scholarly journals Isolation and Identification of the Antimicrobial Agent Beauvericin from the EndophyticFusarium oxysporum5-19 with NMR and ESI-MS/MS

2016 ◽  
Vol 2016 ◽  
pp. 1-4 ◽  
Author(s):  
Huawei Zhang ◽  
Chuanfen Ruan ◽  
Xuelian Bai ◽  
Miao Zhang ◽  
Shuangshuang Zhu ◽  
...  

Endophytic microbe has been proved to be one of rich sources of bioactive natural products with potential application for new drug and pesticide discovery. One cyclodepsipeptide, beauvericin, was firstly isolated from the fermentation broth ofFusarium oxysporum5-19 endophytic onEdgeworthia chrysanthaLinn. Its chemical structure was unambiguously identified by a combination of spectroscopic methods, such as HRESI-MS and1H and13C NMR. ESI-MS/MS was successfully used to elucidate the splitting decomposition route of the positive molecule ion of beauvericin. Antimicrobial results showed that this cyclodepsipeptide had inhibitory effect on three human pathogenic microbes,Candida albicans,Escherichia coli, andStaphylococcus aureus. In particular, beauvericin exhibited the strongest antimicrobial activity againstS. aureuswith MIC values of 3.91 μM, which had similar effect with that of the positive control amoxicillin.

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly


AMB Express ◽  
2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Junhyok Ryang ◽  
Yan Yan ◽  
Yangyang Song ◽  
Fang Liu ◽  
Tzi Bun Ng

AbstractIn this study, a single component paclitaxel was obtained from fermentation broth by molecular imprinting technique, and its antiviral, antitumor and immunomodulatory activities were studied. The results showed that paclitaxel had a good inhibitory activity on human breast cancer MCF-7 cells and showed a concentration- dependent relationship with an IC50 of about 15 μg/mL in the sulforhodamine B assay. At the same time, paclitaxel exerted a weak inhibitory activity on cervical cancer Hela cells. In addition, paclitaxel not only inhibited the invasion of HIV-1 pseudovirus into cells, but also exhibited inhibitory activity to a certain extent after viral invasion of the cells. At a paclitaxel concentration of 20 μg/mL, the inhibition of HIV-1 pseudovirus reached about 66%. The inhibition of HIV-1 protease activity was concentration-dependent. At a concentration of 20 μg/mL, the inhibitory effect of paclitaxel on HIV-1 protease was similar to that of the positive control pepstatin A, being 15.8%. The HIV-1 integrase inhibiting activity of paclitaxel was relatively weak. Paclitaxel significantly up-regulated the expression of interleukin-6.


2003 ◽  
Vol 58 (1-2) ◽  
pp. 11-16 ◽  
Author(s):  
Liselotte Krenn ◽  
Anca Miron ◽  
Enne Pemp ◽  
Ursula Petr ◽  
Brigitte Kopp

The detailed investigation of a methanolic extract of aerial parts of Achillea nobilis resulted in the isolation of 10 flavonoids. A new C-glycosylflavone, luteolin-6-C-apiofuranosyl-(1‴→2″)-glucoside, was isolated besides orientin, isoorientin, vitexin, isoschaftoside, luteolin- 7-O-β-glucuronide, luteolin-4′-O-β-glucoside and quercetin-3-O-methyl ether and two rare flavonolglycosides, quercetin-3-O-α-arabinosyl-(1‴→6″ )-glucoside and quercetin-3-O-methylether-7-O-β-glucoside. The structures were established either by comparison with authentic substances or by UV, 1H NMR and 13C NMR spectroscopic methods including 2ᴅ-NMR techniques and ESI-MS


2007 ◽  
Vol 2 (10) ◽  
pp. 1934578X0700201
Author(s):  
Irena Matławska ◽  
Maria Sikorska ◽  
Nabil H. El-Sayed ◽  
Jaromir Budzianowski ◽  
Elżbieta Hołderna-Kędzia ◽  
...  

Two flavones, hypolaetin 8- O-β-glucuronopyranoside 3″- O-sulfate and isoscutellarein 8- O-β-glucuronopyranoside 3″-O-sulfate, together with hypolaetin 8- O-β-glucuronopyranoside, kaempferol 3- O-α-rhamnopyranosyl (1“→6′”)-β-glucopyranoside and quercetin 3- O-α-rhamnopyranosyl (1″→6″”)-β-glucopyranoside were isolated from the leaves of Abutilon indicum, and their structures elucidated by acid hydrolysis and spectroscopic methods, including HPLC/ESI-MS, and 1H, 13C NMR, COSY, HMQC, HSQC and HMBC spectroscopic experiments. The antimicrobial activity of hypolaetin 8- O-β-glucuronopyranoside 3″- O-sulfate and of isoscutellarein 8- O-β-glucuronopyranoside 3″- O-sulfate against Staphylococcus aureus was confirmed.


2017 ◽  
Vol 12 (7) ◽  
pp. 1934578X1701200
Author(s):  
Isaraporn Polbuppha ◽  
Wisanu Maneerat ◽  
Tawanun Sripisut ◽  
Thunwadee Limtharakul (née Ritthiwigrom) ◽  
Sarot Cheenpracha ◽  
...  

The first phytochemical investigation of the twig extracts of Maclura fruticosa led to the isolation and identification of a new xanthone, maclurafruticosone (1), together with 14 known compounds (2–15). All compounds were elucidated using spectroscopic methods as well as through comparisons made with data reported in the literature. Some isolated compounds were evaluated for their antioxidant, α-glucosidase inhibitory and cytotoxic activities. Compound 4, 6 and 7 showed significant antioxidant activity against DPPH radicals with IC50 values ranging from 7.45–16.12 μM. Compound 4 also exhibited potent activity against ABTS•+ scavenging activity with an IC50 value of 0.55 ± 0.01 μM which was better than positive control (ascorbic acid, IC50 2.35 ± 0.17 μM). Compound 12 showed significant α-glucosidase inhibitory activity with an IC50 value of 0.02 ± 0.37 mM. Compounds 5, 6 and 12 showed weak cytotoxic activities against a colon cancer cell line with IC50 values ranging from 22.35–47.62 μM.


2021 ◽  
Vol 10 (1) ◽  
pp. 189-200
Author(s):  
Yuan She ◽  
Chong Zou ◽  
Shiwei Liu ◽  
Keng Wu ◽  
Hao Wu ◽  
...  

Abstract Thermoanalysis was used in this research to produce a comparative study on the combustion and gasification characteristics of semi-coke prepared under pyrolytic atmospheres rich in CH4 and H2 at different proportions. Distinctions of different semi-coke in terms of carbon chemical structure, functional groups, and micropore structure were examined. The results indicated that adding some reducing gases during pyrolysis could inhibit semi-coke reactivity, the inhibitory effect of the composite gas of H2 and CH4 was the most observable, and the effect of H2 was higher than that of CH4; moreover, increasing the proportion of reducing gas increased its inhibitory effect. X-ray diffractometer and Fourier-transform infrared spectrometer results indicated that adding reducing gases in the atmosphere elevated the disordering degree of carbon microcrystalline structures, boosted the removal of hydroxyl- and oxygen-containing functional groups, decreased the unsaturated side chains, and improved condensation degree of macromolecular networks. The nitrogen adsorption experiment revealed that the types of pore structure of semi-coke are mainly micropore and mesopore, and the influence of pyrolytic atmosphere on micropores was not of strong regularity but could inhibit mesopore development. Aromatic lamellar stack height of semi-coke, specific surface area of mesopore, and pore volume had a favorable linear correlation with semi-coke reactivity indexes.


Planta Medica ◽  
2021 ◽  
Author(s):  
Birgit Waltenberger ◽  
Françoise Lohézic-Le Dévéhat ◽  
Thi Huyen Vu ◽  
Olivier Delalande ◽  
Claudia Lalli ◽  
...  

AbstractProtein tyrosine phosphatase 1B plays a significant role in type 2 diabetes mellitus and other diseases and is therefore considered a new drug target. Within this study, an acetone extract from the lichen Stereocaulon evolutum was identified to possess strong protein tyrosine phosphatase 1B inhibition in a cell-free assay (IC50 of 11.8 µg/mL). Fractionation of this bioactive extract led to the isolation of seven known molecules belonging to the depsidones and the related diphenylethers and one new natural product, i.e., 3-butyl-3,7-dihydroxy-5-methoxy-1(3H)-isobenzofurane. The isolated compounds were evaluated for their inhibition of protein tyrosine phosphatase 1B. Two depsidones, lobaric acid and norlobaric acid, and the diphenylether anhydrosakisacaulon A potently inhibited protein tyrosine phosphatase 1B with IC50 values of 12.9, 15.1, and 16.1 µM, respectively, which is in the range of the protein tyrosine phosphatase 1B inhibitory activity of the positive control ursolic acid (IC50 of 14.4 µM). Molecular simulations performed on the eight compounds showed that i) a contact between the molecule and the four main regions of the protein is required for inhibitory activity, ii) the relative rigidity of the depsidones lobaric acid and norlobaric acid and the reactivity related to hydrogen bond donors or acceptors, which interact with protein tyrosine phosphatase 1B key amino acids, are involved in the bioactivity on protein tyrosine phosphatase 1B, iii) the cycle opening observed for diphenylethers decreased the inhibition, except for anhydrosakisacaulon A where its double bond on C-8 offsets this loss of activity, iv) the function present at C-8 is a determinant for the inhibitory effect on protein tyrosine phosphatase 1B, and v) the more hydrogen bonds with Arg221 there are, the more anchorage is favored.


Foods ◽  
2021 ◽  
Vol 10 (7) ◽  
pp. 1466
Author(s):  
Hafiz Rehan Nadeem ◽  
Saeed Akhtar ◽  
Tariq Ismail ◽  
Piero Sestili ◽  
Jose Manuel Lorenzo ◽  
...  

Heterocyclic aromatic amines (HAAs) are potent carcinogenic compounds induced by the Maillard reaction in well-done cooked meats. Free amino acids, protein, creatinine, reducing sugars and nucleosides are major precursors involved in the production of polar and non-polar HAAs. The variety and yield of HAAs are linked with various factors such as meat type, heating time and temperature, cooking method and equipment, fresh meat storage time, raw material and additives, precursor’s presence, water activity, and pH level. For the isolation and identification of HAAs, advanced chromatography and spectroscopy techniques have been employed. These potent mutagens are the etiology of several types of human cancers at the ng/g level and are 100- to 2000-fold stronger than that of aflatoxins and benzopyrene, respectively. This review summarizes previous studies on the formation and types of potent mutagenic and/or carcinogenic HAAs in cooked meats. Furthermore, occurrence, risk assessment, and factors affecting HAA formation are discussed in detail. Additionally, sample extraction procedure and quantification techniques to determine these compounds are analyzed and described. Finally, an overview is presented on the promising strategy to mitigate the risk of HAAs by natural compounds and the effect of plant extracts containing antioxidants to reduce or inhibit the formation of these carcinogenic substances in cooked meats.


2006 ◽  
Vol 10 (11) ◽  
pp. 1301-1308 ◽  
Author(s):  
Eva H. Mørkved ◽  
Nils K. Afseth ◽  
Helge Kjøsen

The Zn ( quinoline )2 Cl 2 complex is found to be a convenient reagent for the direct synthesis of amino-substituted, zinc azaphthalocyanines. Octa(4-thiomorpholinyl)- and octa(1-pyrazolyl)- substituted zinc azaphthalocyanines were synthesized from pyrazines, 5,6-bis(4-thiomorpholinyl)pyrazine-2,3-dicarbonitrile and 5,6-bis(1-pyrazolyl)pyrazine-2,3-dicarbonitrile, respectively and dry Zn ( quinoline )2 Cl 2. Two zinc azaphthalocyanines, both mixtures of four constitutional isomers, were synthesized by the same method, from 6-(2-thienyl)-5-(4-thiomorpholinyl)pyrazine-2,3-dicarbonitrile and from 6-(2-thienyl)-5-(1-pyrazolyl)pyrazine-2,3-dicarbonitrile respectively. The octa(4-thiomorpholinyl)- and octa(1-pyrazolyl)-substituted zinc azaphthalocyanines and the zinc azaphthalocyanines with mixed substituents were characterized by elemental analyses, TOF-SIMS, 1 H and 13 C NMR, and UV-vis spectroscopic methods. Q-bands for octa(4-thiomorpholinyl)- and octa(1-pyrazolyl)-substituted zinc azaphthalocyanines and the zinc azaphthalocyanines with mixed substituents are found at respectively 655 and 670 nm (ɛ: 100 000-180 000 M-1.cm-1).


Endocrinology ◽  
2005 ◽  
Vol 146 (3) ◽  
pp. 1532-1540 ◽  
Author(s):  
Anne Florin ◽  
Magali Maire ◽  
Aline Bozec ◽  
Ali Hellani ◽  
Sonia Chater ◽  
...  

In the present study we investigated whether fetal exposure to flutamide affected messenger and protein levels of claudin-11, a key Sertoli cell factor in the establishment of the hemotesticular barrier, at the time of two key events of postnatal testis development: 1) before puberty (postnatal d 14) during the establishment of the hemotesticular barrier, and 2) at the adult age (postnatal d 90) at the time of full spermatogenesis. The data obtained show that claudin-11 expression was inhibited in prepubertal rat testes exposed in utero to 2 and 10 mg/kg·d flutamide. However, in adult testes, the inhibition was observed only with 2, and not with 10, mg/kg·d of the antiandrogen. It is shown here that these differences between prepubertal and adult testes could be related to dual and opposed regulation of claudin-11 expression resulting from positive control by androgens and an inhibitory effect of postmeiotic germ cells. Indeed, testosterone is shown to stimulate claudin-11 expression in cultured Sertoli cells in a dose- and time-dependent manner (maximum effect with 0.06 μm after 72 h of treatment). In contrast, postmeiotic germ cells potentially exert a negative effect on claudin-11 expression, because adult rat testes depleted in spermatids (after local irradiation) displayed increased claudin-11 expression, whereas in a model of cocultured Sertoli and germ cells, spermatids, but not spermatocytes, inhibited claudin-11 expression. The apparent absence of claudin-11 expression changes in adult rat testes exposed to 10 mg/kg·d flutamide therefore could result from the antagonistic effects of 1) the inhibitory action of the antiandrogen and 2) the stimulatory effect of the apoptotic germ cells on claudin-11 expression. Together, due to the key role of claudin-11 in the hemotesticular barrier, the present findings suggest that such regulatory mechanisms may potentially affect this barrier (re)modeling during spermatogenesis.


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