Chemotaxonomic Metabolite Profiling of 62 Indigenous Plant Species and Its Correlation with Bioactivities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemotaxonomic Metabolite Profiling of 62 Indigenous Korean Plant Species
No. | Putative Identification a | RT b (min) | UHPLC-LTQXL-IT-MS/MS | p-Value | Id g | ||||
---|---|---|---|---|---|---|---|---|---|
m/z Posi c | m/z Nega d | M.W. e | MSn Fragment Pattern f | UV (nm) | |||||
1 | Quinic acid | 1.02 | - | 191 | 192 | 173 | 214, 279 | 9.00E-04 | Ref. [33] |
2 | Gallic acid | 1.37 | - | 169 | 170 | - | 226, 272 | 3.00E-04 | STD |
3 | 6-Hydroxykaempferol-O-galloylhexoside | 7.09 | 617 | 615 | 616 | 463 > 301 | 221, 265, 352 | 2.00E-04 | Ref. [32] |
4 | Quercetin-3-O-arabinoside | 7.89 | 435 | 433 | 434 | 301 | 239, 368 | 8.00E-06 | Ref. [35] |
5 | Quercetin-3-O-rhamnoside | 8.08 | 449 | 447 | 448 | 301 > 151 | 232, 277 | 4.00E-06 | Ref. [35] |
6 | Dicaffeoylquinic acid | 8.28 | 517 | 515 | 516 | 353 > 191 | 214, 322 | 4.90E-03 | Ref. [33] |
7 | Kaempferol-3-O-rhamnoside | 8.61 | 433 | 431 | 432 | 285 | 228, 280 | 3.40E-03 | Ref. [35] |
8 | Kaempferol derivatives | 8.63 | 479 | 477 | 478 | 431 > 285 | 271, 281 | 4.60E-03 | Ref. [35] |
9 | Catechin | 8.72 | 291 | 289 | 290 | 245 | 213, 303 | 2.90E-03 | Ref. [36] |
10 | Isorhamnetin | 8.74 | 317 | 315 | 316 | 300 | 366 | 4.00E-04 | Ref. [32] |
11 | Digalloyl-hexoside | 8.8 | 485 | 483 | 484 | 169 | 276 | 2.29E-02 | Ref. [34] |
12 | N.I. 1 | 8.96 | 601 | 599 | 600 | 301 > 151 | 214, 268 | 1.60E-03 | |
13 | Kaempferol-7-O-rutinoside | 9.34 | 595 | 593 | 594 | 447 > 285 | 276 | 2.00E-09 | Ref. [33] |
14 | Quercetin | 9.69 | 303 | 301 | 302 | 151 | 214, 274 | 7.00E-04 | STD |
15 | Genistein | 10.47 | 271 | 269 | 270 | 253, 243, 215, 153 | 285, 318 | 3.70E-03 | STD |
16 | Patuletin | 10.59 | 333 | 331 | 332 | 287 | 269, 316 | 8.40E-03 | Ref. [32] |
17 | Kaempferol | 10.63 | 287 | 285 | 286 | - | 279 | 4.21E-02 | STD |
18 | N.I. 2 | 10.77 | 229 | 227 | 228 | 165 > 111 | 202, 280 | 7.00E-04 | |
19 | N.I. 3 | 10.88 | 329 | 327 | 328 | 197, 291 | 202, 279 | 3.00E-04 | |
20 | N.I. 4 | 11.95 | 309 | 307 | 308 | 289 > 271 | 206, 282, 314 | 1.57E-02 | |
21 | N.I. 5 | 12.97 | 313 | 311 | 312 | 293 > 275 | 218, 366 | 1.35E-02 | |
22 | N.I. 6 | 13.78 | 315 | 313 | 314 | 201 | 221, 279 | 5.00E-04 | |
23 | N.I. 7 | 14.53 | 529 | 527 | 528 | 277 > 233 | 226, 280 | 7.00E-04 | |
24 | N.I. 8 | 14.57 | 295 | 293 | 294 | 275, 195 | 226, 280 | 3.80E-03 |
2.2. Bioactivities of 62 Indigenous Korean Plant Species
2.3. Correlation of Metabolic Differences and Bioactivities in Plant Families
No. | Putative Identification a | RT b (min) | UHPLC-LTQXL-IT-MS/MS | p-Value | Id g | ||||
---|---|---|---|---|---|---|---|---|---|
m/z Posi c | m/z Nega d | M.W. e | MSn Fragment Patterns f | UV (nm) | |||||
1 | Quinic acid | 1.02 | - | 191 | 192 | 173 | 214, 279 | 4.00E-04 | Ref. [33] |
3 | 6-Hydroxykaempferol-O-galloylhexoside | 7.09 | 617 | 615 | 616 | 463 > 301 | 221, 265, 352 | 2.89E-02 | Ref. [32] |
4 | Quercetin-3-O-arabinoside | 7.89 | 435 | 433 | 434 | 301 | 239, 368 | 2.53E-02 | Ref. [35] |
5 | Quercetin-3-O-rhamnoside | 8.08 | 449 | 447 | 448 | 301 > 151 | 232, 277 | 4.70E-03 | Ref. [35] |
6 | Dicaffeoylquinic acid | 8.28 | 517 | 515 | 516 | 353 > 191 | 214, 322 | 4.76E-02 | Ref. [33] |
7 | Kaempferol-3-O-rhamnoside | 8.61 | 433 | 431 | 432 | 285 | 228, 280 | 3.95E-02 | Ref. [35] |
8 | Kaempferol derivative | 8.63 | 479 | 477 | 478 | 431 > 285 | 271, 281 | 3.63E-02 | Ref. [35] |
13 | Kaempferol-7-O-rutinoside | 9.34 | 595 | 593 | 594 | 447 > 285 | 276 | 9.00E-04 | Ref. [33] |
14 | Quercetin | 9.69 | 303 | 301 | 302 | 151 | 214, 274 | 9.00E-04 | STD |
17 | Kaempferol | 10.63 | 287 | 285 | 286 | 279 | 1.97E-02 | STD | |
20 | N.I. 4 | 11.96 | 309 | 307 | 308 | 289 > 235 | 214, 279 | 1.95E-02 | |
25 | Quercetin-O-pentoside | 7.83 | 435 | 433 | 434 | 301 | 217, 268 | 3.50E-03 | Ref. [32] |
26 | Apigenin | 10.47 | 271 | 269 | 270 | 269, 151 | 285, 318 | 4.01E-02 | STD |
27 | N.I. 9 | 10.74 | 661 | 659 | 660 | 202, 280 | 3.20E-03 |
3. Experimental Section
3.1. Chemicals and Reagents
3.2. Plant Materials
3.3. Sample Preparation
3.4. UHPLC-LTQ-XL-IT-MS/MS Analysis
No. | Family | Genus | Species | Collection Area | Collection Date |
---|---|---|---|---|---|
1 | Aceraceae | Acer | triflorum | Sangjung-ri, Geumgwang-myeon, Anseong-si, Gyeonggi-do | 2014-07-25 |
2 | Aceraceae | Acer | pictum | Sangjung-ri, Geumgwang-myeon, Anseong-si, Gyeonggi-do | 2014-07-25 |
3 | Aceraceae | Acer | buergerianum | Janghyeon-ri, Cheongna-myeon, Boryeong-si, Chungcheongnam-do | 2014-08-07 |
4 | Aceraceae | Acer | komarovii | Gohan-ri, Gohan-eup, Jeongseon-gun, Gangwon-do | 2014-08-30 |
5 | Aceraceae | Acer | tataricum | Gurae-ri, Sangdong-eup, Yeongwol-gun, Gangwon-do | 2014-08-30 |
6 | Aceraceae | Acer | pseudosieboldianum | Gohan-ri, Gohan-eup, Jeongseon-gun, Gangwon-do | 2014-08-30 |
7 | Aceraceae | Acer | pictum | Jeodong-ri, Ulleung-eup, Ulleung-gun, Gyeongsangbuk-do | 2014-07-16 |
8 | Aceraceae | Acer | palmatum | Mamyeong-ri, Naechon-myeon, Pocheon-si, Gyeonggi-do | 2014-08-08 |
9 | Asteraceae | Artemisia | capillaris | Nadae-ri, Yaro-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-08-21 |
10 | Asteraceae | Aster | pinnatifidus | Geogi-ri, Jusang-myeon, Geochang-gun, Gyeongsangnam-do | 2014-08-22 |
11 | Asteraceae | Bidens | bipinnata | Dongmak-ri, Yeoncheon-eup, Yeoncheon-gun, Gyeonggi-do | 2014-08-19 |
12 | Asteraceae | Conyza | canadensis | Sangdodae-ri, Sangchon-myeon, Yeongdong-gun, Chungcheongbuk-do | 2014-08-14 |
13 | Asteraceae | Erigeron | annuus | Dongmak-ri, Yeoncheon-eup, Yeoncheon-gun, Gyeonggi-do | 2014-08-05 |
14 | Asteraceae | Helianthus | tuberosus | Jiro-ri, Byeongyeong-myeon, Gangjin-gun, Jeollanam-do | 2014-08-12 |
15 | Asteraceae | Lactuca | indica | Gomo-ri, Soheul-eup, Pocheon-si, Gyeonggi-do | 2014-08-24 |
16 | Asteraceae | Saussurea | pulchella | Gohan-ri, Gohan-eup, Jeongseon-gun, Gangwon-do | 2014-08-30 |
17 | Asteraceae | Sigesbeckia | pubescens | Gurae-ri, Sangdong-eup, Yeongwol-gun, Gangwon-do | 2014-08-30 |
18 | Fabaceae | Albizia | julibrissin | Daechi-ri, Daechi-myeon, Cheongyang-gun, Chungcheongnam-do | 2014-08-06 |
19 | Fabaceae | Desmodium | caudatum | Seonheul-ri, Jocheon-eup, Jeju-si, Jeju special self-governing province | 2014-08-24 |
20 | Fabaceae | Lespedeza | bicolor | Sin-ri, Goryeong-eup, Goryeong-gun, Gyeongsangbuk-do | 2014-07-23 |
21 | Fabaceae | Lespedeza | cuneata | Geogi-ri, Jusang-myeon, Geochang-gun, Gyeongsangnam-do | 2014-08-22 |
22 | Fabaceae | Lespedeza | maximowiczii | Gohan-ri, Gohan-eup, Jeongseon-gun, Gangwon-do | 2014-08-30 |
23 | Fabaceae | Pueraria | lobata | Mamyeong-ri, Naechon-myeon, Pocheon-si, Gyeonggi-do | 2014-08-04 |
24 | Fabaceae | Robinia | pseudoacacia | Sin-ri, Goryeong-eup, Goryeong-gun, Gyeongsangbuk-do | 2014-10-23 |
25 | Fabaceae | Sophora | flavescens | Hanggok-ri, Gunbuk-myeon, Okcheon-gun, Chungcheongbuk-do | 2014-08-18 |
26 | Fabaceae | Sophora | japonica | Geogi-ri, Jusang-myeon, Geochang-gun, Gyeongsangnam-do | 2014-08-22 |
27 | Fagaceae | Castanea | crenata | Hasong-ri, Hwaseo-myeon, Sangju-si, Gyeongsangbuk-do | 2014-07-27 |
28 | Fagaceae | Castanopsis | sieboldii | Hannam-ri, Namwon-eup, Seogwipo-si, Jeju special self-governing province | 2014-08-25 |
29 | Fagaceae | Fagus | engleriana | Sadong-ri, Ulleung-eup, Ulleung-gun, Gyeongsangbuk-do | 2014-07-16 |
30 | Fagaceae | Quercus | mongolica | Hasong-ri, Hwaseo-myeon, Sangju-si, Gyeongsangbuk-do | 2014-07-27 |
31 | Fagaceae | Quercus | variabilis | Daechi-ri, Daechi-myeon, Cheongyang-gun, Chungcheongnam-do | 2014-08-06 |
32 | Fagaceae | Quercus | acuta | Hannam-ri, Namwon-eup, Seogwipo-si, Jeju special self-governing province | 2014-08-25 |
33 | Fagaceae | Quercus | aliena | Daechi-ri, Daechi-myeon, Cheongyang-gun, Chungcheongnam-do | 2014-09-19 |
34 | Fagaceae | Quercus | serrata | Mamyeong-ri, Naechon-myeon, Pocheon-si, Gyeonggi-do | 2014-08-05 |
35 | Betulaceae | Alnus | firma | Sin-ri, Goryeong-eup, Goryeong-gun, Gyeongsangbuk-do | 2014-07-23 |
36 | Betulaceae | Alnus | hirsuta | Sangjung-ri, Geumgwang-myeon, Anseong-si, Gyeonggi-do | 2014-07-25 |
37 | Betulaceae | Alnus | japonica | Yonggi-ri, Gibuk-myeon, Buk-gu, Pohang-si, Gyeongsangbuk-do | 2014-07-30 |
38 | Betulaceae | Betula | schmidtii | Icheon-ri, Sangbuk-myeon, Ulju-gun, Ulsan | 2014-08-01 |
39 | Betulaceae | Betula | dahurica | Ungyo-ri, Bangnim-myeon, Pyeongchang-gun, Gangwon-do | 2014-08-08 |
40 | Betulaceae | Betula | pendula | Sogye-ri, Hwanggan-myeon, Yeongdong-gun, Chungcheongbuk-do | 2014-08-14 |
41 | Betulaceae | Carpinus | cordata | Apgok-ri, Bongsan-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-07-24 |
42 | Betulaceae | Carpinus | turczaninowii | Jiro-ri, Byeongyeong-myeon, Gangjin-gun, Jeollanam-do | 2014-08-12 |
43 | Betulaceae | Carpinus | laxiflora | Seonheul-ri, Jocheon-eup, Jeju-si, Jeju special self-governing province | 2014-08-24 |
44 | Betulaceae | Corylus | heterophylla | Apgok-ri, Bongsan-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-07-24 |
45 | Rosaceae | Chaenomeles | sinensis | Ojeong-dong, Daedeok-gu, Daejeon | 2014-08-10 |
46 | Rosaceae | Crataegus | pinnatifida | Gurae-ri, Sangdong-eup, Yeongwol-gun, Gangwon-do | 2014-08-30 |
47 | Rosaceae | Eriobotrya | japonica | Jiro-ri, Byeongyeong-myeon, Gangjin-gun, Jeollanam-do | 2014-08-13 |
48 | Rosaceae | Pourthiaea | villosa | Seonheul-ri, Jocheon-eup, Jeju-si, Jeju special self-governing province | 2014-08-24 |
49 | Rosaceae | Prunus | armeniaca | Ojeong-dong, Daedeok-gu, Daejeon | 2014-07-20 |
50 | Rosaceae | Prunus | yedoensis | Janghyeon-ri, Cheongna-myeon, Boryeong-si, Chungcheongnam-do | 2014-08-07 |
51 | Rosaceae | Prunus | maackii | Gurae-ri, Sangdong-eup, Yeongwol-gun, Gangwon-do | 2014-08-30 |
52 | Rosaceae | Prunus | padus | Gohan-ri, Gohan-eup, Jeongseon-gun, Gangwon-do | 2014-05-22 |
53 | Rosaceae | Prunus | sp. | Gomo-ri, Soheul-eup, Pocheon-si, Gyeonggi-do | 2014-08-08 |
54 | Rosaceae | Pyrus | ussuriensis | Icheon-ri, Sangbuk-myeon, Ulju-gun, Ulsan | 2014-08-01 |
55 | Rosaceae | Rosa | multiflora | Nadae-ri, Yaro-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-08-21 |
56 | Rosaceae | Rubus | coreanus | Sogye-ri, Hwanggan-myeon, Yeongdong-gun, Chungcheongbuk-do | 2014-08-14 |
57 | Rosaceae | Rubus | crataegifolius | Nadae-ri, Yaro-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-08-21 |
58 | Rosaceae | Rubus | phoenicolasius | Nadae-ri, Yaro-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-08-21 |
59 | Rosaceae | Sanguisorba | officinalis | Nadae-ri, Yaro-myeon, Hapcheon-gun, Gyeongsangnam-do | 2014-08-21 |
60 | Rosaceae | Sorbus | commixta | Jeodong-ri, Ulleung-eup, Ulleung-gun, Gyeongsangbuk-do | 2014-07-16 |
61 | Rosaceae | Spiraea | prunifolia | Ungyo-ri, Bangnim-myeon, Pyeongchang-gun, Gangwon-do | 2014-08-08 |
62 | Rosaceae | Spiraea | salicifolia | Ungyo-ri, Bangnim-myeon, Pyeongchang-gun, Gangwon-do | 2014-08-08 |
3.5. Data Processing and Statistical Analysis
3.6. Bioactivity Assays
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Lee, S.; Oh, D.-G.; Lee, S.; Kim, G.R.; Lee, J.S.; Son, Y.K.; Bae, C.-H.; Yeo, J.; Lee, C.H. Chemotaxonomic Metabolite Profiling of 62 Indigenous Plant Species and Its Correlation with Bioactivities. Molecules 2015, 20, 19719-19734. https://doi.org/10.3390/molecules201119652
Lee S, Oh D-G, Lee S, Kim GR, Lee JS, Son YK, Bae C-H, Yeo J, Lee CH. Chemotaxonomic Metabolite Profiling of 62 Indigenous Plant Species and Its Correlation with Bioactivities. Molecules. 2015; 20(11):19719-19734. https://doi.org/10.3390/molecules201119652
Chicago/Turabian StyleLee, Sarah, Dong-Gu Oh, Sunmin Lee, Ga Ryun Kim, Jong Seok Lee, Youn Kyoung Son, Chang-Hwan Bae, Joohong Yeo, and Choong Hwan Lee. 2015. "Chemotaxonomic Metabolite Profiling of 62 Indigenous Plant Species and Its Correlation with Bioactivities" Molecules 20, no. 11: 19719-19734. https://doi.org/10.3390/molecules201119652