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Supplementary Table 1 Supplementary Table 1 SAMPLE CLADE ORDER FAMILY SPECIES TISSUE TYPE CAPN Eusporangiate Monilophytes Equisetales Equisetaceae Equisetum diffusum developing shoots JVSZ Eusporangiate Monilophytes Equisetales Equisetaceae Equisetum hyemale sterile leaves/branches NHCM Eusporangiate Monilophytes Marattiales Marattiaceae Angiopteris evecta developing shoots UXCS Eusporangiate Monilophytes Marattiales Marattiaceae Marattia sp. leaf BEGM Eusporangiate Monilophytes Ophioglossales Ophioglossaceae Botrypus virginianus Young sterile leaf tissue WTJG Eusporangiate Monilophytes Ophioglossales Ophioglossaceae Ophioglossum petiolatum leaves, stalk, sporangia QHVS Eusporangiate Monilophytes Ophioglossales Ophioglossaceae Ophioglossum vulgatum EEAQ Eusporangiate Monilophytes Ophioglossales Ophioglossaceae Sceptridium dissectum sterile leaf QVMR Eusporangiate Monilophytes Psilotales Psilotaceae Psilotum nudum developing shoots ALVQ Eusporangiate Monilophytes Psilotales Psilotaceae Tmesipteris parva Young fronds PNZO Cyatheales Culcitaceae Culcita macrocarpa young leaves GANB Cyatheales Cyatheaceae Cyathea (Alsophila) spinulosa leaves EWXK Cyatheales Thyrsopteridaceae Thyrsopteris elegans young leaves XDVM Gleicheniales Gleicheniaceae Sticherus lobatus young fronds MEKP Gleicheniales Dipteridaceae Dipteris conjugata young leaves TWFZ Hymenophyllales Hymenophyllaceae Crepidomanes venosum young fronds QIAD Hymenophyllales Hymenophyllaceae Hymenophyllum bivalve young fronds TRPJ Hymenophyllales Hymenophyllaceae Hymenophyllum cupressiforme young fronds and sori BIVQ Osmundales Osmundaceae Osmundastrum cinnamomeum YKSS Osmundales Osmundaceae Osmunda regalis leaf UOMY Osmundales Osmundaceae Osmunda sp. gametophyte VIBO Osmundales Osmundaceae Osmunda javanica mature leaves UWOD Plagiogyriales Plagiogyriaceae Plagiogyria japonica young leaves IXLH Polypodiales Polypodiaceae Polypodium hesperium young sterile leaves - B type GYFU Polypodiales Polypodiaceae Polypodium hesperium young sterile leaves - A type YLJA Polypodiales Polypodiaceae Polypodium amorphum young sterile leaves CJNT Polypodiales Polypodiaceae Polypodium glycyrrhiza leaf (sterile?) ZQYU Polypodiales Polypodiaceae Phlebodium pseudoaureum leaf UJWU Polypodiales Polypodiaceae Pleopeltis polypodioides dehydrating fronds ORJE Polypodiales Polypodiaceae Phymatosorus grossus leaf OQWW Polypodiales Davalliaceae Davallia fejeensis leaf NWWI Polypodiales Lomariopsidaceae Nephrolepis exaltata young leaf JBLI Polypodiales Elaphoglossaceae Bolbitis repanda leaf FQGQ Polypodiales Dryopteridaceae Polystichum acrostichoides Mix of sterile and young fertile leaves. RFRB Polypodiales Hypodematiaceae Didymochlaena truncatula young fronds WGTU Polypodiales Hypodematiaceae Leucostegia immersa just unfurling leaf plus young leaf PSKY Polypodiales Aspleniaceae Asplenium nidus leaf KJZG Polypodiales Aspleniaceae Asplenium platyneuron leaves OCZL Polypodiales Diplaziopsidaceae Homalosorus pycnocarpos sterile leaves (maybe a few sporangia) MROH Polypodiales Thelypteridaceae Thelypteris acuminata young leaf YJJY Polypodiales Woodsiaceae Woodsia scopulina young sterile leaves YQEC Polypodiales Woodsiaceae Woodsia ilvensis young leaves HTFH Polypodiales Onocleaceae Onoclea sensibilis leaves VITX Polypodiales Blechnaceae Blechnum spicant young leaf AFPO Polypodiales Athyriaceae Athyrium sp. gametophyte URCP Polypodiales Athyriaceae Athyrium filix-femina young leaf FCHS Polypodiales Athyriaceae Deparia lobato-crenata fertile leaf UFJN Polypodiales Athyriaceae Diplazium wichurae fertile leaf HNDZ Polypodiales Cystopteridaceae Cystopteris utahensis Mostly sterile leaf tissue; possibly some fertile. LHLE Polypodiales Cystopteridaceae Cystopteris fragilis young leaf+unfurling fiddlehead; appeared sterile XXHP Polypodiales Cystopteridaceae Cystopteris fragilis fronds RICC Polypodiales Cystopteridaceae Cystopteris reevesiana leaf (perhaps with some developing sporangia) YOWV Polypodiales Cystopteridaceae Cystopteris protrusa sterile leaves, slightly older HEGQ Polypodiales Cystopteridaceae Gymnocarpium dryopteris young sterile leaves MTGC Polypodiales Dennstaedtiaceae Dennstaedtia davallioides WCLG Polypodiales Pteridaceae Adiantum aleuticum young sterile leaves BMJR Polypodiales Pteridaceae Adiantum raddianum leaf DCDT Polypodiales Pteridaceae Gaga arizonica sterile leaves, some very young WQML Polypodiales Pteridaceae Cryptogramma acrostichoides Mix of sterile and young fertile leaves. ZXJO Polypodiales Pteridaceae Parahemionitis cordata leaf POPJ Polypodiales Pteridaceae Pteris vittata fronds FLTD Polypodiales Pteridaceae Pteris ensiformis young leaves UJTT Polypodiales Pteridaceae Pityrogramma trifoliata leaf (perhaps with some developing sporangia) YCKE Polypodiales Pteridaceae Notholaena montieliae young leaves, possibly fertile XDDT Polypodiales Pteridaceae Argyrochosma nivea young leaves probably sterile GSXD Polypodiales Pteridaceae Myriopteris rufa young leaves, possibly fertile SKYV Polypodiales Pteridaceae Vittaria lineata leaf, mostly or entirely sterile (hard to tell) NDUV Polypodiales Pteridaceae Vittaria appalachiana gametophyte NOKI Polypodiales Lindsaeaceae Lindsaea linearis Young fronds and sori YIXP Polypodiales Lindsaeaceae Lindsaea microphylla Young fronds and sori CVEG Salviniales Salviniaceae Azolla cf. caroliniana sterile plants (leaves) KIIX Salviniales Marsileaceae Pilularia globulifera young leaves CQPW Schizaeales Anemiaceae Anemia tomentosa sterile leaf PBUU Schizaeales Lygodiaceae Lygodium japonicum mix of fertile and sterile leaf tissue Supplementary Table 2 94 fern species screened for cyanogenic glycosides Acrostichum aureum Microlepia speluncae Adiantum capillus-veneris Microsorum punctatum Adiantum digitatum Nephrolepis cordifolia Adiantum formosum Nephrolepis hirsutula Adiantum hispidulum Nephrolepis pectinata Adiantum raddianum Nephrolepis rivularis Adiantum raddianum Var. raddianum Niphidium crassifolium Adiantum seemannii Pallaea viridis Aglaomorpha drynarioides Pecluma Aglaomorpha heraclea Pellaea falcata Amblovenatum oplentum Phlebodium aureum Angiopteris chauliodonta Phlebodium latum Angiopteris evacta Phlebodium macaronesicum Asplenium bulbiferum Phlebodium scandens Asplenium daucifolium Phlebodium subauriculatum Asplenium marinum Phlebodium subauriculatum 'knightiae' Asplenium nidus Phlebodium vulgare Asplenium scolopendrium 'angustifolium' Phymatosorus pustulatus ssp. howensis Blechnum brasiliense Phymatosorus scolopendria Blechnum gibbum Platycerium bifurcatum Blechnum moorei Platycerium grande Blechnum occidentale Platycerium hillii Blechnum occidentale ssp. minor Platycerium wandae Campyloneurum phyllitidis Platycerium willinckii Cyathea cooperi Pleopeltis hirsutissima Cyrtomium falcatum Polypodium australe Cyrtomium falcatum 'rochfordianum' Psilotum nudum Davallia felixmas Pteridium aquilinum Davallia Pteris cretica Davallia canariensis Pteris cretica 'albolineata' Davallia trichomanoides Pteris ensiformis Dennstaedtia globulifera Pteris multifida Dennstaedtia producta Pteris quadriauritra Dicksonia antarctica Pteris tremula Didymochlaena truncatala Pteris vittata Diplazium esculentum Pyrrosia Doodia caudata Rumohra adiantiformis Drynaria Rumohra adiantiformis Goniophlebium subauriculatum Selaginella involvens Hemionitis Selaginella kraussiana Hemionitis arifolia Selaginella moellendorffii Huperzia phlegmaria Selaginella pulcherrima Huperzia squarrosa Stenochlaena tenuifolia Lygodium japonicum Tectaria cicutaria Maranta Lev. Tectaria gemmifera Microgramma squamulosa Tectaria incisa Microlepia platyphylla Woodwardia sp Supplementary Figure S1 V L P P V L 0.0 x107 Sara_22_01_80469.d Intens. G3_14_01_19301.d Polypodium vulgare x108 Davallia canariensis 1.0 2 0.5 0 0.0 x108 B1_3_01_19290.d x108 Sara_24_01_80471.d Drynaria sp Davalia trichomanoides 3 2 2 1 1 0 x108 D3_7_01_19294.d 0 Microlepia speluncae 6 x10 Polypodium crassofolium Sara_26_01_80473.d 0.75 6 0.50 4 0.25 2 0.00 x108 F2_11_01_19298.d 1.5 Pteris vittata 0 x107 Sara_29_01_80476.d Stenochlae tenofolia 1.0 6 0.5 4 0.0 2 6.4 6.6 6.8 7.0 7.2 7.4 7.6 Time [min] 0 8 x10 Polypodium aureum Sara_35_01_80482.d 2 1 06 x10 Polypodium latum Sara_37_01_80484.d 3 2 1 0 6.4 6.6 6.8 7.0 7.2 7.4 7.6 Time [min] Supplementary Figure S2 TPM Top 50 expressed cytochromes P450 by Phlebodium aureum 400.00 High accumulator of CNG 350.00 Low accumulator of CNG 300.00200.00 250.00 200.00150.00 150.00 100.00 50.00 50.000.00 0.00 Presentation of the 50 highest expressed contigs predicting cytochromes P450 in the high accumulator of cyanogenic glycoside in P. aureum. The contig are ordered according to the expression levels in the low cyanogenic glycoside containing tissue in order to highlight potential candidates. Supplementary Figure S3 CYP79A125 + CYP706C55 x105 1 + CYP71B103 + UGT85A59 0 CYP79A125 + CYP706C55 x105 1 + CYP981F5+ UGT85A59 0 CYP79A125 + CYP981P7 x105 1 + CYP71B103 + UGT85A59 0 CYP79A125 + CYP71B103 + UGT85A59 x105 1 0 CYP79A125 + CYP706C55 + UGT85A59 x105 1 0 CYP79A125 + CYP981P7 x105 1 + CYP981F5 + UGT85A59 0 CYP79A125 + CYP981P7 + UGT85A59 x105 1 0 CYP79A125 + CYP981F5 + UGT85A59 x105 1 0 x105 CYP79A125 + CYP706C55 + CYP981F5 1 0 x105 p19 1 0 x105 Prunasin std. 50 µM 1 0 4.50 5.00 5.50 6.00 Time [min] Supplementary Figure S4 Intens. b x108 a2 Davalia sp EIC m/z 450 1.5 P. aureum EIC m/z 450 a1 1.0 0.5 P. vulgare EIC m/z 450 0.0 6.00 6.25 6.50 6.75 7.00 7.25 7.50 7.75 6 a1,2 x10 +MS2(450.09), 6.9min #723 317.06 + [Glc+pent-H2O+Na] 6 OH + [Glc+pent-H2O+HCN+Na] O 344.09 HO O 4 OH O HO O HO OH C 2 N [M-HCN+Na]+ Vicianin (prunasin-6-arabinose) 332.98 396.90 423.13 0 320 340 360 380 400 420 440 m/z 6 b +MS2(450.12), 6.9min #731 x10 317.05 + 6 [Glc+pent-H2O+Na] O HO O HO OH O 4 HO O HO OH C + [Glc+pent-H2O+HCN+Na] N 344.11 2 Lucumin (prunasin-6-xyloside) + 333.05 [M-HCN+Na] 423.06 0 320 340 360 380 400 420 440 m/z.
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