Antiproliferative, Proapoptotic, Antioxidant and Antimicrobial Effects of Sinapis nigra L. and Sinapis alba L. Extracts

Abstract

High Brassicaceae consumption reduces the risk of developing several cancer types, probably due to high levels of glucosinolates. Extracts from Sinapis nigra L. (S. nigra) and Sinapis alba L. (S. alba) have been obtained from leaves and seeds under different conditions using ethanol/water mixtures because their glucosinolates are well accepted by the food industry. The EtOH/H2O 8:2 mixture gives better yields in glucosinolate amounts from ground seeds, mainly, sinalbin in S. alba and sinigrin in S. nigra. The highest antiproliferative activity in both non-tumor and tumor cell lines was induced by S. alba seeds extract. To evaluate whether the effect of Sinapis species (spp) was only due to glucosinolate content or whether it was influenced by the extracts’ complexity, cells were treated with extracts or glucosinolates, in the presence of myrosinase. Pure sinigrin did not modify cell proliferation, while pure sinalbin was less effective than the extract. The addition of myrosinase increased the antiproliferative effects of the S. nigra extract and sinigrin. Antiproliferative activity was correlated to Mitogen-Activated Protein Kinases modulation, which was cell and extract-dependent. Cell-cycle analysis evidenced a proapoptotic effect of S. alba on both tumor cell lines and of S. nigra only on HCT 116. Both extracts showed good antimicrobial activity in disc diffusion tests and on ready-to-eat fresh salad. These results underline the potential effects of Sinapis spp in chemoprevention and food preservation.

Human, Animal and Plant Health Benefits of Glucosinolates and Strategies for Enhanced Bioactivity: A Systematic Review

“…Seed extracts that portrayed such benefits as chemopreventive, cytotoxic and antimicrobial include: - seed extracts of Brassica juncea L. containing 3- butenyl ITCs [ 35 ], Lobularia libyca [ 36 ], Carica papaya L. rich in benzyl GS [ 37 ], mustard seed powder [ 38 ], Sinapsis alba L. and Sinapsis nigra L. with high content of sinalbin and sinigrin, respectively [ 39 ]. GMG isolated from Moringa oleifera L. seeds possessed chemopreventive [ 40 , 41 , 42 ], insect larvae deterrence [ 43 ], antibacterial [ 44 ] and anti-inflammatory activity [ 45 ].…”

“…The antimicrobial activity of plant extracts possessing therapeutic potential relies on the presence of volatiles, among which GSs and GSHP compounds have been well identified. Studies focusing on these compounds and their antimicrobial activities show that active compounds affect pathogens’ membrane integrity [ 127 ], intracellular potassium release [ 10 ], inhibit growth in pathogens [ 22 , 36 , 39 , 51 , 52 , 53 , 54 , 79 , 80 , 83 , 87 , 89 , 90 ], kill pathogens [ 81 , 82 , 88 ] and change physiochemical surface properties and charges. Inhibitory effects of GSs and GSHPs can be non-selective [ 59 ] or may vary between different pathogens, as illustrated by allyl and phenylpentyl ITCs in A. rusticana which has higher antifungal activity than antibacterial activity [ 80 ].…”

“…Compounds like butenyl thiocyanates, allyl, phenethyl ITCs [ 100 ], and GMG GSs [ 133 ] reveal such effects. The compounds’ effectivity lies in their ability to inhibit cell proliferation, [ 37 , 39 , 61 ] arrest the cell cycle [ 38 ], causing morphological changes, cytotoxicity, and cell apoptosis [ 35 , 36 , 40 , 41 , 54 , 56 , 59 , 69 , 101 , 113 , 115 , 119 ]. These activities may be dose dependent [ 37 ] and may also be defined by the chemical nature of the compound [ 143 ].…”

Natural Antioxidants from Seeds and Their Application in Meat Products

“…From the cruciferous group, mustard (Sinapis alba) seeds are interesting sources of polyphenols. Mustard seeds are largely used as a condiment in food preparations [58]. A recent study indicated that the phenolic profile of mustard seeds hulls comprises sinapic acid and its derivatives sinapine and sinapoyl glucose [52].…”

Synthesis of sinapine and its unprecedented ruthenium-catalyzed [2+2] photodimerization

“…Recently, we became interested in sinapine (1 as its thiocyanate, Scheme 1) [36][37] , an alkaloid which can be found in white mustard (Sinapis alba) [38][39] and canola (Brassica sp.) [40][41] because some interesting biological activities have been reported for this hybrid composed from (E) 4-hydroxy-3,5dimethoxycinnamic acid and choline.…”