A new diphenylheptanoid from the rhizomes of Curcuma zedoaria

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Truong Nhat Van Do ◽  
Hai Xuan Nguyen ◽  
Tho Huu Le ◽  
Phu Hoang Dang ◽  
Mai Thanh Nguyen ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Positive Control ◽  
Curcuma Zedoaria ◽  
Phytochemical Investigation

Abstract A phytochemical investigation of the rhizomes of Curcuma zedoaria was carried out, leading to the isolation of a new diphenylheptanoid, zedoaroxane A (1), together with four known compounds (2–5). Their structures were elucidated based on NMR spectroscopic data. All isolated compounds possessed α-glucosidase inhibitory activity, with the IC50 values ranging from 35.2 to 89.0 µM, more potent than that of the positive control acarbose (IC50, 214.5 µM).

scholarly journals Three Novel Biphenanthrene Derivatives and a New Phenylpropanoid Ester from Aerides multiflora and Their α-Glucosidase Inhibitory Activity

Plants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 385
Author(s):  
May Thazin Thant ◽  
Boonchoo Sritularak ◽  
Nutputsorn Chatsumpun ◽  
Wanwimon Mekboonsonglarp ◽  
Yanyong Punpreuk ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Competitive Inhibition ◽  
Positive Control ◽  
The Other ◽  
Biological Investigation ◽  
Phytochemical Investigation ◽  
Whole Plants ◽  
New Compounds ◽  
Burk Plot

A phytochemical investigation on the whole plants of Aerides multiflora revealed the presence of three new biphenanthrene derivatives named aerimultins A–C (1–3) and a new natural phenylpropanoid ester dihydrosinapyl dihydroferulate (4), together with six known compounds (5–10). The structures of the new compounds were elucidated by analysis of their spectroscopic data. All of the isolates were evaluated for their α-glucosidase inhibitory activity. Aerimultin C (3) showed the most potent activity. The other compounds, except for compound 4, also exhibited stronger activity than the positive control acarbose. Compound 3 showed non-competitive inhibition of the enzyme as determined from a Lineweaver–Burk plot. This study is the first phytochemical and biological investigation of A. multiflora.

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.

Bioactivity-guided isolation of aurone derivatives with hepatoprotective activities from the fruits of Cucumis bisexualis

2020 ◽  
Vol 75 (9-10) ◽  
pp. 327-332 ◽  
Author(s):  
Qin-Ge Ma ◽  
Rong-Rui Wei ◽  
Zhi-Pei Sang
Keyword(s):  
Spectroscopic Data ◽  
Positive Control ◽  
Phytochemical Investigation ◽  
First Time

AbstractBioactivity-guided phytochemical investigation of Cucumis bisexualis has led to the isolation of three new coumarin-aurone heterodimers (1-3), along with six aurone derivatives (4-9) were isolated from C. bisexualis for the first time. Their structures were determined by their extensive spectroscopic data and comparison with the values reported in the references. All isolated compounds (1-9) were evaluated for their hepatoprotective activities on human L-O2 cells, which compared with positive control of Bifendatatum. Among them, compounds 1, 2, and 7 exhibited moderate hepatoprotective activities to promote effects on the proliferation of L-O2 cells.

scholarly journals Secondary Metabolites with α-Glucosidase Inhibitory Activity from Mangrove Endophytic Fungus Talaromyces sp. CY-3

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 492
Author(s):  
Wencong Yang ◽  
Qi Tan ◽  
Yihao Yin ◽  
Yan Chen ◽  
Yi Zhang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
13C Nmr ◽  
Inhibitory Activity ◽  
Endophytic Fungus ◽  
Spectroscopic Data ◽  
Positive Control ◽  
Mangrove Endophytic Fungus ◽  
Chemical Hydrolysis ◽  
Ic50 Value ◽  
New Compounds

Eight new compounds, including two sambutoxin derivatives (1–2), two highly oxygenated cyclopentenones (7–8), four highly oxygenated cyclohexenones (9–12), together with four known sambutoxin derivatives (3–6), were isolated from semimangrove endophytic fungus Talaromyces sp. CY-3, under the guidance of molecular networking. The structures of new isolates were elucidated by analysis of detailed spectroscopic data, ECD spectra, chemical hydrolysis, 13C NMR calculation, and DP4+ analysis. In bioassays, compounds 1–5 displayed better α-glucosidase inhibitory activity than the positive control 1-deoxynojirimycin (IC50 = 80.8 ± 0.3 μM), and the IC50 value was in the range of 12.6 ± 0.9 to 57.3 ± 1.3 μM.

scholarly journals Lignans and Terpenoids From the Fruits of Vitex kwangsiensia and Their Inhibitory Activity on Nitric Oxide Production in Macrophages

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984817
Author(s):  
Tong Shen ◽  
Yongdong Wang ◽  
Zhiming Zhu ◽  
Xiujie Wang ◽  
Tian Tian
Keyword(s):  
Nitric Oxide ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Spectroscopic Methods ◽  
Nitric Oxide Production ◽  
Oxide Production ◽  
Raw264.7 Macrophages ◽  
Phytochemical Investigation ◽  
Reported Data ◽  
First Time

Phytochemical investigation of the fruits from Vitex kwangsiensia led to the isolation of 18 constituents, including 6 lignans (1-6), 3 diterpenoids (7-9), 2 sesquiterpenoids (10, 11), 2 triterpenoids (16, 17), and 5 other compounds. Their structures were identified by spectroscopic methods (mass spectroscopy, infrared, UV, 1-dimensional and 2-dimensional nuclear magnetic resonance) and comparison with reported data in the literatures. Among these constituents, compound 1 was a new lignan and named as vitekwangin A. The spectroscopic data of 2 was reported herein for the first time, and given a trivial name vitekwangin B. The isolated lignans, diterpenoids, and sesquiterpenoids were evaluated for their inhibitory activity to prevent nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophages.

scholarly journals New polyoxygenated polyketide from pathogenic fungus Cylindrocarpon destructans with α-glycosidase inhibitory activity

2018 ◽  
Vol 7 (4) ◽  
pp. 303-307
Author(s):  
Dilfaraz Khan ◽  
Shahid Ullah Khan ◽  
Shah Iram Niaz ◽  
Muhammad Haroon ◽  
Syed Badshah ◽  
...  
Keyword(s):  
Data Analysis ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Pathogenic Fungus ◽  
2D Nmr ◽  
Inhibition Activity ◽  
Cylindrocarpon Destructans ◽  
Phytochemical Investigation ◽  
Glycosidase Inhibition

Phytochemical investigation on pathogenic fungus Cylindrocarpon destructans isolated form Meconopsisgrandis plant led to the isolation of one new polyoxygenated polyketides, namely cylindrocarpolide A along with five known compounds. The structures of the isolated compounds were elucidated by 1D and 2D NMR and mass spectroscopic data analysis. The isolated compounds were evaluated for α-glycosidase inhibition activity. The compounds isolated compounds were found to have strong to weak inhibition against the α-glycosidase enzymes

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).

Inhibitory effects of bioaccessible anthocyanins and procyanidins from apple, red grape, cinnamon on α-amylase, α-glucosidase and lipase

2020 ◽  
pp. 1-9
Author(s):  
Pınar Ercan ◽  
Sedef Nehir El
Keyword(s):  
Inhibitory Activity ◽  
Digestive Enzymes ◽  
Positive Control ◽  
Anthocyanin Content ◽  
Inhibitory Effects ◽  
Total Anthocyanin ◽  
Total Anthocyanin Content ◽  
Before And After ◽  
Red Grape

Abstract. The goals of this study were to determine and evaluate the bioaccessibility of total anthocyanin and procyanidin in apple (Amasya, Malus communis), red grape (Papazkarası, Vitis vinifera) and cinnamon (Cassia, Cinnamomum) using an in vitro static digestion system based on human gastrointestinal physiologically relevant conditions. Also, in vitro inhibitory effects of these foods on lipid (lipase) and carbohydrate digestive enzymes (α-amylase and α-glucosidase) were performed with before and after digested samples using acarbose and methylumbelliferyl oleate (4MUO) as the positive control. While the highest total anthocyanin content was found in red grape (164 ± 2.51 mg/100 g), the highest procyanidin content was found in cinnamon (6432 ± 177.31 mg/100 g) (p < 0.05). The anthocyanin bioaccessibilities were found as 10.2 ± 1%, 8.23 ± 0.64%, and 8.73 ± 0.70% in apple, red grape, and cinnamon, respectively. The procyanidin bioaccessibilities of apple, red grape, and cinnamon were found as 17.57 ± 0.71%, 14.08 ± 0.74% and 18.75 ± 1.49%, respectively. The analyzed apple, red grape and cinnamon showed the inhibitory activity against α-glucosidase (IC50 544 ± 21.94, 445 ± 15.67, 1592 ± 17.58 μg/mL, respectively), α-amylase (IC50 38.4 ± 7.26, 56.1 ± 3.60, 3.54 ± 0.86 μg/mL, respectively), and lipase (IC50 52.7 ± 2.05, 581 ± 54.14, 49.6 ± 2.72 μg/mL), respectively. According to our results apple, red grape and cinnamon have potential to inhibit of lipase, α-amylase and α-glucosidase digestive enzymes.

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 Potential Anticancer Lipoxygenase Inhibitors from the Red Sea-Derived Brown Algae Sargassum cinereum: An In-Silico-Supported In-Vitro Study

Antibiotics ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 416
Author(s):  
Sami I. Alzarea ◽  
Abeer H. Elmaidomy ◽  
Hani Saber ◽  
Arafa Musa ◽  
Mohammad M. Al-Sanea ◽  
...  
Keyword(s):  
Red Sea ◽  
Antiproliferative Activity ◽  
Inhibitory Activity ◽  
Brown Algae ◽  
In Silico ◽  
Active Sites ◽  
In Vitro Study ◽  
Lipoxygenase Inhibitors ◽  
Phytochemical Investigation

LC-MS-assisted metabolomic profiling of the Red Sea-derived brown algae Sargassum cinereum “Sargassaceae” dereplicated eleven compounds 1–11. Further phytochemical investigation afforded two new aryl cresol 12–13, along with eight known compounds 14–21. Both new metabolites, along with 19, showed moderate in vitro antiproliferative activity against HepG2, MCF-7, and Caco-2. Pharmacophore-based virtual screening suggested both 5-LOX and 15-LOX as the most probable target linked to their observed antiproliferative activity. The in vitro enzyme assays revealed 12 and 13 were able to inhibit 5-LOX more preferentially than 15-LOX, while 19 showed a convergent inhibitory activity toward both enzymes. Further in-depth in silico investigation revealed the molecular interactions inside both enzymes’ active sites and explained the varying inhibitory activity for 12 and 13 toward 5-LOX and 15-LOX.

Sign in / Sign up

Export Citation Format

Share Document