2.1
Evolution of Alkaloids
When were PSM invented during evolution? For our discussion, Fig. 3 illustrates a
molecular phylogeny of plants, which is based on DNA sequences and transcriptome
analyses [56, 57]. From a global perspective, we can state that already the early land
plants needed chemical defense against herbivores and microbes as these organisms
already existed when land plants evolved in the Devonian. Widely present in extant
spore-bearing plants, gymnosperms and angiosperms are terpenoids and polyphenols.
It can be speculated that these PSMs already evolved more than 500 million years ago.
Table 1 (continued)
Target
Natural ligand/
substrate
Alkaloid
Occurrence
GABA receptor
Gamma aminobutyric
acid (GABA)
Bicuculline
Dicentra cucullaria,
Corydalis,
Muscimol
Amanita
Beta-carboline
alkaloids
Peganum,
Banisteriopsis
Adenosine
receptor
Adenosine
Caffeine
Coffea, Camellia, /
lex, Paullinia
Theophylline,
Theobromine
Theobroma
Glycine receptor
Glycine
Brucine
Strychnos
Strychnine
Strychnos
Opioid receptor
Endorphins
Morphine
Papaver somniferum
Acetylcholine
esterase
Acetylcholine
Physostigmine
(eserine)
Physostigma
venenosum
Berberine
Several Papaveraceae
Coptisine
Several Papaveraceae
Galantamine
Several
Amaryllidaceae
Solanine and other
steroid alkaloids
Solanum
Huperzine A
Huperzia serrata
Monoamine
oxidase (MAO)
Noradrenaline,
dopamine, serotonin,
histamine
Harmaline, harmine
Peganum
Salsolinol
Chenopodiaceae
Catechol-Omethyltransferase
Noradrenaline,
adrenaline, dopamine
Tetrahydroisoquinoline Papaveraceae
Na
+ /K
+ channels
Na
+ , K
+
Aconitine
Aconitum
Quinidine
Cinchona
Sparteine, lupanine
Lupinus, Cytisus
Protoveratrine A
Veratrum
8 Evolution of the Angiosperms and Co-evolution of Secondary Metabolites. . .
159