scholarly journals A New Ellagic Acid From the Leaves and Twigs of Irvingia malayana

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984816
Author(s):  
Thaworn Jaipetch ◽  
Sakchai Hongthong ◽  
Samreang Bunteang ◽  
Radeekorn Akkarawongsapat ◽  
Jitra Limthongkul ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Ellagic Acid ◽  
Inhibitory Activity ◽  
Moderate Activity ◽  
Spectroscopic Techniques ◽  
Inhibition Assay ◽  
Phytochemical Investigation ◽  
Cancerous Cell ◽  
Reverse Transcriptase Assay ◽  
Hiv 1

A phytochemical investigation of the leaves and twigs of Irvingia malayana led to the isolation of a new 3,3′,4′-tri- O-methylellagic acid-6″-acetoxy-4- O-β-glucoside (1), along with 3,3′,4′-tri- O-methylellagic acid (2), 3,3′-di- O-methylellagic acid-4- O-β-xyloside (3), 3,3′,4′-tri- O-methylellagic acid-4-β -O-glucoside (4), friedelin (5), friedelinol (6), methyl-3,4,5-trihydroxybenzoate (7), 5,7,4′-trihydroxyflavone-8- C-β-glucopyranoside (8), 5,7,3′,4′-tetrahydroxyflavone-8- C-β-glucopyranoside (9), and 5,3′,4′-trihydroxyflavone-6- C-β-glucopyranoside (10). Their structures were elucidated by means of spectroscopic techniques and direct comparison with literature data. Compounds 4 and 7 showed weak cytotoxic activity against a panel of mammalian cancerous cell lines. Furthermore, compounds 1, 2, 4, and 9 exhibited significant inhibitory activity in the syncytium inhibition assay, whereas compounds 8 and 9 displayed moderate activity in the HIV 1 reverse transcriptase assay.

scholarly journals New Humulenes from Hyptis incana (Labiatae)

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801
Author(s):  
Mitsuru Satoh ◽  
Yoshio Satoh ◽  
Yasuhiro Anzai ◽  
Daisuke Ajisawa ◽  
Keiichi Matsuzaki ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Inhibitory Activity ◽  
Leukemia Cells ◽  
Moderate Activity ◽  
Mouse Leukemia ◽  
Aerial Parts ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Potent Growth

Two new humulene-type sesquiterpenes, named hyptishumulene I (1) and II (2), have been isolated, together with eight known compounds, a humulene-type sesquiterpene (3), a monoterpene (4) and six abietane-type diterpenoids (5–10) from the aerial parts of Hyptis incana (Labiatae). The cytotoxic activity of the isolated compounds against mouse leukemia cells (L1210) was examined. The abietane-type diterpenoids (5–10) showed rather potent growth inhibitory activity (IC50<15 μM), while the new humulene-type compounds (1 and 2) exhibited moderate activity (IC50>50 μM).

Synthesis and evaluation of novel heterocycles as potential HIV-1 enzyme inhibitors

2014 ◽  
Author(s):  
◽  
Gaëlle Tatiana Ngnie Tuemgnie
Keyword(s):  
Inhibitory Activity ◽  
Enzyme Inhibitors ◽  
Aldol Condensation ◽  
Click Reaction ◽  
Microwave Assisted Synthesis ◽  
Spectroscopic Techniques ◽  
Drug Molecules ◽  
Palladium Catalyzed ◽  
Dual Action ◽  
Hiv 1

This project has focussed on the synthesis and the evaluation of organic compounds as potential HIV-1 enzyme inhibitors, by making use of green chemistry (microwave assisted synthesis and click chemistry), palladium catalyzed reactions (Heck and Sonogashira coupling), Baylis Hillman methodology and aldol condensation. These compounds were synthesized in good yields and fully characterised by spectroscopic techniques. Biological assay data revealed that some of the compounds possess high inhibitory activity and their effective inhibitory concentration was as good as those of drugs in clinical use. These potential drug molecules were identified by preliminary investigations carried out by molecular modelling where a trend of their inhibitory activity against different enzymes was anticipated. Benzotriazole-AZT conjugates generated by 1,3-dipolar cycloaddition of anthranilic acid derivatives with AZT showed good inhibitory activity in silico against both HIV-1 protease (PR) and HIV-1 reverse transcriptase (RT) enzymes. Still in line with our dual action strategy, cinnamate ester-AZT conjugates were synthesized in three steps starting from benzaldehyde derivatives with a click reaction at the final step. These compounds also showed some inhibitory activity against HIV-1 RT enzyme (88%). In addition, the cinnamoyl fragment attached to AZT appeared to improve the activity of AZT against HIV-1 RT. Peptide chemistry involving carbonyl diimidazole as a coupling reagent between cinnamic acid derivatives and protected amino acids was used to prepare substituted amino acid derivatives which appeared to be very active against the integrase (IN) enzyme (88%). Commercially available coumarin was iodinated and derivatized through palladium catalyzed Heck and Sonogashira reactions with activated alkenes and a terminal alkyne respectively to afford novel coumarin derivatives in good yields. Optimization studies on the Heck reaction with regards to the phosphine ligand, the palladium catalyst and the solvent were carried out to afford novel formyl substituted cinnamate esters with nonaflyl salicylaldehyde derivatives.

scholarly journals A New Neolignan, and the Cytotoxic and Anti-HIV-1 Activities of Constituents from the Roots of Dasymaschalon sootepense

2016 ◽  
Vol 11 (6) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Sakchai Hongthong ◽  
Chutima Kuhakarn ◽  
Thaworn Jaipetch ◽  
Pawinee Piyachaturawat ◽  
Surawat Jariyawat ◽  
...  
Keyword(s):  
Reverse Transcriptase ◽  
Ethyl Acetate ◽  
Cytotoxic Activity ◽  
Ethyl Acetate Extract ◽  
Spectroscopic Techniques ◽  
Chemical Structures ◽  
Anti Hiv ◽  
Hiv 1

Bioassay-guided isolation from the ethyl acetate extract of Dasymaschalon sootepense roots led to the isolation of twelve compounds including a new dihydrobenzo-furan neolignan, (+)-(2S’,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-methylbenzofuran-5-carbaldehyde (5), and eleven known compounds (1-4, and 6-12). The chemical structures and stereochemistry of all the isolated compounds were established by spectroscopic techniques. The known compounds 4 and 6 have been fully characterized spectroscopically, including their absolute configurations. Cytotoxic and anti-HIV-1 reverse transcriptase (RT) activities of compounds 1-3, 5 and 8-12 were determined. Among compounds screened, compounds 2, 3 and 10 displayed weak cytotoxic activity with ED50 values ranging from 9.6-47.5 μM and only compound 2 was found weakly active against HIV-1 RT with an IC50 value of 323.2 μM.

Anti-HIV 1 Activity of Xanthones from the Bark of Mammea harmandii

2018 ◽  
Vol 13 (1) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Ponsiri Liangsakul ◽  
Chutima Kuhakarn ◽  
Sakchai Hongthong ◽  
Surawat Jariyawat ◽  
Kanoknetr Suksen ◽  
...  
Keyword(s):  
Reverse Transcriptase ◽  
Ethyl Acetate ◽  
Cytotoxic Activity ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Methanol Extract ◽  
Ethyl Acetate Fraction ◽  
Chemical Structures ◽  
Anti Hiv ◽  
Hiv 1

A new xanthone glycoside 1 together with four known flavonoid derivatives, astilbin (2), neoastilbin (3), isoastilbin (4), and epicatechin (5) were isolated from the ethyl acetate fraction partitioned from the methanol extract of the bark of Mammea harmandii. The chemical structures of all isolated compounds were established on the basis of their spectroscopic data. Compound 1 exhibited selective significant inhibitory activity in the anti-syncytium assay with an EC50 value of 11.44 μM (SI = 14.03) while it was found inactive against HIV 1 reverse transcriptase as well as cytotoxic activity.

Evaluation of Phytopolyphenols for their gp120-CD4 Binding Inhibitory Properties by In Silico Molecular Modelling & In Vitro Cell Line Studies

2019 ◽  
Vol 17 (2) ◽  
pp. 102-113 ◽  
Author(s):  
Amit Mirani ◽  
Harish Kundaikar ◽  
Shilpa Velhal ◽  
Vainav Patel ◽  
Atmaram Bandivdekar ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Gallic Acid ◽  
Cell Line ◽  
Ellagic Acid ◽  
Inhibitory Activity ◽  
In Silico ◽  
Early Stage ◽  
Binding Mode ◽  
Hiv 1

Background:Lack of effective early-stage HIV-1 inhibitor instigated the need for screening of novel gp120-CD4 binding inhibitor. Polyphenols, a secondary metabolite derived from natural sources are reported to have broad spectrum HIV-1 inhibitory activity. However, the gp120-CD4 binding inhibitory activity of polyphenols has not been analysed in silico yet.Objectives:To establish the usage of phytopolyphenols (Theaflavin, Epigallocatechin (EGCG), Ellagic acid and Gallic acid) as early stage HIV-1 inhibitor by investigating their binding mode in reported homology of gp120-CD4 receptor complex using in silico screening studies and in vitro cell line studies.Methods:The in silico molecular docking and molecular simulation studies were performed using Schrödinger 2013-2 suite installed on Fujitsu Celsius Workstation. The in vitro cell line studies were performed in the TZM-bl cell line using MTT assay and β-galactosidase assay.Results:The results of molecular docking indicated that Theaflavin and EGCG exhibited high XP dock score with binding pose exhibiting Van der Waals interaction and hydrophobic interaction at the deeper site in the Phe43 cavity with Asp368 and Trp427. Both Theaflavin and EGCG form a stable complex with the prepared HIV-1 receptor and their binding mode interaction is within the vicinity 4 Å. Further, in vitro cell line studies also confirmed that Theaflavin (SI = 252) and EGCG (SI = 138) exert better HIV-1 inhibitory activity as compared to Ellagic acid (SI = 30) and Gallic acid (SI = 34).Conclusions:The results elucidate a possible binding mode of phytopolyphenols, which pinpoints their plausible mechanism and directs their usage as early stage HIV-1 inhibitor.

Cytotoxic Rocaglamide Derivatives from Aglaia duppereana

2013 ◽  
Vol 68 (7-8) ◽  
pp. 269-274
Author(s):  
Mona El-Neketi ◽  
Weaam Ebrahim ◽  
Ngoc Tu Duong ◽  
Sahar Gedara ◽  
Farid Badria ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Phytochemical Investigation ◽  
Mouse Lymphoma

Phytochemical investigation of Aglaia duppereana flowers led to the isolation of a new rocaglamide derivative and twelve known congeners. The structure of the new compound was unambiguously elucidated by spectroscopic techniques (1D- and 2D-NMR, HRESIMS). The isolated compounds exhibited a potent cytotoxic activity against mouse lymphoma (L5178Y) cells with EC50 values ranging from 5.1 to 54.8 nM

Phytochemical Constituents of Annona reticulata and their Cytotoxic Activity

2020 ◽  
Vol 17 (3) ◽  
pp. 206-210
Author(s):  
Ty Viet Pham ◽  
Thang Quoc Le ◽  
Anh Tuan Le ◽  
Hung Quoc Vo ◽  
Duc Viet Ho
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Structural Determination ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
Phytochemical Constituents ◽  
First Time ◽  
Annona Reticulata

A phytochemical investigation of the leaves of Annona reticulata led to the isolation and structural determination of β-sitosterol (1), ent-pimara-8(14),15-dien-19-oic acid (2), ent-pimara- 8(14),15-dien-19-ol (3), quercetin (4), quercetin 3-O-α-L-arabinopyranoside (5), and a mixture of quercetin 3-O-β-D-galactopyranoside (6a) and quercetin 3-O-β-D-glucopyranoside (6b). Of these, compounds 2 and 3 were isolated from the genus Annona for the first time. Compound 3 showed strong cytotoxicity against SK-LU-1 and SW626 cell lines with IC50 values of 17.64 ± 1.07 and 19.79 ± 1.41 μg mL-1, respectively.

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.

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