22. Gols R, van Dam NM, Reichelt M, Gershenzon J et al (2018) Seasonal and herbivore-induced
dynamics of foliar glucosinolates in wild cabbage (Brassica oleracea). Chemoecology
28(3):77–89
23. Waters ER (2003) Molecular adaptation and the origin of land plants. Mol Phylogenet Evol
29:456–463
24. Graham LE (1993) Origin of land plants. Wiley, New York
25. Sztein AE, Cohen JD, Slovin JP, Cooke TJ (1995) Auxin metabolism in representative land
plants. Am J Bot 82:1514–1521
26. Kroken SB, Graham LE, Cook ME (1996) Occurrence and evolutionary significance of resistant
cell walls in charophytes and bryophytes. Am J Bot 83:1241–1254
27. Lewis LA, McCourt RM (2004) Green algae and origin of land plants. Am J Bot 91
(10):1535–1556
28. Qiu YL, Lee J (2001) Transition to a land flora: a molecular phylogenetic perspective. J Phycol
36:799–802
29. Pichersky E, Lewinsohn E (2011) Convergent evolution in plant specialized metabolism. Ann
Rev Plant Biol 62:549–566
30. Lange BM (2015) The evolution of plant secretory structures and emergence of terpenoid
chemical diversity. Ann Rev Plant Biol 66:139–159
31. Taylor TN, Osborne JM (1996) The importance of fungi in shaping the paleoecosystem. Rev
Palaeobot Palynol 90:249–262
32. Asina F, Brzonova I, Voeller K, Kozliak E et al (2016) Biodegradation of lignin by fungi,
bacteria and laccases. Bioresour Technol 220:414–424
33. Singh HP, Batish DR, Kohli RK (1999) Autotoxicity: concept, organisms and ecological
significance. Crit Rev Plant Sci 18(6):757–772. https://doi.org/10.1080/07352689991309478
34. Zhou X, Zhang J, Pan D et al (2018) P-Coumaric can alter the composition of cucumber
rhizosphere microbial communities and induce negative plant-microbial interactions. Biol Fertil
Soils 54:363. https://doi.org/10.1007/s00374-018-1265-x
35. Bever JD, Platt TG, Morton ER (2012) Microbial population and community dynamics on plant
roots and their feedbacks on plant communities. Ann Rev Microbiol 66(1):265–283. https://doi.
org/10.1146/annurev-micro-092611-150107
36. Simpson BB, Neff JL (1983) Evolution and diversity of floral rewards. In: JonesCE, Little RJ
(ed) Handbook of experimental pollination biology. Van Nostrand Reinhold Co, New York
37. Richardson LL, Adler LS, Leonard AS et al (2015) Secondary metabolites in floral nectar
reduce parasite infections in bumblebees. Proc R Soc B 282:20142471. https://doi.org/10.1098/
rspb.2014.2471
38. Stevenson PC, Nicolson SW, Wright GA (2017) Plant secondary metabolites in nectar: impacts
on pollinators and ecological functions. Funct Ecol 31:65–75
39. Frolich C, HartmannT OD (2006) Tissue distribution and biosynthesis of 1,2-saturated
pyrrolizidine alkaloids in Phalaenopsis hybrids (Orchidaceae). Phytochemistry 67:1493–1502
40. Manson JS, Rasmann S, Halitschke R, ThomsonJD, Agrawal AA (2012) Cardenolides in nectar
may be more than a consequence of allocation to other plant parts: a phylogenetic study of
Asclepias. Funct Ecol 26:1100–1110
41. Irwin RE, Cook D, Richardson LL, Gardner DL (2014) Secondary compounds in floral rewards
of toxic rangeland plants: impacts on pollinators. J Agric Food Chem 62:7335–7344
42. Cook D, Manson JS, Gardner DR, Welch KD, Irwin RE (2013) Norditerpene alkaloid concentrations in tissues and floral rewards of larkspurs and impacts on pollinators. Biochem Syst Ecol
48:123–131
43. Wright GA, Baker DD, Palmer MJ, Stabler D, Mustard JA, Power EF, Borland AM, Stevenson
PC (2013) Caffeine in floral nectar enhances a pollinator’s memory of reward. Science
339:1202–1204. https://doi.org/10.1126/science.1228806
44. Jørgensen K, Stranden M, Sandoz J-C, Menzel R, Mustaparta H (2007) Effects of two bitter
substances on olfactory conditioning in the moth Heliothis virescens. J Exp Biol
210:2563–2573
1 Co-evolution of Secondary Metabolites During Biological Competition for. . .
15
dynamics of foliar glucosinolates in wild cabbage (Brassica oleracea). Chemoecology
28(3):77–89
23. Waters ER (2003) Molecular adaptation and the origin of land plants. Mol Phylogenet Evol
29:456–463
24. Graham LE (1993) Origin of land plants. Wiley, New York
25. Sztein AE, Cohen JD, Slovin JP, Cooke TJ (1995) Auxin metabolism in representative land
plants. Am J Bot 82:1514–1521
26. Kroken SB, Graham LE, Cook ME (1996) Occurrence and evolutionary significance of resistant
cell walls in charophytes and bryophytes. Am J Bot 83:1241–1254
27. Lewis LA, McCourt RM (2004) Green algae and origin of land plants. Am J Bot 91
(10):1535–1556
28. Qiu YL, Lee J (2001) Transition to a land flora: a molecular phylogenetic perspective. J Phycol
36:799–802
29. Pichersky E, Lewinsohn E (2011) Convergent evolution in plant specialized metabolism. Ann
Rev Plant Biol 62:549–566
30. Lange BM (2015) The evolution of plant secretory structures and emergence of terpenoid
chemical diversity. Ann Rev Plant Biol 66:139–159
31. Taylor TN, Osborne JM (1996) The importance of fungi in shaping the paleoecosystem. Rev
Palaeobot Palynol 90:249–262
32. Asina F, Brzonova I, Voeller K, Kozliak E et al (2016) Biodegradation of lignin by fungi,
bacteria and laccases. Bioresour Technol 220:414–424
33. Singh HP, Batish DR, Kohli RK (1999) Autotoxicity: concept, organisms and ecological
significance. Crit Rev Plant Sci 18(6):757–772. https://doi.org/10.1080/07352689991309478
34. Zhou X, Zhang J, Pan D et al (2018) P-Coumaric can alter the composition of cucumber
rhizosphere microbial communities and induce negative plant-microbial interactions. Biol Fertil
Soils 54:363. https://doi.org/10.1007/s00374-018-1265-x
35. Bever JD, Platt TG, Morton ER (2012) Microbial population and community dynamics on plant
roots and their feedbacks on plant communities. Ann Rev Microbiol 66(1):265–283. https://doi.
org/10.1146/annurev-micro-092611-150107
36. Simpson BB, Neff JL (1983) Evolution and diversity of floral rewards. In: JonesCE, Little RJ
(ed) Handbook of experimental pollination biology. Van Nostrand Reinhold Co, New York
37. Richardson LL, Adler LS, Leonard AS et al (2015) Secondary metabolites in floral nectar
reduce parasite infections in bumblebees. Proc R Soc B 282:20142471. https://doi.org/10.1098/
rspb.2014.2471
38. Stevenson PC, Nicolson SW, Wright GA (2017) Plant secondary metabolites in nectar: impacts
on pollinators and ecological functions. Funct Ecol 31:65–75
39. Frolich C, HartmannT OD (2006) Tissue distribution and biosynthesis of 1,2-saturated
pyrrolizidine alkaloids in Phalaenopsis hybrids (Orchidaceae). Phytochemistry 67:1493–1502
40. Manson JS, Rasmann S, Halitschke R, ThomsonJD, Agrawal AA (2012) Cardenolides in nectar
may be more than a consequence of allocation to other plant parts: a phylogenetic study of
Asclepias. Funct Ecol 26:1100–1110
41. Irwin RE, Cook D, Richardson LL, Gardner DL (2014) Secondary compounds in floral rewards
of toxic rangeland plants: impacts on pollinators. J Agric Food Chem 62:7335–7344
42. Cook D, Manson JS, Gardner DR, Welch KD, Irwin RE (2013) Norditerpene alkaloid concentrations in tissues and floral rewards of larkspurs and impacts on pollinators. Biochem Syst Ecol
48:123–131
43. Wright GA, Baker DD, Palmer MJ, Stabler D, Mustard JA, Power EF, Borland AM, Stevenson
PC (2013) Caffeine in floral nectar enhances a pollinator’s memory of reward. Science
339:1202–1204. https://doi.org/10.1126/science.1228806
44. Jørgensen K, Stranden M, Sandoz J-C, Menzel R, Mustaparta H (2007) Effects of two bitter
substances on olfactory conditioning in the moth Heliothis virescens. J Exp Biol
210:2563–2573
1 Co-evolution of Secondary Metabolites During Biological Competition for. . .
15