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10 Neurotransmitters, Neuroregulators and Neurotoxins in Plants 141<br />

a b<br />

Fig.10.3. Effect of the melatonin synthesis inhibitor p-chlorophenylalanine on morphogenesis<br />

in St. John’s wort: a control explant, b explant cultured on medium supplemented with<br />

p-chlorophenylalanine. Quantification of indoleamines in St. John’s wort tissues exposed to<br />

p-chlorophenylalanine demonstrated the complete inhibition of melatonin synthesis and<br />

elevated concentrations of serotonin<br />

H<br />

N<br />

C<br />

H 2<br />

C<br />

OH<br />

Indole-3-acetic acid<br />

O<br />

H 3C<br />

O<br />

H<br />

N<br />

NH 2<br />

C CH C<br />

H2 tryptophan<br />

H<br />

N<br />

H<br />

N<br />

C<br />

H 2<br />

melatonin<br />

C<br />

H 2<br />

tryptamine<br />

H 2<br />

C<br />

H<br />

N<br />

C<br />

O<br />

CH 3<br />

OH<br />

O<br />

H 2<br />

C NH 2<br />

HO<br />

HO<br />

HO<br />

H<br />

N<br />

NH 2<br />

C CH C<br />

H2 5-hydroxytryptophan<br />

H<br />

N<br />

C<br />

H 2<br />

H 2<br />

C<br />

H<br />

N<br />

N-acetylserotonin<br />

H<br />

N<br />

C<br />

H 2<br />

serotonin<br />

C<br />

OH<br />

O<br />

O<br />

H 2<br />

C NH 2<br />

Fig.10.4. Radiolabel from 14 C-tryptophan was recovered as 14 C-indoleacetic acid, 14 Ctryptamine,<br />

14 C-serotonin and 14 C-melatonin. (Adapted from Murch et al. 2000, 2002)<br />

attenuate auxin-generated growth. A high ratio of auxin to cytokinin will<br />

encourage the regeneration of long, thin tissues such as adventitious roots,<br />

whereas a low auxin-to-cytokinin ratio ensures the regeneration of the<br />

thicker, more isodiametric tissue forms that are associated with shoots.<br />

CH 3

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