scholarly journals 2α-Acetoxy-15-acetylartemisiifolin, a new Anti-trypanosomal Sesquiterpene Lactone from Mikania guaco

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200
Author(s):  
Ahmed A. Hussein ◽  
Luz Romero ◽  
Jose Luis López-Pérez ◽  
Mahabir P. Gupta
Keyword(s):  
Mass Spectrometry ◽  
Trypanosoma Cruzi ◽  
Sesquiterpene Lactone ◽  
Chemical Structure ◽  
Methanol Extract ◽  
Amastigote Form ◽  
Bioassay Guided Fractionation ◽  
Nmr Techniques

Mikania guaco Bonpl. methanol extract showed an interesting activity against Trypanosoma cruzi with an IC50 of 4 μg/mL. Bioassay-guided fractionation of the methanol extract resulted in the isolation of a new sesquiterpene lactone, 2α-acetoxy, 15-acetylartemisiifolin (1), which was shown to be active (IC50 = 25 μM) against the amastigote form of T. cruzi,. The chemical structure of 1 was elucidated using 2-D NMR techniques and mass spectrometry.

scholarly journals Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa

2015 ◽  
Vol 10 (10) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Manne Sumalatha ◽  
Rachakunta Munikishore ◽  
Aluru Rammohan ◽  
Duvvuru Gunasekar ◽  
Kotha Anil Kumar ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Methanol Extract ◽  
2D Nmr ◽  
Docking Studies ◽  
Selective Inhibitor ◽  
Pueraria Tuberosa ◽  
Nmr Techniques ◽  
Cox 2 ◽  
Plant Sources ◽  
Cox 1

Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species.

scholarly journals Isolation and Identification of an Allelopathic Substance from Hibiscus sabdariffa

2015 ◽  
Vol 10 (5) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Prapaipit Suwitchayanon ◽  
Piyatida Pukclai ◽  
Osamu Ohno ◽  
Kiyotake Suenaga ◽  
Hisashi Kato-Noguchi
Keyword(s):  
Mass Spectrometry ◽  
Chemical Structure ◽  
Methanol Extract ◽  
Hibiscus Sabdariffa ◽  
Aqueous Methanol ◽  
Isolation And Identification ◽  
Reverse Phase Hplc ◽  
Reverse Phase ◽  
H Nmr ◽  
Allelopathic Substance

In this study, an allelopathic substance was isolated from an aqueous methanol extract of Hibiscus sabdariffa L. by column chromatography and reverse phase HPLC. The chemical structure of the substance was determined by 1H NMR spectroscopy and mass spectrometry as trimethyl allo-hydroxycitrate. Trimethyl allo-hydroxycitrate inhibited the growth of cress hypocotyls and roots at concentrations greater than 10 mM. The concentrations required for 50% growth inhibition of the hypocotyls and roots of cress were 20.3 and 14.4 mM, respectively. The inhibitory activity of trimethyl allo-hydroxycitrate suggests that the substance may act as an allelopathic substance of H. sabdariffa.

scholarly journals Phytotoxic Furanocoumarins from the Shoots of Semenovia Transiliensis

2012 ◽  
Vol 7 (10) ◽  
pp. 1934578X1200701
Author(s):  
Shobha Sondhia ◽  
Stephen O. Duke ◽  
Solomon Green ◽  
Nadezhda G. Gemejiyeva ◽  
Leonid K. Mamonov ◽  
...  
Keyword(s):  
Methylene Chloride ◽  
Methanol Extract ◽  
Environmental Issues ◽  
Moderate Activity ◽  
Test Species ◽  
Natural Herbicides ◽  
Phytotoxic Activity ◽  
Bioassay Guided Fractionation ◽  
Nmr Techniques ◽  
Weed Resistance

Discovery of novel, natural herbicides has become important to manage increasing weed resistance to synthetic herbicides and environmental issues. The systematic bioassay-guided fractionation and purification of the methylene chloride/methanol extract of the shoots of Semenovia transiliensis led to the isolation of several phytotoxic compounds. Lactuca sati v a L. (lettuce, a dicot) and Agrostis stolonifera L. (bentgrass, a monocot) bioassays were used to identify and isolate the phytotoxic fractions. A number of furanocoumarin compounds isolated from S. transiliensis shoots were phytotoxic to both test species. These included psoralen, isopsoralen, heratomin, isopentenyloxyisobergapten, imperatorin, bergapten, xanthotoxin, heraclenin, and heraclenol. All the active secondary metabolites isolated from the shoots of S. transiliensis were furanocoumarins. Identification of these was accomplished using mass spectrometry and 1- and 2-dimensional NMR techniques. Phytotoxic activity of isolated compounds was evaluated in a dose–response manner from 0.3 to 1000 μM. In general, all of the compounds were more active on A. stolonifera than L. sativa. Bergaptin and xanthotoxin were the most active of the compounds, with moderate activity at 100 μM. Imperatorin and xanthotoxin inhibited growth of Lemna paucicostata Hegelm. by 50% at 29 and 60 μM, respectively. Our results show that S. transiliensis is rich in furanocoumarins, which are probably involved in various aspects of the chemical ecology of the species. Unfortunately, the general cytotoxicity of furanocoumarins makes them an unlikely candidate for pesticide discovery.

Rarely Occurring Natural Products Isolated from Vincetoxicum stocksii

2019 ◽  
Vol 41 (4) ◽  
pp. 695-695
Author(s):  
Saima Khan Saima Khan ◽  
Muhammad Imran Tousif Muhammad Imran Tousif ◽  
Naheed Raiz Naheed Raiz ◽  
Mamona Nazir Mamona Nazir ◽  
Mahreen Mukhtar Mahreen Mukhtar ◽  
...  
Keyword(s):  
Natural Products ◽  
Methanol Extract ◽  
High Resolution Mass Spectrometry ◽  
Ethyl Acetate Fraction ◽  
2D Nmr ◽  
Ethyl Carbamate ◽  
Carbamic Acid ◽  
Nmr Analysis ◽  
Nmr Techniques ◽  
Resolution Mass

Silica gel column chromatography of the ethyl acetate fraction of methanol extract of Vincetoxicum stocksii resulted in the separation of three new rarely occurring natural products; [4-(4-(methoxycarbonyl)benzyl)phenyl] carbamic acid (1), bis[di-p-phenylmethane]ethyl carbamate (2), methyl 2-hydroxy-3-(2-hydroxy-5-(3-methylbut-2-enyl)phenyl)-2-(4-hydroxyphenyl) propanoate, stocksiloate(3), along with five known compounds; 1-(4-hydroxy-3-methoxyphenyl)-1,2,3,-propanetriol (4), feruloyl-6-O-β-D-glucopyranoside (5), 4-hydroxy-3,5-dimethoxybenzoic acid (6), apocynin (7) and vincetomine (8). The structures of compounds 1 and 2 were established with help of 1D, 2D-NMR techniques and high resolution mass spectrometry, whereas, compound 3 could only be characterized tentatively by 1D, 2D-NMR techniques. Compounds 1 is new compound while 2 is synthetically known but never been reported from natural source. The known compounds were identified due to 1D NMR analysis and in comparison with the literature values. Compounds 1-3 were found inactive in an anti-urease assay.

scholarly journals Bioassay-guided isolation and identification of Aedes aegypti larvicidal and biting deterrent compounds from Veratrum lobelianum

2018 ◽  
Vol 16 (1) ◽  
pp. 324-332 ◽  
Author(s):  
Nurhayat Tabanca ◽  
Zulfiqar Ali ◽  
Ulrich R. Bernier ◽  
Nancy Epsky ◽  
Ayse Nalbantsoy ◽  
...  
Keyword(s):  
Larvicidal Activity ◽  
Ethanol Extract ◽  
Ethyl Linoleate ◽  
Significant Activity ◽  
Isolation And Identification ◽  
Human Carcinoma ◽  
Ethyl Palmitate ◽  
H Nmr ◽  
Bioassay Guided Fractionation ◽  
Nmr Techniques

AbstractAn ethanol extract fromVeratrum lobelianumBernh. rhizomes showed larvicidal activity with LC50values of 11.79 ppm and 89.9 ppm against 1stand 4thinstar larvae, respectively, at 24 h post-treatment. The extract also showed proportion not biting (PNB) value of 0.76 at 100 μg/cm2against females ofAe.aegypti. Systematic bioassay-guided fractionation ofV.lobelianumextract resulted in the isolation of five compounds that were identified as ethyl palmitate (1), ethyl linoleate (2), β-sitosterol (3), resveratrol (4) and oxyresveratrol (5) by GC-MS,1H-NMR, and13C-NMR techniques, comparison with literature data, and confirmation with authentic compounds. Compound2exhibited larvicidal activity with an LC50value of 24.1 (22.0-26.2) ppm whereas1was inactive. β-Sitosterol (3) displayed the highest larvicidal activity with LC50= 1.7 (1.3-12.3) ppm and LC90= 5.1 (3.4-13.8) ppm. Compounds4and5had larvicidal activity with LC50values of 18.5 (15.3-23.3) and 22.6 (19.0-26.8) ppm, respectively, and had an equivalent PNB values of 0.75 at 25 nmol/cm2. In addition,4and5were explored for their human-based repellency againstAe.aegypti, attractiveness against male medfliesCeratitis capitata, and also evaluated against series of human carcinoma cells (A549, HEK293, HeLa, SH-SY5Y); however, no significant activity was found.

scholarly journals New insights into Trypanosoma cruzi evolution and genotyping based on system-wide protein expression profiles (PhyloQuant)

2020 ◽  
Author(s):  
Simon Ngao Mule ◽  
Andrè Guillherme da Costa Martins ◽  
Livia Rosa-Fernandes ◽  
Gilberto Santos de Oliveira ◽  
Carla Monadeli Rodrigues ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Trypanosoma Cruzi ◽  
Protein Expression ◽  
Large Scale ◽  
Expression Profiles ◽  
Shotgun Proteomics ◽  
Close Correlation ◽  
Evolutionary Relationships ◽  
Trypanosome Species ◽  
Protein Expression Profiles

AbstractThe etiological agent of Chagas disease, Trypanosoma cruzi, is subdivided into seven genetic subdivisions termed discrete typing units (DTUs), TcI-TcVI and Tcbat. The relevance of T. cruzi genetic diversity to the variable clinical course of the disease, virulence, pathogenicity, drug resistance, transmission cycles and ecological distribution justifies the concerted efforts towards understanding the population structure of T. cruzi strains. In this study, we introduce a novel approach termed ‘phyloquant’ to infer the evolutionary relationships and assignment of T. cruzi strains to their DTUs based on differential protein expression profiles evidenced by bottom up large scale mass spectrometry-based quantitative proteomic features. Mass spectrometry features analyzed using parsimony (MS1, iBAQ and LFQ) showed a close correlation between protein expression and T. cruzi DTUs and closely related trypanosome species. Although alternative topologies with minor differences between the three MS features analyzed were demonstrated, we show congruence to well accepted evolutionary relationships of T. cruzi DTUs; in all analyses TcI and Tcbat were sister groups, and the parental nature of genotype TcII and the hybrid genotypes TcV/TcVI were corroborated. Character mapping of genetic distance matrices based on phylogenetics and phyloquant clustering showed statistically significant correlations. We propose the first quantitative shotgun proteomics approach as a complement strategy to the genetic-based assignment of T. cruzi strains to DTUs and evolutionary inferences. Moreover, this approach allows for the identification of differentially regulated and strain/DTU/species-specific proteins, with potential application in the identification of strain/DTU specific biomarkers and candidate therapeutic targets. In addition, the correlation between multi-gene protein expression and divergence of trypanosome species was evaluated, adding another level to understand the genetic subdivisions among T. cruzi DTUs.

Omphaloprenol A: A new bioactive polyisoprenepolyol isolated from the mycelium of poisonous mushroom Omphalotus japonicus

2021 ◽  
Author(s):  
Satoki Aoki ◽  
Takako Aboshi ◽  
Takumu Onodera ◽  
Ken-ichi Kimura ◽  
Daisuke Arai ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Secondary Metabolites ◽  
Bioactive Compounds ◽  
Chemical Structure ◽  
Lettuce Seeds ◽  
Illudin S ◽  
Poisonous Mushroom ◽  
Growth Promoting

Abstract Mushrooms of the Omphalotus genus are known to be rich in secondary metabolites. In the quest for new bioactive compounds, we analyzed the compounds isolated from the mycelium of the poisonous mushroom Omphalotus japonicus. As a result, a new polyisoprenepolyol, which was named omphaloprenol A, was identified, along with known substances such as hypsiziprenol A10 and A11, illudin S, and ergosterol. The chemical structure of omphaloprenol A was elucidated by nuclear magnetic resonance and infrared spectroscopies and mass spectrometry, and its bioactivity was investigated. Omphaloprenol A showed growth promoting activity against the root of lettuce seeds and cytotoxicity against HL60 cells. To the best of our knowledge, this is the first report on the isolation of a polyisoprenepolyol compound from Omphalotaceae mushrooms.

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