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1.
Food Chem ; 293: 15-22, 2019 Sep 30.
Artículo en Inglés | MEDLINE | ID: mdl-31151595

RESUMEN

High consumer demand has led global food color manufacturers and food companies to dramatically increase the development and use of natural colors. We have previously reported that avocado (Persea americana) seeds, when crushed in the presence of air, develop a red-orange color in a polyphenol oxidase-dependent reaction. The objective of this study was to identify the major colored compound in colored avocado seed extract (CASE). Column chromatography and high performance liquid chromatography were used to isolate the most abundant colored compound in CASE. This compound, henceforth referred to as perseorangin, was a yellow-orange solid. Structural analysis was performed using high-resolution mass spectrometry, and infrared and nuclear magnetic resonance spectroscopy. We determined that perseorangin is a glycosylated benzotropone-containing compound with a molecular formula of C29H30O14. Liquid chromatography with electrospray ionization mass spectrometry-based metabolomic analysis of CASE and uncolored avocado seed extract showed that perseorangin was unique to CASE.


Asunto(s)
Persea/química , Pigmentos Biológicos/análisis , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Conformación Molecular , Persea/metabolismo , Pigmentos Biológicos/aislamiento & purificación , Extractos Vegetales/química , Análisis de Componente Principal , Semillas/química , Semillas/metabolismo , Espectrometría de Masa por Ionización de Electrospray
2.
J Phys Chem B ; 118(7): 1775-83, 2014 Feb 20.
Artículo en Inglés | MEDLINE | ID: mdl-24432980

RESUMEN

The polymorphic structures of starch were characterized with vibrational sum frequency generation (SFG) spectroscopy. The noncentrosymmetry requirement of SFG spectroscopy allows for the detection of the ordered domains without spectral interferences from the amorphous phase and also the distinction of the symmetric elements among crystalline polymorphs. The V-type amylose was SFG-inactive due to the antiparallel packing of single helices in crystal unit cells, whereas the A- and B-type starches showed strong SFG peaks at 2904 cm(-1) and 2952-2968 cm(-1), which were assigned to CH stretching of the axial methine group in the ring and CH2 stretching of the exocyclic CH2OH side group, respectively. The CH2/CH intensity ratios of the A- and B-type starches are significantly different, indicating that the conformation of hydroxymethyl groups in these two polymorphs may be different. Cyclodextrin inclusion complexes were also analyzed as a comparison to the V-type amylose and showed that the head-to-tail and head-to-head stacking patterns of cyclodextrin molecules govern their SFG signals and peak positions. Although the molecular packing is different between V-type amylose and cyclodextrin inclusion complexes, both crystals show the annihilation of SFG signals when the functional group dipoles are arranged pointing in opposite directions.


Asunto(s)
Análisis Espectral , Almidón/química , Amaranthus , Amilosa/química , Cristalización , Ciclodextrinas/química , Fabaceae , Manihot , Marantaceae , Modelos Moleculares , Estructura Molecular , Oryza , Pisum sativum , Plantas , Solanum tuberosum , Triticum , Vibración , Agua/química , Zea mays
3.
Curr Pharm Des ; 19(34): 6133-40, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23448442

RESUMEN

The pulp of avocado (Persea americana, Lauraceae) has been reported to have beneficial cardiovascular health effects. Avocado oil is used for dermatological applications and its unsaponifiable portion is reported to have beneficial effects against osteoarthritis. Although the seed represents a considerable percentage of the total fruit, scientific research on the phytochemistry and biological effects of avocado seeds is in the nascent stages,. Currently, the seed represents an under-utilized resource and a waste issue for avocado processors. There is ethno-pharmacological information on the use of seeds for the treatment of health-related conditions, especially in South American countries where avocados are endemic and currently grown on a large scale. Current research has shown that avocado seeds may improve hypercholesterolemia, and be useful in the treatment of hypertension, inflammatory conditions and diabetes. Seeds have also been found to possess insecticidal, fungicidal, and anti-microbial activities. The avocado seeds and rich in phenolic compounds, and these may play a role in the putative health effects. Historically, extracts of avocado seeds were also used as ink for writing and research in our laboratory has explored the potential colorant properties of a polyphenol oxidase-produced colored avocado seed extract. Here, we review the currently-available data on the bioactivity and other functional properties of avocado seeds. We discuss the strength of the available data, the putative active compounds, and potential directions for future studies.


Asunto(s)
Persea/química , Extractos Vegetales/farmacología , Polifenoles/farmacología , Semillas/química , Animales , Etnobotánica , Humanos , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Polifenoles/aislamiento & purificación , Polifenoles/toxicidad
4.
J Food Sci ; 76(9): C1335-41, 2011.
Artículo en Inglés | MEDLINE | ID: mdl-22416696

RESUMEN

UNLABELLED: There is an increasing consumer demand for and scientific interest in new natural colorants. Avocado (Persea americana) seed when crushed with water develops an orange color (= 480 nm) in a time-dependent manner. Heat treatment of the seed prevented color development, whereas the addition of exogenous polyphenol oxidase (PPO), but not peroxidase restored color development. Color development was also inhibited by the addition of tropolone, an inhibitor of PPO. Color formation resulted in a decrease in the concentration of polyphenols indicating utilization for color formation. The orange color intensified as the pH was adjusted from 2.0 to 11.0, and these changes were only partially reversible when pH was adjusted from 7.5 to 11.0 in the presence of oxygen, but completely reversible when the pH was changed in the absence of oxygen. The color was found to be stable in solution at -18 °C for 2 mo. These results suggest that the avocado seed may be a potential source of natural colorant, and that color development is PPO-dependent. PRACTICAL APPLICATION: There is growing public and scientific interest in the development of natural alternatives to synthetic colorants in foods. Extracts of turmeric, paprika, and beets are examples of food-derived natural colorants. Avocado seeds, which represent an under-utilized waste stream, form a stable orange color when crushed in the presence of air. Our data indicate that avocado seed represents a potential source of new natural colorants for use in foods.


Asunto(s)
Colorantes de Alimentos/análisis , Colorantes de Alimentos/química , Persea/química , Extractos Vegetales/análisis , Extractos Vegetales/química , Semillas/química , Catecol Oxidasa/metabolismo , Color , Concentración de Iones de Hidrógeno , Polifenoles/análisis
5.
Carbohydr Res ; 337(16): 1467-75, 2002 Sep 09.
Artículo en Inglés | MEDLINE | ID: mdl-12204608

RESUMEN

Complementary analyses of the internal structure of spherulites crystallized from high-amylose maize starch were obtained using light, electron and atomic force microscopy. Radially oriented crystalline lamellae were observed in transmission and scanning electron microscopy, as well as AFM. Internal structures consistent with the central hilum region of starch granules were observed. Spherulites were composed largely of linear or lightly branched starch polymers. Degradation of amylopectin at gelatinization temperatures of 180 degrees C was evident, but iodine binding suggested a high molecular weight (>100 DP) for the spherulitic polymers.


Asunto(s)
Almidón/química , Zea mays/química , Rastreo Diferencial de Calorimetría , Cromatografía en Gel , Cristalización , Geles , Yodo/metabolismo , Microscopía Electrónica de Rastreo/métodos , Microscopía de Polarización , Peso Molecular , Almidón/metabolismo , Almidón/ultraestructura , Zea mays/ultraestructura
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