Phenolic Compounds and Their Fates In Tropical Lepidopteran Larvae: Modifications In Alkaline Conditions

Journal of Chemical Ecology

Volumn 41, Issue 9, 2015, Pages 822-836

  Vihakas, Matti ^a   Gómez, Isrrael ^a   Karonen, Maarit ^a   Tähtinen, Petri ^a   Sääksjärvi, Ilari ^a   Salminen, Juha Pekka ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

Amazonia; Faeces; MRM; Neotropical; Oxidation; Rain forest; SRM; UHPLC DAD MS

Indexed keywords

ALKALINE ENVIRONMENT; CONCENTRATION (COMPOSITION); ENVIRONMENTAL FATE; FECES; HOST PLANT; INSECT; LARVA; LEAF; NEOTROPICAL KINGDOM; OXIDATION; PH; PHENOL; PLANT EXTRACT; RAINFOREST;

PHENOL DERIVATIVE; PLANT EXTRACT;

ANIMAL; CHEMISTRY; HERBIVORY; LARVA; LEPIDOPTERA; METABOLISM; OXIDATION REDUCTION REACTION; PH; PLANT; PLANT LEAF;

ANIMALS; HERBIVORY; HYDROGEN-ION CONCENTRATION; LARVA; LEPIDOPTERA; OXIDATION-REDUCTION; PHENOLS; PLANT EXTRACTS; PLANT LEAVES; PLANTS;

EID: 84943197889     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-015-0620-8     Document Type: Article

References (54)

1. Appel HM (1993) Phenolics in ecological interactions: the importance of oxidation. J Chem Ecol 19:1521–1552
2. Barbehenn RV (2002) Gut-based antioxidant enzymes in a polyphagous and a graminivorous grasshopper. J Chem Ecol 28:1329–1347
3. Barbehenn RV, Bumgarner SL, Roosen EF, Martin MM (2001) Antioxidant defenses in caterpillars: role of the ascorbate-recycling system in the midgut lumen. J Insect Physiol 47:349–357
4. Barbehenn RV, Poopat U, Spencer B (2003) Semiquinone and ascorbyl radicals in the gut fluids of caterpillars measured with EPR spectrometry. Insect Biochem Mol Biol 33:125–130
5. Barbehenn R, Dodick T, Poopat U, Spencer B (2005) Fenton-type reactions and iron concentrations in the midgut fluids of tree-feeding caterpillars. Arch Insect Biochem Physiol 60:32–43
6. Barbehenn RV, Jones CP, Hagerman AE, Karonen M, Salminen J-P (2006a) Ellagitannins have greater oxidative activities than condensed tannins and galloyl glucoses at high pH: potential impact on caterpillars. J Chem Ecol 32:2253–2267
7. Barbehenn RV, Jones CP, Karonen M, Salminen J–P (2006b) Tannin composition affects the oxidative activities of tree leaves. J Chem Ecol 32:2235–2251
8. Barbehenn R, Weir Q, Salminen J-P (2008) Oxidation of ingested phenolics in the tree-feeding caterpillar Orgyia leucostigma depends on foliar chemical composition. J Chem Ecol 34:748–756
9. Barbehenn R, Dukatz C, Holt C, Reese A, Martiskainen O, Salminen J-P, Yip L, Tran L, Constabel CP (2010) Feeding on poplar leaves by caterpillars potentiates foliar peroxidase action in their guts and increases plant resistance. Oecologia 164:993–1004
10. Bernays EA, Woodhead S (1982) Plant phenols utilized as nutrients by a phytophagous insect. Science 216:201–203
11. Blatt CTT, dos Santos MD, Salatino A (1998) Flavonoids of bignoniaceae from the “cerrado” and their possible taxonomic significance. Plant Syst Evol 210:289–292
12. Burghardt F, Fiedler K, Proksch P (1997) Uptake of flavonoids from Vicia villosa (fabaceae) by the lycaenid butterfly, Polyommatus icarus (Lepidoptera: lycaenidae). Biochem Syst Ecol 25:527–536
13. Burghardt F, Proksch P, Fiedler K (2001) Flavonoid sequestration by the common blue butterfly Polyommatus icarus: quantitative intraspecific variation in relation to larval host plant, sex and body size. Biochem. Syst Ecol 29:875–889
14. Canada AT, Giannella E, Nguyen TD, Mason RP (1990) The production of reactive oxygen species by dietary flavonols. Free Radic Biol Med 9:441–449
15. Cao G, Sofic E, Prior RL (1997) Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic Biol Med 22:749–760
16. Chen P-S, Li J-H, Liu T-Y, Lin T-C (2000) Folk medicine Terminalia catappa and its major tannin component, punicalagin, are effective against bleomycin-induced genotoxicity in Chinese hamster ovary cells. Cancer Lett 152:115–122
17. Dow JAT (1984) Extremely high pH in biological systems: a model for carbonate transport. Am J Phys 246:633–636
18. Engström MT, Pälijärvi M, Salminen J–P (2015) Rapid fingerprint analysis of plant extracts for ellagitannins, Gallic acid, and quinic acid derivatives and quercetin-, kaempferol- and myricetin-based flavonol glycosides by UPLC-QqQ-MS/MS. J Agric Food Chem 63:4068–4079
19. Felton GW, Donato K, Del Vechio RJ, Duffey SS (1989) Activation of plant foliar oxidases by insect feeding reduces nutritive quality of foliage for noctuid herbivores. J Chem Ecol 15:2667–2694
20. Ferreres F, Valentão P, Pereira JA, Bento A, Noites A, Seabra RM, Andrade PB (2008) HPLC-DAD-MS/MS-ESI screening of phenolic compounds in Pieris brassicae L. reared on Brassica rapa var. rapa L. J Agric Food Chem 56:844–853
21. Ferreres F, Fernandez F, Pereira DM, Pereira JA, Valentão P, Andrade PB (2009) Phenolics metabolism in insects: Pieris brassicae − Brassica oleracea var. costata ecological duo. J Agric Food Chem 57:9035–9043
22. Fine PVA, Miller ZJ, Mesones I, Irazuzta S, Appel HM, Henry M, Stevens H, Sääksjärvi IE, Schultz JC, Coley PD (2006) The growth-defense trade-off and habitat specialization by plants in Amazonian forests. Ecology 87:150–162
23. Green PWC, Stevenson PC, Simmonds MSJ, Sharma HC (2003) Phenolic compounds on the pod-surface of pigeonpea, Cajanus cajan, mediate feeding behavior of Helicoverpa armigera larvae. J Chem Ecol 29:811–821
24. Gringorten JL, Crawford DN, Harvey WR (1993) High pH in the ectoperitrophic space of the larval lepidopteran midgut. J Exp Biol 183:353–359
25. Gross EM, Brune A, Walenciaka O (2008) Gut pH, redox conditions and oxygen levels in an aquatic caterpillar: potential effects on the fate of ingested tannins. J Insect Physiol 54:462–471
26. Hagerman AE, Riedl KM, Jones GA, Sovik KN, Ritchard NT, Hartzfeld PW, Riechel TL (1998) High molecular weight plant polyphenolics (tannins) as biological antioxidants. J Agric Food Chem 46:1887–1892
27. Harborne JB (2001) Twenty-five years of chemical ecology. Nat Prod Rep 18:361–379
28. Hirayama C, Ono H, Tamura Y, Konno K, Nakamura M (2008) Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori. Phytochemistry 69:1141–1149
29. Johnson KS (2005) Plant phenolics behave as radical scavengers in the context of insect (Manduca sexta) hemolymph and midgut fluid. J Agric Food Chem 53:10120–10126
30. Kalliola R, Flores Paitan S (1998) Presentacion del estudio. In: Kalliola R, Flores Paitan S (eds) Geologia y desarrollo amazonico. Annales Universitatis Turkuensis Ser A II, vol 114. University of Turku,, Finland, pp. 11–15
31. Lahtinen M, Kapari L, Ossipov V, Salminen J-P, Haukioja E, Pihlaja K (2005) Biochemical transformation of birch leaf phenolics in larvae of six species of sawflies. Chemoecology 15:153–159
32. Lindroth RL (1988) Hydrolysis of phenolic glycosides by midgut β-glucosidases in Papilio glaucus subspecies. Insect Biochem 18:789–792
33. Lindroth RL, Peterson SS (1988) Effects of plant phenols on performance of southern armyworm larvae. Oecologia 75:185–189
34. Liu G, Rajesh N, Wang X, Zhang M, Wu Q, Li S, Chen B, Yao S (2011) Identification of flavonoids in the stems and leaves of Scutellaria baicalensis georgi. J Chromatogr B 879:1023–1028
35. Marengo J (1998) Climatologia en la zona de Iquitos, Peru. In: Kalliola R, Flores Paitan S (eds) Geologia y desarrollo amazonico. Annales Universitais Turkuensis Ser A II, vol 114. University of Turku, Finland, pp. 35–57
36. Matsuzaki K, Ishii R, Kobiyama K, Kitanaka S (2010) New benzophenone and quercetin galloyl glycosides from Psidium guajava L. J Nat Med 64:252–256
37. Moilanen J, Salminen J-P (2008) Ecologically neglected tannins and their biologically relevant activity: chemical structures of plant ellagitannins reveal their in vitro oxidative activity at high pH. Chemoecology 18:73–83
38. Opitz SEW, Müller C (2009) Plant chemistry and insect sequestration. Chemoecology 19:117–154
39. Pérez Gutiérrez RM, Mitchell S, Vargas Solis R (2008) Psidium guajava: a review of its traditional uses, phytochemistry and pharmacology. J Ethnopharmacol 117:1–27
40. Ramos CS, Vanin SA, Kato MJ (2008) Metabolism of (−)-grandisin from Piper solmsianum in coleoptera and Lepidoptera species. Phytochemistry 69:2157–2161
41. Ramos CS, Souza L, Kato MJ, Batista R (2012) Biotransformation of 4-nerolidylcatechol by Heraclides brasiliensis (Lepidoptera: papilionidae) reduces the toxicity of Piper umbellata (piperaceae). Chemoecology 22:39–45
42. Robbins CT, Hanley TA, Hagerman AE, Hjeljord O, Baker DL, Schwartz CC, Mautz WW (1987) Role of tannins in defending plants against ruminants: reduction in protein availability. Ecology 68:98–107
43. Romani A, Pinelli P, Galardi C, Mulinacci N, Tattini M (2002) Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L. Phytochem Anal 13:79–86
44. Ruokolainen K, Tuomisto H (1998) La vegetación de los terrenos no inundables (Tierra firme) en la selva Baja de la Amazonia peruana. In: Kalliola R, Flores Paitan S (eds) Geologia y desarrollo amazonico. Annales Universitais Turkuensis Ser A II, vol 114. University of Turku, Finland, pp. 253–344
45. Ruuhola T, Tikkanen O-P, Tahvanainen J (2001) Differences in host use efficiency of larvae of a generalist moth, Operophtera brumata on three chemically divergent Salix species. J Chem Ecol 27:1595–1615
46. Sääksjärvi IE, Ruokolainen K, Tuomisto H, Haataja S, Fine P, Cárdenas G, Mesones I, Vargas V (2006) Comparing composition and diversity of parasitoid wasps and plants in an Amazonian rain forest mosaic. J Trop Ecol 22:167–176
47. Salminen J-P, Karonen M (2011) Chemical ecology of tannins and other phenolics: we need a change in approach. Funct Ecol 25:325–338
48. Salminen J-P, Lempa K (2002) Effects of hydrolysable tannins on a herbivorous insect: fate of individual tannins in insect digestive tract. Chemoecology 12:203–211
49. Salminen J-P, Lahtinen M, Lempa K, Kapari L, Haukioja E, Pihlaja K (2004) Metabolic modifications of birch leaf phenolics by an herbivorous insect: Detoxification of flavonoid aglycones via glycosylation. Z Naturforsch 59c:437–444
50. Summers CB, Felton GW (1994) Prooxidant effects of phenolic acids on the generalist herbivore Helicoverpa zea (lepidoptera:noctuidae): potential mode of action for phenolic compounds in plant anti-herbivore chemistry. Insect Biochem Mol Biol 24:943–953
51. Tanaka T, Nokaka G-I, Nishioka I (1986) Tannins and related compounds. XLII. Isolation and characterization of four new hydrolyzable tannins, terflavins a and B, tergallagin and tercatain from the leaves of Terminalia catappa, L. Chem Pharm Bull 34:1039–1049
52. Tuominen A, Sundman T (2013) Stability and oxidation products of hydrolysable tannins in basic conditions detected by HPLC/DAD–ESI/QTOF/MS. Phytochem Anal 24:424–435
53. Vihakas, M, Tähtinen P, Ossipov V, Salminen J–P (2012) Flavonoid metabolites in the hemolymph of European pine sawfly (Neodiprion sertifer) larvae. J Chem Ecol 38:538–546
54. Vihakas M, Pälijärvi M, Karonen M, Roininen H, Salminen J–P (2014) Rapid estimation of the oxidative activities of individual phenolics in crude plant extracts. Phytochemistry 103:76–84