18875-42-8Relevant articles and documents
WSS2220, a novel cyclic tetrapeptide with a new sulfonoamino acid, exhibits potent and selective inhibitory activity against GlyT1
Terui, Yuichi,Yi-wen, Chu,Jun-ying, Li,Nozawa, Osamu,Ando, Tsutomu,Fukunaga, Takuya,Aoki, Takeshi,Toda, Yoshihisa,Kawashima, Akira
, p. 3067 - 3070 (2008)
In the course of our screening program for novel glycine transporter inhibitors, we obtained a novel cyclic tetrapeptide (WSS2220) from the culture broth of Nonomuraea sp. The structure of WSS2220 was elucidated based on physicochemical data. WSS2220 contained a novel amino acid (4-oxo-3′-sulfoisoleucine), the absolute stereochemistry of which was determined by chemical modifications and the modified Mosher's method. WSS2220 selectively inhibited glycine transporter type1 with an IC50 of 20 nM.
Anti-Cryptococcus Phenalenones and Cyclic Tetrapeptides from Auxarthron pseudauxarthron
Li, Yan,Yue, Qun,Jayanetti, Dinith R.,Swenson, Dale C.,Bartholomeusz, Geoffrey A.,An, Zhiqiang,Gloer, James B.,Bills, Gerald F.
, p. 2101 - 2109 (2017)
Auxarthrones A-E (1-5), five new phenalenones, and two new naturally occurring cyclic tetrapeptides, auxarthrides A (7) and B (8), were obtained from three different solvent extracts of cultures of the coprophilous fungus Auxarthron pseudauxarthron. Auxarthrones C (3) and E (5) possess an unusual 7a,8-dihydrocyclopenta[a]phenalene-7,9-dione ring system that has not been previously observed in natural products. Formation of 1-5 was found to be dependent on the solvent used for culture extraction. The structures of these new compounds were elucidated primarily by analysis of NMR and MS data. Auxarthrone A (1) was obtained as a mixture of chromatographically inseparable racemic diastereomers (1a and 1b) that cocrystallized, enabling confirmation of their structures by X-ray crystallography. The absolute configurations of 7 and 8 were assigned by analysis of their acid hydrolysates using Marfey's method. Compound 1 displayed moderate antifungal activity against Cryptococcus neoformans and Candida albicans, but did not affect human cancer cell lines.
Enhancing the intestinal absorption of molecules containing the polar guanidino functionality: A double-targeted prodrug approach
Sun, Jing,Dahan, Arik,Amidon, Gordon L.
, p. 624 - 632 (2010)
A prodrug strategy was applied to guanidino-containing analogues to increase oral absorption via hPEPT1 and hVACVase. L-Valine, L-isoleucine, and L-phenylalanine esters of [3-(hydroxymethyl)-phenyl]guanidine (3-HPG) were synthesized and evaluated for transport and activation. In HeLa/ hPEPT1 cells, Val-3-HPG and Ile-3-HPG exhibited high affinity to hPEPT1 (IC50: 0.65 and 0.63 mM, respectively), and all three L-amino acid esters showed higher uptake (2.6- to 9-fold) than the parent compound 3-HPG. Val-3-HPG and Ile-3-HPG demonstrated remarkable Caco-2 permeability enhancement, and Val-3-HPG exhibited comparable permeability to valacyclovir. In rat perfusion studies, Val-3-HPG and Ile-3-HPG permeabilities were significantly higher than 3-HPG and exceeded/matched the high-permeability standard metoprolol, respectively. All the L-amino acid 3-HPG esters were effectively activated in HeLa and Caco-2 cell homogenates and were found to be good substrates of hVACVase (k cat/Km in mM-1 · s-1: Val-3-HPG, 3370; Ile-3-HPG, 1580; Phe-3-HPG, 1660). In conclusion, a prodrug strategy is effective at increasing the intestinal permeability of polar guanidino analogues via targeting hPEPT1 for transport and hVACVase for activation.
Cystargolides, 20S proteasome inhibitors isolated from Kitasatospora cystarginea
Gill, Krista A.,Berrué, Fabrice,Arens, Jennifer C.,Carr, Gavin,Kerr, Russell G.
, p. 822 - 826 (2015)
Two novel β-lactone-containing natural products, cystargolides A (1) and B (2), were isolated from the actinomycete Kitasatospora cystarginea. The production of these two natural products was highlighted using a methodology associating liquid chromatography-high-resolution mass spectrometry (LC-HRMS) analysis and the statistical analysis tool principal component analysis (PCA). Their structures were elucidated by interpretation of NMR experiments and tandem mass spectrometry. The absolute configurations of the amino acid residues were determined using Marfey's method, and the relative configurations of the β-lactone substituents were determined on the basis of the vicinal 3JHH coupling value. Due to the presence of the β-lactone, 1 and 2 were evaluated for their ability to inhibit the human 20S proteasome. 1 and 2 both inhibited the 20S proteasome in vitro with IC50 values of 0.35 and 0.93 μM, respectively.
Enantioselective hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives
Claverie, Jerome,Tang, Chuyan,Tang, Wenjun,Wan, Feng,Wang, Nan,Zhu, Yuxin
, p. 5546 - 5549 (2021)
An efficient asymmetric hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives has been achieved with a Rh-ArcPhos catalyst, affording a series of α-acylamino-β-alkyl tetrahydropyranones with two contiguous chiral centers in up to 96% ee and 1000 TON.
Isolation and structure determination of a new cytotoxic peptide, curacozole, from Streptomyces curacoi based on genome mining
Kaweewan, Issara,Komaki, Hisayuki,Hemmi, Hikaru,Hoshino, Kanata,Hosaka, Takeshi,Isokawa, Gouchi,Oyoshi, Takanori,Kodani, Shinya
, p. 1 - 7 (2019)
Using genome mining, a new cytotoxic peptide named curacozole was isolated from Streptomyces curacoi. Through ESI-MS and NMR analyses, curacozole was determined to be a macrocyclic peptide containing two isoleucine, two thiazole and three oxazole moieties. Curacozole exhibited potent cytotoxic activity against HCT116 and HOS cancer cells. The proposed biosynthetic gene cluster of curacozole was identified and compared with that of the related compound YM-216391.
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.
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.
