scholarly journals Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6379
Author(s):  
Aleksandra Dymek ◽  
Jarosław Widelski ◽  
Krzysztof Kamil Wojtanowski ◽  
Vladyslav Vivcharenko ◽  
Agata Przekora ◽  
...  

In view of the abundant evidence that Lycopodiaceae alkaloids, including the well-known huperzine A (HupA), are among the potent acetylcholinesterase (AChE) inhibitors, an attempt was made to search for new compounds responsible for this property. For this purpose, three plant species belonging to the Lycopodiaceae family, commonly found in the Euro-Asia region, were subjected to the isolation of bioactive compounds, their identification and subsequent evaluation of their anticholinesterase and cytotoxic activities. Methanolic extracts of two Lycopodium and one Hupezia species were obtained via optimized pressurized liquid extraction (PLE) and then pre-purified using innovative gradient vacuum liquid chromatography (gVLC). For the first time, three sorbents of different porosity packed in polypropylene cartridges and mobile phase systems of different polarity were used to elute the target compounds. This technique proved to be a rapid tool for the obtainment of alkaloid fractions and allowed one to select the appropriate process conditions to yield potent AChE inhibitors in each of the species studied. More than 100 collected fractions were analyzed via HPLC/ESI-QTOF-MS, which enabled one to detect more than 50 compounds, including several new ones previously unreported. Some of them were present in high purity fractions (60–90% of the established purity). TLC bioautography assays proved that the analyzed species are rich sources of AChE inhibitors, but H. selago showed the highest anti-AChE activity. Additionally, the modified silanized silica gel sorbent used allowed one to isolate L. clavatum alkaloids more efficiently using an aqueous reversed-phase solvent system. Furthermore, the tested extracts from the three plant extracts were found to be safe, as they did not exhibit cytotoxicity to skin fibroblasts.

2004 ◽  
Vol 70 (6) ◽  
pp. 3521-3527 ◽  
Author(s):  
Min Ye ◽  
Guiqin Qu ◽  
Hongzhu Guo ◽  
Dean Guo

ABSTRACT Biotransformation of natural products has great potential for producing new drugs and could provide in vitro models of mammalian metabolism. Microbial transformation of the cytotoxic steroid cinobufagin was investigated. Cinobufagin could be specifically hydroxylated at the 12β-position by the fungus Alternaria alternata. Six products from a scaled-up fermentation were obtained by silica gel column chromatography and reversed-phase liquid chromatography and were identified as 12β-hydroxyl cinobufagin, 12β-hydroxyl desacetylcinobufagin, 3-oxo-12β-hydroxyl cinobufagin, 3-oxo-12β-hydroxyl desacetylcinobufagin, 12-oxo-cinobufagin, and 3-oxo-12α-hydroxyl cinobufagin. The last five products are new compounds. 12β-Hydroxylation of cinobufagin by A. alternata is a fast catalytic reaction and was complete within 8 h of growth with the substrate. This reaction was followed by dehydrogenation of the 3-hydroxyl group and then deacetylation at C-16. Hydroxylation at C-12β also was the first step in the metabolism of cinobufagin by a variety of fungal strains. In vitro cytotoxicity assays suggest that 12β-hydroxyl cinobufagin and 3-oxo-12α-hydroxyl cinobufagin exhibit somewhat decreased but still significant cytotoxic activities. The 12β-hydroxylated bufadienolides produced by microbial transformation are difficult to obtain by chemical synthesis.


2008 ◽  
Vol 73 (12) ◽  
pp. 1161-1167 ◽  
Author(s):  
Nebojsa Jockovic ◽  
Paula Andrade ◽  
Patrícia Valentão ◽  
Marko Sabovljevic

The chemistry of bryophytes is not well known. The available data indicate interesting chemical constitutions of some bryophyte species, i.e., active and new compounds are to be found within bryophytes, especially liverworts. In this study, one liverwort and two moss species were studied: Lunularia cruciata (L.) Dumort, Brachytheciastrum velutinum (Hedw) Ignatov & Huttunen and Kindbergia praelonga (Hedw) Ochyra. The phenolic compositions of these bryophyte species have not hitherto been reported. Their methanolic extracts were analyzed by reversed-phase HPLC, coupled to a diode-array detector (DAD). Luteolin-7-O-glucoside and quercetin were found in the L. cruciata extract. The extract obtained from B. velutinum contained four phenolic acids (4-O-caffeoylquinic, 5-O-caffeoylquinic, caffeic and ellagic acids) and three flavonoids (apigenin-7-O-glucoside, luteolin and apigenin). The K. praelonga extract was characterized by the presence of several phenolic acids and their derivatives (4-O-caffeoylquinic, 5-O-caffeoylquinic, caffeic, p-coumaric, ferulic and ellagic acids, and caffeic and p-coumaric acid derivatives) and three flavonoids (apigenin-7-O-glucoside, luteolin, apigenin and an unidentified flavanone). .


Author(s):  
Aleksandra Dymek ◽  
Tomasz Mroczek

Abstract Alkaloids obtained from plants belonging to the Amaryllidaceae and Lycopodiaceae families are of great interest due to their numerous properties. They play a very important role mainly due to their strong antioxidant, anxiolytic and anticholinesterase activities. The bioactive compounds obtained from these two families, especially galanthamine and huperzine A, have found application in the treatment of the common and incurable dementia-like Alzheimer’s disease. Thanks to this discovery, there has been a breakthrough in its treatment by significantly improving the patient’s quality of life and slowing down disease symptoms – albeit with no chance of a complete cure. Therefore, a continuous search for new compounds with potent anti-AChE activity is needed in modern medicine. In obtaining new therapeutic bioactive phytochemicals from plant material, the isolation process and its efficiency are crucial. Many techniques are known for isolating bioactive compounds and determining their amounts in complex samples. The most commonly utilized methods are extraction using different variants of organic solvents allied with chromatographic and spectrometric techniques. Optimization of these methods and modification of their procedures potentially allows researchers to obtain the expected results. The aim of this paper is to present known techniques for the isolation of alkaloids, especially from three species Narcissus, Lycopodium and Huperzia that are a rich source of AChE inhibitors. In addition, innovative combinations of chromatographic and spectrometric methods and novel TLC-bioautography will be presented to enable researchers to better study the bioactivity of alkaloids.


Fitoterapia ◽  
2021 ◽  
Vol 151 ◽  
pp. 104883
Author(s):  
Jiaqian Chen ◽  
Chen Jin ◽  
Bolun Xu ◽  
Jicheng Shu ◽  
Feng Shao ◽  
...  

2021 ◽  
Vol 11 (13) ◽  
pp. 6008
Author(s):  
Micael F. M. Gonçalves ◽  
Ana Paço ◽  
Luís F. Escada ◽  
Manuela S. F. Albuquerque ◽  
Carlos A. Pinto ◽  
...  

There is an urgent need for new substances to overcome current challenges in the health sciences. Marine fungi are known producers of numerous compounds, but the manipulation of growth conditions for optimal compound production can be laborious and time-consuming. In Portugal, despite its very long coastline, there are only a few studies on marine fungi. From a collection of Portuguese marine fungi, we screened for antimicrobial, antioxidant, enzymatic, and cytotoxic activities. Mycelia aqueous extracts, obtained by high pressure-assisted extraction, and methanolic extracts of culture media showed high antioxidant, antimicrobial, and cytotoxic activities. The mycelium extracts of Cladosporium rubrum showed higher antioxidant potential compared to extracts from other fungi. Mycelia and culture media extracts of Aspergillus affinis and Penicillium lusitanum inhibited the growth of Staphylococcus aureus, Kocuria rhizophila, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa, including multiresistant strains. Penicillium lusitanum and Trichoderma aestuarinum inhibited the growth of clinical strains of Candida albicans, C. glabrata, C. parapsilosis, and C. tropicalis. All extracts from culture media were cytotoxic to Vero cells. Sea salt induced alterations in the mycelium’s chemical composition, leading to different activity profiles.


2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.


2017 ◽  
Vol 72 (3) ◽  
pp. 175-182 ◽  
Author(s):  
Humaira Naureen ◽  
Michel Feussi Tala ◽  
Khaled A. Shaaban ◽  
Mohamed Shaaban ◽  
Anja Schüffler ◽  
...  

Abstract Three new bioactive metabolites, 1,6-dihydroxy- 2-methyl-heptan-4-one (1), 4-hydroxy-1-(2-methyl-oxiranyl)- pentan-2-one (2), and 2-(2-hydroxy-propyl)-4-methylfuran- 3-carboxylic acid amide (3) were isolated from the terrestrial Streptomyces sp. isolate ANK245, along with the new microbial constituent p-vinylanisol (4a) and the known metabolites p-vinyl-phenol (4b) and phenethyl alcohol. Analysis of the nonpolar part of the extract by gas chromatography/mass spectrometry (GC-MS) provided further evidence for tetradecanoic acid, 9-octadecenoic acid, hexadecanoic acid, 2-methoxy-4-vinylphenol (4c), 4-hydroxy-3-methoxy-benzaldehyde, o-hydroxybiphenyl, and 1,5,9-trimethyl-4,8,13-cyclotetradecatrien-1,3-diol (5). Structures 1–3 of the new compounds were elucidated by nuclear magnetic resonance (NMR) and NMR spectroscopy, but mass spectrometry (MS) techniques and their absolute configuration were determined by density functional theory (DFT) calculations and Mosher derivatisation. Their antimicrobial and cytotoxic activities were evaluated in comparison with the crude bacterial extract.


2021 ◽  
Vol 45 (2) ◽  
pp. 203-213
Author(s):  
Mariana Oaldje-Pavlovic ◽  
Ana Alimpic-Aradski ◽  
Aleksandra Savic ◽  
Smiljana Jankovic ◽  
Milena Milutinovic ◽  
...  

This study was aimed at evaluating the antioxidant and antidiabetic activities of methanolic extracts of peel, flesh and mixed peel, and flesh, as well as the cytotoxic activity of mixed peel and flesh extracts obtained from fruits of six traditional pear varieties (Vidovaca, Lubenicarka, Karamanka, Jeribasma, Loncara and Takisa), one commercial variety (Williams Bartlett) and a wild pear (Pyrus communis) from Serbia. The tested extracts showed strong antioxidant activity regarding the prevention of ?-carotene bleaching and high ?-glucosidase inhibition, and no significant cytotoxic potential, with the exception of the Williams Bartlett and Pyrus communis extracts. Overall, the most potent fruit part was shown to be the peel. The most active variety in all of the applied antioxidant and antidiabetic assays was Takisa, while the wild pear, P. communis, was the most effective in inhibiting the proliferation of cancer cells. In conclusion, several methanolic extracts of pear fruit are promising candidates for further studies regarding the prevention and treatment of pathological conditions associated with the effects of oxidative stress, such as diabetes and even colorectal cancer.


2021 ◽  
Vol 12 ◽  
Author(s):  
Ting Shi ◽  
Xiang-Qian Li ◽  
Li Zheng ◽  
Ya-Hui Zhang ◽  
Jia-Jia Dai ◽  
...  

The fungal strains Pseudogymnoascus are a kind of psychrophilic pathogenic fungi that are ubiquitously distributed in Antarctica, while the studies of their secondary metabolites are infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11 led to the isolation of six new tremulane sesquiterpenoids pseudotremulanes A–F (1–6), combined with one known analog 11,12-epoxy-12β-hydroxy-1-tremulen-5-one (7), and five known steroids (8–12). The absolute configurations of the new compounds (1–6) were elucidated by their ECD spectra and ECD calculations. Compounds 1–7 were proved to be isomeride structures with the same chemical formula. Compounds 1/2, 3/4, 1/4, and 2/3 were identified as four pairs of epimerides at the locations of C-3, C-3, C-9, and C-9, respectively. Compounds 8 and 9 exhibited cytotoxic activities against human breast cancer (MDA-MB-231), colorectal cancer (HCT116), and hepatoma (HepG2) cell lines. Compounds 9 and 10 also showed antibacterial activities against marine fouling bacteria Aeromonas salmonicida. This is the first time to find terpenoids and steroids in the fungal genus Pseudogymnoascus.


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