Pouteria lucuma Pulp and Skin: In Depth Chemical Profile and Evaluation of Antioxidant Activity.

Pouteria lucuma Ruiz and Pav., known as the 'Gold of the Incas' or 'lucuma', is a subtropical fruit belonging to the Sapotaceae family, with a very sweet flavor, used to prepare cakes, ice creams as well as in the baking and dairy industries. To date, the content of primary metabolites is known, but little information is reported about the composition in specialized metabolites. Moreover, no study is reported on skin which represent an important agricultural waste due to the high demand for lucuma. In order to have a preliminary metabolite profile of Pouteria lucuma, the extracts of pulp and skin have been analyzed by LC-ESI/LTQOrbitrap/MS/MS in negative ion mode. The careful analysis of the accurate masses, of the molecular formulas and of the ESI/MS spectra allowed to identify specialized metabolites belonging to phenolic, flavonoid and polar lipid classes. The LC-MS/MS analysis guided the isolation of compounds occurring in the pulp extract whose structures have been characterized by spectroscopic methods including 1D- and 2D-NMR experiments and ESI-MS analysis. Furthermore, the phenolic content of the extracts along with the antioxidant activity of extracts and isolated compounds was evaluated.

Isolation and identification of sapotexanthin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).

Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-performance liquid chromatography-electronic circular dichroism (HPLC-ECD) analysis. Spectroscopic data of the natural and semisynthetic derivatives obtained by acid-catalyzed rearrangement of cryptocapsin 5,8-epoxide stereoisomers were compared for structural elucidation.

Pouteria ramiflora (Mart.) Radlk. extract: Flavonoids quantification and chemopreventive effect on HepG2 cells.

Pouteria ramiflora (Mart.) Radlk., popularly known as curriola, is commonly used in Brazil as medicinal plant to treat worm infections, dysentery, pain, inflammation, hyperlipidemia, and obesity. At present the safety of this extract when used therapeutically in human remains to be determined. Thus, the aim of this study was to examine cytotoxicity, antiproliferative, and antimutagenic actions of this extract. The hydroalcoholic extract from P. ramiflora leaves consisted of flavonoids identified and quantified as myricetin-3-O-ß-D-galactopyranoside (13.55 mg/g) and myricetin-3-O-α-L-rhamnopyranoside (9.61 mg/g). The extract exhibited cytotoxicity at concentrations higher than 1.5 µg/ml in human hepatocarcinoma (HepG2)and 2.5 µg/ml in non-tumoral primary gastric (GAS) cells using the MTT assay, and at concentrations higher than 3 µg/ml in HepG2 and 3.5 µg/ml in GAS cells by the neutral red assay. The extract did not show antiproliferative effect as evidenced by the nuclear division index (NDI). However, in the presence of benzo[a]pyrene (BaP) (positive control), an enhanced cytostatic effect in the NDI and flow cytometry was noted. It is of interest that when the extract was co-incubated with BaP a significant decrease in DNA damage was observed indicating an antimutagenic action. This protective effect might be attributed to myricetin and gallic acid found in P. ramiflora extract. The low cytotoxicity action and protective effect observed in the present study encourage further studies regarding other biological effects of P. ramiflora, as well as its potential use as a chemopreventive agent.

Antinociceptive and Antihyperalgesic Activity of a Traditional Maya Herbal Preparation Composed of Pouteria Campechiana, Chrysophyllum Cainito, Citrus Limonum, and Annona Muricata.

Preclinical Research The purpose of this work was to assess the antinociceptive and antihyperalgesic properties of an herbal preparation, composed of four vegetal species: Pouteria campechiana (P. campechiana), Chrysophyllum cainito (C. cainito), Citrus limonum (C. limonum), and Annona muricata (A. muricata), that is commonly used in combination (PCCA) in traditional Mayan medicine for the treatment of diabetes and pain. An ethanolic extract of PCCA was prepared at a ratio of 1:1:1:1 for each plant. The systemic antinociceptive effect of PCCA extract (50-600 mg/kg, p.o.) was dose-dependent in the rat formalin (1%) producing 66% antinociceptive response at 400 mg/kg, p.o. A concentration-dependent antinociceptive effect of the PCCA extract (20-160 mg/paw) was also demonstrated in the rat capsaicin (0.2%) test. The PCCA extract (100-400 mg/kg, p.o.) had antihyperalgesic effects in alloxan diabetic rats. These findings demonstrate the antinociceptive and antihyperalgesic effects of PCCA and supports the use of the plant extracts in Mayan folk medicine. Drug Dev Res 78 : 91-97, 2017. © 2017 Wiley Periodicals, Inc.

Activity of crude extracts from Brazilian cerrado plants against clinically relevant Candida species.

BACKGROUND: Medicinal plants have traditionally been used in many parts of the world as alternative medicine. Many extracts and essential oils isolated from plants have disclosed biological activity, justifying the investigation of their potential antimicrobial activity. In this study, the in vitro antifungal activity of six Brazilian Cerrado medicinal plant species were evaluated against clinically relevant Candida species. METHODS: The crude extract plants were evaluated against American Type Culture Collection (ATCC) standard strains of Candida spp. using disk diffusion method and determining the minimum inhibitory concentration (MIC). The chemical study results were confirmed by HPLC method. RESULTS: All six plant species showed antifungal activity. Among the species studied, Eugenia dysenterica and Pouteria ramiflora showed significant inhibitory activity against C. tropicalis at lowest MIC value of 125 and 500 µg/disc, respectively. The Eugenia dysenterica also disclosed MIC value of 125 µg/disc against C. famata, 250 µg/disc against C. krusei and 500 µg/disc against C. guilliermondii and C. parapsilosis. Pouteria torta, Bauhinia rufa, Erythroxylum daphnites and Erythroxylum subrotundum showed activity against the yeast strains with MIC value of 1000 µg/disc. The chemical study of the most bioactive extracts of Eugenia dysenterica and Pouteria ramiflora revealed catechin derivatives and flavonoids as main components. CONCLUSIONS: All six evaluated plant species showed good antifungal potential against several Candida strains. However, E .dysenterica and P. ramiflora showed the higher inhibitory effect against the non-albicans Candida species. Our results may contribute to the continuing search of new natural occurring products with antifungal activity.

Acute Toxicity and Dermal and Eye Irritation of the Aqueous and Hydroalcoholic Extracts of the Seeds of "Zapote" Pouteria mammosa (L.) Cronquist.

The common use of Pouteria mammosa (L.) Cronquist, "Mamey or Zapote," in food and ethnobotanic medicine shows its low or absent toxicity as fruit extracts prepared from seeds. However, it is essential to conduct security trials to scientifically support their use in drug therapy. This study evaluated the aqueous and hydroalcoholic extract (25%) Acute Oral Toxicity, obtained from the seeds of P. mammosa, in Sprague Dawley rats and dermal and eye irritability in New Zealand rabbits. The 404 and 405 acute dermal and eye irritation/corrosion guidelines were used, as well as the 423 Acute Oral Toxicity guideline, Acute Toxic Class Method of the Organization for Economic Cooperation and Development (OECD). The aqueous extract was located in the following category: not classified as toxic (CTA 5), while hydroalcoholic extract at 25% was classified as dangerous (CTA 4). Both extracts can be used without side reaction that irritates the skin which permitted classification as potentially not irritant. P. mammosa in the two extracts caused mild and reversible eye irritation, and it was classified as slightly irritating.

Cryptocapsinepoxide-type carotenoids from red mamey, Pouteria sapota.

New carotenoids, cryptocapsin-5,6-epoxide, 3'-deoxycapsanthin-5,6-epoxide, and cryptocapsin-5,8-epoxides, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Cryptocapsin-5,6-epoxide was prepared by partial synthesis via epoxidation of cryptocapsin, and the (5R,6S)- and (5S,6R)-stereoisomers were identified by HPLC-ECD analysis. Spectroscopic data of the natural (anti) and semisynthetic (syn) derivatives obtained by acid-catalyzed rearrangement of cryptocapsin-5,8-epoxide stereoisomers were compared for structural elucidation. Chiral HPLC separation of natural and semisynthetic samples of cryptocapsin-5,8-epoxides was performed, and HPLC-ECD analysis allowed configurational assignment of the separated stereoisomers.

Neuroprotective effects of Pouteria ramiflora (Mart.) Radlk (Sapotaceae) extract on the brains of rats with streptozotocin-induced diabetes.

Diabetes mellitus is a chronic disease involving persistent hyperglycemia, which causes an imbalance between reactive oxygen species and antioxidant enzymes and results in damage to various tissues, including the brain. Many societies have traditionally employed medicinal plants to control the hyperglycemia. Pouteria ramiflora, a species occurring in the savanna biome of the Cerrado (Brazil) has been studied because of its possible ability to inhibit carbohydrate digestion. Rats with streptozotocin-induced diabetes treated with an alcoholic extract of Pouteria ramiflora show an improved glycemic level, increased glutathione peroxidase activity, decreased superoxide dismutase activity, and reduced lipid peroxidation and antioxidant status. The extract also restored myosin-Va expression and the nuclear diameters of pyramidal neurons of the CA3 subregion and that of the polymorphic cells of the hilus. We conclude that Pouteria ramiflora extract exerts a neuroprotective effect against oxidative damage and myosin-Va expression and is able to prevent hippocampal neuronal loss in the CA3 and hilus subfields of diabetic rats. However, future studies are needed to understand the mechanism of action of Pouteria ramiflora extract in acute and chronic diabetes.

Pouteria ramiflora extract inhibits salivary amylolytic activity and decreases glycemic level in mice.

In this study, extracts of plant species from the Cerrado biome were assessed in order to find potential inhibitors of human salivary alpha-amylase. The plants were collected and extracts were obtained from leaves, bark, and roots. We performed a preliminary phytochemical analysis and a screening for salivar alpha-amylase inhibitory activity. Only three botanical families (Sapotaceae, Sapindaceae and Flacourtiaceae) and 16 extracts showed a substantial inhibition (>75%) of alpha-amylase. The ethanolic extracts of Pouteria ramiflora obtained from stem barks and root barks decreased amylolytic activity above 95% at a final concentration of 20 µg/mL. Thus, adult male Swiss mice were treated orally with P. ramiflora in acute toxicity and glycemic control studies. Daily administration with 25, 50 and 100 mg/kg of aqueous extract of P. ramiflora for eight days can reduce significantly body weight and blood glucose level in mice. These data suggest that the crude polar extract of P. ramiflora decreases salivary amylolytic activity while lowering the blood levels of glucose.

Pouteria spp. fruits: Health benefits of bioactive compounds and their potential for the food industry.

The Sapotaceae family encompasses the genus Pouteria spp., comprising approximately 1,250 species of fruits cherished by consumers for their delightful assortment and flavors. Over the years, extensive research has been devoted to exploring the natural bioactive compounds present in these fruits, with the primary goal of preventing and/or mitigating the risk of degenerative diseases. Despite their widespread popularity in numerous countries, the chemistry, nutritional content, and biological potential of these fruits remain relatively unexplored. This comprehensive review aims to shed light on the principal volatile and non-volatile chemical components found in Pouteria fruits, which present notable antioxidant properties. By doing so, a broad perspective on the current trends in characterizing these compounds and their potential applications were provided, as well as the associated health benefits. Additionally, the prospects and potential applications of Pouteria fruits in the food industry were explored herein.

Inhibitory activity of α-amylase and α-glucosidase by plant extracts from the Brazilian cerrado.

Diabetes mellitus is the most common disease in the world. One therapeutic approach for treating diabetes is inhibition of α-amylase and α-glucosidase activities to reduce postprandial blood glucose levels. In vitro tests showed that several plant extracts from Brazilian cerrado species can inhibit the activity of α-amylase and α-glucosidase. The extracts of Eugenia dysenterica, Stryphnodendron adstringens, Pouteria caimito, Pouteria ramiflora, and Pouteria torta showed strong α-amylase and α-glucosidase inhibitory activity. Eugenia dysenterica, P. caimito, P. ramiflora, and P. torta aqueous extracts exerted the highest activity against α-amylase (IC50) values of 14.93, 13.6, 7.08, and 5.67 µg/mL, respectively) and α-glucosidase (IC50 values of 0.46, 2.58, 0.35, and 0.22 µg/mL, respectively). Stryphnodendron adstringens ethanol extract also exhibited inhibitory activity against both enzymes (IC50) 1.86 µg/mL against α-amylase and 0.61 µg/mL against α-glucosidase). The results suggest that the activity of these cerrado plants on α-amylase and α-glucosidase represents a potential tool for development of new strategies for treatment of diabetes.

Pouteria sapota (Red Mamey Fruit): Chemistry and Biological Activity of Carotenoids.

BACKGROUND: Red mamey is the fruit of P. sapota, a tree found in Mesoamerica and Asia. This fruit is considered a nutraceutical due to its multiple beneficial health including antiamyloidogenic activity and potential anti-tumorigenic property. Red mamey contain a variety of carotenoids including novel ketocarotenoids such as sapotexanthin and cryptocapsin. A ketocarotenoid is a chemical compound with a carbonyl group present in the ß-ring or in the double bond chain of a carotenoid. In red mamey, the 3'-deoxy-k-end group in sapotexanthin has proven to be an important pro-vitamin A source, which is essential for maintaining a healthy vision and cognitive processes. OBJECTIVE: This work reviews the current knowledge about the chemistry and biological activities of carotenoids in red mamey. METHOD: An exhaustive extraction is the most usual methodology to isolate and thoroughly characterize the carotenoids present in this fruit. High performance liquid chromatography is used to determine the profile of total carotenoids and its purity, while atmospheric pressure chemical ionization was used to determine their molecular weight and nuclear magnetic resonance determined their structure. RESULT: For each 100 g of fresh weight, 0.12 mg of total carotenoid from this fruit can be obtained. Out of the more than 47 reported carotenoids in red mamey, only 34 have a detailed characterization. CONCLUSION: It is important to continue studying the chemical composition and biological activity of this unique tropical fruit with commercial and nutritional value.

Sapotexanthin, an A-provitamin carotenoid from red mamey (Pouteria sapota).

From the ripe fruits of red mamey (Pouteria sapota) sapotexanthin, a new carotenoid, was identified as (all-E,5'R)-ß,κ-caroten-6'-one.

Characterization and the impact of in vitro simulated digestion on the stability and bioaccessibility of carotenoids and their esters in two Pouteria lucuma varieties.

Lucuma is a starchy orange-yellow fruit native to the Andean region. It is widely consumed in Latin America and has been recently adapted to the agronomical characteristics of the south region of Spain. However, its carotenoid profile has never been reported. The aim of this study was to characterize the carotenoid and carotenoid ester composition of lucuma pulps (var. Molina and Beltran) and assess their bioaccessibility with an in vitro simulated gastrointestinal digestion according to the INFOGEST® methodology. The carotenoid profile in lucuma pulps revealed a high qualitative diversity composed of 33 compounds, corresponding to 9 free xanthophylls, 9 hydrocarbon carotenes and 15 xanthophyll esters. (13Z)-violaxanthin, (all-E)-violaxanthin and (all-E)-antheraxanthin were the most abundant carotenoids in lucuma fruits and were naturally present as xanthophyll esters: (all-E)-antheraxanthin 3-O-palmitate, (all-E)-violaxanthin laurate and (all-E)-violaxanthin palmitate. Carotenoids were stable during in vitro digestion; however, their release from the food matrix was limited which contributed to their low bioaccessibility.

13,27-Cycloursane, ursane and oleanane triterpenoids from the leaves of Lucuma nervosa.

One hitherto unknown 24-nor-13,27-cycloursane-type triterpenoid, lucumic acid A (1), one new 24-nor-ursane triterpenoid, lucumic acid B (2), along with six known triterpenoids were isolated from the ethanol extract of the leaves of Lucuma nervosa. Their structures were established on the basis of spectroscopic data interpretation. Lucumic acid A (1) is the first example of a 24-nor-triterpenoid with a 13,27-cyclopropane ring.

Pouterin, a novel potential cytotoxic lectin-like protein with apoptosis-inducing activity in tumorigenic mammalian cells.

In this study, the cytotoxicity of pouterin in tumorigenic and non-tumorigenic mammalian cell lines was investigated. We found that HeLa, Hep-2 and HT-29 tumor cells were highly sensitive to pouterin cytotoxicity in a dose-dependent manner, whereas non-tumorigenic Vero cells and human lymphocytes were relatively resistant to the protein. Among the tumor cell lines, HeLa cells showed the highest susceptibility to pouterin cytotoxicity, exhibiting a time-dependent increase in LDH leakage and an IC(50) value of 5mug/mL. Morphological alterations such as rounding, cell shrinkage and chromatin condensation, consistent with apoptotic cell death were observed. Apoptosis induction was demonstrated by DNA fragmentation as detected by terminal dUTP nick-end labeling (TUNEL). Furthermore, HeLa cells incubated with pouterin showed disruption of the actin cytoskeleton. Western blot analysis revealed that pouterin caused increased expression of p21, thus indicating cell cycle arrest. Subsequent studies provided evidence that apoptosis may be partially explained in the activation of the tumor necrosis factor receptor 1 (TNFR1) signaling. Interestingly, a time-dependent decrease of the expression of p65 nuclear factor kappa B (NFkappaB) subunit, concomitant with a downregulation of the inhibitor of apoptosis protein 1 (IAP1) was observed, suggesting that TNFR-mediated apoptosis is the predominant pathway induced by pouterin in HeLa cells.

Evaluation of antidiabetic activity of biologically synthesized silver nanoparticles using Pouteria sapota in streptozotocin-induced diabetic rats.

BACKGROUND: Medicinal plants and green synthesis of silver nanoparticles (AgNPs) have proven to be good sources of agents effective in the treatment of diabetes mellitus. The present study focused on the green synthesis of AgNPs from the aqueous leaf extract of Pouteria sapota in order to evaluate the in vitro and in vivo antidiabetic properties of this extract and the synthesized AgNPs. METHODS: The AgNPs were biologically synthesized under ambient conditions from an aqueous leaf extract of P. sapota using the hot percolation method and were characterized using spectroscopic methods, X-ray diffraction, and scanning electron microscopy. The in vitro antidiabetic activity of the aqueous leaf extract and AgNPs was confirmed by non-enzymatic glycosylation of hemoglobin, glucose uptake by yeast cells following exposure of cells to 5 or 10 mmol/L glucose solution, and inhibition of α-amylase. Further, in vivo antidiabetic activity was assessed in streptozotocin-induced rats. Rats were treated with aqueous leaf extract (100 mg/kg) or AgNPs (10 mg/kg) for 28 days. Following treatment, rats were killed for biochemical and histopathological analysis of kidney and liver samples. RESULTS: A significant reduction in blood sugar levels was noted in rats treated with leaf extract or AgNPs. Results of in vitro and in vivo analyses in rats treated with leaf extract or AgNPs show that both the extract and the biologically synthesized AgNPs have antidiabetic activity. CONCLUSION: The aqueous leaf extract of P. sapota and AgNPs exhibited efficient antidiabetic activity in the rat model of diabetes and therefore could have potential for development for medical applications in the future.

Insecticidal and antifungal activity of a protein from Pouteria torta seeds with lectin-like properties.

This paper describes the purification and characterization of a novel protein from the seeds of Pouteria torta (family Sapotaceae). The protein was purified by a combination of gel filtration, ion-exchange, and reverse phase chromatographies. SDS-PAGE of the purified protein resulted in a single protein band of 14 kDa in the presence and absence of DTT. The lectin-like activity of pouterin was best inhibited by glycoproteins such as fetuin, asialofetuin, heparin, orosomucoid, and ovoalbumin. Pouterin inhibited the growth of the fungi Fusarium oxysporum and Colletotrichum musae and of the yeast Saccharomyces cerevisiae. The incorporation of pouterin into an artificial diet (final concentration = 0.12%, w/w) caused 50% mortality in larvae of the insect Callosobruchus maculatus, whereas 0.08% pouterin produced an ED50.

Carotenoids and carotenoid esters of orange- and yellow-fleshed mamey sapote (Pouteria sapota (Jacq.) H.E. Moore & Stearn) fruit and their post-prandial absorption in humans.

Although different genotypes of mamey sapote with distinct pulp colors are consumed in countries from Central to South America, in-depth knowledge on genotype-related differences of their carotenoid profile is lacking. Since the fruit was found to contain the potentially vitamin A-active keto-carotenoids sapotexanthin and cryptocapsin, we sought to qualitatively and quantitatively describe the carotenoid profile of different genotypes by HPLC-DAD-MSn. Sapotexanthin and cryptocapsin were present in all genotypes. Keto-carotenoids such as cryptocapsin, capsoneoxanthin, and their esters were most abundant in orange-fleshed fruit, whereas several carotenoid epoxides prevailed in yellow-fleshed fruit. Differing carotenoid profiles were associated with different color hues of the fruit pulp, while the widely variable carotenoid content (3.7-8.0mg/100gFW) was mainly reflected by differences in color intensity (chroma C∗). Furthermore, the post-prandial absorption of sapotexanthin to human plasma was proven for the first time. Besides sapotexanthin, cryptocapsin was found to be resorbed.

Pouteria torta epicarp as a useful source of α-amylase inhibitor in the control of type 2 diabetes.

Type 2 diabetes plays a major role in public health, affecting about 400 million adults. One of the used strategies to control type 2 diabetes is the inhibition of α-amylase activity to reduce post-prandial blood glucose levels. Therefore, in past decades, the search of new α-amylase inhibitors has led to the evaluation of natural products as a source of these compounds. Pouteria torta (Sapotaceae) is widespread in Brazil and bears edible fruits. Epicarp and pulp crude extracts of fresh fruits were studied for in vitro α-amylase inhibition activity. The pulp did not present activity while epicarp, usually considered as waste, showed a high α-amylase inhibitory capacity when compared with acarbose and Triticum aestivum. Therefore, an assay-guided fractionation study of epicarp crude extract was performed. Fraction VI shows very high inhibitory activity with IC50 of 9 µg/mL. However, subsequent fractionation led to lower inhibition potential (IC50 of 22.1 µg/mL). The qualitative characterization of fraction VI were performed by chromatographic and spectrometric analysis and showed the presence of epicatechin, catechin, sucrose, glucose, and fructose. Total phenolic and flavonoid contents and antioxidant capacity were also assessed and there seemed to be no correlation between phenolic or flavonoids-rich fractions and antioxidant capacity or α-amylase inhibitory activity.