Supplementary Material Chemotaxonomic Study of Bostrychia spp. (Ceramiales, Rhodophyta) Based on Their Mycosporine-like Amino Acid Content Maria Orfanoudaki 1, Anja Hartmann 1,*, Mitsunobu Kamiya 2, John West 3 and Markus Ganzera 1 1 Institute of Pharmacy, Pharmacognosy, University of Innsbruck, Innrain 80-82, Innsbruck 6020, Austria; [email protected] (M.O.); [email protected] (M.G.) 2 Department of Ocean Sciences, School of Marine Resources and Environment, Tokyo University of Marine Science and Technology, Japan 4-5-7 Konan, Minato-ku, Tokyo 108-8477, Japan; [email protected] (M. K.) 3 School of BioSciences, University of Melbourne, Parkville, 3010 Victoria, Australia; [email protected] (J. W.) * Correspondence: [email protected] (A.H.); Tel.: +43 512 507-58430 Contents Figure S1 UV and Mass spectrum of compound the unidentified MAA at 7.6 min .................... 2 Figure S2 UV and Mass spectrum of compound the unidentified MAA at 9.9 min .................... 2 Figure S3 UV and Mass spectrum of compound the unidentified MAA at 8.0 min .................... 3 Figure S4 UV and Mass spectrum of compound the unidentified MAA at 21.2 min .................. 4 Table S1. Quantitative HPLC-DAD results for compounds 1-12 in the B. simpliciuscula/B. kingii and the B. moritziana/B. radicans complex ........................................................................................... 5 Table S2. Quantitative HPLC-DAD results for compounds 1-12 in Bostrychia spp. ................... 10 Table S3. Overview of the investigated samples of Bostrychia spp., their collection sites and dates. ...................................................................................................................................................... 16 Figure S1. UV and mass spectrum of compound the unidentified MAA at 7.6 min Figure S2. UV and mass spectrum of compound the unidentified MAA at 9.9 min 2 Figure S3. UV and mass spectrum of compound the unidentified MAA at 8.0 min 3 Figure S4. UV and mass spectrum of compound the unidentified MAA at 21.2 min 4 Table S1. Quantitative HPLC-DAD results for compounds 1-12 in the B. simpliciuscula/B. kingii and the B. moritziana/B. radicans complex.; all values expressed as mg per g of dry material, assignment of compounds and species is the same as Table 2, assignment of generation, sex and developmental stage: B, Bisexual; F, Female; M, Male; T, Tetrasporophyte; G, Gametophyte; S, Sporelings; V, Vegetative, assignment of sample origin: H, Herbarium; C, Culture. Sample SHI (1) AST (3) POR (4) APA* (5) PT (6) MG (7) Unknown MAA Lineage [1,2] Developmental stage Sample origin B sim C 3306 T 0.058 1.358 1.570 B sim/kin 1 Tetrasporophyte Culture B sim C 3321 T 0.191 0.686 0.783 B sim/kin 1 Tetrasporophyte Culture B sim C 3677 T 0.196 0.940 0.379 B sim/kin 1 Tetrasporophyte Culture B sim C 3322 F 0.139 0.907 0.473 B sim/kin 1 Female Culture B sim C 3305 0.190 2.182 0.974 B sim/kin 1 Culture B sim C 3671 T 0.132 0.691 0.406 B sim/kin 1 Tetrasporophyte Culture B sim C 3663 MF 0.328 0.302 B sim/kin 1 Male, Female Culture B sim C 3663 G 0.144 1.439 0.233 B sim/kin 1 Gametophyte Culture B sim C 3663 F 0.101 1.628 0.651 B sim/kin 1 Female Culture B sim C 3663 T 0.060 0.519 0.31 B sim/kin 1 Tetrasporophyte Culture B sim C 3581 T 0.142 0.641 0.472 B sim/kin 1 Tetrasporophyte Culture B sim C 3581 S 0.321 1.989 0.563 B sim/kin 1 Sporelings Culture B sim C 3581 F 0.076 0.835 0.517 B sim/kin 1 Female Culture B sim C 3304 T 0.148 0.879 0.467 B sim/kin 1 Tetrasporophyte Culture B sim C 3108 T 0.085 0.429 0.291 B sim/kin 1 Tetrasporophyte Culture B sim C 3108 M 0.126 1.126 0.338 B sim/kin 1 Male Culture B sim C 3108 F 0.320 0.892 0.222 B sim/kin 1 Female Culture B sim C 3658 T 0.085 0.522 0.413 B sim/kin 1 Tetrasporophyte Culture B sim C 3658 G 0.129 1.746 0.438 B sim/kin 1 Gametophyte Culture B sim C 3658 F 0.160 1.493 0.382 B sim/kin 1 Female Culture 5 Table S1. Cont. B sim C 3576 0.176 0.492 0.428 B sim/kin 1 Culture B sim C 3319 T 0.257 1.494 0.72 B sim/kin 1 Tetrasporophyte Culture B sim C 2915 G 0.079 0.310 0.196 B sim/kin 1 Gametophyte Culture B sim C 2915 T 0.094 0.665 0.787 B sim/kin 1 Tetrasporophyte Culture B sim C 2915 S 0.201 0.527 0.233 B sim/kin 1 Sporelings Culture B sim C 2747 0.240 1.408 0.656 B sim/kin 1 Culture B sim C 3315 T 0.120 0.713 0.955 B sim/kin 1 Tetrasporophyte Culture B sim C 3672 0.158 0.676 0.484 B sim/kin 1 Culture B sim C 3657 T 0.033 0.506 0.512 B sim/kin 1 Tetrasporophyte Culture B sim C 3612 T 0.170 1.638 0.264 B sim/kin 1 Tetrasporophyte Culture B sim C 3612 B 0.191 1.256 0.668 B sim/kin 1 Bisexual Culture B sim C 3612 F 0.126 0.801 0.516 B sim/kin 1 Female Culture B sim C 3317 T 0.276 1.202 0.881 B sim/kin 1 Tetrasporophyte Culture B sim C 4046 0.270 0.447 0.659 B sim/kin 1 Culture B sim C 2933 0.124 0.987 1.120 B sim/kin 1 Culture B kin C 4203 F At 8.0 and 21.5 min B sim/kin 2 Female Culture B kin C 3545 At 8.0 and 21.5 min B sim/kin 2 Culture B kin C 3109 F At 8.0 and 21.5 min B sim/kin 2 Female Culture B kin C 3110 F At 8.0 and 21.5 min B sim/kin 2 Female Culture B kin C 3111 F At 8.0 and 21.5 min B sim/kin 2 Female Culture B kin C 3114 F At 8.0 min B sim/kin 2 Female Culture B kin C 3114 T At 8.0 min B sim/kin 2 Tetrasporophyte Culture Male, B kin C 3114 MT At 8.0 min B sim/kin 2 Culture Tetrasporophyte 6 Table S1. Cont. Tetrasporophyte, B kin C 3308 TF At 8.0 min B sim/kin 2 Culture Female B kin C 3308 F At 8.0 min B sim/kin 2 Female Culture B sim C 2964 M 0.347 1.914 B sim/kin 3 Male Culture B sim C 3211 T 0.536 0.24 B sim/kin 3 Tetrasporophyte Culture B sim C 2963 B 0.316 1.879 B sim/kin 3 Bisexual Culture B sim C 2963 T 0.597 2.051 B sim/kin 3 Tetrasporophyte Culture B sim C 3992 0.044 7.711 1.927 B sim/kin 3 Culture B sim C 3546 0.099 6.627 1.857 B sim/kin 3 Culture B sim H Oo 0.013 1.287 B sim/kin 4 Herbarium B sim H Ka 0.033 2.797 B sim/kin 4 Herbarium Sample SHI (1) AST (3) POR (4) APA* (5) PT (6) MG (7) Unknown MAA Lineage [3–7] B rad C 3029 F 2.415 Present B rad/mor 5 Female Culture B rad C 3038 T 2.781 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3034 F 0.898 Present B rad/mor 5 Female Culture B rad C 3061 MF 2.114 Present B rad/mor 6 Male, Female Culture B rad C 2928 F 1.368 Present B rad/mor 6 Female Culture B rad C 3129 MF 1.900 Present B rad/mor 5 Male, Female Culture B rad C 3136 T 2.165 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3124 MF 2.011 Present B rad/mor 5 Male, Female Culture B rad C 2649 2.731 Present B rad/mor 6 Culture B rad C 2636 0.793 Present Culture B rad C 3030 F 1.632 Present B rad/mor 5 Female Culture B rad C 3128 F 0.193 Present B rad/mor 5 Female Culture 7 Table S1. Cont. B rad C 3171 T 0.913 Present B rad/mor 5 Culture B rad C 3137 1.446 Present Culture B rad C 3044 M 0.211 Present Male Culture B rad C 3195 T 3.082 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3115 T 0.030 2.503 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3037 T 0.151 2.446 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3026 MF 0.337 2.858 Present B rad/mor 5 Male, Female Culture B rad C 3062 T 0.213 3.590 Present Tetrasporophyte Culture B rad C 3035 F 0.040 2.287 Present B rad/mor 5 Female Culture B rad C 3051 T 0.084 2.827 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3058 MF 0.027 1.933 Present Male, Female Culture B rad C 3144 MF 0.040 1.670 Present Male, Female Culture B rad C 3125 MF 0.042 0.172 4.319 Present Male, Female Culture B rad C 3094 F 0.156 0.200 3.406 B rad/mor 6 Female Culture B rad C 3203 V 0.346 0.310 4.396 Present Vegetative Culture B rad C 3142 T 0.029 0.558 4.476 Present B rad/mor 5 Tetrasporophyte Culture B rad C 3126 F 0.031 0.033 0.100 4.857 Present Female Culture B rad C 3140 M 0.130 0.305 5.831 Present Male Culture B rad C 3019 F 0.044 0.162 6.080 Present B rad/mor 5 Female Culture Sample SHI (1) AST (3) POR (4) APA* (5) PT (6) MG (7) Unknown MAA Lineage [3–8] B mor C 4170 3.330 B rad/mor 1 Culture B mor C 4169 1.846 B rad/mor 1 Culture B mor C 4168 1.422 B rad/mor 1 Culture B mor C 4167 0.826 B rad/mor 1 Culture 8 Table S1.