Supplementary Materials Phenolome of Asian Agrimony Tea (Agrimonia asiatica Juz., Rosaceae): LC-MS Profile, α-Glucosidase Inhibitory Potential and Stability
Nina I. Kashchenko * and Daniil N. Olennikov
Laboratory of Medical and Biological Research, Institute of General and Experimental Biology, Siberian Division, Russian Academy of Science, 6 Sakh’yanovoy Street, Ulan-Ude 670047, Russia; [email protected] (D.N.O.) * Correspondence: [email protected]; Tel.: +79-0216-00-627 (D.N.O.)
Received: date; Accepted: date; Published: date
Content
Table S1. Description of 85 Rosaceous plants used in study.
Table S2. Mass spectrometric parameters of compounds 1–60.
Foods 2020, 9, 1348; doi: 10.3390/foods9101348 www.mdpi.com/journal/foods Foods 2020, 9, 1348 2 of 9
Table S1. Description of 85 Rosaceous plants used in study.
Collection Species Collection place Coordinates date
51°41’15.4501’’ N, Republic Buryatia, Kyren Agrimonia pilosa Ledeb. 102°8’21.8127’’ E, 947 21.VII.2019 (Tunkinsky District) m
52°2’54.5243’’ N, Republic Buryatia, Kabansk Alchemilla anisopoda Juz. 106°37’34.5456’’ E, 461 23.VII.2019 (Kabansky District) m
51°38’53.0286’’ N, Republic Buryatia, Kolobki A. flavescens Buser 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m
55°38’56.8229’’ N, Republic Buryatia, A. subcrenata Buser 109°20’28.5324’’ E, 582 02.VIII.2019 Severobaykalsk m
Republic Buryatia, Podlopatki 50°54’50.8598’’ N, Armeniaca sibirica (L.) Lam. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
51°41’51.0445’’ N, Republic Buryatia, Zhemchug Chamaerhodos erecta (L.) Bunge 102°28’14.9261’’ E, 722 17.VII.2019 (Tunkinsky District) m 51°32’59.4879’’ N, Republic Buryatia, Tankhoy C. grandiflora (Pall. ex Schult.) Bunge 105°7’15.1616’’ E, 504 15.VII.2018 (Kabansky District) m 51°51’6.8316’’ N, Republic Buryatia, Zaigrayevo Cotoneaster lucidus Schltdl. 108°18’36.9388’’ E, 639 11.VII.2019 (Zaigraevsky District) m
51°1’54.8212’’ N, Cotoneaster melanocarpus Fisch. ex Republic Buryatia, Mukhorshibir 107°54’10.4700’’ E, 1003 18.VII.2019 Blytt (Mukhorshibirsky district) m
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino C. mongolicus Pojark. 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m
55°15’37.2172’’ N, Republic Buryatia, Baunt C. neopopovii Czerep. 113°8’57.2040’’ E, 1096 01.VIII.2019 (Bauntovsky District) m
51°38’53.0286’’ N, Republic Buryatia, Kolobki C. tjuliniae Pojark. ex Peschkova 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m
51°41’51.0445’’ N, Republic Buryatia, Zhemchug C. uniflorus Bunge 102°28’14.9261’’ E, 722 17.VII.2019 (Tunkinsky District) m Crataegus dahurica Koehne ex Republic Buryatia, Podlopatki 50°54’50.8598’’ N, 29.V.2018 C.K.Schneid. (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino C. maximowiczii C.K.Schneid. 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m
Foods 2020, 9, 1348 3 of 9
Table S1. Continuation
Collection Species Collection place Coordinates date
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir C. sanguinea Pall. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
Republic Buryatia, Tankhoy 51°32’59.4879’’ N, Dasiphora fruticosa (L.) Rydb. 15.VII.2018 (Kabansky District) 105°7’15.1616’’ E, 504 m
Republic Buryatia, Kyren 51°41’15.4501’’ N, Dryas grandis Juz. 21.VII.2019 (Tunkinsky District) 102°8’21.8127’’ E, 947 m
Republic Buryatia, Kyren 51°41’15.4501’’ N, D. incisa Juz. 21.VII.2019 (Tunkinsky District) 102°8’21.8127’’ E, 947 m
D. integrifolia subsp. crenulata (Juz.) Republic Buryatia, Kyren 51°41’15.4501’’ N, 21.VII.2019 Kozhevn. (Tunkinsky District) 102°8’21.8127’’ E, 947 m
Republic Buryatia, Kyren 51°41’15.4501’’ N, D. oxyodonta Juz. 21.VII.2019 (Tunkinsky District) 102°8’21.8127’’ E, 947 m
55°15’37.2172’’ N, Republic Buryatia, Baunt D. sumneviczii Serg. 113°8’57.2040’’ E, 1096 01.VIII.2019 (Bauntovsky District) m
51°38’53.0286’’ N, Republic Buryatia, Kolobki Dasiphora parvifolia (Fisch.) Juz. 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir Fragaria vesca L. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir F. orientalis Losinsk. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
Republic Buryatia, Onokhoy 51°55’10.1889’’ N, Geum aleppicum Jacq. 03.VII.2019 (Zaigraevsky District) 108°3’26.4983’’ E, 544 m
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino G. rivale L. 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m
Republic Buryatia, Podlopatki 50°54’50.8598’’ N, Malus baccata (L.) Borkh. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
51°51’6.8316’’ N, Republic Buryatia, Zaigrayevo Padus avium Mill. 108°18’36.9388’’ E, 639 11.VI.2019 (Zaigraevsky District) m Republic Buryatia, Tankhoy 51°32’59.4879’’ N, Potentilla acaulis L. 15.VII.2018 (Kabansky District) 105°7’15.1616’’ E, 504 m 55°15’37.2172’’ N, Republic Buryatia, Baunt P. acervata Soják 113°8’57.2040’’ E, 1096 01.VIII.2019 (Bauntovsky District) m Republic Buryatia, Onokhoy 51°55’10.1889’’ N, P. adenotricha Vodop. 03.VII.2019 (Zaigraevsky District) 108°3’26.4983’’ E, 544 m Republic Buryatia, Podlopatki 50°54’50.8598’’ N, P. anserina L. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m Foods 2020, 9, 1348 4 of 9
Table S1. Continuation
Collection Species Collection place Coordinates date
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir P. arenosa (Turcz.) Juz. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino P. argentea L. 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m
50°22’56.5082’’ N, Republic Buryatia, Kyakhta P. asperrima Turcz. 106°26’58.9522’’ E, 853 13.VII.2019 (Kyakhtinsky District) m
Republic Buryatia, Podlopatki 50°54’50.8598’’ N, P. biflora Willd. ex Schltdl. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
Republic Buryatia, Onokhoy 51°55’10.1889’’ N, P. chrysantha Trevir. 03.VII.2019 (Zaigraevsky District) 108°3’26.4983’’ E, 544 m
51°41’51.0445’’ N, Republic Buryatia, Zhemchug P. conferta Bunge 102°28’14.9261’’ E, 722 17.VII.2019 (Tunkinsky District) m
51°51’6.8316’’ N, Republic Buryatia, Zaigrayevo P. crantzii (Crantz) Beck ex Fritsch 108°18’36.9388’’ E, 639 11.VII.2019 (Zaigraevsky District) m 52°2’54.5243’’ N, Republic Buryatia, Kabansk P. desertorum Bunge 106°37’34.5456’’ E, 461 23.VII.2019 (Kabansky District) m
Republic Buryatia, Tankhoy 51°32’59.4879’’ N, P. elegans Cham. & Schltdl. 15.VII.2018 (Kabansky District) 105°7’15.1616’’ E, 504 m 51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir P. evestita Th.Wolf 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
50°22’56.5082’’ N, Republic Buryatia, Kyakhta P. flagellaris Willd. ex Schltdl. 106°26’58.9522’’ E, 853 13.VII.2019 (Kyakhtinsky District) m
51°38’53.0286’’ N, Republic Buryatia, Kolobki P. fragarioides L. 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m
50°22’56.5082’’ N, Republic Buryatia, Kyakhta P. kryloviana Th.Wolf 106°26’58.9522’’ E, 853 13.VII.2019 (Kyakhtinsky District) m
51°51’6.8316’’ N, Republic Buryatia, Zaigrayevo P. leucophylla Pall. 108°18’36.9388’’ E, 639 11.VII.2019 (Zaigraevsky District) m
55°15’37.2172’’ N, Republic Buryatia, Baunt P. longifolia Willd. ex Schltdl. 113°8’57.2040’’ E, 1096 01.VIII.2019 (Bauntovsky District) m
Republic Buryatia, Onokhoy 51°55’10.1889’’ N, P. multifida L. 03.VII.2019 (Zaigraevsky District) 108°3’26.4983’’ E, 544 m
Foods 2020, 9, 1348 5 of 9
Table S1. Continuation
Collection Species Collection place Coordinates date
55°38’56.8229’’ N, Republic Buryatia, P. mujensis Kurbatski 109°20’28.5324’’ E, 582 02.VIII.2019 Severobaykalsk m
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino P. nivea L. 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir P. norvegica L. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
51°41’51.0445’’ N, Republic Buryatia, Zhemchug P. nudicaulis Willd. ex Schltdl. 102°28’14.9261’’ E, 722 17.VII.2019 (Tunkinsky District) m
52°2’54.5243’’ N, Republic Buryatia, Kabansk P. ozjorensis Peschkova 106°37’34.5456’’ E, 461 23.VII.2019 (Kabansky District) m 51°51’6.8316’’ N, Republic Buryatia, Zaigrayevo P. sanguisorba Willd. ex Schltdl. 108°18’36.9388’’ E, 639 11.VII.2019 (Zaigraevsky District) m
55°15’37.2172’’ N, Republic Buryatia, Baunt P. saposhnikovii Kurbatski 113°8’57.2040’’ E, 1096 01.VIII.2019 (Bauntovsky District) m
51°38’53.0286’’ N, Republic Buryatia, Kolobki P. sericea L. 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m
Republic Buryatia, Onokhoy 51°55’10.1889’’ N, P. stipularis L. 03.VII.2019 (Zaigraevsky District) 108°3’26.4983’’ E, 544 m
52°2’54.5243’’ N, Republic Buryatia, Kabansk P. tanacetifolia Willd. ex Schltdl. 106°37’34.5456’’ E, 461 23.VII.2019 (Kabansky District) m
51°38’53.0286’’ N, Republic Buryatia, Kolobki P. tergemina Soják 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m
50°22’56.5082’’ N, Republic Buryatia, Kyakhta P. verticillaris Stephan ex Willd. 106°26’58.9522’’ E, 853 13.VII.2019 (Kyakhtinsky District) m
51°41’51.0445’’ N, Republic Buryatia, Zhemchug Prunus pedunculata (Pall.) Maxim. 102°28’14.9261’’ E, 722 17.VII.2019 (Tunkinsky District) m 51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir Rosa acicularis Lindl. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m 51°51’6.8316’’ N, Republic Buryatia, Zaigrayevo R. davurica Pall. 108°18’36.9388’’ E, 639 11.VII.2019 (Zaigraevsky District) m
Republic Buryatia, Tankhoy 51°32’59.4879’’ N, Rubus arcticus L. 15.VII.2018 (Kabansky District) 105°7’15.1616’’ E, 504 m Foods 2020, 9, 1348 6 of 9
Table S1. Continuation
Collection Species Collection place Coordinates date
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino Rubus chamaemorus L. 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m
Republic Buryatia, Onokhoy 51°55’10.1889’’ N, R. humulifolius C.A. Mey. 03.VII.2019 (Zaigraevsky District) 108°3’26.4983’’ E, 544 m
Republic Buryatia, Tankhoy 51°32’59.4879’’ N, R. matsumuranus H. Lev. & Vaniot 15.VII.2018 (Kabansky District) 105°7’15.1616’’ E, 504 m
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir R. saxatilis L. 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
55°38’56.8229’’ N, Republic Buryatia, Sanguisorba alpina Bunge 109°20’28.5324’’ E, 582 02.VIII.2019 Severobaykalsk m
52°2’54.5243’’ N, Republic Buryatia, Kabansk S. officinalis L. 106°37’34.5456’’ E, 461 23.VII.2019 (Kabansky District) m
51°44’27.2468’’ N, Republic Buryatia, Zun-Murino Sibbaldia adpressa Bunge 102°53’40.4121’’ E, 724 23.VII.2018 (Tunkinsky District) m 50°22’56.5082’’ N, Republic Buryatia, Kyakhta S. procumbens L. 106°26’58.9522’’ E, 853 13.VII.2019 (Kyakhtinsky District) m
51°41’51.0445’’ N, Sibbaldianthe bifurca (L.) Kurtto & Republic Buryatia, Zhemchug 102°28’14.9261’’ E, 722 17.VII.2019 T.Erikss. (Tunkinsky District) m
51°38’53.0286’’ N, S. bifurca subsp. orientalis (Juz.) Kurtto Republic Buryatia, Kolobki 107°23’54.2239’’ E, 506 02.VII.2019 & T.Erikss. (Ivolginsky District) m
Republic Buryatia, Podlopatki 50°54’50.8598’’ N, Sorbaria pallasii (G. Don fil.) Pojark. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
55°38’56.8229’’ N, Republic Buryatia, S. sorbifolia (L.) A. Braun 109°20’28.5324’’ E, 582 02.VIII.2019 Severobaykalsk m
Republic Buryatia, Podlopatki 50°54’50.8598’’ N, Sorbus sibirica Hedl. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
51°41’51.0445’’ N, Republic Buryatia, Zhemchug Spiraea alpina Pall. 102°28’14.9261’’ E, 722 17.VII.2019 (Tunkinsky District) m
55°15’37.2172’’ N, Republic Buryatia, Baunt S. aquilegifolia Pall. 113°8’57.2040’’ E, 1096 01.VIII.2019 (Bauntovsky District) m
Republic Buryatia, Podlopatki 50°54’50.8598’’ N, S. dahurica (Rupr.) Maxim. 29.V.2018 (Mukhorshibirsky District) 107°6’9.5972’’ E, 647 m
51°38’53.0286’’ N, Republic Buryatia, Kolobki S. flexuosa Fisch. ex Cambess. 107°23’54.2239’’ E, 506 02.VII.2019 (Ivolginsky District) m Foods 2020, 9, 1348 7 of 9
Table S1. Continuation
Collection Species Collection place Coordinates date
51°1’54.8212’’ N, Republic Buryatia, Mukhorshibir S. media Schmidt 107°54’10.4700’’ E, 1003 18.VII.2019 (Mukhorshibirsky district) m
52°2’54.5243’’ N, Republic Buryatia, Kabansk S. salicifolia L. 106°37’34.5456’’ E, 461 23.VII.2019 (Kabansky District) m
Foods 2020, 9, 1348 8 of 9
Table S2. Mass spectrometric parameters of compounds 1–60.
ESI-MS, ESI-MS, Collision Parent Daughter Declustering No [M–H]–, MS/MS, energy, Compound ion, m/z ion, m/z potential, V m/z m/z V 1 341 179 341 179 -35 -5 Hexosyl-O-hexose 2 331 169 331 169 -47 -15 1-O-Galloyl-glucose 3 331 169 331 169 -50 -15 O-Galloyl-glucose 4 331 169 331 169 -40 -15 O-Galloyl-glucose 5 331 169 331 169 -45 -15 O-Galloyl-glucose 6 183 139 183 139 -65 -20 2-Pyrone-4,6-dicarboxylic acid 7 783 633, 481, 301 783 301 -72 -15 Pedunculagin 8 353 191, 179, 173, 135 353 191 -30 -10 4-O-Caffeoylquinic acid 9 783 621, 471, 301 783 621 -55 -15 Casuariin 10 577 305, 289 577 289 -85 -30 Procyanidin B1 11 785 623, 473, 301 785 623 -75 -20 Tellimagrandin I1 12 577 305, 289 577 289 -80 -35 Procyanidin B3 13 289 125 289 125 -94 -25 (+)-Catechin 14 353 191, 165 353 191 -30 -10 5-O-Caffeoylquinic acid 15 305 155, 125 305 125 -55 -20 (-)Epigallocatechin 16 577 289 577 289 -80 -30 Procyanidin B2 Ellagic acid-O-methyl 17 447 315, 301 447 315 -105 -35 ester-O-pentoside Tri-O-galloyl-O-hexahydroxy 18 937 775, 625, 475 937 775 -85 -20 diphenoyl-glucose 19 785 623, 473, 301 785 623 -75 -20 Tellimagrandin I2 20 577 305, 289 577 289 -85 -20 Procyanidin dimer Bis-O-hexahydroxydiphenoyl- 21 783 621, 391 783 621 -87 -25 glucose Di-O-galloyl-O-hexahydroxy 22 785 623, 321, 301 785 623 -85 -20 diphenoyl-glucose 23 289 125 289 125 -94 -20 (-)-Epicatechin 24 337 301, 275, 249 337 301 -102 -30 Hexahydroxydiphenic acid Di-O-galloyl-O-hexahydroxy 25 785 623, 321, 301 785 623 -82 -15 diphenoyl-glucose 26 515 353, 191, 179 515 191 -35 -10 1,3-Di-O-caffeoyquinic acid Bis-O-hexahydroxydiphenoyl- 27 783 621, 391 783 621 -75 -25 glucose 28 463 301 463 301 -72 -30 6-Hydroxyluteolin-7-O-Glc Bis-O-hexahydroxydiphenoyl- 29 783 621, 391 783 621 -79 -25 glucose 30 577 289 577 289 -80 -30 Procyanidin dimer 31 937 785, 623, 473, 301 937 785 -87 -20 Tellimagrandin II1 32 935 633, 463, 301 935 633 -80 -20 Potentillin 801, 783, 499, 481, 33 1103 1103 801 -75 -25 Agrimonic acid A 319, 301 1263, 1083, 933, 781, 34 1871 1871 933 -95 -20 Gemin A 301 801, 783, 499, 481, 35 1103 1103 801 -80 -25 Agrimonic acid B 319, 301 1567, 1265, 1085, 36 1869 935, 783, 633, 481, 1869 935 -85 -25 Agrimoniin 301 37 441 291 441 291 -64 -20 (-)-Epicatechin gallate 38 301 285 301 285 -120 -40 Ellagic acid Quercetin-3-O-(6’’-O-rhamnosyl) 39 609 463, 301 609 301 -106 -30 -glucoside 40 937 785, 623, 473, 301 937 785 -85 -25 Tellimagrandin II2 41 463 301 463 301 -100 -30 Quercetin-3-O-glucoside 42 477 301 477 301 -105 -30 Quercetin-3-O-glucuronide 43 447 285 447 285 -110 -35 Luteolin-7-O-glucoside 44 461 285 461 285 -110 -35 Luteolin-7-O-glucuronide Quercetin-3-O-(6’’-O-malonyl)- 45 549 301 549 301 -95 -30 glucoside 46 515 353, 191, 179 515 191 -40 -15 3,5-Di-O-caffeoyquinic acid Kaempferol-3-O-(6’’-O-rhamno- 47 593 447, 285 593 285 syl)-glucoside 48 447 301 447 301 -105 -30 Quercetin-3-O-rhamnoside 49 447 285 447 285 -110 -35 Kaempferol-3-O-glucoside 50 431 269 431 269 -105 -30 Apigenin-7-O-glucoside 51 445 269 445 269 -110 -35 Apigenin-7-O-glucuronide Kaempferol-O-malonyl-O- 52 533 285 533 285 -106 -30 hexoside Foods 2020, 9, 1348 9 of 9
Table S2. Continuation
ESI-MS, ESI-MS, Collision Parent Daughter Declustering No [M–H]–, MS/MS, energy, Compound ion, m/z ion, m/z potential, V m/z m/z V Luteolin-3-O-(6’’-O-malonyl)- 53 533 285 533 285 -115 -30 glucoside 54 431 285 431 285 -115 -35 Kaempferol-3-O-rhamnoside Quercetin-3-O-(6’’-O-p- 55 609 301 609 301 -104 -30 coumaroyl)-glucoside Kaempferol-3-O-(6’’-O-p- 56 593 285 593 285 -110 -30 coumaroyl)-glucoside 57 329 315, 301 329 315 -130 -40 Ellagic acid di-O-methyl ester Luteolin-7-O-(6’’-O-p-coumaroyl) 58 593 285 593 285 -115 -35 -glucoside Apigenin-7-O-(6’’-O-p-malonyl)- 59 517 269 517 269 -120 -35 glucoside Apigenin-7-O-(6’’-O-p- 60 577 269 577 269 -120 -35 coumaroyl)-glucoside