This document summarizes research on isolating and identifying anti-HIV compounds from Calophyllum brasiliense leaves. Three dipyranocoumarins with anti-HIV activity were isolated through bioassay-guided fractionation: calanolides A and B, and soulattrolide. Other compounds isolated like apetalic acid and amentoflavone showed no HIV-1 reverse transcriptase inhibitory activity. The isolated compounds were characterized through spectroscopy and their anti-HIV properties were evaluated in inhibition assays of HIV-1 reverse transcriptase, cytotoxicity on immune cells, and inhibition of HIV replication.
This document describes a facile synthetic route for producing the alpha-glucosidase inhibitor 2,6-dideoxy-2,6-imino-7-O-beta-D-glucopyranosyl-D-glycero-L-gulo-heptitol (1) in 26% overall yield from nojirimycin bisulfite adduct (2). Key steps include: (1) appending a nitrile group to (2) to form an intermediate (3), (2) hydrolyzing (3) to the carboxylic acid (6), and (3) condensing (6) with a protected glucose donor to form the glucoside (9), which
This study evaluated the antioxidant activity and phenolic content of red propolis samples from the state of Sergipe, Brazil. All propolis samples showed antioxidant activity in DPPH radical scavenging tests, which was confirmed by more sensitive lipid peroxidation and chemiluminescence assays. Lipid peroxidation inhibition ranged from 48.08% to 93.37%, higher than previous studies. Extracts with the highest antioxidant activity also had the highest total phenolic content, though not the highest flavonoid levels. The presence of flavonoids catechin, epicatechin and formononetin was confirmed in all samples by UFLC.
Isolation and Characterization of Colchicine from Physostigma VenenosiumIOSR Journals
This document describes the isolation and characterization of colchicine from the Nigerian medicinal plant Physostigma venenosium. Researchers extracted the seeds of P. venenosium with ethanol to obtain a crude extract. This extract was partitioned to yield chloroform, water, methanol, and petroleum ether fractions. Thin layer chromatography revealed that the chloroform fraction contained the highest number of compounds. Column chromatography of this fraction led to the isolation of a pure yellow compound identified as colchicine based on infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance data including 1H NMR, 13C NMR, COSY, and DEPT experiments. The isolation of colchicine from P. ven
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...inventionjournals
A series of 3-[(3-phenyl-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imino]-1,3-dihydro-2Hindole-2-one derivatives were synthesised through the nucleophilic substitution at carbonyl carbon of Isatin. Structure of synthesized compounds were elucidated by using IR, 1H NMR & 13C NMR spectrometry. Synthesised compounds showed significant antibacterial activity against E.coli (ATCC 35218), S.aureus (ATCC 25323), E.faecalis (Clinical isolate), K. Pneumonia, P. aeruginosa (ATCC 27893) using agar well diffusion method.
This document describes research on the synthesis of anti-1,2-diols using aldehyde α-oxygenation followed by organometallic addition. Contrary to previous reports, the researchers found this method produces anti-diols, not syn-diols. They demonstrated the scope of the reaction using different organometallic reagents and applied it to synthesize stereoisomers of oxylipins from a plant, determining the stereochemistry of two natural products. The synthesis involved aldehyde α-oxygenation, organometallic addition, functional group manipulations and comparisons to natural products to assign stereochemistry.
This document describes an efficient synthetic route to produce ethyl 2-aryl-4-hydroxy-1,3(2H,4H)-dioxoisoquinoline-4-carboxylates, which are known to inhibit auxin transport in plants and have plant growth regulating properties. The synthesis involves condensing anilines with homophthalic anhydride to form intermediates, which are then modified through various steps including acylation, enolate formation, alcoholysis, and oxygenation to produce the target compounds. Several of the target compounds showed potent auxin transport inhibition and plant growth regulating activity in tests.
The document describes the synthesis and antimicrobial screening of some pyrazolyl heterocycles. Specifically, it details the synthesis of compounds 3, 4, 5, and 6 through various reactions between 1-phenyl-3-(2-pyridyl)-1H-pyrazole-4-carboxaldehyde and acetophenone derivatives. Compound 3 undergo oxidative cyclization to form compounds 4 and 5. Compound 3 also undergoes condensation with hydrazine to form compound 6. The structures of compounds 3, 4, 5, and 6 were characterized using spectral methods. These compounds were then tested for antimicrobial activity against various bacteria and fungi, with some compounds showing moderate to good activity.
This document describes an efficient method for isolating and purifying the terpenoid components ginkgolides A, B, C, J and bilobalide from Ginkgo biloba extracts in a single protocol. The method takes advantage of the selective benzylation of ginkgolides B and C compared to A and J. A single chromatography step separates bilobalide from the ginkgolides. Benzylation and a second chromatography then allows isolation of individual ginkgolides. Hydrogenolysis removes the benzyl groups, providing pure ginkgolides B and C. This rapid protocol provides gram quantities of the isolated terpenoids.
This document describes a facile synthetic route for producing the alpha-glucosidase inhibitor 2,6-dideoxy-2,6-imino-7-O-beta-D-glucopyranosyl-D-glycero-L-gulo-heptitol (1) in 26% overall yield from nojirimycin bisulfite adduct (2). Key steps include: (1) appending a nitrile group to (2) to form an intermediate (3), (2) hydrolyzing (3) to the carboxylic acid (6), and (3) condensing (6) with a protected glucose donor to form the glucoside (9), which
This study evaluated the antioxidant activity and phenolic content of red propolis samples from the state of Sergipe, Brazil. All propolis samples showed antioxidant activity in DPPH radical scavenging tests, which was confirmed by more sensitive lipid peroxidation and chemiluminescence assays. Lipid peroxidation inhibition ranged from 48.08% to 93.37%, higher than previous studies. Extracts with the highest antioxidant activity also had the highest total phenolic content, though not the highest flavonoid levels. The presence of flavonoids catechin, epicatechin and formononetin was confirmed in all samples by UFLC.
Isolation and Characterization of Colchicine from Physostigma VenenosiumIOSR Journals
This document describes the isolation and characterization of colchicine from the Nigerian medicinal plant Physostigma venenosium. Researchers extracted the seeds of P. venenosium with ethanol to obtain a crude extract. This extract was partitioned to yield chloroform, water, methanol, and petroleum ether fractions. Thin layer chromatography revealed that the chloroform fraction contained the highest number of compounds. Column chromatography of this fraction led to the isolation of a pure yellow compound identified as colchicine based on infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance data including 1H NMR, 13C NMR, COSY, and DEPT experiments. The isolation of colchicine from P. ven
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...inventionjournals
A series of 3-[(3-phenyl-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imino]-1,3-dihydro-2Hindole-2-one derivatives were synthesised through the nucleophilic substitution at carbonyl carbon of Isatin. Structure of synthesized compounds were elucidated by using IR, 1H NMR & 13C NMR spectrometry. Synthesised compounds showed significant antibacterial activity against E.coli (ATCC 35218), S.aureus (ATCC 25323), E.faecalis (Clinical isolate), K. Pneumonia, P. aeruginosa (ATCC 27893) using agar well diffusion method.
This document describes research on the synthesis of anti-1,2-diols using aldehyde α-oxygenation followed by organometallic addition. Contrary to previous reports, the researchers found this method produces anti-diols, not syn-diols. They demonstrated the scope of the reaction using different organometallic reagents and applied it to synthesize stereoisomers of oxylipins from a plant, determining the stereochemistry of two natural products. The synthesis involved aldehyde α-oxygenation, organometallic addition, functional group manipulations and comparisons to natural products to assign stereochemistry.
This document describes an efficient synthetic route to produce ethyl 2-aryl-4-hydroxy-1,3(2H,4H)-dioxoisoquinoline-4-carboxylates, which are known to inhibit auxin transport in plants and have plant growth regulating properties. The synthesis involves condensing anilines with homophthalic anhydride to form intermediates, which are then modified through various steps including acylation, enolate formation, alcoholysis, and oxygenation to produce the target compounds. Several of the target compounds showed potent auxin transport inhibition and plant growth regulating activity in tests.
The document describes the synthesis and antimicrobial screening of some pyrazolyl heterocycles. Specifically, it details the synthesis of compounds 3, 4, 5, and 6 through various reactions between 1-phenyl-3-(2-pyridyl)-1H-pyrazole-4-carboxaldehyde and acetophenone derivatives. Compound 3 undergo oxidative cyclization to form compounds 4 and 5. Compound 3 also undergoes condensation with hydrazine to form compound 6. The structures of compounds 3, 4, 5, and 6 were characterized using spectral methods. These compounds were then tested for antimicrobial activity against various bacteria and fungi, with some compounds showing moderate to good activity.
This document describes an efficient method for isolating and purifying the terpenoid components ginkgolides A, B, C, J and bilobalide from Ginkgo biloba extracts in a single protocol. The method takes advantage of the selective benzylation of ginkgolides B and C compared to A and J. A single chromatography step separates bilobalide from the ginkgolides. Benzylation and a second chromatography then allows isolation of individual ginkgolides. Hydrogenolysis removes the benzyl groups, providing pure ginkgolides B and C. This rapid protocol provides gram quantities of the isolated terpenoids.
This document describes a new capillary zone electrophoresis (CZE) method for the simultaneous quantitative determination of β-N-oxalyl-L-α,β-diaminopropionic acid (β-ODAP) and homoarginine in Lathyrus sativus (grass pea). The method uses a new sodium borate-sodium sulfate run buffer at pH 9.2. It was found that the ratio of α- and β-ODAP isomers changes from 34.5/65.5 to 28.6/71.4 as the pH increases from 3.0 to 11.0. The method allows for the fast, simple, and sensitive determination of β-OD
This document summarizes a study that characterized carotenoids and their esters in red pepper pods through LC-DAD-APCI-MSn experiments. 42 compounds were detected, including 4 non-esterified carotenoids, 11 monoesters, and 17 diesters. Capsanthin esterified with lauric, palmitic, and myristic acids were predominant. Additionally, 3 β-cryptoxanthin monoesters and 1 zeaxanthin monoester were tentatively identified for the first time in red pepper pods. Selective collision-induced dissociation experiments were used to distinguish between regioisomers of capsanthin esters. The results demonstrate that the caroten
This document summarizes the discovery of a new class of insecticides called anthranilic diamides. The compounds were found to activate ryanodine receptors in insects, causing uncontrolled release of calcium stores and ultimately death. The document describes the synthesis of various analogs of anthranilic diamides containing modifications like halogen substitutions, ring sizes, and heterocyclic moieties. Key intermediates and reaction schemes are provided to illustrate the various routes taken to synthesize the analogs. Testing showed certain analogs had exceptional insecticidal activity, with one example called DP-23 being particularly potent.
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
Sensitive and selective detection of chemical residues in hops is necessary to ensure protection of consumers and the environment. Methods using LC-MS provide efficient and effective detection of chemical residues in a complex sample matrix such as hops. Presented here is an LC-MS method for detection of over 150 analytes in hops and a market survey of over 50 different hops pellets samples.
This document summarizes the synthesis and spectral analysis of a novel benzyl derivative of ciprofloxacin (Cip-D) and its copper(II) and cobalt(II) complexes. Cip-D was synthesized by reacting ciprofloxacin with benzyl chloride in the presence of triethylamine to introduce an amide group. Spectral analysis using 1H NMR, IR, and mass spectroscopy confirmed the structure of Cip-D and indicated bonding between the metal ions and Cip-D in the complexes. Analysis showed shifts in peaks for the complexes, indicating coordination between the metal ions and Cip-D. The Cip-D and its Cu(II) and Co(II)
A STUDY ON FORMATION OF SALYCILIC ACID FORMALDEHYDE POLYMER SAMPLEEDITOR IJCRCPS
Condensation of salicylic acid (0.02 mole) with formaldehyde (0.016 mole) in presence of aqueous 40% H2SO4.
Keywords: pipette,thermometer,spectro-photometer,conicalflakk,waterbath.
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
All manuscripts are subject to rapid peer review. Those of high quality (not previously published and not under consideration for publication in another journal) will be published without delay.
This document summarizes the revised NMR data for the alkaloid incartine isolated from Galanthus elwesii. The researchers revised the previously reported NMR data for incartine through 2D NMR experiments. They also isolated four other alkaloids from G. elwesii: hordenine, lycorine, 8-O-demethylhomolycorine, and hippeastrine. In vitro bioactivity studies showed that incartine had no remarkable antiviral or cytotoxic activity and only weakly inhibited acetylcholinesterase.
Glomerella cingulata, a plant pathogen fungus, was able to biotransform (+)-camphorquinone and (-)-camphorquinone into diols with high stereoselectivity and enantioselectivity over 10 days. (+)-Camphorquinone was transformed into (+)-2-exo-3-exo-camphane-2,3-diol with high stereoselectivity. (-)-Camphorquinone was transformed into (+)-2-endo-3-exo-camphane-2,3-diol with high stereo- and enantioselectivity. This is the first report of these specific biotransformations by microorganisms.
Antibody Glycan Analysis with Normal Phase PhyTip ColumnsChris Suh
1) Glycans are complex carbohydrates that are attached to proteins and lipids and play important roles in cellular functions and disease.
2) This study presents methods to fluorescently label and purify glycans from glycoproteins using PhyTip columns containing Sephadex G10 or normal phase resin, enabling their analysis by capillary electrophoresis.
3) Glycoproteins were digested with enzymes to release glycans, which were then labeled with a fluorescent tag and purified using the PhyTip columns to remove excess label prior to profiling and quantification by capillary electrophoresis.
This document summarizes research into separating the enantiomers of lactic acid dimer (lactide) for sustainable bioplastic production. Two promising methods were discovered: 1) Synthesizing and separating diastereomers of lactide with (S)-2-methyl-1-butanol as a chiral auxiliary. 2) Using kinetic discrimination during esterification of lactide with (R)-(-)-myrtenol, which reacted faster with the S enantiomer. (S)-2-methyl-1-butanol formed diastereomers with similar kinetics, but separation was possible by crystallization. (R)-myrtenol showed strong kinetic preference for the S enantiomer. This
This document describes an inter-laboratory evaluation study conducted to validate the use of the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay as a standard method for evaluating the antioxidant capacity of food additives. Fourteen laboratories participated in the study. Five analytical samples - four existing food additives (tea extract, grape seed extract, enju extract, and d-α-tocopherol) and Trolox - were evaluated using the DPPH assay. The results showed good repeatability for measuring antioxidant capacity within laboratories, but greater variability between laboratories. However, expressing the results as Trolox equivalent antioxidant capacity reduced inter-laboratory variability, suggesting the DPPH assay could be
Structural elucidation, Identification, quantization of process related impur...IOSR Journals
Major process related unknown impurity associated with the synthesis of Hydralazine hydrochloride bulk drug was detected by high performance liquid chromatography (HPLC) and was subjected to high resolution accurate liquid chromatography mass spectroscopy (HR/AM-LCMS) for identification. The proposed impurity was isolated from Hydralazine hydrochloride active pharmaceutical ingredient (API) by preparative chromatographic method and was injected on HPLC for comparison of retention time with that of the unknown process related impurity in Hydralazine hydrochloride. The molecular ion peak of preparatively isolated impurity and that of unknown process related impurity in Hydralazine hydrochloride were compared for confirmation. The postulated structure was unambiguously confirmed with the help of HR/AM- LC MS/MS, NMR and FTIR data proposed to be 1-(2-phthalazin-1-ylhydrazino)phthalazine (Hazh Dimer). This impurity of Hydralazine hydrochloride is not been previously reported. A rapid Acquity H-class gradient method with runtime of 15.0min was developed for Quantitation on Unisphere Cyno column and validated for parameters such as accuracy, precision, linearity and range, robustness. The LOD and LOQ of method were 0081% and 0.0246% respectively.
Evaluation of antioxidant and antiradical properties of pomegranate (punica g...Pritam Kolge
Evaluation of antioxidant and antiradical properties
of Pomegranate (Punica granatum L.) seed and defatted
seed extracts
This is Journal Club activity Presentation with the reference of various research papers.
This Presentation Contain following...
#Info about Paper
#Abstract
#Materials
#Methods
#Results
#Discussion
#Conclusion
#References
*Important Methods used
#Moisture content
#Fat content
#Acid value
#Peroxide value
#Oxidative stability index
#Total phenols content
#Preparation of Pomegranate seed extracts and calculate extract yield
#Evaluation of antioxidant properties of Pomegranate seed extracts using
-DPPH radicals scavenging activity
-FRAP assay
#Antioxidant efficiency of seed extract (Oxidative stability extract)
#Statistical analysis
Journal Club Presentation at Bharati Vidyapeeth College of Pharmacy, Kolhapur.
Thanks for Help and Guidance of Dr. P. B. Choudhari (Assistant Professor, Pharmaceutical Chemistry) and Dr. A. J. Shinde (Assistant Professor, Department of Pharmaceutics)
This document describes the synthesis and properties of mixed backbone oligodeoxynucleotides containing both negatively charged phosphodiester linkages and positively charged guanidinium linkages. Specifically, it reports the solid phase synthesis of chimeric guanidinium/phosphodiester oligonucleotides and studies their thermal stability when hybridized to complementary DNA or RNA strands. It also examines the resistance of these chimeras to degradation by exonuclease I enzyme.
Quantitative and Qualitative analysis of Toxicology pharm 402Justas Lauzadis
The document discusses quantitative and qualitative analysis of toxicology compounds. In the qualitative analysis, four compounds were extracted from rabbit serum at different pH levels using liquid-liquid extraction and GC/MS. Two compounds were extracted at basic pH and one at acidic pH, while one compound was not extracted. In the quantitative analysis, reverse phase HPLC was used to analyze malathion concentrations in water samples. Calibration curves were made using standards and an internal standard. The sample analysis found a higher concentration than expected due to loss of product, which was corrected using the internal standard data. Improper pipetting was identified as the source of error.
Four anthraquinone compounds were isolated from the rare southern Illinois lichen Lasallia papulosa. Two compounds, 7-chloroemodin and valsarin, had been previously isolated from this lichen species. The other two compounds, 5-chloro-1-O-methylemodin and 5-chloro-1-O-methyl-β-hydroxyemodin, had only been previously isolated from laboratory-cultured Nephroma laevigatum and were the first isolation from lichens in their natural habitat. The compounds were characterized using various analytical techniques and identified.
The study evaluated the anti-inflammatory activity of the hexane extract and two sesquiterpenes, cacalol and cacalone, isolated from Psacalium decompositum in carrageenan-induced rat paw edema and TPA-induced ear edema models. Both the hexane extract and sesquiterpenes showed dose-dependent inhibition of carrageenan-induced edema. In the TPA-induced model, all tested compounds showed anti-inflammatory activity in a dose-dependent manner. Cacalone showed the most prominent anti-inflammatory activity in both models. The study suggests that some beneficial effects attributed to P. decompositum in traditional medicine can be related to the anti-inflammatory activity
This document summarizes a study on the synthesis and NMR analysis of various Naproxen and Ibuprofen ester derivatives. Several diastereoisomeric Naproxyl-Naproxenate, Naproxyl-Ibuprofenate, and Ibuprofyl-Naproxenate esters were synthesized. Variable temperature NMR experiments showed differences in aromatic ring dynamics between esters, likely due to varying axial rotation speeds. Chiral shift reagent NMR experiments were also performed and provided insights into epimerization levels, assignments of proton signals, and geometries of the ester complexes.
This document describes a new capillary zone electrophoresis (CZE) method for the simultaneous quantitative determination of β-N-oxalyl-L-α,β-diaminopropionic acid (β-ODAP) and homoarginine in Lathyrus sativus (grass pea). The method uses a new sodium borate-sodium sulfate run buffer at pH 9.2. It was found that the ratio of α- and β-ODAP isomers changes from 34.5/65.5 to 28.6/71.4 as the pH increases from 3.0 to 11.0. The method allows for the fast, simple, and sensitive determination of β-OD
This document summarizes a study that characterized carotenoids and their esters in red pepper pods through LC-DAD-APCI-MSn experiments. 42 compounds were detected, including 4 non-esterified carotenoids, 11 monoesters, and 17 diesters. Capsanthin esterified with lauric, palmitic, and myristic acids were predominant. Additionally, 3 β-cryptoxanthin monoesters and 1 zeaxanthin monoester were tentatively identified for the first time in red pepper pods. Selective collision-induced dissociation experiments were used to distinguish between regioisomers of capsanthin esters. The results demonstrate that the caroten
This document summarizes the discovery of a new class of insecticides called anthranilic diamides. The compounds were found to activate ryanodine receptors in insects, causing uncontrolled release of calcium stores and ultimately death. The document describes the synthesis of various analogs of anthranilic diamides containing modifications like halogen substitutions, ring sizes, and heterocyclic moieties. Key intermediates and reaction schemes are provided to illustrate the various routes taken to synthesize the analogs. Testing showed certain analogs had exceptional insecticidal activity, with one example called DP-23 being particularly potent.
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
Sensitive and selective detection of chemical residues in hops is necessary to ensure protection of consumers and the environment. Methods using LC-MS provide efficient and effective detection of chemical residues in a complex sample matrix such as hops. Presented here is an LC-MS method for detection of over 150 analytes in hops and a market survey of over 50 different hops pellets samples.
This document summarizes the synthesis and spectral analysis of a novel benzyl derivative of ciprofloxacin (Cip-D) and its copper(II) and cobalt(II) complexes. Cip-D was synthesized by reacting ciprofloxacin with benzyl chloride in the presence of triethylamine to introduce an amide group. Spectral analysis using 1H NMR, IR, and mass spectroscopy confirmed the structure of Cip-D and indicated bonding between the metal ions and Cip-D in the complexes. Analysis showed shifts in peaks for the complexes, indicating coordination between the metal ions and Cip-D. The Cip-D and its Cu(II) and Co(II)
A STUDY ON FORMATION OF SALYCILIC ACID FORMALDEHYDE POLYMER SAMPLEEDITOR IJCRCPS
Condensation of salicylic acid (0.02 mole) with formaldehyde (0.016 mole) in presence of aqueous 40% H2SO4.
Keywords: pipette,thermometer,spectro-photometer,conicalflakk,waterbath.
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
All manuscripts are subject to rapid peer review. Those of high quality (not previously published and not under consideration for publication in another journal) will be published without delay.
This document summarizes the revised NMR data for the alkaloid incartine isolated from Galanthus elwesii. The researchers revised the previously reported NMR data for incartine through 2D NMR experiments. They also isolated four other alkaloids from G. elwesii: hordenine, lycorine, 8-O-demethylhomolycorine, and hippeastrine. In vitro bioactivity studies showed that incartine had no remarkable antiviral or cytotoxic activity and only weakly inhibited acetylcholinesterase.
Glomerella cingulata, a plant pathogen fungus, was able to biotransform (+)-camphorquinone and (-)-camphorquinone into diols with high stereoselectivity and enantioselectivity over 10 days. (+)-Camphorquinone was transformed into (+)-2-exo-3-exo-camphane-2,3-diol with high stereoselectivity. (-)-Camphorquinone was transformed into (+)-2-endo-3-exo-camphane-2,3-diol with high stereo- and enantioselectivity. This is the first report of these specific biotransformations by microorganisms.
Antibody Glycan Analysis with Normal Phase PhyTip ColumnsChris Suh
1) Glycans are complex carbohydrates that are attached to proteins and lipids and play important roles in cellular functions and disease.
2) This study presents methods to fluorescently label and purify glycans from glycoproteins using PhyTip columns containing Sephadex G10 or normal phase resin, enabling their analysis by capillary electrophoresis.
3) Glycoproteins were digested with enzymes to release glycans, which were then labeled with a fluorescent tag and purified using the PhyTip columns to remove excess label prior to profiling and quantification by capillary electrophoresis.
This document summarizes research into separating the enantiomers of lactic acid dimer (lactide) for sustainable bioplastic production. Two promising methods were discovered: 1) Synthesizing and separating diastereomers of lactide with (S)-2-methyl-1-butanol as a chiral auxiliary. 2) Using kinetic discrimination during esterification of lactide with (R)-(-)-myrtenol, which reacted faster with the S enantiomer. (S)-2-methyl-1-butanol formed diastereomers with similar kinetics, but separation was possible by crystallization. (R)-myrtenol showed strong kinetic preference for the S enantiomer. This
This document describes an inter-laboratory evaluation study conducted to validate the use of the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay as a standard method for evaluating the antioxidant capacity of food additives. Fourteen laboratories participated in the study. Five analytical samples - four existing food additives (tea extract, grape seed extract, enju extract, and d-α-tocopherol) and Trolox - were evaluated using the DPPH assay. The results showed good repeatability for measuring antioxidant capacity within laboratories, but greater variability between laboratories. However, expressing the results as Trolox equivalent antioxidant capacity reduced inter-laboratory variability, suggesting the DPPH assay could be
Structural elucidation, Identification, quantization of process related impur...IOSR Journals
Major process related unknown impurity associated with the synthesis of Hydralazine hydrochloride bulk drug was detected by high performance liquid chromatography (HPLC) and was subjected to high resolution accurate liquid chromatography mass spectroscopy (HR/AM-LCMS) for identification. The proposed impurity was isolated from Hydralazine hydrochloride active pharmaceutical ingredient (API) by preparative chromatographic method and was injected on HPLC for comparison of retention time with that of the unknown process related impurity in Hydralazine hydrochloride. The molecular ion peak of preparatively isolated impurity and that of unknown process related impurity in Hydralazine hydrochloride were compared for confirmation. The postulated structure was unambiguously confirmed with the help of HR/AM- LC MS/MS, NMR and FTIR data proposed to be 1-(2-phthalazin-1-ylhydrazino)phthalazine (Hazh Dimer). This impurity of Hydralazine hydrochloride is not been previously reported. A rapid Acquity H-class gradient method with runtime of 15.0min was developed for Quantitation on Unisphere Cyno column and validated for parameters such as accuracy, precision, linearity and range, robustness. The LOD and LOQ of method were 0081% and 0.0246% respectively.
Evaluation of antioxidant and antiradical properties of pomegranate (punica g...Pritam Kolge
Evaluation of antioxidant and antiradical properties
of Pomegranate (Punica granatum L.) seed and defatted
seed extracts
This is Journal Club activity Presentation with the reference of various research papers.
This Presentation Contain following...
#Info about Paper
#Abstract
#Materials
#Methods
#Results
#Discussion
#Conclusion
#References
*Important Methods used
#Moisture content
#Fat content
#Acid value
#Peroxide value
#Oxidative stability index
#Total phenols content
#Preparation of Pomegranate seed extracts and calculate extract yield
#Evaluation of antioxidant properties of Pomegranate seed extracts using
-DPPH radicals scavenging activity
-FRAP assay
#Antioxidant efficiency of seed extract (Oxidative stability extract)
#Statistical analysis
Journal Club Presentation at Bharati Vidyapeeth College of Pharmacy, Kolhapur.
Thanks for Help and Guidance of Dr. P. B. Choudhari (Assistant Professor, Pharmaceutical Chemistry) and Dr. A. J. Shinde (Assistant Professor, Department of Pharmaceutics)
This document describes the synthesis and properties of mixed backbone oligodeoxynucleotides containing both negatively charged phosphodiester linkages and positively charged guanidinium linkages. Specifically, it reports the solid phase synthesis of chimeric guanidinium/phosphodiester oligonucleotides and studies their thermal stability when hybridized to complementary DNA or RNA strands. It also examines the resistance of these chimeras to degradation by exonuclease I enzyme.
Quantitative and Qualitative analysis of Toxicology pharm 402Justas Lauzadis
The document discusses quantitative and qualitative analysis of toxicology compounds. In the qualitative analysis, four compounds were extracted from rabbit serum at different pH levels using liquid-liquid extraction and GC/MS. Two compounds were extracted at basic pH and one at acidic pH, while one compound was not extracted. In the quantitative analysis, reverse phase HPLC was used to analyze malathion concentrations in water samples. Calibration curves were made using standards and an internal standard. The sample analysis found a higher concentration than expected due to loss of product, which was corrected using the internal standard data. Improper pipetting was identified as the source of error.
Four anthraquinone compounds were isolated from the rare southern Illinois lichen Lasallia papulosa. Two compounds, 7-chloroemodin and valsarin, had been previously isolated from this lichen species. The other two compounds, 5-chloro-1-O-methylemodin and 5-chloro-1-O-methyl-β-hydroxyemodin, had only been previously isolated from laboratory-cultured Nephroma laevigatum and were the first isolation from lichens in their natural habitat. The compounds were characterized using various analytical techniques and identified.
The study evaluated the anti-inflammatory activity of the hexane extract and two sesquiterpenes, cacalol and cacalone, isolated from Psacalium decompositum in carrageenan-induced rat paw edema and TPA-induced ear edema models. Both the hexane extract and sesquiterpenes showed dose-dependent inhibition of carrageenan-induced edema. In the TPA-induced model, all tested compounds showed anti-inflammatory activity in a dose-dependent manner. Cacalone showed the most prominent anti-inflammatory activity in both models. The study suggests that some beneficial effects attributed to P. decompositum in traditional medicine can be related to the anti-inflammatory activity
This document summarizes a study on the synthesis and NMR analysis of various Naproxen and Ibuprofen ester derivatives. Several diastereoisomeric Naproxyl-Naproxenate, Naproxyl-Ibuprofenate, and Ibuprofyl-Naproxenate esters were synthesized. Variable temperature NMR experiments showed differences in aromatic ring dynamics between esters, likely due to varying axial rotation speeds. Chiral shift reagent NMR experiments were also performed and provided insights into epimerization levels, assignments of proton signals, and geometries of the ester complexes.
1) The aerial parts of Piquería irinervia yielded a new compound called 1β-glucosyl-piquerol A. Its structure was determined through NMR, IR, UV, and mass spectrometry to be the monoterpene piquerol A glycosidically bonded to glucose.
2) In contrast to piquerol A, 1β-glucosyl-piquerol A did not inhibit seed germination or root growth of test plants.
3) It is proposed that the synthesis of this monoterpene glycoside could be a mechanism for the plant to avoid autotoxicity, while hydrolysis in the soil could release the allelopathic piqu
This document summarizes research on compounds isolated from Calophyllum brasiliense and Mammea americana that have trypanocidal activity against Trypanosoma cruzi, the parasite that causes Chagas disease. Several mammea-type coumarins were isolated from C. brasiliense, including mammea A/BA, A/BB, A/BD, and a shikimic acid derivative. Mammea A/AA was isolated from M. americana. In in vitro tests, mammea A/BA, A/BB, A/AA, and A/BD showed potent activity against T. cruzi epimastigotes and trypomastigotes. The shikim
1. The authors isolated a new compound, 1β-glucosyl-piquerol A, from Piqueria trinervia, an herb known for its allelopathic effects.
2. Structural analysis using NMR, IR, MS, and chemical derivatization confirmed the compound as a monoterpene glycoside consisting of piquerol A linked to glucose.
3. Unlike piquerol A, 1β-glucosyl-piquerol A did not inhibit seed germination or plant growth, and was inactive against human pathogenic bacteria, suggesting it serves as a non-toxic storage form for the allelochemical piquerol A.
This document summarizes an NMR study of the structures of two triterpenes, Davallene (1) and Adipedatol (2), isolated from Mexican Adiantum capillus-veneris. The authors analyzed the compounds using 2D and 3D NMR techniques including COSY, TOCSY, HSQC, and HMBC to assign proton and carbon signals and determine the structures. Single crystal X-ray diffraction was also used. The NMR data provided connectivity information between protonated carbons, though some isomeric structures remained possible. The analysis began with an identified isopropyl group to determine an unambiguous identification.
1) The heartwood of Lonchocarpus castilloi is highly resistant to attack by drywood termites, but successive extraction reduced this resistance.
2) Extracts of the heartwood and two isolated flavonoids, castillen D and E, deterred feeding and reduced survival of the drywood termite Cryptotermes brevis when impregnated in filter paper, but were not toxic.
3) Termites avoided eating filter paper treated with heartwood extracts in choice tests, showing the extracts have feeding deterrent activity rather than toxicity.
O documento discute o uso de hormônias vegetais na agricultura mexicana. As hormônias vegetais regulam o crescimento e desenvolvimento das plantas e podem ser reproduzidas artificialmente como "reguladores do crescimento vegetal". Estes produtos produzem uma ampla gama de respostas fisiológicas nas plantas e são usados principalmente em culturas de alto valor comercial. No entanto, as hormônias vegetais são frequentemente classificadas incorretamente como "pesticidas".
This document discusses a study that analyzed methanol extracts of Hamelia patens, a medicinal plant used traditionally in Mexico to treat menstrual disorders. The study aimed to 1) determine the alkaloid content of samples from different locations and times of year, and 2) evaluate the extracts' effects on contractions of estrogen-primed rat myometrium. The results showed variations in alkaloid content among samples. All samples relaxed myometrium contractions in a concentration-dependent manner, with samples lacking certain alkaloids displaying a higher relaxant effect. However, the plant extracts were poorer relaxants than the drug verapamil.
This document summarizes a study investigating the anti-asthmatic properties of the plant Argemone platyceras. Methanol extracts of the plant's leaves and flowers, along with isolated compounds, were tested on trachea rings from guinea pigs. Isoquercitrin, one of the compounds isolated from the ethyl acetate fraction of the leaf extract, was found to inhibit contractions induced by carbachol and leukotriene D4, and abolished the response to ovalbumin antigen challenge. Due to these effects on mediators of asthma, the study suggests isoquercitrin could be useful for treating asthma.
This journal article summarizes a study investigating the cytotoxic effects and molecular mechanisms of action of coumarins isolated from Calophyllum brasiliense (mammea A/BA and A/BB) in K562 leukemia cells. The study found that the coumarin mixture induced cytotoxicity in the cancer cells and apoptosis, as shown by TUNEL staining and caspase-3 activation. Genotoxic effects were also observed. Additionally, an in silico analysis found the coumarins complied with criteria for drug-likeness. The results support further development of these natural compounds as potential anticancer agents.
The document summarizes a study that investigated the cytotoxic effects and cell death mechanisms of the naturally occurring coumarin A/AA in various cancer cell lines and normal cells. The results showed that coumarin A/AA was cytotoxic to four cancer cell lines tested, including HeLa cells, and was significantly less toxic to normal peripheral blood cells. In HeLa cells, coumarin A/AA induced cell death through DNA fragmentation but not cell cycle disruption. It was found to induce the early release of the apoptosis-inducing factor AIF from mitochondria, suggesting a caspase-independent cell death pathway. This indicates coumarin A/AA may have potential applications in cancer treatment.
This document summarizes a study on the essential oil compositions of seven Litsea species found in Mexico and their ethnobotanical uses. Gas chromatography-mass spectrometry was used to analyze the foliar essential oils. The species can be grouped based on their main terpenoid compounds. Litsea glaucescens and L. guatemalensis oils correlated with their traditional culinary and medicinal uses. L. glaucescens is widely used as a condiment while L. guatemalensis is used medicinally for fever, digestive issues, and arthritis. Four other species are used locally as spices. The essential oil profiles provide chemotaxonomic data to distinguish the Litsea species.
This document discusses how small data can be effectively analyzed using simple command line tools and scripting languages like Ruby. The key points made are:
1) Most data is small in size and does not require large Hadoop clusters for processing - command line tools and scripting are often much faster for small data workloads.
2) The Unix shell is a powerful programming environment that allows stringing together simple commands into powerful pipelines for analyzing and transforming data in flexible ways.
3) Ruby is a great fit for scripting small data tasks and integrating with Unix tools due to its clean syntax, large standard library, and ability to be used for one-liners or full scripts.
The document summarizes firearms regulations in Colorado. It discusses two US Supreme Court cases (District of Columbia v. Heller and McDonald v. Chicago) that established an individual right to gun ownership. Colorado's constitution also protects this right. The document outlines how Colorado state statutes largely preempt local gun regulations, allowing concealed carry with a permit and restricting local rules around firearm sales, purchases and transportation.
The study determined the structure and stereochemistry of four sesquiterpene lactones isolated from Mexican Asteraceae species using NMR spectroscopy and X-ray crystallography. Budlein A, zaluzanin A, and glaucolides D and E were isolated and their 1H and 13C NMR spectra were completely assigned. Zaluzanin A and glaucolide E crystal structures were also determined. Biological testing found that budlein A and zaluzanin A could relax contractions in rat uterine smooth muscle induced by KCl, but only zaluzanin A could relax contractions induced by oxytocin.
Este documento presenta el programa del Mes Gastronómico y Cultural 2014 en el Valle de Améscoa Comarca Turística Urbasa Estella. El programa incluye degustaciones de pintxos y actividades culturales como conciertos, obras de teatro, talleres y juegos en diferentes pueblos del valle durante los fines de semana de diciembre 2014 y enero 2015.
This document summarizes Amendment 41, which places restrictions on gifts received by Colorado public officials and employees. It prohibits these individuals from receiving gifts over $53 in value without providing consideration in return. It also establishes the Independent Ethics Commission to investigate complaints regarding violations of the amendment. The summary discusses who is covered under the amendment, the prohibitions and exceptions, the complaint process, and penalties for violations. It also notes that local governments can adopt more stringent ethics ordinances under the amendment's home rule provision.
The document summarizes the isolation and characterization of three compounds from the aerial parts of Physalis angulata L. collected in Vietnam. Through chromatographic separation and spectroscopic analysis, the compounds were identified as physalin B (1), physalin G (2), and quercetin 3-O-rutinoside (3). Physalin G (2) was found to inhibit the α-glucosidase enzyme. This is the first report of the α-glucosidase inhibitory activity of physalin G.
Isolation and bioactivity of pentacyclic triterpenoid (betunilic acid) from t...Alexander Decker
This document summarizes research that isolated and identified a pentacyclic triterpenoid compound called Betunilic acid from the bark of the plant Sarcocephalus latifolius. Through a series of extractions and chromatography techniques, the researchers obtained a compound labeled SB-C2. Spectroscopic analysis including NMR, FTIR, and comparisons to literature identified SB-C2 as the pentacyclic triterpenoid Betunilic acid. Tests on various pathogens found Betunilic acid to have antimicrobial activity comparable to the standard drug Sparfloxacin. The isolation of this bioactive compound supports traditional medicinal uses of S. latifolius bark.
Synthesis, characterization and antimicrobial evaluation of novel diethyl (2-...iosrphr_editor
The IOSR Journal of Pharmacy (IOSRPHR) is an open access online & offline peer reviewed international journal, which publishes innovative research papers, reviews, mini-reviews, short communications and notes dealing with Pharmaceutical Sciences( Pharmaceutical Technology, Pharmaceutics, Biopharmaceutics, Pharmacokinetics, Pharmaceutical/Medicinal Chemistry, Computational Chemistry and Molecular Drug Design, Pharmacognosy & Phytochemistry, Pharmacology, Pharmaceutical Analysis, Pharmacy Practice, Clinical and Hospital Pharmacy, Cell Biology, Genomics and Proteomics, Pharmacogenomics, Bioinformatics and Biotechnology of Pharmaceutical Interest........more details on Aim & Scope).
International Journal of Pharmaceutical Science Invention (IJPSI) is an international journal intended for professionals and researchers in all fields of Pahrmaceutical Science. IJPSI publishes research articles and reviews within the whole field Pharmacy and Pharmaceutical Science, new teaching methods, assessment, validation and the impact of new technologies and it will continue to provide information on the latest trends and developments in this ever-expanding subject. The publications of papers are selected through double peer reviewed to ensure originality, relevance, and readability. The articles published in our journal can be accessed online.
ABSTRACT- L-Ascorbic acid derivatives was synthesized on treatment with acetone and acetyl chloride afforded 5,6-acetal of L-ascorbic acid then benzylation of C-2 and C-3 hydroxyl groups of the lactone ring was accomplished using K2CO3 and benzyl bromide in DMF, then deblocking of the 5,6-O,O-protected derivative of L-Ascorbic acid with acetic acid and methanol gave 2,3-O,O-dibenzyl-L-Ascorbic acid. Subsequently mono-tosylation at 6 position of 2,3-O, O-dibenzyl-L-Ascorbic acid was carried out with addition of p-toluenetosylchloride (PTSC) in Pyridine and MDC solvent medium gave 2,3-O,O-dibenzyl-6-O-tosyl-L-Ascorbic acid. All the structures were characterized by 1H NMR, 13C NMR and Mass Spectroscopy.
Key-words- L-Ascorbic acid, 5,6-Acetal, Benzylation, Hydrolysis, Tosylation
Facial and Simple Synthesis of Some New (Pyrazole and Triazole) Coumarin Deri...IOSRJAC
2-oxo-2H-coumarin-3-carbohydrazide (2) which prepared from the reaction of ethyl-2-oxo-2Hcoumarin-3-carboxylate (1) with hydrazine hydrate in ethanol containing a catalytic amount of piperidine mixture consider a good and available starting intermediate for synthesis of series of functionalized coumarins. So, compound (2) was utilized as a key for the synthesis of some new (pyrazole, triazole)-2H- coumarin-2-one derivatives by the reaction with some selected reagents.
Synthesis Characterization And Antimicrobial Activity Of 6- Oxido-1- ((5 -5- ...IOSR Journals
This document describes the synthesis and characterization of several novel carbamate derivatives and their evaluation for antimicrobial activity. Specifically, it details the multi-step synthesis of cyclopropyl/cyclohexyl/terahydro-2H-pyran-4-yl/tetrahydro-2H-thiopyran-4-yl/perfluorophenyl (6-oxido-1-((5-(5-(pyridin-3-yl)-1H-tetrazol-1-yl)-1,3,4-thiadiazol-2-yl)methyl)-4,8-dihydro-1H-[1,3,2]dioxaphosphepino
Design, synthesis, characterization and biological evaluation of 3- (4-(7-chl...iosrjce
Novel thiazolidinone derivatives TQ-VI(1-10) were designed, synthesized and screened for
antimicrobial activity. Synthesis of 3-(4-(7-chloro-2-(4-chlorophenyl) 4-oxo-quinazolin-3(4H)-yl) phenyl) -
2-arylthiazolidin-4-one TQ-VI(1-10) have been achieved from the starting material 2-amino-4-chlorobenzoic
acid TQ-I on cyclization with p-chlorobenzoyl chloride TQ-II to yield 7-chloro-2-(4-chlorophenyl)-4H-3,1-
benzoxazin-4-one,TQ-III, which on treatment with p-phenylindiamine gave 3-(4-aminophenyl)-7-chloro-2-(4-
chlorophenyl)quinazolin-4(3H)-one, TQ-IV in good yield. Then, TQ-IV on reaction with substituted aromatic
aldehydes converted to TQ-V(1-10), which on cyclization with thioglycolic acid gave TQ-VI (1-10). All the
synthesized compounds have been characterized on the basis of IR,
1
H-NMR and mass spectral data. The
compounds containing 4-OH, 4-OCH3 and 3,4,5-(OCH3)3 showed good activity. The title compounds were
screened for qualitative (zone of inhibition) and quantitative antimicrobial activity (MIC) by agar cup plate
method and serial dilution technique, respectively. Among the synthesized compounds in the series, the
compound TQVI4 and TQVI5 were found to exhibit significant antifungal activity at lower concentration of
31.25 µg/ml, against A.niger. The compound TQVI5 and TQVI4 showed zone of inhibition of 17mm and 15mm
against A.niger and C.albicans respectively which is comparable to that of standard drug. The rest of the
analogues in the series displayed weak to moderate antimicrobial activity when compared to the standard
positive controls Ampicillin and Amphotericin B.
The document summarizes a study that isolated and characterized various coumarin compounds from the leaves of Calophyllum brasiliense, including mammea type coumarins. These compounds were tested for their cytotoxic effects against three human tumor cell lines. The mammea coumarins showed the highest cytotoxic activity, with mammea A/BA having an IC50 between 0.04 to 0.59 μM. These compounds and others isolated from C. brasiliense were also tested for inhibition of HIV-1 reverse transcriptase and antibacterial activity, but most were inactive in these assays.
This document summarizes the results of chemical analysis of two types of freshwater macroalgae, Chara sp. and Spirogyra, collected from Bestansur Village in Iraq. High performance liquid chromatography (HPLC) was used to identify and quantify various chemical constituents. HPLC analysis found that both algae contained alkaloids like kaempfertin, isoquinoline, corilagin and colocynthitin. Spirogyra also contained gallic acid. Both algae contained five steroid compounds and Chara sp. was found to contain high levels of tocopherols like alpha-tocopherol. Inductively coupled plasma analysis also identified various elements in the algae
The document summarizes the synthesis and biological evaluation of 3,4,5-trihydroxybenzoic acid derivatives. It presents the objectives, literature review, synthetic scheme, and procedures for synthesizing 14 derivatives. It provides physicochemical and spectral data characterizing the derivatives. The biological evaluation will assess the compounds' antimicrobial, antioxidant, alpha-amylase, and urease inhibitory activities.
Synthesis and antimicrobial activity of some methyl (4- (benzo[d]oxazol-2-yl)...QUESTJOURNAL
1. A series of methyl (4-(benzo[d]oxazol-2-yl)phenyl) carbamodithioate amine derivatives were synthesized by reacting methyl (4-(benzo[d]oxazol-2-yl)phenyl) carbamodithioate with various amines.
2. The synthesized compounds were screened for their in vitro growth inhibiting activity against bacteria and fungi. Compounds exhibited moderate to high antibacterial and antifungal activity.
3. The structures of the compounds were characterized using spectral data such as IR, NMR, mass spectrometry, and elemental analysis. The compounds were then tested for their antimicrobial properties against various bacteria and fungi.
Synthesis of new 2 h pyrano[3,2-h]quinolines with potential biological activityAlexander Decker
The document summarizes the synthesis of new 2H-pyrano[3,2-h]quinoline derivatives with potential biological activity. 5-halo-8-hydroxyquinoline-7-carboxaldehyde reacted with diethyl malonate to produce ethyl 6-halo-2-oxo-2H-pyrano[3,2-h]quinoline-3-carboxylates, which underwent further reactions to form derivatives containing pyrane, pyrazole, indole and oxadiazino[5,6-b]indole moieties. The biological screening showed some of the pyrano[3,2-h]quinoline derivatives have excellent antibacterial and ant
Synthesis, characterization, in vitro cytotoxic and antioxidant activities of...ijperSS
ABSTRACT
A series of novel (Z)-3-(2-(4-(2-oxo-2H-chromen-3-yl) thiazol-2-yl-)hydrazono)indolin-2-one (8a-8d, 9) were synthesized with various substituted indole derivatives. Structures of the newly synthesized compounds were elucidated by FT-IR, 1H-NMR, 13C-NMR and API-ES Mass spectral data. The in vitro cytotoxic activities of the complexes measurement against the human cancer T-lymphocyte cell lines. In vitro evaluation of these title complexes revealed cytotoxicity from 6.8-18µg/mL against CEM, 9.2-21µg/mL against L1210, 10-19µg/mL against Molt4/C8, 8-12µg/mL against HL60 and 8-16µg/mL against BEL7402. Coumarin derivatives 8c and 8d showed that quite significant anticancer activities. The antioxidant activity of the synthesized compounds was evaluated by DPPH scavenging method. Compounds 8c, 8d and 9 showed significant antioxidant activity compared with that of standard drug, ascorbic acid.
Key words: Coumarin, DPPH, Cytotoxic activity.
1) A new potential anticancer agent, 1,4,5,8-Tetrakis-[(2-N,N-dimethylaminoethyl)amino]anthraquinone (T-2), was synthesized from 1,4,5,8-tetrachloroanthraquinone and characterized.
2) T-2 demonstrated greater cytotoxicity against human breast cancer cells (BOT-2 cell line) than the existing drugs mitoxantrone and doxorubicin in in vitro assays.
3) In in vivo assays using mice with B16 melanoma, T-2 showed an equal life span and tumor response compared to mitoxantrone, but was less toxic.
This document describes the synthesis of novel spirooxindole derivatives via a three-component 1,3-dipolar cycloaddition reaction. Various spirooxindole-spiropiperidinone-pyrrolidine and spirooxindole-spiropiperidinone-pyrrolizine derivatives were synthesized in good yields from isatin, sarcosine or L-proline, and Knoevenagel adducts under optimized reaction conditions. The antimicrobial activities of the synthesized compounds were evaluated, with some compounds exhibiting excellent activity against bacteria and fungi, comparable or superior to standard antimicrobial drugs.
Novel Hybrid Molecules of Isoxazole Chalcone Derivatives: Synthesis and Study...Ratnakaram Venkata Nadh
medicine due to their significant role in the treatment of different health problems.
Methods: We have synthesized new series of isoxazole-chalcone conjugates (14a-m) by the
Claisen-Schmidt condensation of suitable substituted acetophenones with isoxazole aldehydes (12a-d).
In vitro cytotoxic activity of the synthesized compounds was studied against four different selected
human cancer cell lines by using sulforhodamine B (SRB) method.
Results: The adopted scheme resulted in good yields of new series of isoxazole-chalcone
conjugates (14a-m). Potent cytotoxic activity was observed for compounds -14a, 14b, 14e, 14i, 14j
and 14k against prostate DU-145 cancer cell line.
Conclusion: The observed potent cytotoxic activities were due to the presence of 3,4,5-
trimethoxyphenyl group.
Phytochemical investigation of the methanolic extract of Launaea intybacea yielded eleven compounds, which were characterized using NMR, mass spectrometry, and by comparison to reported data. The compounds showed antioxidant activity in DPPH radical scavenging assays and inhibitory effects against acetylcholinesterase, butyrylcholinesterase, and lipoxygenase enzymes. This is the first report of these bioactive compounds isolated from L. intybacea.
A friedelane type triterpene from prosopis africanaAlexander Decker
The document describes the isolation and characterization of a friedelane type triterpene, compound J29, from the stem bark of Prosopis africana. J29 was isolated through column chromatography of the chloroform fraction obtained from ethyl acetate extraction of P. africana stem bark. Spectroscopic analysis including IR, 1H NMR, 13C NMR and 2D NMR identified compound J29 as friedelin, a triterpene being reported for the first time from P. africana.
A friedelane type triterpene from prosopis africanaAlexander Decker
The document describes the isolation and characterization of a friedelane type triterpene, compound J29, from the stem bark of Prosopis africana. J29 was isolated through column chromatography of the chloroform fraction obtained from ethyl acetate extraction of P. africana stem bark. Spectroscopic analysis including IR, 1H NMR, 13C NMR and 2D NMR identified compound J29 as friedelin, a triterpene being reported for the first time from P. africana. Friedelin showed characteristic signals in the IR, 1H NMR and 13C NMR spectra that matched literature data for the proposed triterpene skeleton.
Similar to 2004 hiv 1 inhibitory compounds from calophyllum brasiliense leaves (20)
Este documento presenta la tesis de maestría de Eduardo Antonio Aguilar Bañuelos sobre la evaluación de la actividad relajante de los metabolitos secundarios de Calophyllum brasiliense sobre la contractilidad del íleon de rata. El documento incluye la introducción, antecedentes, planteamiento del problema, hipótesis, objetivos, materiales y métodos, resultados, discusión y conclusión. El objetivo principal fue evaluar el efecto de los extractos y compuestos de C. brasiliense sobre la contracción del músculo liso del íleon inducida
Este documento presenta los resultados de un estudio ecológico químico de Vismia mexicana. El objetivo fue determinar la herbivoría de las hojas en dos fechas, identificar compuestos inducidos por herbivoría e investigar propiedades insecticidas. Los resultados mostraron mayor herbivoría en octubre que enero, y la presencia de alcanos de cadena larga en hojas dañadas y frutos. Estos compuestos inhibieron la alimentación de Spodoptera frugiperda en bioensayos. La síntesis de
Este documento presenta los resultados de un estudio sobre los metabolitos secundarios del árbol tropical Vismia mexicana y su actividad sobre la transcriptasa reversa del VIH-1. El extracto de metanol de las hojas de V. mexicana inhibió en un 84% la actividad de la enzima transcriptasa reversa del VIH-1 in vitro. El extracto se fraccionó obteniendo varias fracciones, las cuales se aislaron y caracterizaron compuestos. Algunas fracciones inhibieron significativamente la transcriptasa reversa del VIH-1, siendo las más pot
La tesis estudia los metabolitos secundarios de las especies de Clusia guatemalensis y Clusia quadrangula y su actividad sobre las enzimas transcriptasa reversa y proteasa del VIH-1. En estudios previos, extractos de estas dos especies mostraron una inhibición mayor al 70% sobre la transcriptasa reversa. El objetivo es aislar y caracterizar los compuestos responsables de esta actividad. Se realizó un fraccionamiento de los extractos y se aislaron y caracterizaron varios triterpenos de Clusia guatemalensis. Los extractos se probaron
Este documento presenta los resultados de un estudio sobre el efecto de diferentes tratamientos nutricionales en el crecimiento y producción de metabolitos secundarios de plántulas de Calophyllum brasiliense establecidas en invernadero. El estudio encontró que C. brasiliense presenta dos quimiotipos en México que difieren en su composición química. Los tratamientos nutricionales no afectaron el quimiotipo de las plántulas. El análisis edafológico mostró pequeñas diferencias entre los suelos de
Este documento presenta la tesis de Alicia Fonseca Muñoz para obtener el título de Biólogo. La tesis evalúa la distribución geográfica de quimiotipos de Calophyllum brasiliense en México y la actividad hipoglucemiante del ácido apetálico. El trabajo fue realizado bajo la dirección del Dr. Ricardo Reyes Chilpa y con el apoyo de varios miembros del personal académico y equipos de investigación.
Este documento presenta la tesis de Irma Sustaita Aranda para obtener el título de Bióloga. El resumen analiza la contribución al conocimiento taxonómico de los géneros Calophyllum (Guttiferae) identificando quimiotipos de C. rekoi Standl y C. brasiliense Cambess. La tesis fue dirigida por el Dr. Ricardo Reyes Chilpa y agradece el apoyo de varios sinodales, profesores y personal de instituciones como la UNAM. Finalmente, la autora dedica su tesis
Este documento presenta el resumen de una tesis de licenciatura sobre el efecto de metabolitos secundarios de la planta Calophyllum brasiliense en hongos que colonizan sus hojas. El estudio se realizó de forma in vitro bajo la dirección del Dr. Ricardo Reyes Chilpa y la M.C. Guadalupe Vidal Gaona en los laboratorios de la UNAM. El trabajo fue financiado por el proyecto "Búsqueda de Compuestos de Origen Vegetal con Posible Actividad Inhibitoria de la Transcriptasa Reversa del Virus de In
La Unión Europea ha acordado un embargo petrolero contra Rusia en respuesta a su invasión de Ucrania. El embargo prohibirá la mayoría de las importaciones de petróleo ruso a la UE y se implementará de manera gradual durante los próximos seis meses. La medida es la sanción económica más dura contra Rusia hasta la fecha y tiene como objetivo aumentar la presión sobre el gobierno de Putin para que detenga la guerra.
Esta tesis estudia las xantonas aisladas de la madera de Calophyllum brasiliensis y su actividad biológica. La tesis fue realizada por Elizabeth Estrada Muñiz en el Laboratorio 2-8 del Instituto de Química de la UNAM bajo la dirección del Dr. Ricardo Reyes Chilpa y el Dr. Manuel Jiménez Estrada. El trabajo fue aprobado y cumple con los requisitos para otorgar a Elizabeth Estrada Muñiz el título de Bióloga.
Este documento presenta la tesis de Julio César García Zebadúa para obtener el grado de Doctor en Ciencias. El trabajo caracteriza químicamente y evalúa la actividad antiviral contra el VIH-1 del árbol tropical Calophyllum brasiliense recolectado en Chiapas, México. Se aislaron y caracterizaron compuestos fenólicos y se evaluó su actividad anti-transcriptasa del VIH-1, citotoxicidad y toxicidad aguda. Los resultados mostraron que algunos compuestos aislados inhiben la transcriptasa reversa del VIH-
Este documento presenta la tesis de Dagoberto Erasmo Alavez Solano para obtener el grado de Doctor en Ciencias Biología. El trabajo estudia la química taxonómica del género Lonchocarpus y la actividad biológica de metabolitos aislados. Se aislaron y caracterizaron compuestos de cinco especies de Lonchocarpus y se evaluó su actividad citotóxica y antifúngica. Adicionalmente, se realizó un análisis quimiotaxonómico del género basado en la pre
La incidencia del VIH-1 ha aumentado drásticamente, motivando la búsqueda de nuevos fármacos. C. brasiliense produce calanólidos activos contra la TR del VIH-1. Este trabajo demuestra que el cultivo de tejidos vegetales es una técnica útil para la producción de estos metabolitos. Se evaluaron diferentes reguladores de crecimiento en explantes de hojas y semillas de C. brasiliense para establecer cultivos de callo. La mayor inducción de callo en semillas ocurrió con BAP 8.88 μM + PIC
Este documento describe el aislamiento e identificación de la 4'-hidroxi-dehidrokavaina de las raíces de Brongniartia intermedia, una leguminosa mexicana. Se evaluó el efecto anticoagulante de este compuesto en ratones, mostrando un efecto significativo similar a la warfarina. Esto sugiere que la 4'-hidroxi-dehidrokavaina podría tener un mecanismo de acción anticoagulante similar al de la warfarina debido a similitudes estructurales. El documento también provee ant
Este documento describe el aislamiento e identificación de la 4'-hidroxi-dehidrokavaina de las raíces de Brongniartia intermedia, una leguminosa mexicana. Se evaluó el efecto anticoagulante de este compuesto en ratones, mostrando un efecto significativo similar a la warfarina. Esto sugiere que el mecanismo de acción podría ser similar, posiblemente debido a semejanzas estructurales. También se discuten las propiedades y usos de las estirilpironas aisladas de otras
1) O documento discute as plantas usadas no tratamento de picadas de cobras no México, revisando a química e farmacologia destas plantas.
2) Muitos metabólitos secundários de origem vegetal, como isoflavonóides, triterpenóides, alcaloides e taninos, mostraram atividade contra venenos de cobras.
3) As plantas mexicanas pertencem principalmente às famílias Asteraceae, Leguminosae e Euphorbiaceae, com predominância das Papilionoideae dentro das Leg
Este documento describe un estudio sobre la actividad citotóxica y genotóxica de una mezcla de compuestos de mammea (A/BA + A/BB) aislados de las hojas de Calophyllum brasiliense sobre células leucémicas humanas K562. Los resultados mostraron que la mezcla induce apoptosis en las células K562 a través de daño genotóxico, como se evidencia por la fragmentación del ADN y daño en el ensayo de Cometa. La mezcla tuvo una IC50 de 43mM contra las células K562
Este documento resume um estudo sobre os efeitos tóxicos e antitumorais da jacareubina em ratos. A jacareubina é uma xantonas isolada da casca de Calophyllum brasiliense que mostrou atividade citotóxica em linhas celulares tumorais humanas, inibindo a proliferação celular e induzindo apoptose. O estudo determinou a dose letal média da jacareubina em ratos e seu potencial antineoplásico em ratos inoculados com células tumorais, avaliando o desenvolvimento
The technology uses reclaimed CO₂ as the dyeing medium in a closed loop process. When pressurized, CO₂ becomes supercritical (SC-CO₂). In this state CO₂ has a very high solvent power, allowing the dye to dissolve easily.
Current Ms word generated power point presentation covers major details about the micronuclei test. It's significance and assays to conduct it. It is used to detect the micronuclei formation inside the cells of nearly every multicellular organism. It's formation takes place during chromosomal sepration at metaphase.
Immersive Learning That Works: Research Grounding and Paths ForwardLeonel Morgado
We will metaverse into the essence of immersive learning, into its three dimensions and conceptual models. This approach encompasses elements from teaching methodologies to social involvement, through organizational concerns and technologies. Challenging the perception of learning as knowledge transfer, we introduce a 'Uses, Practices & Strategies' model operationalized by the 'Immersive Learning Brain' and ‘Immersion Cube’ frameworks. This approach offers a comprehensive guide through the intricacies of immersive educational experiences and spotlighting research frontiers, along the immersion dimensions of system, narrative, and agency. Our discourse extends to stakeholders beyond the academic sphere, addressing the interests of technologists, instructional designers, and policymakers. We span various contexts, from formal education to organizational transformation to the new horizon of an AI-pervasive society. This keynote aims to unite the iLRN community in a collaborative journey towards a future where immersive learning research and practice coalesce, paving the way for innovative educational research and practice landscapes.
Or: Beyond linear.
Abstract: Equivariant neural networks are neural networks that incorporate symmetries. The nonlinear activation functions in these networks result in interesting nonlinear equivariant maps between simple representations, and motivate the key player of this talk: piecewise linear representation theory.
Disclaimer: No one is perfect, so please mind that there might be mistakes and typos.
dtubbenhauer@gmail.com
Corrected slides: dtubbenhauer.com/talks.html
The binding of cosmological structures by massless topological defectsSérgio Sacani
Assuming spherical symmetry and weak field, it is shown that if one solves the Poisson equation or the Einstein field
equations sourced by a topological defect, i.e. a singularity of a very specific form, the result is a localized gravitational
field capable of driving flat rotation (i.e. Keplerian circular orbits at a constant speed for all radii) of test masses on a thin
spherical shell without any underlying mass. Moreover, a large-scale structure which exploits this solution by assembling
concentrically a number of such topological defects can establish a flat stellar or galactic rotation curve, and can also deflect
light in the same manner as an equipotential (isothermal) sphere. Thus, the need for dark matter or modified gravity theory is
mitigated, at least in part.
The ability to recreate computational results with minimal effort and actionable metrics provides a solid foundation for scientific research and software development. When people can replicate an analysis at the touch of a button using open-source software, open data, and methods to assess and compare proposals, it significantly eases verification of results, engagement with a diverse range of contributors, and progress. However, we have yet to fully achieve this; there are still many sociotechnical frictions.
Inspired by David Donoho's vision, this talk aims to revisit the three crucial pillars of frictionless reproducibility (data sharing, code sharing, and competitive challenges) with the perspective of deep software variability.
Our observation is that multiple layers — hardware, operating systems, third-party libraries, software versions, input data, compile-time options, and parameters — are subject to variability that exacerbates frictions but is also essential for achieving robust, generalizable results and fostering innovation. I will first review the literature, providing evidence of how the complex variability interactions across these layers affect qualitative and quantitative software properties, thereby complicating the reproduction and replication of scientific studies in various fields.
I will then present some software engineering and AI techniques that can support the strategic exploration of variability spaces. These include the use of abstractions and models (e.g., feature models), sampling strategies (e.g., uniform, random), cost-effective measurements (e.g., incremental build of software configurations), and dimensionality reduction methods (e.g., transfer learning, feature selection, software debloating).
I will finally argue that deep variability is both the problem and solution of frictionless reproducibility, calling the software science community to develop new methods and tools to manage variability and foster reproducibility in software systems.
Exposé invité Journées Nationales du GDR GPL 2024
When I was asked to give a companion lecture in support of ‘The Philosophy of Science’ (https://shorturl.at/4pUXz) I decided not to walk through the detail of the many methodologies in order of use. Instead, I chose to employ a long standing, and ongoing, scientific development as an exemplar. And so, I chose the ever evolving story of Thermodynamics as a scientific investigation at its best.
Conducted over a period of >200 years, Thermodynamics R&D, and application, benefitted from the highest levels of professionalism, collaboration, and technical thoroughness. New layers of application, methodology, and practice were made possible by the progressive advance of technology. In turn, this has seen measurement and modelling accuracy continually improved at a micro and macro level.
Perhaps most importantly, Thermodynamics rapidly became a primary tool in the advance of applied science/engineering/technology, spanning micro-tech, to aerospace and cosmology. I can think of no better a story to illustrate the breadth of scientific methodologies and applications at their best.
Unlocking the mysteries of reproduction: Exploring fecundity and gonadosomati...AbdullaAlAsif1
The pygmy halfbeak Dermogenys colletei, is known for its viviparous nature, this presents an intriguing case of relatively low fecundity, raising questions about potential compensatory reproductive strategies employed by this species. Our study delves into the examination of fecundity and the Gonadosomatic Index (GSI) in the Pygmy Halfbeak, D. colletei (Meisner, 2001), an intriguing viviparous fish indigenous to Sarawak, Borneo. We hypothesize that the Pygmy halfbeak, D. colletei, may exhibit unique reproductive adaptations to offset its low fecundity, thus enhancing its survival and fitness. To address this, we conducted a comprehensive study utilizing 28 mature female specimens of D. colletei, carefully measuring fecundity and GSI to shed light on the reproductive adaptations of this species. Our findings reveal that D. colletei indeed exhibits low fecundity, with a mean of 16.76 ± 2.01, and a mean GSI of 12.83 ± 1.27, providing crucial insights into the reproductive mechanisms at play in this species. These results underscore the existence of unique reproductive strategies in D. colletei, enabling its adaptation and persistence in Borneo's diverse aquatic ecosystems, and call for further ecological research to elucidate these mechanisms. This study lends to a better understanding of viviparous fish in Borneo and contributes to the broader field of aquatic ecology, enhancing our knowledge of species adaptations to unique ecological challenges.
2. 1472 Vol. 27, No. 9
in water overnight. Elution started with water, followed by
50% methanol, and finally, absolute methanol. The eluates
were collected, combined and evaporated to dryness. The
other part of the methanol extract was macerated with EtOAc
obtaining an insoluble fraction. This material was positive
for tannins with 1% gelatine–NaCl solution, and 3% ferric
chloride–30% sulfuric acid.
Compound 3 (Apetalic Acid): Yellow oil. HR-FAB-MS
m/z: 389.1963 (Calcd for CHO: 389.1965). FAB-MS
22296m/z: 389 (M1), 373, 329. [a ]2553° (c1.5, CHCl).
D
31H-NMR (CDCl) and 13C-NMR (CDCl) data were found to
33be in good agreement with the literature values.12)
Compound 4 (Isoapetalic Acid): Yellow oil. HR-FAB-MS
m/z: 389.1963 (Calcd for CHO: 389.1965). FAB-MS
22296m/z: 389 (M1), 373, 329. [a ]25D
16.1° (c1.0, CHCl).
31H-NMR (CDCl3) and 13C-NMR (CDCl3) data were found to
be in good agreement with the literature values.13)
Compound 5 (Structural Isomer of Isoapetalic Acid): Yel-low
oil. 1H-NMR (CDCl3) d : 0.86 (3H, t, J7.0 Hz, 24-
CH), 1.14 (2H, m, 23-CH), 1.2 (3H, d, J7.0 Hz, 16-CH),
3231.44 (3H, s, 18-CH), 1.44 (3H, s, 17-CH), 1.49 (3H, d,
33J6.1 Hz, 15-CH), 1.88 (2H, m, 22-CH), 2.54 (1H, dq, J32
11, 7 Hz, 3-H), 2.76 (1H, dd, J15.0, 7.0 Hz, 20-H), 2.86
(1H, dd, J15.0, 8.0 Hz, 20-H), 3.74 (1H, m, 19-H), 4.16
(1H, m, 2-H), 5.45 (1H, d, J10.0 Hz, 10-H), 6.53 (1H, d,
J10.0 Hz, 11-H), 12.70 (1H, s, 5-OH). 13C-NMR (CDCl)
3d : 10.1 (C-16), 14.0 (C-24), 19.6 (C-15), 20.9 (C-23), 28.2
(C-17), 28.3 (C-18), 30.3 (C-19), 35.3 (C-22), 45.7 (C-3),
78.0 (C-9), 78.8 (C-2), 101.0 (C-12), 101.6 (C-14), 115.8 (C-
11), 125.7 (C-10), 155.1 (C-7, C-13), 198.7 (C-4). EI-MS
m/z: 389 (M1), 373, 271. [a ]2528° (c1.0, CHCl).
D
3Compound 6 (()-Calanolide A): Yellow oil. HR-FAB-MS
m/z: 393.1680 (Calcd for CHONa: 393.1678). FAB-MS
22265m/z: 371 (M1), 353, 299. [a ]25D
48.2° (c0.5,
CHCl). 1H-NMR (CDCl) and 13C-NMR (CDCl) data were
333found to be in good agreement with the literature values.1)
Compound 7 (()-Calanolide B): White needles, mp
176—179 °C. HR-FAB-MS m/z: 393.1680 (Calcd for
CHONa: 393.1678). FAB-MS m/z: 371 (M1), 353,
22265299. [a ]2538.6° (c0.5, acetone). 1H-NMR (CDCl) and
D
313C-NMR (CDCl3) data were found to be in good agreement
with the literature values.1)
Compound 8 (()-Calanolide C): Yellow oil. HR-FAB-MS
m/z: 393.1685 (Calcd for C22H26O5Na: 393.1678). FAB-MS
m/z: 371 (M1), 353, 299. [a ]D
2596.3° (c1.0,
CHCl). 1H-NMR (CDCl) and 13C-NMR (CDCl) data were
333found to be in good agreement with the literature values.14)
Compound 9 (Soulattrolide): Light yellow needles, mp
177—181 °C. HR-FAB-MS m/z: 427.1526 (Calcd for
CHONa: 427.1521). FAB-MS m/z: 405 (M1), 387,
25245371. [a ]2514° (c0.25, CHCl). 1H-NMR (CDCl) and
D
3313C-NMR (CDCl3) data were found to be in good agreement
with the literature values.3)
Biological Assays Antiviral activity of C. brasiliense
fractions were evaluated by three successive assays. HIV-1
RT inhibition was first screened, and those fractions that
showed inhibition over 70% were selected for the next bioas-say.
Cytotoxic effect of the fractions was examined on human
lymphocytes cell lines. Non toxic fractions were selected for
the last bioassay, which consisted on determining inhibition
of HIV-1 IIIb/LAV replication. Nevirapine, a non nucleoside
reverse transcriptase inhibitor (NNRTI) was used as positive
control.
HIV-1 RT Inhibition Assay Fractions and pure com-pounds
were evaluated by a non-radioactive immuno and col-orimetric
assay (Lenti RT Activity Assay, Cavidi Tech).15)
Assay was performed according to the protocol provided by
manufacturers. Each fraction was dissolved in DMSO and
tested at 50m g/ml. Concentration tested for pure compounds
was 1mM. IC50 values were calculated for most active com-pounds
(over 70%).
Toxic Effect on Human Lymphocytes Cell Line The
cytotoxic effect of anti HIV-1 RT active fractions were deter-mined
on human lymphocytic MT2 cells. The assay was per-formed
as follows: MT2 cells were cultured in RPMI-1640
medium supplemented with 10% fetal bovine serum,
0.25m g/ml of streptomycin and 100m g/ml of penicillin G, in
presence of the fractions. Culture was maintained at 37 °C
under 5% CO2 humidified atmosphere. Fractions were dis-solved
in DMSO and tested at 50m g/ml. After 48 h, cellular
death was assessed by direct microscopic examination of try-pan
blue stained cells. Results were compared with a control
of MT2 free of extract.
Inhibition of HIV-1 IIIb/LAV Replication Inhibition of
viral replication by fractions was measured in a coculture of
IIIb/LAV-Molt4 cells and non-infected MT2 cells in the pres-ence
of the fractions. Concentration of fractions and condi-tions
of culture were the same as those described for the toxi-city
assay. After 48 h inhibition of viral replication was mea-sured
by a p24 antigen enzyme immunoassay (Genetic Sys-tems
HIV-1Ag EIA, Bio-Rad) performed in the culture su-pernatant.
RESULTS
Most of the fractions obtained from the C. brasiliense
hexane leaves extract showed low HIV-1 RT inhibition, how-ever,
fractions 18 and 19 showed high inhibition (over 70%)
(Table 1). Both fractions were non toxic to MT2 human lym-phocytes
(Fig. 1A), and also strongly inhibited IIIb/LAV
replication (Fig. 1B). Isolation of the pure compounds from
these fractions was performed by chromatography, obtaining
compounds 3 to 9 (Fig. 2). All of them were tested, but only
compounds 6, 7 and 9 showed a potent inhibition on HIV-1
RT. IC50 were calculated for these compounds, that were
Table 1. Evaluation of HIV-1 Inhibitory Properties of Fractions from
Calophyllum brasiliense Leaves Extracts
Fraction/extract HIV-1 RT inhibition (%)
Hexane
1—17 40
18 74.83.3
19 75.53.7
20—27 40
Acetone
1 12.73.1
2 59.53.5
3 28.21.7
Methanol
EtOAc insoluble fraction 74.21.6
Extract after polyamide column 38.64.9
Values are meansS.D., n=3.
3. September 2004 1473
0.34, 0.5 and 0.66m M/ml, respectively. Compound 8 was
moderately active (50 to 70% inhibition), while compounds 4
and 5 exhibited low inhibition. Compound 3 was inactive
(Table 2). Compounds 1 and 2 were also isolated from the
hexane extract, but any of them was able to inhibit HIV-1 RT
(Table 2).
Regarding to acetone extract, fractions 1, 2 and 3 were
evaluated for HIV-1 RT inhibition but only fraction 2 showed
moderate activity (Table 1). This fraction analyzed by TLC
suggested that contains traces of calanolides. Amentoflavone
(10) was also obtained from fraction 2 and tested, showing
low HIV-1 RT inhibition (Table 2). This compound showed a
very strong cytotoxic effect on MT2 cells (2.0105 cells)
when we compared with control free of substance.
The methanol extract showed high HIV-1 RT inhibitory
activity (83.3%), however, this value decreased to 38.6%
after tannin removal (Table 1). EtOAc insoluble fraction from
methanol extract was able to inhibit HIV-1 RT activity and
showed low cytotoxicity (Fig. 1A), nevertheless it was not
able to inhibit IIIb/LAV replication (Fig. 1B).
DISCUSSION
The chemical analysis indicates that main compounds of
C. brasiliense hexane extract from the leaves are two triter-penes,
friedelin (1) and canophyllol (2), and three chro-manone
carboxylic acids, apetalic acid (3), isoapetalic acid
(4) and a structural isomer of isoapetalic acid (5). The minor-ity
compounds are four dipyranocoumarins, ()-calanolide
A (6), ()-calanolide B (7), ()-calanolide C (8) and soulat-trolide
(9).
The apetalic acid (3) has been previously isolated as its
methyl ester from the bark of C. brasiliense seed kernels.12)
Isoapetalic acid (4) and its structural isomer (5) have been
isolated as their methyl esters from the bark of C.
bracteatum, C. calaba var. calaba, C. moonii and C. trapezi-folium.
13)
It is interesting to note that the main compounds, triter-penes
and chromanone carboxylic acids, found in the hexane
extract were inactive or showed a low inhibition on HIV-1 RT
(Table 2). On the other hand, the minority compounds ()-
calanolide A (6), ()-calanolide B (7) and soulattrolide (9)
were identified as the active compounds against HIV-1 RT.
These compounds have been previously isolated from the
fruit, twigs, bark and latex of different Calophyllum Asiatic
species.1,3,4) Recently, ()-calanolide A (6) and ()-calano-lide
B (7) were isolated from the stem bark of C. brasiliense
from Brazil,16) however, this is the first time that these
dipyranocoumarins are found in the leaves. Both calanolides
are considered as non nucleoside reverse transcriptase in-hibitors
(NNRTI) that can inhibit primarily HIV-1 RT, but
fail to inhibit HIV-2 RT. They interact allosterically with the
RT, altering its structural conformation, resulting in a partial
or total disruption of the RT catalityc complex, template-primer,
and the substrate.17) Specifically, ()-calanolide A in-hibits
HIV-1 RT by binding two sites, one competitive and
other noncompetitive.18) It is considered as a unique inhibitor
among NNRTIs,19) since it is able to inhibit the AZT resistant
variant which bears two mutations at codon 181, tyrosine
Æcysteine (Y181C), and codon 131, leucineÆasparagine
(L103N).20) Most NNRTIs are not able to inhibit the variant
bearing the Y181C amino acid mutation.21) The importance
of ring D (2,3-dimethylcroman-4-ol) for HIV-1 inhibitory
properties of calanolides A and B, inophyllums and corda-tolides
has been thoroughly demonstrated.22,23) Highest in-hibitory
activity of HIV-1 RT has been observed for calano-lide
A that posses trans configuration between methyl groups
at C-10 and C-11, while other configurations led to a reduc-tion
in potency. An oxygenated function at C-12, and sub-stituents
at C-4 are also relevant for HIV-1 RT inhibitory ac-tivity
following the series propylphenylmethyl.24)
Regarding compound 8, Kashman et al., 19921) reported
the isolation of ()-calanolide C from the fruit and twigs of
C. lanigerum. However, the proposed structure was reviewed
and corrected by McKee et al., 1995 after obtaining the syn-thetic
product.14) The original assignments for ()-calanolide
C proposed by Kashman et al., 19921) are actually those of
pseudocalanolide C.14) The NMR chemical shifts observed
for the compound 8 here isolated, led to its identification as
()-calanolide C according to data reported by McKee et al.,
1995.14) Diagnostic signals were 6.62 for H-8 and 5.07 for H-
12 as well as 116.6 for C-8, 106.5 for C-8a, 62.9 for C-12
and 105.8 for 12a. To our best knowledge, this is the first
time that ()-calanolide C (8) is obtained as a natural prod-uct,
and evaluated against HIV-1 RT. Although compound 8
exhibits the pharmacophoric ring D, as well as a propyl
group on C-4, it did not show potent inhibition on HIV-1 RT.
This could be due to the b -cis orientation of methyl groups
on C-10 and C-11 (Fig. 2). Therefore our results support
Fig. 1. Toxic and Antiviral Effect of Active Fractions from Hexane and
Methanol Extracts from Calophyllum brasiliense Leaves
(A) Cell viability of lymphocytes MT2. (B) Inhibition of HIV-1 IIIb/LAV replication.
4. 1474 Vol. 27, No. 9
Fig. 2. Isolated Compounds from Calophyllum brasiliense Leaves
the structure–activity relationships (SAR) of Calophyllum
dipyranocoumarins proposed to date.24,25)
Concerning to the acetone extract, we previously reported
that this extract had an inhibitory effect on HIV-1 RT, but it
was also cytotoxic to MT2 human lymphocytes.8) The former
activity could be probably due to traces of calanolides.
Meanwhile, amentoflavone (10) which was devoid of in-hibitory
activity on HIV-1 RT, was cytotoxic to MT2 cells
and therefore could be responsible of the overall acetone ex-tract
toxicity.
It is known that polar extracts may contain tannins and
others like polyphenol compounds able to inhibit HIV-1
RT,11,26) DNA polymerase,27) DNA topoisomerase I and II,28)
and the binding of HIV-1 gp120/CD4 T-cell receptor.11,29)
Since tannins show high affinity for proteins and affect a
number of biochemical reactions, they are generally consid-ered
as unselective inhibitors.30) In our case, the methanol ex-tract
of C. brasiliense leaves showed HIV-1 RT inhibition8)
that could be attributed to tannins.
Our data indicate that anti-HIV properties of C.
brasiliense leaves extracts are due to the presence of ()-
calanolide A (6), ()-calanolide B (7), and soulattrolide (9).
Interestingly, dipyranocoumarins were not detected in C.
brasiliense in a previous study performed by other authors,
using a TLC screening.31) This could arise from the existence
of chemotypes in the species. In Mexico, we have found two
populations of C. brasiliense that differ in the chemistry of
their leaves. One chemotype with chromanones and calano-lides
was object of this paper, while second chemotype that
we have recently reported, contains mammea type coumarins
such as mammea A/BA, A/BB, isomammeigin, mammea
B/BA, B/BB, C/OA, C/OB, B/BA cyclo F and B/BB cyclo F,
Table 2. Evaluation of Pure Compounds Isolated from Calophyllum
brasiliense Leaves against HIV-1 RT
Compounds HIV-1 RT inhibition (%)
1 20.21.6
2 7.62.1
3 2.00.6
4 20.63.2
5 29.71.7
6 81.50.9
7 76.22.2
8 50.72.0
9 77.71.6
10 17.52.4
Control (nevirapine) 82.63.1
Values are meansS.D., n=3.
5. September 2004 1475
all of them inactive against HIV-1 RT.32)
CONCLUSION
The chemical analysis of the extracts of Calophyllum
brasiliense leaves collected in San Andres Tuxtla, state of
Veracruz, showed that the minority compounds dipyra-nocoumarins,
()-calanolide A, ()-calanolide B, and
soulattrolide are the responsible of its anti-HIV properties.
On the other hand, the majority compounds, the chromanone
carboxylic acids, triterpens and biflavonoid were inactive
against HIV-1 RT.
Acknowledgments This research was supported by
grant IN207301 from DGAPA-UNAM. Maira Huerta is
grateful with CONACyT for providing a fellowship and also
with The Nagai Foundation Tokyo for an International Fel-lowship.
Authors are grateful with M. C. Antonio Nieto, the
staff of Natural Products and Pharmacology Laboratory at
Fukuoka University for laboratory facilities and with Ms. Y.
Iwase and Mr. H. Hanazono for the NMR and MS measure-ments.
We are also grateful with Nieves Zavala Segovia,
Rocío Patiño Maya, Luis Velasco Ibarra, Javier Pérez Flores
and Eréndira García for recording some of the spectra.
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