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Antimicrobial constituents of Thomson seedless raisins (Vitis vinifera) against selected oral pathogens
Abstract
As a part of a project directed toward the discovery of oral antimicrobial compounds from plants, eight known compounds, oleanolic acid (1), oleanolic aldehyde (2), linoleic acid (3), linolenic acid (4), betulin (5), betulinic acid (6), 5-(hydroxymethyl)-2-furfural (7), and β-sitosterol were isolated from an hexane-soluble partition of a methanol extract of Thompson seedless raisins (Vitis vinifera). From an EtOAc-soluble partition rutin (8) and β-sitosterol glycoside were isolated. In an attempt to increase the resultant antimicrobial activity of oleanolic acid (1), a series of acylation and etherification reactions were performed on oleanolic acid to obtain derivatives 1a–1f. All the compounds isolated and the derivatives 1a–1f were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 2, 7 and 1f inhibited the growth of the test bacteria with concentrations ranging from 3.9 to 500μg/mL. Derivative 1f showed greatly enhanced antimicrobial activity when compared with oleanolic acid (1).
... Oleanolic acid also has antibacterial effects [34], as well as various physiological effects [35,36] including anti-inflammatory [37], antioxidant [38,39], antidiabetic [40], anticancer [41], neuroprotective [42], and hepatoprotective effects [43]. Triterpenes, such as oleanolic acid, derived from grapes or olives have been shown to suppress the growth of P. gingivalis in minimum inhibitory concentration (MIC) tests [44][45][46] and they prevented periodontitis by exerting anti-inflammatory effects in a rat model of acute periodontitis and in a mouse model of periodontitis [47,48]. The mechanism behind oleanolic acid's anti-inflammatory effects is the blockage of signal transduction pathways; this involves inhibiting the phosphorylation of nuclear factor-kappa B (NF-kB) and signal transducers and activators of transcription 1 (STAT 1), thereby suppressing the expression of inflammatory cytokines [36]. ...
... Regarding dental caries, the intake of this extract (36 mg of oleanolic acid as the active ingredient per day for 4 days) suppressed the growth of S. mutans in the oral cavity in a clinical study [52]. This study hypothesized that orally administered oleanolic acid extracted from pomace would also control periodontopathic bacterial growth in the human oral cavity, which has been observed in in vitro and animal tests [44][45][46]. Therefore, this study aimed to examine the effect of oleanolic acid tablets, containing 27 mg or 9 mg of oleanolic acid, on periodontopathic bacterial growth in human saliva. ...
... However, this study focused on oleanolic acid, which does not transfer to wine, from the perspective of the Sustainable Development Goals. Oleanolic acid has been reported to inhibit the growth of periodontopathic bacteria, including P. gingivalis, Actinobacillus actinomycetemcomitans, and Fusobacterium nucleatum, as demonstrated in MIC tests [44][45][46]. More than 700 types of bacteria inhabiting the oral cavity have been reported [68]. ...
Periodontal disease is caused by oral pathogenic bacteria and is associated with systemic disease and frailty. Therefore, its prevention is crucial in extending healthy life expectancy. This study aimed to evaluate the effect of orally administered oleanolic acid, extracted from wine pomace, on periodontopathic bacterial growth in healthy individuals. In this randomized, placebo-controlled, double-blind, parallel-group comparison study, 84 healthy adults were assigned to a placebo (n = 29), low-dose (n = 29, 9 mg oleanolic acid), or high-dose (n = 26, 27 mg oleanolic acid) groups. The number of oral bacteria in their saliva, collected before and 5 h after administration, was determined using the polymerase chain reaction-invader technique. The proportion of periodontopathic bacteria among the total oral bacteria in the saliva was calculated. Oleanolic acid significantly decreased the proportion of Porphyromonas gingivalis among the total oral bacteria in a dose-dependent manner (p = 0.005 (low-dose) and p = 0.003 (high-dose) vs. placebo, Williams’ test). Moreover, high-dose oleanolic acid decreased the proportion of Tannerella forsythia (p = 0.064 vs. placebo, Williams’ test). Periodontopathic bacteria are closely associated with the development and progression of periodontal disease; thus, the continuous daily intake of oleanolic acid derived from pomace may be helpful in maintaining a healthy oral microbiome by controlling the proportion of periodontopathic bacteria.
... In addition to the available information about the danger of irresponsible fluoride use at high doses, negative publicity about fluoride in print and visual media in recent years has changed parents' perspectives and preferences towards fluoride-containing products [9][10][11]. The vagueness regarding fluoride-related information has led to the idea that natural or herbal compounds can be used as an alternative to fluoride in preventing and eliminating dental caries [12]. There are several studies evaluating the perspective of parents regarding dental preventive practices in Turkey [9,[13][14][15]. ...
... In studies published in the literature, parents' negative opinions about fluoride have led to the introduction of natural/herbal antimicrobial compounds as an alternative to fluoride [12,23]. ...
... Numerous naturally occurring components in foods and vegetables have been shown to promote health and reduce the risk of many common diseases. It has been suggested that plantderived antimicrobial compounds can be used as an alternative to the chemical compounds commonly used to control dental plaque and dental caries [12,23]. In our study, although most of the parents stated that fluoride prevents dental caries and that they would prefer fluoridated toothpaste for their children, they reported that they would prefer natural/herbal alternatives instead of fluorinated varnish. ...
Objective: Dental caries poses a significant health concern affecting, 60%-90% of children globally. While fluoride is widely utilized to prevent and eliminate dental caries, recent negative media coverage and concerns about irresponsible fluoride use have prompted a shift in parental perspectives. This study explores parental knowledge, preferences, and attitudes regarding preventive measures, with a focus on fluoride and potential natural or herbal alternatives. Methods: Our research was designed as a survey study. A survey form consisting of 11 questions was delivered to parents of children aged 6–14 years and presented to the Erciyes University Department of Pediatric Dentistry for examination or treatment were included in the study. A total of 300 parents participated in the study. Data was recorded as numbers and percentages. Results: Of the parents, 69% (207) reported that if they were offered natural herbal compounds instead of fluorinated varnish, they would prefer natural alternatives. A statistically significant relationship was found between the responses received from the parents about the effects of fluoride and the educational level of the parents (p<0.05). Only 4 (1.3%) university graduate parents stated that fluoride had harmful effects. We found that 80.95% of the fathers and 68.39% of the mothers stated that they would prefer natural or herbal alternatives for their children instead of fluorinated varnish, and this was a statistically significant result (p<0.05). Conclusion: Parents do not have sufficient knowledge and attitudes about preventive practices in oral dental health, and some parents still avoid the use of fluoride products. Therefore, there is a need to increase fluoride intake and its effects on children's health by educating parents or informing dentists.
... Screening for antimicrobial agents isolated from plants is a feasible approach to the identification of natural compounds with antimicrobial properties against dental pathogens (Tichy and Novak, 1998). In fact, compounds that possess antimicrobial activities against oral pathogens are now being isolated from plants traditionally used as oral remedies (Rivero-Cruz et al., 2008). ...
... The authors cite other studies where rhein inhibits the action of gingipains, enzymes that provide peptides and amino acids to aid the growth of P. gingivalis. -Cruz et al. (2008) demonstrated the power of raisins in improving oral health. Raisins are dried grapes, the fruits of the plant V. vinifera (family Vitaceae). ...
... Various phytochemicals found in raisins include triterpenes, fatty acids, flavonoids, amino acids, hydroxycinnamic acids and 5hydroxymethyl-2-furaldehyde (Rivero-Cruz et al., 2008). Oleanolic acid, oleanolic aldehyde, and 5-(hydroxymethyl)-2-furfural stall the growth of P. gingivalis, with minimum inhibitory concentration (MIC) values ranging from 3.5 to 488 g/mL (Rivero-Cruz et al., 2008). ...
... Nowadays, most raisins are produced from Thompson seedless grapes. Alternatively, Muscat grapes and Black Corinth grapes can also be used for the production of raisins (Rivero-Cruz et al., 2008). Raisins are traditionally sun-dried, but may also be water-dipped and artificially dehydrated (Fadhel et al., 2005). ...
... Although health benefits of raisins have been studied extensively (an important source of polyphenols, antioxidants, and flavonoids) (Rivero-Cruz et al., 2008;Williamson and Carughi, 2010;Fang et al., 2010;Jeszka-Skowron et al., 2017), little has been reported about the good quality and safety of the raisins, in order to protect the consumers from Table 1 Chromatographic and multiple reaction monitoring (MRM) parameters for pesticides analyzed by GC-MS/MS. chemicals, in particular from the residues of pesticides. ...
A multi-residue method for the simultaneous analysis of a wide range of pesticides in raisins using liquid and gas chromatography-tandem mass spectrometry (LC-MS/MS and GC–MS/MS) has been validated. Pesticides are extracted from raisins with ethyl acetate, followed by centrifugation. The validation study was in accordance with DG SANTE guidelines. Validation experiments have been performed in both analytical instruments. A total number of 314 pesticides were spiked in raisins of organic farming at two spiking levels for GC–MS/MS (0.025 and 0.1 mg/kg), and at three spiking levels for LC-MS/MS (0.005, 0.05, and 0.1 mg/kg) with 6 replicates at each concentration. The scope of validation included linearity, limits of quantification (LOQ), accuracy, precision, and matrix effects (%) for each pesticide. The validated method was then applied for the analysis of 37 commercial raisin samples purchased from the market. For the evaluation of the results, processing factors (PFs) have been applied to derive the amount of residue in raisins, from the maximum residue levels (MRLs) of grapes, and which in this paper will be referred as to the MRL expressed in raisins. In all conventional samples, pesticides were detected at concentrations above the LOQ. In total, 55 different pesticides were detected. All conventional samples contained multiple pesticides ranging from 2 to 24. On the other hand, samples from organic farming were found to be free of the analysed pesticides. The 13.5% of the examined samples were considered as violations. The exposure assessment for the acute risk of the violating samples indicated that no potential risk derives from the detected and approved in the EU pesticides, while the detection of not approved pesticides in the EU, and the lack of toxicological reference values for certain pesticides raise concerns for the human health, especially for children. The results of the survey study indicate the need to include processed samples, and in particular dry fruits with a high consumption rate such as raisins, in the official controls of pesticide residues in food.
... Both the total and individual phenolic content vary widely among different raisin varieties [14,15]. Other minor phytochemicals found in raisins are triterpenoids (oleanolic acid, oleanolic aldehyde, betulin and betulinic acid) [16] and tartaric acid, which works synergistically with fiber to maintain a healthy digestive system [17]. ...
... In 2008, Rivero-Cruz et al. [16] investigated the antimicrobial activity of compounds isolated from raisins and some derivatives against two oral pathogens: Streptococcus mutans and Porphyromonas gingivalis, linked to caries and periodontal disease, respectively. The compounds oleanolic acid, oleanolic aldehyde, 5-(hydroxymethyl)-2-furfural, and the derivative oleanolic acid sodium salt inhibited the growth of the test bacteria at concentrations ranging from 3.9 to 500 µg/mL. ...
Raisins are dried grapes consumed worldwide that contain beneficial components for human health. They are rich in fiber and phytochemicals such as phenolic compounds. Despite a 60% sugar content, several studies have reported health-promoting properties for raisins and this review compiles the intervention studies, as well as the cell line and animal model studies carried out to date. It has been demonstrated that raisins possess a low-to-moderate glycemic index, which makes them a healthy snack. They seem to contribute to a better diet quality and may reduce appetite. Their antioxidant capacity has been correlated to the phenolic content and this may be involved in the improvement of cardiovascular health. In addition, raisins maintain a good oral health due to their antibacterial activity, low adherence to teeth and an optimum oral pH. Raisin consumption also seems to be favorable for colon function, although more studies should be done to conclude this benefit. Moreover, gut microbiota could be affected by the prebiotic content of raisins. Cell line and animal model studies show other potential benefits in specific diseases, such as cancer and Alzheimer's disease. However, deeper research is required and future intervention studies with humans are needed. Overall, incorporating an 80-90 g portion of raisins (half a cup) into the daily diet may be favorable for human health.
... This is in disagreement with previous studies that showed the addition of medicinal plants affected significantly the growth of probiotics in yogurt and other dairy products [7,14,[24][25][26][27]. The addition of raisins in yogurt inhibited the growth of A. parasiticus at 7 & 14 days which may occur as a result of raisins phenolic compounds with antimicrobial activity [28]. Further studies are needed to evaluate and characterize the phenolic profiles of raisins yogurt with antimicrobial activity. ...
... The moderate effects of plain and raisins yogurt with L. gasseri on inhibition of A. parasiticus may refer to some physical factors that affect antimicrobial activity of raisins such as low pH, low water activity, and high osmolality [12]. Gamba et al. [28] have observed that kefir-cell-free-supernatants produced antifungal activity against A. parasiticus at pH 3.5 and concentration of 65% v/v. Furthermore, probiotic bacteria such as Lactobacillus delbrueckii and Lactobacillus rhamnosus showed significant effect on the growth inhibition of A. parasiticus, morphological structure, and reducing aflatoxin production [30]. ...
Background and objective: Aspergillus parasiticus is a common fungus that produces aflatoxins and causes food contamination. Antifungal activity of Lactobacillus gasseri and raisins extract on the growth of Aspergillus parasiticus in yogurt (in vitro) were investigated.
Methodology: Two groups of yogurt samples were prepared. The first group consists of the plain yogurt with L. gasseri+A. parasiticus (control), and raisins yogurt with L. gasseri+A. parasiticus, and the second group consist of plain yogurt+A. parasiticus (control), and raisins yogurt+A. parasiticus. All yogurt samples were investigated for pH, titratable acidity (TA), viable cells count of L. gasseri and inhibition of A. parasiticus growth during 1, 7, & 14 days.
Results: The pH values of all samples were decreased non-significantly (p>0.05) during the storage period. The presence of raisins decreased (p<0.05) the total acidity in yogurt with L. gasseri+A. parasiticus (1.53%) compared to control (1.98%) at day 14 of storage. The viable cell numbers of L. gasseri (0.27×106 cfu/ml) in raisins yogurt+ A. parasiticus was lower (p<0.05) than control (0.39×106 cfu/ml) at day 14 of storage. Plain and raisins yogurt with L. gasseri showed moderate inhibition of A. parasiticus compared to without L. gasseri at 1 and 14 days of storage.
Conclusion: L. gasseri in a combination with raisins extract may have contributed to preventing A. parasiticus contamination in yogurt.
... The reduction of the inflammatory response by resveratrol seems to be mediated via modulation of Cox-2 expression and nuclear factor kappa-B (NF-kB) activation; however, this was reported in macrophages and endothelial cells and therefore an in-depth study with oral-like cultures is recommended (Murakami et al., 2015;Park et al., 2009). Although they are not polyphenols, the antimicrobial activity of some other components (oleanolic acid, linoleic acid, sodium salt of oleanolic acid and 5-(hydroxymethyl)-2furfural) of Vitis vinifera extract was described against the oral pathogens S. mutans and P. gingivalis (Rivero-Cruz, Zhu, Kinghorn, & Wu, 2008). ...
... ( Rivero-Cruz et al., 2008) Extract of Vitis amurensis Grapes Antimicrobial activity of oligostilbenes and stilbenes isolated from the leaf and stem of this plant, such as trans-ε-viniferin, against S. mutans and S. sanguis. (Yim et al., 2010) Red wine, dealcoholized red wine and red wine extract (þ/À grape seed or inactive dry yeast extracts) ...
... The compounds oleanolic, oleanolic aldehyde, and 5-(hydroxymethyl)-2-furfural were active against P. gingivalis, and those three compounds are found on the skin of grapes and raisin; in addition to rutin which was effective against S. mutans. 73 Wu 74 assessed the effects of grapes on oral health in an in vitro and an in vivo study. In vitro grape seed extract reduced demineralization in artificial root carie lesions. ...
... 23,[28][29][30][31][32][33] Raisins produce an oral environment that is non-cariogenic and do not fit the APP criterion for a choking hazard. 71,[73][74][75][76][77][78]80 ...
Purpose: This literature review was performed to assess the effect of raisins on human health. Methods: A review of Medline was conducted using the keywords: 'raisins, raisins and health, raisins and cardiovascular disease (CVD), raisins and cancer, raisins and diabetes, raisins and fiber, raisins and colon health, raisins and antioxidants, raisins and inflammation, raisins and dental caries'. The reference lists from previous review articles on raisins and human health and the California Raisin Marketing Board files were reviewed for additional studies. Results: Raisins have one of the highest polyphenolic content and antioxidant ORAC levels compared to other traditional dried fruits. Many of the polyphenols in raisins are well assimilated and bioavailable. Raisin consumption reduces low density lipoprotein (LDL) cholesterol, blood pressure and blood sugar, when compared to equal caloric carbohydrate snacks and is associated with a reduced risk of CVD. The anti-inflammatory and cancer chemopreventive effects of raisins are mixed. Raisin consumption reduces intestinal transit time and positively affects gut microbiota. Raisins produce sustained energy during long term athletic competitions equal to traditional sports energy gels, shots and jelly beans. Raisins produce a non-cariogenic oral environment and do not fit the American Academy of Pediatrics criteria to be considered a choking hazard. Conclusions: Based on the review of literature, consumption of raisins provide numerous health benefits for promoting general wellness and in the prevention of many chronic diseases including: CVD, type 2 diabetes mellitus (T2DM) gastrointestinal diseases, and dental caries.
... The antibacterial activity of these extracts could be attributed to the presence of diverse molecules including 5-HMF, furfural, syringaldehyde, vanillin, among others. In fact, these compounds have been reported in the literature for their important antibacterial properties (Chai et al., 2013;Rivero-Cruz et al., 2008). For instance, Cava-Roda et al. (2012) evaluated the antibacterial activity of vanillin against several food-related bacteria, namely Escherichia coli O157:H7 and Listeria monocytogenes. ...
... Chai et al. (2013) reported the capacity of three furan compounds for prevent growth of Bacillus subtilis and Salmonella bacteria. Rivero-Cruz et al. (2008) evaluated antimicrobial activity of different compounds isolated of Thompson seedless raisins including 5-HMF, against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis, and they suggested that these compounds may benefit periodontal health. ...
Vine shoots, considered a residue from winery operations, possess valuable antioxidant and antimicrobial activities that can be potentially obtained under the scheme of biorefinery. In this framework, we evaluated the autohydrolysis of vine shoots combined with a further stage of extraction with ethyl acetate as viable valorization process. The extraction yield ranged from 0.95 to 3.80 g extract/100 g vine shoots. Moderately high temperature (215 °C) was required for the maximum recovery of phenolics, flavonoids and antioxidant activities. The major phenolic compounds identified were derived from lignin: vanillin, acetovanillone, guaiacylacetone, syringaldehyde and acetosyringone. The ethyl acetate extract from the liquors obtained at 200 °C was assayed for antimicrobial activity against Gram positive and negative bacteria showing values of MIC and MBC in the range of 5–20 mg/mL. This work showed that the antioxidant extracts could be used as cheap source of natural compounds, with potential applications in the food and pharmaceutical industries.
... Five chemicals in raisins; oleanolic acid, oleanolic aldehyde, betulin, betulinic acid, and 5-(hydroxymethyl)-2-furfural seem to be responsible for slowing the bacteria. In addition, oleanic acid prevents Streptococcus mutans from sticking to tooth enamel 5 . ...
... Although various in vitro studies have been performed to investigate the mode of actions of these phytochemicals and their effects on bodily functions, much less attention has been paid to their effects or their activity against bacteria. Therefore the current study aims to evaluate antibacterial activity of black raisins and vinegar of black raisins 5 . ...
Background: Raisins are dried grapes, prepared from some varieties of grapes (Vitis vinifera). The history of raisin consumption is very old. Objective: An evaluation of Antibacterial activity of the extracts of black raisins and black raisin vinegar against bacteria Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumonia, Streptococcus feacalis, Streptococcus mutanus, Streptococcus feacalis, Escherichia coli, Salmonella typhi, Moraxallia catarralis, Pseudomonas aeroginosa, Proteus mirabilis, Klebsiella pneumonia, Enterobacter spp. Acinetobacter, Serratias pp and Candida albicance. Methods: Two black raisins products were used to determine the antibacterial activity of black raisins; crude aquatic extracts of dried black raisins, and the vinegar of dried black raisins. Agar well diffusion method, biofilm inhibition test using tissue culture plate method, adherence and swarming inhibition assays were done for estimation and evaluation of the antibacterial activity of black raisins. Results: Result showed that both the crude extract of black raisins and the vinegar of black raisins have potential antibacterial activity. The results were determined by measuring the inhibition zone, the inhibition of bacterial motility using swarming assay with all gradual different concentrations of black raisins and the vinegar of black raisins (Pearson correlation =0.9; P value ≤ 0.05, the inhibition of bacterial cell adherence to oral epithelial cells, quorum sensing and biofilm formation. Conclusions: Black Raisins and vinegar of black raisins exhibit marked antimicrobial activity bacteria and fungicidal activity. They can inhibit motility, inhibit biofilm formation and inhibit bacterial cell adherence to oral epithelial cells. Based on the results it can be concluded that they can inhibit bacterial colonization and adherence to teeth and oral cavity, and provide production against different human pathogens and this may have clinical relevance.
... They also have nutritional benefits and the potential as a functional food. The dried, seedless grapes produce raisins, which are consumed widely for their health-promoting effects [151][152][153]. ...
Diabetes mellitus (DM) comprises a range of metabolic disorders characterized by high blood glucose levels caused by defects in insulin release, insulin action, or both. DM is a widespread condition that affects a substantial portion of the global population, causing high morbidity and mortality rates. The prevalence of this major public health crisis is predicted to increase in the forthcoming years. Although several drugs are available to manage DM, these are associated with adverse side effects, which limits their use. In underdeveloped countries, where such drugs are often costly and not widely available, many people continue to rely on alternative traditional medicine, including medicinal plants. The latter serves as a source of primary healthcare and plant-based foods in many low-and middle-income countries. Interestingly, many of the phytochemicals they contain have been demonstrated to possess antidiabetic activity such as lowering blood glucose levels, stimulating insulin secretion, and alleviating diabetic complications. Therefore, such plants may provide protective effects that could be used in the management of DM. The purpose of this article was to review the medicinal plant-based foods traditionally used for the management of DM, including their therapeutic effects, pharmacologically active phytoconstituents, and antidiabetic mode of action at the molecular level. It also presents future avenues for research in this field.
... They also have a nutritional benefit and potential as a functional food. The dried, seedless grapes produce raisins which are consumed widely for their health-promoting effects [151][152][153]. ...
Diabetes mellitus (DM) comprises a range of metabolic disorders characterized by high blood glucose levels caused by defects in insulin release, insulin action, or both. DM is a widespread condition that affects a substantial portion of the global population, causing high morbidity and mortality rates. The prevalence of this major public health crisis is predicted to increase in the forthcoming years. Although, several drugs are available to manage DM, these are associated with adverse side effects, which limits their use. In underdeveloped countries, where such drugs are often costly and not widely available, many people continue to rely on alternative traditional medicine, including medicinal plants. The latter serve as a source of primary healthcare and plant-based foods in many low and middle-income countries. Interestingly, many of the phytochemicals they contain have been demonstrated to possess antidiabetic activity such as lowering blood glucose levels, stimulating insulin secretion and alleviating diabetic complications. Therefore, such plants may provide protective effects that could be used in the management of DM. The purpose of this article was to review the medicinal plant-based foods traditionally used for the management of DM, including their therapeutic effects, pharmacologically-active phytoconstituents and antidiabetic mode of action at the molecular level. It also presents future avenues for research in this field.
... In addition, it does not remain on the teeth for a long time (Wong et al., 2013). Raisin contains photo-chemical antimicrobials which inhibit the growth of oral bacteria linked to dental caries (Rivero-Cruz et al., 2008). In previous studies, however, the effect of raisin on hardness has been directly investigated in only one case, and often on grape juice. ...
Background: This study investigated the effect of exposure of enamel surfaces to dried fruit suspension including dates, raisins, and dried apricot on their micro-hardness changes. Methods: In this in vitro study, fifty enamel sections of bovine incisor teeth were mounted inside the acrylic resin so that the enamel surface would not be exposed to the acrylic. After surface polishing, the initial micro-hardness was measured by a Vickers hardness-testing machine. The samples were randomly placed into five different solutions including apricot, raisin and date suspension, citric acid (positive control) or sorbitol (negative control), 5 times a day, each time for 5 minutes, and then in artificial saliva for 60 minutes. This process was repeated for 20 days. Eventually, the final micro-hardness of the samples was measured. Micro-hardness changes between groups were compared through ANOVA and TUKEY test using SPSS 23 software with a significance level of P<0.05. Results: After exposure, the micro-hardness of the teeth was significantly reduced in all three suspensions prepared from dried fruit (P<0.05). Apricot and date had the highest and lowest effects on reducing the micro-hardness of teeth, respectively. Sorbitol solution did not have a significant effect on changing the micro-hardness of teeth (P=0.13). Conclusion: The suspension of studied fruits (apricot, raisin, date) causes a significant reduction in micro-hardness of the dental enamel surface, indicating the negative effect of frequent consumption of dried fruits over long periods of time on dental health.
... Furthermore, other triterpenoids have been identified in grape berry cuticular wax, such as oleanolic aldehyde (Dagna et al., 1982;Zhang et al. 2004), erythrodiol (Dagna et al., 1982), phytosterols (e.g., lanosterol (Le Fur et al. 1994)), betulin, betulinic acid, lupeol (Rivero-Cruz et al., 2008). This layer is particularly rich in oleanolic acid (the content of this compound reaches between 50 and 80% of the total weight of the wax) (Radler and Horn, 1965;Comménil et al., 1997;Pensec et al., 2014). ...
In the frame of promoting sustainable vitiviniculture, the development of eco-friendly alternatives to synthetic chemical products for phytosanitary treatments against grapevine (Vitis vinifera) pests is gaining importance. One of the bio-control methods that can be proposed is the induction of plant immunity by using elicitors, also called plant defense stimulators (PDS), as these substances are biodegradable and, non-toxic to health and environment. A conferred resistance against various pathogens can be obtained with natural molecules acting most frequently through jasmonic acid (JA), salicylic acid (SA), and/or ethylene (ET) signaling pathways. These pathways are involved in the induction of defense-related genes such as those encoding enzymes responsible for the biosynthesis of stilbenes, which are the most important polyphenolic antimicrobial metabolites (phytoalexins) in Vitaceae. For vineyard protection, PDS can be applied as a complement for pesticides and not as a full replacement since their effectiveness is often variable according to pathogens and environmental conditions. In order to develop the strategies based on PDS use, more studies which could elucidate their mechanism of action are needed. The aim of this thesis was to examine the responses of grapevine to elicitors of different mode of action, as methyl jasmonate (MeJA), implicated in JA signaling pathway, 2,1,3-benzothiadiazole-7-carbothioic acid S-methyl ester (BTH), a synthetic analogue of SA, and phosphonates (PHOS), molecules of a double stimulator-fungicide action. Due to scarce information about steroids and pentacyclic triterpenoids in grapevine, their profile after PDS treatment were characterized in different grapevine experimental models using gas chromatography-mass spectrometry (GC-MS) analyses. Firstly, the effect of elicitation with MeJA was evaluated in cell suspension cultures (in vitro) of V. vinifera. An overproduction of bioactive pentacyclic triterpenoids occurred with differences according to the cultivar studied, i.e., acumulation of betulin and oleanolic acid or phytosterols was noted in respectively Petit Verdot, Gamay Teinturier and Cabernet Sauvignon cell suspension cultures. Then, elicitations were effectuated on the leaves of V. vinifera cv. Cabernet Sauvignon greenhouse cuttings. A stimulatory effect on the potentially defense-related pentacyclic triterpenoids at the expense of the biosynthesis of sterols, which are essential structural components of cell membranes, was shown. By the use of NeoVigen microarrays, and ultra-performance liquid chromatography-mass spectrometry (UHPLC-MS), the accumulation of defense-related transcripts and polyphenols (stilbenes, flavanols and flavonols) were noted after the three elicitors treatments. Grapevine protection conferred by these elicitors was confirmed on foliar discs against the biotrophic oomycete Plasmopara viticola, the causal agent of downy mildew. Furthermore, the impact of PDS on primary metabolism should be evaluated in order to ensure, in the longer term, the best trade-off between growth, yield and defense. Thus, a thorough metabolomic approach using proton nuclear magnetic resonance spectroscopy (1H-NMR) was performed. A reprogramming similar and/or specific to the elicitor applied was noted, particularly within carbohydrates, amino acids, and some of the Krebs cycle intermediates. The research presented in the current dissertation revealed that the thorough comprehension of the interaction between elicitor, plant molecular and metabolic responses and pathogen, is crucial for the development of effective protection strategies based on the use of PDS for grapevine diseases control.
... It is then eluted with a mixture of CHCl3-MeOH (1:0-0:1) which gives nine fractions. The obtained fraction number 3 was separated on silica gel column and eluted with hexane: isopropyl alcohol (98:2 -50:50) to get a fraction of compound 1 as shown figure 2. The obtained fraction was analyzed on the basis of TLC method using Chloroform: methanol-95:5 as a developing solvent, and the spots were visualized by using iodine chamber [16][17][18]. Figure 1. Column Chromatography for obtaining oleanolic acid Plant 2 -The ethanol extract (3.5 ml) was dissolved in ethyl acetate and a dry mixture is made by mixing it in silica gel. ...
Solvent extractions of shade dried seeds of Cyamopsis tetragonoloba, Pithecellobium dulce and Coriandrum sativum plants were executed using organic solvents. The obtained extracted crudes were subjected to the chemical analysis followed by instrumental analysis using standard procedures to identify the naturally occurring phytochemicals [1, 2, 3,]. Limonene, Oleanolic acid and Linalool were obtained from ethanol extracts of Cyamopsistetragonoloba , methanol extract of Pithecellobium dulce and acetone extract of Coriandrumsativum respectively. The compound identification were confirmed by ¹ H NMR, ¹³ C NMR, IR and Mass spectroscopy [4]. The anti-cancer activity of the extracted terpenes determined using in-vitro analysis on HeLa-Human cervix cell lines. The obtained IC 50 value of Oleanolic acid shows better biological activity against HeLa cell lines. It was also found that there is no cell lysis in HeLa cell lines in case of Limonene with concentration less than 30 μg. However, biological activity of Linalool is better in case of HeLa cell line. This suggests that Oleanolic acid and Linalool is good anti-cancer agent as reported from in vitro studies against Hela-Human cervix cell line.
... The study conducted by Rivero-Cruz et al. aimed at the fractionation of hexaneand ethyl acetate-soluble partitions of V. vinifera extract and the isolation of antimicrobial compounds, followed by an evaluation of antimicrobial activity on S. mutans. Among all the compounds tested, oleanolic acid, oleanolic aldehyde, 5-(hydroxymethyl)-2-furfural (7), and rutin showed an inhibitory effect against S. mutans [85]. ...
Oral health is considered an important factor of general health and it contributes to the quality of life. Despite the raising awareness of preventive measures, the prevalence of oral health conditions continues to increase. In this context, a growing interest in investigating natural resources like Vitis vinifera (V. vinifera) phenolic compounds (PhCs) as oral health promoters has emerged. This paper aims to review the evidence about the bioactivities of V. vinifera by-products in oral health. Up to date, a high number of studies have thoroughly reported the antimicrobial and antiplaque activity of V. vinifera extracts against S. mutans or in multi-species biofilms. Moreover, the bioactive compounds from V. vinifera by-products have been shown to modulate the periodontal inflammatory response and the underlying oxidative stress imbalance induced by the pathogenic bacteria. Considering these beneficial effects, the utility of V. vinifera by-products in the maintaining of oral health and the necessary steps towards the development of oral care products were emphasized. In conclusion, the high potential of V. vinifera by-products could be valorized in the development of oral hygiene products with multi-target actions in the prevention and progression of several oral conditions.
... Sultanina (seedless raisins) contains the active component i.e. HMF, which prevents the growth of oral pathogens (Porphyromonas gingivalis and Streptococcus mutans) which can cause periodontal disease and caries (Rivero-Cruz et al. 2008). In addition to that, HMF, also inhibits the fermentation of Saccharomyces cerevisiae and itself converts into hydroxymethylfurfuryl alcohol (Akıllıoglu et al. 2011). ...
5-Hydroxymethylfurfural (HMF) is synthesized by the thermal decomposition of the sugars. Numerous types of food products are having a significant amount of HMF. Besides the thermal processing, other food processing methods (drying and dehydration, roasting, baking and storage of the product) are important factors for the synthesis of the HMF. HMF possesses different health effects including positive and negative health effects. Only few regulatory bodies have issued the guidelines and limits related to HMF. The present review has been planned to explore the HMF in terms of synthesis, occurrence, the effect of food processing, health effects and the safety guidelines.
... AN = growth inhibitory activity against S. mutans and P. gingivalis. [187,188] Gummosogenin AC, CT AC = strong inhibitory effect on the acetic acid-induced writhing test. CT = inhibition of cervical (HeLa) cancer cell line proliferation. ...
The Cactaceae family is an important source of triterpenes and sterols. The wide uses of those plants include food, gathering, medicinal, and live fences. Several studies have led to the isolation and characterization of many bioactive compounds. This review is focused on the chemistry and biological properties of sterols and triterpenes isolated mainly from some species with columnar and arborescent growth forms of Mexican Cactaceae. Regarding the biological properties of those compounds, apart from a few cases, their molecular mechanisms displayed are not still fully understand. To contribute to the above, computational chemistry tools have given a boost to traditional methods used in natural products research, allowing a more comprehensive exploration of chemistry and biological activities of isolated compounds and extracts. From this information an in silico bioprospection was carried out. The results suggest that sterols and triterpenoids present in Cactaceae have interesting substitution patterns that allow them to interact with some bio targets related to inflammation, metabolic diseases, and neurodegenerative processes. Thus, they should be considered as attractive leads for the development of drugs for the management of chronic degenerative diseases.
... 196−199 As well as phenols, oleanolic acid, linoleic acid, the sodium salt of oleanolic acid, and 5-(hydroxymethyl)-2-furfural obtained from Vitis vinifera have also exhibited antimicrobial activity against oral pathogens, such as P. gingivalis and S. mutans. 194 Dietary supplementation with beetroot juice rich in nitrate (NO 3 − ) can increase salivary pH and alter the abundance of Neisseria, Prevotella, and Actinomyces, thus improving oral health. 195 However, it is important to note that more efforts are needed to develop dietary components that promote oral health and, thereby, prevent systemic diseases. ...
Numerous recent observation and intervention studies suggest that the microbiota in the gut and oral cavity play important roles in host physiology, including disease development and progression. Of the many environmental factors involved, dietary components play a pivotal role in shaping the microbiota community and function, thus eliciting beneficial or detrimental consequences on host health. The microbiota affects human physiology by altering the chemical structures of dietary components thus creating new biological properties and modifying their lifetime and bioavailability. This review will describe the causal mechanisms between the microbiota and some specific bacterial species and diet components providing health benefits, and how this knowledge could be incorporated in dietary strategies for improving human health.
... Anticancer, dissolve gall stones, heartburn and gastroesophageal re-flux disorder (gerd) [101-106] Inhibit sickling of red blood cells, relieve fatigue, improvement in learning and memory, antioxidative, anti-apoptotic activity anticarcinogenic action, antimicrobial (, anti-hypoxic effect anti-inflammatory[147][148][149][150][151][152][153][154][155][156][157][158][159][160][161][162][163][164] ...
... Abouzeed et al. (2018) indicated that the raisin acetonic extract exhibited significant activity against S. aureus, whereas the effect against P. aeruginosa, E. coli, and S. typhimurium was non-significant as compared to the inhibitory zone of cefotaxime sodium standard. The minimal inhibitory concentration (MIC) value of acetonic extracts was 25 mg/ml against S. aureus and 100 mg/ml for the other tested bacteria strains, while Rivero-Cruz et al. (2008) demonstrated that some constituents of Thompson seedless raisins (Vitis vinifera) inhibited the growth of two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis, which are associated with caries and periodontal disease, respectively. ...
This review aims to give a summary of what has been found so far about the profile in bioactive molecules and the beneficial effect of dried fruit commercially available and commonly consumed in Algeria. It is known that Mediterranean diets, especially the Algerian one, are characterized by the presence, in the food ration, of virgin olive oil, fruits (fresh or dried) and vegetables in abundance, cereals and vegetables (fresh or processed), olives and seeds. Dried fruits come in several preparations (main dishes, dessert, cakes) in Algeria. In recent years, Mediterranean diets, including Algerian diet, have attracted a lot of attention from the scientific community because of the beneficial effect they have on health, especially cardiovascular health, and this in relation to the presence of bioactive molecules such as phenolic compounds, carotenoids, certain vitamins, and many others. In this work, the bioactive molecules’ profile, antioxidant activities, and the beneficial health effects of some dried fruit (dried fig, raisins, dried apricot, and prune) commonly consumed in Algeria are examined. In general, the results of this review paper emphasize the importance of dry fruit consumption on health on the one hand and on the other hand, encourage the decision-makers in the agricultural sector to promote and protect shrub culture to benefit from the nutritional quality of dried fruits and thus improve the health and long-term well-being of the consumer.
... Anticancer, dissolve gall stones, heartburn and gastroesophageal re-flux disorder (gerd) [101-106] Inhibit sickling of red blood cells, relieve fatigue, improvement in learning and memory, antioxidative, anti-apoptotic activity anticarcinogenic action, antimicrobial, anti-hypoxic effect anti-inflammatory[147][148][149][150][151][152][153][154][155][156][157][158][159][160][161][162][163][164] ...
... Anticancer, dissolve gall stones, heartburn and gastroesophageal re-flux disorder (gerd) [101-106] Inhibit sickling of red blood cells, relieve fatigue, improvement in learning and memory, antioxidative, anti-apoptotic activity anticarcinogenic action, antimicrobial, anti-hypoxic effect anti-inflammatory[147][148][149][150][151][152][153][154][155][156][157][158][159][160][161][162][163][164] ...
Astavarga is nature's most extravagant group of flowering plants found in Himalayan region. As the name Astavarga
indicates, it contains eight medicinal plants belonging to Zingiberaceae, Orchidaceae and Liliaceae family viz, Kakoli,
Kshirakakoli, Meda, Mahameda, Jeevak, Risbhaka, Riddhi and Vridddhi. As per Ayurveda this group of medicinal plants is
classified as Rasayana (Rejuvenation) and is important constituents of preparations like Chyawanprasha rasayan,
Ashtavarga churna, Brimhanigutika and Vajikaraghrita, etc. Astavarga plants are mostly used to treat sexual disorders,
physical weakness, body pain, strengthen the immune system and as an overall tonic. The plants under this group have
been the subject of limited biochemical phytochemical and biological activities investigations. Taking into consideration
the therapeutic significance of Astavarga plants as described in the ancient Ayurvedic system of medicine, the detailed
phytochemical and pharmacological studies appear imperative to scientifically validate the ancient claims. Thus, the
present review article provides detailed information on the Ayurvedic uses, habit and habitats, botanical descriptions,
chemical constituents and biological activities reported for this important group of plants. The chemical structures of the
isolated compounds from these plants and their reported biological activities in the literature have also been included.
The information provided in the present review may stimulate the researchers to explore their phytochemical and
pharmacological properties which have not yet been attempted, comprehensively. It will generate the interest on
“reverse pharmacology” approach to validate the knowledge that has been known from ancient times.
... The hexane soluble extract was subjected to silica gel column chromatography and eluted with mixture of CHCl 3 -MeOH (1:0-0:1) to give nine fractions. Fraction 3 was separated on silica gel VLC column and eluted with hexane:isopropyl alcohol gradient mixtures (98:2 -50:50) to yield oleanolic acid (Rivero-Cruz et al., 2008). Another example can be given for oleanolic acid isolation from Salvia officinalis. ...
... Raisin, the dried fruit of grape showed an antimicrobial activity in oral health. The phytochemical compounds in the raisin suppress the growth of oral bacteria and protect gum and dental health [199]. ...
Climber plants have attracted global attention for their hidden therapeutic potential and are generally rooted on the ground, but leaves often in full sun and blanketing canopies of trees. Climbers rely on some support from other plants and have active and passive climbing mechanisms with great diversity. Tropical forests are the harbors of enormous different fauna and flora species than any other ecosystem on earth and Malaysia is a biodiversity hotspot in Asia with a good amount of tropical forest cover. On the other hand, Iran is an important source of Herbal plants due to the weather and geographical situation. In this review six species of Malaysian and Iranian plants (Hedera helix, Rosa canina, Vitis vinifera, Aristolochia tagala, Gynura procumbens and Antigonon leptopus) are selected and botanical description, geographical distribution, chemical constituent and medicinal properties of each species is discussed. Despite the rich ethno-medicine knowledge behind the traditional uses of climber plants, the current scientific evidence to support these claims remains scant. More research is still needed to validate the medicinal aspects, beginning by increasing the understanding of the biological actions of the climber plants.
... For instance, numerous plants in the Brassicaceae family such as Arabidopsis thaliana and Brassica oleracea cultivars have been stated to store pentacyclic triterpenoids such as β-amyrin, α-amyrin, and lupeol [6][7][8][9][10]. Furthermore, the partners of the Brassicaceae family, other plants of diverse phylogenetic origin such as grape (Vitis vinifera) [11], castor bean (Ricinus communis) [12], olive (Olea europaea) [13], tomato (Solanum lycopersicum) [14], and soybean (Glycine max) [15] are well-known to collect oleanane, ursane, and lupane type aglycones. ...
Cyclization of 2,3-oxidosqualene by different oxidosqualene cyclase (OSC) genes is responsible for sapogenin heterogeneity. The very first phase is the conversion of 2,3-oxidosqualene into β-amyrin by β-amyrin synthase (BAS) gene, a member of OSC family, in soy saponin biosynthesis pathway. This paper reports the identification of a new BAS gene (GmBAS3) and its expression pattern in soybean (Glycine max (L.) Merr.). GmBAS3 gene was identified by PCR/RACE method with an open reading frame of 2286 bp nucleotides encoding a 762 amino acid long protein devouring a characteristic QW motif repeated five times and DCTAE motif. GmBAS3 shared 96 and 92% homology with Glycyrrhiza uralensis BAS and Lotus japonicus putative BAS respectively. Expression of the gene was detected by RT-PCR in regard to seedlings age and tissue type. A spatio-temporal expression of GmBAS3 was found in 21-day-old seedlings in the hypocotyls, young leaves and mature leaves but not observed in stem and root tissues. No expression was perceived in 10-day-old seedling. This study also support the premise that β-amyrin synthesis hang on more than one type of BAS genes with there expression in different plant parts at different times.
... Raisins are dried grapes, the fruits of Vitis vinifera L. (Vitaceae) and produced in most geographic regions of the world. The producing countries are the United States, Iran, Turkey, China, Chile, South Africa, Greece, Australia and Uzbekistan (Rivero-Cruz et al. 2008;Williamsona & Carughi 2010;Ghrairia et al. 2013). ...
The occurrence of ochratoxin A (OTA) in dried grapes was surveyed in this study. Sixty six samples of dried grapes (40 currants, 16 sultanas and 10 raisins) were collected from dried grapes factories in Hamadan province, Iran, from October 2012 to March 2013. High-performance liquid chromatography (HPLC) was used to determine OTA in these samples. Ochratoxin A was detected in 23 (57.5%) currants, 10 (62.5%) sultanas and 6 (60%) raisins samples. Levels in 5 samples exceeded the Institute of Standards and Industrial Research of Iran (ISIRI) maximum level of 5 µg/kg. However, OTA content in none of the samples exceeded the maximum limit prescribed in the European Union regulations, which is 10 µg/kg. The obtained data contribute to information on OTA levels in Iranian dried grapes.
... Eight compounds in raisin make antibacterial effects including oleanolic acid, oleanolic aldehyde, linoleic acid, linolenic acid, betulin, betulinic acid, 5-(hydroxymethyle)-2-furfural and sitosterol that antibacterial activity of oleanolic acid is more than other compounds. Antimicrobial activity of mentioned compounds leads to limit the growth of some bacteria such as Coliforms (Rivero-cruz et al., 2008). Low moisture of raisin contributes to stimulate the growth of molds and yeasts (Hakobyan et al., 2010). ...
Raisins are one of the dried fruit products made from grapes. In this study, microbial quality of raisin samples produced by shade drying and solar drying methods has investigated. The results indicate that Salmonella and E.coli were not detected in both samples but Coliforms significantly have observed. Molds and yeasts were in higher levels in raisin samples. Also, fungi counts in shade drying method found in lower level (mold
2.59 Mean Log Cfu/g, yeast 2.05 Mean Log Cfu/g) in compared with solar drying method (mold 2.88 Mean Log Cfu/g, yeast 2.48 Mean Log Cfu/g) because of SO2 treatment, without exposure to environment contamination and lower process time in shade drying method. Shade drying method is suggested as a better system to produce raisin but harmful effects of residues of sulphur after shade drying process cannot be forgotten.
... [12] Dried fruits have been studied by many researchers. [13][14][15] Raisins (Vitis vinifera L.) are obtained by dehydrating grapes, usually with sun exposure or tunnel drying. [16][17][18] Solar drying is the most ancient and most widely used method in Tunisia. ...
Four raisin (Vitis vinifera L.) varieties, Chriha, Razeki, Assli, and Meski, were evaluated for total phenolic content, total o-diphenol content, total flavonoid content, total condensed tannin, total carotenoid content, and total anthocyanin content. Antioxidant potential was assessed by three assays: 2,2-Diphenyl-1-Picrylhydrazyl and 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid radical scavenging capacity and ferric reducing power. Individual phenolic profiles were determined by high-performance liquid chromatography. The results revealed that the four raisin varieties had considerable phenolic content and antioxidant activity. Chriha had the highest total phenolic content (534.2 mg/g dry weight) while Meski had high total condensed tannin (208.6 mg CEQ/g dry weight), TAC (137 mg/100 g dry weight), total o-diphenol content (115.8 mg/g dry weight), total flavonoid content (93 mg CEQ/g dry weight), and total carotenoid content (33 mg/100 g dry weight). There were significant differences in phenolic content among the four varieties (p < 0.05). Meski had the highest 2,2-Diphenyl-1-Picrylhydrazyl scavenging capacity, while Chriha had adequate reducing power and 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid scavenging capacity. The individual phenolic compounds (2.96-6.54 mg/g dry weight) were variety-dependent.
... They are well known for their hepatoprotective effects against both acute chemically induced liver injury and chronic liver fibrosis and cirrhosis [1]. Moreover, a variety of novel pharmacological effects produced by these triterpenoids have been reported, such as antioxidant [2,3], anti-inflammatory [4,5], antitumour [6,7], anti-HIV [8], antimicrobial [9,10], gastroprotective [11] and the antiobese potential [12,13]. Given their occurrence at low levels in many herbal medicines and very low UV absorptions, the determination of OA and UA has attracted increasing attentions in research of traditional Chinese medicinal herbs (CMHs). ...
... For a long time, the adverse effects of HMF on the growth of microorganisms have been noticed. HMF has been confirmed as one of active constituents in Thompson seedless raisins for restraining Streptococcus mutans and Porphyromonas gingivalis, two oral pathogens associated with caries and periodontal disease ( Rivero-Cruz et al., 2008). As such, antibacterial compounds derived from plants have been suggested as alternative options or may be a better choice for dental plaque and oral disease control when compared to commonly used chemicals. ...
Background: Chinese herbal medicines (CHMs) must be processed before being prescribed to patients. During the processing, some CHMs became brown and as such 5-hydroxymethyl furfural (HMF) generated. Increasing attention is being paid to the safety and effectiveness of HMF.Methods: This paper summarized previous and recent reports on HMF formation, its presence in CHMs, its metabolism and bioactivities, together with its implications for CHMs.Results: HMF had been detected in 41 CHMs, and increased by about 12~1200 times after heat processing in some CHMs. Current data showed that HMF has limited genotoxicity but various bioactivities, such as anti-oxidative, anti-apoptotic, anti-inflammatory, anti-hypoxic, anti-microbial, and inhibiting sickling of red blood cells.Conclusion: Accumulation of HMF during heat processing of CHMs indicates that Maillard reaction and caramelization occurred. The other products of the two browning reactions deserve more attention in the following investigations on heat processed CHM.
Bacterial infections are among the most common diseases worldwide, accounting for approximately 15% of all deaths globally. These infections can affect various body parts, including the respiratory, gastrointestinal, and urinary systems. To treat bacterial infections, numerous existing and new compounds are used. Oleanolic acid (OA) and its derivatives have gained attention via their potential therapeutic properties, particularly in managing bacterial infections. Oleanolic acid derivatives are chemical compounds derived from oleanolic acid, a naturally occurring triterpenoid found in various plants. Studies have shown that these compounds have antimicrobial activity against several types of bacteria. Due to the overuse of antibiotics during the COVID-19 pandemic, many people have become resistant to existing antibiotics, making the need for alternative and effective antibiotics more critical than ever before. Oleanolic acid and its derivatives offer a promising avenue for developing new antibacterial agents. By synthesizing and modifying the chemical structures of these compounds, researchers can * Rishabh Chalotra, Muhammed Amanat, Meenakshi Dhanawat et al. 48 optimize their efficacy and specificity as potent antibacterial agents. However, despite many pre-clinical studies, there are currently negligible clinical trials using these compounds for antibacterial responses. The purpose of this book part is to provide a summary of current study on the use of oleanolic acid and its derivatives for the therapy of bacterial infections, as well as future prospects. Researchers working in this field could find these areas of interest.
Hydroxymethyl furfural (HMF) is one of important intermediates formed in Maillard reaction and caramelization. It was found that HMF existed in many Chinese herbal medicines (CHMs) and accumulated during CHM processing. In recent years, increasing attention has been paid to its safety and actions in CHMs, which has led to many reports about different aspects of HMF. In this paper, previous and recent studies on HMF formation, its presence in CHMs, its metabolism and bioactivities, together with its implications for CHMs were summarized, with the purpose of contributing to a better understanding of CHMs.
Coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has spread worldwide. There is no effective medication for COVID-19 as of now, so it would be good to take preventive measures that not only boost our immunity but also fight against infections in this perilous time. The utilization of traditional Chinese medicine in China to treat COVID-19 patients sets the prototype demonstrating that traditional medicines can contribute to prevention and treatment successfully. In India, the Ministry of AYUSH (Ayurveda, Yoga, Unani, Siddha, Homeopathy) released a self-care advisory during the COVID-19 crisis as a preventive aspect. This review article discusses the therapeutic potential and clinical relevance of some herbs [(Tulsi (Ocimum sanctum), Haridra (Curcuma longa), Tvaka (Cinnamon), Maricha (Piper longum), Shunthi (Zingiber officinale), Munakka (Dried grapes), Lavang (Syzigiumaromaticum), Pudina (Mentha arvensis), and Ajwain (Trachyspermum ammi)] advised by AUYSH to take during COVID-19 infection. They are effective in COVID-19 management, therefore, authors have discussed their detailed traditional uses as therapeutics and spotted scientific insight and clinical significance of the above-mentioned herbs along with their mechanistic viewpoint, adequately, on a single platform. Provided information could be a treasure to open up a new research arena on natural products to manage human health crises effectively, caused not only by COVID-19 but also by other infectious diseases.
Colorectal cancer is one of the major causes of cancer-related mortality in humans in both developed and developing countries. Dietary patterns influence the risk of colon cancer development, while plant-derived foods have gained great interest, due to the high content of antioxidants. Corinthian raisins (Currants, CR) and Sultanas (S) (Vitis vinifera L., Vitaceae) are dried vine fruits produced in Greece with many culinary uses in both the Mediterranean and the Western nutrition. In the present study, we investigated the effects of CR and S on human colon cancer cells. Methanol extracts of CR and S were used at different concentrations. The total polyphenol content and anti-radical activity were measured by Folin–Ciocalteu and DPPH, respectively. Antioxidant, anti-inflammatory and anti-proliferative effects on HT29 cell culture were evaluated. All extracts exhibited DPPH˙ scavenging activity in a dose-dependent manner. Both products suppressed cell proliferation, while the levels of glutathione and cyclooxygenase 2 were significantly decreased. A significant reduction in IL-8 levels and NF-kappaB p65 activation was also observed. Both antioxidant and anti-inflammatory effects were dependent on the duration of exposure. Results indicate that the methanol extracts of CR and S exhibit anti-radical activity in vitro, as well as cancer preventive efficacy on colon cancer cells, with S having slightly higher activity. The beneficial properties of these unique dried grapes are attributed to their high content of phenolic compounds.
A new bioactive naphthalene glucoside, named neanoside C (1), was isolated from the aerial part of Neanotis wightiana. The structure of neanoside C (1) was elucidated as 1,4-dihydroxy-2-(6′-Omethylglucopyranosyloxymethyl)-naphthalene-3-vinyloxyglucopyranoside by interpretation of the spectroscopic data, including 2D NMR and chemical studies. Neanoside C (1) was further subjected to screening for anticancer potential using MTT based cytotoxicity assay, LDH leakage assay, and estimation of intracellular ROS production in two human breast cancer cell line. The compound exhibited promising anti-proliferative and cytotoxic effect against MCF-7 and MDA-MB-231 cell lines with an IC50 value of 22.77 nM and 35.71 nM, respectively. Neanoside C (1) also exhibited concentration-dependent intracellular LDH leakage and ROS production.
Objectives: Polyphenols in edible berries and tea plant (Camellia sinensis) suppressed virulence factors of oral pathogens. We investigated if the commercially marketed plant polyphenols-containing beverages inhibited growth and biofilm formation of Streptococcus mutans and children’s dental plaque. Methods: Supragingival plaque collected from 16 children (7–11 years) were suspended in TSB for testing. Test beverages included 26 marketed packaged teas, ready-to-drink bottled raspberry flavored teas and cranberry juice cocktails with and without added sugars. Their effects on in vitro growth and biofilm formation of S. mutans and children’s plaque bacteria were determined after 24–48 h at 37 °C anaerobically in CDM with or without sucrose. Results: Brewed infusions from black, green and cinnamon or raspberry flavored teas bags inhibited growth and biofilm formation of children’s plaque bacteria. Compared to controls, bottled raspberry flavored teas and cranberry juice cocktails significantly inhibited growth and biofilm formation of test bacteria. Added sugar did not significantly impact the inhibition (p > 0.05). Biofilms formed in these beverages were loosely attached and easily dislodged from surfaces. Conclusions: Beverages rich in antimicrobial plant polyphenols reduce plaque adherence, may benefit oral health and are preferred over other sugary beverages. The concept of oral diseases prevention using natural foods/diet is innovative, practical and acceptable.
Periodontal diseases, such as gingivitis and periodontitis, are inflammatory diseases triggered by pathogenic bacteria that lead to damage of the soft tissue and bone supporting the teeth. Amongst the identified oral periodontopathogenic bacteria, Porphyromonas gingivalis is able to enhance oral dysbiosis, which is an imbalance in the beneficial commensal and periodontal pathogenic bacteria that induces chronic inflammation. Given the critical role of oral pathogenic bacteria like P. gingivalis in the pathogenesis of periodontitis, local and/or systemic antibacterial therapy has been suggested to treat this disease, especially in its severe or refractory forms. Nevertheless, the majority of the antibacterial agents currently used for the treatment of periodontal diseases are broad-spectrum, which harms beneficial bacterial species that are critical in health, inhibit the growth of pathogenic bacteria, contribute in protecting the periodontal tissues to damage and aid in its healing. Thus, the development of more effective and specific antibacterial agents is needed to control oral pathogens in a polymicrobial environment. The strategies for the development of novel antibacterial agents include natural product isolation as well as synthetic and semi-synthetic methodologies. This review presents an overview of the periodontal diseases gingivitis and periodontitis along with current antibacterial treatment options (i.e., classes of antibacterial agents and the mechanism(s) of resistance that hinder their usage) used in periodontal diseases that specifically target oral pathogens such as P. gingivalis. In addition, to help medicinal chemists gain a better understanding of potentially promising scaffolds, this review provides an in-depth coverage of the various families of small molecules that have been investigated as potential anti-P. gingivalis agents, including novel families of compounds, repositioned drugs, as well as natural products.
Dried fruits are relatively cheap and easy to store, and for that reason, they become essential components of food, beverages, and recipes. This healthy alternative to sweet snacks can be a valuable source of antioxidants and micronutrients, containing vitamins, folate, potassium, magnesium, and also fiber, whereas these products are low in total fat, saturated fatty acids, and sodium. Raisins are the most popular fruit in the Mediterranean diet and possess high antioxidant properties due to their chemical components. They contain phenolic acids and flavonols as well as catechins and anthocyanins (red grapes). Therefore they are considered to be one of the nutrient-rich foods, especially advantageous for human health and well-being. Several studies report health benefits of raisins, including a possible contribution in the treatment of obesity and diabetes, gastric cancer prevention, dental decay reduction, and decrease of important risk factors for cardiovascular diseases—systolic pressure, total cholesterol, and LDL cholesterol. However, some amounts of harmful mycotoxins and toxic metals could be found in raisins and other dried fruits. Therefore the continuous quality control monitoring of dried fruits should be required.
Background and Objective: Streptococcus mutans is a major causative pathogen of dental caries, which is a multifactorial oral infection resulting in progressive tooth destruction. Several medicinal plants, including Morus alba (mulberry tree) have been used in folk medicine for the treatment and prevention of dental caries. The objectives of this study were to evaluate the antibacterial and anti-cariogenic activities of the M. alba leaf extracts against S. mutans and to develop a chewing gum containing the extract. Materials and Methods: The MIC and MBC were determined by using broth dilution and drop plate methods, respectively. Biofilm formation and glycolytic pH drop assays were performed to evaluate the anti-cariogenic activity. High-performance liquid chromatography was used for phytochemical analysis of the extracts. The chewing gum containing the M. alba leaf ethanolic extract was prepared by varying different types and concentrations of ingredients. The freeze-thaw cycle testing was conducted to determine the stability of the developed chewing gum. Results: The ethanolic and aqueous M. alba leaf extracts possessed antibacterial activity against S. mutans with the MICs of 0.14 and 5 mg mL–1, respectively. The ethanolic extract at the sub-MICs significantly inhibited both acid production and biofilm formation of S. mutans. The phytochemical analysis showed that the concentrations of chlorogenic acid and rutin in the ethanolic extract were significantly higher than those in the aqueous extract. Two satisfactory chewing gum formulas with good stability, gum A and B, were obtained. The gum B formula was found to have the better performance. Conclusion: The results from this study demonstrated the anti-cariogenic role of M. alba leaves even at the low concentration of sub-MICs. The prepared chewing gum B formula can potentially be further developed as a medicated chewing gum for the prevention of dental caries in the near future.
Children's dental health in England has shown improvement in recent decades. However, 24.7% of 5 year-olds have obvious decay, with the average number of affected teeth being 3.4, and tooth decay is the most common reason for hospital admissions in 5–9 year-olds. Public Health England advises that foods and drinks containing free sugars are limited because of the increased risk of dental caries associated with frequent intakes. Although dried fruit contains more sugars than fresh fruit by weight due to the dehydration process, the portion size of dried fruit is 30 g compared with 80 g for fresh fruit. Additionally, these sugars are not defined as ‘free’ according to the current UK definition. However, unlike other sources of natural sugars, dried fruit is recommended to be eaten with meals only rather than as a snack because there is a supposition that it ‘sticks’ to teeth. A comprehensive review of the evidence published last year found a lack of good quality studies to support this advice. In the absence of data from intervention and cohort studies for effects of dried fruit on dental caries endpoints, studies of proxy measures of tooth demineralisation show inconsistent effects on plaque pH and acidogenicity. Measurement of net demineralisation, following consumption of raisins seven times a day for 10 days, showed comparable effects with fresh fruit and vegetables under similar conditions. Oral retention (‘sticking’) has been investigated in few subjects. The results do not demonstrate that dried fruit is worse in terms of oral clearance than alternative snack foods. More robust research with validated methods is needed before firm conclusions can be drawn about the retention of dried fruit, and hence its potential for adverse effects on teeth. This is important because eating traditional dried fruits can help towards the achievement of a number of dietary recommendations, including contributing to the 5 A DAY target and increasing fibre intake.
With recently growing health consciousness, natural materials with pharmacological actions have been increasingly attracting attention. In the dental field, materials with desirable functions, such as the inhibition of caries, have been studied, and greater importance is attached to effects on cariogenic bacteria, mutans streptococci.In this study, we focused on grapes, which contain abundant physiologically active substances, such as triterpene and polyphenols, particularly strained wine lees (pomece). Physiologically active substances were extracted from pomece, and their inhibitory activities on Streptococcus mutans (S. mutans) glucosyltransferase and growth were measured. In addition, the compositions and structures of physiologically active substances contained in pomece were clarified to investigate the possibility of pomece serving as a caries inhibitor.Pomece extract exhibited GTase and cariogenic bacterial growth inhibitory effects. On component analysis employing thin-layer chromatography and HPLC-UV, a triterpene, oleanolic acid, was present at 10% in ethanol extract of pomece before purification and 90% in a fraction showing strong activity.It was clarified that pomece extract exhibited inhibitory activities on WIG synthesis and S. mutans growth due to it containing oleanolic acid. Although it is necessary to investigate the most effective method of utilizing the extract, these activities markedly varied depending on the oleanolic acid content, suggesting that pomece extract may be utilized as a caries inhibitor.
A comprehensive review of the literature has found that the common perceptions that dried fruits are “sticky”, adhere to teeth, and are detrimental to dental health on account of their sugar content are based on weak evidence. There is a lack of good quality scientific data to support restrictive advice for dried fruit intake on the basis of dental health parameters and further research is required. A number of potentially positive attributes for dental health, such as the need to chew dried fruits which encourages salivary flow, and the presence of anti-microbial compounds and of sorbitol, also require investigation to establish the extent of their effects and whether they balance against any potentially negative attributes of dried fruit. Advice on dried fruit consumption should also take account of the nutritional benefits of dried fruit, being high in fibre, low in fat and containing useful levels of micronutrients.
This presentation provides an overview of the impact of food components and dietary factors on oral health. The protective properties of various foods, plant extracts and plant-based polyphenolic compounds on dental caries and periodontal disease are discussed. Laboratory, human, and epidemiological studies demonstrating the multiple mechanistic actions in supporting their contribution to oral health and disease prevention are summarized. The need and development of multidisciplinary research approach toward experimental designs and strategies in clinical and epidemiological studies are also emphasized.
This chapter provides a brief description of the complex grape chemistry, i.e., the great variety of metabolites synthesized by the plant and stored in different berry tissues. Health-promoting effects of grapevine products strictly depend on the potpourri of the chemicals present in grape tissues, phenylpropanoids, isoprenoids, and alkaloids, thus supporting the assumption that no particular compound is by itself responsible for the health benefits widely attributed to these plant foods and beverages. In the last decades, a lot of studies focused mainly on polyphenols, considered as the archetypes of grapevine product bioactivities. Grape seed extract shows promising efficacy against two important processes involved in cancer progression, angiogenesis and metastasis, inhibited in prostate and breast carcinoma, respectively. Because of increased metabolic activity and oxygen consumption of rapidly proliferating cells, solid tumors are likely to maintain an intratumoral hypoxic environment, which, in turn, induces a set of hypoxia-responsive genes in order to allow tumor cell adaptation. The expression of these genes is regulated by the hypoxia inducible factor, a major regulator of cellular oxygen homeostasis. Apart from the beneficial effects exerted by polyphenols, other types of tumors can benefit from regular, moderate consumption of grape products. Carcinomas of the digestive tract are common and their risk increases with age. In gastric cancer cells, resveratrol was shown to inhibit cell proliferation and to induce apoptosis.
Dental caries (tooth decay) is a chronic disease, affecting a large number of populations. The carious process affects the mineralized tissues of the teeth, enamel, dentine and cementum. It is caused by the action of microorganisms on fermentable carbohydrates in the diet. The disease is often described to be progressive and if not treated may expand in size and progress to the pulp leading to pulp inflammation thus pain and discomfort, and the end result will be loss of vitality then loss of the tooth. To promote healthy teeth, many communities have implemented the fluoridated water, a practice started during the 1940s. Other common practices include using fluoride-containing toothpaste for brushing, routine dental cleanings by a qualified practitioner and getting cavities filled. Now, an array of more natural methods are available to promote dental health, prevent tooth decay and provide relief from tooth pain and gum irritation associated with poor dental health. This review discusses about anti-cariogenic activity of raisins. Although raisins are sweet and are considered “sticky,” research imply that they do not adhere to the teeth long enough to promote dental caries formation and may help clear other cariogenic sugars from the tooth surface. © 2015, Asian Journal of Pharmaceutical and Clinical Research. All rights reserved.
This presentation provides an overview of the impact of food components and dietary factors on oral health. The protective properties of various foods, plant extracts and plant-based polyphenolic compounds on dental caries and periodontal disease are discussed. Laboratory, human, and epidemiological studies demonstrating the multiple mechanistic actions in supporting their contribution to oral health and disease prevention are summarized. The need and development of multidisciplinary research approach toward experimental designs and strategies in clinical and epidemiological studies are also emphasized.
Introduction Compositional and nutritional characteristics of dried fruits Phytochemicals in dried fruits Beneficial health effects of dried fruits Commercial products and industrial applications of dried fruits Conclusions References
Oral diseases, including dental caries, periodontal disease, and tooth loss, affect the majority of the population and can affect a person's overall health. Raisins contain polyphenols, flavonoids, and high levels of iron that may benefit human health. However, their oral health benefits are less well understood. We hypothesized that raisins contain antimicrobial phytochemicals capable of suppressing oral pathogens associated with caries or periodontal diseases and thus benefit oral health. Compared with commercial bran flakes or raisin bran cereal, a lower plaque pH drop was noted in children who consumed a raisin and bran flake mixture when no sugar was added (P < 0.05). Grape seed extract, high in proanthocyanidins, positively affected the in vitro demineralization and/or remineralization processes of artificial root caries lesions, suggesting its potential as a promising natural agent for noninvasive root caries therapy. © 2015, Indian Journal of Public Health Research & Development..All rights reserved.
The ¹³C N.M.R. spectra of a number of substituted furans and thiophens have been determined and individual resonances assigned. The substituent effects which are comparable to those for substitutedbenzene or pyrrole derivatives are discussed. In 2,5-disubstituted compounds, some correlation of the observed resonances and values calculated from the additivity parameters is evident.
Pomace oil ('orujo' olive oil), is an olive sub-product which possesses potential beneficial components (e.g. tetra- and pentacyclic triterpenes: oleanolic and maslinic acids, erythrodiol and uvaol) to which great variety of biological effects is attributed. Pharmacological properties of oleanolic acid have been demonstrated: anti-inflammatory, antitumoral, hepatoprotective, cytotoxic, anti-diabetogenic, antibacterial and anti-HIV activities. There is scarce evidence about the pharmacological effects of these triterpenoid on vascular events; the chronic treatment of Dahl salt-sensitive hypertensive rats with these natural compounds (oleanolic and ursolic acids) prevent the development of hypertension with significant bradycardia and potent diuretic activity. In relation to erythrodiol and uvaol, only their therapeutic efficiency on different experimental models of inflammation has been reported. Moreover, uvaol plays a protective role on the oxidation of lipoproteins of low density in vitro, as well as a protective effect on induced hepatic injuries. Maslinic acid is effective in the treatment of diseases caused by agents that use the serin-protease in their mechanism of infection, like the AIDS virus and it has capacity to prevent the damage caused by the free radicals. Therefore, the intake of 'orujo' olive oil, as a source of these compounds, might be beneficial in this regard.
The composition of dental plaque formed in the presence of sucrose or glucose and fructose and its relation to cariogenicity was evaluated. Twelve adult volunteers took part in this crossover study done in three phases of 28 days each. For each phase, an acrylic resin appliance containing four human dental enamel blocks was constructed for the volunteers. Solutions containing 20% sucrose or 10% glucose + 10% fructose were dripped onto the enamel blocks 8 times a day, while in the control group no solution was used. Enamel surface and cross-sectional microhardness results showed that dental plaque formed in the presence of sucrose was more cariogenic than that formed in the presence of glucose + fructose (p<0.05). The concentration of alkali-soluble carbohydrates in dental plaque was higher in the sucrose group than in the control and glucose + fructose groups (p<0.05). Although concentrations of Ca, P and F were lower in plaque formed in the presence of sucrose than glucose + fructose and the control, significant differences (p<0.05) were only observed in relation to control. The electrophoretic profile of the matrix proteins of dental plaque showed distinct patterns when it was formed in the absence or presence of the different carbohydrates. Although the results suggest that the high cariogenicity of dental plaque formed in the presence of sucrose can be mainly explained by the high concentration of insoluble glucans of its matrix, the low inorganic concentration and its protein composition may have some contribution.
A new quassinoid, yadanziolide S (1), was isolated from the seeds of the traditional Chinese medicinal herb, Brucea javanica, along with ten known compounds, flazin, bruceine D, yadanziolide B, bruceoside A, yadanziolide S, yadanzigan, glycerol 1,3-bisoleate, azelaic acid, (+/-)-8-hydroxyhexadecanoic acid, and vanillin. Compound 1 is the first quassinoid to have been isolated from B. javanica without a methyleneoxy bridge between C-8 and C-13, and its structure was determined using spectroscopic methods, and confirmed by single-crystal X-ray diffraction. All isolates were evaluated for their potential to induce human promyelocytic leukemia (HL-60) cell differentiation, and to inhibit cyclooxygenase-1 (COX-1), -2 (COX-2), and 7,12-dimethylbenz[a]anthracene (DMBA)-induced lesions in a mouse mammary organ culture model.
The ¹³C NMR apectra of lupane-type triterpenes, lupeol (1), its acetate (2), betulin (3) and betulinic acid (4), were recorded and the signals assigned.
Nuclear magnetic resonance spectra of some common steroids with hydrocarbon side chains have been studied. The methyl regions have been factored and assigned. The results are applied to the identification of an unknown methylated steroid.
An analysis procedure for the determination of the fatty acid ester residue on processed raisins was developed. Gas chromatographic analysis of the dipping oils which were used to increase the drying rate of grapes showed the presence of two or more of the following fatty acid esters: oleate, stearate, palmitate, and linoleate, with oleate accounting for the largest percentage. The esters were removed from the raisins by extraction with chloroform and the hexane-soluble fraction which contained the esters was analyzed by gas chromatography. Grapes dipped in 0.5-6.0% water emulsions of a commercial Australian ethyl ester dipping oil produced residues on the processed raisins of 41-397 ppm of total fatty acid esters, as measured by gas chromatography.
Based on our previous finding that 3-O-acyl-betulinic and -oleanolic acids, especially the 3-O-(3',3'-dimethyl)-succinyl derivatives (2 and 4), demonstrated potent anti-HIV activity [EC50 < 0.00035 and 0.00086 M; therapeutic index (TI) > 20 000 and 22 326, respectively], several 3-O-acyl-ursolic acids were prepared and evaluated for anti-HIV activity. Ursolic acid (6) was equipotent (EC50 4.4 muM) with oleanolic acid (EC50 3.7 muM), although it was slightly toxic (IC50 14.3 CIM, TI 3.3). 3-O-Diglycoryl-ursolic acid (10) demonstrated relatively potent anti-HIV activity with an EC50 of 0.31 muM and a TI of 155.5. In contrast, 3-O-(3',3'-dimethylsuccinyl)-ursolic acid (8), which is analogous to the extremely potent anti-HIV betulinic acid and oleanolic acid derivatives 2 and 4, displayed only weak anti-HIV activity (EC50 2.1 muM, TI 23.6).
Oxidizing, phosphorus, ester and amide derivatives of oleanolic acid 1 have been prepared. The antibacterial activity of compound 1, isolated from the fruit barks of Periploca laevigata (Asclepiadaceae), and its derivatives have been tested using Tween-80 as complex agent to form a water-soluble triterpenes. The same activity of maslinic acid acetate 2, β-amyrin 3, and its acetylated derivative 3a (Fig. 1), isolated from the same source as that of oleanolic acid 1, have also been investigated. To cite this article : F. Hichri et al., C.R. Chimie 6 (2003).
An extraction method based on supercritical CO2 has been developed for the analysis of 5-hydroxymethyl-2-furaldehyde in raisins. To optimize extraction variables, a fractional factorial experimental design was applied. Six extraction variables were optimized. The organic modifier used for increasing the extraction fluid solvating power was the most important factor. Methanol as organic modifier produced 10-fold higher recoveries of 5-hydroxymethyl-2-furaldehyde than ethyl acetate. The efficiency of the organic modifier in the static extraction phase was compared with using it in the dynamic extraction phase. Repeatability of the analysis method was evaluated, which resulted in an RSD of <5%. 5-Hydroxymethyl-2-furaldehyde was quantified in raisins, and the concentration was found to be 0.128 mg/g of raisin.
The noise-decoupled and gated-decoupled 13C n.m.r. spectra of quercetin and rutin are studied and assignments are proposed. The previous assignments of carbons 2 and 4′, carbons 5 and 9, carbons 6 and 8 have been reversed.
The amino acid profile of raisins indicated that of the 2.9g amino acids per 100g dry matter of raisins, arginine was present in the greatest concentration (25%), followed by proline and glutamic acid.
Complete assignments of 1H and 13C NMR chemical shifts for oleanolic acid, 18α-oleanolic acid, ursolic acid and their 11-oxo derivatives based on 1H, 13C, 2D DQF-COSY, NOESY, HSQC, HMBC and HSQC-TOCSY experiments were achieved. Copyright © 2003 John Wiley & Sons, Ltd.
A compilation of the13C NMR data of a selected variety of naturally occurring pentacyclic triterpenoids, arranged skeletonwise, is provided. A bri
Two new saponins, α-L-rhamnopyranosyl (1 → 4) β-D-glucopyranosyl (1 → 3)sitosterol and α-L-rhamnopyranosyl (1 → 5) α-L-arabinofuranosyl (1 → 3)sitosterol, have been reported from Lindenbergia indica.
The application of a computer-assisted structure elucidation expert system, CISOC-SES, leading to the unequivocal 1H, 13C and NOE resonance assignment of betulinic acid, a biol. active triterpenoid with complicated NMR resonances, is described. The procedure consists of peak picking that is independent of background information, systematic interpretation of connectivity information from 2D NMR into bond constraints and resonance assignment based on the proposed structure. De novo structure generation based solely on the mol. formula and spectral data is also described. This application demonstrates the potential of efficient and systematic structure elucidation of natural products with modern high-resoln. NMR spectroscopy combined with artificial intelligence. [on SciFinder (R)]
The surface lipids of the grapes from varieties used for the production of Sultanas, raisins and currants were extracted with chloroform. A further separation of the extracts with light petroleum yielded the insoluble ‘hard wax’ which consists mainly of oleanolic acid, and the soluble ‘soft wax’. This fraction was separated by chromatography on aluminium oxide into the hydrocarbon, ‘ester-aldehyde’, alcohol and acid fractions. The composition of the hydrocarbon and alcohol fractions of the surface wax of fresh grapes and the composition of the saponifiable fraction of lipids from dried and processed grapes has been determined by gas/liquid chromatography. The addition of oils to dried grapes can be detected and determined by chromatography on aluminium oxide or saponification and estimation of the fatty acids.
Our laboratory has engaged in the exploration of active antimicrobial principles present in chewing sticks commonly used by the African and Middle Eastern countries as a mechanical oral hygiene aid in place of tooth brushing. During this investigation, a methanol extract from the twigs of Diospyros lycioides, a Namibia tooth cleaning stick, demonstrated antimicrobial activity against common oral pathogens including Streptococcus mutans and Porphyromonas gingivalis (MICs 2.5 and 0.156 mg/mL). Subsequent fractionation and purification of this extract led to the identification of two novel binaphathalenone glycosides: 1', 2-binaphthalen-4-one-2',3-dimethyl-1,8'-epoxy-1,4',5,5',8, 8'-hexahydroxy-8-O-beta-glucopyranosyl-5'-O-beta-xylopyranosyl(1-- >6) -beta-glucopyranoside (1) and 1',2-binaphthalen-4-one-2', 3-dimethyl-1,8'-epoxy-1,4',5,5',8,8'-hexahydroxy-5', 8-di-O-beta-xylopyranosyl(1-->6)-beta-glucopyranoside (2). Their structures were established using spectroscopic techniques. Examination of the antimicrobial activity of these two compounds revealed positive but only marginal growth inhibition against the test cariogenic pathogens, S. sanguis and Streptococcus mutans.
Earlier work in vitro showed that oleanolic acid (OA) was a potential inhibitor of insoluble glucan (ISG) synthesis from mutans streptococci (MS). In this study, two oleanolic acid-cyclodextrin inclusion compounds (OA-CDs), oleanolic acid-G1-beta-cyclodextrin (OA-G1-beta CD) and oleanolic acid-beta-cyclodextrin (OA-beta CD), were assayed for their effects on ISG synthesis from Streptococcus mutans MT8148R, and on the growth of oral bacteria. OA-beta CD inhibited ISG synthesis by 55.3 and 37.4% at 62.5 and 15.6 micrograms/ml of OA, respectively. Both OA-CDs inhibited the growth of MS, S. sanguis, and S. salivarius at 4 to 8 micrograms/ml of OA. The anticariogenic effect of the OA-beta CD was examined in a rat-caries model. Rats in the infected control groups showed the highest caries score. The infected treatment group B (0.5% OA in diet) showed lower scores than the control group. These results suggest that OA-beta CD is a potential anti-caries agent.
Arnica and propolis have been used for thousands of years in folk medicine for several purposes. They possess several biological activities such as anti-inflammatory, antifungal, antiviral and tissue regenerative, among others. Although the antibacterial activity of propolis has already been demonstrated, very few studies have been done on bacteria of clinical relevance in dentistry. Also, the antimicrobial activity of Arnica has not been extensively investigated. Therefore the aim here was to evaluate in vitro the antimicrobial activity, inhibition of adherence of mutans streptococci and inhibition of formation of water-insoluble glucan by Arnica and propolis extracts. Arnica montana (10%, w/v) and propolis (10%, w/v) extracts from Minas Gerais State were compared with controls. Fifteen microorganisms were used as follows: Candida albicans--NTCC 3736, F72; Staphylococcus aureus--ATCC 25923; Enterococcus faecalis--ATCC 29212; Streptococcus sobrinus 6715; Strep. sanguis--ATCC 10556; Strep. cricetus--HS-6; Strep. mutans--Ingbritt 1600; Strep. mutans--OMZ 175; Actinomyces naeslundii--ATCC 12104, W 1053; Act. viscosus OMZ 105; Porphyromonas gingivalis; Porph. endodontalis and Prevotella denticola (the last three were clinical isolates). Antimicrobial activity was determined by the agar diffusion method and the zones of growth inhibition were measured. To assess cell adherence to a glass surface, the organisms were grown for 18 h at 37 degrees C in test-tubes at a 30 degree angle. To assay water-insoluble glucan formation, a mixture of crude glucosyltransferase and 0.125 M sucrose was incubated for 18 h at 37 degrees C in test-tubes at a 30 degree angle. Arnica and propolis extracts (20 microl) were added to these tubes to evaluate the % of inhibition of cell adherence and water-insoluble glucan formation. The propolis extract significantly inhibited all the microorganisms tested (p < 0.05), showing the largest inhibitory zone for Actinomyces spp. The Arnica extract did not demonstrate significant antimicrobial activity. Cell adherence and water-insoluble glucan formation were almost completely inhibited by the propolis extract at a final concentration of 400 microg/ml and 500 microg/ml, respectively. The Arnica extract showed slight inhibition of the adherence of the growing cells (19% for Strep. mutans and 15% for Strep. sobrinus) and of water-insoluble glucan formation (29%) at these same concentrations. Thus, the propolis extract showed in vitro antibacterial activity, inhibition of cell adherence and inhibition of water-insoluble glucan formation, while the Arnica extract was only slightly active in those three conditions.
The twigs of Diospyros lycioides, a plant commonly known as "muthala", are frequently used as chewing sticks for the cleaning of teeth by rural and urban people in Namibia. Preliminary studies showed that a methanol extract of D. lycioides inhibited growth of selected oral pathogens. Subsequent bioassay-guided fractionation led to the isolation of four novel bioactive naphthalene glycosides, diospyrosides A, B, C, and D (1-4), and two known bioactive naphthoquinones, juglone (5) and 7-methyljuglone (6). The structures of the new compounds were elucidated using spectroscopic techniques including 1D and 2D NMR. These compounds inhibited the growth of oral cariogenic bacteria (Streptococcus mutans and Streptococcus sanguis) and periodontal pathogens (Porphyromonas gingivalis and Prevotella intermedia) at minimum inhibitory concentrations ranging from 0.019 to 1.25 mg/mL. Juglone exhibited the strongest inhibitory activity among these compounds.
Dietary phytoestrogens such as the isoflavones daidzein and genistein are thought to protect against chronic diseases that are common in Western societies, such as cancer, osteoporosis, and ischemic heart disease. In addition, there are concerns regarding the deleterious effects of hormone-like compounds, especially with respect to the development of infants. However, there is little information regarding the phytoestrogen content of foods, and therefore epidemiologic investigations of phytoestrogens are limited. As part of a study quantifying the consumption of phytoestrogens, the objective of this work was to assess the daidzein and genistein content of fruits and nuts commonly eaten in Europe. Eighty different fruits and nuts were sampled, prepared for eating, and freeze-dried. Daidzein and genistein were extracted from the dried foods, and the two isoflavones were quantified after hydrolytic removal of any conjugated carbohydrate. Completeness of extraction and any procedural losses of the isoflavones were accounted for using synthetic daidzin (7-O-glucosyl-4'-hydroxyisoflavone) and genistin (7-O-glucosyl-4'5-dihydroxyisoflavone) as internal standards. Of the 80 foods assayed, 43 contained no detectable daidzein or genistein, at a limit of quantification of 1 microg/kg dry weight of food. Nine foods contained more than 100 microg of the two isoflavones combined per kilogram wet weight, and 28 contained less than this amount. Currants and raisins were the richest sources of the isoflavones, containing 2,250 microg and 1,840 microg of the two isoflavones combined per kilogram of wet weight of food. Although fruits and nuts are not as rich in isoflavone phytoestrogens as are soy and other legumes, this is the first documentation of levels of daidzein and genistein occurring in these foods.
The polyphenolics of raisins were extracted, separated by HPLC, and characterized by their UV-vis spectra, and their concentrations measured. Color measurements and browning indices were also determined. Samples (n = 20) included sun-dried, dipped, and golden raisins. Comparisons were also made with fresh and frozen Thompson Seedless grapes. Golden raisins (which are treated with SO(2)) had the highest amount of hydroxycinnamic acids and the highest lightness values. In comparison with fresh grapes, percent losses of the two major hydroxycinnamics (caftaric and coutaric acids) in sun-dried, dipped, and golden raisins were on the order of 90%. Flavonols were not influenced by processing as much as hydroxycinnamics, while procyanidins and flavan-3-ols were completely degraded in all raisin samples. Formation of hydroxymethylfurfural and loss of amino acids in sun-dried and dipped raisins are ascribed to Maillard browning reactions.
Based on our previous finding that 3-O-acyl-betulinic and -oleanolic acids, especially the 3-O-(3',3'-dimethyl)-succinyl derivatives (2 and 4), demonstrated potent anti-HIV activity [EC(50) < 0.00035 and 0.00086 microM; therapeutic index (TI) > 20 000 and 22 326, respectively], several 3-O-acyl-ursolic acids were prepared and evaluated for anti-HIV activity. Ursolic acid (6) was equipotent (EC(50) 4.4 microM) with oleanolic acid (EC(50) 3.7 microM), although it was slightly toxic (IC(50) 14.3 microM, TI 3.3). 3-O-Diglycoryl-ursolic acid (10) demonstrated relatively potent anti-HIV activity with an EC(50) of 0. 31 microM and a TI of 155.5. In contrast, 3-O-(3', 3'-dimethylsuccinyl)-ursolic acid (8), which is analogous to the extremely potent anti-HIV betulinic acid and oleanolic acid derivatives 2 and 4, displayed only weak anti-HIV activity (EC(50) 2.1 microM, TI 23.6).
An extraction method based on supercritical CO(2) has been developed for the analysis of 5-hydroxymethyl-2-furaldehyde in raisins. To optimize extraction variables, a fractional factorial experimental design was applied. Six extraction variables were optimized. The organic modifier used for increasing the extraction fluid solvating power was the most important factor. Methanol as organic modifier produced 10-fold higher recoveries of 5-hydroxymethyl-2-furaldehyde than ethyl acetate. The efficiency of the organic modifier in the static extraction phase was compared with using it in the dynamic extraction phase. Repeatability of the analysis method was evaluated, which resulted in an RSD of <5%. 5-Hydroxymethyl-2-furaldehyde was quantified in raisins, and the concentration was found to be 0.128 mg/g of raisin.
Thirteen oleanolic acid derivatives were prepared and evaluated for anti-HIV activity in H9 lymphocytes. Saturating the C(12)-C(13) double bond and converting the C(17)-carboxyl group to an aminomethyl group led to compounds 13-15 and 19-20, respectively, which showed improved anti-HIV activity. Compound 15 was the most potent derivative with EC(50)=0.0039 microg/mL and TI=3570.
The use of and search for drugs and dietary supplements derived from plants have accelerated in recent years. Ethnopharmacologists, botanists, microbiologists, and natural-products chemists are combing the Earth for phytochemicals and "leads" which could be developed for treatment of infectious diseases. While 25 to 50% of current pharmaceuticals are derived from plants, none are used as antimicrobials. Traditional healers have long used plants to prevent or cure infectious conditions; Western medicine is trying to duplicate their successes. Plants are rich in a wide variety of secondary metabolites, such as tannins, terpenoids, alkaloids, and flavonoids, which have been found in vitro to have antimicrobial properties. This review attempts to summarize the current status of botanical screening efforts, as well as in vivo studies of their effectiveness and toxicity. The structure and antimicrobial properties of phytochemicals are also addressed. Since many of these compounds are currently available as unregulated botanical preparations and their use by the public is increasing rapidly, clinicians need to consider the consequences of patients self-medicating with these preparations.
Two new C-methyl flavonoids, 6,8-di- C-methylluteolin 7-methyl ether (1) and 6- C-methylluteolin 7-methyl ether (2), were isolated from a commercially available sample of the roots of Hydrastis canadensis, along with seven known compounds, berberine (3), beta-hydrastine (4), canadine (5), canadaline (6), isocorypalmine (7), canadinic acid (8), and beta-sitosterol 3- O-beta- D-glucoside (9). The structures of the new compounds 1 and 2 were elucidated on the basis of their spectral data including 1D and 2D NMR techniques. Of these isolates, berberine (3) and, to a lesser extent, 1 and 2, showed antimicrobial activity when evaluated against the oral pathogens Streptococcus mutans and Fusobacterium nucleatum. Berberine (3) exhibited an additive antimicrobial effect when tested against S. mutans in combination with 1.
Bioassay-guided isolation and purification of hexane and ethyl acetate extracts of Cabernet Sauvignon grape skin yielded nine compounds (1-9), which were identified as beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside (1), beta-sitosterol (2), beta-sitosterol-3-O-beta-D-glucoside (3), oleanolic acid (4), oleanolic aldehyde (5), resveratrol (6), (+)-epsilon-viniferin (7), (-)-catechin (8), and 1-triacontanol (9). The structures of these compounds were established by spectroscopic methods. The compounds were assayed for insulin production using an INS-1 cell assay. In a dose-response study, compound 4 stimulated insulin production of INS-1 cells by 20.23, 87.97, 1.13, and 6.38 ng of insulin/mg of protein at 6.25, 12.5, 25, and 50 microg/mL, respectively. This trend was similar to the dose-dependent insulin production of INS-1 cells by glucose. Compound 5 also showed a dose-dependent insulin production in this assay. The isolated compounds were also assayed for cyclooxygenase-1 and -2 (COX) enzyme inhibitory activities. At 100 microg/mL, compounds 2, 3, and 4 inhibited the COX-2 enzyme by 11, 12, and 10%, respectively, but did not show activities on the COX-1 enzyme. Compounds 6, 7, and 8 at 100 microg/mL inhibited the COX-1 enzyme by 98, 99, and 98%, respectively, and the COX-2 enzyme by 0, 47, and 72%, respectively. This is the first report of beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside (1) from grape skin and insulin secretion activities of compounds 4 and 5.
From the roots of Glycyrrhiza uralensis, two new pterocarpenes, glycyrrhizol A (1) and glycyrrhizol B (2), along with four known isoflavonoids, 5-O-methylglycryol (3), isoglycyrol (4), 6,8-diisoprenyl-5,7,4'-trihydroxyisoflavone (5), and gancaonin G (6), were isolated using a bioassay-guided fractionation method. The structures of the new compounds (1and 2) were elucidated by spectroscopic data interpretation. The known compounds (3-6) were identified by comparison of their spectroscopic data with reported values in the literature. Glycyrrhizol A (1) and 6,8-diisoprenyl-5,7,4'-trihydroxyisoflavone (5) exhibited potent antibacterial activity against Streptococcus mutans with minimum inhibitory concentrations of 1 and 2 microg/mL, respectively, while glycyrrhizol B (2) and gancaonin G (6) showed more moderate activity.
Dadzein and genistein content of fruits and nuts
- J Liggins
- L J C Bluck
- S Ruswick
- C Atkinson
- W A Coward
- S Bingham
Liggins, J., Bluck, L.J.C., Ruswick, S., Atkinson, C., Coward, W.A., Bingham, S., 2000. Dadzein and genistein content of fruits and nuts. J. Nutr. Biochem. 11, 326–331.
Carbon-13 NMR spectra of quercetin and rutin
- Lallemand
Computer-assisted structure elucidation: application of CISOC-SES to the resonances assignment and structure generation of betulinic acid
- Peng