scholarly journals Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Study ◽  
Positive Control ◽  
Hydroxyl Group ◽  
Etoac Extract ◽  
The Third ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time

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).

scholarly journals Two New Cytotoxic Compounds from a Deep-Sea Penicillum citreonigrum XT20-134

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 509 ◽  
Author(s):  
Xi-Xiang Tang ◽  
Shun-Zhi Liu ◽  
Xia Yan ◽  
Bo-Wen Tang ◽  
Mei-Juan Fang ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Deep Sea ◽  
Cytotoxic Activities ◽  
Ionization Mass ◽  
Human Hepatoma ◽  
Etoac Extract ◽  
Deep Sea Sediment ◽  
Cytotoxic Compounds ◽  
Ic50 Values ◽  
New Compounds

Penicillum citreonigrum XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (1), 2-hydroxyl-3-pyrenocine-thio propanoic acid (2), ozazino-cyclo-(2,3-dihydroxyl-trp-tyr) (3), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (4), and 2,3,4-trihydroxybutyl cinnamate (5), together with 19 known compounds (6–24), were isolated from an ethyl acetate (EtOAc) extract of its fermentation. The structures of the new compounds were comprehensively characterized by high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). All isolates were evaluated for their cytotoxic activities. The heteroatom-containing new compounds 2 and 4 showed potent cytotoxicity to the human hepatoma tumor cell Bel7402 with IC50 values of 7.63 ± 1.46, 13.14 ± 1.41 μM and the human fibrosarcoma tumor cell HT1080 with IC50 values of 10.22 ± 1.32, 16.53 ± 1.67 μM, respectively.

Isoprenylated Phenolic Compounds from Morus macroura as Potent Tyrosinase Inhibitors

Planta Medica ◽  
2017 ◽  
Vol 84 (05) ◽  
pp. 336-343 ◽  
Author(s):  
Yifan Wang ◽  
Liangjin Xu ◽  
Wen Gao ◽  
Lixin Niu ◽  
Chunyue Huang ◽  
...  
Keyword(s):  
Kojic Acid ◽  
Positive Control ◽  
Diels Alder ◽  
Extensive Analysis ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Tyrosinase Inhibitors ◽  
Inhibitory Activities ◽  
New Compounds

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.

scholarly journals Butenolide Derivatives with α-Glucosidase Inhibitions from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 332 ◽  
Author(s):  
Zhongbin Cheng ◽  
Yuanli Li ◽  
Wan Liu ◽  
Lijun Liu ◽  
Jie Liu ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Mass Spectroscopy ◽  
Deep Sea ◽  
Aspergillus Terreus ◽  
Positive Control ◽  
Inhibitory Effects ◽  
Etoac Extract ◽  
Ring Compounds ◽  
Ic50 Values

Three new butenolide derivatives, namely aspernolides N–P (1–3), together with six known analogues (4–9), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungus Aspergillus terreus YPGA10. The structures of compounds 1–3 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound 1 represents the rare example of Aspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds 6–9 exhibited remarkable inhibitory effects against α-glucosidase with IC50 values of 3.87, 1.37, 6.98, and 8.06 μM, respectively, being much more active than the positive control acarbose (190.2 μM).

scholarly journals Chemical Constituents of the Deep-Sea-Derived Penicillium solitum

Marine Drugs ◽  
2021 ◽  
Vol 19 (10) ◽  
pp. 580
Author(s):  
Zhi-Hui He ◽  
Jia Wu ◽  
Lin Xu ◽  
Man-Yi Hu ◽  
Ming-Ming Xie ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Constituents ◽  
A549 Cells ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Positive Control ◽  
Ic50 Values ◽  
Penicillium Solitum ◽  
New Compounds

A systematic chemical investigation of the deep-sea-derived fungus Penicillium solitum MCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2 and 3), and 22 known (4–25) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (13) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC50 values of around 20 μM. Moreover, 13 displayed potent in vitro anti-food allergic activity with an IC50 value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (9) and penicopeptide A (10) showed moderate effects (IC50 = 50 and 58 μM, respectively).

scholarly journals Anti-Food Allergic Compounds from Penicillium griseofulvum MCCC 3A00225, a Deep-Sea-Derived Fungus

Marine Drugs ◽  
2021 ◽  
Vol 19 (4) ◽  
pp. 224
Author(s):  
Cui-Ping Xing ◽  
Dan Chen ◽  
Chun-Lan Xie ◽  
Qingmei Liu ◽  
Tian-Hua Zhong ◽  
...  
Keyword(s):  
Deep Sea ◽  
Spectroscopic Data ◽  
Positive Control ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ic50 Value ◽  
Penicillium Griseofulvum ◽  
New Compounds ◽  
Basophilic Leukemia

Ten new (1–10) and 26 known (11–36) compounds were isolated from Penicillium griseofulvum MCCC 3A00225, a deep sea-derived fungus. The structures of the new compounds were determined by detailed analysis of the NMR and HRESIMS spectroscopic data. The absolute configurations were established by X-ray crystallography, Marfey’s method, and the ICD method. All isolates were tested for in vitro anti-food allergic bioactivities in immunoglobulin (Ig) E-mediated rat basophilic leukemia (RBL)-2H3 cells. Compound 13 significantly decreased the degranulation release with an IC50 value of 60.3 μM, compared to that of 91.6 μM of the positive control, loratadine.

Inhibition of Protein Tyrosine Phosphatase 1B by Lutein Derivatives isolated from Mexican Oregano (Lippia graveolens)

2018 ◽  
Vol 17 (3) ◽  
pp. 134-139
Author(s):  
R.M. Perez-Gutierrez
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Methanol Extract ◽  
Tyrosine Phosphatase ◽  
Positive Control ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Ic50 Value ◽  
Ic50 Values

Methanol extract from Lippia graveolens (Mexican oregano) was studied in order to identify inhibitory bioactives for protein tyrosine phosphatase 1B (PTP1B). Known flavone as lutein (1), and another flavone glycoside such as lutein-7-o-glucoside (2), 6-hydroxy-lutein-7-ohexoside (3) and lutein-7-o-ramnoide (4) were isolated from methanol extract of aerial parts of the Lippia graveolens. All isolates were identified based on extensive spectroscopic data analysis, including UV, IR, NMR, MS and compared with spectroscopic data previously reported. These flavones were evaluated for PTP1B inhibitory activity. Among them, compounds 1 and 3 displayed potential inhibitory activity against PTP1B with IC50 values of 7.01 ± 1.25 μg/ml and 18.4 μg/ml, respectively. In addition, compound 2 and 4 showed moderate inhibitory activity with an IC50 value of 23.8 ± 6.21 and 67.8 ± 5.80 μg/ml respectively. Among the four compounds, luteolin was found to be the most potent PTP1B inhibitor compared to the positive control ursolic acid, with an IC50 value of 8.12 ± 1.06 μg/ml. These results indicate that flavonoids constituents contained in Lippia graveolens can be considered as a natural source for the treatment of type 2 diabetes.

Synthesis and Structure−Activity Relationship Studies of N-monosubstituted Aroylthioureas as Urease Inhibitors

2020 ◽  
Vol 16 ◽  
Author(s):  
Wei-Wei Ni ◽  
Hai-Lian Fang ◽  
Ya-Xi Ye ◽  
Wei-Yi Li ◽  
Li Liu ◽  
...  
Keyword(s):  
Regression Analysis ◽  
Mammalian Cells ◽  
Intact Cell ◽  
Linear Regression Analysis ◽  
Positive Control ◽  
Acetohydroxamic Acid ◽  
Urease Inhibitors ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Low Cytotoxicity

Background: Thiourea is a classical urease inhibitor usually as a positive control, and many N,N`-disubstituted thioureas have been determined as urease inhibitors. However, due to steric hindrance, N,N`-disubstituted thiourea motif could not bind urease as thiourea. On the contrary, N-monosubstituted thioureas with a tiny thiourea motif could theoretically bind into the active pocket as thiourea. Objective: A series of N-monosubstituted aroylthioureas were designed and synthesized for evaluation as urease inhibitors. Methods: Urease inhibition was determined by the indophenol method and IC50 values were calculated using computerized linear regression analysis of quantal log dose-probit functions. The kinetic parameters were estimated viasurface plasmon resonance (SPR) and by nonlinear regression analysis based on the mixed type inhibition model derived from Michaelis-Menten kinetics. Results: Compounds b2, b11and b19 reversibly inhibited urease with a mixed mechanism, and showed excellent potency against both cell-free urease and urease in intact cell, with IC50 values being 90-to 450-fold and 5-to 50-fold lower than the positive control acetohydroxamic acid, respectively. The most potent compound b11 showed IC50 value of 0.060 ±0.004μM against cell-free urease, which bound to urea binding site with a very low KDvalue (0.420±0.003nM) and a very long residence time (6.7 min). Compound b11was also demonstrated having very low cytotoxicity to mammalian cells. Conclusion: These results revealed that N-monosubstituted aroylthioureas clearly bind the active site of urease as expected, and represent a new class of urease inhibitors for the development of potential therapeutics against infections caused by ure-ase-containing pathogens.

scholarly journals Antifungal Activity of Chemical Constituents from Piper pesaresanum C. DC. and Derivatives against Phytopathogen Fungi of Cocoa

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3256
Author(s):  
Luis C. Chitiva-Chitiva ◽  
Cristóbal Ladino-Vargas ◽  
Luis E. Cuca-Suárez ◽  
Juliet A. Prieto-Rodríguez ◽  
Oscar J. Patiño-Ladino
Keyword(s):  
Antifungal Activity ◽  
Benzoic Acid ◽  
Chemical Constituents ◽  
Chemical Study ◽  
Positive Control ◽  
Positive Influence ◽  
Phytopathogenic Fungi ◽  
Phytochemical Study ◽  
Benzoic Acid Derivatives ◽  
First Time

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.

scholarly journals Study on α-glucosidase inhibitory activity of 40 kinds of vegetables, tubers, and fruits in An Giang

2021 ◽  
Vol 63 (4) ◽  
pp. 42-46
Author(s):  
Thi-My-Linh Lam ◽  
◽  
Minh-Tuan Le ◽  
Manh-Ha Bui ◽  
◽  
...  
Keyword(s):  
Glycine Max ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Syzygium Cumini ◽  
Inhibition Rate ◽  
Ic50 Value ◽  
Areca Catechu ◽  
Ic50 Values

A study on the α-glucosidase inhibitory activity of 40 kinds of vegetables, tubers, and fruits found in the An Giang province was conducted. The results indicated that all 40 extracted samples displayed α-glucosidase inhibitory activity at a concentration of 250 μg ml-1, 36 extracted samples showed an inhibition rate greater than 50% at 250 μg ml-1, 25 extracted samples had over 50% at 100 μg ml-1, 17 extracted samples possessed more than 50% at 50 μg ml-1, 7 extracted samples sampled showed over 50% at 25 μg ml-1, 5 extracted samples were greater than 50% at 10 μg ml-1, and 1 extracted sample was greater than 50% at 1 μg ml-1. Among the 40 samples, those taken from the seeds of Areca catechu, the fruits of Cassia grandis, the fruits of Syzygium cumini, the seeds of Glycine max,andthe stems of Enydra fluctuansexhibited the strongest α-glucosidase inhibitory activity in methanol, with IC50 values of 0.15, 2.54, 4.05, 5.17 and 8.68 μg ml-1, respectively, which were stronger than the positive control acarbose with an IC50 value of 214.5 μg ml-1

scholarly journals Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3927
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Ya-Hui Zhang ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Aspergillus Terreus ◽  
Epigenetic Modification ◽  
2D Nmr ◽  
Etoac Extract ◽  
One Dimensional ◽  
X Ray ◽  
Deacetylase Inhibitor ◽  
Ic50 Values ◽  
First Time ◽  
Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

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