In Vitro Anticariogenic Effects of Drymocallis rupestris Extracts and Their Quality Evaluation by HPLC-DAD-MS3 Analysis
Abstract
:1. Introduction
2. Results and Discussion
2.1. Determination of Polyphenolic Compounds
Extracts | Total phenolic content (TPC) (mg GAE/g dry weight) a |
---|---|
PRU | 26.7 ± 0.8 |
PRU1 | 23.2 ± 0.5 |
PRU2 | 29.9 ± 0.7 |
PRU3 | 30.9 ± 1.1 |
PRU4 | 22.5 ± 0.9 |
Polyphenols content (mg/g dry weight) a | ||||
---|---|---|---|---|
Phenolic acids (TPA) | Flavonoids (TFC) | Tannins (TTC) | Proanthocyanidins (TPDC) | |
Quercetin | Hyperoside | |||
7.8 ± 0.4 | 4.2 ± 0.3 | 6.0 ± 0.5 | 115.0 ± 3.7 | 4.6 ± 0.4 |
2.2. Anticariogenic activity
Identified compounds | Retention time [min] | UV [nm] | [M-H]− m/z | MS2 ions | MS3 ions | [M+H]+ | MS2 ions | MS3 ions | |
---|---|---|---|---|---|---|---|---|---|
1 | HHDP-glucose | 2.1 | 260 | 481 | 421, 301b | - | - | - | - |
2 | unknown compound | 2.6 | 220, 258 | 639 | 613, 463b, 301 | - | 641 | - | - |
3 | unknown tannin | 2.7 | 257 | 783 | - | - | 785 | - | - |
4 | gallic acid * | 2.7 | 266 | 169 | 125b | - | 171 | 127b | - |
5 | unknown compound | 2.8 | 262 | 447 | 315b, 297, 207, 177, 163 | - | - | - | - |
6 | unknown tannin | 5.4 | 248 | 391a, 783 | 481, 421, 301b, 275 | - | 785 | 767b, 465, 303 | - |
7 | unknown tannin | 6.7 | 249 | 391a, 783 | 481, 421, 301b, 275 | - | 785 | 767b, 465, 303 | - |
8 | bis-HHDP-glucose isomer | 9.0 | 216, 260 sh | 783 | 481, 421, 301b | - | 785 | 767b, 465, 303 | - |
9 | bis-HHDP-glucose isomer | 12.2 | 250 | 783 | 481, 301b, 275 | - | - | - | - |
10 | methyl gallate * | 13.0 | 271 | 183 | 167b | - | 185 | 153b | - |
11 | bis-HHDP-glucose isomer | 14.8 | 216, 260 sh | 783 | 481, 421, 301b | - | 785 | 767b, 465, 303 | - |
12 | galloyl-HHDP-glucose isomer | 15.2 | 271 | 633 | 463, 301b | - | 657b | - | - |
13 | brevifolincarboxilic acid | 18.1 | 245, 296, 324 | 291 | 247b, 279 | - | 293 | 257, 169 | - |
14 | quercetin derivative | 18.3 | 260, 350 | 757 | 595b | 463, 445, 343, 301b | 759 | 627, 465b, 303 | 465b, 303 |
15 | quercetin glucuronylhexoside | 19.2 | 273, 353 | 639 | 463b, 301 | 343, 301b | 641 | 465b, 303 | 303b |
16 | caffeoylquinic acid isomer | 23.8 | 234 sh, 303 sh, 327 | 353 | 191, 173b, 155, 127, 111 | - | 377b | 243, 215b, 197, 185 | - |
17 | ellagic acid derivative | 24.0 | 255, 261 | 469 | 451, 425b, 301, 167 | - | 493b | 475b, 452, 409, 333 | - |
18 | unknown flavonoid | 25.1 | 259, 295 sh, 357 | 399 | 273b | - | 401 | 275b, 247 | - |
19 | ellagic acid 3,3'-di-O-methyl ether 4-O-xyloside * | 25.2 | 250, 325 | 461 | 415b, 301 | - | 463 | 445, 331b, 275 | 271, 257b, 169 |
20 | unknown compound | 27.3 | 274 | 247 | 219, 191b | - | 249 | 207b, 186 | - |
21 | unknown compound | 27.4 | 224 sh, 266, 302 | 275 | 257b, 229, 203 | - | 277 | 259b, 249, 215 | - |
22 | |||||||||
23 | unknown flavonoid | 31.6 | 270, 350 | 639 | 459b, 444, 315 | - | 641 | 479, 317b | 461, 413, 317b |
24 | unknown compound | 31.9 | 270, 360 | 365 | 183b, 153 | - | 367 | 335b, 303 | - |
25 | quercetin pentosylglucuronide | 32.5 | 258, 351 | 609 | 301b, 179 | - | 633b, 611 | 597, 479b, 303 | 303 |
26 | unknown flavonoid | 34.6 | 250, 351 | 447 | 369, 301b | - | 449 | 303b | 285b, 275, 258 |
27 | ellagic acid * | 35.5 | 253, 362 | 301 | 284, 257b, 185 | - | 303 | 285b, 248 | - |
28 | uknown compound | 35.9 | slope | 435 | 303b, 285, 177 | 285b, 177 | 459b | 441, 412, 356, 327b, 307, 251 | - |
29 | quercetin 3-O-glucuronide * | 37.0 | 252, 350 | 477 | 301b | 273, 179b, 151 | 479 | 303b | 285, 257b, 227, 165 |
30 | unknown compound | 38.1 | 226, 292 | 435 | 303b, 285, 177 | 285b, 177, 125 | - | - | - |
31 | unknown compound | 38.5 | 264, 290 sh, 350 | 457 | 273b, 245 | - | 459 | 427b, 275, 261 | - |
32 | quercetin 3-O-arabinoside * | 41.4 | 267, 351 | 433 | 301b | - | 435 | 303b | 285, 275, 257b, 207, 165 |
33 | unknown flavonoid pentoside | 41.7 | 250, 361 | 447 | 315b, 300 | 299 | 449 | 317b, 286 | 286 |
34 | kaempferol 3-O-glucoside * | 41.9 | 265, 340 | 447 | 327, 299, 285b, 255 | - | 449 | 287b | 269, 241, 213, 153, 121b |
35 | kaempferol 3-O-glucuronide * | 42.5 | 265, 348 | 461 | 285b | 267, 257b, 241, 229, 213, 197, 185 | 463 | 287b | 241, 213, 127b |
36 | ellagic acid derivative | 42.6 | 255, 366 | 483 | 451b, 407, 315, 301 | - | 485 | 471, 453b, 435 | - |
37 | valoneic acid dilactone methyl ester * | 43.3 | 255, 366 | 483 | 451b, 407, 315, 301 | - | 485 | 471, 453b, 435 | - |
38 | isorhamnetin glucuronide | 44.1 | 257, 265 sh, 355 | 491 | 473, 315b, 301 | 300b, 287, 272 | 493 | 303b | - |
39 | ellagic acid derivative | 45.3 | 257, 355 | 457 | 275b | - | 459 | 427, 409b, 399, 257 | - |
40 | unknown compound | 50.0 | 267, 315 | 445 | 265, 235, 205, 163, 145b | - | 469b | 377, 306, 173, 147b | - |
41 | quercetin* | 56.7 | 255, 368 | 301 | 273, 257, 229, 179b, 151 | - | 303 | 275b, 257, 230, 165 | - |
42 | unknown compound | 57.4 | 253, 267 | 483 | 251b, 301 | - | 485 | 453b | - |
43 | tiliroside* | 59.3 | 267, 311, 354 sh | 593 | 447, 285b | 285 | 595 | 329, 309, 287b, 165 | - |
44 | unknown flavonoid | 59.9 | 267, 315, 360 sh | 623 | 461, 447, 332b, 299, 285 | 341, 299, 285 | 625 | 339b, 321, 287, 177 | - |
45 | tiliroside isomer | 61.1 | 267, 308, 351 sh | 593 | 447, 307, 285b | 327, 285b, 255 | 595 | 392, 309, 287b | - |
Tested strains | MIC (mg/mL) | MBC (mg/mL) | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
PRU | PRU1 | PRU2 | PRU3 | PRU4 | CHX a | PRU | PRU1 | PRU2 | PRU3 | PRU4 | CHX a | |
S. sobrinus/downei 21020 | >12 | >12 | 1.5 | >12 | >12 | 3.125 × 10−3 | >12 | >12 | 1.5 | >12 | >12 | 6.25 × 10−3 |
S. sobrinus DSM 20381 | >12 | >12 | 0.75 | >12 | >12 | 3.125×10−3 | >12 | >12 | 1.5 | >12 | >12 | 3.125×10−3 |
S. mutans 6067 | 6 | 6 | 1.5 | 6 | >12 | 3.125 × 10−3 | 12 | 12 | 3 | 12 | >12 | 3.125×10−3 |
S. sobrinus 6070 | >12 | 6 | 1.5 | 6 | >12 | 3.125 × 10−3 | >12 | 12 | 3 | 12 | >12 | 6.25×10−3 |
S. sanguis ATCC 10556 | >12 | 3 | 1.5 | 3 | >12 | 3.125 × 10−3 | >12 | 6 | 3 | 6 | >12 | 6.25×10−3 |
3. Experimental
3.1. Plant material
3.2. Preparation of Extracts and Their Subfractions
3.3. Phytochemical Profile
3.3.1. Determination of Total Polyphenol Content
3.3.2. Determination of Total Phenolic Acids Content
3.3.3. Determination of Total Flavonoid Content
3.3.4. Determination of Total Tannin Content
3.3.5. Determination of Total Proanthocyanidin Content
3.3.6. HPLC-DAD-MS3 Analysis
3.4. Anticariogenic Activity
3.4.1. Bacterial Strains
3.4.2. Determination of Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC)
3.4.3. Inhibition of Biofilm Formation
3.4.4. Inhibition of streptococcal α-d-glucans synthesis
3.5. Data Analysis
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Tomczyk, M.; Pleszczyńska, M.; Wiater, A.; Granica, S. In Vitro Anticariogenic Effects of Drymocallis rupestris Extracts and Their Quality Evaluation by HPLC-DAD-MS3 Analysis. Molecules 2013, 18, 9117-9131. https://doi.org/10.3390/molecules18089117
Tomczyk M, Pleszczyńska M, Wiater A, Granica S. In Vitro Anticariogenic Effects of Drymocallis rupestris Extracts and Their Quality Evaluation by HPLC-DAD-MS3 Analysis. Molecules. 2013; 18(8):9117-9131. https://doi.org/10.3390/molecules18089117
Chicago/Turabian StyleTomczyk, Michał, Małgorzata Pleszczyńska, Adrian Wiater, and Sebastian Granica. 2013. "In Vitro Anticariogenic Effects of Drymocallis rupestris Extracts and Their Quality Evaluation by HPLC-DAD-MS3 Analysis" Molecules 18, no. 8: 9117-9131. https://doi.org/10.3390/molecules18089117