Phenolic Constituents of Cassia Seeds and Antibacterial Effect of Some Naphthalenes and Anthraquinones on Methicillin-Resistant Staphylococcus aureus.

Hatano, Tsutomu; Uebayashi, Hiroshi; Ito, Hideyuki; Shiota, Sumiko; Tsuchiya, Tomofusa; Yoshida, Takashi

doi:10.1248/cpb.47.1121

Cited by 164 publications

(102 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Marine microorganism is a rich source of secondary metabolites with diverse structures and various biological activities, such as cytotoxic [1], antitumor [2], antimicrobial [3], and antimycobacterial [4] activities. In our continuing research on antitumor secondary metabolites from marine-derived microorganisms, a culture extract of an Aspergillus carbonarius strain isolated from the marine sediment collected at Weizhou Island, China, showed significant cytotoxic activity against K562 cell line at 10.0 m g/ml.…”

Section: Introductionmentioning

confidence: 99%

Carbonarones A and B, New Bioactive γ-Pyrone and α-Pyridone Derivatives from the Marine-derived Fungus Aspergillus carbonarius

et al. 2007

View full text Add to dashboard Cite

Two new secondary metabolites, carbonarones A (1) and B (2), were obtained from the culture of the marine-derived fungus Aspergillus carbonarius isolated from the marine sediment collected at Weizhou island of China. Based on ESIMS, 1D and 2D NMR data, and the X-ray crystallographic analysis, their structures were elucidated as 6-benzyl-4-oxo-4H-pyran-3-carboxamide and 6-benzyl-4-hydroxy-2-oxo-1, 2-dihydropyridine-3-carbaldehyde, respectively. 1 and 2 showed moderate cytotoxicity against K562 cells with IC 50 values of 56.0 and 27.8 mg/ml, respectively. [7]. The latter were effectively used to control Coleopteran and Lepidopteran insects. Further chemical investigation on metabolites of this fungal species was carried out, which led to the isolation and structural elucidation of two new compounds, carbonarones A (1) and B (2), (Fig. 1) via bioassay-guided isolation procedure. KeywordsThe bioactive secondary metabolites of the A. carbonarius were obtained from the EtOAc extract of the fermentation broth and mycelia. Isolation of the compounds was achieved by repeated chromatographic steps, including column chromatography on silica gel, Sephadex LH-20 and reversed-phase semipreparative HPLC. Materials and Methods StrainThe fungus strain Aspergillus carbonarius WZ-4-11 was isolated from the marine sediments collected in Nov.

show abstract

Section: Introductionmentioning

confidence: 99%

Carbonarones A and B, New Bioactive γ-Pyrone and α-Pyridone Derivatives from the Marine-derived Fungus Aspergillus carbonarius

et al. 2007

View full text Add to dashboard Cite

show abstract

“…12) C. tora have shown to possess various biological and pharmacological activities including antihepatotoxic, 13) radical scavenging, 14) antiallergic, 15) antimutagenic, 16) antifungal, 17) and antimicrobial. 18) Previous phytochemical investigation on the seeds of C. tora have resulted in the isolation of several anthraquinone and naphthopyrone derivatives. 13,[16][17][18][19][20] In the present study, further fractionation of the EtOAc-soluble extract of the seeds of C. tora led to the purification of nine anthraquinones (1)(2)(3)(4)(5)(6)(7)(8)(9).…”

mentioning

confidence: 99%

“…18) Previous phytochemical investigation on the seeds of C. tora have resulted in the isolation of several anthraquinone and naphthopyrone derivatives. 13,[16][17][18][19][20] In the present study, further fractionation of the EtOAc-soluble extract of the seeds of C. tora led to the purification of nine anthraquinones (1)(2)(3)(4)(5)(6)(7)(8)(9). The structures of 1-9 were determined by spectroscopic data interpretation and they were subjected to in vitro bioassays to evaluate their inhibitory activity against AGEs and RLAR.…”

mentioning

confidence: 99%

Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase

Jang

Lee

Kim

et al. 2007

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-b b-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-b b-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC 50 values of 118 and 28.9 m mM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. N e e -Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC 50 values of 13.6, 8.8, and 15.9 m mM, respectively.

show abstract

“…Anthraquinones have recently attracted increasing attention due to their various biological activities and a wide range of applications in the pharmaceutical industry [1][2][3][4]. Additionally, some anthraquinones have been proved to posses anti-cancer and antifungal properties [2,3].…”

Section: Introductionmentioning

confidence: 99%

“…2 10.0 ν C13C15 (13), ν C10C11 (13), ν O5C9 (9), ν C12C13 (6), ν C8C19 (6), 3 β 3/R6 (5) 76 1615.0 82.5 6.3 ρ N3H23 (19), ν C6C19 (8), ν C8C19 (7), ν C16C18 (7), ν C10C11 (7), ν C7C18 (7), ν C13C15 (7), 1 β 2/R6 (5) 77 1627.4 34.0 15.0 ν C14C15 (14), ν C11C12 (11), ν O5C9 (8), 3 β 2/R6 (7), ν C12C13 (7), ν C6C7 (5) 78 1631.2 279.7 4.8 ν C6C7 (16), ν C8C19 (6), 1 β 3/R6 (6), ν C14C15 (6), ν O4C17 (6) (8), ω N3H23 (6) 7 162.7 0.4 0.3 4 bfl RR (14), τ N3C18 (10), 2 bfl RR (10), 1 (13), 4 bfl RR (10) 11 221.4 5.2 0.4 τ S1C20 (21), δ 2/C20H31H32 (12), 2 bfl RR (8), β C18N3C2 (7), 4 bfl RR (7) (14), ν C11C17 (10), δ 2/C20H31H32 (7), ν C9C16 (6) 17 425.5 10.2 0.3 3 τ 3/R6 (40), ρ C9O5 (12), 4 bfl RR (10), 3 (15), ν S1C20 (8), ρ C18N3 (6) 27 652.2 1.9 0.9 ν S1C20 (58), 3 (8), ω C15H29 …”

mentioning

confidence: 99%

Relationship between structure and entropy contributions in an anthraquinone mercapto derivative

2010

View full text Add to dashboard Cite

The structural and thermodynamic properties of an anthraquinone derivative were studied by means of quantum-chemical calculations. As a result of the conformational analysis fourteen lowenergetic conformers were found by using ab initio and DFT methods. In order to discuss similarities and differences in entropy of the conformers, the rotational and vibrational contributions to entropy were correlated with changes in the conformer structure. The moment of inertia perpendicular to the molecular plane gives significant input to the ΔSrot, whereas the largest contributions to the ΔSvib have the vibrations associated with the τS1C20 coordinate.Response to Reviewers: Dear Prof. Andrzej Sokalski Editor in Chief of Journal of Molecular Modeling, I would like to thank the Referees for a careful reading of our manuscript and giving us the valuable comments that with no doubts will improve this paper (Mns.# JMMO1081). Please find below my answers to the Referees' suggestions and comments.Reviewer #1:Major Revisions 1. Some anthraquinones are proved to have anti-cancer and antifungal properties, as stated by the authors in the introduction. There, the anthraquinones are not in gas phase, but solved in the liquid phase or are interacting with the target in the liquid phase. In contrast, the calculations of the authors are performed in the gas phase. Thus, the authors should discuss, if their results have significance in drug research and for interaction between ligand and target. The molecular structure defined in the gas phase is a commonly accepted starting point in studies concerning biological activities of molecules. Indeed, we agree with the referee that the future research dealing strictly with biological activity of anthraquinones would require introduction of the solvent and simulation of a biological environment in computational models that is, by the way, a nontrivial problem. However, our studies on antraquinones brought us to finding of the entropic effect in the structures of the MEAA conformers and we decided to analyze this effect in detail. Therefore, our work, although mentioning biological functions of MEAA conformers, was in fact aimed to study the correlation of the rotational and vibrational contributions to entropy with changes in the conformer structure and to do this, the simplest possible model (the gas phase) occurred to us as the most preferable. In order to clarify our point of view we suggest adding two more sentences to Introduction (after : The highest emphasis was made on detailed analysis of the entropy effect in order to understand the relation between the structure and entropy contributions (translational, electronic, rotational and vibrational). The computations were done in the gas phase to simplify the computations. Nevertheless, it is hoped that this study can be a starting point in the future research concerning modeling of the biological activity of the MEAA in more complicated systems, mimicking the biological environment.2. How was the analysis of the potential energy p...

show abstract

Phenolic Constituents of Cassia Seeds and Antibacterial Effect of Some Naphthalenes and Anthraquinones on Methicillin-Resistant Staphylococcus aureus.

Cited by 164 publications

References 1 publication

Carbonarones A and B, New Bioactive γ-Pyrone and α-Pyridone Derivatives from the Marine-derived Fungus Aspergillus carbonarius

Carbonarones A and B, New Bioactive γ-Pyrone and α-Pyridone Derivatives from the Marine-derived Fungus Aspergillus carbonarius

Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase

Relationship between structure and entropy contributions in an anthraquinone mercapto derivative

Contact Info

Product

Resources

About