- Two new tryptamine derivatives, leptoclinidamide and (-)-leptoclinidamine B, from an Indonesian ascidian Leptoclinides dubius
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Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C2-α-D-mannosylpyranosyl-L- tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic data for 1 and its N-acetyl derivative (4). Compound 1 was an amide of tryptamine with two β-alanine units. Although the planar structure of 2 is identical to that of the known compound (+)-leptoclinidamine B (5), compound 2 was determined to be the enantiomer of 5 based on amino acid analysis using HPLC methods. Compounds 1 to 4 were evaluated for cytotoxicity against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma) cells, but none of the compounds showed activity.
- Yamazaki, Hiroyuki,Wewengkang, Defny S.,Nishikawa, Teruaki,Rotinsulu, Henki,Mangindaan, Remy E. P.,Namikoshi, Michio
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Read Online
- New amino acid derivatives from the marine ascidian Leptoclinides dubius
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From the cytotoxic extracts of the marine ascidian Leptoclinides dubius, N-(p-hydroxybenzoyl)L-arginine (1), N-(1H-indolyl-3-carbonyl)-D-arginine (2), and N-(6-bromo-1H-indolyl-3-carbonyl)-R, where R is L-Arg (4), L-His (5), and the very rare amino acid L-enduracididine (3), have been isolated and identified by spectroscopic data, hydrolysis, and comparison with authentic samples.
- Garcia, Angel,Vazquez, Maria Jesus,Quinoa, Emilio,Riguera, Ricardo,Debitus, Cecile
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Read Online
- Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography
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In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.
- Li, Yingjie,Tang, Yimin,Qin, Shili,Li, Xue,Dai, Qiang,Gao, Lidi
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p. 283 - 292
(2019/02/05)
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- Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC
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Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3'-halogen substituted-1,1'-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one α-amino acids have different degrees of separation on R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1'-binaphthyl)-20-crown-6 derivatives. Both the separation factors (α) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 chiral stationary phase.
- Wu, Peng,Wu, Yuping,Zhang, Junhui,Lu, Zhenyu,Zhang, Mei,Chen, Xuexian,Yuan, Liming
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supporting information
p. 1037 - 1042
(2017/07/25)
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- METHOD FOR PREPARING D-ARGININE
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Disclosed is a method of preparing D-arginine, wherein D-arginine is obtained by the optical resolution of DL-arginine using D-3-bromocamphor-10-sulfonic acid as an optical resolving agent.
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Paragraph 0026-0035
(2017/09/02)
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- New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.
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Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acid hydrolysis and derivatisation of the free amino acids, and subsequent LCMS analysis of the derivatives. The compounds were evaluated for their activity against cancer cell lines A2058 (melanoma), HT-29 (colorectal adenocarcinoma) and MCF-7 (breast adenocarcinoma) and non-malignant MRC-5 fibroblast cells. While the acyclic callipeltins P and Q were inactive the cyclic callipeltins N and O showed significant cytotoxicity against all exposed cell lines with IC50values as low as 0.16?μM confirming the role of cyclic configuration in biological activity.
- Stierhof, Marc,Hansen, Kine ?stnes,Sharma, Mukesh,Feussner, Klaus,Subko, Karolina,Díaz-Rullo, Fernando Fernández,Isaksson, Johan,Pérez-Victoria, Ignacio,Clarke, David,Hansen, Espen,Jaspars, Marcel,Tabudravu, Jioji N.
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p. 6929 - 6934
(2016/10/14)
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- SEPARATING AGENT AND MANUFACTURING METHOD THEREOF
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An embodiment of the present invention is a separating agent wherein a group represented by a chemical formula of: or a group represented by a chemical formula of: is introduced on a surface thereof.
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Paragraph 0067; 0068; 0069; 0070; 0071; 0072;
(2015/01/07)
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- SEPARATING AGENT FOR CHROMATOGRAPHY
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A separating agent for chromatography is provided that is useful for the separation of specific compounds, e.g., for the optical resolution of amino acids. This separating agent for chromatography provides a higher productivity and contains a crown ether-like cyclic structure and optically active binaphthyl. This separating agent for chromatography containing a crown ether-like cyclic structure and optically active binaphthyl is provided by introducing a substitution group for binding to carrier into a specific commercially available 1,1′-binaphthyl derivative that has substituents at the 2, 2′, 3, and 3′ positions, then introducing a crown ether-like cyclic structure, and subsequently chemically bonding the binaphthyl derivative to the carrier through the substitution group for binding to carrier.
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Paragraph 0074; 0075
(2013/08/15)
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- New conjugates of muramyl dipeptide and nor-muramyl dipeptide linked to tuftsin and retro-tuftsin derivatives significantly influence their biological activity
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The synthesis and biological activity of new conjugates of muramyl dipeptide (MDP) and nor-muramyl dipeptide (nor-MDP) with tuftsin and retro-tuftsin derivatives containing isopeptide bond between e-amino group of lysine and carboxyl group of simple amino
- Dzierzbicka, Krystyna,Wardowska, Anna,Rogalska, Ma?gorzata,Trzonkowski, Piotr
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body text
p. 217 - 223
(2012/08/29)
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- Cytotoxic cyclic depsipeptides from the Australian marine sponge Neamphius huxleyi
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Three new cyclic depsipeptides, neamphamides B (2), C (3), and D (4), were isolated from the Australian sponge Neamphius huxleyi. The planar structural characterization of these molecules was elucidated using 2D NMR experiments and ESI-FTICR-MSn. Their configurations were determined by Marfey's method and J-based NMR analysis. These new metabolites inhibited the growth of human cell lines (A549, HeLa, LNCaP, PC3, and NFF) with IC50 values ranging from 88 to 370 nM. However, neamphamide D causes A549 cell proliferation at subcytotoxic doses and should be treated cautiously as a cytotoxic compound.
- Tran, Trong D.,Pham, Ngoc B.,Fechner, Gregory,Zencak, Dusan,Vu, Hoan T.,Hooper, John N.A.,Quinn, Ronald J.
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p. 2200 - 2208
(2013/02/25)
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- COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
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The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.
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Page/Page column 45-49; 61
(2010/12/31)
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- Complete stereochemistry of neamphamide A and absolute configuration of the β-methoxytyrosine residue in papuamide B
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The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-β-methoxy-L-tyrosine, (2R,3A,4S)-4-amino-7-guanidino-2,3-dihydroxy-heptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the β-methoxytyrosine residue in papuamide B (2) was found to be (R)-β-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.
- Oku, Naoya,Krishnamoorthy, Ravi,Benson, Alan G.,Ferguson, Robert L.,Lipton, Mark A.,Phillips, Lawrence R.,Gustafson, Kirk R.,McMahon, James B.
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p. 6842 - 6847
(2007/10/03)
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- Analysis of underivatized amino acids and their D/L-enantiomers by sheathless capillary electrophoresis/electrospray ionization-mass spectrometry
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Capillary electrophoresis/electrospray ionization-mass spectrometry (CE/ESI-MS) was applied to the analysis of underivatized amino acids and the separation of their D/L-enantiomers. Under full-scan mode, all standard protein amino acids were separated and detected at low-femtomole levels using a 130-cm-long, 20-μm-i.d., 150-μm-o.d. underivatized fused-silica capillary with 1 M formic acid as the background electrolyte. The CE/ESI-MS technique was also applied to the separation of L-arginine from L-canavanine (a close analogue of arginine where the terminal methylene linked to the guanidine group of arginine is replaced by an oxygen atom) in a complex mixture containing all standard protein amino acids. The utility of CE/ESI-MS in the analysis of real-world samples was demonstrated by the identification of two metabolic diseases (PKU and tyrosinemia) through blood analysis with minimal sample preparation. In addition, the on-line separation of 11 underivatized L-amino acids from their D-enantiomers was achieved by using a 30 mM solution of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as the background electrolyte.
- Schultz, Casey L.,Moini, Mehdi
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p. 1508 - 1513
(2007/10/03)
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- Substance P antagonists comprising rosaceae plant extracts
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Disease states, disorders, conditions or afflictions manifesting excessive synthesis and/or release of substance P are therapeutically treating by administering to individuals in need of such treatment, an effective substance P antagonist amount of at least one extract of at least one plant of the Rosaceae family.
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- Compounds for and methods of inhibiting matrix metalloproteinases
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The present invention relates to compounds of Formula I that inhibit matrix metalloproteinases and to a method of inhibiting matrix metalloproteinases using the compounds More particularly, the present invention relates to a method of treating diseases in which matrix metalloproteinases are involved such as multiple sclerosis, atherosclerotic plaque rupture, restenosis, aortic aneurysm, heart failure, periodontal disease, corneal ulceration, burns, decubital ulcers, chronic ulcers or wounds, cancer metastasis, tumor angiogenesis, osteoporosis, rheumatoid or osteoarthritis, renal disease, left ventricular dilatation, or other autoimmune or inflammatory diseases dependent upon tissue invasion by leukocytes.
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- A NOVEL ENZYME "Nα-BENZYLOXYCARBONYL AMINO ACID URETHANE HYDROLASE II" FROM LACTOBACILLUS FERMENTI 36 ATCC 9338
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A novel enzyme, "Nα-benzyloxycarbonyl amino acid urethane hydrolase II", was isolated from the cell-free extract of Lactobacillus fermenti 36 ATCC 9338.The enzyme showed hydrolytic activity toward Nα-benzyloxycarbonyl arginine.The purified enzyme was homogenous as indicated by disc gel electrophoresis.The molecular weight of the native enzyme is about 200,000 as estimated by gel filtration method.The isoelectric point was 5.0.The enzyme activity was inhibited by p-chloromercuribenzoic acid and ethylenediaminetetraacetic acid.The presence of divalent cations (i.e., Co(2+) or Zn(2+)) is essential for its activity. Keywords - novel enzyme; Urathane Hydrolase II; hydrolytic enzyme; Z-Arg; Lactobacillus fermenti 36 ATCC 9338; characterization; purification
- Matsumura, Eiko,Shin, Takashi,Murao, Sawao,Yamamoto, Eiko,Kawano, Tatsu
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p. 408 - 411
(2007/10/02)
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