1916-07-0Relevant articles and documents
A new cytotoxic cholestane bisdesmoside from Ornithogalum saundersiae bulbs
Mimaki, Yoshihiro,Kuroda, Minpei,Kameyama, Aiko,Sashida, Yutaka,Hirano, Toshihiko,Oka, Kitaro,Koike, Kazuo,Nikaido, Tamotsu
, p. 1049 - 1050 (1996)
Bioassay-guided fractionation of the MeOH extract of Ornithogalum saundersiae bulbs led to the isolation of a new cholestane bisdcsmoside with potent cytotoxic activities toward leukemia HL-60 and MOLT-4 cells. The structure was deduced mainly from spectroscopic information.
Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica
Zhang, Ying-Jun,Abe, Tomomi,Tanaka, Takashi,Yang, Chong-Ren,Kouno, Isao
, p. 1527 - 1532 (2001)
Six new ellagitannins, phyllanemblinins A-F (1-6), were isolated from Phyllanthus emblica, along with 30 known tannins and related compounds. Their structures were determined by spectral and chemical methods. Phyllanemblinins A (1) and B (2) were confirme
Design, synthesis and biological evaluation of a novel tubulin inhibitor 7a3 targeting the colchicine binding site
Lai, Qinhuai,Wang, Yuxi,Wang, Ruixue,Lai, Weirong,Tang, Liangze,Tao, Yiran,Liu, Yu,Zhang, Ruirui,Huang, Luyi,Xiang, Haotian,Zeng, Shaoxue,Gou, Lantu,Chen, Hao,Yao, Yuqin,Yang, Jinliang
, p. 162 - 179 (2018)
Tubulin inhibitors that target the colchicine binding site continue to emerge as promising anticancer agents. In this study, based on the anti-proliferative activities, a novel tubulin inhibitor 7a3 targeting the colchicine binding site was designed, synthesized, and optimized from a series of novel cis-restricted pyrazole analogues of combretastatin A-4. The structure-activity relationships (SARs) of these newly synthesized compounds are summarized indicating that the methyl substituent at the N1 position and deamination were significantly important for the anti-proliferative efficacy. The optimized compound 7a3 exhibited the ability to arrest the cell cycle in the G2/M phase, induce cell apoptosis, and inhibit cell migration in tumour cells. The results of the immunofluorescence analysis using confocal microscopy and the tubulin polymerization assay revealed that tubulin assembly was disrupted by 7a3 in vitro. Furthermore, the targeting identification of 7a3 was illuminated by solving the crystal structure of 7a3 in complex with tubulin at a resolution of 3.2 ? (PDB code 5Z4U), which confirmed the result of molecular docking and further demonstrated that 7a3 binds to the site of colchicine. Moreover, the pharmacokinetic analysis in mouse plasma showed that 7a3 rapidly reached a peak concentration at 0.25 h after intraperitoneal administration, and the T1/2, Cmax, and AUC0-inf were 1.67 ± 0.28 h, 882 ± 71 ng mL-1, and 1166 ± 129 h ng·mL-1, respectively, after a single-dose administration analysed by liquid chromatography-tandem mass spectrometry (LC/MS/MS). In addition, the in vivo study indicated that 7a3 significantly inhibited the tumour growth of the SK-OV-3 xenograft in a nude mouse model. In conclusion, our study proved 7a3 to be a potential microtubule-targeting drug for cancer therapy. The SARs and mechanism of action studies of 7a3 based on the X-ray co-crystal structure provided insights into the next-generation tubulin inhibitors for cancer therapy.
PUNICAFOLIN, AN ELLAGITANNIN FROM THE LEAVES OF PUNICA GRANATUM
Tanaka, Takashi,Nonaka, Gen-Ichiro,Nishioka, Itsuo
, p. 2075 - 2078 (1985)
A new ellagitannin, punicafolin has been isolated from the leaves of Punica granatum and characterized by physicochemical data and spectral evidence as 1,2,4-tri-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-β-D-glucose.The occurrence in the leaves of the known tannins, granatins A and B, corilagin, strictinin, 1,2,4,6-tetra-O-galloyl-β-D-glucose and 1,2,3,4,6-penta-O-galloyl-β-D-glucose has also been demonstrated.Key Word Index -Punica granatum; Punicaceae; pomegranate; punicafolin; ellagitannin; gallotannin.
Biologically active bergenin derivatives from bergenia stracheyi
Siddiq, Farah,Fatima, Itrat,Malik, Abdul,Afza, Nighat,Iqbal, Lubna,Lateef, Mehreen,Hameed, Saira,Khan, Sher Wali
, p. 91 - 98 (2012)
New bergenin derivatives, bergecins A and B (1 and 2, resp.), have been isolated from the AcOEt-soluble fraction of Bergenia stracheyi, along with bergenin (3), and their structures were elucidated on the basis of 1H- and 13C-NMR spectra, and by COSY, HMQC, and HMBC experiments. Compound 2 showed potent inhibitory potential against the enzyme lipoxygenase, while 1 was moderately active. On the other hand, both compounds exhibited significant antioxidant activities in 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay. Copyright
Synthesis of 2,3-dimethoxy-5-methyl-1,4-benzoquinone: A key fragment in coenzyme-q series
Chida,Vani,Chandrasekharam,Srinivasan,Singh
, p. 657 - 660 (2001)
Preparation of the title compound by a reaction sequence starting from gallic acid present in mango kernel is described.
Structure and biogenesis of jolkinin, a highly oxygenated ellagitannin from Euphorbia jolkinii
Lee, Seung-Ho,Tanaka, Takashi,Nonaka, Gen-Ichiro,Nishioka, Itsuo
, p. 1018 - 1022 (2004)
A new ellagitannin, jolkinin (2), was isolated from the fresh whole plant of Euphorbia jolkinii, and its structure, including absolute configuration, was determined on the basis of spectroscopic and chemical evidence. A highly oxygenated acyl group with unique hexacyclic structure is attached to the 2,4-positions of 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-β-D- glucopyranose. The structural similarity to elaeocarpusin (4) suggests that jolkinin is produced by a condensation reaction between ascorbic acid and geraniin (1), the dominant ellagitannin in this plant, which contains a dehydrohexahydroxydiphenoyl group. A plausible mechanism for jolkinin formation is also proposed.
Three novel C-glycosidic ellagitannins, Rhoipteleanins H, I, and J, from Rhoiptelea chiliantha
Jiang, Zhi-Hong,Tanaka, Takashi,Kouno, Isao
, p. 425 - 429 (1999)
Three novel C-glycosidic ellagitannins named rhoipteleanins H (1), I (2), and J (3) were isolated from the fruits and bark of Rhoiptelea chiliantha Diels et Hand.-Mazz. (Rhoipteleaceae), and the structures were elucidated on the basis of detailed spectroscopic analysis and chemical evidence. Rhoipteleanin H possesses a unique cyclopentenone carboxyl moiety, which is probably formed by oxidation and subsequent rearrangement of an aromatic ring of a usual C-glycosidic ellagitannin. Rhoipteleanin I is the first ellagitannin having a hydroxynaphthalene glucoside moiety. Rhoipteleanin J is a dimeric ellagitannin generated by dehydrative coupling between two molecules of a monomeric C-glycosidic ellagitannin and subsequent oxidation of an aromatic ring. From a chemotaxonomic viewpoint, presence of these characteristic ellagitannins in this plant provides a further support for the establishment of the order Rhoipteleales comprising Rhoipteleaceae as the only family.
Design and synthesis of novel parabanic acid derivatives as anticonvulsants
Aboutabl, Mona Elsayed,Hassan, Rasha Mohamed,El-Azzouny, Aida Abdel-Sattar,Aboul-Enein, Mohamed Nabil,Abd-Allah, Walaa Hamada
, (2019)
In this work a set of novel derivatives of parabanic acid 9a-d, 12a-d and 13a-d was synthesized and their anticonvulsant potential was evaluated. All the compounds under investigation exhibited anticonvulsant activity in both scPTZ and MES tests. In phase II anticonvulsant study, the trimethoxy phenyl derivative 9a evoked the highest potency among the tested compounds in scPTZ test. It displayed 1.72- and 17.05-folds activity more than the standard drugs phenobarbital and ethosuximide, respectively. In addition, the margin of safety for compound 9a is better than that of the reference antiepileptic drug ethosuximide. Also, compound 9a was devoid of hepatotoxicity indicated by measurements of serum level of ALT, AST, ALP, albumin and total protein. Furthermore, treatment with compound 9a significantly increased the GABA brain level by 2.56-folds compared to the control value. Additionally, molecular docking was performed on the active site of GABA-AT to clarify the interactions of the most potent compound 9a with the enzyme. In MES test, compound 12a exhibited the most potent activity against electric stimuli-induced seizures with the lowest ED50 = 13.7 mg/kg and protective index >36.5. Both candidates 9a and 12a could be a good starting point to develop new molecules as novel antiepileptic drugs.
Synthesis, characterization (theoretical and biological study) of some transition metal complexes with new schiff base derived from 1,2,4-triazole
AL-Jibouri, Mahmoud Najim,Jawad, Waleed A.,Balakit, Asim A.,Obies, Mohammed
, p. 5229 - 5241 (2021/08/31)
The present work involves, new Schiff base of (E)-2-(((3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)imino)methyl)phenol (L2) has been synthesized by condensation reaction of 4-amino-5-(3,4,5 trimethoxy phenyl)-4H-1,2,4-triazole-3-thiol with 2-hydroxybenzaldehyde. The new Schiff base (L2) used as a ligand to synthesize a new complex with Co(II), Ni(II), Cu(II), Pd(II), and Cd(II) metal ions by 1:1 (Metal: ligand) ratio. New ligand and their complexes have been exanimated and confirmed by fourier-transform infrared (FT-IR), ultraviolet-visible (UV-visible), proton nuclear magnetic resonance (1HNMR), carbon13 nuclear magnetic resonance (13CNMR), microelement analysis (CHNS), thermal analysis (TG-DSC), atomic absorption flame (AAF), conductivity and magnetic susceptibility. The results obtained from spectra, elemental analyses and thermal analyses (TG-DSC) and compare by density functional theory (DFT) and TD-DFT calculations were screened for some selected complexes and the observed data indicated their stability and the expected chemical formula, Pd(II) were square planner, whereas the Cu(II), Co(II), Ni(II) octahedral, and Cd(II) were tetrahedral geometry . Furthermore, the antibacterial and antifungal activity was screened for the DMSO solution concerning the Schiff base (L2) and its complexes (20 μg/ml) against two kinds of gram; (Staphylococcus aureas and Bacillus subtilis) positive and two negative bacteria; (Esherichia coli and Burkholderia) and against (Candida albican) fungi. The results obtained from diffusion method confirmed the greater activity of Pd(II) and Cd(II) complexes whereas the Co(II),Cu(II) and Ni(II) complexes showed medium activity compared with the low inhibition zones of the free Schiff base of 1, 2, 4- triazole derivative.
