Supporting Information s2
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SUPPORTING INFORMATION
Mooreamide: A Cannabinomimetic Lipid from the Marine Cyanobacterium
Moorea bouillonii
Emily Mevers, Teatulohi Matainaho, Marco Allara’, Vincenzo Di Marzo and William H.
Gerwick
NMR Spectroscopic Data and Biological Data for Mooreamide (1)
1 Figure S1 H NMR (500 MHz, CDCl3) spectrum of mooreamide (1)
13 Figure S2 C NMR (125 MHz, CDCl3) spectrum of mooreamide (1)
1 Figure S3 HSQC ( H 500 MHz, CDCl3) spectrum of mooreamide (1)
1 Figure S4 HMBC ( H 600 MHz, CDCl3) spectrum of mooreamide (1)
1 Figure S5 COSY ( H 500 MHz, CDCl3) spectrum of mooreamide (1)
1 Figure S6 NOESY ( H 600 MHz, CDCl3) spectrum of mooreamide (1) Figure S7 Displacement of [3H]-CP 55,940 by mooreamide (1) 1 Figure S1: H NMR (500 MHz, CDCl3) spectrum of mooreamide (1)
1782H-2_3-A-5-G STANDARD PROTON PARAMETERS 1100
1000
900
800
700
600
500
400
300
200
100
0
-100
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 f1 (ppm) 13 Figure S2: C NMR (125 MHz, CDCl3) spectrum of mooreamide (1) 9 5 5 0 0 2 6 0 1 6 6 1 9 1 0 5 9 1 6 8 9 1 4 4 4 3 8 2 7 6 0 3 8 4
1782H-2_3-A-5-G_CDCl3_vx500MHz 1 ...... 13 9 1 8 7 8 0 0 4 8 7 5 5 0 7 5 9 6 2 0 9 6 4 1 4 ...... 6 4 3 3 3 3 2 2 2 2 1 3 2 9 3 2 2 1 9 8 8 8 6 Std carbon 0 1 1 1 1 1 1 1 1 1 1 1 6 5 3 3 3 3 3 2 2 2 2 1 -
12
11
10
9
8
7
6
5
4
3
2
1
0
-1
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 f1 (ppm) 1 Figure S3: HSQC ( H 500 MHz, CDCl3) spectrum of mooreamide (1)
1782H-2_3-A-5-G_gHSQC STANDARD PROTON PARAMETERS 10
20
30
40
50
60
70 ) m p p ( 80 1 f
90
100
110
120
130
140
150 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 f2 (ppm) 1 Figure S4: HMBC ( H 600 MHz, CDCl3) spectrum of mooreamide (1)
1782H2/2 HMBC (hmbcgplpndqf) 10 Cryoprobe 062708 20
30
40
50
60
70
80 ) m p p (
90 1 f 100
110
120
130
140
150
160
170
6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 f2 (ppm) 1 Figure S5: COSY ( H 500 MHz, CDCl3) spectrum of mooreamide (1)
1782H-23-A-56-gCOSY STANDARD PROTON PARAMETERS 0.5
1.0
1.5
2.0
2.5
3.0 ) m p
3.5 p (
1 f 4.0
4.5
5.0
5.5
6.0
6.5
6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 f2 (ppm) 1 Figure S6: NOESY ( H 600 MHz, CDCl3) spectrum of mooreamide (1)
1782H2/5 0.5 NOESY (noesyph) Cryoprobe 062708 1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 f2 (ppm) Figure S7: Displacement of [3H]-CP 55,940 by mooreamide (1).
g 100 n f i o d t n i n
b 75 e
0 m 4 e 9 c , a 5 50 l 5 p s P i d C
- 25 ] % H 3 [ 0 -10 -8 -6 -4 log[M]