150 results on '"Xing-De Wu"'
Search Results
2. Lycoplanines B-D, Three Lycopodium Alkaloids from Lycopodium complanatum
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Zhi-Jun Zhang, Qin-Feng Zhu, Jia Su, Xing-De Wu, and Qin-Shi Zhao
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Lycopodium complanatum ,Lycoplanines ,Lycopodium alkaloids ,Anti-AChE activity ,Botany ,QK1-989 - Abstract
Abstract A novel C17N Lycopodium alkaloid (LA), lycoplanine B (1), containing an unusual formyl group, along with two new LAs, lycoplanines C (2) and D (3), were isolated from the whole plant of Lycopodium complanatum. Their structures were elucidated by extensive NMR techniques, including 1D- and 2D-NMR experiments, as well as comparing their spectral data with those of the known analogues. A possible biogenetic pathway for 1 was also proposed. Graphical Abstract
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- 2018
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3. Monoterpene Indole Alkaloids with Cav3.1 T-Type Calcium Channel Inhibitory Activity from Catharanthus roseus
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Zhen-Tao Deng, Wen-Yan Li, Lei Wang, Zhi-Ping Zhou, Xing-De Wu, Zhong-Tao Ding, and Qin-Shi Zhao
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Catharanthus roseus ,monoterpene indole alkaloid ,catharanosine A ,Cav3.1 low voltage-gated calcium channel (LVGCC) ,Organic chemistry ,QD241-441 - Abstract
Catharanthus roseus is a well-known traditional herbal medicine for the treatment of cancer, hypertension, scald, and sore in China. Phytochemical investigation on the twigs and leaves of this species led to the isolation of two new monoterpene indole alkaloids, catharanosines A (1) and B (2), and six known analogues (3–8). Structures of 1 and 2 were established by 1H-, 13C- and 2D-NMR, and HREIMS data. The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 2 represented an unprecedented aspidosperma-type alkaloid with a 2-piperidinyl moiety at C-10. Compounds 6–8 exhibited remarkable Cav3.1 low voltage-gated calcium channel (LVGCC) inhibitory activity with IC50 values of 11.83 ± 1.02, 14.3 ± 1.20, and 14.54 ± 0.99 μM, respectively.
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- 2021
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4. Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata
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Yu-Chen Liu, Zhi-Jun Zhang, Jia Su, Li-Yan Peng, Lu-Tai Pan, Xing-De Wu, and Qin-Shi Zhao
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Lycopodium alkaloids ,Lycodine-type ,Huperzia serrata ,BACE1 inhibitory activity ,Botany ,QK1-989 - Abstract
Abstract Three new lycodine-type Lycopodium alkaloids, namely 1-methyllycodine (1), 8α-hydroxy-15,16-dehydro-des-N-methyl-α-obscurine (2), N-methyl-16-hydroxyhuperzine B (3), and one new natural lycodine-type Lycopodium alkaloid, N-methylhuperzine A (4), along with 11 known analogues (5–15), were isolated from the whole plants of club moss Huperzia serrata. The structures of 1–4 were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Among them, compound 1 was the first lycodine-type alkaloid possessing a methyl group at C-1. In addition, the structure of 5 was confirmed by the single-crystal X-ray crystallography data and its 13C NMR was reported for the first time in current study. Compounds 1–5 were tested their BACE1 inhibitory activity. Graphical Abstract
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- 2017
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5. Total synthesis of huperserratines A and B
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Zhen-Tao Deng, Xing-De Wu, Zai-Feng Yuan, Nai-Rong Yu, Yu-Fei Ou, and Qin-Shi Zhao
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Organic Chemistry - Abstract
The first total synthesis of two macrocyclic Lycopodium alkaloids, huperserratines A and B, in 12 steps.
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- 2022
6. Hypoestins A–D: highly modified fusicoccane diterpenoids with promising Cav3.1 calcium channel inhibitory activity from Hypoestes purpurea
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Xing-De Wu, Lin-Fen Ding, Wen-Yan Li, Bin Cheng, Tie Lei, Hao-Feng Zhou, and Qin-Shi Zhao
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Organic Chemistry - Abstract
Four highly modified fusicoccane diterpenoids with two unreported carbon skeletons, hypoestins A–D (1–4), were isolated and characterized from Hypoestes purpurea.
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- 2022
7. Biphenyl-type neolignans with NO inhibitory activity from the fruits of Magnolia tripetala
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Zhen-Xiang Liu, Xing-De Wu, Lin-Fen Ding, Jin-Da Li, Tie Lei, Liu-Dong Song, and Wei Nie
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Biphenyl ,biology ,Chemistry ,Stereochemistry ,Dimer ,chemistry.chemical_element ,Plant Science ,Magnolia tripetala ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Ic50 values ,Agronomy and Crop Science ,Carbon ,Two-dimensional nuclear magnetic resonance spectroscopy ,Biotechnology - Abstract
Tripetalins A (1) and B (2), two new biphenyl-type neolignans were obtained from the fruits of Magnolia tripetala, along with four known analogues. The structures of the new compounds were characterized by comprehensive spectroscopic analyses including 1H, 13C, and 2D NMR, IR, and HRESIMS data. Tripetalin A (1) was the first magnolol-honokiol-type neolignan dimer linked through C-5′‒C5′′ carbon bond. Magnoquinone (5) and magnotriol B (6) displayed remarkable NO inhibitory activity with IC50 values of 4.52 ± 0.07 and 2.02 ± 0.03 μM, respectively.
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- 2021
8. Spirocyclohexadienone‐Type Neolignans with Neuroprotective and Neurite Outgrowth Enhancing Activities from Magnolia liliiflora
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Xing‐De Wu, Jian‐Lin Hu, Wei Nie, Ming Hu, Jin‐Da Li, Yi‐Fan Shen, Lin‐Fen Ding, and Liu‐Dong Song
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Neuronal Outgrowth ,Bioengineering ,General Chemistry ,General Medicine ,PC12 Cells ,Biochemistry ,Lignans ,Rats ,Magnolia ,Nerve Growth Factor ,Neurites ,Animals ,Molecular Medicine ,Corticosterone ,Molecular Biology - Abstract
Three rare spirocyclohexadienone-type neolignans, magnoflorins A-C (1-3), and three known analogs (4-6), were isolated from the leaves of Magnolia liliiflora. Magnoflorin D (4) was obtained from natural resources for the first time. The chemical structures and absolute configurations of 1-4 were elucidated through detailed analysis of HR-ESI-MS, IR
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- 2022
9. Four Highly Oxygenated Sesquiterpenoids from the Fruits of Illicium micranthum Dunn
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Tie Lei, Zhen‐Xiang Liu, Yi Bao, Lin‐Fen Ding, Liu‐Dong Song, Xing‐De Wu, and Qin‐Shi Zhao
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Lactones ,Molecular Structure ,Fruit ,Animals ,Molecular Medicine ,Bioengineering ,General Chemistry ,General Medicine ,Sesquiterpenes ,Molecular Biology ,Biochemistry ,Illicium ,Rats - Abstract
Four highly oxygenated sesquiterpenoids, illimicranolides A (1) and B (2), and illicinolides E (3) and F (4), were obtained from the fruits of Illicium micranthum Dunn, as well as one known analog, illicinolide B (5). The chemical structures of 1-4 were determined comprehensively by 1D (
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- 2022
10. Cunlanceloic acids A–D: unprecedented labdane diterpenoid dimers with AChE inhibitory and cytotoxic activities from Cunninghamia lanceolata
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Xiao-Nian Li, Xing-De Wu, Bin Chen, Qin-Shi Zhao, Lin-Fen Ding, and Li-Yan Peng
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biology ,Aché ,Stereochemistry ,Organic Chemistry ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,Peroxide ,Terpenoid ,language.human_language ,Labdane ,chemistry.chemical_compound ,chemistry ,language ,Cytotoxic T cell ,Cunninghamia ,IC50 - Abstract
Cunlanceloic acid A (1), a symmetric terpenoid peroxide bearing an unprecedented dimeric labdane backbone linked through C-16/C-16′ bonds, and cunlanceloic acids B–D (2–4), three asymmetric diterpenoid dimers with a new carbon skeleton linked through C12/C-13′ and C-15/C-16′ bonds between two labdane units, were isolated from the cones of Cunninghamia lanceolata. Their structures including absolute configurations were determined by extensive NMR spectroscopy, X-ray diffraction analysis, and chemical transformations. Compound 1 exhibited potent AChE inhibitory activity with an IC50 value of 6.14 ± 0.66 μM and compounds 2 and 3 showed remarkable cytotoxic activities against A-549 and SMMC-7721 cell lines with IC50 values of 5.90–9.21 μM.
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- 2021
11. Hupertimines A-E, Fawcettimine-Type Lycopodium Alkaloids from Huperzia serrata
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Zhen‐Tao Deng, Yu‐Chen Liu, Qin‐Feng Zhu, Shuai Jiang, Xing‐De Wu, and Qin‐Shi Zhao
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Alkaloids ,Molecular Structure ,Molecular Medicine ,Aspartic Acid Endopeptidases ,Bioengineering ,Huperzia ,General Chemistry ,General Medicine ,Amyloid Precursor Protein Secretases ,Molecular Biology ,Biochemistry ,Lycopodium - Abstract
Five new fawcettimine-type Lycopodium alkaloids, hupertimines A-E (1-5), were discovered from the whole plant of Huperzia serrata, along with two known alkaloids, 8α-hydroxyphlegmariurine B (6) and 8β-hydroxyphlegmariurine B (7). The structures of 1-7 were identified through HR-MS, IR
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- 2022
12. Huperserratines A and B, Two Macrocyclic Lycopodium Alkaloids with an Unusual Skeleton from Huperzia serrata
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Xiao-Nian Li, Qin-Shi Zhao, Li-Yan Peng, and Xing-De Wu
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Lycopodium ,biology ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Huperzia serrata ,Hexadecane ,010402 general chemistry ,Oxime ,Ring (chemistry) ,biology.organism_classification ,01 natural sciences ,Skeleton (computer programming) ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry - Abstract
Huperserratines A (1) and B (2), two Lycopodium alkaloids with an unprecedented 5-aza-bicyclo[10.4.0]hexadecane skeleton and an oxime function, were isolated from Huperzia serrata. Their structures including absolute configurations were determined by extensive NMR spectroscopic and X-ray diffraction analysis. Compounds 1 and 2 were the first examples of macrocyclic Lycopodium alkaloids with an aza-12-membered ring. A plausible biogenetic pathway of these compounds was also proposed. Compound 1 exhibited moderate anti-HIV-1 activity with an EC50 of 52.91 μg/mL and a therapy index greater than 3.78.
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- 2020
13. Spiroligustolides A and B: Two pairs of enantiomeric spiro-orthoester-containing phthalide dimers as Ca
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Liu-Yan, Wang, Wen-Yan, Li, Hao-Feng, Zhou, Xue-Yu, Zhao, Xiao-Nian, Li, Xing-De, Wu, and Qin-Shi, Zhao
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Molecular Structure ,Ligusticum ,Stereoisomerism ,Calcium Channels ,Benzofurans - Abstract
Two pairs of unprecedented enantiomeric phthalide dimers, spiroligustolides A (1a/1b) and B (2a/2b), featuring a unique spiroorthoster linkage between two monomeric units to form a 5/6/5/6/6-fused ring system, were isolated from the roots of Ligusticum chuanxiong. The structures and relative configurations of 1 and 2 were determined by HR-ESI-MS, IR, and NMR spectroscopic data, coupled with single-crystal X-ray diffraction analysis, and the absolute configurations of 1a, 1b, 2a, and 2b were established by comparing the experimental and calculated electronic circular dichroism (ECD) data. Plausible biosynthetic pathway for 1 and 2 was proposed. Moreover, compounds 1, 1b, and 2b showed remarkable inhibitory activities on Ca
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- 2022
14. seco ‐Prezizanne Sesquiterpenes and Prenylated C6‐C3 Compounds from the Fruits of Illicium lanceolatum A. C. Smith
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Tie Lei, Qin-Shi Zhao, Yi Bao, Hao-Feng Zhou, Liu-Dong Song, Xing-De Wu, Zheng-Hong Pan, Lin-Fen Ding, and Wei Nie
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Spectrometry, Mass, Electrospray Ionization ,Circular dichroism ,Magnetic Resonance Spectroscopy ,Illicium lanceolatum ,Cell Survival ,Stereochemistry ,Molecular Conformation ,Bioengineering ,PC12 Cells ,Biochemistry ,Illicium ,Prenylation ,Animals ,Molecular Biology ,Plant Extracts ,Chemistry ,Circular Dichroism ,Absolute configuration ,Data interpretation ,General Chemistry ,General Medicine ,Rats ,Neuroprotective Agents ,Fruit ,Molecular Medicine ,Sesquiterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Two new seco- prezizaane-type sesquiterpenes, 2 β -hydroxy-6-deoxyneoanisatin ( 1 ) and 3,4-anhydro-2-oxo-1 α -hydroxy-6-deoxyneoanisatin ( 2 ), and two new prenylated C 6 -C 3 compounds, illilanceofunones A ( 3 ) and B ( 4 ), were obtained from the fruits of Illicium lanceolatum , along with four known prenylated C 6 -C 3 compounds ( 5-8 ). Their structures were proposed through HRESIMS, 1 H, 13 C, and 2D NMR data interpretation. Moreover, the absolute configuration of 1 and 2 were further assigned by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations, respectively . Illihenryipyranol A ( 6 ) exhibited neuroprotective activity against MPP + -induced PC12 cell damage in a dose-dependent manner .
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- 2021
15. A New Quinolizidine Alkaloid from Sophora flavescens
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Lei, Wang, Xing-De, Wu, Juan, He, Gen-Tao, Li, Li-Yan, Peng, Yan, Li, Liu-Dong, Song, and Qin-Shi, Zhao
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- 2014
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16. Neo ‐clerodane Diterpenoids with Hypoglycemic Effects in Vivo from the Aerial Parts of Salvia hispanica L
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Li-Yan Peng, He-Yao Wang, Ting Wang, Min Fan, Xing-De Wu, Jun-Shang Huang, and Qin-Shi Zhao
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Blood Glucose ,Male ,Models, Molecular ,Salvia hispanica ,Bioengineering ,Pharmacology ,Crystallography, X-Ray ,Biochemistry ,Diabetes Mellitus, Experimental ,Diterpenes, Clerodane ,Mice ,Insulin resistance ,food ,In vivo ,medicine ,Animals ,Hypoglycemic Agents ,Salvia ,Molecular Biology ,Molecular Structure ,Chemistry ,Absolute configuration ,Type 2 Diabetes Mellitus ,General Chemistry ,General Medicine ,Plant Components, Aerial ,medicine.disease ,Terpenoid ,food.food ,Metformin ,Mice, Inbred C57BL ,Disease Models, Animal ,Diabetes Mellitus, Type 2 ,Molecular Medicine ,Two-dimensional nuclear magnetic resonance spectroscopy ,medicine.drug - Abstract
A new neo-clerodane diterpenoid, salvihispin H (1), and six known ones (2-7) were identified from the aerial parts of Salvia hispanica L. The structure and absolute configuration of 1 were elucidated by extensive analysis of spectroscopic (1 H, 13 C, and 2D NMR, and HR-ESI-MS) and single-crystal X-ray diffraction data. The anti-diabetic effects of salvihispin H (1) and salvifaricin (2) were evaluated in diabetic db/db mice. The data showed that 1 and 2 could significantly reduce fasting blood glucose level and improve insulin resistance, and compound 1 exerted glucose-lowering effect more quickly than metformin. In addition, 1 and 2 could also reduce serum TG level in db/db mice. These results demonstrated that compounds 1 and 2 could be considered as potent candidates for the therapy of type 2 diabetes mellitus (T2DM).
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- 2021
17. Cassane diterpenoids from the seeds of Caesalpinia bonduc and their nitric oxide production and α-glucosidase inhibitory activities
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Li-Yan Peng, Wen-Chao Tu, Lin-Fen Ding, Xing-De Wu, Liu-Dong Song, and Qin-Shi Zhao
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Caesalpinia ,Magnetic Resonance Spectroscopy ,biology ,Molecular Structure ,Stereochemistry ,alpha-Glucosidases ,Plant Science ,General Medicine ,Fabaceae ,Horticulture ,biology.organism_classification ,Nitric Oxide ,Biochemistry ,Nitric oxide ,chemistry.chemical_compound ,Caesalpinia bonduc ,chemistry ,Seeds ,Diterpenes ,Molecular Biology ,IC50 ,Two-dimensional nuclear magnetic resonance spectroscopy ,α glucosidase inhibitory - Abstract
Ten previously undescribed cassane diterpenoids, cassabonducins A–J, and eleven known compounds were isolated from the seeds of Caesalpinia bonduc. The structures of the undescribed compounds were elucidated by extensive analysis of spectroscopic data (IR, HRESIMS, and 1H, 13C and 2D NMR) and their absolute configurations were determined by the ECD data and single-crystal X-ray diffraction analysis. e-Caesalpin-Ⅶ was obtained from natural resources for the first time. Cassabonducin A possessed noteworthy inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages with IC50 value of 6.12 μM. Cassabonducin D and neocaesalpin N showed moderate α-glucosidase inhibition at the concentration of 50 μM with inhibitory capacities of 47.17% and 43.83%, respectively.
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- 2021
18. Phlegmadine A: A Lycopodium Alkaloid with a Unique Cyclobutane Ring from Phlegmariurus phlegmaria
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Qin-Shi Zhao, Chen Wang, Zhi-Jun Zhang, Yan Huang, Wen-Xia Zhou, and Xing-De Wu
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010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Molecular conformation ,0104 chemical sciences ,Cyclobutane ,chemistry.chemical_compound ,Biomimetic synthesis ,Lycopodium alkaloid ,Phlegmariurus phlegmaria - Abstract
Phlegmadine A (1), a Lycopodium alkaloid with a unique cyclobutane ring and featuring a complex tetracyclo[4.2.2.03,8.03,10]decane-bridged system, together with three biogenetically related known compounds, was isolated from the Phlegmariurus phlegmaria. The structures and absolute configurations of 1 and 2 were determined by NMR and single-crystal X-ray analysis. Among them, compound 2 exhibited noticeable protective effects for long-term potentiation impairment by corticosterone induced in mice. Moreover, we succeeded in the efficient synthesis of 1 from 3 by a biomimetic synthesis method.
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- 2019
19. Magnograndins J-M, elemane sesquiterpenoids from the leaves of Magnolia grandiflora and their inhibitory effects on nitric oxide production
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Qin-Shi Zhao, Xing-De Wu, Wei Nie, De-Shen Wang, Zhang-Qiao Xie, Lin-Fen Ding, Liu-Dong Song, and Jiangxin Liu
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biology ,010405 organic chemistry ,Stereochemistry ,Plant Science ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Nitric oxide ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Magnolia grandiflora ,chemistry ,Acetone ,Agronomy and Crop Science ,Two-dimensional nuclear magnetic resonance spectroscopy ,Biotechnology - Abstract
Four new elemane sesquiterpenoids, magnograndins J-M (1-4), and one known sesquiterpenoid, 12,13-diacetoxyelema-1,3-dien-6α,11-diol (5), were obtained from 70% acetone extract of the leaves of Magnolia grandiflora. Their structures were determined with extensive spectroscopic (HRMS, IR, 1D and 2D NMR) analyses. Compound 1 represented the first example of elemane sesquiterpenoid with an orthoacetate unit. Compound 4 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC50 value of 17.83 μM.
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- 2019
20. Diterpenoids and sesquiterpenoids from the stem bark of Metasequoia glyptostroboides
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Liu-Dong Song, Li-Yan Peng, Xun Gong, Qin-Shi Zhao, Xing-De Wu, Hui Yang, Yan-Yan Qi, Wen-Chao Tu, Lin-Fen Ding, and Jiangxin Liu
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Models, Molecular ,0106 biological sciences ,Cupressaceae ,Cell Survival ,Stereochemistry ,Chemical structure ,Molecular Conformation ,Plant Science ,Horticulture ,Crystallography, X-Ray ,01 natural sciences ,Biochemistry ,HeLa ,Structure-Activity Relationship ,Cell Line, Tumor ,Humans ,Cytotoxicity ,Molecular Biology ,Cell Proliferation ,Dose-Response Relationship, Drug ,Plant Stems ,biology ,010405 organic chemistry ,Chemistry ,General Medicine ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Terpenoid ,0104 chemical sciences ,Metasequoia glyptostroboides ,Phytochemical ,visual_art ,Plant Bark ,visual_art.visual_art_medium ,Bark ,Diterpenes ,Drug Screening Assays, Antitumor ,Sesquiterpenes ,HeLa Cells ,010606 plant biology & botany - Abstract
A phytochemical study on the stem bark of Metasequoia glyptostroboides led to the isolation of sixty-one diterpenoids and sesquiterpenoids, including seventeen previously undescribed compounds, metaglyptins A-Q. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, and 1H, 13C and 2D NMR). The absolute configurations of metaglyptins I, J, and O were determined by the ECD data and single-crystal X-ray diffraction analysis. The undescribed compounds were evaluated for their cytotoxicity against HeLa, AGS, and MDA-MB-231 cancer cell lines. The results revealed that metaglyptin A exhibited moderate cytotoxicity against MDA-MB-231 cell line with IC50 value of 20.02 μM.
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- 2019
21. Isolation, Structural Assignment of Isoselagintamarlin A from Selaginella tamariscina and Its Biomimetic Synthesis
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Jiangxin Liu, Qin-Shi Zhao, Li-Dong Shao, Xing-De Wu, and Qin-Feng Zhu
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Stereochemistry ,Pharmacology toxicology ,Selaginella tamariscina ,Plant Science ,Toxicology ,01 natural sciences ,Biochemistry ,Analytical Chemistry ,chemistry.chemical_compound ,Biomimetic synthesis ,lcsh:Botany ,Benzofuran ,Pharmacology ,Selaginellin ,010405 organic chemistry ,Organic Chemistry ,Intramolecular cyclization ,0104 chemical sciences ,lcsh:QK1-989 ,010404 medicinal & biomolecular chemistry ,chemistry ,Isoselagintamarlin A ,Plant biochemistry ,Original Article ,Food Science - Abstract
Isoselagintamarlin A (1), a selaginellin analogue featured a rare benzofuran unit, was isolated from Selaginella tamariscina. Its complete structural assignment was established through a combination of high-field NMR technique and biomimetic synthesis. Notably, isoselagintamarlin A (1) was successfully synthesized via sequential oxidations and intramolecular cyclization. Graphical Abstract Electronic supplementary material The online version of this article (10.1007/s13659-018-0195-5) contains supplementary material, which is available to authorized users.
- Published
- 2019
22. Tetranorlanostane and Lanostane Triterpenoids with Cytotoxic Activity from the Epidermis of Poria cocos
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Qin-Shi Zhao, Xing-De Wu, Lin-Fen Ding, Liu-Yan Wang, Wei Nie, Tie Lei, and Ting-Ting Jiang
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Models, Molecular ,Double bond ,Stereochemistry ,Molecular Conformation ,Bioengineering ,Antineoplastic Agents ,Crystallography, X-Ray ,01 natural sciences ,Biochemistry ,Lanostane ,chemistry.chemical_compound ,Triterpenoid ,Cell Line, Tumor ,Cytotoxic T cell ,Humans ,Molecular Biology ,Cell Proliferation ,chemistry.chemical_classification ,Epidermis (botany) ,Dose-Response Relationship, Drug ,010405 organic chemistry ,Stereoisomerism ,General Chemistry ,General Medicine ,Triterpenes ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry ,Molecular Medicine ,Cancer cell lines ,Drug Screening Assays, Antitumor ,Epidermis ,Lactone ,Wolfiporia - Abstract
Two unprecedented tetranorlanostane triterpenoids, poricolides A ( 1 ) and B ( 2 ), and two new lanostane triterpenoids, 3 β -acetoxy-24-methyllanosta-8,16,24(31)-trien-21-oic acid ( 3 ) and 3 β -acetoxylanosta-7,9(11),16,23-tetraen-21-oic acid ( 4 ), were isolated from the epidermis of Poria cocos . The structures of 1 - 4 were determined via analysis of 1 H-, 13 C-, and 2D-NMR, and HR-ESI-MS data, and the absolute configurations of 1 and 3 were established by single-crystal X-ray diffraction analysis. Compounds 1 and 2 were the first report of tetranorlanostane triterpenoid having a δ- lactone ring at C(17). Compounds 3 and 4 were rare lanostane triterpenoids having a double bond between C(16) and C(17). Compounds 1 - 4 exhibited potent antiproliferative effects against A549, SMMC-7721, MCF-7, and SW480 cancer cell lines with IC 50 values between 16.19 ± 0.38 to 27.74 ±1.12 μ M.
- Published
- 2021
23. Rearranged neoclerodane diterpenoids from the aerial parts of Salvia hispanica L
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Qin-Shi Zhao, Dan Luo, Li-Yan Peng, Min Fan, Xu Ji, and Xing-De Wu
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Pharmacology ,Cardiotonic Agents ,Molecular Structure ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Salvia hispanica ,Phytochemicals ,General Medicine ,Hydrogen Peroxide ,Plant Components, Aerial ,01 natural sciences ,food.food ,0104 chemical sciences ,Diterpenes, Clerodane ,010404 medicinal & biomolecular chemistry ,food ,Drug Discovery ,Animals ,Myocytes, Cardiac ,Salvia ,Rats, Wistar ,Two-dimensional nuclear magnetic resonance spectroscopy ,Cells, Cultured - Abstract
Six new rearranged neoclerodane diterpenoids (1–6), as well as three known ones, were obtained from the aerial part of Salvia hispanica L. Their structures were elucidated by extensive analysis of spectroscopic data (1D, 2D NMR, and HRESIMS) and Mosher's method. The absolute configurations of 1, 2, and 4 were determined by single-crystal X-ray diffraction analysis. All isolated compounds were evaluated for their cardioprotective effects against H2O2-induced cardiomyocytes injury, and compound 5 showed statistically significant cardioprotective effect in vitro assays.
- Published
- 2020
24. Huperserratines A and B, Two Macrocyclic
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Xing-De, Wu, Xiao-Nian, Li, Li-Yan, Peng, and Qin-Shi, Zhao
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Alkaloids ,Molecular Structure ,Huperzia ,Lycopodium ,Skeleton - Abstract
Huperserratines A (
- Published
- 2020
25. Caesalpanins A-C, Three Dimeric Cassane Diterpenoids from the Seeds of Caesalpinia sappan L
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Liu-Dong Song, De-Sheng Wang, Ting-Ting Jiang, Qin-Shi Zhao, Xing-De Wu, Lin-Fen Ding, and Wei Nie
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Lipopolysaccharides ,Caesalpinia sappan ,Stereochemistry ,Dimer ,Molecular Conformation ,Bioengineering ,Ether ,Nitric Oxide ,Biochemistry ,chemistry.chemical_compound ,Mice ,Structure-Activity Relationship ,Animals ,Humans ,Cytotoxicity ,Molecular Biology ,IC50 ,Cell Proliferation ,Caesalpinia ,biology ,Dose-Response Relationship, Drug ,Chemistry ,General Chemistry ,General Medicine ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Terpenoid ,RAW 264.7 Cells ,Seeds ,MCF-7 Cells ,Molecular Medicine ,Diterpenes ,Drug Screening Assays, Antitumor - Abstract
Three dimeric cassane diterpenoids, caesalpanins A-C, were isolated from the seeds of Caesalpinia sappan L., as well as three known compounds. Their structures were determined via analysis of 1D-, 2D-NMR, and HR-ESI-MS data. Caesalpanins A and B were the second and third compounds that presented a nitrogen-containing cassane diterpenoid dimer linked through one ether bond between C-19 and C-20'. Caesalpanin B exhibited moderate cytotoxic activity against MCF-7 cell lines with IC50 value of 29.98 μm. Caesalpanins A and B had weak inhibitory effects against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages at 50 μm with inhibitory rate of 36.01 % and 32.93 %, respectively.
- Published
- 2020
26. Salvifarinin A, a neo-clerodane diterpenoid with a 6/5/7 tricyclic skeleton from Salvia farinacea
- Author
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Qin-Shi Zhao, Min Fan, Xu Ji, Li-Dong Shao, Xue-Jiao Chen, and Xing-De Wu
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chemistry.chemical_classification ,biology ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Absolute configuration ,010402 general chemistry ,Ring (chemistry) ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Skeleton (computer programming) ,Semisynthesis ,Terpenoid ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Furan ,Drug Discovery ,Tricyclic ,Salvia farinacea - Abstract
Salvifarinin A (1), a rearrangement product of Languidulane-type clerodane diterpenoids with a 6/5/7 tricyclic ring skeleton fused with gamma-lactone ring and furan ring, and two new biogenetically related diterpernoids, salvifarinins B (2) and C (3), were isolated from the aerial parts of Salvia farinacea. The absolute configuration of 1 was elucidated by extensive spectroscopic methods, and confirmed by single crystal X-ray diffraction and bio-inspired semisynthesis. The plausible biogenetic pathway was also proposed. Compound 2 displayed a potent effect on reducing hepatic steatosis. (C) 2018 Published by Elsevier Ltd.
- Published
- 2018
27. Lycogladines A-H, fawcettimine-type Lycopodium alkaloids from Lycopodium complanatum var. glaucum Ching
- Author
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Qin-Shi Zhao, Yan-Yan Qi, Xing-De Wu, Jia Su, and Zhi-Jun Zhang
- Subjects
Fawcettimine ,Lycopodium ,biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,010402 general chemistry ,biology.organism_classification ,Lycopoclavamine B ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Drug Discovery ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Five new fawcettimine-type alkaloids (1–5) and three new natural products (6–8), along with four known analogues, fawcettimine (9), fewcettidine (10), lycopoclavamine B (11), and lycopladine B (12), were isolated from the whole plant of Lycopodium complanatum var. glaucum Ching. The structures of lycogladines A-H (1–8) were determined based on HRESIMS, 1D and 2D NMR spectroscopic analysis, as well as single-crystal X-ray diffraction. Compound 1 possesses a new ring system that is formed through the linkage of C-13-O C-2, which is rarely present in Lycopodium alkaloids (LAs). Compounds 1–8 were tested for their β-site amyloid precursor protein (APP)-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AChE) inhibitory activities.
- Published
- 2018
28. Atractylmacrols A-E, sesquiterpenes from the rhizomes of Atractylodes macrocephala
- Author
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Shuang-Yan Wang, Li-Yan Peng, Liu-Dong Song, Lin-Fen Ding, Xing-De Wu, and Jia Su
- Subjects
Atractylodes macrocephala ,010404 medicinal & biomolecular chemistry ,Traditional medicine ,Phytochemical ,010405 organic chemistry ,Chemistry ,Plant Science ,01 natural sciences ,Agronomy and Crop Science ,Biochemistry ,0104 chemical sciences ,Biotechnology ,Rhizome - Abstract
Phytochemical investigation of the rhizomes of Atractylodes macrocephala led to the isolation of five new sesquiterpenes, atractylmacrols A-E (1-5), as well as six known eudesmane sesquiterpenes (6-11). The structures of 1-5 were determined through interpretation of their 1D and 2D NMR spectroscopic data, as well as HREIMS values. Compounds 1-5 were evaluated for their inhibitory effects on LPS-induced nitric oxide (NO) production in RAW264.7 macrophages.
- Published
- 2018
29. Salvihispin A and its glycoside, two neo -clerodane diterpenoids with neurotrophic activities from Salvia hispanica L
- Author
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Ru-Nan Du, Yu Zhu, Qin-Feng Zhu, Zhijun Zhang, Min Fan, Xing-De Wu, and Qin-Shi Zhao
- Subjects
chemistry.chemical_classification ,Neurite ,biology ,010405 organic chemistry ,Salvia hispanica ,Stereochemistry ,Organic Chemistry ,Glycoside ,010402 general chemistry ,01 natural sciences ,Biochemistry ,food.food ,Terpenoid ,0104 chemical sciences ,food ,chemistry ,Drug Discovery ,biology.protein ,Moiety ,Neurotrophin - Abstract
A neo-clerodane diterpenoid, salvihispin A (1), as well as its glycoside, salvihispin A-2-O-beta-D-3-keto-glucopyranoside (2) were isolated from the aerial parts of Salvia hispanica. Compound 2 possessed an unusual 3-keto-glucopyranoside moiety. Their structures and absolute configurations were elucidated by extensive spectroscopic methods and confirmed by single crystal X-ray diffraction. Salvihispin A (1) and its glycoside (2) enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 mu M. (C) 2017 Elsevier Ltd. All rights reserved.
- Published
- 2018
30. Monoterpene Indole Alkaloids with Cav3.1 T-Type Calcium Channel Inhibitory Activity from Catharanthus roseus
- Author
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Lei Wang, Qin-Shi Zhao, Xing-De Wu, Zhen-Tao Deng, Wen-Yan Li, Zhi-Ping Zhou, and Zhong-Tao Ding
- Subjects
Catharanthus ,monoterpene indole alkaloid ,Stereochemistry ,Monoterpene ,Molecular Conformation ,Pharmaceutical Science ,Molecular Dynamics Simulation ,Article ,Indole Alkaloids ,Analytical Chemistry ,Calcium Channels, T-Type ,Structure-Activity Relationship ,QD241-441 ,Cav3.1 low voltage-gated calcium channel (LVGCC) ,Drug Discovery ,Physical and Theoretical Chemistry ,Indole test ,Dose-Response Relationship, Drug ,Molecular Structure ,Catharanthus roseus ,biology ,Plant Extracts ,Chemistry ,Calcium channel ,Alkaloid ,Organic Chemistry ,Absolute configuration ,T-type calcium channel ,Calcium Channel Blockers ,biology.organism_classification ,Molecular Docking Simulation ,catharanosine A ,Phytochemical ,Chemistry (miscellaneous) ,Monoterpenes ,Molecular Medicine - Abstract
Catharanthus roseus is a well-known traditional herbal medicine for the treatment of cancer, hypertension, scald, and sore in China. Phytochemical investigation on the twigs and leaves of this species led to the isolation of two new monoterpene indole alkaloids, catharanosines A (1) and B (2), and six known analogues (3–8). Structures of 1 and 2 were established by 1H-, 13C- and 2D-NMR, and HREIMS data. The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 2 represented an unprecedented aspidosperma-type alkaloid with a 2-piperidinyl moiety at C-10. Compounds 6–8 exhibited remarkable Cav3.1 low voltage-gated calcium channel (LVGCC) inhibitory activity with IC50 values of 11.83 ± 1.02, 14.3 ± 1.20, and 14.54 ± 0.99 μM, respectively.
- Published
- 2021
31. Discovery of pseudolaric acid A as a new Hsp90 inhibitor uncovers its potential anticancer mechanism
- Author
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Wen-Yan Li, Yang Kun, Zaifeng Yuan, Jiangxin Liu, Xing-De Wu, and Qin-Shi Zhao
- Subjects
Cell cycle checkpoint ,Antineoplastic Agents ,Apoptosis ,Biochemistry ,Hsp90 inhibitor ,HeLa ,Structure-Activity Relationship ,Drug Discovery ,Tumor Cells, Cultured ,medicine ,Humans ,Structure–activity relationship ,HSP90 Heat-Shock Proteins ,Molecular Biology ,Cell Proliferation ,Dose-Response Relationship, Drug ,Molecular Structure ,biology ,Photoaffinity labeling ,Chemistry ,Cell Cycle ,Organic Chemistry ,biochemical phenomena, metabolism, and nutrition ,biology.organism_classification ,Hsp90 ,Mechanism of action ,biology.protein ,Diterpenes ,Drug Screening Assays, Antitumor ,medicine.symptom - Abstract
Pseudolaric acid A (PAA), one of the main bioactive ingredients in traditional medicine Pseudolarix cortex, exhibits remarkable anticancer activities. Yet its mechanism of action and molecular target have not been investigated and remain unclear. In this work, mechanistic study showed that PAA induced cell cycle arrest at G2/M phase and promoted cell death through caspase-8/caspase-3 pathway, demonstrating potent antiproliferation and anticancer activities. PAA was discovered to be a new Hsp90 inhibitor and multiple biophysical experiments confirmed that PAA directly bind to Hsp90. Active PAA-probe was designed, synthesized and biological evaluated. It was subsequently employed to verify the cellular interaction with Hsp90 in HeLa cells through photoaffinity labeling approach. Furthermore, NMR experiments showed that N-terminal domain of Hsp90 and essential groups in PAA are important for the protein-inhibitor recognition. Structure-activity relationship studies revealed the correlation between its Hsp90 inhibitory activity with anticancer activity. This work proposed a potential mechanism involved with the anticancer activity of PAA and will improve the appreciation of PAA as a potential cancer therapy candidate.
- Published
- 2021
32. New limonoids and quinolone alkaloids with cytotoxic and anti-platelet aggregation activities from Evodia rutaecarpa (Juss.) Benth
- Author
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Hong-you Li, He Jiangbo, Jing Qin, Jia Su, Chao-Nan Liao, Wei-wei Chen, Gao-hong Zhang, and Xing-De Wu
- Subjects
Blood Platelets ,Limonins ,China ,Platelet Aggregation ,Limonin ,medicine.drug_class ,Phytochemicals ,Quinolones ,Limonoid ,01 natural sciences ,Evodia ,chemistry.chemical_compound ,Alkaloids ,Cell Line, Tumor ,Drug Discovery ,medicine ,Humans ,Cytotoxic T cell ,Pharmacology ,Molecular Structure ,Traditional medicine ,010405 organic chemistry ,Chemistry ,General Medicine ,Quinolone ,Antineoplastic Agents, Phytogenic ,Anti platelet ,0104 chemical sciences ,Human tumor ,010404 medicinal & biomolecular chemistry ,Evodia rutaecarpa ,Fruit ,Two-dimensional nuclear magnetic resonance spectroscopy ,medicine.drug - Abstract
One new limonoid, named 19-hydroxy methyl isoobacunoate diosphenol (1); one new degraded limonoid, named 9α-methoxyl dictamdiol (9); two new quinolone alkaloids, 1-methyl-3-[(7E,9E,12Z)-7,9,12-pentadecadienyl]-4(1H)-quinolone (11) and 1-methyl-3-[(7E,9E,11E)-7,9,11-pentadecadienyl]-4(1H)-quinolone (12), along with eight known compounds, evodol (2), 7β-acetoxy-5-epilimonin (3), rutaevine (4), 6β-acetoxy-5-epilimonin (5), limonin (6), obacunone (7), clauemargine L (8), hiiranlactone E (10) were isolated from the fruits of Evodia rutaecarpa (Juss.) Benth.. Structures of the four new compounds were elucidated on the basis of extensive spectroscopic techniques, including 1D and 2D NMR techniques. Compounds 3, 5, 9, 11 and 12 showed obviously cytotoxic activity against six human tumor lines, while compounds 11, 12 displayed anti-platelet aggregation induced by ADP at 50 μM and 100 μM.
- Published
- 2021
33. Lycoplanine A, a C16N Lycopodium Alkaloid with a 6/9/5 Tricyclic Skeleton from Lycopodium complanatum
- Author
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Qin-Shi Zhao, Xiao-Nian Li, Jia Su, Jian Yang, Zhi-Jun Zhang, Yin Nian, Xing-De Wu, and Qin-Feng Zhu
- Subjects
chemistry.chemical_classification ,Lycopodium ,biology ,010405 organic chemistry ,Dodecane ,Stereochemistry ,Organic Chemistry ,Absolute configuration ,010402 general chemistry ,biology.organism_classification ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Moiety ,Physical and Theoretical Chemistry ,Nonane ,Lycopodium alkaloid ,Tricyclic - Abstract
Lycoplanine A (1), a Lycopodium alkaloid with a 6/9/5 tricyclic ring skeleton fused with the γ-lactone ring and featuring an unusual 1-oxa-6-azaspiro[4.4]nonane moiety and an unprecedented 3-azabicyclo[6.3.1]dodecane unit, was isolated from the club moss Lycopodium complanatum. The structure and absolute configuration of 1 were identified by a combination of NMR spectroscopic analysis and single-crystal X-ray diffraction. Biological studies showed that 1 is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 value of 6.06 μM.
- Published
- 2017
34. Sauruchinenols A and B, unprecedented monocyclic diterpenes with new carbon skeleton from the aerial parts of Saururus chinensis
- Author
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Xiu Gao, Qin-Shi Zhao, Xing-De Wu, Xiao Cheng, Juan He, Li-Dong Shao, Li-Yan Peng, and Yan Li
- Subjects
Pharmacology ,Saururaceae ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Carbon skeleton ,General Medicine ,Plant Components, Aerial ,Nitric Oxide ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Saururus chinensis ,Mice ,010404 medicinal & biomolecular chemistry ,RAW 264.7 Cells ,Drug Discovery ,Animals ,Diterpenes - Abstract
Sauruchinenols A (1) and B (2), two novel monocyclic diterpenes with unique carbon skeleton, as well as two new structurally related diterpenes, sauruchinenols C (3) and D (4), were isolated from the aerial part of Saururus chinensis. Their structures were elucidated based on the analysis of spectroscopic data. A hypothetical biogenetic pathway for sauruchinenols A and B was proposed.
- Published
- 2017
35. Sesquiterpenoids from the twigs and leaves of Fokienia hodginsii
- Author
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Hui Yang, Li-Yan Peng, Xun Gong, Lin-Fen Ding, Wen-Wen Zhong, Yan Li, Qin-Shi Zhao, Xing-De Wu, Wen-Chao Tu, and Zhong-Zhi Xu
- Subjects
Cupressaceae ,Stereochemistry ,Pharmaceutical Science ,HL-60 Cells ,Sw480 cell ,01 natural sciences ,Analytical Chemistry ,Drug Discovery ,Botany ,Humans ,Sesquiterpenes, Eudesmane ,Pharmacology ,Molecular Structure ,Plant Stems ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Fokienia hodginsii ,General Medicine ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,0104 chemical sciences ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Molecular Medicine ,Drug Screening Assays, Antitumor ,Sesquiterpenes ,Two-dimensional nuclear magnetic resonance spectroscopy ,Drugs, Chinese Herbal - Abstract
A rare carotane-type sesquiterpenoid, forkienin A (1), a new eudesmane-type sesquiterpenoid, forkienin B (2), and a new natural eudesmane-type sesquiterpenoid, forkienin C (3), were isolated from the twigs and leaves of Fokienia hodginsii, along with eight known sesquiterpenoids. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, including 1D and 2D NMR methods. All compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines.
- Published
- 2016
36. Phlegmadine A: A
- Author
-
Zhi-Jun, Zhang, Chen, Wang, Xing-De, Wu, Yan, Huang, Wen-Xia, Zhou, and Qin-Shi, Zhao
- Subjects
Models, Molecular ,Mice ,Alkaloids ,Long-Term Potentiation ,Molecular Conformation ,Animals ,Lycopodium ,Cyclobutanes - Abstract
Phlegmadine A (
- Published
- 2019
37. Illilanceolide A, a unique seco-prezizaane sesquiterpenoid with 5/5/6 tricyclic scaffold from the fruits of Illicium lanceolatum A. C. Smith
- Author
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Lin-Fen Ding, Wei Nie, Xing-De Wu, Tie Lei, Qin-Shi Zhao, Zheng-Hong Pan, and Liu-Dong Song
- Subjects
chemistry.chemical_classification ,Neurite ,Illicium lanceolatum ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,chemistry ,Drug Discovery ,Two-dimensional nuclear magnetic resonance spectroscopy ,Tricyclic - Abstract
A unique seco-prezizaane sesquiterpenoid with 5/5/6 tricyclic skeleton, illilanceolide A (1), and two rare 10,14-cycloseco-prezizaane sesquiterpenoids, 2-oxo-6-dehydroxyneoanisatinic acid (2) and 3,4-anhydro-2-oxo-6-dehydroxyneoanisatinic acid (3), together with two known sesquiterpenoids, were isolated from the fruits of Illicium lanceolatum. Their structures and absolute configurations were elucidated on the basis of extensive 1H, 13C, and 2D NMR, and HRESIMS data, as well as single-crystal X-ray diffraction analysis. Compounds 2–4 enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM with differentiation rates of 13.33%, 10.90%, and 11.76%, respectively. Moreover, compounds 2–4 were found to exhibit moderate neuroprotective effect against MPP+-induced PC12 cell damage.
- Published
- 2021
38. (±)-Evodiakine, A Pair of Rearranged Rutaecarpine-Type Alkaloids From Evodia rutaecarpa
- Author
-
Yan-Hong Li, Qin-Shi Zhao, Xiao-Nian Li, Li-Yan Peng, Yu Zhang, Xing-De Wu, and Rong-Tao Li
- Subjects
Pharmacology ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Plant Science ,Rutaecarpine ,010402 general chemistry ,Toxicology ,Ring (chemistry) ,Mass spectrometry ,Circular dichroism spectra ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Analytical Chemistry ,Chiral column chromatography ,Evodia rutaecarpa ,Rutaecarpine-type alkaloids ,Original Article ,Enantiomer ,Two-dimensional nuclear magnetic resonance spectroscopy ,(±)-Evodiakine ,Food Science - Abstract
(±)-Evodiakine (1a and 1b), a pair of rearranged rutaecarpine-type alkaloids with an unprecedented 6/5/5/7/6 ring system, were isolated from the nearly ripe fruits of Evodia rutaecarpa. Separation of the enantiomers have been achieved by chiral HPLC column. The structures of (±)-evodiakine were unambiguously elucidated by 1D and 2D NMR spectra, mass spectrometry, and single-crystal X-ray diffraction. Their absolute configurations were determined by comparison of experimental and calculated electronic circular dichroism spectra. A hypothetical biogenetic pathway for (±)-evodiakine was also proposed. Compounds 1a, 1b, and the racemate (1) were tested for their cytotoxic and anti-inflammatory activities. Graphical Abstract Electronic supplementary material The online version of this article (doi:10.1007/s13659-016-0113-7) contains supplementary material, which is available to authorized users.
- Published
- 2016
39. Lyconadins G and H, Two Rare Lyconadin-Type Lycopodium Alkaloids from Lycopodium complanatum
- Author
-
Xiao-Nian Li, Li-Yan Peng, Xing-De Wu, Huai-Rong Luo, Qin-Shi Zhao, Jin-Tang Cheng, and Zhi-Jun Zhang
- Subjects
Pharmacology ,Lycopodium ,biology ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Pharmacology toxicology ,Absolute configuration ,Plant Science ,010402 general chemistry ,Toxicology ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Analytical Chemistry ,Lyconadin ,Plant biochemistry ,Original Article ,Lycopodium alkaloids ,Lycopodium alkaloid ,Lycopodium complanatum ,Food Science - Abstract
Two rare lyconadin-type Lycopodium alkaloids, lyconadins G (1) and H (2), together with four known ones (3–6), were isolated from Lycopodium complanatum. The structures were determined on the basis of their spectroscopic analyses, and the absolute configuration of 1 was established by an X-ray crystallographic analysis. It is the first time to establish the absolute configuration of lyconadin-type Lycopodium alkaloid by an X-ray diffraction experiment. In addition, these findings may provide more information for the biosynthesis of lyconadins. Graphical Abstract Electronic supplementary material The online version of this article (doi:10.1007/s13659-016-0111-9) contains supplementary material, which is available to authorized users.
- Published
- 2016
40. Bioactive sesquiterpenoids from the flowers of Inula japonica
- Author
-
Xing-De Wu, Qin-Shi Zhao, Wen-Chao Tu, Li-Yan Peng, Yan Li, Jia Su, Hui Yang, and Lin-Fen Ding
- Subjects
Lipopolysaccharides ,Inula japonica ,Stereochemistry ,Molecular Conformation ,HL-60 Cells ,Flowers ,Plant Science ,Horticulture ,Biology ,Crystallography, X-Ray ,Nitric Oxide ,01 natural sciences ,Biochemistry ,Inhibitory Concentration 50 ,Mice ,Sesquiterpenes, Guaiane ,Ic50 values ,Animals ,Humans ,Sesquiterpenes, Eudesmane ,No production ,Molecular Biology ,Molecular Structure ,010405 organic chemistry ,Macrophages ,Eupatolide ,General Medicine ,Asteraceae ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Phytochemical ,Inula ,Cancer cell lines ,Sesquiterpenes - Abstract
Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-Kα X-ray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC50 values ranging from 1.57 to 22.58 μM. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC50 values ranging from 1.42 to 8.99 μM.
- Published
- 2016
41. neo -Clerodanes from the aerial parts of Salvia leucantha
- Author
-
Li-Yan Peng, Xiao-Nian Li, Rong-Tao Li, Qin-Shi Zhao, Juan He, Xuan-Qin Chen, Xin Shi, Jia Su, Xing-De Wu, Li-Dong Shao, and Yong-Jun Jiang
- Subjects
biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Heat shock protein ,Drug Discovery ,Acetyl cholinesterase ,Salvia leucantha ,Cancer cell lines ,Cytotoxicity ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Ten new neo-clerodane derivatives (1–10) and 10 known diterpenoids were identified from the aerial parts of Salvia leucantha. The structures of 1–10 were established by 1D and 2D NMR spectroscopic data analysis. The absolute configurations of 1, 3, 6, and 7 were determined by X-ray diffraction data. Compound 16 exhibited cytotoxicity against HCT116, BT474, and HepG2 cancer cell lines and was identified as a heat shock protein 90 inhibitor. Compounds 8, 15, and 16 exhibited moderate acetyl cholinesterase inhibitory activity.
- Published
- 2016
42. Six new cassane diterpenoids from the seeds of Caesalpinia sappan
- Author
-
Qin-Shi Zhao, Lin-Fen Ding, Li-Yan Peng, Xing-De Wu, Liu-Dong Song, Zhen-Tao Deng, Jia Su, Hui Yang, and Wen-Chao Tu
- Subjects
Caesalpinia sappan ,biology ,Traditional medicine ,010405 organic chemistry ,Chemistry ,Plant Science ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Terpenoid ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Phytochemical ,Hepg2 cells ,Ic50 values ,Agronomy and Crop Science ,Biotechnology - Abstract
Six new cassane diterpenoids (1-6) and 15 known compounds were isolated and identified from the seeds of Caesalpinia sappan. The structures of the new compounds were determined based on the spectroscopic methods, including 1D and 2D NMR techniques. Compound 1 is a rare cassane diterpenoid featuring a nitrogen containing bridge between C-19 and C-20. Compounds 1 and 2 exhibited moderate cytotoxicity against HCT116, AGS, and HepG2 cell lines with IC50 values ranging from 6.36 to 27.86 mu M. (C) 2016 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
- Published
- 2016
43. Obscurumines H–P, new Lycopodium alkaloids from the club moss Lycopodium obscurum
- Author
-
Yan-Chun Liu, Juan He, Wei-Wei Jiang, Xiao Cheng, Zhi-Jun Zhang, Li-Yan Peng, Li-Dong Shao, Jia-Hui Yang, Qin-Shi Zhao, Xing-De Wu, Yu-Chen Liu, and Jia Su
- Subjects
Lycopodium ,Stereochemistry ,010402 general chemistry ,01 natural sciences ,Jurkat Cells ,chemistry.chemical_compound ,Alkaloids ,Drug Discovery ,Humans ,IC50 ,Cholinesterase ,Pharmacology ,Molecular Structure ,biology ,010405 organic chemistry ,General Medicine ,biology.organism_classification ,Moss ,Acetylcholinesterase ,In vitro ,0104 chemical sciences ,chemistry ,Lycopodium obscurum ,biology.protein ,Cholinesterase Inhibitors ,Two-dimensional nuclear magnetic resonance spectroscopy ,Immunosuppressive Agents ,Quinolizines - Abstract
Seven new fawcettimine-type (1-7) and two new lycopodine-type (8 and 9) Lycopodium alkaloids, as well as 10 known compounds, were isolated from the club moss, Lycopodium obscurum L. The structures of obscurumines H-P (1-9) were determined based on high-resolution MS and 1D and 2D NMR data. Compounds 1 and 2 include a new skeleton that is formed via the linkage of C-9-N-2', which is rarely present in Lycopodium alkaloids. The in vitro acetylcholinesterase (AChE) inhibitory activity assay showed that 5 exhibited weak anti-AChE activity with an IC50 value of 81.0 μM. Compound 8 exhibited inhibition of the secretion of IL-2 in phytohemagglutinin (PHA) and phorbol myristate acetate (PMA) stimulated Jurkat cells, and the IC50 value was 17.2 μM.
- Published
- 2016
44. Vinmajorines C - E, Monoterpenoid Indole Alkaloids fromVinca major
- Author
-
Zhi-Jun Zhang, Xing-De Wu, Rong-Tao Li, Qin-Shi Zhao, Juan He, Yan Li, and Ru-Nan Du
- Subjects
Monoterpenoid Indole Alkaloids ,biology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,Ms analysis ,010402 general chemistry ,Vinca major ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Catalysis ,0104 chemical sciences ,Inorganic Chemistry ,Cell culture ,Drug Discovery ,Cytotoxic T cell ,Physical and Theoretical Chemistry ,Human cancer - Abstract
Three new monoterpenoid indole alkaloids, vinmajorines C-E (1-3), along with 18 known analogues (4-21), were isolated from the whole plants of Vinca major. The new structures were elucidated as (5,15,16R,17,19,20,21)-10,17-dimethoxy-21-methyl-18-oxa-5,16-cycloyohimban-19-ol (1), (5,15,16R,17,20,21)-10-methoxy-21-methyl-18-oxa-5,16-cycloyohimban-17-ol (2), and (5,15,16R,17,20,21)-10-methoxy-21-methyl-18-oxa-5,16-cycloyohimban-17-yl acetate (3), respectively, by extensive NMR and MS analysis and comparison with known compounds. Compounds 1-3 were evaluated for their cytotoxic activities against five human cancer cell lines, compounds 1 and 3 showing moderate cytotoxic activities.
- Published
- 2016
45. Activation of SIK1 by phanginin A inhibits hepatic gluconeogenesis by increasing PDE4 activity and suppressing the cAMP signaling pathway
- Author
-
Yu Shen, Siwen Liu, Ying Feng, Qin-Shi Zhao, Suling Huang, Ying Leng, and Xing-De Wu
- Subjects
Male ,0301 basic medicine ,lcsh:Internal medicine ,Phanginin A ,030209 endocrinology & metabolism ,Type 2 diabetes ,Protein Serine-Threonine Kinases ,CREB ,Mice ,03 medical and health sciences ,0302 clinical medicine ,cAMP ,Cyclic AMP ,medicine ,Animals ,Glucose homeostasis ,Phosphorylation ,lcsh:RC31-1245 ,Salt-inducible kinase 1 ,Molecular Biology ,Phosphodiesterase 4 ,Gene knockdown ,Caesalpinia ,biology ,Plant Extracts ,Chemistry ,Kinase ,Gluconeogenesis ,Cell Biology ,medicine.disease ,Cyclic Nucleotide Phosphodiesterases, Type 4 ,Cell biology ,Mice, Inbred C57BL ,Glucose ,030104 developmental biology ,Diabetes Mellitus, Type 2 ,Liver ,Hepatocytes ,biology.protein ,cAMP-dependent pathway ,Original Article ,Diterpenes ,Signal Transduction - Abstract
Objective Salt-induced kinase 1 (SIK1) acts as a key modulator in many physiological processes. However, the effects of SIK1 on gluconeogenesis and the underlying mechanisms have not been fully elucidated. In this study, we found that a natural compound phanginin A could activate SIK1 and further inhibit gluconeogenesis. The mechanisms by which phanginin A activates SIK1 and inhibits gluconeogenesis were explored in primary mouse hepatocytes, and the effects of phanginin A on glucose homeostasis were investigated in ob/ob mice. Methods The effects of phanginin A on gluconeogenesis and SIK1 phosphorylation were examined in primary mouse hepatocytes. Pan-SIK inhibitor and siRNA-mediated knockdown were used to elucidate the involvement of SIK1 activation in phanginin A-reduced gluconeogenesis. LKB1 knockdown was used to explore how phanginin A activated SIK1. SIK1 overexpression was used to evaluate its effect on gluconeogenesis, PDE4 activity, and the cAMP pathway. The acute and chronic effects of phanginin A on metabolic abnormalities were observed in ob/ob mice. Results Phanginin A significantly increased SIK1 phosphorylation through LKB1 and further suppressed gluconeogenesis by increasing PDE4 activity and inhibiting the cAMP/PKA/CREB pathway in primary mouse hepatocytes, and this effect was blocked by pan-SIK inhibitor HG-9-91-01 or siRNA-mediated knockdown of SIK1. Overexpression of SIK1 in hepatocytes increased PDE4 activity, reduced cAMP accumulation, and thereby inhibited gluconeogenesis. Acute treatment with phanginin A reduced gluconeogenesis in vivo, accompanied by increased SIK1 phosphorylation and PDE4 activity in the liver. Long-term treatment of phanginin A profoundly reduced blood glucose levels and improved glucose tolerance and dyslipidemia in ob/ob mice. Conclusion We discovered an unrecognized effect of phanginin A in suppressing hepatic gluconeogenesis and revealed a novel mechanism that activation of SIK1 by phanginin A could inhibit gluconeogenesis by increasing PDE4 activity and suppressing the cAMP/PKA/CREB pathway in the liver. We also highlighted the potential value of phanginin A as a lead compound for treating type 2 diabetes., Highlights • Phanginin A inhibits gluconeogenesis in primary mouse hepatocytes. • Phanginin A increases hepatic SIK1 phosphorylation both in vitro and in vivo. • Activation of SIK1 increases PDE4 activity and suppresses the cAMP signaling pathway. • Activation of SIK1 inhibits gluconeogenesis by regulating the PDE4/cAMP/PKA/CREB pathway. • Phanginin A improves metabolic disorders in ob/ob mice.
- Published
- 2020
46. Artemilavanolides A and B, two sesquiterpenoids with a 6-oxabicyclo[3.2.1]octane scaffold from Artemisia lavandulaefolia
- Author
-
Qin-Shi Zhao, Hao-Feng Zhou, Lin-Fen Ding, Li-Yan Peng, Xing-De Wu, and Liu-Dong Song
- Subjects
Circular dichroism ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,chemistry.chemical_compound ,Artemisia lavandulaefolia ,chemistry ,Drug Discovery ,Single crystal ,Octane - Abstract
Artemilavanolides A (1) and B (2), two unprecedented sesquiterpenoids with 6-oxabicyclo[3.2.1]octane scaffold, as well as one known biogenetically related sesquiterpenoid, 11β,13-dihydrosantamarin (3), were isolated from the aerial parts of Artemisia lavandulaefolia. The structures and absolute configurations of 1 and 2 were characterized by analysis of HRESIMS, NMR spectroscopic, single crystal X-ray diffraction, and electronic circular dichroism (ECD) data. The plausible biogenetic pathway for 1 and 2 was also proposed. Compound 1 was found to enhance the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM.
- Published
- 2020
47. Phlegmadines B and C, two Lycopodium alkaloids with 6/5/5/5/7 pentacyclic skeleton from Phlegmariurus phlegmaria
- Author
-
Qin-Feng Zhu, Qin-Shi Zhao, Xing-De Wu, and Zhi-Jun Zhang
- Subjects
Lycopodium ,biology ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Absolute configuration ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Skeleton (computer programming) ,0104 chemical sciences ,Drug Discovery ,Lycopodium alkaloid ,Phlegmariurus phlegmaria - Abstract
Two Lycopodium alkaloids named phlegmadines B (1) and C (2), along with biogenetically related known compounds 3–6, were obtained from Phlegmariurus phlegmaria. Their structures were elucidated based on NMR spectroscopic analysis, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compounds 1 and 2 represent the first pentacyclic (6/5/5/5/7) C16N2 Lycopodium alkaloid skeleton. In addition, a possible biosynthetic pathway for 1 and 2 was proposed. Moreover, compound 1 exhibited moderate neurotrophic effects on PC12 cells.
- Published
- 2020
48. [A new cassane diterpene from Caesalpinia bonduc]
- Author
-
Wen-chao, Tu, Lin-fen, Ding, Hui, Yang, Liu-dong, Song, and Xing-de, Wu
- Subjects
Caesalpinia ,Molecular Structure ,Plant Extracts ,Seeds ,Diterpenes - Abstract
Five cassane diterpenes were isolated from the 95% ethanol extract of the seeds of Caesalpinia bonduc (Leguminosea) by a combination of various chromatographic methods, including silica gel, Sephadex LH-20, and semi-preparative HPLC. On the basis of spectroscopic techniques, their structures were identified as 3β-acetoxy-cassa-12,14(17),15-trien-7β-ol (1), caesalmin C (2), caesall E (3), caesalpinin MJ (4), and 1-deacetylcaesalmin C (5). Among them, compound 1 is a new compound and 2, 4, 5 were isolated from the plant for the first time.
- Published
- 2018
49. Cytotoxic sesquiterpenoids from the leaves of Magnolia grandiflora
- Author
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Liu-Dong Song, Xiao-Nian Li, Zhijun Zhang, Lin-Fen Ding, Qin-Shi Zhao, Jia Su, Zheng-Hong Pan, and Xing-De Wu
- Subjects
Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,HeLa ,chemistry.chemical_compound ,Structure-Activity Relationship ,Magnolia grandiflora ,Cell Line, Tumor ,Cytotoxic T cell ,Humans ,Parthenolide ,Enzyme Inhibitors ,Luciferases ,Molecular Biology ,IC50 ,Cell Proliferation ,biology ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,NF-kappa B ,General Medicine ,biology.organism_classification ,Molecular biology ,Antineoplastic Agents, Phytogenic ,0104 chemical sciences ,XIAP ,Plant Leaves ,010404 medicinal & biomolecular chemistry ,chemistry ,Cell culture ,Magnolia ,Signal transduction ,Drug Screening Assays, Antitumor ,Sesquiterpenes - Abstract
Nine previously undescribed sesquiterpenoids, named magnograndins A-I, as well as fourteen known ones, were obtained from the 70% acetone extract of the leaves of Magnolia grandiflora. Their structures were ascertained based on the spectroscopic evidences. The assignment of the relative configuration of magnograndin A was further confirmed by single-crystal X-ray diffraction analysis. 1β,10α-Epoxyparthenolide, parthenolide, and micheliolide exhibited potent cytotoxic activity against MDA-MB-468, AGS, HCT116, Hela, and MDA-MB-231 human cancer cell lines with IC50 values ranging from 1.76 to 16.11 μM. 1β,10α-Epoxyparthenolide and micheliolide potently inhibited NF-κB transcriptional activity with IC50 of 13.92 and 8.95 μM, respectively. The expression levels of NF-κB downstream protein p65 and XIAP were clearly down-regulated in 1β,10α-epoxyparthenolide and micheliolide treated cells, which demonstrated the inhibition of NF-κB signaling pathway.
- Published
- 2018
50. Two New Anti-Proliferative C
- Author
-
Yan-Yan, Qi, Jia, Su, Zhi-Jun, Zhang, Lai-Wei, Li, Min, Fan, Yu, Zhu, Xing-De, Wu, and Qin-Shi, Zhao
- Subjects
Models, Molecular ,Structure-Activity Relationship ,Tracheophyta ,Dose-Response Relationship, Drug ,Cell Line, Tumor ,Molecular Conformation ,Humans ,Diterpenes ,Drug Screening Assays, Antitumor ,Crystallography, X-Ray ,Antineoplastic Agents, Phytogenic ,Plant Roots ,Cell Proliferation - Abstract
Activity-guided fractionation strategy was used to investigate chemical constituents from the roots of Podocarpus macrophyllus. Successfully, two new norditerpenes, 2β-hydroxymakilactone A (1) and 3β-hydroxymakilactone A (2), along with ten known analogues (3 - 12) were isolated. The structures of 1 and 2 were elucidated by spectroscopic analysis including 1D-, 2D-NMR, and HR-ESI-MS data. The previously reported structure of 2,3-dihydro-2α-hydroxypodolide was revised as 2,3-dihydro-2β-hydroxypodolide (3) by spectroscopic analysis, and was further confirmed by X-ray crystallographic analysis. Cytotoxic activities of all isolated compounds against five human solid tumour cell lines (AGS, HeLa, MDA-MB-231, HepG-2, and PANC-1) were evaluated. All of them exhibited anti-proliferative activities (IC
- Published
- 2018
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