scholarly journals Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5273
Author(s):  
Shouye Han ◽  
Yu Liu ◽  
Wan Liu ◽  
Fan Yang ◽  
Jia Zhang ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Positive Control ◽  
Marine Fungus ◽  
Fungal Strain ◽  
Side Chain ◽  
Chromone Derivatives ◽  
Ic50 Values ◽  
Carbon Side Chain

The fungal strain YPGA3 was isolated from the sediments of the Yap Trench and identified as Penicillium thomii. Eight new chromone derivatives, named penithochromones M−T (1–8), along with two known analogues, 9 and 10, were isolated from the strain. The structures were established by detailed analyses of the spectroscopic data. The absolute configuration of the only chiral center in compound 1 was tentatively determined by comparing the experimental and the calculated specific rotations. Compounds 7 and 8 represent the first examples of chromone derivatives featuring a 5,7-dioxygenated chromone moiety with a 9-carbon side chain. Bioassay study revealed that compounds 6–10 exhibited remarkable inhibition against α-glucosidase with IC50 values ranging from 268 to 1017 μM, which are more active than the positive control acarbose (1.3 mmol).

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.

scholarly journals Secondary Metabolites with α-Glucosidase Inhibitory Activity from the Mangrove Fungus Mycosphaerella sp. SYSU-DZG01

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 483 ◽  
Author(s):  
Pei Qiu ◽  
Zhaoming Liu ◽  
Yan Chen ◽  
Runlin Cai ◽  
Guangying Chen ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Secondary Metabolites ◽  
Single Crystal ◽  
Absolute Configuration ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
X Ray Diffraction ◽  
X Ray ◽  
Ic50 Values ◽  
New Metabolites

Four new metabolites, asperchalasine I (1), dibefurin B (2) and two epicoccine derivatives (3 and 4), together with seven known compounds (5–11) were isolated from a mangrove fungus Mycosphaerella sp. SYSU-DZG01. The structures of compounds 1–4 were established from extensive spectroscopic data and HRESIMS analysis. The absolute configuration of 1 was deduced by comparison of ECD data with that of a known structure. The stereostructures of 2–4 were further confirmed by single-crystal X-ray diffraction. Compounds 1, 8 and 9 exhibited significant α-glucosidase inhibitory activity with IC50 values of 17.1, 26.7 and 15.7 μM, respectively. Compounds 1, 4, 6 and 8 showed antioxidant activity by scavenging DPPH· with EC50 values ranging from 16.3 to 85.8 μM.

scholarly journals Inhibitory Effects of Secondary Metabolites from the Lichen Stereocaulon evolutum on Protein Tyrosine Phosphatase 1B

Planta Medica ◽  
2021 ◽  
Author(s):  
Birgit Waltenberger ◽  
Françoise Lohézic-Le Dévéhat ◽  
Thi Huyen Vu ◽  
Olivier Delalande ◽  
Claudia Lalli ◽  
...  
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Tyrosine Phosphatase ◽  
Inhibitory Effect ◽  
Positive Control ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Ic50 Values ◽  
A Cell

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.

scholarly journals New Chromones from a Marine-Derived Fungus, Arthrinium sp., and Their Biological Activity

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1982 ◽  
Author(s):  
Jie Bao ◽  
Fei He ◽  
Jin-Hai Yu ◽  
Huijuan Zhai ◽  
Zhi-Qiang Cheng ◽  
...  
Keyword(s):  
Biological Activity ◽  
Deep Sea ◽  
Spectroscopic Data ◽  
Radical Scavenging ◽  
Antioxidant Property ◽  
Electronic Circular Dichroism ◽  
Chromone Derivatives ◽  
Ic50 Values ◽  
Ester Method ◽  
The Absolute

Five new chromone derivatives, arthones A–E (1–5), together with eight known biogenetically related cometabolites (6–13), were isolated from a deep-sea-derived fungus Arthrinium sp. UJNMF0008. Their structures were assigned by detailed analyses of spectroscopic data, while the absolute configurations of 1 and 5 were established by electronic circular dichroism (ECD) calculations and that of 2 was determined by modified Mosher ester method. Compounds 3 and 8 exhibited potent antioxidant property with DPPH and ABTS radical scavenging activities, with IC50 values ranging from 16.9 to 18.7 μM. Meanwhile, no compounds indicated obvious bioactivity in our antimicrobial and anti-inflammatory assays at 50.0 μM.

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 Dimeric 1,4-benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus Penicillium sp. L129

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 383 ◽  
Author(s):  
Zhang ◽  
Ju ◽  
Li ◽  
Sun ◽  
Peng ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Cell Lines ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Cytotoxic Activities ◽  
Penicillium Sp ◽  
Ic50 Values ◽  
Cytotoxicity Activities ◽  
Mic Value ◽  
Mcf 7

Two new dimeric 1,4-benzoquinone derivatives, peniquinone A (1) and peniquinone B (2), a new dibenzofuran penizofuran A (3), and a new pyrazinoquinazoline derivative quinadoline D (4), together with 13 known compounds (5–17), were isolated from a marine-derived fungus Penicillium sp. L129. Their structures, including absolute configurations, were elucidated by extensive spectroscopic data and electronic circular dichroism calculations. Compound 1 exhibited cytotoxicity against the MCF-7, U87 and PC3 cell lines with IC50 values of 12.39 µM, 9.01 µM and 14.59 µM, respectively, while compound 2 displayed relatively weak cytotoxicity activities against MCF-7, U87 and PC3 cell lines with IC50 values of 25.32 µM, 13.45 µM and 19.93 µM, respectively. Furthermore, compound 2 showed weak quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with an MIC value of 20 μg/well.

scholarly journals Chemical constituents and their alpha-glucosidase inhibitory activity of Solanum procumbens

2021 ◽  
Vol 5 (3) ◽  
pp. 1326-1333
Author(s):  
Nhan Trung Nguyen ◽  
Truong Nhat Van Do ◽  
Tho Huu Le ◽  
Phu Hoang Dang ◽  
Hai Xuan Nguyen ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Positive Control ◽  
Scientific Data ◽  
Chemical Compositions ◽  
Chromatography Method ◽  
Perennial Shrub ◽  
Ic50 Values ◽  
Folk Remedies

Solanum procumbens called ``Cà gai leo'' in Vietnam, belonged to the family of Solanaceae, which is a prickly diffuse, bright green perennial shrub, woody at the base. This plant has been sought for plenty of Vietnamese folk remedies for diseases such as rheumatism, back pain, detoxification, cough, pain relief, hemostasis, hepatitis, and cirrhosis. Chemical reports revealed the presence of lots of secondary metabolites such as steroids, triterpenoids, alkaloids, and phenolic compounds that have good biological activities such as antibacterial, antidiabetic, antioxidant, and antimicrobial... By column chromatography method together with thin layer normal-phase chromatography on the ethyl acetate extract of its entire plant, we isolated four compounds including dioscin (1), b -sitosterol (2), daucosterol (3) and 6'-O-acetyl-b -daucosterol (4). The result of theira-glucosidase inhibitory activity showed that compounds 2 and 4 had strong inhibition with IC50 values of 35.2 and 209.5 mM, comparing to the positive control, acarbose with an IC50 value of 214.5 mM. The results of this study have contributed to the scientific data of chemical compositions of Vietnamese medicinal plants, among them S. procumbens would potentially be developed as a plant-based drug to decrease the blood glucose level.

scholarly journals Chemical constituents and their alpha-glucosidase inhibitory activity from the stems of taxotrophis ilicifolius

2021 ◽  
Vol 5 (3) ◽  
pp. 1334-1340
Author(s):  
Truong Nhat Van Do ◽  
Hai Xuan Nguyen ◽  
Tho Huu Le ◽  
Mai Thanh Thi Nguyen
Keyword(s):  
Inhibitory Activity ◽  
Chemical Constituents ◽  
Syringic Acid ◽  
Positive Control ◽  
Traditional Use ◽  
Chromatography Method ◽  
Chemical Structures ◽  
Phenolic Constituents ◽  
Ic50 Values ◽  
Treatment Of Diabetes

Taxotrophis ilicifolius, called "Gai quít" in Vietnam, belonged to the family of Moraceae. The stems of T. ilicifolius are used in traditional medicine to cure pimples, anti-inflammatory, antibacterial... By column chromatography method together with thin layer chromatography on the ethyl acetate extract of its stems, six compounds were isolated including wogonin (1), 4-hydroxybenzoic acid (2), vanillic acid (3), vanillin (4), syringic acid (5), and syringaldehyde (6). Their chemical structures were elucidated by extensive NMR spectroscopic analysis and comparison with the literature data. The isolated compounds were tested fora-glucosidase inhibitory activity. All compounds showed more potent inhibitory activity with IC50 values 42–142 mM, than that of a positive control acarbose (IC50, 214.5 mM). Among all isolates, compounds 2, 4 and 6 exhibited significant a-glucosidase inhibitory activity with the IC50 values of 49.7, 42.6 and 55.9 mM, respectively. From the present investigation, all these compounds were isolated for the first time as well as their a-glucosidase inhibitoryactivity of T. ilicifolius. These results suggested that the traditional use of T. ilicifolius for the treatment of diabetes disease in Vietnam may be due to thea-glucosidase inhibitory activity of its phenolic constituents.

scholarly journals PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5505
Author(s):  
Hye Jin Kim ◽  
Xiao-Jun Li ◽  
Dong-Cheol Kim ◽  
Tai Kyoung Kim ◽  
Jae Hak Sohn ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Tyrosine Phosphatase ◽  
Competitive Inhibitor ◽  
Fungal Strain ◽  
Etoac Extract ◽  
Enzymatic Assays ◽  
Ic50 Values ◽  
Sugar Unit ◽  
Sesquiterpene Glycoside ◽  
The Absolute

Chemical investigation of the Antarctic lichen-derived fungal strain Acremonium sp. SF-7394 yielded a new amphilectane-type diterpene, acrepseudoterin (1), and a new acorane-type sesquiterpene glycoside, isocordycepoloside A (2). In addition, three known fungal metabolites, (−)-ternatin (3), [D-Leu]-ternatin (4), and pseurotin A (5), were isolated from the EtOAc extract of the fungal strain. Their structures were mainly elucidated by analyzing their NMR and MS data. The absolute configuration of 1 was proposed by electronic circular dichroism calculations, and the absolute configuration of the sugar unit in 2 was determined by a chemical method. The inhibitory effects of the isolated compounds on protein tyrosine phosphatase 1B (PTP1B) were evaluated by enzymatic assays; results indicated that acrepseudoterin (1) and [D-Leu]-ternatin (4) dose-dependently inhibited the enzyme activity with IC50 values of 22.8 ± 1.1 μM and 14.8 ± 0.3 μM, respectively. Moreover, compound 1 was identified as a competitive inhibitor of PTP1B.

scholarly journals Chemical constituents and theira-glucosidase inhibitory activity of the stem of Salacia chinensis L.

2021 ◽  
Vol 5 (3) ◽  
pp. first
Author(s):  
Huu Tho Le ◽  
Truc Thanh Thi Duong ◽  
Phu Hoang Dang ◽  
Truong Nhat Van Do ◽  
Hai Xuan Nguyen ◽  
...  
Keyword(s):  
Rheumatoid Arthritis ◽  
Back Pain ◽  
Inhibitory Activity ◽  
Spectroscopic Analysis ◽  
Methanol Extract ◽  
Chemical Constituents ◽  
Positive Control ◽  
Ic50 Values ◽  
Treatment Of Diabetes ◽  
Chcl3 Fraction

Salacia chinensis L., known as “Chop mao” in Vietnam, is a climbing shrub that belongs to the Celastraceae family. The stem of S. chinensis L. is used as a traditional medicine for the treatment of diabetes, rheumatoid arthritis, back pain, … The dried powdered stem of S. chinensis L. was collected in Phu Yen province and was extracted with methanol to yield methanol extract. The methanol extract was suspended in H2O and partitioned successively with n-hexane, CHCl3, EtOAc to obtain n-hexane, CHCl3, EtOAc, and H2O fractions, respectively. The CHCl3 fraction was subjected to a series of chromatographic separation to afford four purified compounds including 3-oxolup-20(29)-en-30-al (1), betulin-3-caffeate (2), 2-(4-hydroxy-3,5-dimethoxylphenyl)ethanol (3), and acetosyringone (4). Their structures were elucidated on the basis of the spectroscopic analysis and comparison with literature data. The isolated compounds were tested for their α-glucosidase inhibitory activity. The result indicated that all compounds (1-4) possessed significant α-glucosidase at the testing concentration of 100 µM with the percent inhibition values of 9.5 ± 1.3, 70.89 ± 0.25, 44.2 ± 1.6, and 6.7 ± 1.7 %, respectively. In addition, betulin-3-caffeate (2) and 2-(4-hydroxy-3,5-dimethoxylphenyl)ethanol (3) show more potent α-glucosidase inhibitory activity, with IC50 values of 69.7 and 152.0 µM, respectively, than that of positive control acarbose (IC50 = 214.5 µM).

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