Isothiocyanates and sterols from Raphanus sativus (original) (raw)
Related papers
Chemical Constituents of Raphanus sativus
Chemical investigation of the dichloromethane extract of the freeze-dried roots of Raphanus sativus afforded 3-(E)-(methylthio)methylene-2-pyrrolidinethione (1), a mixture of 4-methylthio-3-butenyl isothiocyanate (2) and 4-(methylthio)butyl isothiocyanate (3), β-sitosterol (4), β-sitosteryl-3β-glucopyranoside-6'-O-palmitate (5), monoacylglycerols (6), and a mixture of α-linolenic acid (7) and linoleic acid (8). The structures of 1-3 were elucidated by extensive 1D and 2D NMR spectroscopy, while those of 4-8 were identified by comparison of their NMR data with those reported in the literature.
Secondary Metabolites from Raphanus sativus
Research Journal of Pharmaceutical, Biological and Chemical Sciences, 2015
Chemical investigation of the dichloromethane extract of the freeze-dried roots of Raphanus sativus led to the isolation of β-sitosteryl-3β-glucopyranoside-6'-O-palmitate (1), α-(7Z,10Z,13Z)-hexadecatrienoic acidmonoglyceride (2), β-sitosterol (3), triacylglycerols (4), α-linolenic acid (5a), and linoleic acid (5b). The structures of 1-5b were identified by comparison of their NMR data with literature data.
Deciphering the Nutraceutical Potential of Raphanus sativus—A Comprehensive Overview
Nutrients, 2019
Raphanus sativus (Radish) belongs to the Brassicaceae family and is a widely consumed root vegetable all around the world. The nutritional and medicinal values of radishes have been proven by several researches. Extracts prepared from the aerial and underground parts of radishes have been used in the treatment of stomach disorders, urinary infections, hepatic inflammation, cardiac disorders and ulcers in folk medicine since the ancient times. The pharmaceutical potential of radishes is attributed to the presence of its beneficial secondary metabolites, such as glucosinolates, polyphenols and isothiocyanates. The present review has focused on the impact of radish extract administration under pathological complications, such as cancer, diabetes, hepatic inflammation and oxidative stress. In addition, a comprehensive view of molecular mechanism behind the regulation of molecular drug targets associated with different types of cancers and diabetes by the bioactive compounds present in t...
Journal of Agricultural and Food Chemistry, 2008
There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p < 0.05) increased Bax and decreased Bcl2 protein expression, as well as producing caspase-9 and PARP-1 cleavage after 3 days of exposure in the three cancer cell lines. GRH-ITC treatment was shown to have no toxicity with regard to normal human lymphocytes (-15 ( 5%) in comparison with SFN (complete growth inhibition). GRH and GRH-ITC were able to quench the 2,2-diphenyl-1-picrylhydrazyl radical, with second-order rate constants of 14.0 ( 2.8 and 43.1 ( 9.5 M -1 s -1 , respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant R-tocopherol was 425 ( 40 M -1 s -1 . GRH reacted with H 2 O 2 and tert-butyl hydroperoxide in water (pH 7.4) at 37°C, with rate constants of 1.9 ( 0.3 × 10 -2 and 9.5 ( 0.3 × 10 -4 M -1 s -1 (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cytotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.
IN VITRO PHARMACOLOGICAL STUDY OF EXTRACT OF RAPHANUS SATIVUS SPROUTS
Ethyl acetate extract of Raphanus sativus sprouts belonging to Brassicaceae, produced by cold maceration reveal the presence of volatile oils. Dilutions of the extract 20, 40, 60, 80, 100 µg/ml prepared in DMSO were used for the in vitro study. The antimicrobial activity of the extract was assessed using Bacillus subtilis (NCIM 2698), Staphylococcus aureus (NCIM 2079), Escherichia coli (NCIM 2344), Klebsiella pneumonia (NCIM 2957) and Aspergillus flavus (NCIM 568) against the standards gentamycin and ketoconazole. In vitro pharmacological studies, include the reducing activity, antioxidant activity and anti inflammatory activity were evaluated using the ferric reducing assay, hydrogen peroxide scavenging assay and albumin denaturation method respectively. The extract had shown significant antibacterial activity on all organisms excluding Klebsiella and Escherichia than the standard. In vitro studies reveal significant reducing (36.015 + 0.686), antioxidant (26.830 + 0.240) and anti inflammatory activities (25.865 + 0.191) against the standard butylated hydroxyl toluene (BHT) (31.879 + 2.629), ascorbic acid (21.7245 + 0.240) and Diclofenac (0.4825 + 0.025) respectively.
Bioactive Compounds and Chemical Profile of Raphanus sativus
International Journal of Engineering and Techniques, 2024
At higher concentrations (100 mg/mL), the oil demonstrated limited inhibition compared to standard antibiotics and antifungal agents. While the oil exhibited some antimicrobial properties, particularly against gram-positive bacteria and fungi. it was not as potent as conventional antibiotics. These findings suggest Raphanus sativus oil may have limited but potential use in antimicrobial applications.
Foodborne Pathogens and Disease, 2009
Acetone and hexane extracts derived from the root, stem, and leaf of Raphanus sativus were investigated for their antibacterial activity against foodborne and resistant pathogens, such as Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Salmonella typhimurium, Enterobacter aerogenes, Enterobacter cloacae, and Escherichia coli. Total and individual isothiocyanate (ITC) components and their relationship with the antibacterial activity of R. sativus were also evaluated. Both acetone and hexane fractions of root, stem, and leaf exhibited selective antibacterial activity against the organisms tested. Antibacterial activity was strongest in the acetone fraction of root with larger zone of inhibition and lower minimum inhibitory concentration. The results obtained were comparable to that seen with standard antibiotics. Of the different parts of R. sativus studied, root tended to be more active than the stem and leaf extracts in inhibiting the bacterial growth. Gas chromatographic analysis revealed the presence of variable amounts of five different ITCs such as allyl isothiocyanate (AITC), phenyl isothiocyanate (PITC), benzyl isothiocyanate (BITC), phenethyl isothiocyanate, and 4-(methylthio)-3-butenyl isothiocyanate (MTBITC) in different parts of the plant. The low linear correlation between the total ITC content and antibacterial activity implied that bacterial growth inhibitory ability of R. sativus was not dependent on the total ITC content. However, the antibacterial activity of R. sativus was well correlated with AITC, PITC, and BITC for all organisms except for Enteroc. faecalis, whose inhibitory effect was more related to MTBITC.
Bioscience Journal, 2020
The radish (Raphanus sativus L.) is a vegetable of the Brassicaceae family cultivated worldwide and has several medicinal properties. Its biological activities are related to various secondary metabolites present in the species, especially phenolics. Thus, the objectives of this study were the chemical analysis and evaluation of the antioxidant and antimicrobial activities of the dry extract and fractions of the fodder turnip leaves (R. sativus var. oleiferus Metzg.). Samples were analyzed by mass spectrometry and the antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical method and the reducing power method. Antimicrobial activity was determined by the agar diffusion and microdilution methods. The total phenols were concentrated in the butanol fraction (121.27 mg GAE/g) and the flavonoids were concentrated in the ethyl acetate fraction (98.02 mg EQ/g). The ethyl acetate fraction showed the best antioxidants results, with 83.45% of free radical sca...
European Journal of Medicinal Plants
Raphionacme vignei E. A. Bruce (Apocynaceae) is a plant of the traditional African pharmacopoeia, whose parts are used in the treatment of various pathologies. Water-soaked R. vignei tubers are edible. The objective of this study was to isolate triterpenoids from the acetonic extract of R. vignei tubers, evaluate the analgesic and anti-inflammatory activities of each molecule. The isolated compounds, characterized by NMR and mass spectrometry, is composed of six triterpenoids: beta-amyrin dodecanoate 1(DDQ1), lupeol dodecanoate 2(DDQ2), beta-amyrin acetate 3(DDQ3), lupeol acetate 4(DDQ4), luepol 5(DDQ5) and β-sitosterol 6(DDQ6). These molecules (DDQ2, DDQ3, DDQ4, DDQ5, DDQ6) are anti-inflammatory in carrageenan induced rat paw edema, with better anti-inflammatory power for DDQ2 and DDQ4, which would be related to the presence of acetate function and cycle E. DDQ2 and DDQ4 are also analgesic in acetic acid induced contortions and the removal...
Food Chemistry, 2012
The freeze-dried sprouts' juice of Raphanus sativus (L.) cv. Sango was prepared and analysed for the first time. HPLC analysis of total isothiocyanates, after protein displacement, resulted in 77.8 ± 3.0 lmol/g of dry juice while GC-MS analysis of hexane and acetone extracts showed E-and Z-raphasatin (8.9 and 0.11 lmol/g, respectively) and sulforaphene (11.7 lmol/g), summing up to 20.7 ± 1.7 lmol/g of free isothiocyanates. Sprouts' juice contained an unprecedented wealth of anthocyanins and a new fractionation methodology allowed us to isolate 34 mg/g of acylated anthocyanins (28.3 ± 1.9 lmol/g), belonging selectively to the cyanidin family. Analysis was performed by HPLC-PDA-ESI-MS n and extended to deacylated anthocyanins and aglycones, obtained, respectively, by alkaline and acid hydrolysis. This study identified 70 anthocyanins, 19 of which have never been described before and 32 of which are reported here in R. sativus for the first time. Sango radish sprouts are exceptional dietary sources of heath-promoting micronutrients.