21. Rosenthal GA, Berenbaum MR (1992) Herbivores: their interactions with secondary plant
metabolites. Vol. 2. Ecological and evolutionary processes. Academic, San Diego
22. Detzel A, Wink M (1993) Attraction, deterrence or intoxication of bees (Apis mellifera) by plant
allelochemicals. Chemoecology 4:8–18
23. Kaczorowski R, Koplovich A, Sporer F, Wink M, Katzir G, Izhaki I, Markman S (2014)
Immediate effects of nectar robbing by Palestine sunbirds (Nectarinia osea) on nectar alkaloid
concentrations in tree tobacco (Nicotiana glauca). J Chem Ecol 40:325–330
24. Yi W, Hengwu J, Peihua J (2019) Huabin Z Functional divergence of bitter taste receptors in a
nectar-feeding bird. Biol Lett. https://doi.org/10.1098/rsbl.2019.0461
25. Ali JG, Agrawal AA (2012) Specialist versus generalist insect herbivores and plant defense.
Trends Plant Sci 17:292–302
26. Hartmann T (2004) Plant-derived secondary metabolites as defensive chemicals in herbivorous
insects: a case study in chemical ecology. Planta 219:1–4
27. Hilker M, Meiners T (2011) Plants and insect eggs: how do they affect each other?
Phytochemistry 72:1612–1623
28. Wink M (2016) Secondary metabolites: deterring herbivores. In: Encyclopedia of life sciences
(ELS). Wiley, Chichester. https://doi.org/10.1002/9780470015902.a0000918.pub3
29. Kelly CA, Bowers MD (2016) Preference and performance of generalist and specialist
herbivores on chemically defended host plants. Ecol Entomol 41:308–316
30. Wink M (2016) Evolution, diversification, and function of secondary metabolites.
In: Encyclopedia of evolutionary biology, vol 4. https://doi.org/10.1016/B978-0-12-8000496.00263-8
31. Holzinger F, Frick C, Wink M (1992) Molecular base for the insensitivity of the monarch
(Danaus plexippus) to cardiac glycosides. FEBS Lett 314:477–480
32. Aardema ML, Andolfatto P (2016) Phylogenetic incongruence and evolutionary origins of
cardenolide-resistant forms of Na
+ , K
+ -ATPase in Danaus butterflies. Evolution 70:1913–1921
33. Dobler S, Dalla S, Wagschal V, Agrawal AA (2012) Community-wide convergent evolution in
insect adaptation to toxic cardenolides by substitutions in the Na, K-ATPase. PNAS
109:13040–13045
34. Holzinger F, Wink M (1996) Mediation of cardiac glycoside insensitivity in the monarch
(Danaus plexippus): role of an amino acid substitution in the ouabain binding site of Na
+ ,
K
+ -ATPase. J Chem Ecol 22:1921–1937
35. Karageorgi M et al (2019) Genome editing retraces the evolution of toxin resistenace in the
monarch butterfly. Nature 574:409–412
36. Boppré M (1986) Insects pharmacophagously utilising defensive plant chemicals (pyrrolizidine
alkaloids). Naturwissenschaften 73:17–26
37. Eisner T, Eisner M, Siegler M (2007) Secret weapons: defenses of insects, spiders, scorpions,
and other many-legged creatures. Harvard University Press, Boston
38. Hartmann T (1999) Chemical ecology of pyrrolizidine alkaloids. Planta 207:483–495
39. Laurent P, Braekman J-C, Daloze D (2005) Insect chemical defense. Top Curr Chem
240:167–229
40. Macel M (2011) Attract and deter: a dual role for pyrrolizidine alkaloids in plant-insect
interactions. Phytochem Rev 10:75–82
41. Wink M (1992) The role of quinolizidine alkaloids in plant insect interactions. In: Bernays EA
(ed) Insect-plant interactions, vol IV. CRC-Press, Boca Raton, pp 133–169
42. Zagrobelny M, Moller BL (2011) Cyanogenic glucosides in the biological warfare between
plants and insects: the Burnet mothBirdsfoot trefoil model system. Phytochemistry
72:1585–1592
43. Wink M (2019) Quinolizidine and pyrrolizidine alkaloid chemical ecology – a mini-review on
their similarities and differences. J Chem Ecol 45:109–115
44. Wink M, Van Wyk BE (2008) Mind-altering and poisonous plants of the world. BRIZA,
Pretoria
45. Brown KS, Trigo JR (1995) The ecological activity of alkaloids. In: Cordell GA (ed)
The alkaloids, vol 47. Acedemic press, New York, pp 227–356
8 Evolution of the Angiosperms and Co-evolution of Secondary Metabolites. . .
173
metabolites. Vol. 2. Ecological and evolutionary processes. Academic, San Diego
22. Detzel A, Wink M (1993) Attraction, deterrence or intoxication of bees (Apis mellifera) by plant
allelochemicals. Chemoecology 4:8–18
23. Kaczorowski R, Koplovich A, Sporer F, Wink M, Katzir G, Izhaki I, Markman S (2014)
Immediate effects of nectar robbing by Palestine sunbirds (Nectarinia osea) on nectar alkaloid
concentrations in tree tobacco (Nicotiana glauca). J Chem Ecol 40:325–330
24. Yi W, Hengwu J, Peihua J (2019) Huabin Z Functional divergence of bitter taste receptors in a
nectar-feeding bird. Biol Lett. https://doi.org/10.1098/rsbl.2019.0461
25. Ali JG, Agrawal AA (2012) Specialist versus generalist insect herbivores and plant defense.
Trends Plant Sci 17:292–302
26. Hartmann T (2004) Plant-derived secondary metabolites as defensive chemicals in herbivorous
insects: a case study in chemical ecology. Planta 219:1–4
27. Hilker M, Meiners T (2011) Plants and insect eggs: how do they affect each other?
Phytochemistry 72:1612–1623
28. Wink M (2016) Secondary metabolites: deterring herbivores. In: Encyclopedia of life sciences
(ELS). Wiley, Chichester. https://doi.org/10.1002/9780470015902.a0000918.pub3
29. Kelly CA, Bowers MD (2016) Preference and performance of generalist and specialist
herbivores on chemically defended host plants. Ecol Entomol 41:308–316
30. Wink M (2016) Evolution, diversification, and function of secondary metabolites.
In: Encyclopedia of evolutionary biology, vol 4. https://doi.org/10.1016/B978-0-12-8000496.00263-8
31. Holzinger F, Frick C, Wink M (1992) Molecular base for the insensitivity of the monarch
(Danaus plexippus) to cardiac glycosides. FEBS Lett 314:477–480
32. Aardema ML, Andolfatto P (2016) Phylogenetic incongruence and evolutionary origins of
cardenolide-resistant forms of Na
+ , K
+ -ATPase in Danaus butterflies. Evolution 70:1913–1921
33. Dobler S, Dalla S, Wagschal V, Agrawal AA (2012) Community-wide convergent evolution in
insect adaptation to toxic cardenolides by substitutions in the Na, K-ATPase. PNAS
109:13040–13045
34. Holzinger F, Wink M (1996) Mediation of cardiac glycoside insensitivity in the monarch
(Danaus plexippus): role of an amino acid substitution in the ouabain binding site of Na
+ ,
K
+ -ATPase. J Chem Ecol 22:1921–1937
35. Karageorgi M et al (2019) Genome editing retraces the evolution of toxin resistenace in the
monarch butterfly. Nature 574:409–412
36. Boppré M (1986) Insects pharmacophagously utilising defensive plant chemicals (pyrrolizidine
alkaloids). Naturwissenschaften 73:17–26
37. Eisner T, Eisner M, Siegler M (2007) Secret weapons: defenses of insects, spiders, scorpions,
and other many-legged creatures. Harvard University Press, Boston
38. Hartmann T (1999) Chemical ecology of pyrrolizidine alkaloids. Planta 207:483–495
39. Laurent P, Braekman J-C, Daloze D (2005) Insect chemical defense. Top Curr Chem
240:167–229
40. Macel M (2011) Attract and deter: a dual role for pyrrolizidine alkaloids in plant-insect
interactions. Phytochem Rev 10:75–82
41. Wink M (1992) The role of quinolizidine alkaloids in plant insect interactions. In: Bernays EA
(ed) Insect-plant interactions, vol IV. CRC-Press, Boca Raton, pp 133–169
42. Zagrobelny M, Moller BL (2011) Cyanogenic glucosides in the biological warfare between
plants and insects: the Burnet mothBirdsfoot trefoil model system. Phytochemistry
72:1585–1592
43. Wink M (2019) Quinolizidine and pyrrolizidine alkaloid chemical ecology – a mini-review on
their similarities and differences. J Chem Ecol 45:109–115
44. Wink M, Van Wyk BE (2008) Mind-altering and poisonous plants of the world. BRIZA,
Pretoria
45. Brown KS, Trigo JR (1995) The ecological activity of alkaloids. In: Cordell GA (ed)
The alkaloids, vol 47. Acedemic press, New York, pp 227–356
8 Evolution of the Angiosperms and Co-evolution of Secondary Metabolites. . .
173