scholarly journals Transformation of Psoralen and Isopsoralen by Human Intestinal Microbial In Vitro, and the Biological Activities of Its Metabolites

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4080 ◽  
Author(s):  
Lu Liu ◽  
Lei Zhang ◽  
Ze-Xu Cui ◽  
Xiao-Yan Liu ◽  
Wei Xu ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Biological Activities ◽  
Intestinal Flora ◽  
Acid Methyl Ester ◽  
Intestinal Bacteria ◽  
Ultra Performance Liquid Chromatography ◽  
Acid Methyl ◽  
Wide Range ◽  
Dried Fruit

Psoralen (P) and isopsoralen (IP) are the main active ingredients in the dried fruit of Psoralen corylifolia L. (PC), with a wide range of pharmacology activities. The intestinal bacteria biotransformation plays a central role in the metabolism of the complex ingredients in traditional Chinese medicine (TCM). Our study aimed to investigated the metabolic profile of P and IP in the intestinal condition, co-cultured with human fecal bacteria anaerobically. Four bio-transforming products were obtained, including 6,7-furano-hydrocoumaric acid (P-1) and 6,7-furano-hydro- coumaric acid methyl ester (P-2), which transformed from P, and 5,6-furano-hydrocoumaric acid (IP-1) and 5,6-furano-hydrocoumaric acid methyl ester (IP-2), which were transformed from IP. It is worth mentioning that IP-2 is a new compound that has not been published. Their structures were analyzed based on their spectroscopic data. Moreover, a highly sensitive ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was used to characterize the metabolic pathways of P, IP, and their bio-transforming products in the reaction samples. In addition, the dampening effects against the oxidative stress of P, IP, and their bio-transforming products by human intestinal flora were estimated in vitro via the human colorectal cells (HCT116) and heterogeneous human epithelial colorectal adenocarcinoma cells (Caco-2) cell lines. The results showed that the metabolites have stronger activity than P and IP, which possibly provides a basis for elucidating the treating mechanisms of PC extract against inflammatory bowel disease.

scholarly journals Synthesis and Antiproliferative Evaluation of Novel Hybrids of Dehydroabietic Acid Bearing 1,2,3-Triazole Moiety

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4191 ◽  
Author(s):  
Fang-Yao Li ◽  
Lin Huang ◽  
Qian Li ◽  
Xiu Wang ◽  
Xian-Li Ma ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Parent Compound ◽  
Acid Methyl Ester ◽  
Normal Liver ◽  
Dehydroabietic Acid ◽  
In Vitro Cytotoxicity ◽  
Human Carcinoma ◽  
Normal Liver Cell ◽  
Acid Methyl

To discover novel potent cytotoxic diterpenoids, a series of hybrids of dehydroabietic acid containing 1,2,3-triazole moiety were designed and synthesized. The target compounds were characterized by means of FT-IR, 1H NMR, 13C NMR, ESI-MS and elemental analysis techniques. The in vitro cytotoxicity of these compounds was evaluated by standard MTT (methyl thiazolytetrazolium) assay against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), BEL-7402 (liver) human carcinoma cell lines and human normal liver cell (HL-7702). The screening results revealed that most of the hybrids showed significantly improved cytotoxicity over parent compound DHAA. Among them, [1-(3-fluorobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3c), and [1-(2-nitrobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3k) displayed better antiproliferative activity with IC50 (50% inhibitory concentration) values of 5.90 ± 0.41 and 6.25 ± 0.37 µM toward HepG2 cells compared to cisplatin, while they exhibited lower cytotoxicity against HL-7702. Therefore, the 1,2,3-triazole-hybrids could be a promising strategy for the synthesis of antitumor diterpenoids and it also proved the essential role of 1,2,3-triazole moiety of DHAA in the biological activity.

scholarly journals A relatively wide-bandgap and air-stable donor polymer for fabrication of efficient semitransparent and tandem organic photovoltaics

2019 ◽  
Vol 116 (44) ◽  
pp. 22037-22043 ◽  
Author(s):  
Mohammad Mahdi Tavakoli ◽  
Riccardo Po ◽  
Gabriele Bianchi ◽  
Alessandra Cominetti ◽  
Chiara Carbonera ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Butyric Acid ◽  
Organic Photovoltaics ◽  
Acid Methyl Ester ◽  
Wide Bandgap ◽  
Open Circuit ◽  
Monolayer Graphene ◽  
Acid Methyl ◽  
Wide Range ◽  
Butyric Acid Methyl Ester

Organic photovoltaics (OPVs) have attracted tremendous attention in the field of thin-film solar cells due to their wide range of applications, especially for semitransparent devices. Here, we synthesize a dithiaindacenone-thiophene-benzothiadiazole-thiophene alternating donor copolymer named poly{[2,7-(5,5-didecyl-5H-1,8-dithia-as-indacenone)]-alt-[5,5-(5′,6′-dioctyloxy-4′,7′-di-2-thienyl-2′,1′,3′-benzothiadiazole)]} (PDTIDTBT), which shows a relatively wide bandgap of 1.82 eV, good mobility, and high transmittance and ambient stability. In this work, we fabricate an OPV device using monolayer graphene as top electrode. Due to the stability of PDTIDTBT in air and water, we use a wet transfer technique for graphene to fabricate semitransparent OPVs. We demonstrate OPVs based on the PDTIDTBT:Phenyl-C61/71-butyric acid methyl ester (PCBM) blend with maximum power conversion efficiencies (PCEs) of 6.1 and 4.75% using silver and graphene top electrodes, respectively. Our graphene-based device shows a high average visible transmittance (AVT) of 55%, indicating the potential of PDTIDTBT for window application and tandem devices. Therefore, we also demonstrate tandem devices using the PDTIDTBT:Phenyl-C61-butyric acid methyl ester (PC60BM) blend in both series and parallel connections with average PCEs of 7.3 and 7.95%, respectively. We also achieve a good average PCE of 8.26% with an average open circuit voltage (Voc) of 1.79 V for 2-terminal tandem OPVs using this blend. Based on tandem design, an OPV with PCE of 6.45% and AVT of 38% is demonstrated. Moreover, our devices show improved shelf life and ultraviolet (UV) stability (using CdSe/ZnS core shell quantum dots [QDs]) in ambient with 45% relative humidity.

Trypanocidal Activity of Oleoresin and Terpenoids Isolated from Pinus oocarpa

2005 ◽  
Vol 60 (9-10) ◽  
pp. 711-716 ◽  
Author(s):  
Julieta Rubio ◽  
José S. Calderón ◽  
Angélica Flores ◽  
Clementina Castro ◽  
Carlos L. Céspedes
Keyword(s):  
Methyl Ester ◽  
Trypanosoma Cruzi ◽  
Acute Infection ◽  
Acid Methyl Ester ◽  
Positive Control ◽  
Dehydroabietic Acid ◽  
Isopimaric Acid ◽  
Acid Methyl ◽  
Pinus Oocarpa

Abstract Fractionation with n-hexane/ethyl acetate (1:1 v/v) by open column chromatography of the oleoresin from Pinus oocarpa Schiede yielded two diterpenes, pimaric acid (1) and dehydroabietic acid (5), the sesquiterpene longifolene (3) and a diterpenic mixture containing pimaric acid (1), isopimaric acid (4) and dehydroabietic acid (5). Subsequently, the isolated compounds, the mixture of 1, 4 and 5, the oleoresin and the dehydroabietic acid methyl ester (2), were tested in vitro against epimastigotes of Trypanosoma cruzi, the causative agent of Chagas disease. The most active compounds were 1, 3 and the oleoresin, being as active as nifurtimox, a drug effective in the treatment of acute infection by American trypanosomiasis and used in this work as positive control.

scholarly journals PPARα/γ, adiponectin and GLUT4 overexpression induced by moronic acid methyl ester influenced on glucose and triglycerides levels of experimental diabetic mice

2021 ◽  
Author(s):  
Samuel Estrada-Soto ◽  
Litzia Cerón-Romero ◽  
Gabriel Navarrete-Vázquez ◽  
Edgar Rosales-Ortega ◽  
Jaime H. Gómez-Zamudio ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Acid Methyl Ester ◽  
Control Group ◽  
Oral Glucose ◽  
Acute Administration ◽  
Diabetic Mice ◽  
Ppar Γ ◽  
Acid Methyl

The current study aimed to determine the antidiabetic and antidyslipidemic activities of moronic acid methyl ester (1) by in vivo, in vitro, in silico and molecular biology studies. Compound 1 was evaluated to establish its dose-dependent antidiabetic and antihyperglycemic (50 mg/kg) activities, in diabetic and normoglycemic male CD1 mice, respectively. Also, compound 1 was subjected to a sub-acute study (50 mg/kg/day for eight days) to determine blood biochemical profiles and the expression of PTP-1B, GLUT4, PPAR-α, PPAR-γ, adiponectin, IL-1β, and MCP1 in adipose tissue of animals after treatment. Different doses in acute administration of 1 decreased glycemia (p < 0.05), compared with vehicle, showing greater effectiveness in the range 50-160 mg/kg. Also, the oral glucose tolerance test (OGTT) showed that 1 induced a significant antihyperglycemic action by opposing the hyperglycemic peak (p < 0.05). Moreover, 1 subacute administration decrease glucose and triglycerides levels after treatment (p < 0.05); while the expression of PPAR-α and γ, adiponectin and GLUT4 displayed an increase (p< 0.05) compared with the diabetic control group. In conclusion, compound 1 showed antihyperglycemic, antidiabetic and antidyslipidemic effects in normal and diabetic mice, probably due to insulin sensitization through increase mRNA expression of GLUT4, PPAR-α, PPAR-γ and adiponectin genes.

Chlorogenic acid methyl ester exerts strong anti-inflammatory effectsviainhibiting the COX-2/NLRP3/NF-κB pathway

2018 ◽  
Vol 9 (12) ◽  
pp. 6155-6164 ◽  
Author(s):  
Lang Zhang ◽  
Ya Fan ◽  
Hanwen Su ◽  
Li Wu ◽  
Yuying Huang ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Chlorogenic Acid ◽  
Acid Methyl Ester ◽  
Acid Methyl ◽  
Cox 2 ◽  
Anti Inflammatory

In vivoandin vitrostudies show that chlorogenic acid methyl ester (CME) has been proven to be a potential nutraceutical for preventing inflammation.

scholarly journals Assessment of the In Vitro Antischistosomal Activities of the Extracts and Compounds from Solidago Microglossa DC (Asteraceae) and Aristolochia Cymbifera Mart. & Zucc. (Aristolochiaceae)

2020 ◽  
Vol 2020 ◽  
pp. 1-11
Author(s):  
Poliana da Silva Costa ◽  
Ohana Oliveira Zuza da Silva ◽  
Danilo de Souza Costa ◽  
Lara Aparecida de Oliveira Silva ◽  
Priscila de Faria Pinto ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Motor Activity ◽  
Laser Scanning ◽  
Acid Methyl Ester ◽  
Vero Cells ◽  
Laser Scanning Microscopy ◽  
Confocal Laser ◽  
Acid Methyl ◽  
Antischistosomal Activity

Schistosomiasis, caused by helminth flatworms of the genus Schistosoma, is a neglected tropical disease that afflicts over 230 million people worldwide. Currently, treatment is achieved with only one drug, praziquantel (PZQ). In this regard, the roots of Solidago microglossa (Asteraceae) and Aristolochia cymbifera (Aristolochiaceae) are popularly used as anthelmintic. Despite their medicinal use against helminthiasis, such as schistosomiasis, A. cymbifera, and S. microglossa have not been evaluated against S. mansoni. Then, in this work, the in vitro antischistosomal activity of the crude extracts of A. cymbifera (Ac) and S. microglossa (Sm) and their isolated compounds were investigated against S. mansoni adult worms. Sm (200 μg/mL) and Ac (100–200 μg/mL) were lethal to all male and female worms at the 24 h incubation. In addition, Sm (10–50 μg/mL) and Ac (10 μg/mL) caused significant reduction in the parasite’s movements, showing no significant cytotoxicity to Vero cells at the same range of schistosomicidal concentrations. Confocal laser scanning microscopy revealed that Sm and Ac caused tegumental damages and reduced the numbers of tubercles of male schistosomes. Chromatographic fractionation of Sm leads to isolation of bauerenol, α-amirin, and spinasterol, while populifolic acid, cubebin, 2-oxopopulifolic acid methyl ester, and 2-oxopopulifolic acid were isolated from Ac. At concentrations of 25–100 μM, bauerenol, α-amirin, spinasterol, populifolic acid, and cubebin showed significant impact on motor activity of S. mansoni. 2-oxopopulifolic acid methyl ester and 2-oxopopulifolic acid caused 100% mortality and decreased the motor activity of adult schistosomes at 100 μM. This study has reported, for the first time, the in vitro antischistosomal effects of S. microglossa and A. cymbifera extracts, also showing promising compounds against adult schistosomes.

Phenolic Compounds and Flavonoids as Plant Growth Regulators from Fruit and Leaf of Vitex rotundifolia

2004 ◽  
Vol 59 (7-8) ◽  
pp. 509-514 ◽  
Author(s):  
Takeo Yoshioka ◽  
Tomohisa Inokuchi ◽  
Shozo Fujioka ◽  
Yasuo Kimura
Keyword(s):  
Phenolic Compounds ◽  
Methyl Ester ◽  
Plant Growth ◽  
Ferulic Acid ◽  
Growth Regulators ◽  
Vanillic Acid ◽  
Biological Activities ◽  
Acid Methyl Ester ◽  
Hydroxybenzoic Acid ◽  
Acid Methyl

AbstractFive phenolic compounds, 4-hydroxybenzoic acid methyl ester (1), vanillic acid methyl ester (2), 4-hydroxy benzaldehyde (3), 4-hydroxybenzoic acid (4) and ferulic acid (5), and four flavonoids, 5,5′-dihydroxy-4′,6,7-trimethoxyflavanone (6), luteolin (7), vitexicarpin (8) and artemetin (9), were isolated from fruits and leaves of Vitex rotundifolia L. The biological activities of these nine compounds have been examined using a bioassay with lettuce seedlings.

Natural chemical entities as bioactive moiety from weaver ant, Oecophylla smaragdina: An in vitro and in silico Study

2020 ◽  
Vol 17 ◽  
Author(s):  
Suchismeeta Behera ◽  
Priyanka Dash ◽  
Amulyaratna Behera ◽  
Chinmaya Chidananda Behera ◽  
Prafulla Kumar Mohanty
Keyword(s):  
Methyl Ester ◽  
Inhibitory Activity ◽  
In Silico ◽  
Acid Methyl Ester ◽  
Hexane Extract ◽  
Bioactive Molecules ◽  
Hexadecanoic Acid ◽  
Acid Methyl ◽  
In Silico Study

Background: Since time immemorial the ethnic community of Mayrubhanj District, Odisha, India has preferred to Olecophylla smaragdina as traditional medicine for their multiple ailments. Hence, the objective of the investigation is to scientifically examine the myth behind ethno-zoological claims using chemometric analysis as well as in vitro and in silico study. Methods: The maceration method was used for the extraction of O. smaragdina using hexane and methanol. In this study, various bioactive compounds of O. smaragdina were identified through GC MS analysis followed by an antimicrobial activity. The species was further studied for their binding modes for in silico inhibition of a choice of bacterial proteins using Biovia Discovery studio software. Results: Tetradecanoic acid, hexadecanoic acid, methyl ester, hexadecenoic acid, n-hexadecanoic acid, 9-octadecenoic acid, methyl ester, oleic acid, 9-octadecenamide are some important bioactive constituents identified through GCMS analysis. The hexane extract was found to be maximum inhibitory activity against Staphyllococus aureus. The % inhibitory activity of hexane and methanolic extract against S. aureus at a concentration of 400 μg/mL was found to be 90 and 83%, respectively. The high inhibitory capacity of the n-hexane extract was comparable to the standard drug Gentamycin which further supported the high receptor binding affinity of identified compound Octadecanoic acid towards Tyrosol-t RNA synthetase of staphylococcus aureus (PDB ID: 1JIK). Conclusion: Interestingly, this is probably the first report that the obtained bioactive molecules from O. smaragdina showed that binding site identification to carry out molecular docking studies and results showed that the better affinity to bind with suitable targeted moiety.

N-Acetylborrelidin B: a new bioactive metabolite from Streptomyces mutabilis sp. MII

2018 ◽  
Vol 73 (1-2) ◽  
pp. 49-57 ◽  
Author(s):  
Abdelaaty Hamed ◽  
Ahmed S. Abdel-Razek ◽  
Marcel Frese ◽  
Daniel Wibberg ◽  
Atef F. El-Haddad ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Methyl Ester ◽  
Bioactive Compounds ◽  
Screening Program ◽  
Acid Methyl Ester ◽  
In Vitro Cytotoxicity ◽  
Cervix Carcinoma ◽  
Nmr Studies ◽  
Acid Methyl

AbstractIn the course of our screening program for new bioactive compounds, a naturally new 18-membered macrolide antibiotic,N-acetylborrelidin B (1) along with borrelidin (2) were obtained from the marineStreptomyces mutabilissp. MII. The strain was isolated from a sediment sample collected in the Red Sea at the Hurghada Coast and characterized taxonomically. Additional nine diverse bioactive compounds were reported: 6-prenyl-indole-3-acetonitrile (3), sitosteryl-3β-d-glucoside, campesterol, ferulic acid, linoleic acid methyl ester, linoleic acid,N-acetylanthranilic acid, indole 3-acetic acid methyl ester, indole 3-carboxylic acid, and adenosine. Structure1was confirmed by in-depth NMR studies and by mass spectra, and comparison with related literature data. The antimicrobial activity of the strain extract and compounds1and2were studied using a panel of pathogenic microorganisms. The in vitro cytotoxicity of compounds1and2as well as the crude extract were tested against the human cervix carcinoma cell line (KB-3-1).

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