Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential
Abstract
:1. Introduction
2. Results and Discussion
2.1. Glucosinolates and Volatile Constituents
2.2. Antioxidative and Anticholinesterase Activity
2.3. Cytotoxic Activity
3. Material and Methods
3.1. Plant Material
3.2. Reagents
3.3. Isolation and Chemical Analysis
3.3.1. Isolation
3.3.2. HPLC-PDA-MS/MS Analysis and Quantification of Desulfoglucosinolates
3.3.3. Isolation and GC-MS Analysis of Volatiles
3.3.4. Methods of Identification
3.4. Biological Activities Assays
3.4.1. Antioxidant Activity
3.4.2. Acetylcholinesterase/Butyrylcholinesterase Inhibitory Activity
3.4.3. Cell Proliferation Assay (MTT)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Glucosinolate | tR (minutes) | Flower | Leaf and Stem | Root |
---|---|---|---|---|
Glucoraphanin (5) | 8.1 | 0.3 ± 0.0 | 0.1 ± 0.0 | 0.1 ± 0.0 |
Glucoraphenin (3) | 8.4 | 5.7 ± 0.8 | 1.0 ± 0.2 | 1.6 ± 0.4 |
Glucosinalbin (7) | 11.3 | 6.8 ± 0.5 | 5.6 ± 0.9 | 8.3 ± 1.0 |
Gluconapin (1) | 12.1 | 0.6 ± 0.1 | 0.2 ± 0.0 | 0.5 ± 0.1 |
Glucotropaeolin (6) | 18.2 | 0.2 ± 0.0 | 0.1 ± 0.0 | 0.2 ± 0.0 |
Glucoerucin (4) | 18.9 | - | - | tr |
Glucoraphasatin (2) | 19.5 | 1.0 ± 0.2 | - | 2.2 ± 0.2 |
Total (μmol/g dry weight) | 14.6 ± 1.6 | 7.0 ± 1.1 | 12.9 ± 1.7 |
Hydrodistilate | Extract | |||||
---|---|---|---|---|---|---|
Glucosinolate | Identified Breakdown Compound | RI | Flower | Leaf and Stem | Root | Whole Plant Material |
Gluconapin (1) | But-3-enyl ITC a,b,c | 993 | 0.8 | 2.0 | 10.3 | - |
Glucotropaeolin (6) | 2-Phenylacetonitrile a,b | 1178 | 1.0 | tr | - | - |
Benzyl ITC a,b | 1394 | - | - | tr | - | |
Glucoraphasatin (2) | 5-(Methylsulfanyl)pent-4-enenitrile *,a,b | 1214 | 14.5 | - | 1.4 | - |
5-(Methylsulfanyl)pent-4-enenitrile *,a,b | 1251 | 4.7 | - | 1.0 | - | |
4-(Methylsulfanyl)but-3-enyl ITC a,b,c | 1440 | 0.1 | - | 2.4 | - | |
Glucoerucin (4) | 4-(Methylsulfanyl)pentanenitrile a,b,c | 1233 | 2.3 | - | - | - |
4-(Methylsulfanyl)butyl ITC (erucin) a,c | 1457 | - | - | 1.1 | - | |
Glucoraphenin (3) | 4-(Methylsulfinyl)but-3-enyl ITC a,c | 1817 | - | - | - | 88.3 |
Other Volatiles | ||||||
1,2-Dimethylbenzene b | 874 | 3.9 | 0.8 | 4.0 | - | |
3-Methylsulfanylpropanal b | 919 | - | - | 0.3 | - | |
Dimethyltrisulfide a,b | 981 | tr | - | 9.4 | - | |
Benzeneacetaldehyde a,b | 1063 | 0.5 | 1.1 | 1.3 | - | |
(E)-Non-2-en-1-ol a,b | 1113 | 1.3 | 0.8 | 0.5 | - | |
Dimethyltetrasulfide a,b | 1235 | - | - | 0.3 | - | |
4-Vinyl-2-methoxyphenol a,b | 1353 | 0.7 | 0.8 | tr | - | |
(E)-β-Ionone a,b | 1492 | 1.8 | - | - | - | |
Tetradecanoic acid a,b | 1828 | 3.9 | 18.3 | 6.7 | - | |
6,10,14-Trimethylpentadecan-2-one a,b | 1854 | 28.2 | 25.5 | 1.9 | - | |
Hexadecanoic acid a,b | 2016 | 24.6 | 39.8 | 53.5 | 6.1 | |
Total sum (%) | 88.3 | 89.1 | 94.1 | 94.4 |
Flower Hydro-Distillate (FH) | Root Hydro-Distillate (RH) | |
---|---|---|
Antioxidant Activity | ||
DPPH (Inhibition %) | 9.6 ± 0.4 | 10.2 ± 1.4 |
FRAP (µM Fe2+) | 41.7 ± 0.9 | 24.3 ± 0.1 |
Cholinesterase Activity | ||
AChE (Inhibition %) | 40.9 ± 0.2 | 13.7 ± 0.2 |
BChE (Inhibition %) | 25.0 ± 0.1 | 54.3 ± 0.3 |
Flower Hydro-Distillate (FH) | Root Hydro-Distillate (RH) | |||||||
---|---|---|---|---|---|---|---|---|
4 h | 24 h | 48 h | 72 h | 4 h | 24 h | 48 h | 72 h | |
T24 | 362.6 | 21.4 | 23.8 | 16.0 | 517.7 | 267.5 | 676.0 | 366.8 |
TCCSUP | 418.4 | 15.2 | 7.8 | 49.9 | 519.1 | 326.0 | 258.3 | 316.9 |
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Blažević, I.; Đulović, A.; Čikeš Čulić, V.; Burčul, F.; Ljubenkov, I.; Ruščić, M.; Generalić Mekinić, I. Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential. Molecules 2019, 24, 741. https://doi.org/10.3390/molecules24040741
Blažević I, Đulović A, Čikeš Čulić V, Burčul F, Ljubenkov I, Ruščić M, Generalić Mekinić I. Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential. Molecules. 2019; 24(4):741. https://doi.org/10.3390/molecules24040741
Chicago/Turabian StyleBlažević, Ivica, Azra Đulović, Vedrana Čikeš Čulić, Franko Burčul, Ivica Ljubenkov, Mirko Ruščić, and Ivana Generalić Mekinić. 2019. "Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential" Molecules 24, no. 4: 741. https://doi.org/10.3390/molecules24040741