25609-85-2Relevant articles and documents
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Adams,Tolbert
, (1958)
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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
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.
The occurrence of delta-hydroxylysine in extracts of the Japanese millipede (Scolopendra subspinipes Leach). Paper chromatographic separation of free amino acids and isolation of delta-hydroxylysine.
TOMITA
, p. 266 - 268 (1962)
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Sylvester,Stevens
, p. 4529 (1979)
Caspase-1 and -3 inhibiting drimane sesquiterpenoids from the extremophilic fungus Penicillium solitum
Stierle, Donald B.,Stierle, Andrea A.,Girtsman, Teri,McIntyre, Kyle,Nichols, Jesse
, p. 262 - 266 (2012)
Two new drimane sesquiterpene lactones and one new tricarboxylic acid derivative were isolated from the Berkeley Pit extremophilic fungus Penicillium solitum. The structures of these compounds were deduced by spectroscopic analysis. Berkedrimanes A and B inhibited the signal transduction enzymes caspase-1 and caspase-3 and mitigated the production of interleukin 1-β in the induced THP-1 (pro-monocytic leukemia cell line) assay.
Retention of configuration at C-3 of (2S,3S)-[4-13C]valine in the biosynthesis of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine, the acyclic precursor of the penicillins
Baxter,Scott,Fukumura
, p. 66 - 68 (1982)
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Miehl,Bachmayer
, (1964)
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Ehrenkaufer et al.
, p. 359,361 (1977)
Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii
Cao, Shugeng,Sarotti, Ariel M.,Uz Zaman, KH Ahammad,Wu, Xiaohua
, (2022/03/09)
The fungal strain Fusarium graminearum FM1010 was isolated from a shallow-water volcanic rock known as “live rock” at the Carl Smith Beach, Hilo, Hawaii. Eleven specialised metabolites, including two undescribed diketopiperazines, three undescribed polyketides, and one undescribed isochromanone, along with five known fusarielin derivatives were obtained from F. graminearum FM1010. The structures of the six undescribed compounds were elucidated by extensive analysis of NMR spectroscopy, HRESIMS, chemical reactions, and electronic circular dichroism (ECD) data. Kaneoheoic acids G-I showed mild inhibitory activity against S. aureus with the MIC values in the range of 20–40 μg/mL when assayed in combination with chloramphenicol (half of the MIC, 1 μg/mL), an FDA approved antibiotic. Kaneoheoic acid I exhibited both anti-proliferative activity against ovarian cancer cell line A2780 and TNF-α induced NF-κB inhibitory activity with the IC50 values of 18.52 and 15.86 μM, respectively.
Structures and antitumor activities of ten new and twenty known surfactins from the deep-sea bacterium Limimaricola sp. SCSIO 53532
Chen, Min,Chen, Rouwen,Ding, Wenping,Li, Yanqun,Tian, Xinpeng,Yin, Hao,Zhang, Si
, (2022/01/11)
Surfactins are natural biosurfactants with myriad potential applications in the areas of healthcare and environment. However, surfactins were almost exclusively produced by the bacterium Bacillus species in previous reported literatures, together with difficulty in isolating pure monomer, which resulted in making extensive effort to remove duplication and little discovery of new surfactins in recent years. In the present study, the result of Molecular Networking indicated that Limimaricola sp. SCSIO 53532 might well be a potential resource for surfacin-like compounds based on OSMAC strategy. To search for new surfactins with significant biological activity, further study was undertaken on the strain. As a result, ten new surfactins (1–10), along with twenty known surfactins (11–30), were isolated from the ethyl acetate extract of SCSIO 53532. Their chemical structures were established by detailed 1D and 2D NMR spectroscopy, HRESIMS data, secondary ion mass spectrometry (MS/MS) analysis, and chemical degradation (Marfey's method) analysis. Cytotoxic activities of twenty-seven compounds against five human tumor cell lines were tested, and five compounds showed significant antitumor activities with IC50 values less than 10 μM. Furtherly, analysis of structure–activity relationships revealed that the branch of side chain, the esterification of Glu or Asp residue, and the amino acid residue of position 7 possessed a great influence on antitumor activity.
Cyclic Tetrapeptides with Synergistic Antifungal Activity from the Fungus Aspergillus westerdijkiae Using LC-MS/MS-Based Molecular Networking
Chen, Baosong,Dai, Huanqin,Han, Junjie,Li, Erwei,Liu, Hongwei,Lyu, Zhitang,Song, Fuhang,Sun, Jingzu,Wang, Hanying,Wang, Tao,Wang, Wenzhao,Zhang, Rui
, (2022/02/17)
Fungal natural products play a prominent role in the development of pharmaceuticalagents. Two new cyclic tetrapeptides (CTPs), westertide A (1) and B (2), with eight known compounds (3-10) were isolated from the fungus Aspergillus westerdijkiae guided by
