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1.
Molecules ; 29(10)2024 May 17.
Artículo en Inglés | MEDLINE | ID: mdl-38792233

RESUMEN

Considering the escalating resistance to conventional antifungal medications, it is critical to identify novel compounds that can efficiently counteract this challenge. The purpose of this research was to elucidate the fungicidal properties of secondary metabolites derived from Arcangelisia flava, with a specific focus on their efficacy against Candida species. This study utilized a combination approach comprising laboratory simulations and experiments to discern and evaluate the biologically active constituents present in the dichloromethane extract of A. flava. The in vitro experiments demonstrated that compounds 1 (palmatine) and 2 (fibraurin) exhibited antifungal properties. The compounds exhibited minimum inhibitory concentrations (MICs) ranging from 15.62 to 62.5 µg/mL against Candida sp. Moreover, compound 1 demonstrated a minimum fungicidal concentration (MFC) of 62.5 µg/mL against Candida glabrata and C. krusei. In contrast, compound 2 exhibited an MFC of 125 µg/mL against both Candida species. Based on a molecular docking study, it was shown that compounds 1 and 2 have a binding free energy of -6.6377 and -6.7075 kcal/mol, respectively, which indicates a strong affinity and specificity for fungal enzymatic targets. This study utilized pharmacophore modeling and Density Functional Theory (DFT) simulations to better understand the interaction dynamics and structural properties crucial for antifungal activity. The findings underscore the potential of secondary metabolites derived from A. flava to act as a foundation for creating novel and highly efficient antifungal treatments, specifically targeting fungal diseases resistant to existing treatment methods. Thus, the results regarding these compounds can provide references for the next stage in antifungal drug design. Further investigation is necessary to thoroughly evaluate these natural substances' clinical feasibility and safety characteristics, which show great potential as antifungal agents.


Asunto(s)
Antifúngicos , Candida , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Antifúngicos/farmacología , Antifúngicos/química , Candida/efectos de los fármacos , Metabolismo Secundario , Extractos Vegetales/farmacología , Extractos Vegetales/química , Apocynaceae/química , Simulación por Computador
2.
Toxicon ; 241: 107679, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38447765

RESUMEN

The search for mechanism-based anti-inflammatory therapies is of fundamental importance to avoid undesired off-target effects. Phospholipase A2 (PLA2) activity is a potential molecular target for anti-inflammatory drugs because it fuels arachidonic acid needed to synthesize inflammation mediators, such as prostaglandins. Herein, we aim to investigate the molecular mechanism by which ß-keto amyrin isolated from a methanolic extract of Cryptostegia grandiflora R. Br. Leaves can inhibit inflammation caused by Daboia russellii viper (DR) venom that mainly contains PLA2. We found that ß-keto amyrin neutralizes DR venom-induced paw-edema in a mouse model. Molecular docking of PLA2 with ß-keto amyrin complex resulted in a higher binding energy score of -8.86 kcal/mol and an inhibition constant of 611.7 nM. Diclofenac had a binding energy of -7.04 kcal/mol and an IC50 value of 620 nM, which predicts a poorer binding interaction than ß-keto amyrin. The higher conformational stability of ß-keto amyrin interaction compared to diclofenac is confirmed by molecular dynamics simulation. ß-keto amyrin isolated from C. grandiflora inhibits the PLA2 activity contained in Daboia russellii viper venom. The anti-inflammatory property of ß-keto amyrin is due to its direct binding into the active site of PLA2, thus inhibiting its enzyme activity.


Asunto(s)
Apocynaceae , Daboia , Inflamación , Ácido Oleanólico , Venenos de Víboras , Animales , Ratones , Antiinflamatorios/farmacología , Apocynaceae/química , Diclofenaco/farmacología , Diclofenaco/uso terapéutico , Inflamación/inducido químicamente , Inflamación/tratamiento farmacológico , Simulación del Acoplamiento Molecular , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/farmacología , Ácido Oleanólico/uso terapéutico , Fosfolipasas A2/efectos de los fármacos , Fosfolipasas A2/metabolismo , Venenos de Víboras/química , Venenos de Víboras/toxicidad
3.
Chem Biodivers ; 21(4): e202301786, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38466126

RESUMEN

SARS-CoV-2 caused pandemic represented a major risk for the worldwide human health, animal health and economy, forcing extraordinary efforts to discover drugs for its prevention and cure. Considering the extensive interest in the pregnane glycosides because of their diverse structures and excellent biological activities, we investigated them as antiviral agents against SARS-COV-2. We selected 21 pregnane glycosides previously isolated from the genus Caralluma from Asclepiadaceae family to be tested through virtual screening molecular docking simulations for their potential inhibition of SARS-CoV-2 Mpro. Almost all target compounds showed a more or equally negative docking energy score relative to the co-crystallized inhibitor X77 (S=-12.53 kcal/mol) with docking score range of (-12.55 to -19.76 kcal/mol) and so with a potent predicted binding affinity to the target enzyme. The activity of the most promising candidates was validated by in vitro testing. Arabincoside C showed the highest activity (IC50=35.42 µg/ml) and the highest selectivity index (SI=9.9) followed by Russelioside B (IC50=50.80 µg/ml), and Arabincoside B (IC50=53.31 µg/ml).


Asunto(s)
Apocynaceae , COVID-19 , Proteasas 3C de Coronavirus , Animales , Humanos , Antivirales/farmacología , Antivirales/química , Apocynaceae/química , Proteasas 3C de Coronavirus/antagonistas & inhibidores , Glicósidos/farmacología , Glicósidos/química , Simulación del Acoplamiento Molecular , Simulación de Dinámica Molecular , Pregnanos/farmacología , Pregnanos/química , Inhibidores de Proteasas/farmacología , Inhibidores de Proteasas/química , SARS-CoV-2/efectos de los fármacos , SARS-CoV-2/metabolismo
4.
Fitoterapia ; 174: 105873, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38417682

RESUMEN

Diabetes mellitus stands as a metabolic ailment marked by heightened blood glucose levels due to inadequate insulin secretion. The primary aims of this investigative inquiry encompassed the isolation of phytochemical components from the bark of Kopsia teoi, followed by the assessment of their α-amylase inhibition. The phytochemical composition of the K. teoi culminated in the discovery of a pair of new indole alkaloids; which are 16-epi-deacetylakuammiline N(4)-methylene chloride (akuammiline) (1), and N(1)-methoxycarbonyl-11-methoxy-12-hydroxy-Δ14-17-kopsinine (aspidofractinine) (2), together with five known compounds i.e. kopsiloscine G (aspidofractinine) (3), akuammidine (sarpagine) (4), leuconolam (aspidosperma) (5), N-methoxycarbonyl-12-methoxy-Δ16, 17-kopsinine (aspidofractinine) (6), and kopsininate (aspidofractinine) (7). All compounds were determined via spectroscopic analyses. The in vitro evaluation against α-amylase showed good inhibitory activities for compounds 5-7 with the inhibitory concentration (IC50) values of 21.7 ± 1.2, 34.1 ± 0.1, and 30.0 ± 0.8 µM, respectively compared with the reference acarbose (IC50 = 34.4 ± 0.1 µM). The molecular docking outputs underscored the binding interactions of compounds 5-7 ranging from -8.1 to -8.8 kcal/mol with the binding sites of α-amylase. Consequently, the outcomes highlighted the anti-hyperglycemic attributes of isolates from K. teoi.


Asunto(s)
Apocynaceae , Alcaloides de Triptamina Secologanina , Simulación del Acoplamiento Molecular , alfa-Amilasas , Estructura Molecular , Alcaloides Indólicos , Fitoquímicos/farmacología , Apocynaceae/química
5.
Chem Biodivers ; 21(4): e202400188, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38372184

RESUMEN

Two rare 5/5/5/6 four-ring system iridoids, allamancins A and B (1 and 2) together with one known biogenetically related iridoid derivative, 3-O-methyallamancin (3) were isolated from the flowers of Plumeria alba L. The structures of these iridoid derivatives were determined by comprehensive spectroscopic analyses. The absolute configuration of 1 was confirmed by X-ray crystallographic analysis. The inhibitory activities of compounds 1-3 against nitric oxide (NO) production induced and three cancer cell lines were evaluated in vitro. Compounds 1 and 3 showed inhibitory activities on NO production with IC50 values of 18.3±0.12 and 22.1±0.14 µM, respectively. Compounds 1-3 showed moderate inhibitory activities against cancer cell lines of A549, Hela and MCF-7.


Asunto(s)
Apocynaceae , Iridoides , Humanos , Iridoides/farmacología , Iridoides/química , Células HeLa , Apocynaceae/química , Óxido Nítrico/metabolismo , Cristalografía por Rayos X , Estructura Molecular
6.
J Nat Prod ; 87(2): 286-296, 2024 02 23.
Artículo en Inglés | MEDLINE | ID: mdl-38284153

RESUMEN

Nine new alkaloids, eugeniinalines A-H (1-8) and (+)-eburnamenine N-oxide (9), comprising one quinoline, six indole, and two isogranatanine alkaloids, were isolated from the stem-bark extract of the Malayan Leuconotis eugeniifolia. The structures and absolute configurations of these alkaloids were established based on the analysis of the spectroscopic data, GIAO NMR calculations, DP4+ probability analysis, TDDFT-ECD method, and X-ray diffraction analysis. Eugeniinaline A (1) represents a new pentacyclic quinoline alkaloid with a 6/6/5/6/7 ring system. Eugeniinaline G (7) and its seco-derivative, eugeniinaline H (8), were the first isogranatanine alkaloids isolated as natural products. The known alkaloids leucolusine (10) and melokhanine A (11) were found to be the same compound, based on comparison of the spectroscopic data of both compounds, with the absolute configuration of (7R, 20R, 21S). Eugeniinalines A and G (1 and 7) showed cytotoxic activity against the HT-29 cancer cell line with IC50 values of 7.1 and 7.2 µM, respectively.


Asunto(s)
Alcaloides , Antineoplásicos , Apocynaceae , Quinolinas , Humanos , Alcaloides/farmacología , Apocynaceae/química , Alcaloides Indólicos/farmacología , Alcaloides Indólicos/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Quinolinas/farmacología , Alcaloides de Triptamina Secologanina/química , Alcaloides de Triptamina Secologanina/farmacología
7.
J Ethnopharmacol ; 321: 117506, 2024 Mar 01.
Artículo en Inglés | MEDLINE | ID: mdl-38012976

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Hancornia speciosa Gomes is a fruit and medicinal species used for treating infectious diseases of the genitourinary system. However, its mechanism of action against microbes is still not fully understood. Infections in the genitourinary system caused by Candida spp. are associated with its fungal resistance and pathogenicity. New plant-derived compounds are an alternative to fight these Candida infections. AIM OF THE STUDY: The objective of this study was to evaluate the anti-Candida effects of extracts of the stem bark of H. speciosa. This research investigated the chemical composition of sulfuric ether (EEHS) and methanolic (MEHS) extracts, their drug-modifying action on fluconazole, and their anti-virulence action on the morphological transition of Candida species. MATERIALS AND METHODS: The extracts (EEHS and MEHS) of the stem bark of H. speciosa were chemically characterized via qualitative phytochemical screening and by liquid chromatography coupled with mass spectrometry (UPLC-MS-ESI-QTOF). The extracts were evaluated regarding their antifungal effects and fluconazole-modifying activity against Candida albicans, Candida krusei, and Candida tropicalis using the broth microdilution method. Additionally, the study evaluated the inhibition of fungal virulence in Candida species through morphological transition assays. RESULTS: The phytochemical screening revealed the presence of anthocyanidins, anthocyanins, aurones, catechins, chalcones, flavones, flavonols, flavanones, leucoanthocyanidins, tannins (condensed and pyrogallic), and xanthones in both extracts of the stem bark of H. speciosa. The UPLC-MS-ESI-QTOF analysis identified the same compounds in both extracts, predominating phenolic compounds. Some compounds were first time recorded in this species: gluconic acid, cinchonain IIb, cinchonain Ib isomer, and lariciresinol hexoside isomers. Most of the intrinsic antifungal activity was observed for the MEHS against C. krusei (IC50: 58.41 µg/mL). At subinhibitory concentrations (MC/8), the EEHS enhanced the action of fluconazole against all Candida strains. The MEHS exhibited greater efficacy than fluconazole inhibiting C. krusei growth. The EEHS completely inhibited hyphae appearance and reduced pseudohyphae formation in C. albicans. CONCLUSION: The stem bark of H. speciosa is a rich source of bioactive compounds, especially phenolic. Phenolic compounds can have important roles in fighting infectious diseases of the genitourinary system, such as candidiasis. The extracts of H. speciosa improved the action of the drug fluconazole against Candida species, inhibited hyphae appearance, and reduced pseudohyphae formation. The results of this study can support the development of new therapeutics against resistant strains of Candida.


Asunto(s)
Apocynaceae , Candidiasis , Enfermedades Transmisibles , Antifúngicos/farmacología , Antifúngicos/química , Candida , Fluconazol/farmacología , Virulencia , Cromatografía Liquida , Apocynaceae/química , Corteza de la Planta/química , Antocianinas/farmacología , Extractos Vegetales/farmacología , Extractos Vegetales/química , Espectrometría de Masas en Tándem , Candida albicans , Fitoquímicos/análisis , Pruebas de Sensibilidad Microbiana
8.
Phytochemistry ; 217: 113903, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37918619

RESUMEN

Chemical investigation of Caralluma hexagona Lavranos, a wild plant growing in Yemen, led to the isolation of four previously undescribed acylated pregnane glycosides, hexagonosides A-D (1-4), together with two sets of mixtures (hexagonosides E and F), each set consists of three interconvertible pregnane glycoside isomers, hexagonosides E (5a-c) and F (6a-c). The chemical structures of the isolated pregnane glycosides were elucidated by extensive 1D/2D NMR and HRESI-MS analysis, featuring 6'-O-benzoyl-1'-O-ß-glucosyl residue at aglycone C-20; while aglycone C-3 was substituted with disaccharide sugar chain (1, 2, 5a-c) or a trisaccharide sugar chain (3, 4, 6a-c). Metabolites E and F included an extra benzoyl substitution in C-20 glucosyl residue which is migrating between the OH groups of C-2', C-3' and C-4' resulting in equilibrating conformations (5a-c and 6a-c) when incubated in HPLC solvent, which we confirmed by the analytical study.


Asunto(s)
Apocynaceae , Glicósidos , Glicósidos/química , Pregnanos/química , Apocynaceae/química , Azúcares , Estructura Molecular
9.
Int J Biol Macromol ; 252: 126529, 2023 Dec 01.
Artículo en Inglés | MEDLINE | ID: mdl-37633557

RESUMEN

Although latex fluids are found in >20,000 plant species, the biochemical composition and biological function of their proteins are still poorly explored. Thus, this work aimed to conduct a proteomic analysis of Cryptostegia grandiflora latex (CgLP) for subsequent purification and characterization of an antifungal protein. After 2D-SDS-PAGE and mass spectrometry, 27 proteins were identified in CgLP, including a polygalacturonase inhibitor, cysteine peptidases, pathogenesis-related proteins (PR-4), and osmotins. Then, two osmotin isoforms (CgOsm) were purified, and a unique N-terminal sequence was determined (1ATFDIRSNCPYTVWAAAVPGGGRRLDRGQTWTINVAPGTA40). The PCR products revealed a cDNA sequence of 609 nucleotides for CgOsm, which encoded a polypeptide with 203 amino acid residues. The structure of CgOsm has features of typical osmotin or thaumatin-like proteins (TLPs), such as 16 conserved Cys residues, REDDD and FF motifs, an acidic cleft, and three main domains. Atomic force microscopy (AFM) and bioinformatics suggested that CgOsm is associated with three chain units. This result was interesting since the literature describes osmotins and TLPs as monomers. AFM also showed that Fusarium falciforme spores treated with CgOsm were drastically damaged. Therefore, it is speculated that CgOsm forms pores in the membrane of these cells, causing the leakage of cytoplasmic content.


Asunto(s)
Apocynaceae , Látex , Látex/química , Proteómica , Proteínas de Plantas/química , Isoformas de Proteínas/genética , Apocynaceae/química
10.
PLoS One ; 18(7): e0288032, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-37478090

RESUMEN

Rhazya Stricta (R. stricta) has been employed as a natural remedy for several diseases for centuries. Numerous studies revealed that R. stricta extracts contain alkaloids, tannins, and flavonoids that possess antimicrobial, anticancer, antihypertensive, and antioxidant activities. In this study, we examined the effects of organic extracts from different parts of R. stricta plant on human pluripotent stem cells (hiPSCs)-derived neural stem cells (NSCs) for medical purposes. NSCs were incubated with different concentrations of organic extracts from the leaves, stem, and fruits, and we assessed the growth and viability of the cells by using MTS assay and the chemical composition of the potential plant extract by using gas chromatography-mass spectrometry (GC/MS). Our results revealed that the methanolic extract from the stem increased NSCs growth significantly, particularly at a concentration of 25 µg/ml. GC/MS analysis was utilized to identify the potential compounds of the methanolic extract. In conclusion, our results demonstrated for the first time that methanolic stem extract of R. stricta contains compounds that can positively impact NSCs growth. These compounds can be further investigated to determine the potential bioactive compounds that can be used for research and medical purposes.


Asunto(s)
Alcaloides , Apocynaceae , Células Madre Pluripotentes Inducidas , Humanos , Extractos Vegetales/química , Alcaloides/análisis , Antioxidantes/química , Apocynaceae/química , Hojas de la Planta/química
11.
Angew Chem Int Ed Engl ; 62(37): e202307286, 2023 09 11.
Artículo en Inglés | MEDLINE | ID: mdl-37490018

RESUMEN

We report here a homo-Mannich reaction of cyclopropanol with an iminium ion, generated by an asymmetric allylic dearomatization of indole, to construct a tricyclic hydrocarbazole core, which is shared by a variety of monoterpenoid indole alkaloids across families. Through this approach, an all-carbon quaternary stereogenic center as well as an allyl and a ketone group were installed. Using this functionalized hydrocarbazole as the structural platform, D ring and E rings of different sizes (i.e., five-, six-, and seven-membered) were successively or simultaneously assembled, leading to a collective asymmetric synthesis of seven alkaloids belonging to the ibophyllidine, Aspidosperma, Kopsia, and Melodinus alkaloid families.


Asunto(s)
Apocynaceae , Aspidosperma , Alcaloides de Triptamina Secologanina , Humanos , Aspidosperma/química , Apocynaceae/química , Alcaloides Indólicos/química , Estructura Molecular
12.
Phytochemistry ; 213: 113752, 2023 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-37330032

RESUMEN

Four undescribed tryptamine-derived alkaloids, hunteriasines A - D, were isolated and identified from Hunteria umbellata (Apocynaceae), together with fifteen known indole alkaloids. The chemical structure and absolute configuration of hunteriasine A were determined by spectroscopic and X-ray crystallographic data analyses. Hunteriasine A, featuring with a unique scaffold comprised of tryptamine and an unprecedented "12-carbon unit" moiety, is a zwitterionic indole-derived and pyridinium-containing alkaloid. Hunteriasines B - D were identified by spectroscopic data analyses and theoretical calculations. A plausible biogenetic pathway for hunteriasines A and B was proposed. The lipopolysaccharide-stimulated mouse macrophage cell line J774A.1 cell-based bioactivity assays revealed that (+)-eburnamine, strictosidinic acid, and (S)-decarbomethoxydihydrogambirtannine enhance the release of interleukin-1ß.


Asunto(s)
Alcaloides , Apocynaceae , Alcaloides de Triptamina Secologanina , Ratones , Animales , Alcaloides/farmacología , Alcaloides Indólicos/farmacología , Alcaloides Indólicos/química , Apocynaceae/química , Extractos Vegetales/química , Triptaminas/farmacología , Estructura Molecular , Alcaloides de Triptamina Secologanina/química
13.
PeerJ ; 11: e15320, 2023.
Artículo en Inglés | MEDLINE | ID: mdl-37250712

RESUMEN

The use of wild plants is considered to be an eco-friendly and promising natural resource. In sandy desert habitats, Leptadenia pyrotechnica flourishes as a xerophytic shrub with high biomass production. As a dominant shrub in the arid sand dune habitats of Saudi Arabia, Leptadenia pyrotechnica (Forssk.) Decne (Asclepiadaceae) is one of the most common xerophytes; the many medicinal uses of this plant include treating allergies, productive coughs, abortions, diabetes, stomach disorders, fevers, kidney disorders, and stones. In such a distribution, morpho-anatomical characteristics, among other adaptive traits, play an important role. This study aims to characterize some morpho-anatomical adaptations of L. pyrotechnica in two stressful habitats: the hyper-arid inland sand dunes of the Empty Quarter (EQ) and the arid coastal sand dunes of Jazan. A morpho-anatomical analysis of plant stems and roots from both habitats was conducted using light microscopy (LM) and scanning electron microscopy (SEM). The outcomes indicated similar characteristics, a low surface-to-volume ratio (S/V), a thin boundary layer (δbl), an epidermis with many layers of hypodermis, bundles of sclerenchymatous cells around vascular tissue, and storage starch grains in ray parenchyma between xylem conduits. On the other hand, the L. pyrotechnica stem from the hyper-arid habitat of the Empty Quarter revealed more encrypted stomata, more elongated palisade cells, less calcium oxalate crystals with low Ca percentage, and a high vulnerability index of xylem vessels compared with the same traits of the stem from the Jazan coastal sand dunes habitat. Roots of L. pyrotechnica from both habitats revealed similar features of general anatomy. However, differences in specific anatomical traits were observed, especially in xylem vessel characters. The vulnerability index of root xylem vessels from the Empty Quarter habitat was more than that from the Jazan coastal sand dunes habitat. Furthermore, vestured bordered pits in root xylem walls were more abundant in the Empty Quarter habitat than in the Jazan coastal sand dunes habitat. As a result, these characteristics in the morpho-anatomy of L. pyrotechnica from both habitats provide practical adaptations to highly stressful conditions, along with specific anatomical traits relating to each habitat.


Asunto(s)
Apocynaceae , Apocynaceae/química , Arena , Arabia Saudita , Ecosistema , Biomasa , Plantas
14.
Phytochemistry ; 211: 113678, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-37059289

RESUMEN

Eight unprecedented monoterpenoid indole alkaloid (MIA) adducts and dimers, melofusinines A-H (1-8), and three undescribed melodinus-type MIA monomers, melofusinines I-K (9-11), together with six putative biogenetic precursors were isolated from the twigs and leaves of Melodinus fusiformis Champ. ex Benth. Compounds 1 and 2 are unusual hybrid indole alkaloids incorporating an aspidospermatan-type MIA with a monoterpenoid alkaloid unit via C-C coupling. Compounds 3-8 feature the first MIA dimers constructed through an aspidospermatan-type monomer and a rearranged melodinus-type monomer with two different types of couplings. Their structures were elucidated by spectroscopic data, single crystal X-ray diffraction, and calculated electric circular dichroism spectra analysis. In addition, dimers 5 and 8 showed significant neuroprotection effects on MPP +-injured primary cortical neurons.


Asunto(s)
Antineoplásicos , Apocynaceae , Alcaloides de Triptamina Secologanina , Monoterpenos/análisis , Alcaloides Indólicos/farmacología , Alcaloides Indólicos/análisis , Hojas de la Planta/química , Apocynaceae/química , Alcaloides de Triptamina Secologanina/farmacología , Alcaloides de Triptamina Secologanina/química , Estructura Molecular
15.
Molecules ; 28(4)2023 Feb 13.
Artículo en Inglés | MEDLINE | ID: mdl-36838767

RESUMEN

Caralluma europaea (Guss.) is an important medicinal plant widely used in Morocco for various traditional purposes. Our work aimed to evaluate the phenolic composition, wound healing, antinociceptive, and anticancer activities of C. europaea extracts. Moreover, this study assessed the beneficial effect of C. europaea phytocompounds on the TRADD, cyclooxegenase-2, Wnt/ß-catenin, and tyrosine kinase signaling pathways. The wound healing effect of C. europaea formulations against skin burn was evaluated for 21 days. The cytotoxic effect of the C. europaea extracts was evaluated against human leukemic (K562 and HL60) and liver cancer cell lines (Huh-7) using the MTT test. All the phytoconstituents identified by UHPLC in the polyphenols were docked for their inhibitory power on protein casein kinase-1, glycogen synthase kinase-3-ß, cyclooxegenase-2, tyrosine kinase, and TRADD. Luteolin and kaempferol are the main compounds identified in C. europaea polyphenols. The group treated with polyphenols showed the greatest wound contractions and all tested extracts presented a significant antinociceptive effect. Polyphenols showed a remarkable antitumoral activity against the K562, HL60 and Huh-7 cell lines. Saponins exerted an important cytotoxic effect against the Huh-7 cell line, whereas no cytotoxicity was observed for the hydroethanolic and flavonoids extracts. Hesperetin and trimethoxyflavone presented the highest docking G-score on tyrosine kinase and cyclooxygenase, respectively.


Asunto(s)
Analgésicos , Antineoplásicos Fitogénicos , Extractos Vegetales , Polifenoles , Cicatrización de Heridas , Humanos , Analgésicos/farmacología , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Extractos Vegetales/farmacología , Polifenoles/farmacología , Apocynaceae/química
16.
Z Naturforsch C J Biosci ; 78(7-8): 271-274, 2023 Jul 26.
Artículo en Inglés | MEDLINE | ID: mdl-36793235

RESUMEN

The structure and complete NMR assignments of aspidoreticulofractine, an aspidofractinine N-oxide, are reported. Its structure was elucidated based on a combination of spectroscopic techniques including 1D and 2D NMR, high-resolution mass spectrometry, and electronic circular dichroism.


Asunto(s)
Apocynaceae , Monoterpenos , Estructura Molecular , Alcaloides Indólicos/química , Espectroscopía de Resonancia Magnética , Apocynaceae/química
17.
J Nat Prod ; 86(1): 232-236, 2023 01 27.
Artículo en Inglés | MEDLINE | ID: mdl-36651825

RESUMEN

Eugeniifoline (1), a pentacyclic indole alkaloid with a five-membered ring E, was isolated for the first time as a natural product from the stem-bark extract of Leuconotis eugeniifolia. Eugeniifoline (1) was previously reported as a synthetic product from a diversity-enhanced extract, but with the configuration at C-21 reported as S (1a). The configuration at C-21 was revised to R as shown in 1, based on the NOE data, GIAO NMR calculations, and DP4+ probability analysis, as well as the TDDFT-ECD method.


Asunto(s)
Apocynaceae , Alcaloides Indólicos , Apocynaceae/química , Alcaloides Indólicos/química , Estructura Molecular , Extractos Vegetales
18.
Nat Prod Res ; 37(7): 1047-1052, 2023 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-34583594

RESUMEN

Two new monoterpenoid indole alkaloids, (2 R, 7 R, 16 R, 20 R, 21S)-12-hydroxypleiocarpine (1) and (2S, 7 R, 16S, 20 R, 21S)-N-methoxycarbonyl-11,12-methylenedioxy-Δ14,15-kopsinaline (2), along with six known alkaloids were isolated from the methanol extract of the kernels of Kopsia arborea. Their structures including the absolute configurations were elucidated by HRESIMS, NMR spectroscopy, and quantum computational methods. Their cytotoxicity against two human cancer cell lines were also evaluated.


Asunto(s)
Apocynaceae , Alcaloides de Triptamina Secologanina , Humanos , Alcaloides de Triptamina Secologanina/farmacología , Alcaloides de Triptamina Secologanina/química , Alcaloides Indólicos/farmacología , Alcaloides Indólicos/química , Estructura Molecular , Espectroscopía de Resonancia Magnética , Apocynaceae/química
19.
Braz. j. biol ; 83: 1-5, 2023. tab, ilus
Artículo en Inglés | LILACS, VETINDEX | ID: biblio-1468968

RESUMEN

Plant-derived products can assist in the healing process of dermal wounds. It has been demonstrated that Hancornia speciosa latex present angiogenic, osteogenic, anti-inflammatory, and antioxidant activities. Then, it could contribute to the wound healing process. However, natural products in contact with skin may cause dermatitis. The objective of this work was to evaluate the allergic and irritant potential of H. speciosa serum fraction latex using in vitro assays. The obtained results showed that the H. speciosa serum fraction latex has a slightly irritant potential and is not cytotoxic neither allergenic for human cells. Moreover, we identified a remarkable low amount of proteins in this material in comparison to Hevea brasiliensis latex. This result could explain the non-allergenic potential of H. speciosa serum fraction latex because proteins present in latex are the main responsible for allergy. This biomaterial could be used as a non-allergenic source for development of new medicines.


Produtos derivados de plantas podem auxiliar no processo de cicatrização de feridas cutâneas. Foi demonstrado que o látex de Hancornia speciosa apresenta atividades angiogênicas, osteogênicas, antiinflamatórias e antioxidantes. Então, este biomaterial pode contribuir para o processo de cicatrização de feridas. No entanto, produtos naturais em contato com a pele podem causar dermatites. O objetivo deste trabalho foi avaliar o potencial alérgico e irritante do látex da fração soro de H. speciosa por meio de ensaios in vitro. Os resultados obtidos mostraram que o látex da fração do soro de H. speciosa possui um potencial pouco irritante e não é citotóxico nem alergênico para células humanas. Além disso, foi identificado uma notável baixa quantidade de proteínas neste material em comparação ao látex de Hevea brasiliensis. Esse resultado poderia explicar o potencial não alergênico do látex da fração soro de H. speciosa, pois as proteínas presentes no látex são as principais responsáveis pela alergia. Este biomaterial pode ser utilizado como fonte não alergênica para desenvolvimento de novos medicamentos.


Asunto(s)
Apocynaceae/química , Cicatrización de Heridas/efectos de los fármacos , Técnicas In Vitro
20.
Braz. j. biol ; 83: 1-9, 2023. tab
Artículo en Inglés | LILACS, VETINDEX | ID: biblio-1468989

RESUMEN

Among several fruits, mangaba (Hancornia speciosa Gomes), it aroused the interest of producers and consumers due to its attractive sensory characteristics and health beneficial properties (high nutritional value and presence of bioactive substances), thus, this work evaluates the nutritional factors of the flour residue of mangaba processing that is despised by the food industry, and the influence of temperature on its production. The mangaba processing residue was splited in two main groups: in natura sample (control), and other for preparation of flour that was dried at 50 °C and divided into two other groups: treatment A (flour with roasts at 110 °C and 130 °C) and treatment B (flour from drying at 50 °C). The nutritional characteristics of flours were analyzed considering the chemical parameters: pH, titratable total acidity and soluble solids, in addition to the determination of moisture content, total lipids, total dietary fiber and ash, total energy value, antioxidant activity, phytochemical screening, quantification of phenolic compounds and flavonoids, as well as technological functional properties (water absorption index (WAI), water solubility index (WSI), milk absorption index (MAI) and milk solubility index (MSI) and oil absorption index (OAI). The results showed that the bioactive compounds present in the extracts do not have significant properties of acting as free radical kidnappers. The heat treatment, performed in the flour of mangaba processing residues, influenced the nutritional factors and properties of absorption and solubility, which showed statistical differences. These results show that the flour is a viable alternative for the energy enrichment of diets, contributing to the development of new products, the reduction of the disposal of these residues and consequently to the minimization of the environmental impact.


Dentre as diversas frutas a mangaba (Hancornia speciosa Gomes), despertou interesse de produtores e consumidores devido às suas características sensoriais atrativas e propriedades benéficas à saúde (elevado valor nutricional e presença de substâncias bioativas), assim, o trabalho avaliar os fatores nutricionais do resíduo da farinha de processamento de mangaba que é desprezado pela indústria alimentícia e, a influência da temperatura na sua produção. O resíduo de processamento da mangaba foi dividido em dois lotes, sendo um deles utilizado para as análises in natura (amostra controle) e o outro para a confecção da farinha que foi seca a 50 °C, e dividida em dois lotes: tratamento A (farinha com torras a 110 °C e 130 °C) e no tratamento B (farinha oriunda da secagem a 50 °C). Analisou-se as características nutricionais de farinhas considerando os parâmetros químicos: pH, acidez total titulável e sólidos solúveis, além da determinação do teor de umidade, lipídios totais, fibra alimentar total e cinzas, valor energético total, atividade antioxidante, triagem fitoquímica, quantificação de compostos fenólicos e flavonoides, bem como as propriedades funcionais tecnológicas (índice de absorção de água (IAA), índice de solubilidade em água (ISA), índice de absorção de leite (IAL) e índice de solubilidade em leite (ISL) e índice de absorção de óleo (IAO). Na análise foi inferido que os compostos bioativos presentes nos extratos não possuem propriedades significativas de agir como sequestradores de radicais livres. O tratamento térmico, realizado na farinha de resíduos de processamento de mangaba, influenciou nos dados dos fatores nutricionais e das propriedades de absorção e solubilidade, os quais apresentaram diferenças estatísticas. Estes resultados credenciam a farinha como uma alternativa viável para o enriquecimento energético de dietas, contribuindo para o desenvolvimento de [...].


Asunto(s)
Apocynaceae/química , Estándar de Identidad y Calidad de Productos y Servicios , Residuos de Alimentos
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