scholarly journals Two New Altenusin/Thiazole Hybrids and a New Benzothiazole Derivative from the Marine Sponge-Derived Fungus Alternaria sp. SCSIOS02F49

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2844 ◽  
Author(s):  
Yaping Chen ◽  
Ruyan Chen ◽  
Jinhuai Xu ◽  
Yongqi Tian ◽  
Jiangping Xu ◽  
...  

Two novel altenusin-thiazole hybrids named altenusinoides A and B (1 and 2), a new benzothiazole derivative (3), and three known altenusin derivatives (4–6) have been obtained from the solid culture of the marine sponge-derived fungal strain, Alternaria sp. SCSIOS02F49. The structures of these new compounds were characterized by NMR, HRESIMS, and X-ray single crystal analysis. Compounds 1 and 2 possess an unusual altenusin-thiazole-fused skeleton core (6/6/5), and compound 3 represents the first benzothiazole derivative from fungi. Compounds 4 and 5 showed significant DPPH free-radical-scavenging activities with the prominent IC50 values of 10.7 ± 0.09 μM and 100.6 ± 0.025 μM, respectively. Additionally, compound 5 exhibited COX-2 inhibitory activity with an IC50 value of 9.5 ± 0.08 μM.

Marine Drugs ◽  
2018 ◽  
Vol 16 (8) ◽  
pp. 280 ◽  
Author(s):  
Xiaoyan Pang ◽  
Xiuping Lin ◽  
Pei Wang ◽  
Xuefeng Zhou ◽  
Bin Yang ◽  
...  

Seven new secondary metabolites classified as two perylenequinone derivatives (1 and 2), an altenusin derivative (3), two phthalide racemates (4 and 5), and two phenol derivatives (6 and 7), along with twenty-one known compounds (8–28) were isolated from cultures of the sponge-derived fungus, Alternaria sp. SCSIO41014. The structures and absolute configurations of these new compounds (1–7) were determined by spectroscopic analysis, X-ray single crystal diffraction, chiral-phase HPLC separation, and comparison of ECD spectra to calculations. Altertoxin VII (1) is the first example possessing a novel 4,8-dihydroxy-substituted perylenequinone derivative, while the phenolic hydroxy groups have commonly always substituted at C-4 and C-9. Compound 1 exhibited cytotoxic activities against human erythroleukemia (K562), human gastric carcinoma cells (SGC-7901), and hepatocellular carcinoma cells (BEL-7402) with IC50 values of 26.58 ± 0.80, 8.75 ± 0.13, and 13.11 ± 0.95 μg/mL, respectively. Compound 11 showed selectively cytotoxic activity against K562, with an IC50 value of 19.67 ± 0.19 μg/mL. Compound 25 displayed moderate inhibitory activity against Staphylococcus aureus with an MIC value of 31.25 μg/mL.


Antioxidants ◽  
2021 ◽  
Vol 10 (3) ◽  
pp. 370
Author(s):  
Xiao-Cui Zhuang ◽  
Gui-Lin Chen ◽  
Ye Liu ◽  
Yong-Li Zhang ◽  
Ming-Quan Guo

Warburgia ugandensis, also known as “green heart,” is widely used for the treatment of various diseases as a traditional ethnomedicinal plant in local communities in Africa. In this work, 9 and 12 potential superoxide dismutase (SOD) and xanthine oxidase (XOD) ligands from W. ugandensis were quickly screened out by combining SOD and XOD affinity ultrafiltration with LC-MS, respectively. In this way, four new lignanamides (compounds 11–14) and one new macrocyclic glycoside (compound 5), along with three known compounds (compounds 1, 3, and 7), were isolated and identified firstly in this species. The structures of the new compounds were elucidated by spectroscopic analysis, including NMR and UPLC-QTOF-MS/MS. Among these compounds, compound 14 showed the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-(3-ethylbenzthiazoline)-6-sulfonic acid (ABTS) radical scavenging activities, and total ferric-reducing antioxidant power (FRAP) with IC50 values of 6.405 ± 0.362 µM, 5.381 ± 0.092 µM, and 17.488 ± 1.625 mmol TE/g, respectively. Moreover, compound 14 displayed the highest inhibitory activity on cyclooxygenase-2 (COX-2) with IC50 value of 0.123 ± 0.004 µM, and the ranking order of other compounds’ IC50 values was 13 > 11 > 7 > 1 > 12. The present study suggested that lignanamides might represent interesting new characteristic functional components of W. ugandensis to exert remarkable antioxidant and anti-inflammatory activities. Moreover, compound 14, a new arylnaphthalene lignanamide, would be a highly potential natural antioxidant and anti-inflammatory agent from W. ugandensis.


Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).


Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2655 ◽  
Author(s):  
Lei ◽  
Lei ◽  
Zhou ◽  
Hu ◽  
Niu ◽  
...  

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.


2020 ◽  
Vol 21 (16) ◽  
pp. 5609
Author(s):  
Katarína Valachová ◽  
Mojmír Mach ◽  
Ladislav Šoltés

Indole derivatives such as isatin (a natural compound), cemtirestat, stobadine, and its derivatives (synthetic compounds) are known to have numerous positive effects on human health due to regulation of oxidative status. The aim of the study was to assess radical scavenging capacities of these compounds and explore their potential protective effects against reactive oxygen species formed during Cu(II) ions and ascorbate-induced degradation of high-molar-mass hyaluronan. Based on the IC50 values determined by the ABTS assay, the most effective compound was SM1M3EC2·HCl reaching the value ≈ 11 µmol/L. The lowest IC50 value reached in the DPPH assay was reported for cemtirestat ≈ 3 µmol/L. Great potency of inhibition of hyaluronan degradation was shown by cemtirestat, followed by isatin even at low concentration 10 µmol/L. On the other hand, stobadine·2HCl had also a protective effect on hyaluronan degradation, however at greater concentrations compared to cemtirestat or isatin. SME1i-ProC2·HCl reported to be a less effective compound and SM1M3EC2·HCl can be considered almost ineffective compared to stobadine·2HCl. In conclusion, our results showed that both isatin and cemtirestat were capable of attenuating the degradation of high-molar-mass hyaluronan due to their ability to complex/sequester cupric ions.


Planta Medica ◽  
2017 ◽  
Vol 84 (05) ◽  
pp. 336-343 ◽  
Author(s):  
Yifan Wang ◽  
Liangjin Xu ◽  
Wen Gao ◽  
Lixin Niu ◽  
Chunyue Huang ◽  
...  

AbstractThree new Diels-Alder adducts, macrourins E – G (1–3), one new 2-arylbenzofuran, macrourin H (4), and eight known Diels-Alder adducts (5–12) were isolated from Morus macroura. Their structures were elucidated through extensive analysis of spectroscopic data. The 1H NMR and ECD trends in the determination of the configurations of these Diels-Alder adducts were summarized. The tyrosinase inhibitory activities of all compounds isolated were evaluated, and the new compounds (1–4) as well as the eight known compounds (5–12) were found to be potent with IC50 values ranging from 0.39 to 4.54 µM. Among them, 1 showed the best tyrosinase inhibitory activity with an IC50 value of 0.39 µM, approximately 50 times stronger than the positive control, kojic acid.


Food Research ◽  
2021 ◽  
Vol 5 (2) ◽  
pp. 235-239
Author(s):  
M.S. Mpopo ◽  
M.K. Pillai ◽  
S.B. Mekbib

Searsia burchellii finds therapeutic applications in traditional medicine. Methanolic extracts, hexane, chloroform, ethyl acetate and methanol/water fractions of methanolic extracts and water extracts were obtained separately from the roots and leaves of Searsia burchellii by the combination of maceration, hot solvent extraction and solvent-solvent partition techniques. These extracts were evaluated for their antioxidant activity using 2,2- diphenyl-1-picrylhydrazil radical scavenging assay (DPPH). The extracts from roots and their fractions showed radical scavenging activity ranging from 6.60±4.50 to 63.27±1.93% at various concentrations. Similarly, the extracts from leaves and their fractions showed radical scavenging activity ranging from 3.32±0.95 to 64.91±0.15% at various concentrations. Ascorbic acid served as positive control which showed radical scavenging activity ranging from 53.62±2.80 to 60.82±0.62% at various concentrations. The IC50 values of these extracts and fractions were found to be < 200 to > 3000 µg/mL. The IC50 value of ascorbic acid was found to be <200 µg/mL. From this study, we concluded that extracts and their fractions from S. burchellii showed promising radical scavenging activity.


2018 ◽  
Vol 55 (5A) ◽  
pp. 134
Author(s):  
Ngo Minh Ngoc

Soybean (Glycine max) and soy milk residue (okara) are protein-rich materials. Soybean possesses the highest protein content among different types of beans (protein content of soybean varies from 40–42 %). Soy milk residue, a by-product of the soy milk manufacturing industry, contains approximately 27 % protein (by dry weight). A number of recent studies have investigated the improvement of functional properties of protein contained in soybean and okara by fermentation or by the use of proteolytic enzymes. The aim of this study was to evaluate the antioxidant activities of soybean and okara hydrolysates obtained by the fermentation with Aspergillus oryzae or by using proteolytic enzymes (neutrase and flavourzyme). DPPH radical scavenging assay was used to determine the antioxidant activities of hydrolysates. The concentration of peptides required to scavenge DPPH radical by 50 % (IC50 value) was used to evaluate the antioxidant activity of peptides produced obtained from hydrolysates. The results showed that when fermented with A. oryzae, the okara hydrolysate had higher antioxidant activity than the soybean hydrolysate, with IC50 values of 0.447 mg/ml and 3.95 mg/ml, respectively. The hydrolyzed okara obtained from hydrolysis using Neutrase had higher antioxidant activity than the one obtained from hydrolysis using Flavourzyme, with IC50 values of0.200 mg/ml and 0.407 mg/ml, respectively. Different peptide fractions obtained from the hydrolysates using cut-off membrane (10 kDa, 3 kDa and 1 kDa) possessed different antioxidant activities. The < 1 kDa peptide fraction exhibited the highest antioxidant activity with an IC50 value of 0.158 mg/ml.


2019 ◽  
Vol 18 (4) ◽  
pp. 99-107
Author(s):  
Cang H. Mai

This study examined factors affecting on chlorophyll extraction from Egyptian Luffa leaf for using as food colorant. Optimal conditions for chlorophyll extraction were ethanol 96% for 97 minutes at 49oC and extraction speed at 123 rpm. The quality of extracts was investigated for microorganisms, heavy metals and antioxidant activity by using the DPPH (2-2-diphenyl-1- DPPH) method. The free radical scavenging activities of extract presented by the IC50 value was 261,7 μg/mL.


1970 ◽  
Vol 2 (1) ◽  
pp. 32-36
Author(s):  
Israt Jahan Biva ◽  
Md Mynol Islam Vhuiyan ◽  
Moni Rani Saha ◽  
Muhammad Shahidul Islam ◽  
Shammy Sarwar

n-Hexane, chloroform and methanol soluble extracts of the leaves of Annona squamosa were screened fortheir possible antioxidant activitiy by DPPH free radical scavenging and cytotoxicity by brine shrimp lethalitybioassay. In DPPH radical scavenging assay, methanol soluble extract was found to be the most potent withan IC50 value of 103.5 μg/ml. The amount of total phenolics was also found to the highest in the methanolsoluble extract (283.16 ± 8.90 mg/g), followed by chloroform soluble extract (216.90 ± 4.48 mg/g). Here BHTand ascorbic acid were used as standards with IC50 values 8.2 μg/ml and 25 μg/ml respectively. In the brineshrimp lethality bioassay, the most significant cytotoxicity was observed with chloroform soluble extract withan LC50 of 4.16 μg/ml where vincristine sulphate was used as standard (LC50 0.29 μg/ml).Key Words: Annona squamosa; DPPH; Folin-Ciocalteu Reagent; Phenolic Contents; Brine ShrimpDOI: 10.3329/sjps.v2i1.5813Stamford Journal of Pharmaceutical Sciences Vol.2(1) 2009: 32-36


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