scholarly journals Bioactive pyrrole alkaloids isolated from the Red Sea: marine sponge Stylissa carteri

2018 ◽  
Vol 73 (5-6) ◽  
pp. 199-210 ◽  
Author(s):  
Ashraf N.E. Hamed ◽  
Roland Schmitz ◽  
Anja Bergermann ◽  
Frank Totzke ◽  
Michael Kubbutat ◽  
...  
Keyword(s):  
Protein Kinases ◽  
Red Sea ◽  
Marine Sponge ◽  
Biological Activities ◽  
2D Nmr ◽  
Moderate Activity ◽  
Aurora A ◽  
Stylissa Carteri ◽  
Pyrrole Alkaloids

Abstract Fifteen pyrrole alkaloids were isolated from the Red Sea marine sponge Stylissa carteri and investigated for their biological activities. Four of them were dibrominated [(+) dibromophakelline, Z-3-bromohymenialdisine, (±) ageliferin and 3,4-dibromo-1H-pyrrole-2-carbamide], nine compounds were monobrominated [(−) clathramide C, agelongine, (+) manzacidin A, (−) 3-bromomanzacidin D, Z-spongiacidin D, Z-hymenialdisine, 2-debromostevensine, 2-bromoaldisine and 4-bromo-1H-pyrrole-2-carbamide)] and finally, two compounds were non-brominated derivatives viz., E-debromohymenialdisine and aldisine. The structure elucidations of isolated compounds were based on 1D & 2D NMR spectroscopic and MS studies, as well as by comparison with literature. In-vitro, Z-spongiacidin D exhibited a moderate activity on (ARK5, CDK2-CycA, CDK4/CycD1, VEGF-R2, SAK and PDGFR-beta) protein kinases. Moreover, Z-3-bromohymenialdisine showed nearly similar pattern. Furthermore, Z-hymenialdisine displayed a moderate effect on (ARK5 & VEGF-R2) and (−) clathramide C showed a moderate activity on AURORA-A protein kinases. While, agelongine, (+) manzacidin A, E-debromohymenialdisine and 3,4-dibromo-1H-pyrrole-2-carbamide demonstrated only marginal inhibitory activities. The cytotoxicity study was evaluated in two different cell lines. The most effective secondary metabolites were (+) dibromophakelline and Z-3-bromohymenialdisine on L5178Y. Finally, Z-hymenialdisine, Z-3-bromohymenialdisine and (±) ageliferin exhibited the highest cytotoxic activity on HCT116. No report about inhibition of AURORA-A and B by hymenialdisine/hymenialdisine analogs existed and no reported toxicity of ageliferin existed in literature.

scholarly journals Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

Ca2+-binding proteins of cilia and infraciliary lattice ofParamecium tetraurelia: their phosphorylation by purified endogenous Ca2+-dependent protein kinases

2002 ◽  
Vol 115 (9) ◽  
pp. 1973-1984
Author(s):  
Kwanghee Kim ◽  
Min Son ◽  
Joan B. Peterson ◽  
David L. Nelson
Keyword(s):  
Protein Kinases ◽  
Calcium Binding ◽  
Binding Proteins ◽  
Soluble Fraction ◽  
Biological Activities ◽  
Anion Exchange Chromatography ◽  
Exchange Chromatography ◽  
Paramecium Tetraurelia ◽  
Dependent Protein

We purified two small, acidic calcium-binding proteins(ParameciumCa2+-binding proteins, PCBP-25α and PCBP-25β) from Paramecium tetraurelia by Ca2+-dependent chromatography on phenyl-Sepharose and by anion-exchange chromatography. The proteins were immunologically distinct. Monoclonal antibodies against PCBP-25β did not react with PCBP-25α, and antibodies against centrin from Chlamydomonas reacted with PCBP-25α but not with PCBP-25β. Like the centrins described previously, both PCBPs were associated with the infraciliary lattice (ICL), a fibrillar cytoskeletal element in Paramecium. Both were also present in isolated cilia, from which they could be released (with dynein) by a high-salt wash, and both PCBPs cosedimented with dynein in a sucrose gradient. PCBP-25β was especially prominent in cilia and in the deciliation supernatant, a soluble fraction released during the process of deciliation. The results of immunoreactivity and localization experiments suggest that PCBP-25α is a Paramecium centrin and that PCBP-25β is a distinct Ca2+-binding protein that confers Ca2+ sensitivity on some component of the cilium, ciliary basal body or ICL.We characterized these proteins and Paramecium calmodulin as substrates for two Ca2+-dependent protein kinases purified from Paramecium. PCBP-25α and calmodulin were in vitro substrates for one of the two Ca2+-dependent protein kinases (CaPK-2), but only PCBP-25α was phosphorylated by CaPK-1. These results raise the possibility that the biological activities of PCBP-25α and calmodulin are regulated by phosphorylation.

scholarly journals Identification of a Proanthocyanidin from Litchi Chinensis Sonn. Root with Anti-Tyrosinase and Antioxidant Activity

Biomolecules ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1347
Author(s):  
Matthew Saive ◽  
Manon Genva ◽  
Thibaut Istasse ◽  
Michel Frederich ◽  
Chloé Maes ◽  
...  
Keyword(s):  
Antioxidant Activities ◽  
Biological Activities ◽  
Chemical Characterization ◽  
2D Nmr ◽  
Ethnobotanical Study ◽  
Traditional Use ◽  
Litchi Chinensis ◽  
Isolated Compound ◽  
First Time

This work follows an ethnobotanical study that took place in the island of Mayotte (France), which pointed out the potential properties of Litchi chinensis Sonn. roots when used to enhance skin health and appearance. Through in vitro testing of a crude methanolic extract, high anti-tyrosinase (skin whitening effect) and antioxidant activities (skin soothing effect) could be measured. HPLC successive bio-guided fractionation steps allowed the purification of one of the compounds responsible for the biological activities. The isolated compound was characterized by UV, IR, MS and 2D-NMR, revealing, for the first time in Litchi chinensis Sonn. roots, an A-type proanthocyanidin and thus revealing a consensus among the traditional use shown by the ethnobotanical study, in vitro biological activities and chemical characterization.

scholarly journals New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 100
Author(s):  
Sherif Ebada ◽  
Werner Müller ◽  
Wenhan Lin ◽  
Peter Proksch
Keyword(s):  
Spectral Analysis ◽  
Marine Sponge ◽  
Parent Compound ◽  
2D Nmr ◽  
Chemical Structures ◽  
Nmr Data ◽  
Ic50 Values ◽  
Nanomolar Range ◽  
Mouse Lymphoma

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

scholarly journals Sugar Containing Compounds and Biological Activities of Lagochilus setulosus

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1755
Author(s):  
Davlat Kh. Akramov ◽  
Nilufar Z. Mamadalieva ◽  
Andrea Porzel ◽  
Hidayat Hussain ◽  
Mthandazo Dube ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
Biological Activities ◽  
2D Nmr ◽  
Septoria Tritici ◽  
2D Nmr Spectroscopy ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
Phytochemical Investigation ◽  
Diphenyl Tetrazolium Bromide

Phytochemical investigation of the methanolic extract obtained from the aerial parts of Lagochilus setulosus (Lamiaceae) afforded the new compound 1-methoxy-3-O-β-glucopyranosyl-α-l-oliose (1) together with five known glycosides, namely sitosterol-3-O-β-glucoside (2), stigmasterol-3-O-β-glucoside (3), pinitol (4), 6β-hydroxyl-7-epi-loganin (5), and chlorotuberoside (6). The structures of these compounds were elucidated by extensive spectroscopic analyses, especially HR-MS, 1D and 2D NMR spectroscopy. The in vitro cytotoxic activity of the methanolic extract and the isolated compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and crystal violet (CV) staining assays. In addition, the antifungal activities of the components were evaluated against Botrytis cinerea, Septoria tritici, and Phytophthora infestans. The anthelmintic potential was determined against Caenorhabditis elegans nematodes. Neither the extract nor the isolated compounds showed promising activity in all the bioassays.

Synthesis and Cytotoxic Evaluation of Novel Benzimidazole Fused Condensed Thienopyrimdines Derivatives

2020 ◽  
Vol 16 (2) ◽  
pp. 133-141
Author(s):  
S. Kaliraj ◽  
Muthu K. Kathiravan
Keyword(s):  
Good Yield ◽  
Biological Activities ◽  
In Vitro Cytotoxicity ◽  
Cytotoxic Action ◽  
Moderate Activity ◽  
Quinazoline Derivative ◽  
Cellular Division ◽  
Major Health Problem ◽  
Cytotoxicity Studies

Background: Cancer is a major health problem acting as a global killer and one of the leading causes of death. Most cancer chemotherapeutic drugs currently in clinical use are to kill malignant tumour cells by inhibiting some of the mechanisms implied in cellular division. Thienopyrimidines occupy a special position among the fused pyrimidines, along with other pyrimidines containing an annelated five membered hetero aromatic ring; forms a significant class of drugs which exhibit an array of various biological activities. One of the important current anticancer agent gefitinib acts as tyrosine kinase inhibitors is a quinazoline derivative. The thieno[2,3-d]pyrimidine ring system, is considered as a bioisostere of quinazoline moiety and have attracted great attention due to their broad bioactivities, including antitumor. Methods: Novel thienopyrimidine derivatives were synthesized by cyclization of thiophene o-amino esters with lactam salts such as pyrrolidin-2-one, piperidin-2-one and caprolactam by treating using phosphorous oxychloride. The next set of compounds thieno[2,3-d]pyrimidin-4(3H)-one were synthesised by Niementowski condensations between 2-aminothiophene carboxylate and formamide under reflux condition, followed by its chlorination in good yield. Microwave Fusion of 4-chlorothieno[2,3-d] pyrimidines with o-phenylenediamine afforded target compounds. The target compounds were tested on MCF-7 and HEK293 cell line. Results: The synthesized thirty compounds structures were established by IR, 1H NMR and Mass spectroscopy. The synthesized compounds were obtained in the good yield ranging from 45-70%. The synthesized compounds were subjected to cytotoxicity studies. Among the twenty compounds only one compound showed moderate activity. One of the compound 2c bearing acetyl group had IC50 48.93 μM. However decrease in the size of the lactam ring from six to five member ring or increase to seven member ring resulted in the loss of activity. The IC50 value of 5a was found to be 70.86μg/ml. The compound 5i have more cytotoxic action among the series. Conclusion: A series of thirty compounds belonging to novel pyyrolo, pyrido and benzimidazole fused thienopyrimidines were synthesized, characterized and were evaluated for their in vitro cytotoxicity. The compounds bearing bulky group such as terbutyl group and chloro substitution had the best activity. In conclusion, these structures seems to have biological properties and further investigation on this group could provide a lead.

scholarly journals Antioxidant, Antiproliferative and Antimicrobial Activities of the Volatile Oil from the Wild Pepper Piper capense Used in Cameroon as a Culinary Spice

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Verlaine Woguem ◽  
Filippo Maggi ◽  
Hervet P. D. Fogang ◽  
Léon A. Tapondjou ◽  
Hilaire M. Womeni ◽  
...  
Keyword(s):  
Essential Oil ◽  
Tumor Cells ◽  
Biological Activities ◽  
Human Tumor ◽  
Breast Adenocarcinoma ◽  
Moderate Activity ◽  
Oil Composition ◽  
Human Tumor Cells ◽  
Agar Disc

Wild pepper (Piper capense L.f., Piperaceae) is a spice traditionally used in western Cameroon to make soups called ‘ Nkui’ and ‘ Nah poh’. In the present work, the essential oil hydrodistilled from fruits was analyzed by GC-FID and GC-MS, and for in vitro biological activities, namely cytotoxic, antioxidant and antimicrobial, by MTT, DPPH, ABTS and agar disc diffusion methods. The oil composition was dominated by monoterpene hydrocarbons (56.5%) responsible for the pepper odor, such as β-pinene (33.2%), sabinene (10.0%) and α-pinene (8.9%). The oil induced a concentration-dependent inhibitory effect on human tumor cells MDA-MB 231 (breast adenocarcinoma), A375 (malignant melanoma) and HCT116 (colon carcinoma), showing IC50 values of 26.3, 76.0 and 22.7 μg/ml, respectively. The oil showed total antioxidant activity with a Trolox equivalent antioxidant concentration (TEAC) value of 140 μmol/g. The essential oil of P. capense proved to be an effective scavenger of the ABTS+ radical, with an activity only about 30 times lower than that of Trolox. Moderate activity was observed against the Gram-positive species Staphylococcos aureus and Enterococcus faecalis, and the yeast Candida albicans. The notable inhibition of some human tumor cells is worthy of further investigation to discover the possible mechanisms of action responsible for the observed cytotoxic effect of this essential oil.

scholarly journals New Antiproliferative Cembrane Diterpenes from the Red Sea Sarcophyton Species

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 411 ◽  
Author(s):  
Hossam M. Hassan ◽  
Mostafa E. Rateb ◽  
Marwa H. Hassan ◽  
Ahmed M. Sayed ◽  
Samah Shabana ◽  
...  
Keyword(s):  
Red Sea ◽  
Antiproliferative Activity ◽  
High Resolution Mass Spectrometry ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Future Design ◽  
Chemical Structures ◽  
New Compounds ◽  
Mcf 7

The combination of liquid chromatography coupled to high resolution mass spectrometry (LC-HRESMS)-based dereplication and antiproliferative activity-guided fractionation was applied on the Red Sea-derived soft coral Sarcophyton sp. This approach facilitated the isolation of five new cembrane-type diterpenoids (1–5), along with two known analogs (6 and 7), as well as the identification of 19 further, known compounds. The chemical structures of the new compounds were elucidated while using comprehensive spectroscopic analyses, including one-dimensional (1D) and two-dimensional (2D) NMR and HRMS. All of the isolated cembranoids (1–7) showed moderate in vitro antiproliferative activity against a human breast cancer cell line (MCF-7), with IC50 ranging from 22.39–27.12 µg/mL. This class of compounds could thus serve as scaffold for the future design of anticancer leads.

scholarly journals Two New Naphthoquinone Derivatives from the Stem Bark of Callicarpa Maingayi

2012 ◽  
Vol 7 (10) ◽  
pp. 1934578X1200701
Author(s):  
Sumayah Mohammed Asiri ◽  
Khozirah Shaari ◽  
Faridah Abas ◽  
Nabil Ali Al-Mekhlafi ◽  
Nordin H. Lajis
Keyword(s):  
Cytotoxic Activity ◽  
Human Breast Cancer ◽  
2D Nmr ◽  
Stem Bark ◽  
Chloroform Fraction ◽  
Moderate Activity ◽  
Human Breast ◽  
Spectroscopic Analyses ◽  
First Time

Two new naphthoquinones designated as 3α-hydroxy-2-(2-hydroxypropan-2-yl)-9α-methoxy-2,3,3α,9α-tetra-hydronaphtho[2,3-b]furan-4,9-dione (callicarpa-quinone A, 1) and 5-hydroxy-2-(2-hydroxypropan-2-yl)naphtho[2,3-b]furan-4,9-dione (callicarpaquinone B, 2) were isolated from the chloroform fraction of Callicarpa maingayi. Three other known compounds, identified as avicequinone-C (3), wodeshiol (4) and paulownin (5), were reported for the first time from this species. The structure elucidation of compounds was established by comprehensive 1D and 2D NMR spectroscopic analyses as well as EIMS, UV and IR spectral data. Compounds 1 and 2 were tested in vitro for their cytotoxic activity against human breast cancer MCF-7cells. Compound 2 exhibited strong cytotoxic activity with an IC50 value of 1.9 ± 0.2 μM, while 1 showed moderate activity with an IC50 value of 25.0 ± 4.3 μM.

Four new triterpenoids from Chisocheton paniculatus and their anti-inflammatory activities

2012 ◽  
Vol 90 (2) ◽  
pp. 199-204 ◽  
Author(s):  
Ming-Hua Yang ◽  
Jun-Song Wang ◽  
Jian-Guang Luo ◽  
Xiao-Bing Wang ◽  
Ling-Yi Kong
Keyword(s):  
Spectroscopic Data ◽  
In Vitro Model ◽  
2D Nmr ◽  
No Production ◽  
Moderate Activity ◽  
Inhibitory Effects ◽  
Raw264.7 Macrophages ◽  
Anti Inflammatory ◽  
Vitro Model

As part of our continuing effort to discover new potential anti-inflammatory agents, four new triterpenoids, chisopanins L-O (1–4), were isolated from the twigs of Chisocheton paniculatus. Their structures were established on the basis of detailed analysis of spectroscopic data, including IR, NMR (1D and 2D NMR), and HR-ESI-MS. Their inhibitory effects against nitric oxide (NO) production were evaluated in an in vitro model of lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Compounds 1, 3, and 4 were found to exhibit moderate activity with IC50 values less than 10 μmol/L.

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