5-CQA and Mangiferin, Two Leaf Biomarkers of Adaptation to Full Sun or Shade Conditions in Coffea arabica L.
Abstract
:1. Introduction
2. Results
2.1. Identification of Phenolic Compounds in Mature Leaves of C. arabica Using LC-MS2
2.2. Influence of Light Intensity on Leaf Phenolic Content in One C. arabica Cultivar at Low or High Elevation
2.3. Influence of Light Intensity on the Leaf Phenolic Content of Numerous C. arabica Genotypes Grown in Different Environments
2.4. Influence of C. arabica Genetic Groups on Leaf Phenolic Contents in Two Different Environments
3. Discussion
3.1. LC-MS2 Analysis Enabled Identification of Two Novel Mangiferin Derivatives in C. arabica
3.2. Identification of Leaf Phenolic Contents as Biomarkers of Adaptation of C. arabica to Full-Sun or Shade Conditions
3.2.1. Preselection of Candidate Biomarkers of Adaptation of C. arabica to Full-Sun Conditions
3.2.2. Selection of Biomarkers for Adaptation of C. arabica to Full Sunlight Using Genetic Diversity and Contrasting Environments
3.2.3. Influence of C. arabica Genotype on the Phenolic Leaf Contents and Selection of Biomarkers of Adaptation to Full Sunlight or Shade in Breeding Programs
4. Materials and Methods
4.1. Locations and Plant Material
4.2. Leaf Sampling for Secondary Metabolite Analysis
4.3. Secondary Metabolite Analysis
4.4. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
Amu | atomic mass unit |
APL | American pure lines |
CGAs | chlorogenic acid group (CQA, diCQA, Coum-QA and FQA) |
Coum-QA | coumaroyl quinic acid |
3-CQA | 3-O-caffeoylquinic acid |
4-CQA | 4-O-caffeoylquinic acid |
5-CQA | 5-O-caffeoylquinic acid |
3,4-diCQA | 3,4-O-dicaffeoylquinic acid |
3,5-diCQA | 3,5-O-dicaffeoylquinic acid |
4,5-diCQA | 4,5-O-dicaffeoylquinic acid |
EWA | Ethiopian wild accessions |
F-dihex | flavone-di-C-hexose |
FQA | feruloylquinic acid |
HF1 | hybrid F1 clone |
HPLC-DAD | High performance liquid chromatograph/ photodiode array detection |
K-dihex-dhex | kaempferol-3-O-di-hexose-deoxyhexose |
K-hex-dhex | kaempferol-3-O-hexose-deoxyhexose |
LC-DAD-MS2 | High performance liquid chromatograph/ photodiode array detection /mass spectrometry2 |
pOH Mang | mangiferin parahydroxybenzoate |
Q-dihex-dhex | quercetin-3-O-dihexose-deoxyhexose |
Q-diGlu | quercetin-3-O-diglucoside |
SNP | single-nucleotide polymorphism |
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Peak N° | RT (min) | Mass (Da) | Molecular Formula | Wavelength (nm) | Compound Name | [M − H]− | MS2 | [M+H]+ | MS2 |
---|---|---|---|---|---|---|---|---|---|
1 | 2.61 | 180.1640 | C7H8N4O2 | 272 | Theobromine * | - | 181.0718 | 67 (100) 85 (78) 181 (74) 138 (65) 69 (61) 108 (61) 56 (43) 163 (43) 122 (28) 117 (13) 156 (9) | |
2 | 3.00 | 354.3087 | C16H18O10 | 300sh-325 | 3-O-Caffeoylquinic acid | 353.0901 | 191 (100) 179 (61) 135 (47) 173 (6) | 355.1002 | 163 (100) 145 (24) 89 (9) |
3 | 4.02 | 408.3561 | C19H20O10 | 286 | Iriflophenone-C-hexose | 407.1012 | 287 (100) 317 (23) 245 (61) 193 (47) 125 (8) | 409.1107 | 195 (100) 231 (79) 13 (61) 325 (46) 177 (43) 121 (39) 271 (39) 355 (14) 85 (7) |
4 | 4.20 | 290.2700 | C15H14O6 | 278 | (+)-Catechin * | 289.0769 | 109 (100) 123 (69) 125 (64) 203 (56) 151 (44) 245 (40) 137 (36) 205 (26) 97 (25) 121 (23) 289 (21) 187 (21) 188 (20) 149 (20) 221 (20) 161 (20) | 291.0858 | 139 (100) 123 (59) 147 (23) 161 (12) 207 (6) |
5 | 4.42 | 354.3087 | C16H18O10 | 300sh-325 | 5-O-Caffeoylquinic acid * | 353.0901 | 191 (100) 161 (2) 179 (2) 173 (1) | 355.1002 | 163 (100) 145 (11) 164 (11) 135 (4) 117 (3) 89 (2) |
6 | 4.74 | 354.3087 | C16H18O10 | 300sh-325 | 4-O-Caffeoylquinic acid | 353.0901 | 173 (100) 191 (85) 179 (73) 135 (51) 93 (20) | 355.1002 | 163 (100) 145 (14) 164 (9) 117 (6) 135 (5) 89 (4) |
7 | 4.90 | 194.1900 | C8H10N4O2 | 272 | Caffeine * | - | 195.089 | 138 (100) 110 (36) 195 (29) 69 (21) | |
8 | 5.42 | 290.2700 | C15H14O6 | 278 | (-)-Epicatechin * | 289.0709 | 109 (100) 125 (74) 203 (69) 123 (60) 151 (43) 245 (40) 137 (37) 205 (34) 161 (26) 97 (23) 188 (23) 221 (22) 187 (20) 121 (20) 179 (20) 289 (19) | 191.0844 | 139 (100) 123 (63) 147 (24) 161 (12) 207 (6) |
9 | 5.62 | 338.3093 | C16H18O8 | 310 | 5-O-Coumaroylquinic acid | 337.0953 | 191 (100) 133 (17) 53 (12) 93 (12) 253 (12) 145 (10) 75 (2) 302 (2) | 339.1085 | 147 (100) 75 (23) 97 (23) 236 (23) 127 (19) 258 (16) 341 (16) 65 (10) 189 (10) 217 (10) 306 (10) |
10 | 6.08 | 422.3400 | C19H18O11 | 257-317-365 | Mangiferin * | 421.0799 | 301 (100) 331 (85) 259 (12) 421 (15) 273 (10) | 423.0906 | 273 (100) 303 (74) 327 (51) 369 (22) 351 (18) 299 (15) 357 (9) |
11 | 6.79 | 368.3353 | C17H20O9 | 258-267sh-300sh-327 | 5-O-Feruloylquinic acid | 367.1058 | 191 (100) 93 (21) 173 (11) 111 (7) 134 (4) | 369.1157 | 177 (100) 145 (42) 117 (5) |
12 | 6.81 | 594.5181 | C27H30O15 | 256(sh)-265-330 | Flavone di-C-hexose | 593.1555 | 593 (100) 473 (11) 353 (10) 406 (10) 503 (8) | 595.1643 | 457 (100) 427 (67) 379 (35) 325 (29) 295 (12) |
13 | 6.86 | 772.6581 | C33H40O21 | 257-300sh-353 | Quercetin-3-O-dihexose-deoxyhexose | 771.2036 | 771 (100) 300 (53) 179 (5) 273 (5) 271 (5) | 773.2129 | 303 (100) 125 (53) 84 (26) 194 (13) |
14 | 6.97 | 626.5169 | C27H30O17 | 257-300sh-353 | Quercetin-3,4-di-O-glucoside * | 625.1449 | 625 (100) 300 (72) 271 (10) 179 (3) 445 (3) 463 (3) 505 (3) | 627.1514 | 303 (100) |
15 | 7.34 | 756.659 | C33H40O20 | 265-346 | Kaempferol-3-O-dihexose-deoxyhexose | 755.2128 | ND | 757.2131 | 287 (100) 449 (6) 129 (6) 757 (6) 612 (1) |
16 | 7.74 | 610.5175 | C27H30O16 | 257-353 | Quercetin-3-O-rutinoside * | 609.1539 | 609 (100) 300 (20) | 611.1595 | 303 (100) |
17 | 7.90 | 578.5202 | C30H26O12 | 276 | Procyanidin dimer | 577.1396 | 289 (100) 577 (83) 407 (72) 125 (61) 161 (17) 451 (11) | 579.1472 | 287 (100) 409 (94) 127 (84) 580 (64) 163 (31) 247 (19) 579 (13) |
18 | 7.96 | 464.3800 | C21H20O12 | 257-353 | Quercetin-3-O-glucoside * | 463.0908 | 300 (100) 463 (48) 191 (19) 271 (10) | 465.1018 | 303 (100) |
19 | 8.20 | 594.5181 | C27H30O15 | 265-346 | Kaempferol-3-O-hexose-deoxyhexose | 593.1540 | ND | 595.1629 | 287 (100) 596 (1) |
20 | 8.39 | 516.451 | C25H24O12 | 246-300sh-324 | 3,4-O-Dicaffeoylquinic acid * | 515.1221 | 173 (100) 353 (95) 179 (70) 191 (34) 354 (21) 515 (21) 335 (14) | 517.1323 | 163 (100) 63 (27) 140 (18) 191 (18) 370 (11) |
21 | 8.48 | 516.451 | C25H24O12 | 243-297sh-327 | 3,5-O-Dicaffeoylquinic acid * | 515.1229 | 191 (100) 353 (91) 179 (63) 135 (13) 173 (6) 515 (3) | 517.1323 | 140 (100) 163 (77) 519 (64) 213 (59) 117 (41) 303 (41) 189 (27) 238 (27) 367 (27) 442 (27) 492 (23) |
22 | 8.93 | 516.4510 | C25H24O12 | 243-297sh-327 | 4,5-O-Dicaffeoylquinic acid * | 515.1229 | 353 (100) 173 (92) 179 (53) 354 26) 191 (16) 135 (11) 137 (7) 203 (6) | 517.1323 | 163 (100) 111 (18) 383 (14) 435 (14) 224 (5) |
23 | 9.49 | 542.4451 | C26H22O13 | 257-317-365 | Mangiferin parahydroxybenzoate | 541.1017 | 301 (100) 331 (79) 541 (53) 259 (6) 385 (6) | 543.1118 | 303 (100) 121 (96) 405 (24) 327 (23) 543 (21) |
Phenolic Compounds | Light | Elevation | Elevation x Light | |||
---|---|---|---|---|---|---|
F | p | F | p | F | p | |
Chlorogenic Acids | ||||||
3-CQA | 1.72 | 0.198936 | 7.72 | 0.008836 | 0.00 | 0.954559 |
4-CQA | 0.05 | 0.823017 | 29.29 | 0.000005 | 5.81 | 0.021526 |
5-CQA | 18.69 | 0.000127 | 56.51 | 0.000000 | 28.72 | 0.000006 |
3,4-diCQA | 1.97 | 0.169890 | 35.48 | 0.000001 | 11.11 | 0.002085 |
3,5-diCQA | 6.88 | 0.012958 | 4.77 | 0.035947 | 11.71 | 0.001633 |
4,5-diCQA | 8.20 | 0.007112 | 49.98 | 0.000000 | 35.19 | 0.000001 |
FQA | 0.03 | 0.865203 | 0.23 | 0.633213 | 4.21 | 0.048007 |
Flavonoids | ||||||
Flavanols | ||||||
Epicatechin | 6.00 | 0.019604 | 63.86 | 0.000000 | 10.29 | 0.002912 |
Catechin | 0.13 | 0.717829 | 100.22 | 0.000000 | 23.80 | 0.000025 |
Glycosylated flavonoids | ||||||
K-dihex-dhex | 26.33 | 0.000012 | 29.04 | 0.000005 | 15.76 | 0.000353 |
K-hex-dhex | 117.43 | 0.000000 | 23.92 | 0.000024 | 29.81 | 0.000004 |
F-dihex | 16.15 | 0.000307 | 13.02 | 0.000980 | 8.79 | 0.005506 |
Q-dihex-dhex | 54.52 | 0.000000 | 11.64 | 0.001685 | 0.30 | 0.589041 |
Q-diGlu | 100.65 | 0.000000 | 23.18 | 0.000030 | 0.01 | 0.903435 |
Rutin | 142.72 | 0.000000 | 31.26 | 0.000003 | 0.02 | 0.881375 |
Xanthones | ||||||
Mangiferin | 31.19 | 0.000003 | 12.69 | 0.001112 | 2.39 | 0.131611 |
Country | Geographic Coordinates | Elevation (m asl) | Plant Density (m) | Plants for Each Half Plot: Full Sun or under Shade (N) | Annual Average Temperature Min/Max (°C) | Average Surface Temperature (°C) | Rain (mm by Year) | Global Horizontal Irradiation (kWh.m−2) |
---|---|---|---|---|---|---|---|---|
Mexico | 18°51′46″ N 96°51′35″ W | 650 | 2 × 1.5 | 192 | 18.6/31.4 | 19.1 | 2650 | 1890 |
Mexico | 19°23′43″ N 96°59′60″ W | 1250 | 2 × 1.5 | 192 | 14.2/28.2 | 17.0 | 2100 | 1848 |
Nicaragua | 13°2′45″ N 85°53′30″ W | 1200 | 2 × 1 | 950 | 14.1/24.0 | 18.7 | 1760 | 1706 |
Colombia | 4°58′17″ N 75°39′09″ W | 1380 | 1.3 × 1.5 for APL 1.5 × 1.5 for WEA | 490 | 17.4/26.8 | 22.1 | 3570 | 1851 |
Genotype | Genealogy | Origin | Genetic Group |
---|---|---|---|
Mexican experimental plot | |||
Marsellesa® | Timor hybrid CIFC 832/2 x cv. Villa Sarchi (Costa Rica) | CIRAD Nicaragua | APL of Sarchimor group |
Nicaraguan experimental plot | |||
ET08 A8 | EWA | Kaffa province, Ethiopia (ORSTOM prospecting, 1966) | “Jimma Bonga” (G1A) * |
ET47 A4 | Kaffa province, Ethiopia (FAO prospecting, 1964–1965) | ||
ET26 A1 | “Sheka” (G1B) * | ||
ET25 A4 | G1G2 * | ||
ET06 | Not yet characterized | ||
T5175 | Timor hybrid CIFC 832/1 x cv. Caturra | Instituto del Café of Costa Rica (ICAFE) | APL of Catimor group |
T8667 | Timor hybrid CIFC 832/1 x cv. Caturra | CATIE, Turrialba, Costa Rica | |
T5296 | Timor hybrid CIFC 832/2 x cv. Villa Sarchi | APL of Sarchimor group | |
T17931 | Timor hybrid CIFC1343 x cv. Caturra | APL Catimor line of the multiline var. Colombia | |
Catuaí | cv. Mundo Novo x cv. Caturra | Instituto Agronômico de Campinas (IAC), Brazil | APL non-introgressed dwarf cultivar |
T5175 x ET08 A8 | APL mother x EWA father F1 hybrid | CIRAD, Nicaragua | F1 hybrid clone |
T5175 x ET26 A1 | |||
T5175 x ET25 A4 | |||
T5175 x T17931 | APL mother x APL father F1 hybrid | ||
T8667 x ET47 A4 | APL mother x EWA father F1 hybrid | ||
T8667 x ET26 A1 | |||
T8667 x T5296 | APL mother x APL father F1 hybrid | ||
T5296 x T17931 | |||
T17931 x ET47 A4 | APL mother x EWA father F1 hybrid | ||
T17931 x ET26 A1 | |||
T17931 x ET25 A4 | |||
Catuaí x ET47 A4 | |||
Catuaí x ET26 A1 | |||
Colombian experimental plot | |||
E554 | EWA | Kaffa province, Ethiopia (FAO 1964-1965) | “Jimma Bonga” (G1A) * |
E286 | Kaffa province, Ethiopia (FAO 1964-1965) | “Jimma Bonga” (G1A) * | |
E057 | Kaffa province, Ethiopia (FAO 1964-1965) | “Jimma Bonga” (G1A) * | |
CX2385 | Timor hybrid CIFC1343 x cv. Caturra | CENICAFE, Colombia | APL of Catimor group |
CU1842 | |||
CX2385 x E554 | APL mother x EWA father F1 hybrid | F1 hybrid clone | |
CX2385 x E286 | |||
CX2385 x E057 | |||
CU 1842 x E554 | |||
CU 1842 x E286 | |||
CU 1842 x E057 |
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Share and Cite
Duangsodsri, T.; Villain, L.; Vestalys, I.R.; Michalet, S.; Abdallah, C.; Breitler, J.-C.; Bordeaux, M.; Villegas, A.M.; Raherimandimby, M.; Legendre, L.; et al. 5-CQA and Mangiferin, Two Leaf Biomarkers of Adaptation to Full Sun or Shade Conditions in Coffea arabica L. Metabolites 2020, 10, 383. https://doi.org/10.3390/metabo10100383
Duangsodsri T, Villain L, Vestalys IR, Michalet S, Abdallah C, Breitler J-C, Bordeaux M, Villegas AM, Raherimandimby M, Legendre L, et al. 5-CQA and Mangiferin, Two Leaf Biomarkers of Adaptation to Full Sun or Shade Conditions in Coffea arabica L. Metabolites. 2020; 10(10):383. https://doi.org/10.3390/metabo10100383
Chicago/Turabian StyleDuangsodsri, Teerarat, Luc Villain, Ialy Rojo Vestalys, Serge Michalet, Cécile Abdallah, Jean-Christophe Breitler, Mélanie Bordeaux, Andres Mauricio Villegas, Marson Raherimandimby, Laurent Legendre, and et al. 2020. "5-CQA and Mangiferin, Two Leaf Biomarkers of Adaptation to Full Sun or Shade Conditions in Coffea arabica L." Metabolites 10, no. 10: 383. https://doi.org/10.3390/metabo10100383