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SUPPLEMENTARY INFORMATION
Bring microbial language to light using imaging mass spectrometry
Chao-Jen Shih,†a Pi-Yu Chen,†a Chih-Chuang Liaw,†b Ying-Mi Lai,a Yu-Liang Yang*a
a
Agricultural Biotechnology Research Center, Academia Sinica, Taipei 115, Taiwan.
b
Department of Marine Biotechnology and Resources, National Sun Yat-sen University,
Kaohsiung 804, Taiwan.
† These authors contributed equally to this work.
Table S1. List of microbial natural products studied by imaging mass spectrometry.
Figure S1 Chemical structures of bacterial natural products studied by IMS.
Figure S2 Chemical structures of natural products of cyanobacteria and Actinomycetes
studied by IMS.
Figure S3 Chemical structures of natural products of Streptomyces and fungi studied by IMS.
Figure S4 Chemical structures of microbial ribosomal peptides studied by IMS.
References
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Table S1. List of microbial natural products studied by imaging mass spectrometry.
Organism
Bacteria
Bacillus amyloliquefaciens
Bacillus subtilis
Natural products
IMS
Ref.
Fengycins
Iturins
TOF-SIMS
TOF-SIMS
MALDI
TOF-SIMS
TOF-SIMS
DESI
MALDI
DESI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
1
1
2
1
3
4
5-8
4
5, 8-10
6, 9, 10
7
7
11
12
12
13
14
14
14
14
14
14
14
14
14
14
11, 14
11, 14
15
15
5, 15
15
15
Surfactins
Surfactins
Plipastatins
Lysobacter enzymogenes
Paenibacillus polymyxa
Pseudomonas aeruginosa
Staphylococcus aureus
Cyanobacteria
Cyanobacterial symbiont in sponge
Lyngbya bouillonii
Lyngbya majuscula 3L
Lyngbya majuscula JHB
Polyglutamatea
SKF
SDP
Subtilosin
Maltophilin
Dihydromaltophilin
LI-F antibiotics
1-Hydroxyphenazine (1-HP)b
1-Methoxyphenazine (1-MP)b
5-N-Methylated PCA (5-MPCA)
Phenazine-1-carboxylic acid (PCA)
Phenazine-1-carboxamide (PCN)
Phenazine-1-sulfateb
Phenazine dimersb
Phenazine pyocyanin (PYO)
Pyochelin
Pyoverdin E
Quinolones
Rhamnolipids
PSMα1 (dPSMα1)
PSMα2
PSMα3
PSMα4 (dPSMα4)
δ-Toxin
13-Demethylisodysidenin
Viridamide B
Curacin A
Jamaicamide A
Jamaicamide B
Yanucamide B
Lyngbya majuscula
Palmyramide A
Nostoc sp. PCC 7120
Pheophytin A
Oscillatoria nigro-viridis
Curacin A
Curazole
Phormidium sp.
Viridamide A
Viridamide B
a
Structures are not completely determined. b Biotransformation products.
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
16
17
16, 18
17
17-19
17
20
12
16, 17
17
17
17
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Table S1. List of microbial natural products studied by imaging mass spectrometry.
(continued)
Organism
Actinomycetes
Actinomycete sp. CNS-575
Amycolatopsis sp. AA4
Beauveria bassiana
beewolf cocoon Streptomycetes
leaf-cutting ant Streptomycetes
Promicromonosporaceae sp. SIO-11
Streptomyces albus
Streptomyces coelicolor
Natural products
IMS
Etamycin
Amychelin
Bassianolide
Beauvericin
Piericidin A1
Piericidin B1
Streptochlorin
Valinomycin
Peptide 2689
Promicroferrioxamines
SAL-2242
Actinorhodin
MALDI
MALDI
MALDI
MALDI
LDI
LDI
LDI
MALDI
MALDI
MALDI
MALDI
TOF-SIMS
DESI
MALDI
MALDI
MALDI
TOF-SIMS
MALDI
TOF-SIMS
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
MALDI
Acyl-desferrioxamines
Calcium dependent antibiotic (CDA)
Streptorubin B
Undecylprodigiosin
Streptomyces griseu
Streptomyces hygroscopicus
Streptomyces roseosporus
Streptomyces sp. Mg1
Streptomyces sviceus
Tistrella mobilis
Fungi
Aspergillus fumigatus
Morphogen SapB
SGR-1832
Stendomycin I-IV
Arylomycin A2
SRO15-2212
SRO15-3108a
Chalcomycin A
SSV-2083
Didemnin B
Dihydrodidemnin B
Didemnin X
Didemnin Y
Nordidemin B
Fusarinine C [Al3+]
Triacetylfusarinine C [Al3+] and [Fe3+]
Mycena metata
6-Hydroxymetatacarboline D
a
Structures are not completely determined.
MALDI
MALDI
MALDI
Ref.
12
21
12
12
22
22
22
23
8
8
24
25
4
11
21
9, 10
25
9
25
9
9
24
24
26
24
24
6
27
27
27
27
27
27
14
14
28
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OH
O
OSO3H
N
N
N
O
OH
N
PCA
NH2
N
5-MPCA
Phenazine dimers
N
O
R1
O
N
1-HP
S
N
N
PCN
R2
N
N
CH3
HO
HO
H2N
O
H
N
O
Pyoverdin E
H
N
N
OH
OH
O
H
N
O
O
O
OH
H
N
OH
NH
O
OH
N
H
HN
O
O
NH
O
O
HN
H
H
N
O
O
HO
Dihydromaltophilin
O
NH
NH
NH
O
R1
LI-F antibiotics
R1 = Val, Ile
R2 = Val, Tyr, Ile, Phe
R3 = Asn, Gln
O
H
N
NH
O
O
OH
NH
O
H2N
O
H
N
R1
OO
OH
H
N
N
H
O
O
NH2
12
NH
N
R2
O
HN
O
O
OH
NH
NH2
O
O
O
NH
OH
Fengycins
H
N
Iturins
O
HO
H
NH
O
NH2
O
R = OH
R3
N
H
NH2
R = acyl chain
R = acyl chain
O
O
O
NH
R=O
Surfactins
OH
O
N
N
H
OH
Maltophilin
N
H
O
O
O
NH2
O
O
HO
HO
R
HN
H
N
O
O
HN
O
NH
O
O
N
H
NH
R
H
N
R
O
O
H
O
O
OH
N
H
O
H2N
OH
O
NH
n
O
N
N
H
n
R = H or rhamnose
n=1, 3, 5, 7
HN
O
O
HO
HN
HN
H2N
Rhamnolipids
OH
N
H
HN
NH
O
O
RO
OH
O
O
OH
O
O
O
HO
pyochelin
H2N
OH
N
1-MP
R1 = H, R2 = H
R1 = OH, R2 = H
R1 = H, R2 = OH
O
OH
N
n
n=3, 6, 8
Quinolones
S
N
R2
OH
N
N
O
N
OH
N
O
N
N
O
N
N
Phenazine-1-sulfate
OH
N
N
N
PYO
O
OH
O
O
R1 = acyl chain, R2 = CH3
Plipastatins
R1 = acyl chain, R2 = CH(CH3)2
Figure S1 Chemical structures of bacterial natural products studied by IMS.
NH
O
OH
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R
O
N
O
N
O
O
O
O
N
H
O
O
H
N
Cl3C
N
O
N
CCl3
NH
N
O
O
O
O
O
S
H
Curacin A
H
N
R=H
O
H
R = CH3,
Viridamides B
N
S
O
Viridamides A
O
O
N
H
N
H
O
O
13-Demethylisodysidenin
Yanucamide B
S
O
N
Curazole
O
N
Cl
O
N
HN
Palmyramide A
O
O
O
O
O
O
O
N
O
N
O
N
O
O
O
NH
O
O
R=H
N
O
N
N
N
H
O
O
O
O
R = Br
Jamaicamide B
O
N
O
O
N
O
HN
H
O
O
Etamycin
Jamaicamide A
O
N
N
H
O
R
N
H
N
O
H
N
H
O
OH
OH
H
O
O
O
O
O
N
N
N
O
O
N
O
O
O
O
O
O
O
O
N
O
Bassianolide
Beauvercin
OH
N
Pheophytin A
O
H
N
N
O
OH
O
NH
O
R1
O
N
H
OH
O
H
N
N
OH
O
Amychelin
Dehydrodidemnin B
R1 = CH3, R2 = O
O
NH
O
OH
O
O
R1 = CH3, R2 = OH
O
N
O
N
H
H
N
Didemnin B
O
N
O
O
OH
O
OH
O
O
Nordidemnin B
N
H
N
R1 = H, R2 = OH
N
O
O
O
Didemnin X
R2
R1 = CH3, n = 3
Didemnin Y
R1 = CH3, n = 4
NH2
R2 =
O
O
N n
H
OH
C7H15
Figure S2 Chemical structures of natural products of cyanobacteria and Actinomycetes
studied by IMS.
O
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Figure S3 Chemical structures of natural products of Streptomyces and fungi studied by IMS.
Electronic Supplementary Material (ESI) for Natural Product Reports
This journal is © The Royal Society of Chemistry 2014
MG I I A G I I K V I K S L I E Q F T G K
MG I I A G I I K F I K G L I E K F T G K
PSM 1
(dPSM 1)
G D
Ala
G
W
T
V Ala D
F
PSM 2
M A I V G T I I K I I K A I I D I F A K
M A Q D I I S T I G D L V KW I
2869
L
Y
A
G
S
V
L G I L V R L Q A I
Ala
Ala
PSM 4
(dPSM 4)
I
T
V A A G Y L Y V V G V N A
I
W
A
SSV-2083
R
Ala
-toxin
Q
Abu
N G
F G
P
F
Ala Ala
S
S
K
V
Ala
G T
Ala
S
Ala
S
I D T V N K F T K K
M S V V D I V S T L L D S L G
S
L
G
S
M E F V A K L F K F F K D L L G K F L G N N PSM 3
S
S
Ala
D
Abu
V F
Cinnamycin
V
A
Dha L
Dha V
A V Y K W V A T T V A A A T Q L
I
L
L
T
K
L
S
Q
I
SDP
Y S S
Ala
Ala
T G Ala
Ala
T P
E Y
S
S
S A W G M Ala I A R
SAL-2242
M
Ala
K
S
A
S
S
S
Dha V
Dha L
I
P
L
A M T
V
V
L
Ala
A L P H
R V
S
V
L
Q
SKF
Ala
Ala S Ala
Ala T P
S
E Y
T G
G A
I
SRO15-2212
A L V
K G A T AlaS
Ala
D
S
S
Ala
N
Ala N
Ala G D Ala
T G Ala
G
G
S
S
P
L
R
S
T
S
W
I
L
T
A
L
L
F
Dha I
Dha L
G F L G T A
E D P
SapB
G
A I
Subtilosin
S
N
A
Dhb
P A V A Q F V I Q G S
Dhb
I
Ala
NH
L V
SGR-1832
Figure S4 Chemical structures of microbial ribosomal peptides studied by IMS. The Ala
marked in blue is represented as cysteine. The amino acids marked in red are originally from
serine (Ala and Dha) and threonine (Abu and Dhb), respectively.
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