3.2
Intraspecies Variation
PA profiles also vary within species. The famous example for the intraspecies PA
variation is the presence of chemotypes of J. vulgaris and J. erucifolius. According
to the evaluation of PAs of more than 100 J. vulgaris populations in Europe, it was
found that there were two different chemotypes present: “jacobine chemotype”
dominated by jacobine and its derivatives as major PAs and “erucifoline
chemotypes” dominated by erucifoline-like PAs [38]. Except these two chemotypes,
later on, “senecionine chemotype” (with senecionine-like PAs as dominating PAs)
R 2
HO
O
O
O O H
N
CH 3
R 1 = CH 3 , R 2 = H Senecionine
R 1 = H, R 2 = CH 3 Integerrimine
R 3 = CH 3 , R 4 = H Retrorsine
R 3 = H, R 4 = CH 3 Usaramine
R 5 = H, R 6 = CH 3 , R 7 = H Spartioidine
R 5 = CH 3 , R 6 = H, R 7 = H Seneciphylline
Riddelliine
R 5 = CH 3 , R 6 = H, R 7 = Ac Acetylseneciphylline
R 1
CH 3
R 4
HO
O
O
O O H
N
CH 3
R 3
OH
Senecionine-like PAs
Jacobine-like PAs
Otosenine-like PAs
Jacobine
Erucifoline-like PAs
R 8 = OH Jacoline
R 8 = Cl Jaconine
R 9 = H Erucifoline
Senkirkine
R 9 = Ac Acetylerucifoline
R 10 = H Otosenine
R 10 = Ac Florosenine
R 11 = OH, R 12 = H Onetine
R 11 = OH, R 12 = Ac Floridanine
R 11 = Cl, R 12 = H Desacetyldoronine
R 11 = Cl, R 12 = Ac Doronine
Jacozine
Dehydrojaconine
R 6
R 7 O
O
O
O O H
N
CH 2
CH 3
R 5
HO
O
O
O O H
N
CH 2
OH
H 3 C
HO
HO
O
O
O
O
O H
N
CH 3
H 3 C
CH 3
O
H 3 C
OH
O
O
O O H
N
CH 3
R 8
CH 3
HO
O
O
O O H
N
CH 2
CH 3
H 3 C
HO
H 3 C
OH
O
O
O O H
N
CH 2
Cl
CH 3
O
HO
O
O
O O H
N
R 9 O
H 3 C
CH 3
O
O
O
O O O
N
CH 3
CH 3
H 3 C
CH 3
R 10 O
R 12 O
O
O
O O
N
CH 3
CH 3
H 3 C
H 3 C
OH
O
O
O O
N
CH 3
R 11
CH 3
O
O
CH 3
CH 3
Fig. 1 Structures of the pyrrolizidine alkaloid (PAs) found in shoots and roots of Jacobaea
aquatica, Jacobaea vulgaris, and F 1 and F 2 hybrids between these two species
11 Variation in Leaf-Surface and Leaf-Tissue Secondary Metabolites:. . .
253