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1.
J Ethnopharmacol ; 284: 114814, 2022 Feb 10.
Artículo en Inglés | MEDLINE | ID: mdl-34775034

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Hyperglycemia (HG) and lipopolysaccharide (LPS) often promote superoxide accumulation, which may increase oxidative stress. Reducing superoxide production in hyperglycemia and the inflammatory condition is an emerging way to reduce protein and lipid oxidation and diabetes complication. AIM OF STUDY: To examine the effect of Agastache foeniculum essential oil (AFEO) and oil fraction (AFoil) on HG- and LPS-stimulated oxidative stress, the pathogenicity of AFEO and AFoil on oxidative stress was assessed. METHODS: The stimulatory effects of AFEO and AFoil on the activity and expression of NADH oxide (NOX), catalase (CAT), superoxide dismutase (SOD), and the expression of nuclear respiratory factor 2 (NRF2) and nuclear factor-kappa B (NF-kB) in the stimulated macrophage cell line, J774.A1, was studied. The interaction patterns of AFEO and AFoil components with NOX, SOD, CAT, NRF2, and NF-kB proteins were also deduced using molecular docking. RESULTS: Estragole was the main ingredient in AFEO (97%). Linolenic acid (32.10%), estragole (16.22%), palmitic acid (12.62%), linoleic acid (12.04%), and oleic acid (8.73%) were the major chemical components of the AFoil. NOX activation was stimulated in macrophage cells by HG and LPS. At 20 µg/mL, AFEO and AFoil decreased NOX activity while increased SOD and CAT activities in stimulated macrophages. AFoil with estragole and omega-3 fatty acids was better than AFEO with estragole in anti-hyperglycemic and anti-oxidative activity. According to molecular docking research, estragole, linoleic acid, and linolenic acid bind to different hydrophobic pockets of NOX, SOD, CAT, NFR2, and NF-kB using hydrogen bonds, van der Waals bonds, pi-alkyl, and pi-anion interactions, with different binding energies. CONCLUSION: AFEO and AFoil showed antioxidant and anti-diabetic activity. The mechanisms in lowering oxidative stress markers depended on down-regulating superoxide-producing enzymes and up-regulating superoxide-removing enzymes at gene and protein levels. The AFoil emulsion can be used to reduce the detrimental impacts of hyperglycemia and oxidative stress.


Asunto(s)
Agastache/química , Antioxidantes/farmacología , Hipoglucemiantes/farmacología , Aceites Volátiles/farmacología , Aceites de Plantas/farmacología , Derivados de Alilbenceno/química , Derivados de Alilbenceno/farmacología , Animales , Anisoles/química , Anisoles/farmacología , Antioxidantes/química , Catalasa/genética , Catalasa/metabolismo , Línea Celular , Supervivencia Celular/efectos de los fármacos , Regulación de la Expresión Génica/efectos de los fármacos , Glucosa , Hipoglucemiantes/química , Ácido Linoleico/química , Ácido Linoleico/farmacología , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Modelos Moleculares , Complejos Multienzimáticos/química , Complejos Multienzimáticos/metabolismo , NADH NADPH Oxidorreductasas/química , NADH NADPH Oxidorreductasas/metabolismo , Aceites Volátiles/química , Estrés Oxidativo , Aceites de Plantas/química , Conformación Proteica , Superóxido Dismutasa/genética , Superóxido Dismutasa/metabolismo , Ácido alfa-Linolénico/química , Ácido alfa-Linolénico/farmacología
2.
Sci Rep ; 11(1): 23327, 2021 12 02.
Artículo en Inglés | MEDLINE | ID: mdl-34857828

RESUMEN

Pollen selection affects honeybee colony development and productivity. Considering that pollen is consumed by young in-hive bees, and not by foragers, we hypothesized that young bees learn pollen cues and adjust their preferences to the most suitable pollens. To assess whether young bees show preferences based on learning for highly or poorly suitable pollens, we measured consumption preferences for two pure monofloral pollens after the bees had experienced one of them adulterated with a deterrent (amygdalin or quinine) or a phagostimulant (linoleic acid). Preferences were obtained from nurse-aged bees confined in cages and from nurse bees in open colonies. Furthermore, we tested the bees' orientation in a Y-maze using a neutral odour (Linalool or Nonanal) that had been previously associated with an amygdalin-adulterated pollen. Consumption preferences of bees, both in cages and in colonies, were reduced for pollens that had been adulterated with deterrents and increased for pollens that had been supplemented with linoleic acid. In the Y-maze, individuals consistently avoided the odours that they had previously experienced paired with the deterrent-adulterated pollen. Results show that nurse-aged bees associate pollen-based or pollen-related cues with either a distasteful/malaise experience or a tasty/nutritious event, leading to memories that bias their pollen-mediated response.


Asunto(s)
Amigdalina/química , Abejas/fisiología , Conducta Alimentaria/fisiología , Aprendizaje , Ácido Linoleico/química , Néctar de las Plantas/fisiología , Polen/química , Animales , Contaminación de Alimentos/análisis , Polen/efectos de los fármacos
3.
Molecules ; 26(19)2021 Oct 02.
Artículo en Inglés | MEDLINE | ID: mdl-34641538

RESUMEN

Response surface methodology (RSM) with a Box-Behnken design (BBD) was used to optimize the extraction of bioactive compounds from Ephedra fragilis. The results suggested that extraction with 61.93% ethanol at 44.43 °C for 15.84 h was the best solution for this combination of variables. The crude ethanol extract (CEE) obtained under optimum extraction conditions was sequentially fractionated with solvents of increasing polarity. The content of total phenolic (TP) and total flavonoid (TF) as well as the antioxidant and antiglycation activities were measured. The phytochemical fingerprint profile of the fraction with the highest activity was characterized by using RP-HPLC. The ethyl acetate fraction (EAF) had the highest TP and TF contents and exhibited the most potent antioxidant and antiglycation activities. The Pearson correlation analysis results showed that TP and TF contents were highly significantly correlated with the antioxidant and antiglycation activities. Totally, six compounds were identified in the EAF of E. fragilis, including four phenolic acids and two flavonoids. Additionally, molecular docking analysis also showed the possible connection between identified bioactive compounds and their mechanisms of action. Our results suggest new evidence on the antioxidant and antiglycation activities of E. fragilis bioactive compounds that may be applied in the treatment and prevention of aging and glycation-associated complications.


Asunto(s)
Antioxidantes/química , Ephedra/química , Fitoquímicos/química , Fitoquímicos/farmacología , Animales , Bovinos , Fraccionamiento Químico/métodos , Cromatografía Líquida de Alta Presión , Flavonoides/análisis , Flavonoides/aislamiento & purificación , Peróxido de Hidrógeno/química , Ácido Linoleico/química , Reacción de Maillard , Simulación del Acoplamiento Molecular , Fenoles/análisis , Fenoles/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/metabolismo , Extractos Vegetales/química , Reproducibilidad de los Resultados , Albúmina Sérica Bovina/metabolismo , Espectrofotometría Ultravioleta , beta Caroteno/química
4.
Molecules ; 26(17)2021 Aug 27.
Artículo en Inglés | MEDLINE | ID: mdl-34500642

RESUMEN

Currently, the negative effects of unified and intensive agriculture are of growing concern. To mitigate them, the possibilities of using local but nowadays underused crop for food production should be more thoroughly investigated and promoted. The soybean is the major crop cultivated for vegetable oil production in Zambia, while the oil production from local oil-bearing plants is neglected. The chemical composition of oils and cakes of a three traditional oil plant used by descendants of the Lozi people for cooking were investigated. Parinari curatellifolia and Schinziophyton rautanenii oils were chiefly composed of α-eleostearic (28.58-55.96%), linoleic (9.78-40.18%), and oleic acid (15.26-24.07%), whereas Ochna serrulata contained mainly palmitic (35.62-37.31%), oleic (37.31-46.80%), and linoleic acid (10.61-18.66%); the oil yield was high (39-71%). S. rautanenii and O. serrulata oils were rich in γ-tocopherol (3236.18 µg/g, 361.11 µg/g, respectively). The O. serrulata oil also had a very distinctive aroma predominantly composed of p-cymene (52.26%), m-xylene (9.63%), γ-terpinene (9.07%), o-xylene (7.97), and limonene (7.23%). The cakes remaining after oil extraction are a good source of essential minerals, being rich in N, P, S, K, Ca, and Mg. These plants have the potential to be introduced for use in the food, technical, or pharmaceutical industries.


Asunto(s)
Ochnaceae/química , Aceites de Plantas/química , Árboles/química , Culinaria/métodos , Ácidos Grasos/química , Ácido Linoleico/química , Ácido Oléico/química , Semillas/química , Tocoferoles/química , Zambia , gamma-Tocoferol/química
5.
Biomed Res Int ; 2021: 9979419, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34258287

RESUMEN

Nigella sativa (NS) is a well-known plant for its various benefits and multiuse in traditional medicine. This study is aimed at investigating the chemical composition of the different NS fractions by using GC-MS for the esterified fatty acids or HPLC-UV for organic fraction and at evaluating the inhibitory effect on pancreatic α-amylase (in vitro, in vivo) and intestinal glucose absorption. Among all the investigated fractions, it was shown that they are rich with different molecules of great interest. The n-hexane fraction was characterized by the presence of linoleic acid (44.65%), palmitic acid (16.32%), stearic acid (14.60%), and thymoquinone (8.7%), while among the identified peaks in EtOH fraction we found catechin (89.03 mg/100 g DW), rutin (6.46 mg/100 g DW), and kaempferol (0.032 mg/100 g DW). The MeOH fraction was distinguished with the presence of gallic acid (19.91 mg/100 g DW), catechin (13.79 mg/100 g DW), and rutin (21.07 mg/100 g DW). Finally, the aqueous fraction was marked by the existence of different molecules; among them, we mention salicylic acid (32.26 mg/100 g DW), rutin (21.46 mg/100 g DW), and vanillic acid (3.81 mg/100 g DW). Concerning the inhibitory effect on pancreatic α-amylase, it was found that in the in vitro study, the best IC50 registered were those of EtOH (0.25 mg/ml), MeOH (0.10 mg/ml), aqueous (0.031 mg/ml), and n-hexane fraction (0.76 mg/ml), while in the in vivo study an important inhibition of α-amylase in normal and diabetic rats was observed. Finally, the percentage of intestinal glucose absorption was evaluated for all tested extracts and it was ranging from 24.82 to 60.12%. The results of the present study showed that the NS seed fractions exert an interesting inhibitory effect of α-amylase and intestinal glucose absorption activity which could be associated with the existent bioactive compounds. Indeed, these compounds can be used as antidiabetic agents because of their nontoxic effect and high efficacy.


Asunto(s)
Cromatografía Líquida de Alta Presión/métodos , Cromatografía de Gases y Espectrometría de Masas/métodos , Glucosa/farmacocinética , Intestinos/patología , Nigella sativa/metabolismo , Páncreas/enzimología , alfa-Amilasas Pancreáticas/biosíntesis , Animales , Benzoquinonas/química , Diabetes Mellitus Experimental , Femenino , Glucosa/metabolismo , Hipoglucemiantes/farmacología , Concentración 50 Inhibidora , Yeyuno/metabolismo , Ácido Linoleico/química , Masculino , Ratones , Ácido Palmítico/química , Páncreas/efectos de los fármacos , Ratas , Ratas Wistar , Ácidos Esteáricos/química
6.
Molecules ; 26(8)2021 Apr 07.
Artículo en Inglés | MEDLINE | ID: mdl-33917070

RESUMEN

Hair loss by excessive stress from work and lifestyle changes has become a growing concern, particularly among young individuals. However, most drugs for alopecia impose a plethora of side effects. We have found the powerful impact of Malva verticillata seed extracts on alleviating hair loss. This study further isolated effective chemicals in M. verticillata seed extracts by liquid silica gel column chromatography. Under the screening for the growth rate (%) of human follicles dermal papilla cells (HFDPCs), we identified linoleic acid (LA) and oleic acid in n-hexane of M. verticillate (MH)2 fraction. LA treatment activated Wnt/ß-catenin signaling and induced HFDPCs growth by increasing the expression of cell cycle proteins such as cyclin D1 and cyclin-dependent kinase 2. LA treatment also increased several growth factors, such as vascular endothelial growth factor, insulin-like growth factor-1, hepatocyte growth factor, and keratinocyte growth factor, in a dose-dependent manner. Besides, LA significantly inhibited Dickkopf-related protein expression (DKK-1), a primary alopecia signaling by dihydrotestosterone. Our findings suggest that LA treatment may alleviate a testosterone-induced signaling molecule and induces HFDPCs growth by activating Wnt/ß-catenin signaling.


Asunto(s)
Folículo Piloso/citología , Péptidos y Proteínas de Señalización Intercelular/agonistas , Ácido Linoleico/farmacología , Malva/química , Extractos Vegetales/farmacología , Semillas/química , Biomarcadores , Proliferación Celular/efectos de los fármacos , Células Cultivadas , Fraccionamiento Químico , Expresión Génica , Folículo Piloso/metabolismo , Humanos , Péptidos y Proteínas de Señalización Intercelular/genética , Péptidos y Proteínas de Señalización Intercelular/metabolismo , Ácido Linoleico/química , Ácido Linoleico/aislamiento & purificación , Modelos Biológicos , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Vía de Señalización Wnt/efectos de los fármacos
7.
Biomolecules ; 11(4)2021 04 08.
Artículo en Inglés | MEDLINE | ID: mdl-33917892

RESUMEN

The industrial processing amazon fruits, like tucuma, generates a large amount of coproducts with large nutritional potential. Thus, this work obtained the oily extract of the tucuma almonds coproducts by green extraction using palm oil by the ultrasound method and then microencapsulated by atomization and verification of its antioxidant activity. Thermogravimetric techniques, infrared spectroscopy, scanning electron microscopy, moisture content, water activity were applied to characterize the microparticles. Total carotenoids were determined by UV spectroscopy and antioxidant activity was measured by 2,2'-azino-di-(3-ethylbenzthiazoline sulfonic acid and co-oxidation in the system ß-carotene/linoleic acid. The oily extract and microparticle had total carotenoid contents of 3.305 mg/100 g ± 0.01 and 2.559 mg/100 g ± 0.01, respectively. The antioxidant activity assessed through the 2,2'-azino-di-(3-ethylbenzthiazoline sulfonic acid value was 584.75 µM/trolox ± 0.01 (oily extract) and 537.12 µM/trolox ± 0.01 (microparticle) were determined. In the system ß-carotene/linoleic acid showed oxidation of 49.9% ± 1.8 lipophilic extract and 43.3% ± 2.3 microparticle. The results showed that the oily extract of the tucuma almond coproduct can be used as a carotenoid-rich source and microencapsuled with possible application for functional foods production.


Asunto(s)
Antioxidantes/química , Arecaceae/química , Extractos Vegetales/química , Sonicación/métodos , Arecaceae/metabolismo , Rastreo Diferencial de Calorimetría , Carotenoides/análisis , Frutas/química , Frutas/metabolismo , Ácido Linoleico/química , Tamaño de la Partícula , Espectroscopía Infrarroja por Transformada de Fourier , Secado por Pulverización , Termogravimetría , beta Caroteno/química
8.
Eur J Pharm Biopharm ; 162: 43-49, 2021 May.
Artículo en Inglés | MEDLINE | ID: mdl-33677067

RESUMEN

Lipid-based formulations play a significant role in oral delivery of lipophilic drugs. Previous studies have shown that natural sesame oil promotes the intestinal lymphatic transport and oral bioavailability of the highly lipophilic drug cannabidiol (CBD). However, both lymphatic transport and systemic bioavailability were also associated with considerable variability. The aim of this study was to test the hypothesis that pre-digested lipid formulations (oleic acid, linoleic acid, oleic acid with 2-oleoylglycerol, oleic acid with 2-oleoylglycerol and oleic acid with glycerol) could reduce variability and increase the extent of the intestinal lymphatic transport and oral bioavailability of CBD. The in vivo studies in rats showed that pre-digested or purified triglyceride did not improve the lymphatic transport and bioavailability of CBD in comparison to sesame oil. Moreover, the results suggest that both the absorption of lipids and the absorption of co-administered CBD were more efficient following administration of natural sesame oil vehicle compared with pre-digested lipids or purified trioleate. Although multiple small molecule constituents and unique fatty acid compositions could potentially contribute to a better performance of sesame oil in oral absorption of lipids or CBD, further investigation will be needed to identify the mechanisms involved.


Asunto(s)
Cannabidiol/farmacocinética , Composición de Medicamentos/métodos , Excipientes/química , Absorción Intestinal , Aceite de Sésamo/química , Administración Oral , Animales , Área Bajo la Curva , Disponibilidad Biológica , Cannabidiol/administración & dosificación , Cannabidiol/química , Mucosa Intestinal/metabolismo , Ácido Linoleico/química , Vasos Linfáticos/metabolismo , Masculino , Modelos Animales , Ácido Oléico/química , Ratas , Distribución Tisular , Trioleína/química
9.
J Photochem Photobiol B ; 216: 112151, 2021 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-33581679

RESUMEN

Photochemoprotection of the skin can be achieved by inhibiting inflammation and oxidative stress, which we tested using Cordia verbenacea extract, a medicinal plant known for its rich content of antioxidant molecules and anti-inflammatory activity. In vitro antioxidant evaluation of Cordia verbenacea leaves ethanolic extract (CVE) presented the following results: ferric reducing antioxidant power (886.32 µM equivalent of Trolox/g extract); IC50 of 19.128 µg/ml for scavenging 2,2-diphenyl-1-picrylhydrazyl; IC50 of 12.48 µg/mL for scavenging 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid); decrease of hydroperoxides from linoleic acid (IC50 of 10.20 µg/mL); inhibition of thiobarbituric acid reactive substances (IC50 8.90 µg/mL); iron-chelating ability in bathophenanthroline iron assay (IC50 47.35 µg/mL); chemiluminescence triggered by free radicals in the H2O2/horseradish peroxidase/luminol (IC50 0.286 µg/mL) and xanthine/xanthine oxidase/luminol (IC50 0.42 µg/mL) methods. CVE (10-100 mg per kg, 30 min before and immediately after UVB exposure) treatment was performed by gavage in hairless mice. CVE inhibited skin edema, neutrophil infiltration, and overproduction of MMP-9; reduced levels of TNF-α, IL-1ß, and IL- 6; numbers of skin mast cells, epidermal thickening, number of epidermal apoptotic keratinocytes, and collagen degradation. CVE increased the skin's natural antioxidant defenses as observed by Nrf-2, NAD(P)H quinone oxidoreductase 1, and heme oxygenase 1 mRNA expression enhancement. Furthermore, CVE inhibited lipid peroxidation and superoxide anion production and recovered antioxidant reduced glutathione, catalase activity, and ROS scavenging capacity of the skin. Concluding, CVE downregulates the skin inflammatory and oxidative damages triggered by UVB, demonstrating its potentialities as a therapeutic approach.


Asunto(s)
Antiinflamatorios/química , Antioxidantes/química , Cordia/química , Extractos Vegetales/química , Hojas de la Planta/química , Sustancias Protectoras/química , Animales , Antiinflamatorios/farmacología , Antioxidantes/farmacología , Citocinas/metabolismo , Edema/metabolismo , Femenino , Hemo-Oxigenasa 1/metabolismo , Humanos , Peróxido de Hidrógeno/química , Ácido Linoleico/química , Peroxidación de Lípido , Ratones Pelados , Factor 2 Relacionado con NF-E2/metabolismo , Estrés Oxidativo/efectos de los fármacos , Estrés Oxidativo/efectos de la radiación , Extractos Vegetales/farmacología , Sustancias Protectoras/farmacología , Quinona Reductasas/metabolismo , Piel/efectos de la radiación , Superóxidos/metabolismo , Rayos Ultravioleta
10.
J Oleo Sci ; 70(2): 165-173, 2021 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-33455999

RESUMEN

The lipid products that consist of structured lipids rich in palmitic acid (16:0) at the sn-2 position of triacylglycerol (TAG) and rich in low-unsaturated fatty acids (FAs) (LUFAs), such as oleic acid; 18:1 and linoleic acid; 18:2 at the sn-1(3) positions, are useful intermediates for manufacturing human milk fat substitute (HMFS), which contains functional lipid components. In this study, the HMFS intermediate (HMFS-IM) was enzymatically prepared from palm oil without using other oil sources. First, the amount of 16:0 at the sn-2 position of TAG substrate was enhanced from 18.9% to more 34.5% via a random esterification reaction using a non-stereospecific lipase, Novozym® 435, to produce a random-palm substrate. Consequently, 2-monoacylglycerol (2-MAG) rich in 16:0 at the sn-2 position over 88%, together with the FA ethyl ester substrates rich in LUFAs, such as 18:1-Et and 18:2-Et above 93.5% was prepared through ethanolysis reaction using the same lipase from the random-palm substrate and by purification with urea complexation, respectively. As the preferred modified method, a continuous use of the same lipase to these reactions were achieved while reducing the usage of enzyme to half. Finally, an HMFS-IM rich in 16:0 at the sn-2 position more than 60% and LUFA at sn-1(3) positions was prepared using these palm oil-based products, including random-palm, palm-Et, and 2-MAG, via the interesterification reaction using a 1,3-stereospecific lipase, Lipozyme® RM-IM. Thus, HMFS-IM was successfully prepared by palm oil materials with a 65 wt% usage ratio. The concept described in this study will be useful for HMFS manufacturing from a single natural oil substrate, which is not initially rich in 16:0 at the sn-2 position.


Asunto(s)
Ácidos Grasos Insaturados/química , Glucolípidos/química , Glicoproteínas/química , Gotas Lipídicas/química , Sustitutos de la Leche/síntesis química , Leche Humana/química , Aceite de Palma/química , Ácido Palmítico/química , Enzimas Inmovilizadas , Esterificación , Proteínas Fúngicas , Ácido Linoleico/química , Lipasa/química , Ácido Oléico/química , Triglicéridos/química
11.
Int J Mol Sci ; 21(24)2020 Dec 17.
Artículo en Inglés | MEDLINE | ID: mdl-33348841

RESUMEN

The aim of the available literature review was to focus on the role of the proinflammatory mediators of AA and LA derivatives in pathological conditions related to reproduction and pregnancy. Arachidonic (AA) and linoleic acid (LA) derivatives play important roles in human fertility and the course of pathological pregnancies. Recent studies have demonstrated that uncontrolled inflammation has a significant impact on reproduction, spermatogenesis, endometriosis, polycystic ovary syndrome (PCOS) genesis, implantation, pregnancy and labor. In addition, cyclooxygenase-mediated prostaglandins and AA metabolite levels are higher in women's ovarian tissue when suffering from PCOS. It has been demonstrated that abnormal cyclooxygenase-2 (COX-2) levels are associated with ovulation failure, infertility, and implantation disorders and the increase in 9-HODE/13-HODE was a feature recognized in PCOS patients. Maintaining inflammation without neutrophil participation allows pregnant women to tolerate the fetus, while excessive inflammatory activation may lead to miscarriages and other pathological complications in pregnancies. Additionally AA and LA derivatives play an important role in pregnancy pathologies, e.g., gestational diabetes mellitus, preeclampsia (PE), and fetal growth, among others. The pathogenesis of PE and other pathological states in pregnancy involving eicosanoids have not been fully identified. A significant expression of 15-LOX-1,2 was found in women with PE, leading to an increase in the synthesis of AA and LA derivatives, such as hydroxyeicozatetraenoic acids (HETE) and hydroxyoctadecadiene acids (HODE). Synthesis of the metabolites 5-, 8-, 12-, and 15-HETE increased in the placenta, while 20-HETE increased only in umbilical cord blood in women with preeclampsia compared to normal pregnancies. In obese women with gestational diabetes mellitus (GDM) an increase in epoxygenase products in the cytochrome P450 (CYP) and the level of 20-HETE associated with the occurrence of insulin resistance (IR) were found. In addition, 12- and 20-HETE levels were associated with arterial vasoconstriction and epoxyeicosatrienoic acids (EETs) with arterial vasodilatation and uterine relaxation. Furthermore, higher levels of 5- and 15-HETE were associated with premature labor. By analyzing the influence of free fatty acids (FFA) and their derivatives on male reproduction, it was found that an increase in the AA in semen reduces its amount and the ratio of omega-6 to omega-3 fatty acids showed higher values in infertile men compared to the fertile control group. There are several studies on the role of HETE/HODE in relation to male fertility. 15-Hydroperoxyeicosatetraenoic acid may affect the integrity of the membrane and sperm function. Moreover, the incubation of sperm with physiologically low levels of prostaglandins (PGE2/PGF2α) improves the functionality of human sperm. Undoubtedly, these problems are still insufficiently understood and require further research. However, HETE and HODE could serve as predictive and diagnostic biomarkers for pregnancy pathologies (especially in women with risk factors for overweight and obesity). Such knowledge may be helpful in finding new treatment strategies for infertility and the course of high-risk pregnancies.


Asunto(s)
Ácido Araquidónico/metabolismo , Ácido Linoleico/metabolismo , Complicaciones del Embarazo/fisiopatología , Reproducción , Ácido Araquidónico/química , Femenino , Humanos , Ácido Linoleico/química , Embarazo
12.
Molecules ; 25(19)2020 Oct 06.
Artículo en Inglés | MEDLINE | ID: mdl-33036316

RESUMEN

This investigation included the chemical analysis of Peganum harmala (P. harmala) seed oil and its antifungal properties against 10 fungal species. Seed oils of six populations were analyzed using high performance liquid chromatography (HPLC) and gas chromatograph/mass spectrometry (GC-MS). The HPLC analysis indicated that P. harmala seed oil exhibited a very high level of tocopherol contents, with values in the range of 2385.66-2722.68 mg/100 g. The most abundant tocopherol isomer was δ-tocopherol (90.39%), followed by γ-tocopherol (8.08%) and α-tocopherol (1.14%). We discovered for the first time the presence of tocotrenols in P. harmala seed oils of the six populations studied. The GC-MS analyses revealed that linoleic acid was the main fatty acid (65.17%), followed by oleic acid (23.12%), palmitic acid (5.36%) and stearic acid (3.08%). We also studied the antifungal activity of seed oil of the Medenine (MD) population on ten fungal pathogens. The antifungal effects differed among pathogens and depended on oil concentrations. Seed oil of the MD population caused a significant decrease in mycelial growth of all fungi tested, with values ranging 31.50-82.11%, except for Alternaria sp., which showed no inhibition. The antifungal activity against the 10 selected fungi can be explained by the richness in tocols of the extracted oil and make P. harmala a promising crop for biological control. Furthermore, the importance of fatty acids and the wide geographic spread in Tunisia of this species make this crop a potential source of renewable energy.


Asunto(s)
Antifúngicos/química , Antifúngicos/farmacología , Peganum/química , Aceites de Plantas/química , Aceites de Plantas/farmacología , Semillas/química , Tocoferoles/química , Tocoferoles/farmacología , Hongos/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas , Ácido Linoleico/química , Ácido Linoleico/farmacología , Ácido Oléico/química , Ácido Oléico/farmacología , Ácido Palmítico/química , Ácido Palmítico/farmacología
13.
J Oleo Sci ; 69(10): 1191-1198, 2020 Oct 07.
Artículo en Inglés | MEDLINE | ID: mdl-32908091

RESUMEN

The kinetics of catalytic transfer hydrogenation (CTH) of low-erucic-acid rapeseed oil using ammonium formate as a hydrogen donor over a Ni-Ag0.15/SBA15 catalyst were studied. Then, a kinetic model for the hydrogenation of low-erucic-acid rapeseed oil was established, and it was found that the reaction rate constants of hydrogenations of 9c-18:1 and 12c-18:1 oleic acid were 0.1262 and 0.0148, and the catalytic selectivity of linoleic acid was 2.04. For the catalyst loading of 0.23%, the hydrogenation temperature was 80°C, the ammonium formate concentration was 0.32 mol/50 mL, and the low-erucic-acid rapeseed oil was hydrogenated in 90 min; it was also found that the iodine value of low-erucic-acid rapeseed oil was 80 g I2/100 g, the oleic acid content was 65%, and the trans fatty acids (TFAs) content was only 6.7%. Therefore, CTH may be widely used in the modification of oils and fats.


Asunto(s)
Ácidos Erucicos , Cinética , Níquel/química , Aceite de Brassica napus/química , Plata/química , Catálisis , Formiatos/química , Calor , Hidrogenación , Yodo/análisis , Ácido Linoleico/análisis , Ácido Linoleico/química , Ácido Oléico/análisis , Ácido Oléico/química , Ácidos Grasos trans/análisis
14.
Enzyme Microb Technol ; 139: 109581, 2020 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-32732030

RESUMEN

Ergosterol, like cholesterol, has many beneficial physiological activities, and because it has no adverse clinical problem with cholesterol, it is a substance that can be used as a biomaterial in the food and cosmetics industry. However, ergosterol has low oil solubility and is easily crystallized, which is problematic for its direct use in the industry. This problem can be solved by combining fatty acids with ergosterol. In this study, ergosterol derivatives with unsaturated fatty acids were synthesized from ergosterol and various plant oils. Specifically, ergosterol oleate (EO), ergosterol linoleate (EL), and ergosterol linolenate (ELn) were synthesized using Proteus vulgaris K80 lipase. To effectively synthesize these unsaturated fatty acid ergosterol esters (FAEEs), 25 mM ergosterol and 40 mM plant oil were added into hexane solvent, and transesterification reaction was performed at 40 °C. Proteus vulgaris K80 lipase showed higher conversion yield than other commercial lipases, due to its high affinity to ergosterol and broad substrate specificity. Rapeseed oil, sunflower seed oil, and linseed oil were used to synthesize EO, EL, and ELn, respectively. The FAEEs were purified, and their purity was confirmed by FT-IR and LC-MS. The solubility of the FAEEs in a tricaprylin solvent was increased 11-16 times, compared to that of ergosterol. We found that EL- and ELn-containing emulsions had strong growth inhibitory activity against some dairy and cosmetic spoilage bacteria.


Asunto(s)
Bacterias/efectos de los fármacos , Ergosterol/farmacología , Ácidos Grasos Insaturados/farmacología , Lipasa/metabolismo , Aceites de Plantas/química , Bacterias/clasificación , Emulsiones , Esterificación , Ácidos Grasos Insaturados/química , Ácido Linoleico/química , Especificidad por Sustrato
15.
Curr Top Med Chem ; 20(22): 1981-1992, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32703136

RESUMEN

AIMS: The aim of this study is to explore essential oil from the bark of Cedrus deodara (CDEO) as an potential anticancer agent. BACKGROUND: The frontline drugs against cancer in clinical settings are posing challenges of resistance and other detrimental side-effects. This has led to the exploration of new anticancer chemical entities from natural sources, particularly plant-based products such as essential oils that serve as vast repositories of pharmacologically active substances for combating cancer. OBJECTIVE: The objective is to isolate and characterize the essential oil from the bark of Cedrus deodara (CDEO) and evaluate its potential as an anticancer agent and delineate the possible underlying mechanism of action. METHODS: Cedrus deodara essential oil from bark (CDEO) was obtained by hydro-distillation and analyzed by GC/MS for vital constituents. Further, in vitro cytotoxic potential was measured by MTT assay against a panel of cancer cell lines. The apoptosis-inducing potential of CDEO was analyzed by mitochondrial membrane potential loss (ΔΨm) and nuclear fragmentation assay. Besides, wound healing assay and colonogenic assay were employed to check the anti-metastatic potential of CDEO. Molecular docking approaches were employed for target identification, while immuno-blotting was carried out for target validation. RESULTS AND DISCUSSION: The major components identified were 2-(tert-Buyl)-6-methyl-3-(2- (trifluoromethyl) benzyl)imidazo [1,2-a]pyridine (26.32 %);9- Octadecenoic acid (8.015 %); Copaene (5.181 %);2-(4-Methoxy-2,6-dimethylphenyl) -3-methyl-2H- benzo[g]indazole(4.36 %) and 9(E),11(E)- Conjugated linoleic acid (4.299 %). Further, potent in vitro cytotoxic activity with IC50 values of 11.88 µg/ ml and 14.63 µg/ ml in colon cancer cell lines of HCT-116 and SW-620, respectively. Further, a significant and dose-dependent decrease in colony formation, cell migration, induction of ROS formation and loss in ΔΨm was observed. Additionally, major compounds identified were chosen for ligandprotein binding interaction studies to predict the molecular targets in colon cancer. It was observed that compounds such as 9-Octadecenoic acid;4H-1- Benzopyran-4-one, 3-(3,4-dimethoxyphenyl)-6,7- dimethoxy; 2-(4-Methoxy-2,6-dimethylphenyl) -3-methyl-2H-benzo [g]indazole and 2-Bornanol,5-(2,4- dinitro phenyl) hydrazono have a prominent binding affinity with NF-κB. This was also further validated by immuno-blotting results wherein CDEO treatment in colon cancer cells led to the abrogation of NFκB, and the Bcl-2-associated X protein (Bax): B-cell lymphoma (Bcl)-2 ratio was up-regulated leading to enhanced cleaved caspase 3 formation and subsequent apoptosis. CONCLUSION: These results unveil CDEO inhibits cell proliferation and induces apoptosis in colon cancer cells, which can be attributed to the abrogation of the NFκB signaling pathway.


Asunto(s)
Antineoplásicos/química , Cedrus/química , Neoplasias del Colon/tratamiento farmacológico , FN-kappa B/antagonistas & inhibidores , Aceites Volátiles/química , Corteza de la Planta/química , Extractos Vegetales/química , Antineoplásicos/farmacología , Apoptosis/efectos de los fármacos , Caspasa 3/metabolismo , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Ácido Linoleico/química , Simulación del Acoplamiento Molecular , Aceites Volátiles/farmacología , Extractos Vegetales/farmacología , Aceites de Plantas/química , Unión Proteica , Especies Reactivas de Oxígeno/metabolismo , Ácidos Esteáricos/química , Relación Estructura-Actividad
16.
Molecules ; 25(11)2020 May 31.
Artículo en Inglés | MEDLINE | ID: mdl-32486338

RESUMEN

This study investigated the effect of blanching pomegranate seeds (PS) on oil yield, refractive index (RI), yellowness index (YI), conjugated dienes (K232), conjugated trienes (K270), total carotenoid content (TCC), total phenolic compounds (TPC) and DPPH radical scavenging of the extracted oil. Furthermore, phytosterol and fatty acid compositions of the oil extracted under optimum blanching conditions were compared with those from the oil extracted from unblanched PS. Three different blanching temperature levels (80, 90, and 100 °C) were studied at a constant blanching time of 3 min. The blanching time was then increased to 5 min at the established optimum blanching temperature (90 °C). Blanching PS increased oil yield, K232, K270, stigmasterol, punicic acid, TPC and DPPH radical scavenging, whereas YI, ß-sitosterol, palmitic acid and linoleic acid were decreased. The RI, TCC, brassicasterol, stearic acid, oleic acid and arachidic acid of the extracted oil were not significantly (p > 0.05) affected by blanching. Blanching PS at 90 °C for 3 to 5 min was associated with oil yield, TPC and DPPH. Blanching PS at 90 °C for 3 to 5 min will not only increase oil yield but could also improve functional properties such as antioxidant activity, which are desirable in the cosmetic, pharmaceutical, nutraceutical and food industries.


Asunto(s)
Antioxidantes/química , Carotenoides/química , Aceites de Plantas/química , Granada (Fruta)/química , Semillas/química , Compuestos de Bifenilo/química , Colestadienoles/química , Suplementos Dietéticos , Ácidos Eicosanoicos/química , Ácidos Grasos/química , Tecnología de Alimentos , Depuradores de Radicales Libres/química , Ácido Linoleico/química , Ácidos Linolénicos/química , Ácido Oléico/química , Fenol/química , Fenoles/química , Fitosteroles/química , Picratos/química , Refractometría , Ácidos Esteáricos/química , Temperatura
17.
Molecules ; 25(10)2020 May 17.
Artículo en Inglés | MEDLINE | ID: mdl-32429512

RESUMEN

The interaction of drugs with human serum albumin (HSA) is an important element of therapy. Albumin affects the distribution of the drug substance in the body, as well as its pharmacokinetic and pharmacodynamic properties. On the one hand, inflammation and protein glycation, directly associated with many pathological conditions and old age, can cause structural and functional modification of HSA, causing binding disorders. On the other hand, the widespread availability of various dietary supplements that affect the content of fatty acids in the body means that knowledge of the binding activity of transporting proteins, especially in people with chronic diseases, e.g., diabetes, will achieve satisfactory results of the selected therapy. Therefore, the aim of the present study was to evaluate the effect of a mixture of fatty acids (FA) with different saturated and unsaturated acids on the affinity of acetohexamide (AH), a drug with hypoglycaemic activity for glycated albumin, simulating the state of diabetes in the body. Based on fluorescence studies, we can conclude that the presence of both saturated and unsaturated FA disturbs the binding of AH to glycated albumin. Acetohexamide binds more strongly to defatted albumin than to albumin in the presence of fatty acids. The competitive binding of AH and FA to albumin may influence the concentration of free drug fraction and thus its therapeutic effect.


Asunto(s)
Acetohexamida/química , Ácidos Grasos/química , Hipoglucemiantes/química , Albúmina Sérica Humana/química , Albúmina Sérica/química , Unión Competitiva , Glucosa/química , Productos Finales de Glicación Avanzada , Humanos , Ácido Linoleico/química , Simulación de Dinámica Molecular , Ácido Mirístico/química , Ácido Oléico/química , Ácido Palmítico/química , Unión Proteica , Conformación Proteica , Soluciones , Albúmina Sérica Glicada
18.
Molecules ; 25(4)2020 Feb 22.
Artículo en Inglés | MEDLINE | ID: mdl-32098445

RESUMEN

Positive physiological benefits of several plant oils on the UV-induced photoaging have been reported in some cell lines and model mice, but perilla oil collected from the seeds of Perilla frutescens L. has not been investigated in this context. To study the therapeutic effects of cold-pressed perilla oil (CPO) on UV-induced photoaging in vitro and in vivo, UV-induced cellular damage and cutaneous photoaging were assessed in normal human dermal fibroblasts (NHDFs) and HR-1 hairless mice. CPO contained five major fatty acids including linolenic acid (64.11%), oleic acid (16.34%), linoleic acid (11.87%), palmitic acid (5.06%), and stearic acid (2.48%). UV-induced reductions in NHDF cell viability, ROS production, SOD activity, and G2/M cell cycle arrest were remarkably improved in UV + CPO treated NHDF cells as compared with UV + Vehicle treated controls. Also, UV-induced increases in MMP-1 protein and galactosidase levels were remarkably suppressed by CPO. In UV-radiated hairless mice, topical application of CPO inhibited an increase in wrinkle formation, transepidermal water loss (TEWL), erythema value, hydration and melanin index on dorsal skin of UVB-irradiated hairless mice. CPO was observed to similarly suppress UV-induced increases in epidermal thickness, mast cell numbers, and galactosidase and MMP-3 mRNA levels. These results suggest CPO has therapeutic potential in terms of protecting against skin photoaging by regulating skin morphology, histopathology and oxidative status.


Asunto(s)
Extractos Vegetales/farmacología , Envejecimiento de la Piel/efectos de los fármacos , Piel/efectos de los fármacos , Ácido alfa-Linolénico/farmacología , Animales , Antioxidantes , Fibroblastos/efectos de los fármacos , Humanos , Ácido Linoleico/química , Ácido Linoleico/farmacología , Ratones , Ratones Pelados , Ácido Oléico/química , Ácido Oléico/farmacología , Perilla frutescens , Extractos Vegetales/química , Aceites de Plantas/química , Aceites de Plantas/farmacología , Piel/patología , Piel/efectos de la radiación , Envejecimiento de la Piel/patología , Envejecimiento de la Piel/efectos de la radiación , Rayos Ultravioleta/efectos adversos , Ácido alfa-Linolénico/química
19.
Molecules ; 25(4)2020 Feb 16.
Artículo en Inglés | MEDLINE | ID: mdl-32079080

RESUMEN

In the last decade, there has been growing interest in the food industry in replacing synthetic chemicals with natural products with bioactive properties. This study's aims were to determine the chemical composition and the antioxidant properties of the essential oil of Pastianica sylvestris. The essential oil was isolated with a yield of 0.41% (w/v) by steam distillation from the dried seeds and subsequently analysed by GC-MS. Octyl acetate (78.49%) and octyl hexanoate (6.68%) were the main components. The essential oil exhibited an excellent activity for the inhibition of primary and secondary oxidation products for cold-pressed sunflower oil comparable with butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT), which were evaluated using peroxide and thiobarbituric acid values. The antioxidant activity of the essential oil was additionally validated using DPPH radical scavenging (0.0016 ± 0.0885 mg/mL), and ß-carotene-linoleic acid bleaching assays. Also, the amounts of total phenol components (0.0053 ± 0.0023 mg GAE/g) were determined.


Asunto(s)
Acetatos/química , Antioxidantes/química , Aceites Volátiles/química , Pastinaca/química , Semillas/química , Acetatos/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Bioensayo , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Hidroxianisol Butilado/química , Hidroxianisol Butilado/aislamiento & purificación , Hidroxitolueno Butilado/química , Cromatografía de Gases y Espectrometría de Masas , Ácido Linoleico/química , Aceites Volátiles/aislamiento & purificación , Fenoles/química , Picratos/antagonistas & inhibidores , Picratos/química , Extractos Vegetales/química , Aceite de Girasol/química , Tiobarbitúricos/química , beta Caroteno/química
20.
Phytother Res ; 34(2): 254-269, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31657094

RESUMEN

The use of vegetable butters and oils shows promising results in the treatment of skin wounds, as they have an effective impact on the phases of the wound-healing process through their antimicrobial, anti-inflammatory, and antioxidative activities and by promoting cell proliferation, increasing collagen synthesis, stimulating dermal reconstruction, and repairing the skin's lipid barrier function. In this article, in vitro and in vivo studies of argan (Argania spinosa), avocado (Persea americana), black cumin (Nigella sativa), calophyllum (Calophyllum inophyllum), coconut (Cocos nucifera), cranberry (Vaccinium macrocarpon), grape (Vitis vinifera), green coffee (Coffea arabica), lentisk (Pistacia lentiscus), linseed (Linum usitatissimum), lucuma (Pouteria lucuma), mango (Mangifera indica), olive (Olea europaea), pomegranate (Punica granatum), pumpkin (Cucurbita pepo), rapeseed (Brassica napus), sea buckthorn (Hippophae rhamnoides), and sunflower (Helianthus annuus) oils were reviewed. In many cases, vegetable oils proved to be more effective than synthetic wound-healing compounds used as controls. The fatty-acid components of vegetable oils are assumed to play a major role in the wound-healing process, in particular polyunsaturated fatty acids such as linoleic acid. Evidence shows that oils with a higher linoleic to oleic acid ratio are more effective for lipid barrier repair. However, in depth studies are needed to gain knowledge about vegetable oils' effects on the skin and vice versa.


Asunto(s)
Aceites de Plantas/farmacología , Cicatrización de Heridas , Administración Cutánea , Animales , Calophyllum , Cucurbita , Dermatología , Ácidos Grasos/química , Lino , Humanos , Ácido Linoleico/química , Aceite de Linaza , Mangifera , Ácido Oléico/química , Persea , Piel , Enfermedades de la Piel , Vaccinium macrocarpon , Verduras
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