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1 Supporting Information Figure S1.1 Positive HR-ESI-MS spectrum of compound 1 Figure S1.2 IR spectrum of compound 1 Figure S1.3 1 H NMR (600 MHz, D 2 O) spectrum of compound 1 Figure S1.4 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of compound 1 Figure S C NMR (150 MHz, D 2 O) spectrum of compound 1 Figure S1.6 HMQC (D 2 O) spectrum of compound 1 Figure S1.7 HMBC (D 2 O) spectrum of compound 1 Figure S1.8 Impurity peaks present in compound 1 as detected by HMQC (up) and HMBC spectrum (down) Figure S2.1 Positive HR-ESI-MS spectrum of compound 2 Figure S2.2 Negative HR-ESI-MS spectrum of compound 2 Figure S2.3 1 H NMR (600 MHz, D 2 O) spectrum of compound 2 ( H 2.63 is the signal of DMSO, H 8.35 is the signal of formamide derived from polyamide column chromatography) Figure S C NMR (150 MHz, D 2 O) spectrum of compound 2 ( C 38.7 is the signal of DMSO, C is the signal of formamide derived from polyamide column chromatography) Figure S2.5 HMQC (D 2 O) spectrum of compound 2 Figure S2.6 HMBC (D 2 O) spectrum of compound 2 Figure S2.7 Impurity peaks present in compound 2 as detected by HMQC (up left) and HMBC spectrum (up right and down) Figure S3.1 Positive HR-ESI-MS spectrum of compound 3 Figure S3.2 1 H NMR (600 MHz, D 2 O) spectrum of compound 3 ( H 8.35 is the signal of formamide derived from polyamide column chromatography) Figure S C NMR (150 MHz, D 2 O) spectrum of compound 3 ( C is the signal of formamide derived from polyamide column chromatography) Figure S3.4 HMQC (D 2 O) spectrum of compound 3 Figure S3.5 HMBC (D 2 O) spectrum of compound 3 Figure S3.6 Impurity peaks present in compound 3 as detected by HMBC spectrum Figure S4.1 Positive HR-ESI-MS spectrum of compound 4
2 Figure S4.2 Negative HR-ESI-MS spectrum of compound 4 Figure S4.3 1 H NMR (600 MHz, D 2 O) spectrum of compound 4 Figure S4.4 1 H- 1 HCOSY spectrum of compound 4 Figure S C NMR (150 MHz, D 2 O) spectrum of compound 4 Figure S4.6 DEPT spectrum of compound 4 Figure S4.7 HMQC spectrum of compound 4 Figure S4.8 HMBC spectrum of compound 4 Figure S4.9 Impurity peaks present in compound 4 as detected by HMQC (up) and HMBC spectrum (down) Physiochemical and spectroscopic data of known compounds 6-12.
3 Figure S1.1 Positive HR-ESI-MS spectrum of o compound 1 Figure S1.2 IR spectrum of compound 1
4 Figure S1.3 1 H NMR (600 MHz, D 2 O) spectrum of compound 1 Figure S1.4 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of compound 1
5 Figure S C NMR (150 MHz, D 2 O) spectrum of compound 1 Figure S1.6 HMQC (D 2 O) spectrum of compound 1
6 f1 (ppm) f2 (ppm) Figure S1.7 HMBC (D 2 O) spectrum of compound 1 Figure S1.8 Impurity peaks present in compound 1 as detected by HMQC (up) and HMBC spectrum (down)
7 Figure S2.1 Positive HR-ESI-MS spectrum of compound 2 Figure S2.2 Negative HR-ESI-MS spectrum of compound 2
8 f1 (ppm) Figure S2.3 1 H NMR (600 MHz, D 2 O) spectrum of compound 2 ( H 2.63 is the signal of DMSO, H 8.35 is the signal of formamide derived from polyamide column chromatography) Figure S C NMR (150 MHz, D 2 O) spectrum of compound 2 ( C 38.7 is the signal of DMSO, C is the signal of formamide derived from polyamide column chromatography)
9 f2 (ppm) Figure S2.5 HMQC (D 2 O) spectrum of compound f2 (ppm) Figure S2.6 HMBC (D 2 O) spectrum of compound
10 Figure S2.7 Impurity peaks present in compound 2 as detected by HMQC (up left) and HMBC spectrum (up right and a down) Figure S3.1 Positive HR-ESI-MS spectrum of o compound 3
11 f1 (ppm) Figure S3.2 1 H NMR (600 MHz, D 2 O) spectrum of compound 3 ( H 8.35 is the signal of formamide derived from polyamide column chromatography) f1 (ppm) Figure S C NMR (150 MHz, D 2 O) spectrum of compound 3 ( C is the signal of formamide derived from polyamide column chromatography)
12 f1 (ppm) f2 (ppm) Figure S3.4 HMQC (D 2 O) spectrum of compound f1 (ppm) f2 (ppm) Figure S3.5 HMBC (D 2 O) spectrum of compound 3
13 Figure S3.6 Impurity peaks present in compound 3 as detected by HMBC spectrum Figure S4.1 Positive HR-ESI-MS spectrum of o compound 4 Figure S4.2 Negative HR-ESI-MS spectrum of compound 4
14 Figure S4.3 1 H NMR (600 MHz, D 2 O) spectrum of compound 4 Figure S4.4 1 H- 1 HCOSY spectrum of compound 4
15 Figure S C NMR (150 MHz, D 2 O) spectrum of compound 4 Figure S4.6 DEPT spectrum of compound 4
16 Figure S4.7 HMQC spectrum of compound 4 Figure S4.8 HMBC spectrum of compound 4
17 Figure S4.9 Impurity peaks present in compound 4 as detected by HMQC (up) and HMBC spectrum (down) Physiochemical and spectroscopicc data of known compounds ,7-Dihydroxy-1-methyl-3,4-dihydroisoquinoline (6): yellow powder; HRESIMS: m/z [M+H] + (calcd. for C 10 H 12 NO 2, ); 1 H NMR (600 MHz, DMSO-d 6 ) δ: 7.12 (1H, s, H-8), 6.61 (1H, s, s H-5), 3.58 (2H, t, J 7.8 Hz, H-3), (2H, t, J 7.8 Hz, H-4), 2.47 (3H, s, H-1 ); 13 C NMR (150 MHz, DMSO-d 6 ) δ: (C-1), (C-6), (C-7), (C-9a), (C-10b), (C-8), (C-5), 41.9 (C-3), 25.2 (C-4), 20.3 (C-1 ). 6,7-Dihydroxy-3,4-dihydroisoquinoline (7): yellow powder; HRESIMS: m/z [M+ +H] + (calcd. for C 9 H 10 0NO 2, ); 1 H NMR (6000 MHz, D 2 O) δ: 8.05 (1H, s, H-1), 6.84 (1H, s, H-8), 6.37 ( 1H, s, H-5), 3.55 (2H, t, J 7.8 Hz, H-3), 2.79 (2H, t, J 7.8 Hz, H-4) ; 13 C NMR (150 MHz, D 2 O) δ: (C-1), (C-6), (C-7), (C-9a), (C-10b), (C-8), (C-5), 40.6 (C-3), 24.6 (C-4).
18 (S)-(-)-salsolinol (8): yellow powder; [α] 20 D 32 (c 0.1, MeOH); ESIMS: m/z 180 [M+H] + ; 1 H NMR (600 MHz, D 2 O) δ: 6.67 (1H, s, H-8), 6.64 (1H, s, H-5), 4.42 (1H, q, J 6.6 Hz, H-1), 3.44 (1H, m, H-3a), 3.29 (1H, m, H-3b), 2.92 (1H, m, H-4a), 2.85 (1H, m, H-4b), 1.51 (3H, d, J 6.6 Hz, H-1 ); 13 C NMR (150 MHz, D 2 O) δ: (C-6), (C-7), (C-10b), (C-9a), (C-5), (C-8), 50.8 (C-1), 39.3 (C-3), 24.1 (C-4), 18.6(C-1 ). (R)-(+)-1-isobutyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (9): yellow powder; [α] 20 D +12 (c 0.1, MeOH); positive HRESIMS: m/z [M+H] + (calcd. for C 13 H 20 NO 2, ); negative HRESIMS: m/z [M-H] - (calcd. for C 13 H 18 NO 2, ); 1 H NMR (600 MHz, D 2 O) δ: 6.63 (1H, s, H-8), 6.62 (1H, s, H-5), 4.34 (1H, q, J 6.6 Hz, H-1), 3.43 (1H, m, H-3a), 3.23 (1H, m, H-3b), 2.87 (2H, m, H-4), 1.68 (2H, m, H-1 ), 1.68 (1H, m, H-2 ), 0.92 (3H, d, J 5.4 Hz, H-3 ), 0.90 (3H, d, J 5.4 Hz, H-4 ); 13 C NMR (150 MHz, D 2 O) δ: (C-6), (C-7), (C-10b), (C-9a), (C-5), (C-8), 52.9 (C-1), 38.9 (C-3), 23.9 (C-4), 42.8 (C-1 ), 23.8 (C-2 ), 20.5 (C-3 ), 22.2 (C-4 ). (R)-(+)-1-benzyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (10): yellow powder; [α] 20 D +3 (c 0.1, MeOH); positive HRESIMS: m/z [M+H] + (calcd. for C 16 H 18 NO 2, ); negative HR-ESI-MS: m/z [M-H] - (calcd. for C 16 H 16 NO 2, ), [2M-H] - (calcd. for C 32 H 33 N 2 O 4, ); 1 H NMR (600 MHz, D 2 O) δ: 7.36 (2H, d, J 7.8 Hz, H-3, 5 ), 7.31 (1H, t, J 7.8 Hz, H-4 ), 7.24 (2H, t, J 7.8 Hz, H-2, 6 ), 6.67 (1H, s, H-5), 6.61 (1H, s, H-8), 4.62 (1H, dd, J Hz, J Hz, H-1), 3.43 (1H, m, H-3a), 3.40 (1H, m, H-7 a), 3.21 (1H, m, H-3b), 2.99 (1H, m, H-7 b), 2.93 (1H, m, H-4a), 2.86 (1H, m, H-4b); 13 C NMR (150 MHz, D 2 O) δ: (C-6), (C-7), (C-1 ), (C-2,6 ), (C-3,5 ), (C-4 ), (C-9a), (C-10b), (C-5), (C-8), 56.2 (C-1), 39.3 (C-3), 39.2 (C-7 ), 24.0 (C-4). Dopamine (11): white powder; HRESIMS: m/z [M+H] + (calcd. for C 8 H 12 NO ); 1 H NMR (600 MHz, D 2 O) δ: 6.68 (1H, d, J 7.8 Hz, H-5), 6.61 (1H, d, J 1.8 Hz, H-2), 6.49 (1H, dd, J Hz, J Hz, H-6), 2.95 (2H, t, J 7.8 Hz, H-8), 2.68 (2H, t, J 7.8 Hz, H-7); 13 C NMR (150 MHz, D 2 O) δ: 145.8
19 (C-3), (C-4), (C-1), (C-6), (C-2), (C-5), 40.9 (C-2 ), 33.1 (C-1 ). 2-Sulfonic acid dopamine (12): white powder; positive HRESIMS: m/z [M+H] + (calcd. for C 8 H 12 NO 5 S, ); negative HRESIMS: m/z [M-H] - (calcd. for C 8 H 10 NO 5 S, ), [2M-H] - (calcd. for C 16 H 21 N 2 O 10 S 2, ); 1 H NMR (600 MHz, DMSO-d 6 ) δ: 6.70 (1H, d, J 8.4 Hz, H-5), 6.50 (1H, d, J 8.4 Hz, H-6), 3.15 (2H, t, J 7.2 Hz, H-7), 3.03 (2H, t, J 7.2 Hz, H-8); 13 C NMR (150 MHz, DMSO-d 6 ) δ: (C-1), (C-2), (C-3), (C-4), (C-5), (C-6), 41.2 (C-2 ), 31.3 (C-1 ).
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