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Home , Acrostichum, Acrostichum aureum, Adiantum, Adiantum aleuticum, Adiantum formosum, Adiantum hispidulum

Supplementary Table 1

SAMPLE TISSUE TYPE

CAPN Eusporangiate Monilophytes Equisetales Equisetaceae Equisetum diffusum developing shoots

JVSZ Eusporangiate Monilophytes Equisetales Equisetaceae Equisetum hyemale sterile /branches

NHCM Eusporangiate Monilophytes Marattiales Marattiaceae Angiopteris evecta developing shoots

UXCS Eusporangiate Monilophytes Marattiales Marattiaceae Marattia sp.

BEGM Eusporangiate Monilophytes Ophioglossales 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

PNZO Culcitaceae macrocarpa young leaves

GANB Cyatheales () spinulosa leaves

EWXK Cyatheales Thyrsopteridaceae elegans young leaves

XDVM lobatus young fronds

MEKP Gleicheniales conjugata young leaves

TWFZ Hymenophyllales venosum young fronds

QIAD Hymenophyllales Hymenophyllaceae bivalve young fronds

TRPJ Hymenophyllales Hymenophyllaceae Hymenophyllum cupressiforme young fronds and sori

BIVQ Osmundales Osmundastrum cinnamomeum

YKSS Osmundales Osmundaceae Osmunda regalis leaf

UOMY Osmundales Osmundaceae Osmunda sp.

VIBO Osmundales Osmundaceae Osmunda javanica mature leaves

UWOD Plagiogyriales Plagiogyriaceae japonica young leaves

IXLH hesperium young sterile leaves - B type

GYFU Polypodiales Polypodiaceae young sterile leaves - A type

YLJA Polypodiales Polypodiaceae Polypodium amorphum young sterile leaves

CJNT Polypodiales Polypodiaceae leaf (sterile?)

ZQYU Polypodiales Polypodiaceae pseudoaureum leaf

UJWU Polypodiales Polypodiaceae polypodioides dehydrating fronds

ORJE Polypodiales Polypodiaceae Phymatosorus grossus leaf

OQWW Polypodiales Davalliaceae fejeensis leaf

NWWI Polypodiales exaltata young leaf

JBLI Polypodiales Elaphoglossaceae repanda leaf

FQGQ Polypodiales acrostichoides Mix of sterile and young fertile leaves.

RFRB Polypodiales truncatula young fronds

WGTU Polypodiales Hypodematiaceae immersa just unfurling leaf plus young leaf

PSKY Polypodiales nidus leaf

KJZG Polypodiales Aspleniaceae leaves

OCZL Polypodiales pycnocarpos sterile leaves (maybe a few sporangia)

MROH Polypodiales acuminata young leaf

YJJY Polypodiales Woodsiaceae scopulina young sterile leaves

YQEC Polypodiales Woodsiaceae young leaves

HTFH Polypodiales sensibilis leaves

VITX Polypodiales spicant young leaf

AFPO Polypodiales sp. gametophyte

URCP Polypodiales Athyriaceae Athyrium filix-femina young leaf

FCHS Polypodiales Athyriaceae lobato-crenata fertile leaf

UFJN Polypodiales Athyriaceae wichurae fertile leaf

HNDZ Polypodiales utahensis Mostly sterile leaf tissue; possibly some fertile.

LHLE Polypodiales Cystopteridaceae 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 sterile leaves, slightly older

HEGQ Polypodiales Cystopteridaceae young sterile leaves

MTGC Polypodiales davallioides

WCLG Polypodiales aleuticum young sterile leaves

BMJR Polypodiales Pteridaceae leaf

DCDT Polypodiales Pteridaceae arizonica sterile leaves, some very young

WQML Polypodiales Pteridaceae acrostichoides Mix of sterile and young fertile leaves.

ZXJO Polypodiales Pteridaceae Parahemionitis cordata leaf

POPJ Polypodiales Pteridaceae vittata fronds

FLTD Polypodiales Pteridaceae young leaves

UJTT Polypodiales Pteridaceae trifoliata leaf (perhaps with some developing sporangia)

YCKE Polypodiales Pteridaceae montieliae young leaves, possibly fertile

XDDT Polypodiales Pteridaceae nivea young leaves probably sterile

GSXD Polypodiales Pteridaceae rufa young leaves, possibly fertile

SKYV Polypodiales Pteridaceae lineata leaf, mostly or entirely sterile (hard to tell)

NDUV Polypodiales Pteridaceae Vittaria appalachiana gametophyte

NOKI Polypodiales linearis Young fronds and sori

YIXP Polypodiales Lindsaeaceae Young fronds and sori

CVEG Salviniaceae Azolla cf. caroliniana sterile (leaves)

KIIX Salviniales Marsileaceae Pilularia globulifera young leaves

CQPW Anemiaceae Anemia tomentosa sterile leaf

PBUU Schizaeales Lygodiaceae Lygodium japonicum mix of fertile and sterile leaf tissue

Supplementary Table 2 94 species screened for cyanogenic glycosides

Acrostichum aureum speluncae Adiantum capillus-veneris punctatum Adiantum digitatum Nephrolepis hirsutula Nephrolepis pectinata Adiantum raddianum Nephrolepis rivularis Adiantum raddianum Var. raddianum crassifolium Adiantum seemannii Pallaea viridis drynarioides Aglaomorpha heraclea falcata Amblovenatum oplentum Angiopteris chauliodonta Phlebodium latum Angiopteris evacta Phlebodium macaronesicum Phlebodium scandens Phlebodium subauriculatum Phlebodium subauriculatum 'knightiae' Phlebodium vulgare 'angustifolium' Phymatosorus pustulatus ssp. howensis Blechnum brasiliense Phymatosorus scolopendria Blechnum gibbum bifurcatum Blechnum moorei Blechnum occidentale ssp. minor Platycerium wandae phyllitidis Platycerium willinckii Cyathea cooperi Pleopeltis hirsutissima falcatum Polypodium australe 'rochfordianum' Psilotum nudum Davallia felixmas Davallia Pteris cretica 'albolineata' Davallia trichomanoides Pteris ensiformis Dennstaedtia globulifera Pteris multifida Dennstaedtia producta Pteris quadriauritra antarctica Didymochlaena truncatala caudata adiantiformis Drynaria subauriculatum Selaginella involvens Selaginella kraussiana Hemionitis arifolia Selaginella moellendorffii Huperzia phlegmaria Selaginella pulcherrima Huperzia squarrosa tenuifolia Lygodium japonicum cicutaria Maranta Lev. squamulosa Tectaria incisa Microlepia platyphylla sp Supplementary Figure S1

V L P P V L 0.0 x107 Sara_22_01_80469.d Intens. G3_14_01_19301.d 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