Determination of steroidal saponins in different organs of yam (Dioscorea pseudojaponica Yamamoto)

Yams (Dioscorea spp.) are perennial trailing rhizome plants. Steroidal saponins, furostanol and spirostanol glycosides are the marked functional compounds in yams. In this investigation, a C18 solid phase extraction method was developed for yam saponins purification. The contents of saponins in various organs of yam (Dioscorea pseudojaponica Yamamoto) were also determined. Results showed that the recoveries of yam saponins extracted by the developed method were about 99.48–100.08% when the saponins (each saponin weighed 0.20, 0.50 and 1.00 mg) passing through the C18 cartridge. The extractive method could efficiently reduce the interferences from impurities in yam saponin extracts prior to HPLC analysis. The recoveries of added saponins in different yam organs were 98.34–99.92% for tuber flesh, 95.98–98.89% for tuber cortex, 97.89–99.44% for rhizophor, 93.82–98.01% for leaf and 93.87–97.65% for vine, respectively. The yam tuber cortex had the highest amount of saponins (582.53 μg/g dw), which was higher than that existed in the tuber flesh (227.86 μg/g dw) about 2.55 times. The contents of saponins in the rhizophor, leaf and vine of yam were 29.39, 24.41 and 23.96 μg/g dw, respectively.     

Effects of different storage conditions on steroidal saponinsin yam (Dioscorea pseudojaponica Yamamoto) tubers

Effect of storage on steroidal saponins, furostanol and spirostanol glycosides, in yam (D. pseudojaponica Yamamoto) tubers was determined. Unpeeled and vacuum-sealed peeled tubers were stored at −18, 4, 17 and 25 °C from 5 to 80 days separately. Furostanol glycosides in unpeeled tubers could be converted by furostanol glycoside 26-O-β-glucosidase (F26G) to spirostanol glycosides after 4 °C storage for 35 days (chilling injury could be found), or 17 and 25 °C storage for 50 days. The conversion increased with storage times. Peeled tubers stored at 17 and 25 °C for 5 days could experience organoleptic injury, which would enlarge with increasing storage period. After 35 days of storage, large part of vacuum-sealed tubers transformed to juice with stench. In the early 20 days storage, saponins in these tubers were lost rapidly. F26G activity in decreasing order was 25 °C > 17 °C > 4 °C and could be inhibited under vacuum.     

Saponins in Ipomoeabatatas tubers: Isolation,characterization, quantification and antioxidant properties

Triterpene saponins are a class of plant natural products with a wide range of bioactivities, which makes them an interesting research subject. This work reports, for the first time, the isolation and characterization of saponins in Ipomoeabatatas tuber flour, their quantification and antioxidant properties. Their structures were characterized on the basis of UV, FAB–MS, ESI–MS, GC–MS, polarimetry and NMR data, as: oleanolic acid-3-O-[β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-28-O-β-d-glucopyranoside (sandrosaponin IX) (1) and oleanolic acid-3-O-[β-d-galactopyranosyl-(1→3)-β-d-glucuronopyranosyl]-28-O-β-d-glucopyranoside (2). A new quantitative HPLC–DAD method for saponin content determination in this tuber was developed and validated. Their total content was 200.01 mg/100 g dry weight (RSD = 7.2%; p < 0.001). The single saponin contents were: 161.20 mg/100 g dry weight (RSD = 0.58%; p < 0.001) for saponin 1 and 14.67 mg/100 g dry weight (RSD = 0.41%; p < 0.001) for saponin 2. The antioxidant activities, tested by DPPH and FRAP assay, of total phytochemical fraction and of single saponins were moderate in relation to commercial standards.     

Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka

A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A₁ (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A₁ and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Δ²⁵ terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Δ⁹⁽¹¹⁾ to Δ⁷ in the aglycone moiety contributes little to the bioactivity.     

The processing of Panax notoginseng and the transformation of its saponin components

Notoginseng, the root of Panax notoginseng (Burk.) F. H. Chen (Araliaceae), a famous traditional Chinese medicine, has been used in both raw and processed forms due to their different therapeutic functions. In this study, HPLC analyses on saponin composition of processed notoginseng were conducted, which revealed that, during the steaming process, the five main saponin constituents (ginsenosides Rg₁, Rb₁, Rd, and Re, and notoginsenoside R₁) in raw notoginseng decreased gradually and some other new saponins were formed. Among these, eight newly converted ginsenosides were identified as 20(S)-Rh₁, 20(R)-Rh₁, Rk₃, Rh₄, 20(S)-Rg₃, 20(R)-Rg₃, Rk₁ and Rg₅. Different processing methods, including steaming and baking, were studied, along with the correlative dynamic curves of the transformation of saponins. The results indicated that the moisture content and temperature were the determinant effecting factors in the preparing process, and water content was necessary and high temperature was helpful for saponin transformation.     

Antioxidant activity of phenolics–saponins rich fraction prepared from defatted kenaf seed meal

The current study is aimed to determine the antioxidant properties of crude ethanolic extract (CEE) of defatted kenaf seed meal (DKSM) and its derived n-butanol (BF) and aqueous (AqF) fractions. Spectrophotometric assays showed that BF contained the highest amount of phenolic compounds and saponins, followed by CEE and AqF (p < 0.05). Similarly, HPLC-DAD analysis revealed that level of all the detected predominant phenolic compounds was significantly higher in BF (p < 0.05). Through multiple antioxidant assays, BF exhibited higher antioxidant activity than CEE and AqF, except for iron chelating activity (p < 0.05). Antioxidant activity of CEE and fractions were strongly correlated to their phenolic and saponin contents. This study showed that phenolic compounds and saponins could be extracted and partially purified simultaneously from DKSM by employing a simple alcoholic extraction–fractionation procedure. High antioxidative phenolics–saponins rich fraction from DKSM is a potential active ingredient that could be applied in nutraceuticals, functional foods as well as natural food preservatives.     

Antioxidant activity of stilbene glycoside from Polygonum multiflorum Thunb in vivo

Stilbene glycosides were isolated from the ethanol extract of the roots of Polygonum multiflorum Thunb. Two samples were obtained; a fraction separated by macroporous resin and pure crystals of 2,3,5,4′-tetrahydroxystilbene 2-O-β-glucopyranoside. The antioxidant activities of these two samples were evaluated using antioxidant tests of rats in vivo. The activities of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) of the serum and the organs (liver, heart and brain of rats) of d-galactose induced senile rats which were fed with stilbene glycoside, were increased; however, the content of 2-thiobarbituric acid-reactive substances (TBARS) was decreased. It is concluded that the stilbene glycoside from Polygonum multiflorum Thunb possesses high in vivo antioxidant activity.     

Antioxidant activity of a new phenolic glycoside from Lagenaria siceraria Stand. fruits

The antioxidant properties of different extracts of Lagenaria siceraria (bottle gourd) fruit were evaluated. In the process, a new phenolic glycoside (E)-4-hydroxymethyl-phenyl-6-O-caffeoyl-β-d-glucopyranoside (1) was isolated and identified together with 1-(2-hydroxy-4-hydroxymethyl)-phenyl-6-O-caffeoyl-β-d-gluco-pyranoside (2), protocatechuic acid (3), gallic acid (4), caffeic acid (5) and 3,4-dimethoxy cinnamic acid (6). Their structures were elucidated by extensive NMR experiments including ¹H-¹H (COSY) and ¹H-¹³C (HMQC and HMBC) spectroscopy and chemical evidences. The antioxidant potential of the compound 1 and 2 was tested in different in vitro assay systems such as free radical scavenging assay, 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction assay, superoxide scavenging activity, reducing power assay and linoleic acid peroxidation assay.     

Hepatoprotective and antioxidant activity of ethanolic extracts of edible lotus (Nelumbo nucifera Gaertn.) leaves

Lotus (Nelumbo nucifera Gaertn.), an aquatic vegetable, is extensively cultivated in eastern Asia, particularly in China. An ethanolic extract of the leaves was studied for its hepatoprotective activity against CCl₄-induced liver toxicity in rats. In vitro and in vivo antioxidant activity was also assessed. The results showed the hepatoprotective activity of lotus leaf extract (LLE) at doses of 300 and 500 mg/kg and in vivo antioxidant activity at 100 mg/kg that was comparable with that of a standard treatment comprising 100 mg/kg of silymarin, a known hepatoprotective drug. These data were supplemented with histopathological studies of rat liver sections. The main flavonoids and phenolic compounds of LLE were analysed by HPLC-DAD-ESI/MS methods. Six of the compounds detected were tentatively characterised, one as catechin glycoside and five as flavonoid glycoside derivatives: miricitrin-3-O-glucoside, hyperin, isoquercitrin, quercetin-3-O-rhamnoside and astragalin.     

Variation in saponin content during the growing season of spotted medic [Medicago arabica (L.) Huds.]

BACKGROUND: Spotted medic [Medicago arabica (L.) Huds.] is a minor forage species containing saponins which are reported to be biologically active. This study assessed the concentration and composition pattern of spotted medic saponins during the growing season and at senescence. The pattern of saponins was based on identification and quantification of their constituent sapogenins. At senescence, individual saponin concentrations of aerial and subterranean plant organs were also determined. RESULTS: Leaf total saponin content did not vary during the growing season and decreased remarkably at senescence. Seven sapogenins were identified and quantified during the season, bayogenin and hederagenin being the most abundant ones throughout. Total saponin content varied among plant organs at senescence, with the highest concentration in roots. A variable number of saponins from one (in seeds) to 19 (in leaves) were quantified. A clear relationship between leaf concentrations of sapogenins and those of their derivative saponins was revealed by correlation analysis. CONCLUSION: The species displayed a sapogenins/saponins pattern markedly different from those of other perennial or annual Medicago species. Saponins of queretaroic acid and 2β‐hydroxy queretaroic acid had no precedent in the Leguminosae. The high concentration of biologically active hederagenin suggested further assessment of possible effects on feeding animals. Copyright © 2010 Society of Chemical Industry     

Determination of chemical variability of phenolic and monoterpene glycosides in the seeds of Paeonia species using HPLC and profiling analysis

A rapid, sensitive, and accurate HPLC-DAD method was developed and validated for simultaneous determination of one phenolic glycoside and seven monoterpene glycosides, including 1-O-β-d-(4-hydroxybenzoyl)glucose (1), pyridylpaeoniflorin (2), (8R)-piperitone-4-en-9-O-β-d-glucopyranoside (3), oxypaeoniflorin (4), 6′-O-β-glucopyranosylalbiflorin (5), albiflorin (6), β-gentiobiosylpaeoniflorin (7), and paeoniflorin (8), in 44 batches of peony seeds from nine Paeonia species collected from different areas. Using the optimised method, separations were conducted with a YMC-pack ODS-A column with water/formic acid and methanol as the mobile phase. All eight analytes demonstrated good linearity (r² > 0.9993). The recoveries, measured at three concentration levels, varied from 98.20% to 103.81%. Six compounds including 1 and 4–8 occur ubiquitously in all the seeds of nine Paeonia species, and compounds 2 and 3 showed undetectable levels or very low content in several samples. The seed samples were classified into several groups, which coincide with the taxonomy of Paeonia at the section level. Peony seed might be a useful resource in developing new herbal or food products.     

Two flavanone compounds from litchi (Litchi chinensis Sonn.) seeds,one previously unreported,and appraisal of their α-glucosidase inhibitory activities

Using a bioactivity-guided method, a new and a previously reported flavanone glycoside were isolated from 50% ethanol extract of litchi (Litchi chinensis Sonn.) seeds. Column chromatography using macroporous resin, silica gel and Sephadex LH-20 was applied during the isolation, and the method of PMP derivatisation was performed to investigate the component sugar of the compounds. The structures of the compounds were elucidated by ¹H, ¹³C, and 2D NMR (HMQC, HMBC) spectroscopy and HR-ESIMS. Compound 1 was identified as (2R)-naringenin-7-O-(3-O-α-l-rhamnopyranosyl-β-d-glucopyranoside), a new, natural product that had been synthesised previously. Compound 2 was (2S)-pinocembrin-7-O-(6-O-α-l-rhamnopyranosyl-β-d-glucopyranoside). The two isolated compounds showed activity in the α-glucosidase inhibition assay.     

Flavonoid glycosides in the shoot system of Okinawa Taumu (Colocasia esculenta S.)

Six C-glycosylflavonoids and one O-glycosylflavonoid have been isolated from the shoot system of Taumu (Colocasia esculenta S.). They were identified as schaftoside, isoschaftoside, orientin, isovitexin, isoorientin, vitexin and luteolin 7-O-sophoroside. The presence of catechol moiety in the B-ring of isoorientin, orientin and luteolin 7-O-sophoroside showed strong antioxidant activity with different mechanisms of action in DPPH radical scavenging, β-carotene bleaching and superoxide radical inhibition assays. The amount of dry weight matter extract of water was higher than methanol for both the leaf and the stem parts. Isovitexin was the main compound in water and methanol extracts of the leaf while schaftoside was the main compound of the water extract of the stem. Methanol extract of the leaf showed higher DPPH radical scavenging activity than water extract while the opposite was observed for the stem. The results of this experiment suggest the potential of the leaf of Taumu as a source of dietary antioxidant.     

A new steroidal saponin from the seeds of Allium tuberosum

A steroidal saponin, named tuberoside A, together with six known compounds, were isolated from the seeds of Allium tuberosum Rottl. ex Spreng. On the basis of acid hydrolysis, comprehensive spectroscopic analyses and comparison with spectral data of known compounds, its structure was established as (24S, 25S)-5β-spirostan-2β,3β,24-triol 3-O-α-l-rhamnopyranoyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside. The six known compounds were thymidine, adenosine, 2-hydroxy purine, adenine, uracil, and thymine. 2-hydroxy purine, adenine, uracil and thymine are isolated from the seeds of A. tuberosum for the first time. This paper deals with the isolation and structural elucidation of the new saponin.     

Yield and nutritional content of Pleurotus sajor caju on wheat straw supplemented with raw and detoxified mahua cake

The effect of supplementation of wheat straw (WS) with raw/detoxified mahua cake (MC) on yield and nutritional quality of Pleurotus sajor caju was studied. Raw cake significantly enhanced the yield compared to control and could be tolerated up to a 10% addition. Detoxification further improved the mushroom yield giving a maximum of 1024.7 g kg⁻¹ from WS supplemented with 20% saponin free detoxified mahua cake. Chemical analysis of fruit bodies revealed that they are rich in proteins (27.4–34.8%), soluble sugars (28.6–32.2%) and minerals. Glucose, trehalose and glutamic acid, alanine were the major sugars and amino acids detected by HPLC analysis, respectively. HPLC studies further confirmed the absence of saponins (characteristic toxins present in MC) in both fruit bodies and spent. Degradation of complex molecules in spent was monitored via FTIR. The study proved beneficial for effective management of agricultural wastes along with production of nutrient rich and saponin free fruit bodies/spent.     

Phenylpropanoid glycosides from the seeds of Michelia hedyosperma

The seed of Michelia hedyosperma Law (Magnoliaceae) is a commonly used spice by the local people living in the south of Yunnan province, China. From which, six new phenylpropanoid glycosides, michehedyosides A–F (1–6) were obtained, in addition to six known compounds, eugenol, eugenol 4-O-β-d-glucopyranoside, martynoside, alaschanioside C, 3,4-methylenedioxycinnamyl alcohol, and (+)-pinoresinol 4-O-β-d-glucoside. Their structures were elucidated on the basis of detailed spectroscopic analyses and chemical methods.     

Evaluation of the total oxidant scavenging capacity of saponins isolated from Platycodon grandiflorum

The antioxidant activity of saponins isolated from Platycodon grandiflorum (PG; Balloon flower) was determined using the total oxidant-scavenging capacity (TOSC) assay. Platycodigenin, polygalacic acid, platycodin D, platycoside E and deapioplatycoside E were isolated and their structures were characterised based on their physical and spectral properties and by comparison of these results with similar data in the literature. Platycodin D showed the greatest TOSC value against peroxyl radicals, followed (in decreasing order) by polygalacic acid, platycodigenin, deapioplatycosides E and platycoside E. Although the TOSC value of the saponins against peroxyl radicals was less than that of glutathione (GSH) and Trolox used as positive controls. However, TOSC value of platycodigenin, deapioplatycoside E, platycodin D or platycoside E against peroxynitrite was 2.35-, 1.27-, 1.02- or 0.75-fold of GSH, respectively, while polygalacic acid exhibited no scavenging capacity of peroxynitrites. These results suggest importance of the presence of hydroxyl group at carbon 24 in platycodigenin in peroxynitrite scavenging. As the number of attached sugar residues in the saponin glycosides is increased, the scavenging capacity of peroxyl radical, but not peroxynitrite was significantly decreased. These results showed that PG saponins have potent antioxidant activities, which is different according to the structure of aglycones and the number of attached sugar residues.     

Pretreatment eliminates throat irritation by water yam and facilitates the development of functional cookies

Water yam (Dioscoreaalata) provides sufficient nutrients in terms of protein (10.075 ± 0.02%), fibre (3.40 ± 0.03%) and minerals (potassium and phosphorous). However, due to the presence of anti-nutritional factors such as saponins, water yam causes throat irritation. Consequently, it is less preferred among consumers, and thus, the commercial importance of yam tubers has been limited. The current investigation aims to reduce the saponin content of water yam by pretreatment of yam tubers at the optimised conditions (blanching with 0.2% potassium metabisulphite, 0.5% tartaric acid and 0.5% citric acid) that rendered a 50% reduction in the saponin content (1.65% to 0.86%). The said nutritious yam flour was utilised as a replacement of refined wheat flour (13%) in the development of functional cookies. The yam cookies showed higher mineral content (phosphorous: 116.20 ± 0.80 mg/100 g; potassium: 221.11 ± 0.98 mg/100 g). Reduced water activity and incorporation of antioxidants in yam cookies decreased the peroxide value of the same during storage attesting its higher shelf-life.     

Isolation of some active compounds from Origanum vulgare L. ssp. vulgare and determination of their genotoxic potentials

Origanum vulgare L. (oregano) is a flavoring herb widely used around the world. In the present study, crude extract of O. vulgare L. (oregano) and its petroleum ether, chloroform, ethyl acetate, n-butanol, water fractions were prepared in order to isolate and investigate antimutagenic compounds from the active extract through the bacterial genotoxicity assay guided fractionation procedures. The methanol extract and its n-butanol fraction showed significant antimutagenic activity. In the end of sub-fractionation process of the n-butanol extract, luteolin 7-O-glucuronide and luteolin 7-O-xyloside were isolated. These compounds showed significant antimutagenic activity against 9-Aminoacridine and N-Methyl-N′-nitro-N-nitrosoguanidine mutagenicity. The inhibition rates ranged from 22.1% (luteolin 7-O-xyloside: Salmonella typhimurium TA1537 – 0.4 mM/plate) to 67.8% (luteolin 7-O-glucuronide: S. typhimurium TA1537 – 0.8 μM/plate). In conclusion, the results revealed that luteolin 7-O-glucuronide and luteolin 7-O-xyloside are two of the antimutagenic compounds of O. vulgare L. ssp. vulgare.