Structural diversity and defensive properties of diterpenoid alkaloids

Phytochemistry Reviews

Volumn 6, Issue 1, 2007, Pages 81-95

  Reina, Matías ^a   González Coloma, Azucena ^b  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b INSTITUTO DE CIENCIAS AGRARIAS   (Spain)

Author keywords

Aconitum; Antiparasitic activity; Consolida; Cytotoxic; Delphinium; Diterpenoid alkaloids; Insecticidal; Structure activity relationships

Indexed keywords

1,14 DIACETYLCARDIOPETALINE; 1,4 O ACETYLCARDIOPETALIDINA; 13 OXOCARDIOPENTAMINE; 14 DEACETYLAJADINE; 14 O ACETYLDELECTININE; 15,22 O DIACETYL 19 OXODIHYDROATISINE; 18 HYDROXY 14 O METHYLGADESINE; 19 OXODIHYDROATISINE; 3 ACETYLACONITINE; 8 O ETHYL 14 BENZOYLACONINE; 8 O ETHYLACONINE; 8 O METHYLCOLUMBIANINE; 8 O METHYLCONSOLARINE; 8 O METHYLKARAKOLINE; ACONITINE; AJADELPHININE; ALKALOID; ATISINIUM CHLORIDE; AZITINE; CARDIOPETALIDINE; CARDIOPETALINE; DEHYDROTAKAOSAMINE; DELPHIGRACILINE; DITERPENOID; ISOAZITINE; KARAKOLINE; LYCOCTONINE; NEOLINE; PUBESCENINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACONITUM; ANTINEOPLASTIC ACTIVITY; ARMYWORM; COLORADO POTATO BEETLE; CONFERENCE PAPER; CYTOTOXICITY; EPIMASTIGOTE; HOST CELL; HUMAN; INSECTICIDAL ACTIVITY; LARKSPUR; MULTIDRUG RESISTANCE; NONHUMAN; PARASITOSIS; PRIORITY JOURNAL; PROMASTIGOTE;

ACONITUM; CONSOLIDA; DELPHINIUM; HEXAPODA; LEISHMANIA INFANTUM; LEPTINOTARSA DECEMLINEATA; SPODOPTERA LITTORALIS;

EID: 33947372044     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-006-9013-5     Document Type: Conference Paper

References (37)

1. Ameri A (1998) The effects of aconitum alkaloids on the central nervous system. Prog Neurobiol 56:211-235
2. Atta-ur-Rahman M, Choudary MI (1999) Diterpenoid and steroidal alkaloids. Nat Prod Rep 16:619
3. Bessonova IA, Shaidkhodzaeva SA (2000) Hetisane-type diterpene alkaloids. Chem Nat Comp 36:419-477
4. Bloomquist JR (2001) GABA and glutamate receptors as biochemical sites for insecticide action. In: Ishaaya I (ed) Biochemical sites of insecticide action and resistance. Springer-Verlag, Berlin
5. Cohen RW, Mahoney DA, Can HD (2002) Possible regulation of feeding behavior in cockroach nymphs by the neurotransmitter octopamine. J Insect Behav 15:37-50
6. De la Fuente G, Reina M (1990) Some phytochemical studies of the genera Aconitum, L. Delphinium L. and Consolida (DC) S. F. Gray. Collect Bot (Barcelona) 19:129-140
7. De Inés C, Reina M, Gavín JA, González-Coloma A (2006) In vitro cytotoxicity of norditerpenoid alkaloids. Z Naturforsch 61C:11-18
8. Dobelis P, Madl JE, Pfister JA, Manners GD, Walrond JP (1999) Effects of Delphinium alkaloids on neuromuscular transmission. J Pharm Exp Ther 291:538-546
9. Dzhakhangirov FN, Sultankhodzhaev MN, Tashkhodzhaev B, Salimos BT (1997) Diterpenoid alkaloids as a new class of antiarrthythmic agents. Structure-activity relationship Chem Nat Compd 33:190-202
10. + channels, toxicity and antinoniceptive properties. Eur J Pharmacol 337:165-174
11. 20 diterpenoid alkaloid derivatives on promastigotes and intracellular amastigotes of Leishmania infantum. Int J Antimicrob Agents 25:136-141
12. González P, Marín C, Rodríguez-González I, Hitos A, Rosales MJ, Reina M, González-Coloma A, Sánchez-Moreno M (2006) Diterpenoid alkaloid derivatives as chemotherapeutic agents in American trypanosomiasis. Pharmacology 76:123-128
13. González-Coloma A, Guadaño A, Gutiérrez C, Cabrera R, De la Peña E, De la Fuente G, Reina M (1998) Antifeedant Delphinium diterpene alkaloids. Structure-activity relationships. J Agric Food Chem 46:286-290
14. González-Coloma A, Valencia F, Martín N, Hoffmann JJ, Hutter L, Marco JA, Reina M (2002) Silphinene sesquiterpenes as model insect antifeedants. J Chem Ecol 28:117-129
15. González-Coloma A, Reina M, Madinaveitia A, Guadaño A, Santana O, Martínez-Díaz R, Ruiz-Mesía L, Alva A, Grandez M, Díaz R, Gavín JA, De la Fuente G (2004a) Structural diversity and defensive properties of norditerpenoids alkaloids. J Chem Ecol 30:1393-1408
16. González-Coloma A, Reina M, Guadaño A, Martínez- Díaz R, Díaz JG, García-Rodríguez J, De la Fuente G (2004b) Antifeedant C-20 diterpene alkaloids. Chem Biodiv 1:1327-1335
17. Hardick DJ, Blagbrough IS, Cooper G, Potter BV, Critchley T, Wonnacott S (1996) Nudicauline and elatine as potent norditerpenoid ligands at rat neuronal alpha-bungarotoxin binding sites: importance of the (methylsuccinimido) benzoyl moiety for neuronal nicotinic acetylcholine receptor binding. J Med Chem 39:4860-4866
18. Heinz CA, Zagerl AR, Berenbaum M (1996) Effects of natural and synthetic neuroactive substances on the growth and feeding of cabbage looper Trichoplusia ni. Entomol Exp Appl 80:443-451
19. Jacyno JM (1996) Lycaconitine revisited: Partial synthesis and neuronal nicotinic acetylcholine receptor affinities. J Nat Prod 59:707-709
20. Jennings KR, Brown DG, Wright DPJ (1986) Methyllycaconitine, a naturally occurring insecticide with a high affinity for the insect cholinergic receptor. Experientia 42:611-613
21. Kukel CF, Jennings KR (1994) Delphinium alkaloids as inhibitors of α-bungarotoxin binding to rat and insect neural membranes. Can J Physiol Pharmacol 72:104-107
22. Li L, Shen YM, Yang XS, Zuo GY, Shen ZQ, Chen ZH, Hao XJ (2002a) Antiplatelet aggregation activity of diterpene alkaloids from Spiraea japonica. Eur J Pharmacol 449:23-28
23. Li L, Shen YM, Yang XS, Wu WL, Wang BG, Chen ZH, Hao XJ (2002b) Effects of spiramine T on antioxidant enzymatic activities and nitric oxide production in cerebral ischemia-reperfusion gerbils. Brain Res 944:205-209
24. Mullin CA, González-Coloma A, Gutiérrez C, Reina M, Eichenseer H, Hollister B, Chyb S (1997) Antifeedant effects of some novel terpenoids on Chrysomelidae beetles: comparisons with alkaloids on an alkaloid-adapted and a non-adapted species. J Chem Ecol 23:1851-1866
25. Nauen R, Ebbinghaus U, Tietjen K (1999) Ligands of the nicotinic acetylcholine receptor as insecticides. Pestic Sci 55:566-614
26. Palmer G, Horgan DJ, Tisdale H, Singer TP, Beinert H (1968) Studies of the respiratory chain-linked reduced nicotamide adenine dinucleotide dehydrogenase. XIV. Location of the sites of inhibition of rotenone, barbiturates, and piericidin by means of electron paramagnetic resonance spectroscopy. J Biol Chem 243:844-847
27. Panter KE, Manners GD, Stegelmeier BL, Gardner DR, Ralphs MH, Pfister JA, James LF (2002) Larkspur poisoning: toxicology and alkaloid structure-activity relationships. Biochem Syst Ecol 30:113-128
28. Reina M, Madinaveitia A, De la Fuente G (1997) Further norditerpenoid alkaloids from Delphinium cardiopetalum. Phytochemistry 45:1707-1711
29. Reina M, Nold M, Santana O, Orihuela JC, González-Coloma A (2002) C-5 substituted antifeedant silphinene sesquiterpenes. J Nat Prod 65:448-453
30. Reina M, Mancha R, Rodriguez ML, Martínez-Díaz RA, Bailen M, González-Coloma A (2006) Diterpenoid alkaloids from Delphinium gracile DC. Nat Prod Lett (in press)
31. Ruiz Mesia L, Madinaveitia A, Reina M, Rodriguez ML, De la Fuente G, Ruiz-Mesia W (2002) Four new alkaloids from Consolida glandulosa. J Nat Prod 65:496-499
32. Sanes JR, Prescott DJ, Hildebrand JG (1977) Cholinergic neurochemical development of normal and deafferented antennal lobes during metamorphosis of the koth Manduca sexta. Brain Res 119:389-402
33. Schiff PB, Horwitz SB (1980) Taxol stabilizes microtubules in mouse fibroblast cells. Proc Natl Acad Sci USA 77:1561-1565
34. 3H] noradrenaline uptake of the aconitum alkaloids aconitine, 3-acetylaconitine, lappaconitine, and N-desacetyllappaconitine in rat hippocampus. Biochem Pharmacol 55:883-888
35. Ulubelen A, Mericli A, Kilincer N, Ferizli AG, Emecki M, Pelletier W (2001) Insect repellent activity of diterpenoid alkaloids. Phytother Res 15:170-171
36. Wang F-P, Liang X-T (2002) In: The alkaloids, vol 59. Academic Press, San Diego, pp 1-280
37. Wink M, Schmeller T, Latz-Brüning B (1998) Modes of action of allelochemical alkaloids: interaction with neuroreceptors, DNA and other molecular targets. J Chem Ecol 24:1881-1937