51. Gebhardt Y, Witte S, Forkmann G (2005) Molecular evolution of flavonoid dioxygenases in
the family Apiaceae. Phytochemistry 66:1273–1284. https://doi.org/10.1016/j.
phytochem.2005.03.030
52. Koes R, Verweij W, Quattrocchio F (2005) Flavonoids: a colorful model for the regulation and
evolution of biochemical pathways. Trends Plant Sci 10:236–242. https://doi.org/10.1016/j.
tplants.2005.03.002
53. Stafford HA (1991) Flavonoid evolution: an enzymic approach. Plant Physiol 96:680–685.
https://doi.org/10.1104/pp.96.3.680
54. Koes RE, Quattrocchio F, Mol JN (1994) The flavonoid biosynthetic pathway in plants:
function and evolution. BioEssays 16(2):123–132
55. Lattanzio V, Lattanzio VMT, Cardinali A, Amendola V (2006) Role of phenolics in the
resistance mechanisms of plants against fungal pathogens and insects. Phytochem: Adv Res
661(2):23–67
56. Gurevitch J, Scheiner SM, Fox GA (2002) The ecology of plants. Ecol Plants. https://doi.org/
10.1086/527596
57. Wink M (2003) Evolution of secondary metabolites from an ecological and molecular
phylogenetic perspective. Phytochemistry 64(1):3–19. https://doi.org/10.1016/S0031-9422
(03)00300-5
58. Heidel-Fischer HM, Vogel H (2015) Molecular mechanisms of insect adaptation to plant
secondary compounds. Curr Opin Insect Sci 8:8–14. https://doi.org/10.1016/j.
cois.2015.02.004
59. Züst T, Agrawal AA (2016) Mechanisms and evolution of plant resistance to aphids. Nature
Plants 2:1–9. https://doi.org/10.1038/nplants.2015.206
60. Kiddle GA, Doughty KJ, Wallsgrove RM (1994) Salicylic acid-induced accumulation of
glucosinolates in oilseed rape (Brassica napus L.) leaves. J Exp Bot 45:1343–1346. https://
doi.org/10.1093/jxb/45.9.1343
61. Zang Y, Ge J, Huang L (2015) Leaf and root glucosinolate profiles of Chinese cabbage
(Brassica rapa ssp. pekinensis) as a systemic response to methyl jasmonate and salicylic
acid elicitation. J Zhejiang Univ Sci B 16:696–708. https://doi.org/10.1631/jzus.B1400370
62. Hansen CH, Du L, Naur P (2001) CYP83B1 is the oxime-metabolizing enzyme in the
glucosinolate pathway in Arabidopsis. J Biol Chem 276:24790–24796. https://doi.org/
10.1074/jbc.M102637200
63. Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of
glucosinolates and isothiocyanates among plants. Phytochemistry 56(1):5–51. https://doi.
org/10.1016/S0031-9422(00)00316-2
64. Naur P, Petersen BL, Mikkelsen MD (2003) P450 enzymes metabolizing oximes in the
biosynthesis of Glucosinolates in Arabidopsis. Plant Physiol 133(1):63–72. https://doi.org/
10.1104/pp.102.019240.1
65. Turlings TCJ, Erb M (2018) Tritrophic interactions mediated by herbivore-induced plant
volatiles: mechanisms, ecological relevance, and application potential. Annu Entomol
63:433–452. https://doi.org/10.1146/annurev-ento-020117-043507
66. Howe GA, Herde M (2015) Interaction of plant defense compounds with the insect gut: new
insights from genomic and molecular analyses. Curr Opin Insect Sci 9:62–68. https://doi.org/
10.1016/j.cois.2015.03.004
67. Fischbach RJ, Staudt M, Zimmer I, Rambal S, Schnitzler JP (2002) Seasonal pattern of
monoterpene synthase activities in leaves of the evergreen tree Quercus ilex. Physiol Plant
114(3):354–360. https://doi.org/10.1034/j.1399-3054.2002.1140304.x
68. Rasmann S, Köllner T, Degenhardt J et al (2005) Recruitment of entomopathogenic nematodes
by insect-damaged maize roots. Nature 434:732–737. https://doi.org/10.1038/nature03451
69. Guenther A, Monson R (1997) Plant production and emission of volatile organic compounds.
Bioscience 47:373–383. https://doi.org/10.2307/1313152
70. Achotegui-Castells A, Llusià J, Hódar JA, Peñuelas J (2013) Needle terpene concentrations
and emissions of two coexisting subspecies of scots pine attacked by the pine processionary
moth (Thaumetopoea pityocampa). Acta Physiol Plant 35:3047–3058. https://doi.org/
10.1007/s11738-013-1337-3
2 Plant-Insect Interaction: The Saga of Molecular Coevolution
41
the family Apiaceae. Phytochemistry 66:1273–1284. https://doi.org/10.1016/j.
phytochem.2005.03.030
52. Koes R, Verweij W, Quattrocchio F (2005) Flavonoids: a colorful model for the regulation and
evolution of biochemical pathways. Trends Plant Sci 10:236–242. https://doi.org/10.1016/j.
tplants.2005.03.002
53. Stafford HA (1991) Flavonoid evolution: an enzymic approach. Plant Physiol 96:680–685.
https://doi.org/10.1104/pp.96.3.680
54. Koes RE, Quattrocchio F, Mol JN (1994) The flavonoid biosynthetic pathway in plants:
function and evolution. BioEssays 16(2):123–132
55. Lattanzio V, Lattanzio VMT, Cardinali A, Amendola V (2006) Role of phenolics in the
resistance mechanisms of plants against fungal pathogens and insects. Phytochem: Adv Res
661(2):23–67
56. Gurevitch J, Scheiner SM, Fox GA (2002) The ecology of plants. Ecol Plants. https://doi.org/
10.1086/527596
57. Wink M (2003) Evolution of secondary metabolites from an ecological and molecular
phylogenetic perspective. Phytochemistry 64(1):3–19. https://doi.org/10.1016/S0031-9422
(03)00300-5
58. Heidel-Fischer HM, Vogel H (2015) Molecular mechanisms of insect adaptation to plant
secondary compounds. Curr Opin Insect Sci 8:8–14. https://doi.org/10.1016/j.
cois.2015.02.004
59. Züst T, Agrawal AA (2016) Mechanisms and evolution of plant resistance to aphids. Nature
Plants 2:1–9. https://doi.org/10.1038/nplants.2015.206
60. Kiddle GA, Doughty KJ, Wallsgrove RM (1994) Salicylic acid-induced accumulation of
glucosinolates in oilseed rape (Brassica napus L.) leaves. J Exp Bot 45:1343–1346. https://
doi.org/10.1093/jxb/45.9.1343
61. Zang Y, Ge J, Huang L (2015) Leaf and root glucosinolate profiles of Chinese cabbage
(Brassica rapa ssp. pekinensis) as a systemic response to methyl jasmonate and salicylic
acid elicitation. J Zhejiang Univ Sci B 16:696–708. https://doi.org/10.1631/jzus.B1400370
62. Hansen CH, Du L, Naur P (2001) CYP83B1 is the oxime-metabolizing enzyme in the
glucosinolate pathway in Arabidopsis. J Biol Chem 276:24790–24796. https://doi.org/
10.1074/jbc.M102637200
63. Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of
glucosinolates and isothiocyanates among plants. Phytochemistry 56(1):5–51. https://doi.
org/10.1016/S0031-9422(00)00316-2
64. Naur P, Petersen BL, Mikkelsen MD (2003) P450 enzymes metabolizing oximes in the
biosynthesis of Glucosinolates in Arabidopsis. Plant Physiol 133(1):63–72. https://doi.org/
10.1104/pp.102.019240.1
65. Turlings TCJ, Erb M (2018) Tritrophic interactions mediated by herbivore-induced plant
volatiles: mechanisms, ecological relevance, and application potential. Annu Entomol
63:433–452. https://doi.org/10.1146/annurev-ento-020117-043507
66. Howe GA, Herde M (2015) Interaction of plant defense compounds with the insect gut: new
insights from genomic and molecular analyses. Curr Opin Insect Sci 9:62–68. https://doi.org/
10.1016/j.cois.2015.03.004
67. Fischbach RJ, Staudt M, Zimmer I, Rambal S, Schnitzler JP (2002) Seasonal pattern of
monoterpene synthase activities in leaves of the evergreen tree Quercus ilex. Physiol Plant
114(3):354–360. https://doi.org/10.1034/j.1399-3054.2002.1140304.x
68. Rasmann S, Köllner T, Degenhardt J et al (2005) Recruitment of entomopathogenic nematodes
by insect-damaged maize roots. Nature 434:732–737. https://doi.org/10.1038/nature03451
69. Guenther A, Monson R (1997) Plant production and emission of volatile organic compounds.
Bioscience 47:373–383. https://doi.org/10.2307/1313152
70. Achotegui-Castells A, Llusià J, Hódar JA, Peñuelas J (2013) Needle terpene concentrations
and emissions of two coexisting subspecies of scots pine attacked by the pine processionary
moth (Thaumetopoea pityocampa). Acta Physiol Plant 35:3047–3058. https://doi.org/
10.1007/s11738-013-1337-3
2 Plant-Insect Interaction: The Saga of Molecular Coevolution
41