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Type of the Paper 1 Supplementary Materials: 2 Dereplication by High-Performance Liquid 3 Chromatography (HPLC) with Quadrupole-Time-of- 4 Flight Mass Spectroscopy (qTOF-MS) and Antiviral 5 Activities of Phlorotannins from Ecklonia cava 6 Hyo Moon Cho 1,†, Thi Phuong Doan 1,†, Thi Kim Quy Ha 1, Hyun Woo Kim 1, Ba Wool 7 Lee 1, Ha Thanh Tung Pham 1, Tae Oh Cho 2 and Won Keun Oh 1,* 8 1 Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of 9 Pharmacy, Seoul National University, Seoul 08826, Korea; [email protected] (H.M.C.); 10 [email protected] (T.P.D.); [email protected] (T.K.Q.H.); [email protected] (H.W.K.); 11 [email protected] (B.W.L.); [email protected] (H.T.T.P.) 12 2 Marine Bio Research Center, Department of Life Science, Chosun University, Gwangju 501-759, 13 Korea; [email protected] 14 * Correspondence: [email protected]; Tel.: +82-02-880-7872 15 † These authors contributed equally. 16 2 of 33 17 Contents 18 Figure S1. HRESIMS spectrum of compound 1 ............... Error! Bookmark not defined. 19 Figure S2. IR spectrum of compound 1. ............................................................................. 5 1 20 Figure S3. H NMR spectrum of compound 1 (800 MHz, DMSO-d6) ............................... 6 13 21 Figure S4. C NMR spectrum of compound 1 (200 MHz, DMSO-d6)Error! Bookmark 22 not defined. 23 Figure S5. HSQC spectrum of compound 1 (800 MHz, DMSO-d6)Error! Bookmark not 24 defined. 25 Figure S6. HMBC spectrum of compound 1 (800 MHz, DMSO-d6) ............................... 10 26 Figure S7. ROESY spectrum of compound 1 (800 MHz, DMSO-d6)Error! Bookmark 27 not defined. 28 Figure S8. HRESIMS spectrum of compound 2 ............................................................... 11 29 Figure S9. IR spectrum of compound 2. ........................................................................... 12 1 30 Figure S10. H NMR spectrum of compound 2 (850 MHz, DMSO-d6) ........................... 13 13 31 Figure S11. C NMR spectrum of compound 2 (212.5 MHz, DMSO-d6) ....................... 14 32 Figure S12. HSQC spectrum of compound 2 (850 MHz, DMSO-d6) .............................. 15 33 Figure S13. HMBC spectrum of compound 2 (850 MHz, DMSO-d6) ............................. 16 34 Figure S14. ROESY spectrum of compound 2 (850 MHz, DMSO-d6) ............................ 17 3 of 33 35 Figure S15. Relationships between ion masses (m/z value) in negative ion mode and RMD 36 values for compounds detected by HPLC-qTOFMS in the EC70 fraction ....................... 18 37 Figure S16. HPLC-qTOFMS measurement for twelve isolated compounds in negative ion 38 mode at collision energy of 50 eV ..................................................................................... 19 39 Figure S17. MS/MS spectra and fragment ions analysis of isolated compounds. HPLC- 40 qTOFMS spectroscopic data of these single compounds were measured in negative mode 41 at collision energy of 50 eV………………………………………………………………20 42 Figure S18. Effects of compound 11, 12, 13, and 14 on the viral protein synthesis at a 43 concentration of 20 µM; original uncropped blots ............................................................ 21 44 Figure S19. Inhibitory effects of compound 12 on the viral proteins synthesis in a 45 concentration-dependent manner; original uncropped blots ......................................... 22-23 46 Figure S20. (A) Key HMBC correlations of compounds 1 and 2. (B) Key ROESY 47 correlations on 3D structure of compounds 1 and 2……………………………………….24 48 Figure S21. Physicochemical properties of isolated known compounds from E. cava.25-28 49 Table S1. List of species in Ecklonia genus from website World Register of Marine Species 50 (http://www.marinespecies.org) ..................................................................................................................... 29 51 Table S2. The inhibitory effects of compounds 11, 12, 13, and 14 against the H1N1 52 A/PR/8/34 virus in a cytopathic effect and cytotoxicity assays ...................................................... 30 1 13 53 Table S3. H and C NMR spectroscopic data of compounds 1 and 2 in DMSO-d6 (δ in 54 ppm) ……………………………………………………………………………………...31 55 Scheme S1. Extraction and fractionation procedure of E. cava…………………………..32 56 4 of 33 57 Figure S1. HRESIMS spectrum of compound 1. 58 5 of 33 59 Figure S2. IR spectrum of compound 1. 60 61 62 6 of 33 1 63 Figure S3. H NMR spectrum of compound 1 (800 MHz, DMSO-d6). 64 65 7 of 33 13 66 Figure S4. C NMR spectrum of compound 1 (200 MHz, DMSO-d6). 67 68 8 of 33 69 Figure S5. HSQC spectrum of compound 1 (800 MHz, DMSO-d6). 70 9 of 33 71 Figure S6. HMBC spectrum of compound 1 (800 MHz, DMSO-d6). 72 73 74 10 of 33 75 Figure S7. ROESY spectrum of compound 1 (800 MHz, DMSO-d6). 76 11 of 33 77 Figure S8. HRESIMS spectrum of compound 2. 78 12 of 33 79 Figure S9. IR spectrum of compound 2. 80 81 13 of 33 1 82 Figure S10. H NMR spectrum of compound 2 (850 MHz, DMSO-d6). 83 14 of 33 13 84 Figure S11. C NMR spectrum of compound 2 (212.5 MHz, DMSO-d6). 85 15 of 33 86 Figure S12. HSQC spectrum of compound 2 (850 MHz, DMSO-d6). 87 16 of 33 88 Figure S13. HMBC spectrum of compound 2 (850 MHz, DMSO-d6). 89 17 of 33 90 Figure S14. ROESY spectrum of compound 2 (850 MHz, DMSO-d6). 91 18 of 33 92 Figure S15. Relationships between ion masses (m/z value) in negative ion mode and RMD values for compounds detected by HPLC-qTOFMS in 93 the EC70 fraction. 94 95 19 of 33 96 Figure S16. HPLC-qTOFMS measurement of twelve isolated compounds in negative ion 97 mode at collision energy of 50 eV. 98 99 20 of 33 100 Figure S17. MS/MS spectra and fragment ions analysis of isolated compounds. HPLC- 101 qTOFMS spectroscopic data of these single compounds were measured in negative mode 102 at collision energy of 50 eV. 103 104 21 of 33 105 Figure S18. Effects of compound 11, 12, 13, and 14 on the viral protein synthesis at a 106 concentration of 20 µM; original uncropped blots. 107 The viral-infected cells were exposed to compounds 11, 12, 13, and 14 (20 µM) and 108 ribavirin (20 µM) as a positive control. After 1 day of incubation, the cell lysates were 109 collected and target proteins were measured using Western blotting method. Equal amounts 110 of proteins were loaded on SDS-polyacrylamide gels. After transferred to PVDF 111 membranes, they were firstly incubated with neuraminidase antibody overnight. For 112 removing bound primary and secondary antibodies, the membranes were incubated with a 113 RestoreTM Western blot stripping buffer (Thermo Sci.) and they were then detected the β- 114 actin protein using a LAS4000 luminescent image analyzer. Sample names were from 1-7 115 as follows: uninfected ctrl, viral-infected (vi) ctrl, vi + ribavirin (20 µM), vi + 11, 12, 13, 116 and 14 (20 µM), respectively. Data were included in the final analysis in Figure 4A. 117 22 of 33 118 Figure S179. Inhibitory effects of compound 12 on the viral proteins synthesis in a 119 concentration-dependent manner; original uncropped blots. 120 The procedure of Western blot experiment was successfully carried as above described in 121 Figure S18. The membranes were firstly detected neuraminidase or hemagglutinin proteins. 122 Using a stripping buffer (Thermo Sci.) for removing bound primary and secondary 123 antibodies, the membranes were then incubated with β-actin antibody. (A) Sample names 124 were from 1-7 as follows: uninfected ctrl, viral-infected (vi) ctrl, vi + ribavirin (20 µM), vi 125 + 12 (5, 10, 20, and 40 µM), respectively. (B) Sample names were from 1-6 as follows: 126 uninfected ctrl, vi ctrl, vi + ribavirin (20 µM), vi + 12 (5, 10, and 20 µM), respectively. (C) 127 Sample names were from 1-12 as follows: uninfected ctrl-1; vi ctrl-1; vi + ribavirin (20 128 µM)-1, -2; vi + 12 (10 µM)-1, -2; vi + 12 (20 µM)-1, -2; vi + 12 (40 µM)-1, -2; vi ctrl-2; 129 uninfected ctrl-2; respectively. Figure 4B was included in the final analysis. 130 131 23 of 33 132 133 134 135 . 136 24 of 33 137 Figure S20. (A) Key HMBC correlations of compounds 1 and 2. (B) Key ROESY 138 correlations on 3D structure of compounds 1 and 2. 139 140 141 142 143 25 of 33 144 Figure S21. Physicochemical properties of isolated known compounds from E. cava. 145 146 Eckol (6) 147 Brown powder; UV (MeOH) λmax nm (log ε) 210 (2.70), 235 (2.75); ESI-MS m/z 371 [M − - 1 148 H] ; H NMR (DMSO-d6, 300 MHz): δ 6.16 (1H, s, H-3), 5.97 (1H, d, J = 2.4 Hz, H-8), 149 5.80 (1H, d, J = 2.4 Hz, H-6), 5.79 (1H, t, J = 2.4 Hz, H-4'), 5.71 (2H, d, J = 2.1 Hz, H-2', 13 150 H-6'); C NMR ( DMSO-d6, 75 MHz): δ 160.3 (C-1'), 158.8 (C-3', C-5'), 153.0 (C-7), 146.1 151 (C-9), 146.0 (C-2), 142.5 (C-5a), 141.9 (C-4), 137.1 (C-10a), 123.1 (C-1), 122.5 (C-9a), 152 122.0 (C-4a), 98.4 (C-8), 98.1 (C-3), 96.2 (C-4'), 93.7 (C-6), 93.6 (C-2', C-6'). 153 154 7-Phloroeckol (7) 155 Brown powder; UV (MeOH) λmax nm (log ε) 210 (2.34), 230 (2.27); ESI-MS m/z 495 [M − - 1 156 H] ; H NMR (DMSO-d6, 300 MHz): δ 6.14 (s, H-3), 6.00 (1H, d, J = 2.9, H-8), 5.77 (1H, 157 d, J = 2.9, H-6), 5.80 (1H, d, J = 1.9 Hz, H-4'), 5.86 (1H, d, J = 2.4 Hz, H-2', H-6'); 13C 158 NMR (DMSO-d6, 75 MHz): δ 122.2 (C-1), 146.0 (C-2), 98.4 (C-3), 141.9 (C-4), 123.2 (C- 159 4a), 142.9 (C-5a), 93.4 (C-6), 154.6 (C-7), 98.1 (C-8), 146.1 (C-9), 124.0 (C-9a), 137.1 (C- 160 10a), 160.3 (C-1'), 93.6 (C-2'), 159.0 (C-3'), 96.3 (C-4'), 159.0 (C-5'), 93.7 (C-6'), 122.9 (C- 161 1''), 151.3 (C-2''), 94.9 (C-3''), 154.9 (C-4''), 94.9 (C-5''), 151.3 (C-6'') 162 163 6,6’-Bieckol (10) 164 Brown powder; UV (MeOH) λmax nm (log ε) 210 (2.34), 230 (2.27); ESI-MS m/z 743 [M + + - 1 165 H] , 741 [M − H] ; H NMR (DMSO-d6, 300 MHz): δ 6.09 (s, H-3), 6.04 (1H, s, H-8), 5.80 13 166 (1H, d, J = 1.8 Hz, H-4'), 5.74 (1H, d, J = 2.1 Hz, H-2', H-6'); C NMR (DMSO-d6, 75 167 MHz): δ 160.5 (C-1'), 158.9 (C-3', C-5), 151.3 (C-7), 145.4 (C-2), 144.5 (C-9), 141.9 (C- 26 of 33 168 4), 141.4 (C-5a), 137.2.
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