Pentacyclic triterpene distribution in various plants - rich sources for a new group of multi-potent plant extracts.
TL;DR: Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark display various pharmacological effects while being devoid of prominent toxicity and are promising leading compounds for the development of new multi-targeting bioactive agents.
Abstract: Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.
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TL;DR: The chemical composition, abundance and biological activities of triterpenoids occurring in cuticular waxes of some economically important fruits, like apple, grape berry, olive, tomato and others, are described in this review.
Abstract: The health benefits associated with a diet rich in fruit and vegetables include reduction of the risk of chronic diseases such as cardiovascular disease, diabetes and cancer, that are becoming prevalent in the aging human population. Triterpenoids, polycyclic compounds derived from the linear hydrocarbon squalene, are widely distributed in edible and medicinal plants and are an integral part of the human diet. As an important group of phytochemicals that exert numerous biological effects and display various pharmacological activities, triterpenoids are being evaluated for use in new functional foods, drugs, cosmetics and healthcare products. Screening plant material in the search for triterpenoid-rich plant tissues has identified fruit peel and especially fruit cuticular waxes as promising and highly available sources. The chemical composition, abundance and biological activities of triterpenoids occurring in cuticular waxes of some economically important fruits, like apple, grape berry, olive, tomato and others, are described in this review. The need for environmentally valuable and potentially profitable technologies for the recovery, recycling and upgrading of residues from fruit processing is also discussed.
196 citations
Cites background or methods from "Pentacyclic triterpene distribution..."
...2008), and accelerated solvent extraction (ASE) of dried peel with ethyl acetate (with a yield ranging from 0.2 to 2.1 % for 11 cultivars tested; Jäger et al. 2009)....
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...triterpenoids, point to fruit peels as a promising and highly available source material (Beindorff et al. 2001; Jäger et al. 2009)....
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...Apple peel has since been frequently recommended as a source of ursolic acid that may be utilized for various purposes (Beindorff et al. 2001; Glinsky and Branly 2001; Jäger et al. 2009)....
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...…anticoagulant and anticarcinogenic properties, combined with relatively low toxicity (Akihisa et al. 2001; Patočka 2003; Liu 2005; Dzubak et al. 2006; Sun et al. 2006; Jäger et al. 2009; Kuo et al. 2009; Rezanka et al. 2009; Wolska et al. 2010; Bishayee et al. 2011; Thoppil and Bishayee 2011)....
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...Screens of various plant tissues to identify those that are rich in triterpenoids, point to fruit peels as a promising and highly available source material (Beindorff et al. 2001; Jäger et al. 2009)....
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TL;DR: It is suggested that oleanolic acid and its derivatives are important candidates in the search for alternative therapy in the treatment and management of chronic diseases.
Abstract: The increasing demand for natural products as an alternative therapy for chronic diseases has encouraged research into the pharmacological importance of bioactive compounds from plants. Recently, there has been a surge of interest in the therapeutic potential of oleanolic acid (OA) in the prevention and management of chronic diseases. Oleanolic acid is a pentacyclic triterpenoid widely found in plants, including fruits and vegetables with different techniques and chromatography platforms being employed in its extraction and isolation. Several studies have demonstrated the potential therapeutic effects of OA on different diseases and their symptoms. Furthermore, oleanolic acid also serves as a framework for the development of novel semi-synthetic triterpenoids that could prove vital in finding therapeutic modalities for various ailments. There are recent advances in the design and synthesis of chemical derivatives of OA to enhance its solubility, bioavailability and potency. Some of these derivatives have also been therapeutic candidates in a number of clinical trials. This review consolidates and expands on recent reports on the biological effects of oleanolic acid from different plant sources and its synthetic derivatives as well as their mechanisms of action in in vitro and in vivo study models. This review suggests that oleanolic acid and its derivatives are important candidates in the search for alternative therapy in the treatment and management of chronic diseases.
192 citations
Cites background from "Pentacyclic triterpene distribution..."
...Apple, loquat, grape, elderberry and sage are some of the fruit plants in which oleanolic acid has also been detected and isolated [20,25]....
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...Pentacyclic triterpenes including OA are widespread in the fruits, leaves and stem bark of various edible and medicinal plants [20]....
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TL;DR: Until now very few clinical studies have been concerned with the application of triterpenes in treating diabetes, but due to their great therapeutic potential, these compounds deserve special attention.
Abstract: Diabetes mellitus is a chronic metabolic disease which is a serious global problem. In 2010 an estimated 285 million people had diabetes and within the next 20 years this value is expected to almost double. Many antidiabetic therapies focus on improving insulin sensitivity, increasing insulin production, and/or decreasing the level of blood glucose. Although a number of synthetic medicines are available, drugs of natural origin have aroused great interest. Triterpenes seem to demonstrate adequate properties. Many experiments have shown that these compounds have several antidiabetic mechanisms. They can inhibit enzymes involved in glucose metabolism, prevent the development of insulin resistance and normalize plasma glucose and insulin levels. These natural compounds, in contrast to synthetic drugs, apart from producing a hypoglycemic effect have also been found to manifest hypolipidemic and anti-obesity activity. Triterpenes are also promising agents in the prevention of diabetic complications. They have strong antioxidant activity and inhibit the formation of advanced glycation end products, implicated in the pathogenesis of diabetic nephropathy, embryopathy, neuropathy or impaired wound healing. Until now very few clinical studies have been concerned with the application of triterpenes in treating diabetes. However, due to their great therapeutic potential, these compounds deserve special attention.
186 citations
Cites background from "Pentacyclic triterpene distribution..."
...Triterpenes, especially pentacyclic ones, represent secondary metabolites that are widely distributed in the plant kingdom and found in leaves, stem bark, fruits and roots (Jäger et al. 2009)....
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...Triterpenes, especially pentacyclic ones, represent secondary metabolites that are widely distributed in the plant kingdom and found in leaves, stem bark, fruits and roots (Jäger et al. 2009)....
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TL;DR: The management of type 2 diabetes requires an integrated approach, which includes the early intervention to prevent or delay the disease progression, and the use of therapies to control glycemia and lipidemia in its late stages.
Abstract: Oleanolic acid (OA), a natural component of many plant food and medicinal herbs, is endowed with a wide range of pharmacological properties whose therapeutic potential has only partly been exploited until now. Throughout complex and multifactorial mechanisms, OA exerts beneficial effects against diabetes and metabolic syndrome. It improves insulin response, preserves functionality and survival of β-cells, and protects against diabetes complications. OA may directly modulate enzymes connected to insulin biosynthesis, secretion, and signaling. However, its major contributions appear to be derived from the interaction with important transduction pathways, and many of its effects are consistently related to activation of the transcription factor Nrf2. Doing that, OA induces the expression of antioxidant enzymes and phase II response genes, blocks NF-κB, and represses the polyol pathway, AGEs production, and hyperlipidemia. The management of type 2 diabetes requires an integrated approach, which includes the early intervention to prevent or delay the disease progression, and the use of therapies to control glycemia and lipidemia in its late stages. In this sense, the use of functional foods or drugs containing OA is, undoubtedly, an interesting path.
180 citations
Cites background from "Pentacyclic triterpene distribution..."
...More than 120 plant species have been described by their relevant OA contents (3), but few of them are socioeconomically important crops as is olive (Olea europaea L....
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TL;DR: A model in which ursolic acid reduces obesity, glucose intolerance and fatty liver disease by increasing skeletal muscle and brown fat is supported, and ursol acid is suggested as a potential therapeutic approach for obesity and obesity-related illness.
Abstract: Skeletal muscle Akt activity stimulates muscle growth and imparts resistance to obesity, glucose intolerance and fatty liver disease. We recently found that ursolic acid increases skeletal muscle Akt activity and stimulates muscle growth in non-obese mice. Here, we tested the hypothesis that ursolic acid might increase skeletal muscle Akt activity in a mouse model of diet-induced obesity. We studied mice that consumed a high fat diet lacking or containing ursolic acid. In skeletal muscle, ursolic acid increased Akt activity, as well as downstream mRNAs that promote glucose utilization (hexokinase-II), blood vessel recruitment (Vegfa) and autocrine/paracrine IGF-I signaling (Igf1). As a result, ursolic acid increased skeletal muscle mass, fast and slow muscle fiber size, grip strength and exercise capacity. Interestingly, ursolic acid also increased brown fat, a tissue that shares developmental origins with skeletal muscle. Consistent with increased skeletal muscle and brown fat, ursolic acid increased energy expenditure, leading to reduced obesity, improved glucose tolerance and decreased hepatic steatosis. These data support a model in which ursolic acid reduces obesity, glucose intolerance and fatty liver disease by increasing skeletal muscle and brown fat, and suggest ursolic acid as a potential therapeutic approach for obesity and obesity-related illness.
179 citations
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TL;DR: Evidence is presented that numerous agents identified from fruits and vegetables can interfere with several cell-signaling pathways and the active principle identified in fruit and vegetables and the molecular targets modulated may be the basis for how these dietary agents not only prevent but also treat cancer and other diseases.
1,653 citations
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...20 [42]...
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TL;DR: Oleanolic acid and ursolic acid are ubiquitous triterpenoids in plant kingdom, medicinal herbs, and are integral part of the human diet.
642 citations
"Pentacyclic triterpene distribution..." refers background in this paper
...The pharmacological relevance of these triterpenes has increased during the last two decades demonstrating multi-target properties such as wound healing, anti-inflammatory, anti-bacterial, antiviral, hepatoprotective and anti-tumoral effects, combined with low toxicity [9-13]....
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TL;DR: A new mechanism of action has been confirmed for some of the most promising anti-HIV derivatives, which makes them potentially useful additives to the current anti- HIV therapy.
585 citations
"Pentacyclic triterpene distribution..." refers background in this paper
...The pharmacological relevance of these triterpenes has increased during the last two decades demonstrating multi-target properties such as wound healing, anti-inflammatory, anti-bacterial, antiviral, hepatoprotective and anti-tumoral effects, combined with low toxicity [9-13]....
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TL;DR: The chemical analysis and quality control of Ginkgo leaves, extracts, phytopharmaceuticals and some herbal supplements is comprehensively reviewed and the growing literature on pharmacokinetic and fingerprinting studies of Ginkinggo is briefly summarised.
469 citations
TL;DR: Data suggest that anthocyanins and ursolic acid purified from C. mas fruits have biological activities that improve certain metabolic parameters associated with diets high in saturated fats and obesity.
Abstract: Much attention has been focused on food that may be beneficial in preventing diet-induced body fat accumulation and possibly reduce the risk of diabetes and heart disease. Cornelian cherries (Cornus mas) are used in the preparation of beverages in Europe and also to treat diabetes-related disorders in Asia. In this study, the most abundant bioactive compounds in C. mas fruits, the anthocyanins and ursolic acid, were purified, and their ability to ameliorate obesity and insulin resistance in C57BL/6 mice fed a high-fat diet was evaluated. Mice were initially fed a high-fat diet for 4 weeks and then switched to a high-fat diet containing anthocyanins (1 g/kg of high-fat diet) and ursolic acid (500 mg/kg of high-fat diet) for an additional 8 weeks. The high-fat diet induced glucose intolerance, and this was prevented by anthocyanins and ursolic acid. The anthocyanin-treated mice showed a 24% decrease in weight gain. These mice also showed decreased lipid accumulation in the liver, including a significant decrease in liver triacylglycerol concentration. Anthocyanin and ursolic acid treated mice exhibited extremely elevated insulin levels. Both treatments, however, showed preserved islet architecture and insulin staining. Overall, these data suggest that anthocyanins and ursolic acid purified from C. mas fruits have biological activities that improve certain metabolic parameters associated with diets high in saturated fats and obesity.
363 citations
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