Supporting Information

Table S1.NMR data for metabolites in Pseudomonas sp. HF-1.

Peak / Metabolites / Assignment / δ1 H
(multiplicitya) / δ13 C / Assigned with
1 / -keto-isocaproate / CH2 / 2.62 / 50.9 / TOCSY, HMBC
CH / 2.11 / #b / COSY, TOCSY
CH3 / 0.94(d, 6.6Hz) / 24.9 / JRE, COSY, TOCSY, HSQC, HMBC
2 / Leucine / CH / 3.75 / 43.0 / JRE, TOCSY, HMBC
CH2CH / 1.73 / 26.8 / JRE, COSY, TOCSY, HMBC
CH3 / 0.97(d) / 24.5 / JRE, COSY, TOCSY, HSQC
’CH3 / 0.96(d) / 24.5
3 / Valine / CH / 3.63 / 63.7 / TOCSY, HMBC
CH / 2.28 / 31.6 / COSY, TOCSY, HSQC, HMBC
CH3 / 1.04(d, 6.9Hz) / 21.2 / JRE, COSY, TOCSY, HSQC
’CH3 / 0.99(d, 6.9Hz) / 19.6
4 / 2-propanol / CH3 / 1.18(d) / 26.8 / JRE, COSY, HSQC, HMBC
CH / 4.03 / 67.8 / COSY, HMBC
5 / Ethanol / CH2 / 1.19(t) / 19.4 / JRE, COSY, TOCSY, HSQC, HMBC
CH3 / 3.67 / 60.5 / COSY, TOCSY, HMBC
6 / Diethyl ether / CH2 / 3.21(q) / 49.7 / JRE, COSY, TOCSY, HSQC, HMBC
CH3 / 1.29(t) / 11.3
7 / Lactate / CH / 4.13 / 71.8 / COSY, TOCSY, HMBC
CH3 / 1.34(d) / 22.7 / JRE, COSY, TOCSY, HSQC
COOH / 185.4 / HMBC
8 / Alanine / CH / 3.79 / 53.5 / COSY, TOCSY, HSQC, HMBC
CH3 / 1.49(d, 7.0Hz) / 19.0 / JRE, COSY, TOCSY, HSQC, HMBC
COOH / 178.6 / HMBC
9 / Putrescine / CH2 / 1.77 / 26.9 / COSY, TOCSY, HSQC, HMBC
CH2 / 3.07 / 42.0 / COSY, TOCSY, HSQC
10 / U1 / 1.82(dd) / 19.9 / JRE, COSY, HSQC
2.51 / # / COSY
11 / Acetate / CH3 / 1.93(s) / 26.3 / JRE, HSQC
COOH / 184.3 / HMBC
12 / Acetamide / CH3 / 2.01(s) / 24.7 / JRE, HSQC
CO / 180.1 / HMBC
13 / Acetone / CH3 / 2.21(s) / 23.7 / JRE, HSQC
CO / 176.2 / HMBC
14 / Glutarate / ,CH2 / 2.3(t) / 36.6 / JRE, TOCSY, HSQC
CH2 / 1.92 / # / TOCSY
COOH / 184.2 / HMBC
15 / Glutamate / CH / 3.78 / 57.7 / JRE, COSY, TOCSY, HSQC, HMBC
CH2 / 2.06(m), 2.13(m) / 29.6
CH2 / 2.36(dt) / 36.4
COOH / 184.2 / HMBC
16 / Pyruvate / CH3 / 2.38(s) / 29.4 / JRE, HSQC
C=O / 207.8 / HMBC
17 / Succinate / CH2 / 2.41(s) / 37.0 / JRE, HSQC
18 / -ketoglutarate / CH2 / 2.45(t, 6.7Hz) / 33.7 / JRE, COSY, TOCSY, HSQC, HMBC
CH2 / 3.01(t, 7.3Hz) / 38.1
C=O / 208.1 / HMBC
C5OOH / 184.2
19 / -alanine / CH2 / 2.56(t) / 36.1 / JRE, COSY, TOCSY, HSQC, HMBC
CH2 / 3.19(t) / 40.5
COOH / 181.2 / HMBC
20 / Methylamine / CH3 / 2.61(s) / 27.7 / JRE, HSQC
21 / U2 / 2.94(s) / 16.8 / JRE, HSQC, HMBC
121.9 / HMBC
22 / Ethanolamine / CH2NH2 / 3.15(d) / 44.4 / JRE, COSY, TOCSY, HSQC, HMBC
CH2OH / 3.83 / 60.5
23 / Betaine / CH2 / 3.91(s) / 69.1 / JRE, HMBC
CH3 / 3.27(s) / 56.2 / JRE, HSQC, HMBC
24 / Methanol / CH3 / 3.36(s) / 51.9 / JRE, HSQC
25 / Glycine / CH2 / 3.57(s) / 44.5 / JRE, HSQC
COOH / 175.2 / HMBC
26 / U3 / 4.11(d) / # / JRE
27 / -glucose / C1H / 4.66(d, 8.0Hz) / 98.8 / JRE, COSY, TOCSY, HSQC, HMBC
C2H / 3.26 / 77.2 / COSY, TOCSY, HSQC, HMBC
C3H / 3.49 / 78.9
28 / -glucose / C1H / 5.24(d, 3.8Hz) / 94.9 / JRE, COSY, TOCSY, HSQC
C2H / 3.54 / 73.0 / COSY, TOCSY, HSQC, HMBC
C3H / 3.71 / 75.0 / TOCSY, HSQC, HMBC
C4H / 3.44 / 72.8
C5H / 3.84 / 74.5
C6H / 3.74 / 63.8
29 / Trehalose / C1H / 5.2(d, 3.8Hz) / 96.1 / JRE, COSY, TOCSY, HSQC
C2H / 3.67 / # / COSY, TOCSY, HMBC
C3H / 3.86 / # / TOCSY
C4H / 3.48 / # / TOCSY, HMBC
30 / Maltose / C3H / 3.98 / # / TOCSY
C4H / 3.66 / 79.2 / TOCSY, HSQC, HMBC
C7H / 5.41(d) / 102.4 / JRE, TOCSY, HSQC, HMBC
31 / Ribose-5-phosphate / C1H / 5.62 / 100.2 / COSY, TOCSY, HSQC
C2H / 4.11 / # / COSY, TOCSY
C3H / 4.06 / # / TOCSY
C4H / 4.22 / #
32 / Uracil / C4H / 7.54(d) / 146.1 / COSY, TOCSY, HSQC
C5H / 5.81(d) / 103.6
33 / Cytidine / C2 / 159.8 / HMBC
C3 / 169.6
C4H / 7.68(d, 7.5Hz) / 146.5 / JRE, COSY, TOCSY, HSQC, HMBC
C5H / 6.03(d, 7.5Hz) / 99.0 / JRE, COSY, TOCSY, HSQC
C1’H / 5.85 / 97.1 / COSY, TOCSY, HSQC, HMBC
C2’H / # / 76.7 / HMBC
C4’H / # / 83.8 / HMBC
34 / 5’-UMP / C3 / 154.0 / HMBC
C4 / 169.2
C5H / 5.88(d, 8.1Hz) / 104.9 / JRE, COSY, TOCSY, HSQC, HMBC
C6H / 7.74(d, 8.1Hz) / 146.5
C1’H / 5.92 / 95.6
35 / 5’-CMP / C2 / 160.4 / HMBC
C4H / 7.85(d, 7.5Hz) / 144.2 / JRE, COSY, TOCSY, HSQC
C5H / 6.06(d) / 99.2
C6 / 169.0 / HMBC
36 / Uridine / C2 / 155.5 / HMBC
C4H / 7.88(d) / 144.7
C5H / 5.91(d) / 105.2 / JRE, COSY, TOCSY, HSQC
C1’H / 5.91 / 92.1 / HSQC
C2’H / 4.32 / 76.8 / COSY, HMBC
C3’H / 4.21 / # / TOCSY
37 / Guanine 2’,3’-cyclic
phosphate / C4 / 151.4 / HMBC
C5 / 121.6
C8H / 8.34(s) / 143.5 / HSQC, HMBC
C1’H / 6.30(d) / 92.3 / COSY, TOCSY, HSQC
C2’H / 5.47 / 83.4 / COSY, TOCSY
C3’H / 5.18 / 83.6 / HSQC, HMBC
C4’H / 4.51 / 88.2 / HSQC, HMBC
C5’H / 3.92 / 76.2 / HMBC
38 / Adenosine / C8H / # / 143.3 / HMBC
C4 / 151.6
C1’H / 6.07(d) / 91.2 / JRE, TOCSY, HSQC
C2’H / # / 76.7 / HMBC
C3’H / 4.45 / 73.6 / TOCSY, HSQC
39 / Adenosine 2’,3’-cyclic
phosphate / C2H / 8.25(s) / 155.4 / HSQC
C4 / 154.1
C5 / 119.1 / HMBC
C6 / 158.8
C8H / 7.97(s) / 141.5 / HSQC, HMBC
C1’H / 6.15(d, 6.1Hz) / 91.7 / JRE, COSY, TOCSY, HSQC
C2’H / 5.43 / 83.4 / COSY, TOCSY, HSQC, HMBC
C3’H / 5.16 / 80.5 / COSY, TOCSY, HSQC
C4’H / 4.43 / 88.7 / COSY, TOCSY, HMBC
C5’H / 3.91 / 63.8 / TOCSY, HMBC
40 / Pyridine / C1H, C5H / 8.53(d) / 151.5 / JRE, COSY, TOCSY, HSQC, HMBC
C2H, C4H / 7.48(m) / 127.3
C3H / 7.91(td) / 140.6
41 / Pyrimidine / C2H / 9.15(d) / 160.0 / JRE, TOCSY, HSQC, HMBC
C4H, C6H / 8.82(d, 5.1Hz) / 159.8 / JRE, COSY, TOCSY, HSQC, HMBC
C5H / 7.62(td) / 125.2
42 / Formate / CH / 8.46(s) / 172.6 / JRE, HSQC
43 / Cholesterol / CH3 / 0.74(s) / 21.5 / JRE, HSQC
0.84(s) / 21.6
0.87(s) / 23.8

aMultiplicity: s, singlet; d, doublet; t, triplet; q, quartet; dd, doublet of doublets; dt, doublet of triples; m, multiplet. U: unidentified signal. b The signals or multiplicities were not determined.

Fig. S1. Curves of nicotine biodegradation and growth of Pseudomonas sp. strain HF-1 (30 ºC, pH7.5, 150 rpm). Nicotine treatment concentration (dotted line): 1 g/L (circle), 2 g/L (triangle) and 3 g/L (square); OD value (solid line) of control strains (circle), 1 g/L (triangle), 2 g/L (square) and 3 g/L (diamond) nicotine-treated strains.

Fig. S2. Permutations testing plots (a), (b) and (c) related to models (a), (b) and (c) in figure 3, respectively. A total of 200 permutations were performed and the resulting R2 (green triangle) and Q2 (blue square) values were plotted. The regression line for R2 and Q2 was represented with green line and blue line, respectively.