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p> Clusia minor L. is traditionally used to treat many disorders that including pain and inflammation such as sores and warts. Four extracts from the leaves of plant were prepared: hexane (CMH-A), ethyl acetate (CMH-B), methanol (CMH-C) and ethanol (CMH-E) and the pharmacological (antioxidant and anti-inflammatory properties) and toxicity effects w...
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Family Clusiaceae is spread throughout tropical as well as temperate zones, presenting many triterpenes, reported as selective antitumoral agents. The aim of this study is to isolate and identify triterpenes from Clusia studartiana C. M. Vieira & Gomes da Silva and evaluate their cytotoxicity in melanoma (SKMEL 28) and myeloid leukemia (K562) cell...
Citations
... Among tested Clusia species, C. minor had the highest tocochromanol content, composed mainly of α-T, followed by δ-T3. The presence of α-T in C. minor leaf ethyl acetate and methanol extracts was documented before with GC-MS, but δ-T3 was not identified in the study [53] and the concentration was much lower (3.29% and 2.50% of the extract, respectively). ...
... Tocopherol and tocotrienol fatty acid esters are the most common tocochro-0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 Among tested Clusia species, C. minor had the highest tocochromanol content, composed mainly of α-T, followed by δ-T3. The presence of α-T in C. minor leaf ethyl acetate and methanol extracts was documented before with GC-MS, but δ-T3 was not identified in the study [53] and the concentration was much lower (3.29% and 2.50% of the extract, respectively). ...
Now under Clusiaceae and Hypericaceae, Clusia and Hypericum were previously categorized under one family until they were divided in 2003 by the APG III system. The Clusia genus is characterized by the presence of tocotrienol derivatives with antiangiogenic properties, and only Hypericum perforatum tocochromanol content has been studied in the Hypericum genus. Twelve species were analyzed: H. aegypticum, H. calycinum, H. empetrifolium, H. lancasteri, H. olympicum f. minus ‘Sulphureum’, H. perforatum, H. xylosteifolium, C. fluminensis, C. minor, C. odorata, C. palmicida, and C. tocuchensis. Plant leaves were analyzed for their tocochromanol (α-, β-, γ-, and δ-tocotrienol and tocopherol) contents using a reverse-phase high-performance liquid chromatography with fluorescent light detector (RP-HPLC-FLD) method. While α-tocopherol (α-T) was present in the highest proportion, the leaves had significant tocotrienol (T3) contents. Following α-T, δ-T3 was present in most Clusia samples, and γ-T3 in most Hypericum samples, except H. olympicum, in which α-T3 followed. C. minor had the highest α-T (112.72 mg 100 g−1) and total tocochromanol (141.43 mg 100 g−1) content, followed by C. palmicida (65.97 and 82.96 mg 100 g−1, respectively) and H. olympicum (α-T 32.08, α-T3 30.68, and total tocochromanols 89.06 mg 100 g−1). The Hypericum genus is a valuable source of tocotrienols, with potential use after purification.
... Extracts from its leaves exhibit antioxidant, anti-inflammatory, and cytotoxic activities based on in vitro and in vivo studies. 26 The antinociceptive potential of C. minor extract was confirmed in a model to assess inflammatory hyperalgesia in mice. The analgesic action was achieved in a dose-dependent manner probably through peripheral and central pathways that modulate pain. ...
... 28 In another study, three polyprenylated benzophenones derivatives (propolone D, hyperibone B, and garcinielliptone I, all m/z 519 [M + H] + ), were isolated from its fruits. 29 More recent studies focused on the GC-MS analysis of its leaves, with the detection of sterols, triterpenes, volatiles, and vitamin E. 26,27 With an increasing interest in the Clusia genus' health benefits and the lack of detailed phytochemical studies of its species to justify such applications scientifically, and also to evaluate other potential uses based on its rich constituents, the objective of the present work was to assess the metabolome variation of C. minor organs at different developmental stages via UPLC-MS and NMR fingerprinting. One successful application of HMBC in H. lupulus (hops) resin classification from different cultivars coupled to multivariate data analysis such as PCA has been reported by our group, 30 which we extend herein for the assessment of ontogenic effects in Clusia for its different organs including leaf, flower, fruit, and seed. ...
Introduction: The genus ClusiaL. is mostly recognized for the production of preny-lated benzophenones and tocotrienol derivatives.
Objectives: The objective of this study was to map metabolome variation within Clusia minor organs at different developmental stages.
Material and Methods: In total 15 organs/stages (leaf, flower, fruit, and seed) were analysed by UPLC-MS and1 H- and heteronuclear multiple-bond correlation (HMBC)-NMR-based metabolomics
.Results:This work led to the assignment of 46 metabolites, belonging to organic acids(1), sugars(2) phenolic acids(1), flavonoids(3) prenylated xanthones(1)benzophenones(4) and tocotrienols(2). Multivariate data analyses explained the vari-ability and classification of samples, highlighting chemical markers that discriminateeach organ/stage. Leaves were found to be rich in 5-hydroxy-8-methyltocotrienol(8.5μg/mg f.w.), while flowers were abundant in the polyprenylated benzophenonenemorosone with maximum level detected in the fully mature flower bud (43μg/mgf.w.). Nemorosone and 5-hydroxy tocotrienoloic acid were isolated from FL6 for fullstructural characterisation. This is the first report of the NMR assignments of5-hydroxy tocotrienoloic acid, and its maximum level was detected in the maturefruit at 50μg/mg f.w. Seeds as typical storage organ were rich in sugars andomega-6 fatty acids.
Conclusion:To the best of our knowledge, this is the first report on a comparative1D-/2D-NMR approach to assess compositional differences in ontogeny studies compared with LC-MS exemplified by Clusia organs. Results derived from this stud yprovide better understanding of the stages at which maximal production of natural compounds occur and elucidate in which developmental stages the enzymes responsible for the production of such metabolites are preferentially expressed
... The methanolic crude extract of T. sanguinea and its ethyl acetate fraction were dissolved to a concentration of 1 g/10 mL, individually, then each was diluted tenfold. Both diluted solutions were applied under the above-mentioned conditions [34]. Then, the compounds under investigation were identified by comparing their retention time and spectral data with those of the standard isolated compounds. ...
Medicinal plants are widely used in folk medicine to treat various diseases. Thonningia sanguinea Vahl is widespread in African traditional medicine, and exhibits antioxidant, antibacterial, antiviral, and anticancer activities. T. sanguinea is a source of phytomedicinal agents that have previously been isolated and structurally elucidated. Herein, gas chromatography combined with tandem mass spectrometry (GC-MS/MS) was used to quantify epipinoresinol, β-sitosterol, eriodictyol, betulinic acid, and secoisolariciresinol contents in the methanolic crude extract and its ethyl acetate fraction for the first time. The ethyl acetate fraction was rich in epipinoresinol, eriodictyol, and secoisolariciresinol at concentrations of 2.3, 3.9, and 2.4 mg/g of dry extract, respectively. The binding interactions of these compounds with the epidermal growth factor receptor (EGFR) were computed using a molecular docking study. The results revealed that the highest binding affinities for the EGFR signaling pathway were attributed to eriodictyol and secoisolariciresinol, with good binding energies of −19.93 and −16.63 Kcal/mol, respectively. These compounds formed good interactions with the key amino acid Met 769 as the co-crystallized ligand. So, the ethyl acetate fraction of T. sanguinea is a promising adjuvant therapy in cancer treatments.
... Además, corroboró la presencia de tres de los compuestos aislados, la friedelina y la mezcla β-sitosterol-estigmasterol. (41)(42)(43) La cuantificación de fenoles totales a los extractos de las hojas mostró la mayor concentración en el extracto etanólico (200,09 ±0,83 mg EAG/g), asociado a la extracción directa con etanol. El extracto de acetato de etilo presentó el mayor contenido de flavonoides (100,95 ±0,50 mg EQ/g extracto). ...
... Todos los extractos exhibieron capacidad secuestradora del DPPH siendo el etanólico el de mejores resultados (85 % de inhibición, CI 50 = 10,3 ±3,6 µg/mL). (42) Estos resultados evidencian que la polaridad de los extractos favoreció la capacidad secuestradora del radical DPPH. Por el método de FRAP la capacidad reductora de los extractos fue dependiente de la concentración, siendo el extracto de acetato de etilo el de mejor poder reductor (> 300 µmol/L EAA). ...
... En la determinación de la actividad antiinflamatoria los extractos presentaron un comportamiento dosis-dependiente siendo el de acetato de etilo el de mayor porcentaje de inhibición del edema (82,3 %). (42) Este resultado está relacionado con su variada composición química, así como con el elevado contenido de polifenoles y flavonoides mostrado. Todos los efectos evaluados pudieran atribuirse a algunos de los compuestos identificados. ...
Introducción:
Las plantas son una parte fundamental de los sistemas de medicina. Para contar con una fuente vegetal como alternativa terapéutica, es indispensable demostrar científicamente su utilidad. Las especies Clusia minor L., Caesalpinia bahamensis Lam., Murraya paniculata L, Phania matricarioides (Spreng.) Griseb. y Lippia alba Mill, que crecen en Cuba son utilizadas tradicionalmente para el tratamiento de diferentes afecciones, sin embargo, los estudios fitoquímicos y farmacológicos que avalen esta utilidad y que permitan establecer su calidad, son escasos o nulos. Objetivos: determinar los principales parámetros farmacognósticos para establecer su calidad como droga vegetal, identificar los principales metabolitos presentes en las mismas y evaluar preliminarmente algunas de sus propiedades farmacológicas.
Métodos:
Se determinaron los requerimientos de calidad de algunas de las especies mediante evaluaciones farmacognósticas, se aplicaron métodos fitoquímicos, se caracterizaron estructuralmente los principales compuestos aislados y se evaluaron los efectos antioxidantes, diurético, antilitiásico, antiinflamatorio, antimicrobiano y antiparasitario de algunos de sus extractos.
Resultados:
Se establecieron las especificaciones de calidad de las drogas crudas, extractos y formulaciones diseñadas, así como los marcadores químicos. Se pudieron extraer, aislar, purificar y caracterizar algunos de los principales componentes químicos, constituyendo muchos de ellos nuevos reportes para las especies y el género. Se demostraron el potencial bioactivo de las plantas evaluadas y su baja toxicidad. Conclusiones: Las especies estudiadas constituyen un recurso potencial en el campo de los fitoterápicos, ampliando el conocimiento químico-farmacognóstico de la flora cubana y la utilidad terapéutica real de las mismas.
Background
Prostate cancer (PCa) is one of the causes of death in men worldwide. Although treatment strategies have been developed, the recurrence of the disease and consequential side effects remain an essential concern. Diospyros rhodocalyx Kurz, a traditional Thai medicine, exhibits diverse therapeutic properties, including anti-cancer activity. However, its anti-cancer activity against prostate cancer has not been thoroughly explored. This study aims to evaluate the anti-cancer activity and underlying mechanisms of the ethyl acetate extract of D. rhodocalyx Kurz (EADR) related to apoptosis induction in the LNCaP human prostate cancer cell line.
Methods
Ethyl acetate was employed to extract the dried bark of D. rhodocalyx Kurz. The cytotoxicity of EADR on both LNCaP and WPMY-1 cells (normal human prostatic myofibroblast cell line) was evaluated using MTS assay. The effect of EADR on the cell cycle, apoptosis induction, and alteration in mitochondrial membrane potential (MMP) was assessed by the staining with propidium iodide (PI), Annexin V-FITC/PI, and JC-1 dye, respectively. Subsequent analysis was conducted using flow cytometry. The expression of cleaved caspase-3, BAX, and Bcl-2 was examined by Western blotting. The phytochemical profiling of the EADR was performed using gas chromatography-mass spectrometry (GC-MS).
Results
EADR exhibited a dose-dependent manner cytotoxic effect on LNCaP cells, with IC 50 values of 15.43 and 12.35 µg/mL after 24 and 48 h, respectively. Although it also exhibited a cytotoxic effect on WPMY-1 cells, the effect was comparatively lower, with the IC 50 values of 34.61 and 19.93 µg/mL after 24 and 48 h of exposure, respectively. Cell cycle analysis demonstrated that EADR did not induce cell cycle arrest in either LNCaP or WPMY-1 cells. However, it significantly increased the sub-G1 population in LNCaP cells, indicating a potential induction of apoptosis. The Annexin V-FITC/PI staining indicated that EADR significantly induced apoptosis in LNCaP cells. Subsequent investigation into the underlying mechanism of EADR-induced apoptosis revealed a reduction in MMP as evidenced by JC-1 staining. Moreover, Western blotting demonstrated that EADR treatment resulted in the upregulation of BAX, downregulation of BCL-2, and elevation of caspase-3 cleavage in LNCaP cells. Notably, the epilupeol was a prominent compound in EADR as identified by GC-MS.
Conclusion
The EADR exhibits anti-cancer activity against the LNCaP human prostate cancer cell line by inducing cytotoxicity and apoptosis. Our findings suggest that EADR promotes apoptosis by upregulating pro-apoptotic BAX, whereas downregulation of anti-apoptotic Bcl-2 results in the reduction of MMP and the activation of caspase-3. Of particular interest is the presence of epilupeol, a major compound identified in EADR, which may hold promise as a candidate for the development of therapeutic agents for prostate cancer.
Opuntia megarrhiza is an endemic plant used in Mexican traditional medicine for the treatment of bones fractures in humans and domestic animals. One of
the most used technique for the detection and characterization of the structure
of phytochemical compounds is the Gas Chromatography Coupled to Mass Spectrometry. The goals of the present study were to identify and characterize the phytochemical compounds present in wild individuals of O. megarrhiza using this analysis. We used chloroform and methanol extracts from cladodes, and
they were analyzed by gas chromatography-electron impact-mass spectrometry. We obtained 53 phytochemical compounds, 19 have been previously identified with some biological activity. Most of these compounds are alkanes, alkenes, aromatic hydrocarbons, fatty acids, and ketones. We detected some fragmentation patterns that are described for the first time for this species. The variety of metabolites presents in O. megarrhiza justifies the medicinal use of this plant in traditional medicine and highlight it as a source of phytochemical compounds with potential in medicine and biotechnology.
