Eucomic acid

In Vitro Antiplasmodial and Cytotoxic Activities of Compounds from the Roots of Eriosema montanum Baker f. (Fabaceae).[Pubmed:34068519]

Molecules. 2021 May 10;26(9). pii: molecules26092795.

Malaria remains one of the leading causes of death in sub-Saharan Africa, ranked in the top three infectious diseases in the world. Plants of the Eriosema genus have been reported to be used for the treatment of this disease, but scientific evidence is still missing for some of them. In the present study, the in vitro antiplasmodial activity of the crude extract and compounds from Eriosema montanum Baker f. roots were tested against the 3D7 strain of Plasmodium falciparum and revealed using the SYBR Green, a DNA intercalating compound. The cytotoxicity effect of the compounds on a human cancer cell line (THP-1) was assessed to determine their selectivity index. It was found that the crude extract of the plant displayed a significant antiplasmodial activity with an IC50 (microg/mL) = 17.68 +/- 4.030 and a cytotoxic activity with a CC50 (microg/mL) = 101.5 +/- 12.6, corresponding to a selective antiplasmodial activity of 5.7. Bioactivity-guided isolation of the major compounds of the roots' crude extract afforded seven compounds, including genistein, genistin and Eucomic acid. Under our experimental conditions, using Artemisinin as a positive control, Eucomic acid showed the best inhibitory activity against the P. falciparum 3D7, a well-known chloroquine-sensitive strain. The present results provide a referential basis to support the traditional use of Eriosema species in the treatment of malaria.

Emergent Technologies for the Extraction of Antioxidants from Prickly Pear Peel and Their Antimicrobial Activity.[Pubmed:33803279]

Foods. 2021 Mar 9;10(3). pii: foods10030570.

Phenolic compounds are important bioactive compounds identified in prickly pear peel that have important antioxidant and antimicrobial properties. However, conventional thermal extraction methods may reduce their bioactivity, and technologies such as high pressure (HP) and ohmic heating (OH) may help preserve them. In this study, both technologies were analyzed, individually and combined (250/500 MPa; 40/70 degrees C; ethanol concentration 30/70%), and compared with Soxhlet with regard to total phenolics, flavonoids, and carotenoids as well as antioxidant (ABTS, DPPH, ORAC), DNA pro-oxidant, and antimicrobial (inhibition halos, minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), growth curves, and viable cells) activities of prickly pear peel extracts. Total phenolics extracted by each technology increased 103% (OH) and 98% (HP) with regard to Soxhlet, but the contents of total flavonoids and carotenoids were similar. Antioxidant activity increased with HP and OH (between 35% and 63%), and OH (70 degrees C) did not induce DNA degradation. The phenolic compound present in higher amounts was piscidic acid, followed by Eucomic acid and citrate. In general, their extraction was significantly favored by HP and OH. Antimicrobial activity against 7 types of bacteria showed effective results only against S. aureus, S. enteritidis, and B. cereus. No synergetic or additive effect was observed for HP/OH.

Potential of Smoke-Water and One of Its Active Compounds (karrikinolide, KAR1) on the Phytochemical and Antioxidant Activity of Eucomis autumnalis.[Pubmed:31816895]

Antioxidants (Basel). 2019 Dec 3;8(12). pii: antiox8120611.

Eucomis autumnalis (Mill.) Chitt. subspecies autumnalis is a popular African plant that is susceptible to population decline because the bulbs are widely utilized for diverse medicinal purposes. As a result, approaches to ensure the sustainability of the plants are essential. In the current study, the influence of smoke-water (SW) and karrikinolide (KAR1 isolated from SW extract) on the phytochemicals and antioxidant activity of in vitro and greenhouse-acclimatized Eucomis autumnalis subspecies autumnalis were evaluated. Leaf explants were cultured on Murashige and Skoog (MS) media supplemented with SW (1:500, 1:1000 and 1:1500 v/v dilutions) or KAR1 (10(-7), 10(-8) and 10(-9) M) and grown for ten weeks. In vitro regenerants were subsequently acclimatized in the greenhouse for four months. Bioactive phytochemicals in different treatments were analyzed using ultra-high performance liquid chromatography (UHPLC-MS/MS), while antioxidant potential was evaluated using two chemical tests namely: DPPH and the beta-carotene model. Smoke-water and KAR1 generally influenced the quantity and types of phytochemicals in in vitro regenerants and acclimatized plants. In addition to Eucomic acid, 15 phenolic acids and flavonoids were quantified; however, some were specific to either the in vitro regenerants or greenhouse-acclimatized plants. The majority of the phenolic acids and flavonoids were generally higher in in vitro regenerants than in acclimatized plants. Evidence from the chemical tests indicated an increase in antioxidant activity of SW and KAR1-treated regenerants and acclimatized plants. Overall, these findings unravel the value of SW and KAR1 as potential elicitors for bioactive phytochemicals with therapeutic activity in plants facilitated via in vitro culture systems. In addition, it affords an efficient means to ensure the sustainability of the investigated plant. Nevertheless, further studies focusing on the use of other types of antioxidant test systems (including in vivo model) and the carry-over effect of the application of SW and KAR1 for a longer duration will be pertinent. In addition, the safety of the resultant plant extracts and their pharmacological efficacy in clinical relevance systems is required.

Comparative metabolite fingerprinting of legumes using LC-MS-based untargeted metabolomics.[Pubmed:31732019]

Food Res Int. 2019 Dec;126:108666.

Legumes are a well-known source of phytochemicals and are commonly believed to have similar composition between different genera. To date, there are no studies evaluating changes in legumes to discover those compounds that help to discriminate for food quality and authenticity. The aim of this work was to characterize and make a comparative analysis of the composition of bioactive compounds between Cicer arietinum L. (chickpea), Lens culinaris L. (lentil) and Phaseolus vulgaris L. (white bean) through an LC-MS-Orbitrap metabolomic approach to establish which compounds discriminate between the three studied legumes. Untargeted metabolomic analysis was carried out by LC-MS-Orbitrap from extracts of freeze-dried legumes prepared from pre-cooked canned legumes. The metabolomic data treatment and statistical analysis were realized by using MAIT R's package, and final identification and characterization was done using MS(n) experiments. Fold-change evaluation was made through Metaboanalyst 4.0. Results showed 43 identified and characterized compounds displaying differences between the three legumes. Polyphenols, mainly flavonol and flavanol compounds, were the main group with 30 identified compounds, followed by alpha-galactosides (n=5). Fatty acyls, prenol lipids, a nucleoside and organic compounds were also characterized. The fold-change analysis showed flavanols as the wider class of discriminative compounds of lentils compared to the other legumes; prenol lipids and Eucomic acids were the most discriminative compounds of beans versus other legumes and several phenolic acids (such as primeveroside salycilic), kaempferol derivatives, coumesterol and alpha-galactosides were the most discriminative compounds of chickpeas. This study highlights the applicability of metabolomics for evaluating which are the characteristic compounds of the different legumes. In addition, it describes the future application of metabolomics as tool for the quality control of foods and authentication of different kinds of legumes.

Antimicrobial and Antibiofilm Activity against Staphylococcus aureus of Opuntia ficus-indica (L.) Mill. Cladode Polyphenolic Extracts.[Pubmed:31052535]

Antioxidants (Basel). 2019 May 2;8(5). pii: antiox8050117.

Plant extracts are a rich source of natural compounds with antimicrobial properties, which are able to prevent, at some extent, the growth of foodborne pathogens. The aim of this study was to investigate the potential of polyphenolic extracts from cladodes of Opuntia ficus-indica (L.) Mill. to inhibit the growth of some enterobacteria and the biofilm formation by Staphylococcus aureus. Opuntia ficus-indica cladodes at two stages of development were analysed for total phenolic content and antioxidant activity by Oxygen Radical Absorbance Capacity (ORAC) and Trolox equivalent antioxidant capacity (TEAC) (in vitro assays) and by cellular antioxidant activity in red blood cells (CAA-RBC) (ex vivo assay). The Liquid Chromatography Time-of-Flight Mass Spectrometry (LC/MS-TOF) analysis of the polyphenolic extracts revealed high levels of piscidic acid, Eucomic acid, isorhamnetin derivatives and rutin, particularly in the immature cladode extracts. Opuntia cladodes extracts showed a remarkable antioxidant activity (in vitro and ex vivo), a selective inhibition of the growth of Gram-positive bacteria, and an inhibition of Staphylococcus aureus biofilm formation. Our results suggest and confirm that Opuntia ficus-indica cladode extracts could be employed as functional food, due to the high polyphenolic content and antioxidant capacity, and used as natural additive for food process control and food safety.

Digestion and Colonic Fermentation of Raw and Cooked Opuntia ficus-indica Cladodes Impacts Bioaccessibility and Bioactivity.[Pubmed:30757900]

J Agric Food Chem. 2019 Mar 6;67(9):2490-2499.

The bioactivity of (poly)phenols from a food is an interplay between the cooking methods applied and the interaction of the food with the gastrointestinal tract. The (poly)phenolic profile and biological activity of raw and cooked cactus ( Opuntia ficus-indica Mill.) cladodes following in vitro digestion and colonic fermentation were evaluated. Twenty-seven (poly)phenols were identified and quantified by HPLC-ESI-MS, with piscidic acid being the most abundant. Throughout the colonic fermentation, flavonoids showed more degradation than phenolic acids, and Eucomic acid remained the most relevant after 24 h. The catabolite 3-(4-hydroxyphenyl)propionic acid was generated after 24 h of fermentation. Cytotoxicity, genotoxicity, and cell cycle analyses were performed in HT29 cells. Cactus colonic fermentates showed higher cell viability (>/=80%) in comparison to the control fermentation with no cactus and significantly ( p < 0.05) reduced H2O2-induced DNA damage in HT29 cells. Results suggest that, although phenolic compounds were degraded during the colonic fermentation, the biological activity is retained in colon cells.

Genus Vanda: A review on traditional uses, bioactive chemical constituents and pharmacological activities.[Pubmed:30268653]

J Ethnopharmacol. 2019 Jan 30;229:46-53.

ETHNOPHARMACOLOGICAL RELEVANCE: The genus Vanda (Family: Orchidaceae) comprises about 73 species mainly distributed in Southeast Asia. Plants belonging to this genus are being used in the traditional medicine systems in Asian countries specially in India, Nepal, China and Bangladesh. AIM OF THE REVIEW: The aim of this work was to review the scientific work about medicinal orchids of the genus Vanda regarding their traditional uses, reported bioactive components, and pharmacological activities. MATERIALS AND METHODS: The information related to traditional uses, pharmacological activities, and bioactive compounds was systematically collected from the scientific literature databases including SciFinder, Scopus, PubMed and Google Scholar, published books and conference proceedings. RESULTS: The literature survey revealed diverse traditional uses of different species of Vanda, mainly against indigestion, wounds, hepatitis, dyspepsia, bronchitis, piles, rheumatism, and bone fracture. However, only few of them are investigated scientifically for their chemical constituents and pharmacological activities. Bioactive compounds including Eucomic acid derivatives, phenanthrene derivatives and other phenolic compounds are reported from Vanda species. Different extracts were so far evaluated for number of pharmacological activities including neuroprotective, anti-aging, antimicrobial, anti-inflammatory, antioxidant, membrane stabilizing, wound healing and hepato-protective activities. CONCLUSION: Vanda spp. are of much significance as ornamental flowers, but also used widely in traditional medicines and have potential for their diverse pharmacological activities. However, many members of the genus Vanda need further detailed studies regarding chemical constituents and mechanism-based pharmacological activities. Similarly, further studies should also focus on the conservation, cultivation and sustainable utilization of these species.

Digestibility of (Poly)phenols and Antioxidant Activity in Raw and Cooked Cactus Cladodes ( Opuntia ficus-indica).[Pubmed:29770691]

J Agric Food Chem. 2018 Jun 13;66(23):5832-5844.

This study aims to investigate whether heat treatment applied to cactus cladodes influences the bioaccessibility of their (poly)phenolic compounds after simulated gastric and intestinal digestion. A total of 45 (poly)phenols were identified and quantified in raw and cooked cactus cladodes by ultra high performance liquid chromatography photodiode array detector high resolution mass spectrometry. Both flavonoids (60-68% total), mainly isorhamnetin derivatives, and phenolic acids (32-40%) with Eucomic acids as the predominant ones significantly ( p < 0.05) increased with microwaving and griddling processes. After in vitro gastrointestinal digestion, 55-64% of the total (poly)phenols of cooked cactus cladodes remained bioaccessible versus 44% in raw samples. Furthermore, digestive conditions and enzymes degraded or retained more flavonoids (37-63% bioaccessibility) than phenolic acids (56-87% bioaccessibility). Microwaved cactus cladodes contributed the highest amount of (poy)phenols (143.54 mg/g dm) after gastrointestinal process, followed by griddled samples (133.98 mg/g dm), showing the highest antioxidant capacity. Additionally, gastrointestinal digestion induced isomerizations among the three stereoisomeric forms of piscidic and Eucomic acids.

Crispoic acid, a new compound from Laelia marginata (Orchidaceae), and biological evaluations against parasites, human cancer cell lines and Zika virus.[Pubmed:29117727]

Nat Prod Res. 2018 Dec;32(24):2916-2921.

The phytochemical study of Laelia marginata (Lindl.) L. O. Williams (Orchidaceae) led to the isolation of a new natural product named crispoic acid (1), together with six other known compounds (2-7). The new natural product was identified as a dimer of Eucomic acid and was structurally characterised based upon 1D and 2D NMR and HRMS data. Biological assays with plant crude extract, fractions and isolated compounds were performed against two human cancer cell lines (Hela and Siha), and the tropical parasites Trypanosoma cruzi and Leishmania (Leishmania) amazonensis. The phenantrenoid 9,10-dihydro-4-methoxyphenanthren-2,7-diol 2 was active against Hela and Siha cells (CC50 5.86 +/- 0.19 and 20.78 +/- 2.72 mug/mL, respectively). Sub-lethal concentrations of the flavone rhamnazin 4 were not able to rescue the viability of the Vero cells infected by Zika virus.

Phenolic compounds from Bletilla striata.[Pubmed:28276764]

J Asian Nat Prod Res. 2017 Oct;19(10):981-986.

Two new malic acid derivatives, namely Eucomic acid 1-methyl ester (2) and 6'''-acetylmilitaline (7), together with ten known compounds (1, 3-6, 8-12), were isolated from the dry tubers of Bletilla striata (Thunb.) Reichb. F., a perennial traditional Chinese medicinal herb, which was used for the treatment of pneumonophthisis, pneumonorrhagia, tuberculosis, and hemorrhage of the stomach or lung. Their structures were elucidated by spectroscopic analyses, including 1D-, 2D-NMR, and HR-ESI-MS.

Phytochemical Characterization, Antibacterial, Acetylcholinesterase Inhibitory and Cytotoxic Properties of Cryptostephanus vansonii, an Endemic Amaryllid.[Pubmed:28217929]

Phytother Res. 2017 May;31(5):713-720.

Cryptostephanus vansonii I. Verd., an endemic Amaryllidaceae species from Zimbabwe, was evaluated for its acetylcholinesterase (AChE) inhibitory and cytotoxicity properties using Ellman's colorimetric method and the tetrazolium-based colorimetric assay against Vero monkey kidney cells, respectively. The plant extracts were also evaluated for their antibacterial activity against five bacteria. Furthermore, phytochemical profiles of the extracts were determined using ultra-high performance liquid chromatography coupled with tandem mass spectrometry analysis. A plant part-dependent AChE inhibitory activity was observed, in the order, root > rhizome > basal leaf > leaf. Overall, C. vansonii extracts exhibited better antibacterial activity against Gram-negative compared with Gram-positive bacteria. Cytotoxic effects were not detected in Vero monkey kidney cell lines suggesting the possible absence of toxophores in C. vansonii extracts. Similar to the trend in biological activity, a distinct plant part-dependent variation in hydroxybenzoates, hydroxycinnamates and flavonoids was observed in the plant extracts. In addition, 5-hydroxymetylfurfural and Eucomic acid were detected in the different plant parts of C. vansonii. The results of the present study provide valuable AChE inhibition activity, toxicological and phytochemical profiles of C. vansonii. Further studies on isolation of bioactive compounds and their subsequent evaluation in other pharmacological and toxicological model systems are required. Copyright (c) 2017 John Wiley & Sons, Ltd.

Catalytic enantioselective total synthesis of (+)-eucomic acid.[Pubmed:27546916]

Tetrahedron. 2016 Jun 30;72(26):3707-3712.

A catalytic enantioselective synthesis of (+)-Eucomic acid is reported. A palladium-catalyzed asymmetric allylic alkylation is employed to access the chiral tetrasubstituted alpha-hydroxyacid moiety found in the natural product. The protecting group strategy was investigated, and a protecting group manipulation was made without any appreciable deleterious effects in the allylic alkylation reaction. Non-natural (+)-Eucomic acid is synthesized in a longest linear sequence of 13 steps.