25609-85-2Relevant articles and documents
Identification and bioactivity of compounds from the fungus Penicillium sp. CYE-87 isolated from a marine tunicate
Shaala, Lamiaa A.,Youssef, Diaa T. A.
, p. 1698 - 1709 (2015)
In the course of our continuous interest in identifying bioactive compounds from marine microbes, we have investigated a tunicate-derived fungus, Penicillium sp. CYE-87. A new compound with the 1,4-diazepane skeleton, terretrione D (2), together with the known compounds, methyl-2-([2-(1H-indol-3-yl)ethyl]carbamoyl)acetate ( 1), tryptamine (3), indole-3-carbaldehyde (4), 3,6-diisobutylpyrazin-2(1H)-one (5) and terretrione C (6), were isolated from Penicillium sp. CYE-87. The structures of the isolated compounds were established by spectral analysis, including 1D (1H, 13C) and 2D (COSY, multiplicity edited-HSQC and HMBC) NMR and HRESIMS, as well as comparison of their NMR data with those in the literature. The compounds were evaluated for their antimigratory activity against the human breast cancer cell line (MDA-MB-231) and their antiproliferation activity against HeLa cells. Compounds 2 and 6 showed significant antimigratory activity against MDA-MB-231, as well as antifungal activity against C. albicans.
A new prenylated indole diketopiperazine alkaloid from Eurotium cristatum
Zou, Xianwei,Li, Ying,Zhang, Xiaona,Li, Qian,Liu, Xuan,Huang, Yun,Tang, Tao,Zheng, Saijing,Wang, Weimiao,Tang, Jintian
, p. 17839 - 17847 (2014)
A new prenylated indole diketopiperazine alkaloid, cristatumin F (1), and four known metabolites, echinulin (2), dehydroechinulin (3), neoechinulin A (4) and variecolorin O ( 5), were isolated from the crude extract of the fungus Eurotium cristatum. The structure of 1 was elucidated primarily by NMR and MS methods. The absolute configuration of 1 was assigned using Marfey's method applied to its acid hydrolyzate. Cristatumin F (1) showed modest radical scavenging activity against DPPH radicals, and exhibited marginal attenuation of 3T3L1 pre-adipocytes.
Homogeneous palladium-catalyzed enantioselective hydrogenation of 5-methylenhydantoin for the synthesis of L-Valine
Agbossou-Niedercorn, Francine,Bellière-Baca, Virginie,Hayouni, Safa,Michon, Christophe,Morvan, Didier
, (2020)
In this article, we present the development of a synthetic methodology based on homogeneous catalysis for the preparation of enantioenriched L-Valine aminoacid. The enantioselective hydrogenation of 5-methylenhydantoin has been developed through broad screenings of chiral ligands, metal precursors and reaction conditions including scale-up experiments and recyclability studies. A palladium catalyzed asymmetric hydrogenation of 5-methylenhydantoin afforded the corresponding hydrogenated product in a 70% enantiomeric excess using a substrate/catalyst ratio of 500/1. A partial racemization was observed upon hydrolysis and recovery of L-Valine.
Thalassospiramide G, a new γ-amino-acid-bearing peptide from the marine bacterium Thalassospira sp
Um, Soohyun,Pyee, Yuna,Kim, Eun-Hee,Lee, Sang Kook,Shin, Jongheon,Oh, Dong-Chan
, p. 611 - 622 (2013)
In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2-3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy- penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H-1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2-3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.
Amino acid N-carboxyanhydrides: Activated peptide monomers behaving as phosphate-activating agents in aqueous solution
Biron, Jean-Philippe,Pascal, Robert
, p. 9198 - 9199 (2004)
The hydrolysis of valine N-carboxyanhydride (NCA) in aqueous phosphate buffers was shown to proceed through nucleophilic catalysis via an aminoacyl phosphate intermediate that displays phosphorylating capabilities through a potentially prebiotic process that simulates modern biochemical metabolic pathways. Copyright
Isotactic polyethylenimines induce formation of L-amino acids in transamination
Bandyopadhyay, Subhajit,Zhou, Wenjun,Breslow, Ronald
, p. 1009 - 1012 (2007)
(Chemical Equation Presented) Isotactic polyethylenimines with (S)-benzyl side chains were synthesized from 4-(S)-4-benzyl-2-oxazolines. When α-keto acids were subjected to transamination in the presence of this polymer, and a pyridoxamine coenzyme modified with hydrophobic chains, enantioselectivity toward the natural isomer (L > D) was observed, followed by racemization of the amino acid products. However, the racemization did not occur when the coenzyme was covalently attached to the polymer.
Izenamides A and B, Statine-Containing Depsipeptides, and an Analogue from a Marine Cyanobacterium
Kanamori, Yuki,Iwasaki, Arihiro,Sumimoto, Shimpei,Matsubara, Teruhiko,Sato, Toshinori,Suenaga, Kiyotake
, p. 1673 - 1681 (2018)
Izenamides A, B, and C (1-3), new linear depsipeptides, were isolated from a taxonomically distinct marine cyanobacterium. Izenamides A and B contain a statine moiety [(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid] and inhibited the activity of cathepsin D, an aspartic peptidase. Meanwhile, izenamides did not show growth-inhibitory activity against HeLa, HL60, or MCF-7 cells at up to 10 μM.
Kakeromamide A, a new cyclic pentapeptide inducing astrocyte differentiation isolated from the marine cyanobacterium Moorea bouillonii
Nakamura, Fumiaki,Maejima, Hiroshi,Kawamura, Midori,Arai, Daisuke,Okino, Tatsufumi,Zhao, Meng,Ye, Tao,Lee, Jungyeol,Chang, Young-Tae,Fusetani, Nobuhiro,Nakao, Yoichi
, p. 2206 - 2209 (2018)
Kakeromamide A (1), a new cyclic pentapeptide encompassing a thiazole ring moiety and a β-amino acid, was isolated from the marine cyanobacterium Moorea bouillonii. Its structure was elucidated by the spectral analysis and the modified Marfey's method. Compound 1 induced differentiation of neural stem cells into astrocytes at the concentration of 10 μM.
Synthesis and stability studies of phosphonoformate-amino acid conjugates: A new class of slowly releasing foscarnet prodrugs
Marma, Mong S.,Kashemirov, Boris A.,McKenna, Charles E.
, p. 1787 - 1790 (2004)
Prodrugs of phosphonoformic acid (PFA), an anti-viral agent used clinically as the trisodium salt (foscarnet), are of interest due to the low bioavailability of the parent drug, which severely limits its utility. Neutral PFA triesters are known to be susceptible to P-C bond cleavage under hydrolytic de-esterification conditions, and it was previously found that P,C-dimethyl PFA P-N conjugates with amino acid ethyl esters did not release PFA at pH 7, and could not be fully deprotected under either acid or basic conditions, which led, respectively, to premature cleavage of the P-N linkage (with incomplete deprotection of the PFA ester moiety), or to P-C cleavage. Here we report that novel, fully deprotected PFA-amino acid P-N conjugates 4 can be prepared via coupling of C-methyl PFA dianion 2 with C-ethyl-protected amino acids using aqueous EDC, which gives a stable monoanionic intermediate 3 that resists P-C cleavage during subsequent alkaline deprotection of the two carboxylate ester groups. At 37°C, the resulting new PFA-amino acid (Val, Leu, Phe) conjugates (4a-c) undergo P-N cleavage near neutral pH, cleanly releasing PFA. A kinetic investigation of 4a hydrolysis at pH values 6.7, 7.2, and 8.5 showed that PFA release was first-order in [4a] with respective t1/2 values of 1.4, 3.8, and 10.6 h.
Aniquinazolines A-D, four new quinazolinone alkaloids from marine-derived endophytic fungus aspergillus nidulans
An, Chun-Yan,Li, Xiao-Ming,Li, Chun-Shun,Wang, Ming-Hui,Xu, Gang-Ming,Wang, Bin-Gui
, p. 2682 - 2694 (2013)
Four new quinazolinone alkaloids, namely, aniquinazolines A-D (1-4), were isolated and identified from the culture of Aspergillus nidulans MA-143, an endophytic fungus obtained from the leaves of marine mangrove plant Rhizophora stylosa. The structures of the new compounds were elucidated by spectroscopic analysis, and their absolute configurations were determined on the basis of chiral HPLC analysis of the acidic hydrolysates. The structure for 1 was confirmed by single-crystal X-ray diffraction analysis. All these compounds were examined for antibacterial and cytotoxic activity as well as brine shrimp (Artemia salina) lethality.
