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Acid Hydrolysis of Saponin-Rich Extracts of Quinoa, Lentil, Fenugreek and Soybean to Yield

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Acid Hydrolysis of Saponin-Rich Extracts of Quinoa, Lentil, Fenugreek and Soybean to Yield 1 2 Acid hydrolysis of saponin-rich extracts of quinoa, lentil, fenugreek and soybean to yield 3 sapogenin-rich extracts and other bioactive compounds 4 5 Teresa Herrera1,2, Joaquín Navarro del Hierro1,2, Tiziana Fornari1,2, Guillermo Reglero1,2,3, 6 Diana Martin1,2* 7 8 1Departamento de Producción y Caracterización de Nuevos Alimentos. Instituto de 9 Investigación en Ciencias de la Alimentación (CIAL) (CSIC–UAM), Madrid, España 10 2Sección Departamental de Ciencias de la Alimentación, Facultad de Ciencias, UAM, Madrid, 11 España 12 3Imdea-Alimentación. CEI UAM+CSIC, Madrid, España 13 14 * Corresponding author: [email protected], Tel.: 0034 91 001 7930 15 16 Abstract 17 BACKGROUND: Typical hydrolysis times of saponins without considering the effect of time 18 on the degradation of the targeted compounds, namely sapogenins, are generally assumed. 19 When producing natural extracts, it should be considered that the performance of hydrolysis to 20 yield a target compound might also affect the final composition of the extracts in terms of other 21 bioactive compounds. In our study, saponin-rich extracts from fenugreek, quinoa, lentil and 22 soybean were produced and their acid hydrolysis to produce sapogenin-rich extracts was 23 performed at different times (0-6 h). Disappearance of saponins and appearance of sapogenins 24 were analyzed by HPLC-DAD-MS and GC-MS, respectively. The impact of hydrolysis on 25 phytosterols and tocopherol of the extracts was also evaluated. 26 RESULTS: Fenugreek showed the highest content of saponins (169 g kg-1), followed by lentil 27 (20 g kg-1 ), quinoa (15 g kg-1) and soybean (13 g kg-1). Hydrolysis during 1 h caused complete 28 disappearance of saponins and the highest release of sapogenins. Hydrolyzed fenugreek and 29 quinoa extracts contained the highest amounts of sapogenins and minor fractions of 30 phytosterols and tocopherol. Hydrolyzed extracts of lentil and soybean contained a major 31 fraction of phytosterols and a low fraction of sapogenins. In all cases, sapogenins decreased 32 after 1 h of hydrolysis, phytosterols slightly decreased, and tocopherol was unaffected. 33 Standards of diosgenin and oleanolic acid also showed this decreasing pattern under acid 34 hydrolysis conditions. 35 CONCLUSION: Hydrolysis times of 1 h for saponin-rich extracts from the assayed seeds 36 guarantee extracts with the maximum transformation to sapogenin-rich extracts, along with 37 phytosterols and tocopherol, being fenugreek and quinoa seeds preferred. 38 39 KEYWORDS 40 saponins, sapogenins, phytosterols, tocopherol, acid hydrolysis, legumes 41 42 INTRODUCTION 43 Edible seeds are relevant sources of minor phytochemicals of interest, such as saponins, 44 polyphenols, phytosterols, carotenoids, alkaloids or tocopherols, due to the bioactive properties 45 described for such components. Within these compounds, saponins are widely found at relative 46 high levels in many edible seeds.1,2 Saponins consist of a hydrophobic aglycone backbone 47 (sapogenin) linked to hydrophilic sugar chain/s. Depending on differences in the sapogenin 48 structure or number of sugars linked, saponins can be diversely classified. According to the 49 chemical structure of the sapogenin skeleton, saponins can be classified into steroidal or 50 triterpenoid saponins. In addition, they can be divided attending the number of sugar chains as 51 monodesmosidic, bidesmosidic, or tridesmosidic.3 Triterpenoid saponins are commonly 52 reported in seeds of legumes (alfalfa, soybean, chickpea, mung bean, kidney bean and lentil), 53 quinoa, sunflower, or horse chestnut, as well as in other sources, such as ginseng roots, liquorice 54 roots, spinach leaves, tea leaves, quillaja bark, sugar beet or alliums species. In the case of 55 steroidal saponins, they are frequently found in seeds of fenugreek, tomato, or oats, as well as 56 in other sources, such as yucca, yam, ginseng roots, asparagus, aubergine or capsicum 57 peppers.3,4 58 Saponins, traditionally considered as antinutrients, have been under intense research over the 59 last years due to their evidenced biological activities, such as immunostimulatory, 60 hypocholesterolemic, antitumor, anti-inflammatory, antibacterial, antiviral, antifungal, or 61 antiparasitic activities.5–7 As recent examples, the anti-inflammatory activity of triterpenoid 62 saponins from soybean have been shown in macrophages by downregulation on nitric oxide 63 production.8 Similarly, triterpenoid quinoa saponins have demonstrated to inhibit the release of 64 inflammatory cytokines, as well as decrease the production of inflammatory mediators.9 Quinoa 65 saponins have also shown to inhibit triglyceride accumulation in adipocytes and suppress 66 adipogenesis.10 On the other hand, it was recently described that triterpenoid saponin extracts 67 from lentil caused both hypocholesterolemic and prebiotic effect in rats.11 Concerning steroid 68 saponins, fenugreek extracts have shown to improve the serum lipid, bile acid efflux, anti- 69 peroxide activities and lipid area of liver tissue in rats, consequently ameliorating dyslipidaemia 70 by accelerating cholesterol metabolism, inhibiting cholesterol synthesis, and facilitating reverse 71 cholesterol transport.12 Fenugreek saponins are also known for their pro-apoptotic and 72 anticancer properties.13 73 Unfortunately, saponins are poorly absorbed during the digestion process and exhibit low 74 bioavailability due to diverse limiting factors such as low membrane permeability, chemical 75 transformations, or colonic fermentation.14 On the contrary, most sapogenins have 76 demonstrated superior bioavailability, and some bioactivities of sapogenins are even higher 77 than their former saponins, due to more favorable chemical properties caused by the lack of the 78 sugar chain.14–18 As examples, Choi, Jung, Lee & Park19 demonstrated that hederagenin and 79 oleanolic acid, obtained from the hydrolysis of the saponin rich fraction of the plant Akebia 80 quinata, exhibited a stronger anti-edema and analgesic effect than their former 81 kalopanaxsaponin A. Furthermore, some sapogenins can even display a certain biological effect 82 that was not shown by their former saponins. For instance, Gurfinkel & Rao20 found that the 83 aglycones soyasapogenol A and B showed almost complete suppression of cell growth, while 84 soyasaponin A1, A2, and I, had no effect on cell growth. Similarly, Uemura et al.21 also found 85 that a hydrolized fenugreek extract significantly inhibited triglyceride accumulation in HepG2 86 cells, while the saponin fraction had no effect. Therefore, a way to increase some specific 87 bioactivities of saponins or even reveal novel bioactivities might be achieved by their previous 88 transformation to sapogenins. 89 Hydrolysis of saponins is the known procedure for the conversion of saponins to sapogenins. 90 In this sense, saponins can be hydrolyzed by chemical (by acid or alkali), enzymatic and 91 microbial methods, leading to the formation of sapogenins, prosapogenins, sugar residues or 92 monosaccharides depending on the hydrolysis method and conditions performed.22 In general, 93 it seems that enzymatic methods are less effective than chemical hydrolysis, making the acid 94 hydrolysis of saponins the preferred procedure, which has been more extensively used and 95 explored.23 96 On the one hand, it is important to consider that during chemical hydrolysis of saponins, specific 97 conditions such as temperature, time of reaction, and type of hydrolysing agent could affect the 98 stability of saponins, the yield on final products, and the generation of artifacts.24,25 Specifically, 99 prolonged heating with an organic acid can cause artifact formation, low yields and low 100 selectivity.26,27 Additionally, the abundance and diversity of the final products can change 101 significantly depending on the structural complexity of saponins or sapogenins, the nature of 102 the attached side chains, and the attachment positions of sugar moieties to the aglycone, 103 resulting in a wide variety of these compounds.3 Despite these circumstances, it is frequently 104 found that the hydrolysis of saponins is performed under common and general conditions, 105 without previous detailed evaluation of the ideal conditions of hydrolysis for the specific 106 saponins of interest in order to obtain sapogenin-rich extracts. As example, typical hydrolysis 107 conditions have been summarized in Table 1. In general, 2-3 h of reaction time, temperatures 108 around 100 ºC, and 2 M HCl solutions are the most frequently used conditions. Longer times 109 of hydrolysis up to 4, 8 or 72 h have also been found. It should be considered that excessive 110 times of hydrolysis might lead to a potential degradation of sapogenins, together with 111 unnecessary energy consumptions.26,27 Therefore, considering the abovementioned hydrolysis 112 parameters, at least the effect of time during the hydrolysis of saponins to produce sapogenins 113 should be considered. 114 On the other hand, it is important to remark that within the research field of the production of 115 natural extracts, such as saponin-rich extracts, it should be considered that the performance of 116 hydrolysis to yield a target compound might also affect the final composition of the extracts in 117 terms of other bioactive compounds of interest. This is because natural extracts are complex 118 mixtures of a wide diversity of phytochemicals, and the subsequent bioactive properties of the 119 extracts are due to the combination
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