Category: Pyrazines

Shen, Shuo; Li, Wei published the artcile< The inhibitory effects of metabolites from Bacillus pumilus on potato virus Y and the induction of early response genes in Nicotiana tabacum>, SDS of cas: 2873-36-1, the main research area is Bacillus Nicotiana metabolites potato virus Y; Active compounds; Early response genes; Halophilic bacterium Bacillus pumilus; Inhibitory activity; Potato Virus Y genes encoding viral proteins.

To develop a new antiviral preparation from a microbial source, the halophilic bacterium Bacillus pumilus E303035 was isolated from a soil sample collected at Qarhan Salt Lake in Qinghai, China. The inhibitory activity of an Et acetate extract of its fermentation broth was higher than that of an n-butanol extract After isolation and purification, 9 compounds were obtained: cyclo(L-Leu-L-Pro) (1), cyclo(L-Pro-L-Tyr) (2), Brevianamide F (3), 2-(3-Indolyl) ethanol (4), N-[2-(1H-indol-3-yl) ethyl] acetamide (5), 3, 3-di(1H-indol-3-yl)propane-1,2-diol (6), Lincomycin B (7), dibutylphthalate (8), and p-hydroxyphenethyl alc. (9). Compounds 1, 5, and 9 showed inhibitory activities against potato virus Y (PVY). Compounds 1, 4, and 9 had significant inhibitory activity against genes HC-pro, P3, and Nib, compound 5 against gene P3, and compounds 1 and 4 against NIa. Compounds 1, 4, 5, and 9 had significant inhibitory activity against genes VPg and 6K1. Active compounds 1, 5, and 9 had various effects on the expression of viral genes related to pathogenesis. Expression of genes cullin and XTH was up-regulated and CP was down-regulated, compared to the pos. control.

AMB Express published new progress about Cullins Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, SDS of cas: 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Cao, Duc Danh; Trinh, Thi Thanh Van; Mai, Huong Doan Thi; Vu, Van Nam; Le, Hong Minh; Thi, Quyen Vu; Nguyen, Mai Anh; Duong, Thu Trang; Tran, Dang Thach; Chau, Van Minh; Ma, Rui; Shetye, Gauri; Cho, Sanghyun; Murphy, Brian T.; Pham, Van Cuong published the artcile< Antimicrobial lavandulylated flavonoids from a sponge-derived Streptomyces sp. G248 in East Vietnam Sea>, Quality Control of 2873-36-1, the main research area is Streptomyces antimicrobial lavandulylate flavonoid; Streptomyces; actinomycete; anti-microbial; anti-tuberculosis; cytotoxicity; flavonoid.

Three new lavandulylated flavonoids, (2S,2S)-6-lavandulyl-7,4-dimethoxy-5,2-dihydroxylflavanone (1), (2S,2-S)-6-lavandulyl-5,7,2,4-tetrahydroxylflavanone (2), and (2S)-5-lavandulyl-2-methoxy-2,4,4,6-tetrahydroxylchalcone (3), along with seven known compounds 4-10 were isolated from culture broth of Streptomyces sp. G248. Their structures were established by spectroscopic data anal., including 1D and 2D NMR (NMR), and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configurations of 1-3 were resolved by comparison of their exptl. and calculated electronic CD spectra. Compounds 1-3 exhibited remarkable antimicrobial activity. Whereas, two known compounds 4 and 5 exhibited inhibitory activity against Mycobacterium tuberculosis H37Rv with min. inhibitory concentration (MIC) values of 6.0 μg/mL and 11.1 μg/mL, resp.

Marine Drugs published new progress about Antimicrobial agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Quality Control of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Gajbhiye, Milind; Kapadnis, Balu published the artcile< Lactococcus lactis subsp. cremoris of Plant Origin Produces Antifungal Cyclo-(Leu-Pro) and Tetradecanoic Acid>, Application In Synthesis of 2873-36-1, the main research area is Lactococcus cyclic dipeptide tetradecanoic acid antifungal fungal infection; Biocontrol; Cyclo-(Leu-Pro); Lactic acid bacteria; Pomegranate; Tetradecanoic acid.

Abstract: The antifungal cyclo-depeptide and the fatty acid were isolated and purified from an indigenous strain of Lactococcus lactis subsp. cremoris. Maximal activity was observed at pH 5.5 and 6.5, and at 30°C under stationary conditions, which was detected in the culture supernatant 8 h post-inoculation in MRS broth until 22 h. The activity of antifungal compounds in the culture supernatant was sensitive to pH and temperature; and was protease-resistant. The antifungal compounds were concentrated by freeze-drying and ultrafiltration with activity retained in 1 kDa filtrates indicating low mol. weight metabolites. The compounds were further extracted by using different solvents amongst which, Et acetate provided the highest recovery. Antifungal compounds were separated on a silica gel column into two active fractions that were revealed to be tetradecanoic acid and cyclo-(Leu-Pro), a cyclic dipeptide, by GC-MS. Herein, we describe and attribute the biocontrol potential of L. lactis subsp. cremoris to the low mol. weight antifungal compounds isolated, which is the first report of their isolation from this strain. The broad antifungal spectrum of this candidate advocates further exploration of its biocontrol potential in managing fungal infections in different food and feed systems.

Indian Journal of Microbiology published new progress about Cyclic dipeptides Role: PRP (Properties). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Application In Synthesis of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Li, Zhihua; Zhao, Chi; Dong, Ling; Huan, Yu; Yoshimoto, Miwa; Zhu, Yongqing; Tada, Ipputa; Wang, Xiaohang; Zhao, Shuang; Zhang, Fengju; Li, Liang; Arita, Masanori published the artcile< Comprehensive Metabolomic Comparison of Five Cereal Vinegars Using Non-Targeted and Chemical Isotope Labeling LC-MS Analysis>, Recommanded Product: (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, the main research area is cereal vinegar metabolomics non target chem isotope; GC-MS; UHPLC-QTOF-MS; cereal vinegar; chemical isotope labeling; metabolomics; small peptides.

Vinegar is used as an acidic condiment and preservative worldwide. In Asia, various black vinegars are made from different combinations of grains, such as Sichuan bran vinegar (SBV), Shanxi aged vinegar (SAV), Zhenjiang aromatic vinegar (ZAV), and Fujian Monascus vinegar (FMV) in China and Ehime black vinegar in Japan (JBV). Understanding the chem. compositions of different vinegars can provide information about nutritional values and the quality of the taste. This study investigated the vinegar metabolome using a combination of GC-MS, conventional LC-MS, and chem. isotope labeling LC-MS. Different types of vinegar contained different metabolites and concentrations Amino acids and organic acids were found to be the main components. Tetrahydroharman-3-carboxylic acid and harmalan were identified first in vinegar. Various diketopiperazines and linear dipeptides contributing to different taste effects were also detected first in vinegar. Dipeptides, 3-phenyllactic acid, and tyrosine were found to be potential metabolic markers for differentiating vinegars. The differently expressed pathway between Chinese and Japanese vinegar was tryptophan metabolism, while the main difference within Chinese vinegars was aminoacyl-tRNA biosynthesis metabolism These results not only give insights into the metabolites in famous types of cereal vinegar but also provide valuable knowledge for making vinegar with desirable health characteristics.

Metabolites published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Recommanded Product: (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Lin, Wei-Xiang; Xie, Chun-Lan; Zhou, Mi; Xia, Man-Li; Zhou, Ting-Ting; Chen, Hai-Feng; Yang, Xian-Wen; Yang, Quan published the artcile< Chemical constituents from the deep sea-derived Streptomyces xiamenensis MCCC 1A01570 and their effects on RXRα transcriptional regulation>, Name: (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, the main research area is deep sea Streptomyces secondary metabolites RXRalpha anticancer; Deep sea; RXRα; Streptomyces xiamenensis; anticancer; secondary metabolites.

From the deep sea-derived Streptomyces xiamenensis MCCC 1A01570, eight cyclic dipeptides (1-8) and five phenolics (9-13) were obtained. Cyclo-(L-Pro-D-Leu) (4) could moderately promote the gene transcriptional function of nuclear receptor RXRα, while, and showed weak reduction in RXRα gene transcriptional activities induced by 9-cis-retinoid acid (RA). These compounds might have beneficial effects against intractable diseases with relation to RXRα, such as cancer and metabolic diseases, due to their potential activities on regulating the transcriptional activation function of RXRα. In addition, 1-6, 8, 10 and 12 (20μM) showed mild in vitro cytotoxicity against three cancer cell lines of ECA-109, Hela-S3 and PANC-1 with the inhibition rates arranging from 50% to 65%.

Natural Product Research published new progress about Antitumor agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Name: (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Floris, Patrick; McGillicuddy, Nicola; Morrissey, Brian; Albrecht, Simone; Kaisermayer, Christian; Hawe, David; Riordan, Lelia; Lindeberg, Anna; Forestell, Sean; Bones, Jonathan published the artcile< A LC-MS/MS platform for the identification of productivity markers in industrial mammalian cell culture media>, Application In Synthesis of 2873-36-1, the main research area is mammalian cell CHO cell.

Cell culture media formulations supplemented with soy hydrolyzates for com. scale manufacturing of therapeutic proteins were characterized by high-resolution LC-MS/MS to identify specific media components that contributed to cellular bioprocess variability. Initial untargeted screening of media formulations resulted in the combined quantification of >2500 features upon anal. by reversed-phase and hydrophilic interaction liquid chromatog. Chemometric evaluation of quantified features by Principal Component Anal. and Hierarchical Clustering revealed clear correlation between media lots and the corresponding hydrolyzates implemented during formulation development stages, suggesting that the observed variation in culture performance could be influenced by components present within hydrolyzates. Through multivariate data anal., a small number of dipeptides, identified as Tyrosyl-Leucine, Phenylalanyl-Valine and LL-Cyclo(Leucylprolyl) were determined in media as potential contributors to bioprocess variability due to their statistically significant higher abundance in formulations which yielded low cellular productivity. Subsequent quantification of these features was performed through targeted LC-QQQ-MS/MS which however, revealed discrepancies between dipeptide concentration levels in media and corresponding hydrolyzates presumably due to their potential instability upon interaction with other chem. defined components such as metals or chelating agents. The nutritional impact of the aforementioned features of interest on CHO cell growth performance was assessed through spiking studies in representative shake-flask cultures which however, failed to demonstrate clear correlation between dipeptide concentrations and achieved product yields further indicating the presence of a plausible synergetic effect between the identified dipeptides and alternative media components.

Process Biochemistry (Oxford, United Kingdom) published new progress about Growth (mammalian cell). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Application In Synthesis of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Ma, Haoran; Wang, Fuqian; Jin, Xiaoqi; Jiang, Jie; Hu, Song; Cheng, Lu; Zhang, Geng published the artcile< A new diketopiperazine from an endophytic fungus Aspergillus aculeatus F027>, Computed Properties of 2873-36-1, the main research area is diketopiperazine isolation structure Aspergillus; Aspergillus aculeatus ; diketopiperazine; endophytic fungus.

A new diketopiperazine cyclo-(L-Phe-N-ethyl-L-Glu), along with 2 known diketopiperazines cyclo-(L-Pro-L-Leu) and cyclo-(L-Pro-L-Phe) were isolated from the cultures of an endophytic fungus Aspergillus aculeatus F027. The structures of these compounds were elucidated based on spectroscopic data. The configurations of these compounds were determined by advanced Marfey’s anal. Antibacterial activity of the diketopiperazines against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were also evaluated.

Natural Product Research published new progress about Aspergillus aculeatus. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Computed Properties of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Zhao, Lijun; Duan, Feixia; Gong, Meng; Tian, Xue; Guo, Yan; Jia, Lirong; Deng, Sha published the artcile< (+)-Terpinen-4-ol Inhibits Bacillus cereus Biofilm Formation by Upregulating the Interspecies Quorum Sensing Signals Diketopiperazines and Diffusing Signaling Factors>, Related Products of 2873-36-1, the main research area is Bacillus biofilm formation terpinenol quorum sensing diketopiperazine; Bacillus cereus; EPS synthesis; biofilm inhibition; diffusing signaling factor; diketopiperazine; monocyclic monoterpenoids; quorum sensing; rpfB.

Bacillus cereus is a Gram-pos. endospore-forming foodborne pathogen that causes lethal food poisoning and significant economic losses, usually through biofilm- and endospore-induced recurrent cross- and postprocessing contamination. Due to the lack of critical inhibitory targets and control strategies, B. cereus biofilm contamination is a problem that urgently needs a solution In this study, the antibacterial and antibiofilm activities of several natural potential bacterial quorum sensing (QS) interferers, a group of spice-originated monoterpenoids, were screened, and terpinen-4-ol effectively inhibited B. cereus growth and biofilm and spore germination with min. growth inhibition and 50% biofilm inhibitory concentrations of 8 and 2μmol/mL, resp. FESEM/CLSM and phenotypic research illustrated that in addition to a decrease in the number of attached B. cereus cells, (+)-terpinen-4-ol also obviously reduced extracellular matrix synthesis, especially exopolysaccharides, and inhibited the swarming motility and protease activity of B. cereus. (+)-Terpinen-4-ol did not exert a significant effect on AI-2 signals in B. cereus. Accordingly, the B. cereus-produced interspecies QS signals diffusing signal factors (DSFs, C8-C15) and diketopiperazines (DKPs) were detected and identified here, which suppressed B. cereus biofilm formation in a concentration-dependent manner. (+)-Terpinen-4-ol significantly increased the levels of specific DSF and DKP signals in B. cereus and down-regulated the gene expression of some rpfB homologues in transcription level. Moreover, both DKPs and DSFs inhibited swarming motility and protease activity in B. cereus, while just the DSF signals 2-dodecenoic acid and 11-methyl-2-dodecenoic acid inhibited exopolysaccharide synthesis like (+)-terpinen-4-ol. In summary, B. cereus strains were found to produce nine DSF- and six DKP-type QS signaling mols., which repressed B. cereus biofilm formation. (+)-Terpinen-4-ol was confirmed to be a promising antibacterial and antibiofilm agent against B. cereus upregulating DSFs and DKPs levels, and it could target the critical genes rpfB for DSFs turnover.

Journal of Agricultural and Food Chemistry published new progress about Antibacterial agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Related Products of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Yeoh, Chiann Ying; Rosandy, Andi Rifki; Khalid, Rozida Mohd; Cheah, Yoke Kqueen published the artcile< Barrientosiimonas humi ethyl acetate extract exerts cytotoxicity against MCF-7 and MDA-MB-231 cells via induction of apoptosis and cell cycle arrest>, Formula: C11H18N2O2, the main research area is Barrientosiimonas ethyl acetate extract anticancer apoptosis cell cycle arrest.

To elucidate the cytotoxic effect of the secondary metabolites of Barrientosiimonas humi (B. humi) on MCF-7 and MDA-MB-231 human breast cancer cells and its underlying mechanisms of action. The extract was obtained from the fermentation of B. humi and fractionation of the crude extract was conducted via column chromatog. Cytotoxicity of the B. humi extract was determined by using MTT assay and real-time cellular anal. Morphol. changes, cell cycle profiles, mode of cell death, and caspase expressions of control and treated breast cancer cells were determined The Et acetate extract isolated from B. humi was cytotoxic against MCF-7 and MDA-MB-231 cell lines. One of the dichloromethane (DCM) fractions, designated as DCM-F2, exhibited the strongest activity among all the fractions and thereby was selected for further studies. DCM-F2 had selective cytotoxicity on target cells by inducing apoptosis, particularly in the early stage, and cell cycle arrest. Treated cells caused inhibition of cell cycle progression at 72 h leading to a significant increase (P < 0.05) in the G0/G1 population. DCM-F2 treated MDA-MB-231 cells showed caspase-dependent apoptosis, whereas DCM-F2 treated MCF-7 cells showed a caspase-independent apoptosis pathway. Five compounds were successfully isolated from B. humi. Cyclo (Pro-Tyr) was the most cytotoxic and selective compound against MCF-7 cells. B. humi Et acetate extract exhibits significant cytotoxicity against MCF-7 and MDA-MB-231 cells via induction of apoptosis and cell cycle arrest. Asian Pacific Journal of Tropical Biomedicine published new progress about Antitumor agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Formula: C11H18N2O2.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Huang, Ying; Zhang, Jeff; Yu, Zhengtian; Zhang, Hailong; Wang, Youzhen; Lingel, Andreas; Qi, Wei; Gu, Justin; Zhao, Kehao; Shultz, Michael D.; Wang, Long; Fu, Xingnian; Sun, Yongfeng; Zhang, Qiong; Jiang, Xiangqing; Zhang, Jiangwei; Zhang, Chunye; Li, Ling; Zeng, Jue; Feng, Lijian; Zhang, Chao; Liu, Yueqin; Zhang, Man; Zhang, Lijun; Zhao, Mengxi; Gao, Zhenting; Liu, Xianghui; Fang, Douglas; Guo, Haibing; Mi, Yuan; Gabriel, Tobias; Dillon, Michael P.; Atadja, Peter; Oyang, Counde published the artcile< Discovery of First-in-Class, Potent, and Orally Bioavailable Embryonic Ectoderm Development (EED) Inhibitor with Robust Anticancer Efficacy>, Application In Synthesis of 136866-30-3, the main research area is EED226 preparation polycomb repressive complex PRC2 EED inhibitor bioavailability.

Overexpression and somatic heterozygous mutations of EZH2, the catalytic subunit Polycomb repressive complex 2 (PRC2), are associated with several tumor types. EZH2 inhibitor, EPZ-6438 (Tazemetostat), demonstrated clin. efficacy in patients with acceptable safety profile as monotherapy. EED, another subunit of PRC2 complex, is essential for its histone methyltransferase activity through direct binding to trimethylated lysine 27 on histone 3 (H3K27Me3). Herein the authors disclose the discovery of a first-in-class potent, selective and orally bioavailable EED inhibitor EED226 (compound 43). Guided by x-ray crystallog., compound 43 discovered by fragmentation and regrowth of Compound (I), a PRC2 HTS hit that directly binds EED. Scaffold hopping followed by ensuing multi-parameter optimization led to the discovery compound 43. Compound 43 induces robust and sustained tumor regression in EZH2MUT pre-clin. DLBCL model. For the first time specific and direct inhibition of EED can be effective as an anti-cancer strategy.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 136866-30-3 belongs to class pyrazines, and the molecular formula is C4HCl2IN2, Application In Synthesis of 136866-30-3.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem