Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions

Phytochemistry Reviews

Volumn 2, Issue 3, 2003, Pages 321-330

  Harmatha, Juraj ^a   Dinan, Laurence ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Antagonists; Drosophila melanogaster BII cell line bioassay; Ecdysteroid receptor; Insect antifeedant; Lignan; Phenylpropanoid; Resveratrol; Stilbenoid

Indexed keywords

ECDYSONE; ECDYSONE RECEPTOR; ECDYSTEROID; INSECTICIDE; LIGNAN; LIGNAN DERIVATIVE; RECEPTOR BLOCKING AGENT; RESVERATROL; STILBENE DERIVATIVE;

AGONIST; BINDING AFFINITY; BINDING SITE; BIOASSAY; CELL LINE; CHEMICAL INTERACTION; COMPARATIVE STUDY; CONFERENCE PAPER; DROSOPHILA MELANOGASTER; ENDOCRINE SYSTEM; FEEDING; INSECT; INSECT DEVELOPMENT; INSECTICIDAL ACTIVITY; LEUZEA; METABOLITE; METAMORPHOSIS; MOLTING; NONHUMAN; PLANT; PLANT DEFENSE; PLANT INSECT INTERACTION; PRIORITY JOURNAL; PUBLICATION; STRUCTURE ACTIVITY RELATION;

DROSOPHILA MELANOGASTER; HEXAPODA; INSECTA;

EID: 23844550925     PISSN: 15687767     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:PHYT.0000045494.98645.a3     Document Type: Conference Paper

References (72)

1. Ayres DC & Loike JD (1990) Lignans: Chemical, biological and clinical properties, Cambridge University Press, Cambridge.
2. Bernard CB, Arnason JT, Philogène BJR, Lam J & Waddell T (1989) Effect of lignans and other secondary metabolites of the Asteraceae on the mono-oxygenase activity of European corn borer. Phytochemistry 28: 1373-1377.
3. Bernard C B, Krishnamurty HG, Chauret D, Durst T, Philogène BJR, Sanchez-Vindas P, Hasbun C, Poveda L, San Roman L & Arnason JT (1995) Insecticidal defenses of Piperaceae from the neotropics. J. Chem. Ecol. 21: 801-814.
4. Bloszyk E., Nawrot J, Harmatha J, Drozdz B & Chmielewicz Z (1990) Effectiveness of antifeedants of plant origin in protection of packaging materials against storage insects. J. Appl. Entomol. 110: 96-100.
5. Boll PM, Parmar VS, Tyagi OD, Prasad A, Wengel J & Olsen CE (1994) Some recent isolation studies from potential insecticidal Piper species. Pure Appl. Chem. 66: 2339-2342.
6. Bowers WS (1968) Juvenile hormone: Activity of natural and synthetic synergists. Science 161: 895-897.
7. Bowers WS (1991) Insect hormones and antihormones in plants. In: Rosenthal GA & Berenbaum MR (eds) Herbivores. Their interaction with secondary plant metabolites, Second Edition, Vol. I (pp. 431-456). Academic Press, San Diego.
8. Cabral MMO, Azambuja P, Gottlieb OR & Garcia ES (2000a) Effects of some lignans and neolignans on the development and excretion of Rhodnius prolixus. Fitoterapia 71: 1-9.
9. Cabral MMO, Kelecom A & Garcia ES (1999) Effects of the lignan, pinoresinol on the moulting cycle of the bloodsucking bug Rhodnius prolixus and of the milkweed bug Oncopeltus fasciatus. Fitoterapia 70: 561-567.
10. Cabral MMO, Kollien AH, Kleffmann T, Azambuja P, Gottlieb OR, Garcia ES, & Schaub GA (2000b) Rhodnius prolixus: effects of the neolignan burchellin on in vivo and in vitro diuresis. Parasitol. Res. 86: 710-716.
11. Casida JE (1970) Mixed-function oxidase involvement in the biochemistry of insecticide synergists. J. Agr. Food Chem. 18: 753-772.
12. Chauret DC, Bernard CB, Arnason JT & Durst T (1996) Insecticidal neolignans from Piper decurrens. J. Nat. Prod. 59: 152-155.
13. Davin LB & Lewis NG (2000) Dirigent proteins and dirigent sites explain the mystery of specificity of radical precursor coupling in lignan and lignin biosynthesis, Plant Physiol. 123: 453-461.
14. Dhadialla TS, Carlson GR & Le DP (1998) New insecticides with ecdysteroidal and juvenile hormone activity, Annu. Rev. Entomol. 43: 545-569.
15. II cell bioassay for ecdysteroid agonist and antagonist activities. Cell. Mol. Life Sci. 58: 321-342.
16. II cell in vitro assay, Environ. Toxicol. Chem. 20: 2038-2046.
17. Dinan L, Hormann RE & Fujimoto T (1999a) An extensive ecdysteroid CoMFA. J. Comp.-Aid. Molec. Design 13: 185-207.
18. Dinan L, Savchenko T, Whiting P & Sarker SD (1999b) Plant natural products as insect steroid receptor agonists and antagonists. Pestic. Sci. 55: 331-335.
19. Erdtman H & Harmatha J (1979) Phenolic and terpenoid heartwood constituents of Libocedrus yateensis. Phytochemistry 18: 1495-1500.
20. Gang DR, Dinkova-Kostova AT, Davin LB, Lewis NG (1997) Phylogenetic links in plant defense systems: Lignans, isoflavonoids, and their reductases. Phytochemicals for pest control. ACS Symp. Ser. 658: 58-89.
21. Garcia ES, Cabral MMO, Schaub GA, Gottlieb OR & Azambuja P (2000) Effects of lignoids on a hematophagous bug, Rhodnius prolixus: feeding, ecdysis and diuresis. Phytochemistry 55: 611-616.
22. Gonzalez-Coloma A, Escoubas P, Mizutani J & Lajide L (1994) Insect growth inhibitors from Machilus japonica. Phytochemistry 35: 607-610.
23. Haller HL, Mc Govran ER, Goodhue LD & Sullivan WN (1942a) The synergistic action of sesamin with pyrethrum insecticides. J. Org. Chem. 7: 183-184.
24. Haller HL, Mc Govran ER, Goodhue LD & Sullivan WN (1942b) Some compounds related to sesamin: Their structures and their synergistic effect with pyrethrum insecticides. J. Org. Chem. 7: 185-188.
25. Hajdu Z, Varga E, Hohmann J, Kalman A, Argay G & Gunther G (1998) A stilbene from the roots of Leuzea carthamoides. J. Nat. Prod. 10: 1298-1299.
26. Harmatha J (2000) Chemo-ecological role of spirostanol saponins in the interaction between plants and insects. In Oleszek W & Marston A (eds.) Saponins in Food, Feedstuffs and Medicinal Plants, Proc. Phytochem. Soc. Europe 45 (pp. 129-141). Kluwer Academic Publishers, Dordrecht, The Netherlands.
27. Harmatha J (2002) Phenylpropanoids, lignans and their biological activities. In Kohout L (ed.) Chemistry and Biochemistry of Natural Compounds, Vol. 27 (pp. 117-142). Institute of Organic Chemistry and Biochemistry, Prague (textbook in Czech).
28. Harmatha J, Buděšínský M & Trka A (1982) The structure of yatein. Determination of the positions, and configurations of benzyl groups in lignans of the 2.3-dibenzylbutyrolactone type. Collect. Czech. Chem. Commun. 47: 644-663.
29. Harmatha J, Buděšínský M, Vokáč K, Pavlík M, Grüner K & Laudová V (2003) Lignans and serotonin phenylpropanoids from the seeds of Leuzea carthamoides. Phytochemistry, submitted.
30. II bioassay. Arch. Insect Biochem. Physiol. 35: 219-225.
31. Harmatha J & Dinan L (2002) Interaction of dimeric ecdysteroids, glycosidic ecdysteroid conjugates and ecdysis-disturbing saponins with the ecdysteroid receptor assessed by means of the Drosophila melanogaster B-II bioassay. In Konopinska D (ed): Arthropods: Chemical, physiological and environmental aspects (pp. 79-84). Wroclaw Technical University Press, Wroclaw, Poland.
32. II bioassay. Insect Biochem. Molec. Biol. 32: 181-185.
33. Harmatha J & Nawrot J (1984) Comparison of feeding deterrent activity of some sesquiteipene lactones and a lignan lactone towards selected insect storage pests. Biochem. Syst. Ecol. 12: 95-98.
34. Harmatha J & Nawrot J (1988) The role of lignans in plant - insect interaction. In: Sehnal F, Zabza A & Denlinger DL (eds.) Endocrinological Frontiers in Physiological Insect Ecology (pp. 81-86). Wroclaw Technical University Press, Wroclaw, Poland.
35. Harmatha J & Nawrot J (2002) Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxy (piperonyl) structure moiety. Entomol. Exp. Appl. 104/1: 51-60.
36. Harmatha J, Nawrot J & Bloszyk E. (1991) Action of plant allelochemicals with antifeeding effect on selected stored product insect pests. In: Hrdý I (ed) Insect Chemical Ecology (pp. 245-250). Academia Praha and SPB Acad. Publ., The Hague.
37. Hartmann T. (1996) Diversity and variability of plant secondary metabolism: A mechanistic view. Entomol. Exp. Appl. 80: 177-188.
38. Jensen S., Hansen J & Boll PM (1993) Lignans and neolignans from Piperaceae. Phytochemistry 33: 523-530.
39. II cell line. Cell. Mol. Life Sci. 57: 333-336.
40. Kozawa M., Baba K, Matsuyama Y, Kido T, Sakai M & Takemoto T (1982) Components of the root of Anthriscus sylvestris HOFFM. II. Insecticidal activity. Chem. Pharm. Bull. 30: 2885-2888.
41. Křecková J, Křeček J & Harmatha J (1988) Feeding deterrent activity of certain plant substances against subterranean termite Coptotermes formosanus (Rhinotermitidae; Isoptera). In: Sehnal F, Zabza A & Denlinger DL (eds) Endocrinological Frontiers in Physiological Insect Ecology (pp. 105-107). Wroclaw Technical University Press, Wroclaw, Poland.
42. Lafont R, Harmatha I, Marion-Poll F, Dinan L & Wilson, ID (2002) Ecdybase - The Ecdysone Handbook, 3rd Edition, http://ecdybase.org, Cybersales, Praha, Czech Republic.
43. Lajide L, Escoubas P & Mizutani J (1995) Termite antifeedant activity in Xylopia aethiopica. Phytochemistry 40: 1105-1112.
44. MacRae WD & Towers GHN (1984) Biological activities of lignans. Phytochemistry 23: 1207-1220.
45. Matsubara H (1972) Studies on synergist for insecticides. XXVII. On synergistic effect of several lignans on pyrethrins and allethrin. Bull. Inst. Chem. Res., Kyoto Univ. 50: 197-205.
46. Meng YH, Bourne PC, Whiting P, Sik V, Dinan L (2001) Identification and ecdysteroid antagonist activity of three oligostilbenes from the seeds of Carex pendula (Cyperaceae). Phytochemistry 57: 393-100.
47. Miyazawa M, Ishikawa Y, Kasahara H, Yamanaka J & Kameoka H (1994) An insect growth inhibitory lignan from flower buds of Magnolia fargesii. Phytochemistry 35: 611-613.
48. Miyazawa M, Hirota K, Fukuyama M, Ishikawa Y & Kameoka H (1998) Insecticidal lignans against Drosophila melanogaster from fruits of Schisandra chinensis. Nat. Prod. Lett. 12: 175-180.
49. Miyazawa M, Fukuyama M, Yoshio K, Kato T & Ishikawa Y (1999) Biologically active components against Drosophila melanogaster from Podophyllum hexandrum. J. Agric. Food. Chem. 47: 5108-5110.
50. Nawrot J, Bloszyk E, Harmatha J, Novotný L & Drozdz B (1986a) Action of antifeedants of plant origin on beetles infesting stored products. Acta Entomol. Bohemoslov 83: 327-335.
51. Nawrot J & Harmatha J (1994) Natural products as antifeedants against stored products insects. Review article. Postharvest News Inform. 5/2: 17N-21N.
52. Nawrot J, Harmatha J & Bloszyk E (1986b) Secondary plant metabolites with antifeeding activity and their effects on some stored product insects. In: Donahaye E & Navarro S (eds) Proceedings of the 4th International Working Conference on Stored-Product Protection (pp. 591-597). Tel Aviv, Israel.
53. Nawrot J, Harmatha J, Kostova I & Ognyanov I. (1989) Antifeeding activity of rotenone and some derivatives towards selected insect storage pests. Biochem. Syst. Ecol. 17: 55-57.
54. Nawrot J, Koul O, Isman MB & Harmatha J (1991) Naturally occurring antifeedants: Effects on two polyphagous lepidopterans. J. Appl. Entomol. 112: 194-201.
55. Neal JJ (1989) Myristicin, safrole, and fagaramide as phytosynergists of xanthotoxin. J. Chem. Ecol. 15: 309-315.
56. Oberdörster E, Clay MA, Cottam DM, Wilmot FA, McLachlan JA & Milner MJ (2001) Common phytochemicals are ecdysteroid agonists and antagonists: A possible evolutionary link between vertebrate and invertebrate steroid hormones. J. Steroid Biochem. Mol. Biol. 77: 229-238.
57. Oberlander H, Silhacek DL & Porcheron P (1995) Non-steroidal ecdysteroid agonists: tools for the study of hormonal action. Arch. Insect Biochem. Physiol. 28: 209-223.
58. Pavlík M, Laudová V, Grüner K, Vokáč K & Harmatha J (2002) High-performance liquid chromatographic analysis and separation of N-feruloylserotonin isomers. J. Chromatogr. B 770: 291-295.
59. Píš J, Buděšínský M, Vokáč K, Laudová V & Harmatha J (1994) Ecdysteroids from the roots of Leuzea carthamoldes. Phytochemistry 37: 707-711.
60. Poplawski J, Lozowicka B, Dubis A, Lachowska B, Winiecki Z & Nawrot J (2000) Feeding-deterrent activity of alpha-asarone isomers against some stored Coleoptera. Pest Manage. Sci. 56: 560-564.
61. Raffaelli B, Hoikkala A, Leppälä E & Wähälä K (2002) Enterolignans. J. Chromatography B, 777: 29-43.
62. Russell GB, Singh P & Fenemore PG (1976) Insect-control chemicals from plants III. Toxic lignans from Libocedrus bidwillii. J. Biol. Sci. 29: 99-103.
63. Sarker SD, Whiting P, Dinan L, Šik V & Rees HH (1999) Identification of ecdysteroid antagonist activity of three resveratrol trimers (suffruticosols A, B and C) from Paeonia suffruticosa. Tetrahedron 55: 513-524.
64. Srivastava S, Gupta MM, Prajapati V, Tripathi AK & Kumar S (2001) Sezamin a potent antifeedant principle from Piper mullesua. Phytotherapy Res. 15: 70-72.
65. Varga E, Sárik G, Hajdu Z, Szendrei K, Pelczer I & Jerkovich G (1990) Flavonoids from Leuzea carthamoides DC. Herba Hungarica 29: 51-55.
66. Vokáč K, Buděšínský M & Harmatha J (2002) Minor ecdysteroid components of Leuzea carthamoides. Collect. Czech. Chem. Commun. 67: 124-139.
67. Wada K & Munakata K (1970) (-)-Parabenzlactone, a new piperolignanolide isolated from Parabenzoin trilobum NAKAI. Tetrahedron Lett. 2017-2019.
68. Xu H, Zhang X, Tian X, Lu M & Wang YG (2002) Synthesis and insecticidal activity of novel 4 alpha-halogenated benzoylamino podophyllotoxins against Pieris rapae L. Chem. Pharm. Bull. 50: 399-402.
69. Yamashita K & Matsui M (1961) Studies on phenolic lactones. Part VI. Synergistic activities of phenolic lactones. Agric. Biol. Chem. 25: 141-143.
70. Yamauchi S & Taniguchi E (1991) Synthesis and insecticidal activity of lignan analogs (I). Agric. Biol. Chem. 55: 3075-3084.
71. Yamauchi S & Taniguchi E (1992a) Synthesis and insecticidal activity of lignan analogs (III). Biosci. Biotechnol. Biochem. 56: 418-422.
72. Yamauchi S & Taniguchi E (1992b) Synthesis and insecticidal activity of sesquilignan analogs with 2-alkyl-6-methoxy-3-(3,4-methylenedioxyphenyl)-1,4- benzodioxanyl group. Biosci. Biotechnol. Biochem. 56: 1751-1759.