The karlson lecture. phytoecdysteroids: What use are they?

Archives of Insect Biochemistry and Physiology

Volumn 72, Issue 3, 2009, Pages 126-141

  Dinan, Laurence ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Anabolic; Ecdysteroid; Gene therapy; Nutraceutical; Pest control

Indexed keywords

DRUG; ECDYSTEROID; INSECTICIDE; PLANT EXTRACT;

ANIMAL; ARTHROPOD; ARTICLE; BIOLOGICAL PEST CONTROL; CHEMISTRY; DRUG EFFECT; GENE EXPRESSION REGULATION; HUMAN; METABOLISM; PLANT;

ANIMALS; ARTHROPODS; ECDYSTEROIDS; GENE EXPRESSION REGULATION; HUMANS; INSECTICIDES; PEST CONTROL, BIOLOGICAL; PHARMACEUTICAL PREPARATIONS; PLANT EXTRACTS; PLANTS;

ARTHROPODA; MAMMALIA;

EID: 70350743206     PISSN: 07394462     EISSN: 15206327     Source Type: Journal    
DOI: 10.1002/arch.20334     Document Type: Article

References (103)

1. Badal'yants KL, Nabiev AN, Khushbaktova ZA, Syrov VN. 1996. Mechanism of hepatoprotective action of ecdystene in acute heliotrine intoxication. Dok Akad Nauk Resp Uzbek (10) 46-48.
2. Bandara BMR, Jayasinghe L, Karunaratne V, Wanningama GP, Bokel M, Kraus W. 1989. Ecdysterone from stem of Diploclisia glaucescens. Phytochem 28:1073-1075.
3. Báthori M, Tóth N, Hunyadi A, Márki A, Zádor E. 2008. Phytoecdysteroids and anabolic- androgenic steroids: structure and effects on humans. Curr Med Chem 15:75-91.
4. Bernard B, Gautier B. 2005. Use of ecdysteroids for preparing dermatological or cosmetological anti-hair loss compositions. US Patent Appl 0050137175.
5. Billas IM, Moras D. 2005. Ligand-binding pocket of the ecdysone receptor. Vitamin Hormon 73:101-129.
6. Blackford MJP, Dinan L. 1997. The effects of ingested 20-hydroxyecdysone on the larvae of Aglais urticae, Inachis io, Cynthia cardui (Lepidoptera: Nymphalidae) and Tyria jacobaeae (Lepidoptera: Arctiidae). J Insect Physiol 43:315-327.
7. Borin MR, de MB, Gottlieb OR. 1993. Steroids, taxonomic markers? Plant Syst Evol 184:41-76.
8. Calas D, Thiéry D, Marion-Poll F. 2006. 20-Hydroxyecdysone deters oviposition and larval feeding in the European grapevine moth, Lobesia botrana. J Chem Ecol 32:2443-2454.
9. Calas D, Berthier A, Marion-Poll F. 2007. Do European corn borer females detect and avoid laying eggs in the presence of 20-hydroxyecdysone? J Chem Ecol 33:1393-1404.
10. Changrakala MV, Maribashetty VG, Jyothi HK. 1998. Application of phytoecdysteroids in sericulture. Curr Sci (India) 74:341-346.
11. Chermnykh NS, Shimanovsky NL, Shutko GV, Syrov VN. 1988. Effects of methandrostenolone and ecdysterone on physical endurance of animals and protein metabolism in the skeletal muscles. Farmakol Toksikol 6:57-62.
12. Dalvit C, Flocco M, Knapp S, Mostardini M, Perego R, Stockman BJ, Veronesi M, Varasi M. 2002. High-throughput NMR-based screening with competition binding experiments. J Am Chem Soc 124:7702-7709.
13. Descoins C, Marion-Poll F. 1999. Electrophysiological responses of gustatory sensilla of Mamestra brassicae (Lepidoptera, Noctuidae) larvae to three ecdysteroids: ecdysone, 20-hydroxyecdy- sone and ponasterone A. J Insect Physiol 45:871-876.
14. Destrez B, Pinel G, Monteau F, Lafont R, Le Bizec B. 2009. Detection and identification of 20-hydroxyecdysone metabolites in calf urine by LC-HRMSn measurements and establish- ment of their kinetics of elimination after 20-hydroxyecdysone administration. Anal Chim Acta 637:178-184.
15. Dinan L. 1992. The association of phytoecdysteroids with flowering in fat hen, Chenopodium album, and other members of the Chenopodiaceae. Experientia 48:305-308.
16. Dinan L. 1995a. A strategy for the identification of ecdysteroid receptor agonists and antagonists from plants. Eur J Entomol 92:271-283.
17. Dinan L. 1995b. Distribution and levels of phytoecdysteroids within individual plants of species of the Chenopodiaceae. Eur J Entomol 92:295-300.
18. Dinan L. 1998. A strategy towards the elucidation of the contribution made by phytoecdysteroids to the deterrence of invertebrate predators on plants. Russ J Plant Physiol 45:296-305.
19. Dinan L. 2001. Phytoecdysteroids: biological aspects. Phytochemistry 57:325-339.
20. Dinan L. 2003. Ecdysteroid structure-activity relationships. In: Atta-ur-Rahman, editor. Studies in natural products chemistry, Vol. 29. New York: Elsevier. p 3-71.
21. Dinan L, Hormann RE. 2005. Ecdysteroid agonists and antagonists. In: Gilbert LI, Iatrou K, Gill SS, editors. Comprehensive molecular insect science, Vol. 3. New York: Elsevier Pergamon. p 197-242.
22. Dinan L, Lafont R. 2006. Effects and applications of arthropod steroid hormones (ecdysteroids) in mammals. J Endocrinol 191:1-8.
23. Dinan L, Whiting P, Scott A. 1998. Taxonomic distribution of phytoecdysteroids in seeds of members of the Chenopodiaceae. Biochem Syst Ecol 26:553-576.
24. Dinan L, Hormann RE, Fujimoto T. 1999. An extensive ecdysteroid CoMFA. J Comp Aid Mol Des 13:185-207.
25. Dinan L, Harmatha J, Lafont R. 2001a. Chromatographic procedures for the isolation of plant steroids. J Chromatogr A 935:105-123.
26. Dinan L, Savchenko T, Whiting P. 2001b. On the distribution of phytoecdysteroids in plants. CLMS 58:1121-1132.
27. Dinan L, Harmatha J, Volodin V, Lafont R. 2009. Phytoecdysteroids: diversity, biosynthesis and distribution. In: Smagghe G, editor. Ecdysone: structures and functions. New York: Springer Science. p 3-45.
28. El-Mofty M, Sadek I, Soliman A, Mohamed A, Sakre S. 1987. a-Ecdysone: a new bracken fern factor responsible for neoplasm induction in the Egyptian toad (Bufo regularis). Nutr Cancer 9:103-107.
29. El-Mofty MM, Sakre SA, Rizk AM, Moussa EA. 1994. Induction of breast and lung neoplastic lesions in mice by alpha-ecdysone. Oncol Rep 1:435-438.
30. Evans PD, Srivastava DP, Reale V. 2009. Rapid, non-genomic responses to ecdysteroids and catecholamines mediated by a novel Drosophila G-Protein-Coupled Receptor. In: Smagghe G, editor. Ecdysone: structures and functions. New York: Springer Science. p 425-443.
31. Fomovska GN, Berdyshev AG, Kholodova YD. 1992. Immunomodulatory effect of ecdysteroids. Ukrain Biokhim Zh 64:56-61.
32. Fukuzawa A, Kumagai Y, Masamune T, Furusaki A, Katayama C, Matsumoto T. 1981. Acetylpinnasterol and pinnasterol, ecdysone-like metabolites from the marine red alga Laurencia pinnata Yamada. Tetrahedron Lett 22:4085-4086.
33. Fukuzawa A, Miyamoto M, Kumagai Y, Masamune T. 1986. Ecdysone-like metabolites, 14a- hydroxypinnasterols from the red alga Laurencia pinnata. Phytochem 25:1305-1307.
34. Gao L, Cai G, Shi X. 2008. b-Ecdysterone induces osteogenic differentiation in mouse mesenchymal stem cells and relieves osteoporosis. Biol Pharm Bull 31:2245-2249.
35. Girault J-P. 1998. Determination of ecdysteroid structure by 1D and 2D NMR. Russ J Plant Physiol 45:306-309.
36. Gorelick-Feldman J, MacLean D, Ilic N, Poulev A, Lila MA, Cheng D, Raskin I. 2008. Phytoecdysteroids increase protein synthesis in skeletal muscle cells. J Agric Food Chem 56:3532-3537.
37. Harmatha J, Vokáč K, Kmoníčková E, Zídek Z. 2008. Lack of interference of common phytoecysteroids with production of nitric oxide by immune-activated mammalian macrophages. Steroids 73:466-471.
38. Ho R, Girault J-P, Cousteau P-Y, Bianchini J-P, Raharivelomanana P, Lafont R. 2008. Isolation of a new class of ecdysteroid conjugates (glucosyl-ferulates) using a combination of liquid chromatographic methods. J Chromatogr Sci 46:102-110.
39. Kanazawa A, Tanaka N, Kashiwada K. 1972. Nutritional requirements of prawns-IV. The dietary effect of ecdysones. Bull Jap Soc Sci Fish 38:1067-1071.
40. Kholodova YD. 2001. Phytoecdysteroids: biological effects, application in agriculture and complementary medicine. Ukr Biokhim Zh 73:21-29.
41. Kizelsztein P, Govorko D, Komarnytsky S, Evans A, Wang Z, Cefalu W, Raskin I. 2009. 20-Hydroxyecdysone decreases weight and hyperglycemia in a diet-induced obesity mice model. Am J Physiol Endocrinol Metab 296:433-439.
42. Kosar K, Opletal L, Vokac K, Harmatha J, Sovova M, Cerovsky J, Kratky F, Dvorak J. 1997. Embryotoxicity of 20-hydroxyecdysone and polypodine B from Leuzea carthamoides DC. Pharmazie 52:406-407.
43. Kosovsky MI, Syrov VN, Mirakhmedov MM, Katkova SP, Khushbaktova ZA. 1989. The effect of nerobol and ecdysterone on processes related to insulin regulatory function in normal and in experimental insulin resistance. Probl Endokrinol 35:77-81.
44. Koudela K, Tenora J, Bajer J, Mathova A, Slama K. 1995. Stimulation of growth and development in Japanese quails after oral administration of ecdysteroid-containing diet. Eur J Entomol 92:349-354.
45. Kovganko NV. 1999. Ecdysteroids and related compounds in fungi. Chem Nat Compd 35(6): 597-611 [in English]/Khim Prirod Soedin (6) 691-712 [in Russian].
46. Kratky F, Opletal L, Hejhalek J, Kucharova S. 1997. Effects of 20-hydroxyecdysone on the protein synthesis of pigs. Zivocisna Vyroba 42:445-451.
47. Kren J, Opletal L, Sovova M. 1992. The green tea preparation ''maralan'' from Leuzea carthamoides. In: Opletal L, editor. Proceedings of the CADISCO (Section A). Pharmaceu- tical Faculty of KU Hradec Králové. p 112-113.
48. Kumar MB, Fujimoto T, Potter DW, Deng Q, Palli SR. 2002. A single point mutation in ecdysone receptor leads to increased ligand specificity: implications for gene switch applications. Pros Natl Acad Sci USA 99:14710-14715.
49. Kurmukov AG, Syrov VN. 1988. Anti-inflammatory properties of ecdysterone. Med Zh Uzbek (10) 68-70.
50. Kutepova TA, Syrov VN, Khushbaktova ZA, Saatov Z. 2001. Hypoglycemic activity of the total ecdysteroid extract from Ajuga turkestanica. Pharm Chem J 35:608-609.
51. Lafont R. 1998. Phytoecdysteroids in the world flora: diversity, distribution, biosynthesis and evolution. Russ J Plant Physiol 45:276-295.
52. Lafont R, Dinan L. 2003. Practical uses for ecdysteroids in mammals including humans: an update. J Insect Sci 3.7. http://www.insectscience.org/3.7/.
53. Lafont R, Dinan L. 2009. Innovative and future applications for ecdysteroids. In: Smagghe G, editor. Ecdysone: structures and functions. New York: Springer Science. p 551-578.
54. Lafont R, Harmatha J, Marion-Poll F, Dinan L, Wilson ID. 2002. Ecdybase, a free ecdysteroid database. http://ecdybase.org.
55. Lapenna S, Friz J, Barlow A, Palli R, Dinan L, Hormann RE. 2008. Ecdysteroid ligand-receptor selectivity: exploring trends to design orthogonal gene switches. FEBS J 275:5785-5809.
56. Lapenna S, Dinan L, Friz J, Hopfinger A, Liu J, Hormann RE. 2009. Ecdysteroids as gene-switch actuators: SAR and enhancement of physicochemical properties. Chem Med Chem 4:55-68.
57. Le Bizec B, Antignac J-P, Monteau F, Andre F. 2002. Ecdysteroids: one potential new anabolic family in breeding animals. Anal Chim Acta 473:89-97.
58. Liktor-Busa E, Simon A, Tóth G, Báthori M. 2008. The first two ecdysteroids containing a furan ring from Serratula wolfii. Tetrahedron Lett 49:1738-1740.
59. Lupien PJ, Hinse C, Chaudhary KD. 1969. Ecdysone as a hypocholesterolemic agent. Arch Int Physiol Biochim 77:206-212.
60. Mamadalieva NZ, Egamberdiyeva D, Lafont R, Syrov VN, Girault J-P. 2008. Polar ecdysteroids and biological activity of the total ecdysteroids from the plant Silene viridiflora. Poster presentation at the 17th Ecdysone Workshop, Ulm, Germany, 20-24 July.
61. Marion-Poll F, Descoins C. 2002. Taste detection of phytoecdysteroids in larvae of Bombyx mori, Spodoptera littoralis and Ostrinia nubilalis. J Insect Physiol 48:467-476.
62. Mayer M, Meyer B. 2001. Group epitope mapping by saturation transfer difference NMR to identify segments of a ligand in direct contact with a protein receptor. J Am Chem Soc 123:6108-6117.
63. Meybeck A, Yang C-R. 2007. Use of compositions containing an ecdysteroid for protection against UV radiation. Patent No. WO 2007060302.
64. Nakanishi K. 2006. Studies in microbial and insect natural products chemistry. J Nat Med 60:2-20.
65. Ohsawa T, Yukawa M, Takao C, Murayama M, Bando H. 1992. Studies on constituents of fruit body of Polyporus umbellatus and their cytotoxic activity. Chem Pharm Bull 40: 143-147.
66. Okui S, Otaka T, Uchiyama M, Takemoto T, Hikino H, Ogawa S, Nishimoto N. 1968. Stimulation of protein synthesis in mouse liver by insect-moulting steroids. Chem Pharm Bull 16:384-387.
67. Otaka T, Uchiyama M, Okui S, Takemoto T, Hikino H, Ogawa S, Nishimoto N. 1968. Stimulatory effect of insect metamorphosing steroids from Achyranthes and Cyathula on protein synthesis in mouse liver. Chem Pharm Bull 16:2426-2429.
68. Palli SR, Hormann RE, Schlattner U, Lezzi M. 2005a. Ecdysteroid receptors and their applications in agriculture and medicine. Vitamin Hormon 73:59-100.
69. Palli SR, Tice CM, Margam VM, Clark AM. 2005b. Biochemical mode of action and differential activity of new ecdysone agonists against mosquitoes and moths. Arch Insect Biochem Physiol 58:234-242.
70. Panguluri SK, Li B, Hormann RE, Palli SR. 2007. Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells. FEBS J 274:5669-5689.
71. Prabhu VKK, Nayar KK. 1974. Crustecdysone is without estrogenic or antiestrogenic activity in the rat. Experientia 30:821.
72. Purser DB, Baker SK. 1994. Ecdysones used to improve productivity of ruminants. PCT Int Appl WO 94 18,984 AU Appl 93/7,397 (Chem Abs 121:254587).
73. Sakhibov AD, Syrov VN, Usmanova AS, Abakumova OY. 1989. Experimental analysis of the immunotropic action of phytoecdysteroids. Dok Akad Nauk Uzbek SSR (8) 55-57.
74. Sautour M, Canon F, Miyamoto T, Dongmo A, Lacaille-Dubois M-A. 2008. A new ecdysteroid and other constituents from two Dioscorea species. Biochem System Ecol 36:559-563.
75. Sláma K, Lafont R. 1995. Insect hormones: ecdysteroids: their presence and actions in vertebrates. Eur J Entomol 92:355-377.
76. Sláma K, Koudela K, Tenora J, Mathova A. 1996. Insect hormones in vertebrates: anabolic effects of 20-hydroxyecdysone in Japanese quails. Experientia 52:702-706.
77. Smith HC, Cavanaugh CK, Friz JL, Thompson CS, Saggers JA, Michelotti EL, Garcia J, Tice CM. 2003. Synthesis and SAR of cis-1-benzoyl-1,2,3,4-tetrahydroquinoline ligands for control of gene expression in ecdysone responsive systems. Bioorg Med Chem Lett 13:1943-1946.
78. Stopka P, Stancl J, Sláma K. 1999. Effect of insect hormone, 20-hydroxyecdysone, on growth and reproduction in mice. Acta Soc Zool Bohem 63:367-378.
79. Sun Y, Yasukawa K. 2008. New anti-inflammatory ergostane-type ecdysteroids from the sclerotium of Polyporus umbellatus. Bioorg Med Chem Lett 18:3417-3420.
80. Syrov VN, Aizikov MI, Kurmukov AG. 1975. Effect of ecdysterone on the content of protein, glycogen and fat in white rat liver, heart and muscle. Dok Akad Nauk Uzbek SSR (8) 37-38.
81. Syrov VN, Mel'nikova EV, Sultanov MB. 1981. Effects of the phytoecdysteroid ecdysterone on the course of heliotrine-induced toxic hepatitis in rats. Dok Akad Nauk Uzbek SSR (5) 36-38.
82. Syrov VN, Khushbaktova ZA, Abzalova MK, Sultanov MB. 1983. On the hypolipidemic and antiatherosclerotic action of phytoecdysteroids. Dok Akad Nauk Uzbek SSR (9) 44-45.
83. Syrov VN, Matveev SB, Kurmukov AG, Islambekov US. 1986a. Effect of ecdysterone and nerobol on the healing of experimental bone fractures. Med Zh Uzbek (3) 67-69.
84. Syrov VN, Nabiev AN, Sultanov MB. 1986b. The effect of phytoecdysteroids on the bile secretion function of the liver in normal rat and animals with experimental hepatitis. Farmakol Toksikol 49:100-103.
85. Syrov VN, Khushbaktova ZA, Nabiev AN. 1992. An experimental study of the hepatoprotective properties of phytoecdysteroids and nerobol in carbon tetrachloride-induced liver injury. Eksp Klin Farmakol 55:61-65.
86. Syrov VN, Khushbaktova ZA, Tashmukhamedova MA. 1997. Hypoglycemic action of phytoecdysteroids and some aspects of its mechanism of realization in experimental animals. Dok Akad Nauk Resp Uzbek (4) 46-49.
87. Taava VS, Palli SR, Dinkins RD, Collins GB. 2007. Applications of EcR gene switch technology in functional genomics. Arch Insect Biochem Physiol 65:164-179.
88. Taava VS, Dinkins RD, Collins GB, Palli SR. 2009. Ecdysone receptor-based gene switches for applications in plants. In: Smagghe G, editor. Ecdysone: structures and functions. New York: Springer Science. p 511-538.
89. Takahashi H, Nishimoto K. 1992. Antidiabetic agents containing ecdysterone or inokosterone. Jpn Kokai Tokkyo Koho JP 04,125,135 [92 124,135] (Chem Abs 117:84874b).
90. Takasaki M, Tokuda H, Nishino H, Konoshima T. 1999. Cancer chemopreventative agents (antitumor-promoters) from Ajuga decumbens. J Nat Prod 62:972-975.
91. Taniguchi SF, Bersani-Amado CA, Sudo LS, Assel SMC, Oga S. 1997. Effect of Pfaffia iresinoides on the experimental inflammatory process in rats. Phytother Res 11:568-571.
92. Tice CM, Hormann RE, Thompson CS, Friz JL, Cavanaugh CK, Michelotti EL, Garcia J, Nicolasc E, Albericio F. 2003a. Synthesis and SAR of á-acylaminoketone ligands for control of gene expression. Bioorg Med Chem Lett 13:475-478.
93. Tice CM, Hormann RE, Thompson CS, Friz JL, Cavanaugh CK, Saggers JA. 2003b. Optimization of a-acylaminoketone ecdysone agonists for control of gene expression. Bioorg Med Chem Lett 13:1883-1886.
94. Tomaschko KH. 1999. Nongenomic effects of ecdysteroids. Arch Insect Biochem Physiol 41:89-98.
95. Tóth N, Szabó A, Kacsala P, Héger J, Zádor E. 2008. 20-Hydroxyecdysone increases fiber size in a muscle-specific fashion in rat. Phytomedicine 15:691-698.
96. Trenin DS, Volodin VV. 1999. 20-Hydroxyecdysone as a human lymphocyte and neutrophil modulator: in vitro evaluation. Arch Insect Biochem Physiol 41:156-161.
97. Uchiyama M, Yoshida T. 1974. Effect of ecdysterone on carbohydrate and lipid metabolis. In: Burdette WJ, editor. Invertebrate endocrinology and hormonal heterophylly. Berlin: Springer Verlag. p 375-398.
98. Volodin V, Chadin I, Whiting P, Dinan L. 2002. Screening of plants of European North-East Russia for ecdysteroids. Biochem Syst Ecol 30:525-578.
99. Wessner M, Champion B, Girault J-P, Kaouadji N, Saidi B, Lafont R. 1992. Ecdysteroids from Ajuga iva. Phytochem 31:3785-3788.
100. Wilborn CD, Taylor LW, Capbell WI, Kerksick C, Rasmussen CJ, Greenwood M, Kreider RB. 2006. Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males. J Int Soc Sports Nutr 3:19-27.
101. Yoshida T, Otaka T, Uchiyama M, Ogawa S. 1971. Effect of ecdysterone on hyperglycemia in experimental animals. Biochem Pharmacol 20:3263-3268.
102. Zibareva LN. 1997. The prognosis of the presence of ecdysteroids among the species Silene L. and Chenopodium L. to their contents in the seeds. Rast Resur 33:89-92.
103. Zibareva L, Volodin V, Saatov Z, Savchenko T, Whiting P, Lafont R, Dinan L. 2003. Distribution of phytoecdysteroids in the Caryophyllaceae. Phytochem 64:499-517.