarylheptanoid, has anticancer effects on two different cancer cell lines HeLa and PC3. The present study was conducted with a note on the drug-DNA interaction and apoptotic signalling pathway. METHODS: Several studies like cytotoxicity, nuclear damage, annexin-V-fluorescein isothiocyanate (FITC)/propidium iodide (PI)-Iabelled apoptotic assay and cell cycle arrest, immunoblot and reverse transcriptase-polymerase chain reaction (RT-PCR) were used following standard protocols. Circular dichroism (CD) spectroscopy was also done to evaluate whether myricanone effectively interacted with DNA to bring about conformational changes that could strongly inhibit the cancer cell proliferation. RESULTS: Myricanone showed a greater cytotoxic effect on PC3 cells than on HeLa cells. Myricanone promoted G0/G arrest in HeLa cells and S phase arrest in PC3 cells. Nuclear condensation and annexin V-FITC/PI studies revealed that myricanone promoted apoptotic cell death. CD spectroscopic data indicated that myricanone had an interaction with calf thymus DNA that changed DNA structural conformation. RT-PCR and immunoblot studies revealed that myricanone activated the apoptotic signalling cascades through down-regulation of transcription factors like nuclear factor-KB (NF-KB) (p65), and signal transducers and activators of transcription 3 (STAT3); cell cycle regulators like cyclin D1, and survivin and other signal proteins like Bcl-2 and up-regulation of Bax, caspase-9 and caspase-3. CONCLUSION: Myricanone induced apoptosis in both types of cancer cells by triggering caspase activation, and suppression of cell proliferation by down-regulation of NF-KB and STAT3 signalling cascades, which makes it a suitable candidate for possible use in the formulation of therapeutic alent for combatin cancer.展开更多
Pterocarine (1), a new diarylheptanoidal compound, was isolated from Pterocaryatonkinesis (Franch.) Dode. together with a known diarylheptanoid, myricatomentogenin (2), througha bioassay-guided fractionation procedure...Pterocarine (1), a new diarylheptanoidal compound, was isolated from Pterocaryatonkinesis (Franch.) Dode. together with a known diarylheptanoid, myricatomentogenin (2), througha bioassay-guided fractionation procedure. The structure of 1 was elucidated as (+)-3', 4''-epoxy-1-(4'-hydroxyphenyl)-7-(3''-hydroxyphenyl)-heptane-3-one by the spectroscopic methods.Pterocarine (1) inhibited the proliferation of tsFT210, HCT-15 and K562 cells with the inhibitionrates of 20.2±2.4, 23.8±2.4 and 50.5±1.2% at 100 μg/mL, respectively. Flow cytometric analysisindicated that 1 could inhibit the cell cycle of tsFT210, HCT-15 and K562 cells at the G0/G1 phaseand could also induce apoptosis in HCT-15 (19%) and K562 (11%) cells.展开更多
Two new diaryheptanoids, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3- heptanone (1) and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane (2) were isolated from the rhizomes of Zingiber officina...Two new diaryheptanoids, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3- heptanone (1) and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane (2) were isolated from the rhizomes of Zingiber officinale. Their structures were elucidated by spectral methods.展开更多
A new diarylheptanoid glycoside, 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane- 3-O-β-D-xylopyranoside (1), together with nine known diarylheptanoids (2-10) were isolated from the fresh bark of Alnus japonica ...A new diarylheptanoid glycoside, 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane- 3-O-β-D-xylopyranoside (1), together with nine known diarylheptanoids (2-10) were isolated from the fresh bark of Alnus japonica which is a species of the genus Alnus species, growing throughout Korea.展开更多
Eight new diarylheptanoids,coriandralpinins A-H(1-8),were isolated from the rhizomes of Alpinia coriandriodora,an edible plant of the ginger family.Their structures,including the absolute configurations,were establish...Eight new diarylheptanoids,coriandralpinins A-H(1-8),were isolated from the rhizomes of Alpinia coriandriodora,an edible plant of the ginger family.Their structures,including the absolute configurations,were established by extensive spectroscopic analysis and ECD calculations.Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units.When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 mac-rophages,all these compounds scavenged reactive oxygen species(ROS)in a concentration-dependent manner.Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells.Six known flavonols,7,4′-di-O-methylkaempferol,7-O-methylquercetin,7,4′-di-O-methylquercetin,7,3′,4′-tri-O-methylquercetin,kaempferol 3-O-β-d-(6-O-α-l-rhamnopyranosyl)glucopyranoside,and 3-O-β-d-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.展开更多
The two new diarylheptanoids, 1,7-bis(4-hydroxyphenyl)-1,4,6 (l) and aecrogenin G (2) were Synthesized starting from 4-hydroxybenzaldehyde (3) and acetone
Diabetes is an urgent health issue characterized by ethnic and regional variations,and is inseparable from the differ-ent dietary habits.It is worthy to note that the incidence of diabetes in Bai nationality has been ...Diabetes is an urgent health issue characterized by ethnic and regional variations,and is inseparable from the differ-ent dietary habits.It is worthy to note that the incidence of diabetes in Bai nationality has been reported to be much lower than Han in China.As a daily vegetable of Bai,the phytochemical and antidiabetic study of Ottelia acuminata var.acuminata had not been carried out.In this study,41 metabolites with diverse diarylheptanoid(six new ones,Otteacumienes A-F),flavone,sesquiterpenoid,coumarin,lignan,polyacetylene,and alkaloid skeletons were charac-terized from O.acuminata var.acuminata.Among them,the racemic nature of 3 was characterized by chiral resolution and calculated ECD methods.The biological study revealed diarylheptanoids showed significantα-glucosidase inhibi-tory activities with 5 as the most effective one(60-fold stronger than acarbose).Molecular docking studies indicated that these structures have different binding cavities with acarbose.This study demonstrated that O.acuminata var.acuminata might correlated with the low incidence diabetes of Bai and the diarylheptanoids may have potential therapeutic value for diabetes mellitus.展开更多
Natural products play a significant role in human health in relation to the prevention and treatment of inflammatory disorders. In this study, we examined the molecular basis of the anti-inflammatory potential of a di...Natural products play a significant role in human health in relation to the prevention and treatment of inflammatory disorders. In this study, we examined the molecular basis of the anti-inflammatory potential of a diarylheptonoid (DAH) isolated from Alpinia officinarum hexane extract (AOHE) with special emphasis on their ability to modulate the nuclear factor-κB (NF-кB) signaling involved in the inflammatory response. Measurement of Nitrite by Griess reaction which revealed the effect of DAH in RAW 264.7 macrophages showed an inhibition in the nitric oxide production through the suppression of inducible nitric oxide synthase (iNOS) gene level expression. NF-кB reporter gene assay suggests inhibition of NF-кB transcriptional activity, thus inhibiting LPS-induced phosphorylation and degradation of IкBα and a downregulation of NF-кB protein expression confirms the immunomodulatory effect of DAH. Furthermore, downregulation in the gene level expression of NF-кB signaling markers such as IL-1β, TNF-α and COX-2 suggests the anti-inflammatory potential of DAH via inhibition of NF-кB activation.展开更多
AIM: To study the chemical constituents of the rhizomes of Alpinia officinarum Hance. METHOD: Compounds were isolated by repeated column chromatography, and their structures were elucidated on the basis of spectral an...AIM: To study the chemical constituents of the rhizomes of Alpinia officinarum Hance. METHOD: Compounds were isolated by repeated column chromatography, and their structures were elucidated on the basis of spectral analysis. The cytotoxic activities of these compounds were evaluated with the T98G and B16F10 cell lines by the MTT assay. RESULTS: A dimeric diarylheptanoid, named alpinin B(1), along with three known diarylheptanoids were obtained, and their structures were identified as alpinin B(1), 1, 7-diphenyl-3,5-heptanedione(2),(4E)-1, 7-diphenylhept-4-en-3-one(3) and(4E)-7-(4-hydroxyphenyl)-1-phenylhept-4-en-3-one(4). CONCLUSION: Compound 1 is a new dimeric diarylheptanoid. The biosynthetic pathway of 1 was speculated to originate from a Michael reaction between compounds 2 and 3. Compound 3 showed cytotoxicity against the human glioblastoma T98G cell line with IC50 of 27 μmol L 1.展开更多
A new diarylheptanoid glucoside,(8R,9R)-17-methoxy-2-oxatricyclo[13.2.2.1^(3.7)]icosa-l(17),3(20),4,6, 15,18-hexaene-4,9,10-triol-9-O-β-D-glucopyranoside(1),namely jugcathayenoside,together with two known d...A new diarylheptanoid glucoside,(8R,9R)-17-methoxy-2-oxatricyclo[13.2.2.1^(3.7)]icosa-l(17),3(20),4,6, 15,18-hexaene-4,9,10-triol-9-O-β-D-glucopyranoside(1),namely jugcathayenoside,together with two known diarylheptanoids,(+)-galeon(2) and 4-hydroxy-17-methoxy-2-oxatricyclo[13.2.2.1^(3,7) ]icosa-1(17),3(20),4,6,15,18-hexaene-9-one(3),were isolated from the root bark of Juglans cathayensis. Their structures were elucidated on the basis of extensive spectroscopic data analysis.展开更多
One new diarylheptanoid, namely (4E,6E)-7-(3,4-dihydroxy-5-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)- hepta-4,6-dien-3-one (1), was isolated from the rhizomes of Zingiber officinale, along with ten known on...One new diarylheptanoid, namely (4E,6E)-7-(3,4-dihydroxy-5-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)- hepta-4,6-dien-3-one (1), was isolated from the rhizomes of Zingiber officinale, along with ten known ones, tetra- hydrocurcumin (2), curcumin (3), 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (4), gingerenone A (5), 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one (6), (E)-1,7-bis(4-hydroxy- 3-methoxyphenyl)hept-1-ene-3,5-dione (7), (E)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hept-l-ene- 3,5-dione (8), shogasulfonic acid A (9), 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxy-3- methoxyphenyl)heptane (10), and (3S, SS)-3,5-diacetoxy-1,7-bis(3,4-dihydroxyphenyl)heptane (11). Their structures were elucidated on the basis of spectral evidence and comparisons with literature data. The free radical scavenging activity of 1--11 was evaluated by the 1,l-diphenyl-2-picrylhydrazyl (DPPH) assay. Most of the isolated com- pounds were found to be better antioxidants than the positive control ascorbic acid. These compounds were also evaluated for their cytotoxicity against HeLa and MNK-45 cells using the MTT assay. Our results suggest that com- pounds 3 and 5-8 inhibited HeLa cells, and 3, 5, 7 and 8 inhibited MNK-45 cells. It was found that compound 5 was markedly cytotoxic against HeLa and MNK-45 cell lines with ICs0 values of 6.4 and 7.8 μmol/L, respectively.展开更多
文摘Two new cyclic diarylheptanoids juglanin A (1) and juglanin B (2) were isolated from the pericarps of Juglans regia L. Their structures were elucidated by various spectroscopic methods including 2D NMR techniques (COSY, HMQC, HMBC, NOESY) and HR-ESIMS.
基金partially supported by a grant sanctioned to Prof.A.R.Khuda-Bukhsh,Department of Zoology, University of Kalyani,India,by Boiron Laboratories, Lyon,France
文摘OBJECTIVE: To test if myricanone (02H2405), a cyclic diarylheptanoid, has anticancer effects on two different cancer cell lines HeLa and PC3. The present study was conducted with a note on the drug-DNA interaction and apoptotic signalling pathway. METHODS: Several studies like cytotoxicity, nuclear damage, annexin-V-fluorescein isothiocyanate (FITC)/propidium iodide (PI)-Iabelled apoptotic assay and cell cycle arrest, immunoblot and reverse transcriptase-polymerase chain reaction (RT-PCR) were used following standard protocols. Circular dichroism (CD) spectroscopy was also done to evaluate whether myricanone effectively interacted with DNA to bring about conformational changes that could strongly inhibit the cancer cell proliferation. RESULTS: Myricanone showed a greater cytotoxic effect on PC3 cells than on HeLa cells. Myricanone promoted G0/G arrest in HeLa cells and S phase arrest in PC3 cells. Nuclear condensation and annexin V-FITC/PI studies revealed that myricanone promoted apoptotic cell death. CD spectroscopic data indicated that myricanone had an interaction with calf thymus DNA that changed DNA structural conformation. RT-PCR and immunoblot studies revealed that myricanone activated the apoptotic signalling cascades through down-regulation of transcription factors like nuclear factor-KB (NF-KB) (p65), and signal transducers and activators of transcription 3 (STAT3); cell cycle regulators like cyclin D1, and survivin and other signal proteins like Bcl-2 and up-regulation of Bax, caspase-9 and caspase-3. CONCLUSION: Myricanone induced apoptosis in both types of cancer cells by triggering caspase activation, and suppression of cell proliferation by down-regulation of NF-KB and STAT3 signalling cascades, which makes it a suitable candidate for possible use in the formulation of therapeutic alent for combatin cancer.
基金This work was supported by the Fund from the National Natural Science Foundation of China(C.-B.CUI,No.39825126)the Fund for the 973-project from Ministry of Science and Technology(C.-B.CUI,No.1998051113),Chinathe Fund for Cheung Kong Scholar(C.B.CUI)from Cheung Kong Scholars Program,Ministry of Education of China.
文摘Pterocarine (1), a new diarylheptanoidal compound, was isolated from Pterocaryatonkinesis (Franch.) Dode. together with a known diarylheptanoid, myricatomentogenin (2), througha bioassay-guided fractionation procedure. The structure of 1 was elucidated as (+)-3', 4''-epoxy-1-(4'-hydroxyphenyl)-7-(3''-hydroxyphenyl)-heptane-3-one by the spectroscopic methods.Pterocarine (1) inhibited the proliferation of tsFT210, HCT-15 and K562 cells with the inhibitionrates of 20.2±2.4, 23.8±2.4 and 50.5±1.2% at 100 μg/mL, respectively. Flow cytometric analysisindicated that 1 could inhibit the cell cycle of tsFT210, HCT-15 and K562 cells at the G0/G1 phaseand could also induce apoptosis in HCT-15 (19%) and K562 (11%) cells.
文摘Two new diaryheptanoids, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3- heptanone (1) and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane (2) were isolated from the rhizomes of Zingiber officinale. Their structures were elucidated by spectral methods.
文摘A new diarylheptanoid glycoside, 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane- 3-O-β-D-xylopyranoside (1), together with nine known diarylheptanoids (2-10) were isolated from the fresh bark of Alnus japonica which is a species of the genus Alnus species, growing throughout Korea.
基金supported by NSFC Grants(Nos.81172942 and 81872773).
文摘Eight new diarylheptanoids,coriandralpinins A-H(1-8),were isolated from the rhizomes of Alpinia coriandriodora,an edible plant of the ginger family.Their structures,including the absolute configurations,were established by extensive spectroscopic analysis and ECD calculations.Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units.When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 mac-rophages,all these compounds scavenged reactive oxygen species(ROS)in a concentration-dependent manner.Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells.Six known flavonols,7,4′-di-O-methylkaempferol,7-O-methylquercetin,7,4′-di-O-methylquercetin,7,3′,4′-tri-O-methylquercetin,kaempferol 3-O-β-d-(6-O-α-l-rhamnopyranosyl)glucopyranoside,and 3-O-β-d-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.
文摘The two new diarylheptanoids, 1,7-bis(4-hydroxyphenyl)-1,4,6 (l) and aecrogenin G (2) were Synthesized starting from 4-hydroxybenzaldehyde (3) and acetone
基金supported financially by the Second Tibetan Plateau Scientific Expedition and Research program (2019QZKK0502)State Key Laboratory of Phytochemistry and Plant Resources in West China (E0230211Z1 and P2019-ZZ05).
文摘Diabetes is an urgent health issue characterized by ethnic and regional variations,and is inseparable from the differ-ent dietary habits.It is worthy to note that the incidence of diabetes in Bai nationality has been reported to be much lower than Han in China.As a daily vegetable of Bai,the phytochemical and antidiabetic study of Ottelia acuminata var.acuminata had not been carried out.In this study,41 metabolites with diverse diarylheptanoid(six new ones,Otteacumienes A-F),flavone,sesquiterpenoid,coumarin,lignan,polyacetylene,and alkaloid skeletons were charac-terized from O.acuminata var.acuminata.Among them,the racemic nature of 3 was characterized by chiral resolution and calculated ECD methods.The biological study revealed diarylheptanoids showed significantα-glucosidase inhibi-tory activities with 5 as the most effective one(60-fold stronger than acarbose).Molecular docking studies indicated that these structures have different binding cavities with acarbose.This study demonstrated that O.acuminata var.acuminata might correlated with the low incidence diabetes of Bai and the diarylheptanoids may have potential therapeutic value for diabetes mellitus.
文摘Natural products play a significant role in human health in relation to the prevention and treatment of inflammatory disorders. In this study, we examined the molecular basis of the anti-inflammatory potential of a diarylheptonoid (DAH) isolated from Alpinia officinarum hexane extract (AOHE) with special emphasis on their ability to modulate the nuclear factor-κB (NF-кB) signaling involved in the inflammatory response. Measurement of Nitrite by Griess reaction which revealed the effect of DAH in RAW 264.7 macrophages showed an inhibition in the nitric oxide production through the suppression of inducible nitric oxide synthase (iNOS) gene level expression. NF-кB reporter gene assay suggests inhibition of NF-кB transcriptional activity, thus inhibiting LPS-induced phosphorylation and degradation of IкBα and a downregulation of NF-кB protein expression confirms the immunomodulatory effect of DAH. Furthermore, downregulation in the gene level expression of NF-кB signaling markers such as IL-1β, TNF-α and COX-2 suggests the anti-inflammatory potential of DAH via inhibition of NF-кB activation.
基金supported by the Fundamental Research Funds for the Central Universities,China(No.JKY2011015)
文摘AIM: To study the chemical constituents of the rhizomes of Alpinia officinarum Hance. METHOD: Compounds were isolated by repeated column chromatography, and their structures were elucidated on the basis of spectral analysis. The cytotoxic activities of these compounds were evaluated with the T98G and B16F10 cell lines by the MTT assay. RESULTS: A dimeric diarylheptanoid, named alpinin B(1), along with three known diarylheptanoids were obtained, and their structures were identified as alpinin B(1), 1, 7-diphenyl-3,5-heptanedione(2),(4E)-1, 7-diphenylhept-4-en-3-one(3) and(4E)-7-(4-hydroxyphenyl)-1-phenylhept-4-en-3-one(4). CONCLUSION: Compound 1 is a new dimeric diarylheptanoid. The biosynthetic pathway of 1 was speculated to originate from a Michael reaction between compounds 2 and 3. Compound 3 showed cytotoxicity against the human glioblastoma T98G cell line with IC50 of 27 μmol L 1.
基金Financial support from the Natural Science Foundation of China (Nos.30873361,81072547 and 31270394)Wuhan Program for Science and Technology(No.2013060501010158)the Ministry of Science and Technology of the People's Republic of China (International Cooperative Project,No.2010DFA32430)
文摘A new diarylheptanoid glucoside,(8R,9R)-17-methoxy-2-oxatricyclo[13.2.2.1^(3.7)]icosa-l(17),3(20),4,6, 15,18-hexaene-4,9,10-triol-9-O-β-D-glucopyranoside(1),namely jugcathayenoside,together with two known diarylheptanoids,(+)-galeon(2) and 4-hydroxy-17-methoxy-2-oxatricyclo[13.2.2.1^(3,7) ]icosa-1(17),3(20),4,6,15,18-hexaene-9-one(3),were isolated from the root bark of Juglans cathayensis. Their structures were elucidated on the basis of extensive spectroscopic data analysis.
文摘One new diarylheptanoid, namely (4E,6E)-7-(3,4-dihydroxy-5-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)- hepta-4,6-dien-3-one (1), was isolated from the rhizomes of Zingiber officinale, along with ten known ones, tetra- hydrocurcumin (2), curcumin (3), 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (4), gingerenone A (5), 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one (6), (E)-1,7-bis(4-hydroxy- 3-methoxyphenyl)hept-1-ene-3,5-dione (7), (E)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hept-l-ene- 3,5-dione (8), shogasulfonic acid A (9), 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxy-3- methoxyphenyl)heptane (10), and (3S, SS)-3,5-diacetoxy-1,7-bis(3,4-dihydroxyphenyl)heptane (11). Their structures were elucidated on the basis of spectral evidence and comparisons with literature data. The free radical scavenging activity of 1--11 was evaluated by the 1,l-diphenyl-2-picrylhydrazyl (DPPH) assay. Most of the isolated com- pounds were found to be better antioxidants than the positive control ascorbic acid. These compounds were also evaluated for their cytotoxicity against HeLa and MNK-45 cells using the MTT assay. Our results suggest that com- pounds 3 and 5-8 inhibited HeLa cells, and 3, 5, 7 and 8 inhibited MNK-45 cells. It was found that compound 5 was markedly cytotoxic against HeLa and MNK-45 cell lines with ICs0 values of 6.4 and 7.8 μmol/L, respectively.