5. Wink M (2009) Introduction: functions of plant secondary metabolites and their exploitation in
biotechnology. Annu Plant Rev 39:1–20
6. De Luca V, St Pierre B (2000) The cell and developmental biology of alkaloid biosynthesis.
Trends Plant Sci 5:168–173
7. Wink M (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64:3–19
8. Kliebenstein DJ, Kroymann J, Brown P, Figuth A, Pedersen D, Gershenzon J, Mitchell-Olds T
(2001) Genetic control of natural variation in Arabidopsis glucosinolate accumulation. Plant
Physiol 126:811–825
9. Sheludko Y, Gerasimenko I, Kolshorn H, Stockigt J (2002) Isolation and structure elucidation of
a new indole alkaloid from Rauvolfia serpentina hairy root culture: the first naturally occurring
alkaloid of the raumacline group. Planta Med 68:435–439
10. Cheng D, Kirk H, Mulder PPJ, Vrieling K, Klinkhamer PGL (2011) Pyrrolizidine alkaloid
variation in shoots and roots of segregating hybrids between Jacobaea vulgaris and Jacobaea
aquatica. New Phytol. https://doi.org/10.1111/j.1469-8137.2011.03841.x
11. Macel M, Vrieling K, Klinkhamer PGL (2004) Variation in pyrrolizidine alkaloid patterns of
Senecio jacobaea. Phytochemistry 65:865–873
12. van Dam NM, Vrieling K (1994) Genetic-variation in constitutive and inducible pyrrolizidine
alkaloid levels in Cynoglossum officinale L. Oecologia 99:374–378
13. Vrieling K, de vos H, van wijk CAM (1993) Genetic analysis of the concentrations of
pyrrolizidine alkaloids in Senecio jacobaea. Phytochemistry 32:1141–1144
14. Arany AM, de Jong TJ, Kim HK, van Dam NM, Choi YH, van Mil HGJ, Verpoorte R,
van der Meijden E (2009) Genotype-environment interactions affect flower and fruit herbivory
and plant chemistry of Arabidopsis thaliana in a transplant experiment. Ecol Res 24:1161–1171
15. Kirk H, Vrieling K, Van Der Meijden E, Klinkhamer PGL (2010) Species by environment
interactions affect pyrrolizidine alkaloid expression in Senecio jacobaea, Senecio aquaticus,
and their hybrids. J Chem Ecol 36:378–387
16. Lankau RA, Kliebenstein DJ (2009) Competition, herbivory and genetics interact to determine
the accumulation and fitness consequences of a defence metabolite. J Ecol 97:78–88
17. LoPresti EF (2015) Chemicals on plant surfaces as a heretofore unrecognized, but ecologically
informative, class for investigations into plant defence. Biol Rev Camb Philos Soc. https://doi.
org/10.1111/brv.12212
18. Müller C, Riederer M (2005) Plant surface properties in chemical ecology. J Chem Ecol
31:2621–2651
19. Hopkins RJ, van dam NM, van Loon JJ (2009) Role of glucosinolates in insect-plant
relationships and multitrophic interactions. Annu Rev Entomol 54:57–83
20. Badenes-Pérez FR, Reichelt M, Gershenzon J, Heckel DG (2011) Phylloplane location of
glucosinolates in Barbarea spp. (Brassicaceae) and misleading assessment of host suitability
by a specialist herbivore. New Phytol 189:549–556
21. Shroff R, Schramm K, Jeschke V, Nemes P, Vertes A, Gershenzon J, Svatos A (2015)
Quantification of plant surface metabolites by matrix-assisted laser desorption-ionization
mass spectrometry imaging: glucosinolates on Arabidopsis thaliana leaves. Plant J 81:961–972
22. Hartmann T (1999) Chemical ecology of pyrrolizidine alkaloids. Planta 207:483–495
23. Chou MW, Fu PP (2006) Formation of DHP-derived DNA adducts in vivo from dietary
supplements and Chinese herbal plant extracts containing carcinogenic pyrrolizidine alkaloids.
Toxicol Ind Health 22:321–327
24. Langel D, Ober D, Pelser PB (2011) The evolution of pyrrolizidine alkaloid biosynthesis and
diversity in the Senecioneae. Phytochem Rev 10:3–74
25. Joosten L, Cheng D, Mulder PPJ, Vrieling K, van-Veen JA, Klinkhamer PGL (2011)
The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea
vulgaris. Phytochemistry 72:214–222
26. Rizk AM (1991) Naturally occurring pyrrolizidine alkaloids. CRC Press, Boca Raton, p 240
27. Wiedenfeld H, Roeder E, Bourauel T, Edgar J (2008) Pyrrolizidine alkaloids: structure and
toxicity. V&R unipress GmbH, Bonn
260
D. Cheng
biotechnology. Annu Plant Rev 39:1–20
6. De Luca V, St Pierre B (2000) The cell and developmental biology of alkaloid biosynthesis.
Trends Plant Sci 5:168–173
7. Wink M (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64:3–19
8. Kliebenstein DJ, Kroymann J, Brown P, Figuth A, Pedersen D, Gershenzon J, Mitchell-Olds T
(2001) Genetic control of natural variation in Arabidopsis glucosinolate accumulation. Plant
Physiol 126:811–825
9. Sheludko Y, Gerasimenko I, Kolshorn H, Stockigt J (2002) Isolation and structure elucidation of
a new indole alkaloid from Rauvolfia serpentina hairy root culture: the first naturally occurring
alkaloid of the raumacline group. Planta Med 68:435–439
10. Cheng D, Kirk H, Mulder PPJ, Vrieling K, Klinkhamer PGL (2011) Pyrrolizidine alkaloid
variation in shoots and roots of segregating hybrids between Jacobaea vulgaris and Jacobaea
aquatica. New Phytol. https://doi.org/10.1111/j.1469-8137.2011.03841.x
11. Macel M, Vrieling K, Klinkhamer PGL (2004) Variation in pyrrolizidine alkaloid patterns of
Senecio jacobaea. Phytochemistry 65:865–873
12. van Dam NM, Vrieling K (1994) Genetic-variation in constitutive and inducible pyrrolizidine
alkaloid levels in Cynoglossum officinale L. Oecologia 99:374–378
13. Vrieling K, de vos H, van wijk CAM (1993) Genetic analysis of the concentrations of
pyrrolizidine alkaloids in Senecio jacobaea. Phytochemistry 32:1141–1144
14. Arany AM, de Jong TJ, Kim HK, van Dam NM, Choi YH, van Mil HGJ, Verpoorte R,
van der Meijden E (2009) Genotype-environment interactions affect flower and fruit herbivory
and plant chemistry of Arabidopsis thaliana in a transplant experiment. Ecol Res 24:1161–1171
15. Kirk H, Vrieling K, Van Der Meijden E, Klinkhamer PGL (2010) Species by environment
interactions affect pyrrolizidine alkaloid expression in Senecio jacobaea, Senecio aquaticus,
and their hybrids. J Chem Ecol 36:378–387
16. Lankau RA, Kliebenstein DJ (2009) Competition, herbivory and genetics interact to determine
the accumulation and fitness consequences of a defence metabolite. J Ecol 97:78–88
17. LoPresti EF (2015) Chemicals on plant surfaces as a heretofore unrecognized, but ecologically
informative, class for investigations into plant defence. Biol Rev Camb Philos Soc. https://doi.
org/10.1111/brv.12212
18. Müller C, Riederer M (2005) Plant surface properties in chemical ecology. J Chem Ecol
31:2621–2651
19. Hopkins RJ, van dam NM, van Loon JJ (2009) Role of glucosinolates in insect-plant
relationships and multitrophic interactions. Annu Rev Entomol 54:57–83
20. Badenes-Pérez FR, Reichelt M, Gershenzon J, Heckel DG (2011) Phylloplane location of
glucosinolates in Barbarea spp. (Brassicaceae) and misleading assessment of host suitability
by a specialist herbivore. New Phytol 189:549–556
21. Shroff R, Schramm K, Jeschke V, Nemes P, Vertes A, Gershenzon J, Svatos A (2015)
Quantification of plant surface metabolites by matrix-assisted laser desorption-ionization
mass spectrometry imaging: glucosinolates on Arabidopsis thaliana leaves. Plant J 81:961–972
22. Hartmann T (1999) Chemical ecology of pyrrolizidine alkaloids. Planta 207:483–495
23. Chou MW, Fu PP (2006) Formation of DHP-derived DNA adducts in vivo from dietary
supplements and Chinese herbal plant extracts containing carcinogenic pyrrolizidine alkaloids.
Toxicol Ind Health 22:321–327
24. Langel D, Ober D, Pelser PB (2011) The evolution of pyrrolizidine alkaloid biosynthesis and
diversity in the Senecioneae. Phytochem Rev 10:3–74
25. Joosten L, Cheng D, Mulder PPJ, Vrieling K, van-Veen JA, Klinkhamer PGL (2011)
The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea
vulgaris. Phytochemistry 72:214–222
26. Rizk AM (1991) Naturally occurring pyrrolizidine alkaloids. CRC Press, Boca Raton, p 240
27. Wiedenfeld H, Roeder E, Bourauel T, Edgar J (2008) Pyrrolizidine alkaloids: structure and
toxicity. V&R unipress GmbH, Bonn
260
D. Cheng