Insights into the Phytochemical and Multifunctional Biological Profile of Spices from the Genus Piper
Abstract
:1. Introduction
2. Materials and Methods
2.1. Plant Material and Extraction
2.2. Phytochemical Characterization
2.3. Antimicrobial Assay
2.4. Antioxidant, Cholinesterase, Amylase and Glucosidase Assays
2.5. Cell Viability Assay
2.6. Melanin Assay
2.7. Tyrosinase Assay
2.7.1. Mushroom Tyrosinase Assay
2.7.2. Murine Tyrosinase Assay
2.8. Statistical Analysis
3. Results and Discussion
3.1. Phytochemical Characterization
3.2. Antimicrobial Activity
3.3. Antioxidant Activity
3.4. Anti-Cholinesterase Activity
3.5. Anti-Amylase and Anti-Glucosidase Activity
3.6. Anti-Melanogenic Activity
3.7. Anti-Tyrosinase Activity
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Sample | Voucher | Extraction Yield | TPC (mg GAE/g) | TFC (mg RE/g) | |
---|---|---|---|---|---|
P. nigrum L. | Black1 | PN1/102019 | 10.5% | 40.96 ± 0.42 b | 10.03 ± 0.22 b |
Black2 | PN5/102019 | 10.9% | 40.80 ± 0.45 b | 9.12 ± 0.32 b | |
Black3 | PN6/102019 | 11.9% | 36.71 ± 0.18 c | 1.44 ± 0.15 e | |
White | PN2/1020219 | 7.7% | 42.11 ± 1.06 b | 4.66 ± 0.30 c | |
Green | PN3/102019 | 12.5% | 58.90 ± 1.84 a | 18.37 ± 0.27 a | |
Red | PN4/102019 | 14.5% | 41.41 ± 1.00 b | 5.42 ± 0.32 c | |
P. longum L. | PL1/112019 | 18.3% | 29.53 ± 0.25 d | 3.01 ± 0.03 d | |
P. retrofractum Vahl. | PR1/112019 | 10.1% | 32.60 ± 0.22 e | 19.70 ± 0.13 d |
No. | Compound | UV [nm] | HRMS (+) [m/z] | MF | HRMS/MS (+) [m/z] |
---|---|---|---|---|---|
1 | Piperolactam C | 220; 340 | 310.1075 | C18H15NO4 | 193.0750; 120.0395 |
2 | Piperlongumine | 230; 330 | 318.1360 | C17H19NO5 | 269.0957; 221.0805; 201.0527 |
3 | Piperyline | 255; 310; 342 | 272.1291 | C16H17NO3 | 201.0555; 173.0572; 143.0503; 135.0405; 115.0571 |
4 | Piperlonguminine | 230; 340 | 274.1452 | C16H19NO3 | 161.0576; 135.0452 |
5 | Piperine | 240; 310; 341 | 286.1443 | C17H19NO3 | 201.0542; 173.0525; 135.0455; 112.0733 |
6 | Piperettines | 310; 345 | 312.1605 | C19H21NO3 | 227.0679; 199.0776; 169.0555; 141.085; 131.0405 |
7 | Piperolein A | 260; 340 | 316.1904 | C19H25NO3 | 231.1056; 161.0538; 135.0512 |
8 | Pellitorine | 210; 260 | 224.2015 | C14H25NO | 168.1414; 151.1170; 123.1196; 109.0603 |
9 | Pipercallosine | 210; 265; 310 | 330.2049 | C20H27NO3 | 259.1312; 241.1301; 208.1725; 135.0490 |
10 | Dehydropipernonaline | 210; 265 | 340.1919 | C21H25NO3 | 227.1001; 161.0554; 131.0414 |
11 | Pipernonaline | 215; 260; 305 | 342.2065 | C21H27NO3 | 229.1564; 199.0916; 161.0593; 135.0471 |
12 | Neopeollitorine B | 210; 265 | 236.2001 | C15H25NO | 151.1140; 109.0625 |
13 | Retrofractamide B | 210; 260 | 356.2203 | C22H29NO3 | 283.1309; 255.1371; 234.1822; 215.1868; 135.0433 |
14 | Piperolein B | 210; 265; 305 | 344.2205 | C21H29NO3 | 259.1299; 222.1829; 135.0395 |
15 | Piperundecalidine | 215; 270 | 368.2223 | C23H29NO3 | 246.1807; 215.1046; 173.0559; 135.0411 |
16 | Guineensine | 215; 260; 315 | 384.2586 | C24H33NO3 | 311.1985; 283.2033; 161.0754; 135.0577 |
17 | N-Isobutyl-2,4,12-octadecatrienamide | 220; 260 | 334.3099 | C22H39NO | 261.2253; 233.2201 |
No. | Compound | P. nigrum | P. longum | P. retrofractum | |||||
---|---|---|---|---|---|---|---|---|---|
Black 1 | Black 2 | Black 3 | White | Green | Red | ||||
mg PE/g Extract | |||||||||
1 | Piperolactam C | nq | nq | nq | nq | nq | nq | nq | 18.17 ± 0.25 a |
2 | Piperlongumine | nq | nq | nq | nq | nq | nq | nq | 14.19 ± 0.14 a |
3 | Piperyline | 11.66 ± 0.17 c | 12.68 ± 0.16 b | 8.62 ± 0.18 e | 10.90 ± 0.08 d | 15.40 ± 0.34 a | 5.81 ± 0.07 f | nq | nq |
4 | Piperlonguminine | 4.90 ± 0.12 d | 4.84 ± 0.26 d | 2.83 ± 0.13 e | 2.72 ± 0.15 f | 6.01 ± 0.14 c | 5.10 ± 0.13 d | 16.87 ± 0.13 a | 12.93 ± 0.03 b |
5 | Piperine | 276.70 ± 0.82 d | 299.63 ± 0.99 c | 293.07 ± 0.71 c | 308.36 ± 0.50 b | 315.19 ± 1.12 a | 154.03 ± 0.21 f | 249.79 ± 0.99 e | 93.86 ± 0.13 g |
6 | Piperettines | 70.60 ± 1.69 a | 64.65 ± 0.46 b | 46.12 ± 0.67 c | 66.18 ± 0.87 b | 70.69 ± 0.06 a | 21.51 ± 0.08 d | 3.64 ± 0.40 e | nq |
7 | Piperolein A | 28.83 ± 1.60 a | 17.96 ± 0.28 c | 9.93 ± 0.16 d | 28.97 ± 0.66 a | 23.90 ± 0.54 b | 5.84 ± 0.12 e | nq | 23.00 ± 1.21 b |
8 | Pellitorine | 39.68 ± 0.14 b | 15.95 ± 0.10 e | 22.41 ± 0.26 d | 26.11 ± 0.17 c | 18.78 ± 0.15 e | 9.33 ± 0.07 f | 7.90 ± 0.35 g | 206.95 ± 0.22 a |
9 | Pipercallosine | 3.72 ± 0.51 c | 3.28 ± 0.15 d | 3.02 ± 0.06 d | 4.72± 0.37 b | 4.57 ± 0.18 b | 2.04 ± 0.04 e | 9.25 ± 0.47 a | nq |
10 | Dehydropipernonaline | 22.23 ± 0.29 a | 11.18 ± 0.09 e | 18.50 ± 0.46 b | 17.12 ± 0.17 c | 12.77 ± 0.12 d | 2.68 ± 0.04 f | 12.71 ± 0.29 d | nq |
11 | Pipernonaline | 3.37 ± 0.12 c | nq | 2.14 ± 0.20 d | 5.60 ± 0.44 b | nq | nq | 47.62 ± 0.29 a | nq |
12 | Neopeollitorine B | 7.89 ± 0.65 a | 3.26 ± 0.10 c | 2.73 ± 0.20 d | 2.31 ± 0.36 d | 3.14 ± 0.01 c | nq | nq | 6.51 ± 0.25 b |
13 | Retrofractamide B | 22.07 ± 0.57 a | 13.28 ± 0.21 d | 6.14 ± 0.06 f | 6.75 ± 0.31 e | 19.75 ± 0.21 b | 12.65 ± 0.12 d | 14.63 ± 0.07 c | nq |
14 | Piperolein B | 17.26 ± 0.10 a | 12.46 ± 0.27 d | 11.02 ± 0.01 e | 13.17 ± 0.24 c | 15.35 ± 0.20 b | 3.20 ± 0.06 f | nq | 2.70 ± 0.01 g |
15 | Piperundecalidine | 7.66 ± 0.46 a | 4.07 ± 0.09 c | 4.86 ± 0.06 b | nq | 4.28 ± 0.16 c | 4.19 ± 0.10 c | 6.32 ± 0.19 d | 7.48 ± 0.11 a |
16 | Guineensine | 42.53 ± 0.08 a | 14.18 ± 0.33 e | 28.57 ± 0.12 c | 11.95 ± 0.04 f | 29.59 ± 0.16 b | 10.22 ± 0.05 g | 24.51 ± 0.25 d | 29.73 ± 0.05 b |
17 | N-Isobutyl-2,4,12-octadecatrienamide | 32.31 ± 0.37 d | 14.18 ± 0.21 e | 49.44 ± 0.33 b | 13.61 ± 0.19 f | 37.62 ± 0.20 c | 12.64 ± 0.05 g | 82.65 ± 0.25 a | 1.98 ± 0.05 h |
Total piperamides | 591.42 ± 4.01 a | 525.35 ± 4.10 b | 588.42 ± 6.44 a | 247.75 ± 0.87 f | 530.67 ± 1.49 b | 453.58 ± 7.63 d | 475.89 ± 1.05 c | 423.72 ± 2.49 e |
Microbial Species | P. nigrum | P. longum | P. retrofractum | Reference drug | |||||
---|---|---|---|---|---|---|---|---|---|
Black 1 | Black 2 | Black 3 | White | Green | Red | ||||
MIC (mg/mL) | MIC (mg/L) | ||||||||
S. aureus ATCC 25923 | 4 | 0.25 | 0.5 | 0.125 | 0.5 | 1 | 4 | 0.25 | 0.98 1 |
S. epidermidis ATCC 12228 | >4 | 2 | 4 | 4 | 0.125 | 0.5 | 4 | 4 | 0.98 1 |
M. luteus ATCC 10240 | 0.125 | 0.125 | 0.25 | 0.125 | 0.25 | 0.5 | 1 | 0.5 | 0.12 1 |
B. cereus ATCC 10876 | 0.5 | 1 | 0.5 | 0.5 | 2 | 2 | 4 | 0.5 | 0.98 1 |
E. faecalis ATCC 29212 | >4 | >4 | >4 | 4 | 4 | >4 | 4 | >4 | 1.95 1 |
S. mutans ATCC 25175 | 4 | 4 | 4 | 4 | 4 | 4 | >4 | 4 | 0.98 1 |
A. israelii ATCC 10049 | 0.125 | 0.125 | 0.0625 | 0.0625 | 0.125 | 0.5 | 0.5 | 0.25 | 0.5 1 |
C. perfringens ATCC 13124 | 2 | 2 | 2 | 2 | 4 | 4 | 4 | 2 | 1.95 3 |
C. jejunii ATCC 33291 | 4 | >4 | 2 | 4 | 4 | >4 | >4 | >4 | 0.125 2 |
S. Typhimurium ATCC14028 | >4 | >4 | >4 | >4 | 4 | >4 | >4 | >4 | 0.061 2 |
E. coli ATCC 25922 | >4 | >4 | >4 | >4 | 4 | >4 | >4 | >4 | 0.015 2 |
P. mirabilis ATCC 12453 | >4 | >4 | >4 | >4 | 2 | 2 | >4 | >4 | 0.03 2 |
K. pneumoniae ATCC 13883 | >4 | >4 | >4 | >4 | 4 | >4 | >4 | >4 | 0.122 2 |
P. aeruginosa ATCC 9027l | >4 | >4 | >4 | >4 | 4 | >4 | >4 | >4 | 0.488 2 |
B. fragilis ATCC 10240 | 0.5 | 0.25 | 0.25 | 0.25 | 0.5 | 1 | 1 | 1 | 0.98 3 |
P. intermedia ATCC 25611 | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 | >4 | 0.5 | 0.25 | 0.488 3 |
F. nucleatum ATCC 25586 | 0.125 | 0.125 | 0.0625 | 0.125 | 0.0625 | 0.125 | 0.25 | 0.0625 | 1.95 3 |
V. parvula ATCC 10790 | 0.25 | 0.25 | 0.125 | 0.25 | 0.25 | 1 | 1 | 2 | 1.95 3 |
C glabrata ATCC 90030 | 2 | 2 | 2 | 4 | 2 | 4 | 4 | 2 | 0.24 4 |
C. albicans ATCC 102231 | 1 | 1 | 0.5 | 1 | 1 | 1 | 2 | 1 | 0.48 4 |
C. parapsilosis ATCC 22019 | 0.5 | 0.5 | 0.25 | 0.5 | 0.5 | 0.5 | 2 | 0.5 | 0.24 4 |
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Luca, S.V.; Gaweł-Bęben, K.; Strzępek-Gomółka, M.; Czech, K.; Trifan, A.; Zengin, G.; Korona-Glowniak, I.; Minceva, M.; Gertsch, J.; Skalicka-Woźniak, K. Insights into the Phytochemical and Multifunctional Biological Profile of Spices from the Genus Piper. Antioxidants 2021, 10, 1642. https://doi.org/10.3390/antiox10101642
Luca SV, Gaweł-Bęben K, Strzępek-Gomółka M, Czech K, Trifan A, Zengin G, Korona-Glowniak I, Minceva M, Gertsch J, Skalicka-Woźniak K. Insights into the Phytochemical and Multifunctional Biological Profile of Spices from the Genus Piper. Antioxidants. 2021; 10(10):1642. https://doi.org/10.3390/antiox10101642
Chicago/Turabian StyleLuca, Simon Vlad, Katarzyna Gaweł-Bęben, Marcelina Strzępek-Gomółka, Karolina Czech, Adriana Trifan, Gokhan Zengin, Izabela Korona-Glowniak, Mirjana Minceva, Jürg Gertsch, and Krystyna Skalicka-Woźniak. 2021. "Insights into the Phytochemical and Multifunctional Biological Profile of Spices from the Genus Piper" Antioxidants 10, no. 10: 1642. https://doi.org/10.3390/antiox10101642