Anabaenopsis abijatae AB2002/09 (AM773296) Nostoc carneum IAM M-35 (AB325906) Calothrix brevissima IAM M-249 (AB074504)

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1 57 Nostoc sphaeroides HBHF0604 (EU178144) Gloeotrichia echinulata PYH6 (AM230703) Nostoc punctiforme ATCC (CP001037) Nostoc linckia IAM M-30 (AB325907) 93 Nostoc muscorum I (AJ630451) Trichormus variabilis KCTC AG10180 (DQ234832) Cylindrospermum stagnale PCC 7417 (AJ133163) Anabaenopsis abijatae AB2002/09 (AM773296) Nostoc carneum IAM M-35 (AB325906) Calothrix brevissima IAM M-249 (AB074504) Anabaenopsis circularis NIES21 (AF247595) FACHB-245 Anabaena variabilis ATCC (CP000117) Anabaena anomala RPAN34 (GQ4664) Anabaena ballyganglii RPAN35 (GQ466496) Anabaena laxa RPAN14 (GQ466510) Anabaena aphanizomenoides RPAN68 (GQ466515) Anabaena sphaerica RPAN12 (GQ466513) Nodularia baltica BY1 (AJ133177) Nodularia harveyana Bo53 (AJ781143) Aphanizomenon ovalisporum FAS-AP1 (EU076457) 80 Halotia wernerae CENA158 T (KC695852) Halotia longispora CENA184 T (KC695875) Trichormus variabilis KCTC AG10180 (DQ234832) Gloeotrichia echinulata PYH6 (AM230703) 62 Nostoc calcicola TH2S22 (AM711529) Nostoc ellipsosporum V (AJ630450) Nostoc muscorum I (AJ630451) Nostoc linckia IAM M-30 (AB325907) FACHB-252 Nostoc entophytum IAM M-267 (AB093490) Cylindrospermum stagnale PCC 7417 (AJ133163) 96 Anabaenopsis circularis NIES21 (AF247595) Anabaena variabilis ATCC (CP000117) Anabaena anomala RPAN34 (GQ4664) Anabaena sphaerica RPAN12 (GQ466513) Anabaena laxa RPAN14 (GQ466510) Anabaena ballyganglii RPAN35 (GQ466496)

2 72 96 Cyanobium gracile PCC6307 (AF001477) Aphanothece minutissima 2LT34S03 (FM177488) Merismopedia tenuissima 0BB46S01 (AJ639891) 88 Synechococcus rubescens SAG 3.81 (AF317076) Prochlorococcus marinus subsp. marinus CCMP 1375 T (AE017126) Prochlorococcus marinus subsp. pastoris MED4 (BX548174) Prochlorococcus marinus subsp. pastoris PCC 9511 T (AF180967) Synechococcus spongiarum SH4 (JENA00091) Synechococcus elongatus simbu1 (JN ) Synechococcus elongatus ARKK1 (JN8126.1) Synechococcus elongatus RBD03 (KT ) Synechococcus elongatus CENA126 (KP ) 62 Synechococcus elongatus PCC 6301 (KM0181.1) 82 FACHB-1092 Synechococcus elongatus PCC 7942 (CP000) Leptolyngbya nodulosa UTEX 2910 (EF122600) Oscillatoria neglecta M-82 (AB003168) Loriellopsis cavernicola LF-B5 T (HM748318) 79 Aphanocapsa muscicola VP3-03 (FR798916) Synechococcus lividus C1 (AF132772) 60 Phormidium pristleyi ANT.LH61.2 (AY493582) Arthronema africanum SAG (AB115966) Neosynechococcus sphagnicola CAUP A 1101 (JJML00087) Leptolyngbya frigida ANT.LH64B.1 (AY493577)

3 Nodularia spumigena AV63 (AJ781138) Nodularia baltica BY1 (AJ133177) Nodularia harveyana Bo53 (AJ781143) 84 Nodularia sphaerocarpa Fae19 (AJ781144) Anabaenopsis nadsonii 2LT27S11 (FM177481) Anabaenopsis elenkinii AB2002/34 (AM ) Anabaenopsis elenkinii AB2006/20 (AM ) Halotia longispora CENA184 T (KC695875) Halotia branconii CENA392 T (KJ843313) Halotia wernerae CENA158 T (KC695852) 82 Nostoc calcicola TH2S22 (AM711529) Nostoc ellipsosporum V (AJ630450) Nostoc muscorum I (AJ630451) Nostoc linckia IAM M-30 (AB325907) Anabaena crassa 215 (AJ293112) Anabaena planctonica 1tu33s8 (AJ630432) 70 Anabaena macrospora PMC9301 (AJ293115) 92 Anabaena spiroides PMC9702 (AJ293118) 59 Anabaena smithii 1tu39s8 (AJ630436) Anabaena sigmoidea 0tu36s7 (AJ630434) 60 Aphanizomenon flos-aquae 1tu26s2 (AJ ) Aphanizomenon flos-aquae 1tu29s19 (AJ ) Aphanizomenon flos-aquae PMC9401 (AJ293126) Aphanizomenon flos-aquae PMC9707 (AJ ) Aphanizomenon gracile PMC9402 (AJ ) FACHB FIG S1 Neighbour-joining tree based on 16S rrna gene sequences, showing the phylogenetic relationships between strains FACHB-245, FACHB-252, FACHB-1092 and FACHB-1171 and closest genera of cyanobacteria such as Anabaena, Nostoc, Synechococcus and Aphanizomenon. Bootstrap values (expressed as percentages of 0 replications) >50% are given at nodes. Bar, 0.5%, 0.5%, 1% and 0.5% sequence divergences respectively

4 S. cinnamoneus NBRC12852 T (AB184850) 76 S. pseudoechinosporeusnbrc12518 T (AB184) 60 S. hiroshimensis NBRC 3839 T (AB184802) S. blastmyceticus NRRL B-5480 T (AY9802) 84 S. ardus NBRC T (AB184864) S. abikoensis NBRC T (AB184537) S. olivoverticillatus NBRC T (AB184636) JXJ S. eurocidicus NRRL B-1676 T (AY9790) S. stramineus NBRC T (AB184720) S. netropsis NBRC 3723 T (AB184792) S. mobaraensis NBRC T (AORZ00256) S. sporoclivatus NBRC 767 T (AB2434) S. rhizosphaericus NBRC 778 T (AB2441) 90 S. atrirubernrrl B T (EU812169) S. seoulensis NBRC T (AB2470) S. spongiae Sp080513SC-24 T (AB498741) S. niveiscabiei S78 T (AF361786) S. fragilisnrrl 2424 T (AY17) 85 S. chiangmaiensis TA4-1 T (AB562507) FIG S2 Neighbour-joining tree based on 16S rrna gene sequences, showing the phylogenetic relationships between strain JXJ-0089 and related and representative species of genus Streptomyces. Bootstrap values (expressed as percentages of 0 replications) >50% are given at nodes. Bar, 0.5% sequence divergence. 19

5 20 a

6 21 b

7 22 c

8 d 23 24

9 25 e

10 26 f

11 27 g

12 28 h

13 29 i

14 j FIG S3 Spectra data of 1 D and 2D NMR of tryptamine and tryptoline. a, 1 H NMR of tryptamine; b, 13 C NMR of tryptamine; c, COSY of tryptamine; d, HSQC of tryptamine; e, HMBC of tryptamine; f, 1 H NMR of tryptoline, g, 13 C NMR of tryptoline; h, COSY of tryptoline; i, HSQC of tryptoline; j, HMBC of tryptoline

15 FIG S4 Algicidal activities of tryptoline, tryptamine, tryptophan, gramine and copper sulfate on Microcystis sp. FACHB-905 lawn (1, 6, 11, 16 represent tryptoline of 5, 10, 15 and 20 µg/disk respectively; 2, 7, 12 and 17 represent tryptamine of 5, 10, 15 and 20 µg/disk respectively; 3, 8, 13 and 18 represent tryptophan of 5, 10, 15 and 20 µg/disk respectively; 4, 9, 14 and 19 represent gramine of 5, 10, 15 and 20 µg/disk respectively; 5, 10, 15 and 20 represent copper sulfate of 5, 10, 15 and 20 µg/disk respectively.)

16 FIG S5 Damages of tryptamine and tryptoline to the morphology of Anabaena sp. FACHB-245 and Nostoc sp. FACHB-252 (observed by using the oil immersionlens of optical microscope, Olympus BX43, 10 times, NA=1.25). a and d, cells of Anabaena sp. FACHB-245 and Nostoc sp. FACHB-252 damaged by tryptamine; b and e, cells of Anabaena sp. FACHB-245 and Nostoc sp. FACHB-252 damaged by tryptoline; c and f, cells of Anabaena sp. FACHB-245 and Nostoc sp. FACHB-252 of the controls. Cell chains of Anabaena sp. Cell chains of Anabaena sp. FACHB-245 separated each other, and the background was the glass slide; cell chains of Nostoc sp. FACHB-252 aggregated, and the background was not glass, but other cell chains or fragment of lysed cells etc.

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