Ecdysteroids and bufadienolides from Helleborus torquatus (Ranunculaceae)

Phytochemistry

Volumn 57, Issue 3, 2001, Pages 401-407

  Meng, Yanhui ^a   Whiting, Pensri ^a   Šik, Vladimir ^a   Rees, Huw H ^b   Dinan, Laurence ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Bioassay; Bufadienolides; Ecdysteroid; Hellebortin A (5 D glucopyranosyloxy 10, 14, 16 trihydroxy 19nor 5 , 10 , 14 , 16 bufa 3, 20, 22 trienolide 1 ); Hellebortin B (5 D glucopyranosyloxy 3, 4 epoxy 14 hydroxy 19 oxo bufa 20, 22 dienolide 2 ); Hellebortin C (5 D glucopyranosyloxy 3, 4 epoxy 10, 14 dihydroxy 19 nor bufa 20, 22 dienolide 3 ); Helleborus torquatus; Ranunculaceae

Indexed keywords

20 HYDROXYECDYSONE 3 O BETA GLUCOSIDE; BUFADIENOLIDE DERIVATIVE; ECDYSTEROID; ECDYSTEROIDS; ECDYSTERONE; HELLEBORTIN A; HELLEBORTIN B; HELLEBORTIN C; HELLEBORUS TORQUATUS EXTRACT; HYDROLASE; INSECTICIDE; PLANT EXTRACT; STEROID; UNCLASSIFIED DRUG;

ANGIOSPERM; ANIMAL; ARTICLE; BIOASSAY; BIOLOGICAL PEST CONTROL; CELL LINE; CELL SURVIVAL; CHEMICAL STRUCTURE; CONFORMATION; DROSOPHILA MELANOGASTER; HELIX (SNAIL); HELLEBORUS TORQUATUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PLANT; PLANT SEED; STEREOCHEMISTRY;

ANGIOSPERMS; ANIMALS; BIOLOGICAL ASSAY; BUFANOLIDES; CELL LINE; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DROSOPHILA MELANOGASTER; ECDYSTEROIDS; HELIX (SNAILS); HYDROLASES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SEEDS; STEROIDS;

EID: 0035371924     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(01)00070-X     Document Type: Article

References (21)

1. Agrawal P.K. NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry. 31:1992;3307-3330.
2. Akizawa T., Mukai T., Matsukawa M., Yoshioka M., Morris J.F., Butler V.P. Structures of novel bufadienolides in the eggs of toad, Bufo marinus. Chem. Pharm. Bull. 42:1994;745-756.
3. Aitzetmüller K., Tseveguren N., Werner G. Seed oil fatty acid patterns of the Aconitum-Delphinium-Helleborus complex (Ranunculaceae). Plant System. Evol. 215:1999;37-47.
4. Bogdan I., Nechifor A., Basea I., Hruban E. From the Romanian traditional medicine - unspecific irratating therapy by transcutaneous implantation of Helleborus purpurascens, fam Ranunculaceae, in farm-animals. Deutsche Tierärztliche Wochenschrift. 97:1990;525-529.
5. Bussing A., Schweizer K. Effects of a phytopreparation from Helleborus niger on immunocompetent cells in vitro. J. Ethnopharm. 59:1998;139-146.
6. Colombo M.L., Tomè F., Bugatti C. Lipid-content and fatty-acid composition in hypogeous organs of Helleborus species (Ranunculaceae). Plant System. Evol. 178:1991;55-63.
7. Clément C.Y., Bradbrook D.A., Lafont R., Dinan L. Assessment of a microplate-based bioassay for the detection of ecdysteroid-like or antiecdysteroid activities. Insect. Biochem. Mol. Biol. 23:1993;187-190.
8. Dinan L. The analysis of phytoecdysteroids in single (pre-flowering stage) specimens of fat hen, Chenopodium album. Phytochem. Anal. 3:1992;132-138.
9. Dinan L. A strategy for the identification of ecdysteroid receptor agonists and antagonists from plants. Eur. J. Entomol. 92:1995;271-283.
10. Dinan L., Hormann R.E., Fujimoto T. A extensive ecdysteroid CoMFA. J. Computer-aided Mol. Design. 13:1999;185-207.
11. Dinan L., Savchenko T., Whiting P., Sarker S.D. Plant natural products as insect steroid receptor agonists and antagonists. Pestic. Sci. 55:1999;331-335.
12. Hardman R., Benjamin T.V. The co-occurrence of ecdysones with bufadienolides and steroidal saponins in the genus Helleborus. Phytochemistry. 15:1976;1515-1516.
13. Holliman A., Milton D. Helleborus foetidus poisoning of cattle. Veterinary Record. 127:1990;339-340.
14. Kissmer B., Wichtl M. Ecdysteroids from roots and seeds of Helleborus species. Archiv. Pharm. 320:1987;541-546.
15. Lafont R., Wilson I. The Ecdysone Handbook. 2nd Edition:1996;The Chromatographic Society, Nottingham.
16. Liedtke S., Lorch E., Goedings P., Wichtl M. Isolation of beta-ecdysone and macranthoside I from roots of Helleborus niger subsp. niger (Ranunculaceae). Pharmazie. 52:1997;964-965.
17. Muhr P., Kerek F., Dreveny D., Likussar W., Schubertzsilavecz M. The structure of hellebrin. Liebigs Annalen Organ. Bioorgan. Chem. 2:1995;443-444.
18. Pascual-Villalobos M.J., Robledo A. Screening for anti-insect activity in Mediterranean plants. Indust. Crops Prod. 8:1998;183-194.
19. Steyn P.S., Van Heerden F.R. Bufadienolides of plant and animal origin. Nat. Prod. Reports. 15:1998;397-413.
20. Vladimirov S.M., Zivanovstakic D.S., Ribar B.J. A steroidal sapogenin from Helleborus multifidus subsp. serbicus. Phytochemistry. 30:1991;1724-1725.
21. Yamagishi T., Yan X.-Z., Wu R.-Y., McPhail A.R., McPhail A.T., Lee K.-H. Structure and stereochemistry of bryophyllin-A, a novel potent cytotoxic bufadienolide orthoacetate from Bryophyllum pinnatum. Chem. Pharm. Bull. 36:1988;1615-1617.