Page 806 - Veterinary Toxicology, Basic and Clinical Principles, 3rd Edition

Cyanobacterial (Blue-Green Algae) Toxins Chapter | 57 765

VetBooks.ir H COOH R 2 7 O Adda COOH 4 CH 3 Mdhb
6
3
D–Glu
5
17
HN N NH 15 20 (DMAdda) H 3 C O 1 N N CH 3
O CH H R 1 14 16 OR 2 H O
C 2 2
H 3 H 3 C
O 13 4
H H H H S O O 11 10 9 8 6 5 3 NH R O
5 OCH 3 S 12 7 1
S H NH
S H NH H R 1 H CH 3 CH 3 O N
C H CH Z X 19 18 Z
H 3 H N
3 O COOH
S 2
4 2
O H COOH D-MeAsp
D-Asp
3
1
Microcystins Nodularins
CH 3
O 10
OH
H H + 9
O NH
O SO 2
3
1 2
N NH HN NH
Me + 8 3
6 5
H NH O
7
4
Cylindrospermopsin Anatoxin-a
4 6 CH CH CH 3
2
5 3 O 10 11
HN 3 N + 9
1 NH
2 N CH 3 2
+ O 1 2
8
NH 2 3
+ CH 5
P O 3 6
O
7
O 4
Anatoxin-a(s) Homoanatoxin-a
O
17
R 16
4
H
H N
6 7
R 1 N 5 +
1 +
8 NH 2
2 4 9 15
13 + 3 N
H N + N H
2
12 OH
14
10
11 R 5
R 3
R 2
PSPs
FIGURE 57.1 Structural formulas of cyanobacterial toxins.
More than 100 different structural variants of micro- involves an amino acid called ADDA (3-amino-9-meth-
cystins have been identified from various genera of cya- oxy-2,6,8-trimethyl-10-phenyldeca; 4,6-dienoic acid) and
nobacteria (Luukkainen et al., 1994; Lawton et al., 1995; six other amino acids, including two variable positions
Welker and von Do ¨hren, 2006). The shared structure that designate the congener. The most extensively studied,