Phytogrowth- and photosynthesis-inhibiting properties of nostoclide analogues

Pest Management Science

Volumn 62, Issue 3, 2006, Pages 214-222

  Barbosa, Luiz C A ^a   Demuner, Antônio J ^a   De Alvarenga, Elson S ^a   Oliveira, Alberto ^a   King Diaz, Beatriz ^b   Lotina Hennsen, Blas ^b  

^a FEDERAL UNIVERSITY OF VIÇOSA   (Brazil)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

lactones; Nostoclide; Photosynthesis inhibitors; Plant growth inhibitor

Indexed keywords

ADENOSINE TRIPHOSPHATASE (CALCIUM MAGNESIUM); DRUG DERIVATIVE; GAMMA BUTYROLACTONE; HERBICIDE; NOSTOCLIDE I; NOSTOCLIDE II;

INHIBITOR; PHYTOTOXICITY;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CHLOROPLAST; DRUG EFFECT; GERMINATION; GROWTH, DEVELOPMENT AND AGING; LOLIUM; METABOLISM; PHOTOSYNTHESIS; PHYSALIS; PLANT ROOT; SPINACH; SYNTHESIS;

4-BUTYROLACTONE; CA(2+) MG(2+)-ATPASE; CHLOROPLASTS; GERMINATION; HERBICIDES; LOLIUM; MOLECULAR STRUCTURE; PHOTOSYNTHESIS; PHYSALIS; PLANT ROOTS; SPINACIA OLERACEA;

LOLIUM; LOLIUM MULTIFLORUM; PHYSALIS; PHYSALIS PHILADELPHICA IMMACULATA;

EID: 33644970628     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1147     Document Type: Article

References (34)

1. Heap IM, The occurrence of herbicide-resistant weeds worldwide. Pestic Sci 51:235-243 (1997).
2. Reigosa M and Pedrol N, Allelopathy. Science Publishers, Plymouth (2002).
3. Copping LG, Crop Protection Agents from Nature. Royal Society of Chemistry, Cambridge (1996).
4. Godfrey CRA, Agrochemicals from Natural Products. Marcel Dekker, New York (1994).
5. Vyvyan JR, Allelochemicals as leads for new herbicides and agrochemicals. Tetrahedron 58:1631-1646 (2002).
6. Haga Y, Okazaki M and Shuto Y, Systematic strategy for the synthesis of cyanobacterin and its stereoisomers. 1. Asymmetric total synthesis of dechloro-cyanobacterin and its enantiomer. Biosci Biotechnol Biochem 67:2183-2193 (2003).
7. Pignatello JJ, Porwooll J, Carlson RE, Xavier A and Gleason FK, Structure of the antibiotic cyanobacterin, a chlorine-containing γ-lactone from the freshwater cyanobacterium Scytonema hofmanni. J Org Chem 48:4035-4038 (1983).
8. Gleason FK and Baxa CA, Activity of the natural algicide, cyanobacterin, on eukaryotic microorganisms. FEMS Microbiol Lett 33:85-88 (1986).
9. Gleason FK and Case DE, Activity of the natural algicide, cyanobacterin, on angiosperma. Plant Physiol 80:834-838 (1986).
10. Gleason FK and Paulson JL, Site of action of the natural algicide, cyanobacterin, in the blue-green alga, Synechococcus sp. Arch Microbiol 138:273-277 (1984).
11. Gleason FK, The natural herbicide, cyanobacterin, specifically disrupts thylakoid membrane structure in Euglena gracilis strain Z. FEMS Microbiol Lett 68:77-82 (1990).
12. Yang X and Shimizu Y, Nostoclide I and II, extracellular metabolites from a symbiotic cyanobacterium, Nostoc sp., from the lichen Peltigera canina. Tetrahedron Lett 34:761-764 (1993).
13. Barbosa LCA, Demuner AJ, Borges EEL and Mann J, Synthesis and evaluation of the plant growth regulatory activity of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives. J Braz Chem Soc 8:19-27 (1997).
14. Barbosa LCA, Demuner AJ, Maltha CRA, Silva PS and Silva AA, Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico. Quím Nova 26:655-660 (2003).
15. Demuner AJ, Barbosa LCA and Veloso DP, New 8-oxabicyclo [3.2.1]oct-6-en-3-one derivatives with plant growth regulatory activity. J Agric Food Chem 46:1173-1176 (1998).
16. Jimenez A, Mata R, Lotina-Hennsen B and Anaya AL, Interference of 1,2,3,4-tetramethoxy-5-(2-propenyl)benzene with photosynthetic electron transport. Z Naturforsch 53c:55-59 (1998).
17. Lima LS, Barbosa LCA, Alvarenga ES, Demuner AJ and Silva AA, Synthesis and phytotoxicity evaluation of substituted para-benzoquinones. Aust J Chem 56:625-630 (2003).
18. Perrin DD and Armarego WLF, Purification of Laboratory Chemicals (3rd edn). Pergamon, Oxford (1988).
19. Boukouvalas J, Maltais F and Lachance L, Furanolate-based strategy for sequential 2,3,4-trisubstitution of butenolide: total synthesis of nostoclides I and II. Tetrahedron Lett 35:7897-7900 (1994).
20. Mancuso AJ, Huang SL and Swern D, Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide 'activated' by oxalyl chloride. J Org Chem 43:2480-2482 (1978).
21. Macías FA, Galindo JCG, Castellano D and Velasco RF, Sesquiterpene lactones with potential use as natural herbicide models. 2. Guaianolides. J Agric Food Chem 48:5288-5296 (2000).
22. González-Bernardo E, Aguilar MI, Delgado G, King-Díaz B and Lotina-Hennsen B, Photosynthetic electron transport interaction of xanthorrhizol isolated from Iostephane heterophylla and its derivatives. Physiol Plant 119:598-604 (2003).
23. Mills JD, Mitchell P and Schurmann P, Modulation of coupling ATPase activity in intact chloroplasts. FEBS Lett 112:173-177 (1980).
24. Hernandez-Terrones MG, Aguilar MI, King-Diaz B and Lotina-Hennsen B, Inhibition of photosystem II in spinach chloroplasts by trachyloban-19-oic acid. Pestic Biochem Physiol 77:12-17 (2003).
25. Strain HH, Cope TR and Svec MA, Analytical procedures for the isolation, identification, estimation and investigation of the chlorophylls. Methods Enzymol 23:452-476 (1971).
26. 2+-exchange phenomena. Methods Enzymol 24:68-74 (1971).
27. Izawa S and Pan RL, Photosystem I electron transport and phosphorylation supported by electron donation to the plastoquinone region. Biochem Biophys Res Commun 83:1171-1177 (1978).
28. 3+ on redox enzymes of spinach thylakoids. J Agric Food Chem 47:3075-3080 (1999).
29. Sumner JB, Scientific apparatus and laboratory methods. A method for the colorimetric determination of phosphorus. Science (Washington) 100:413-418 (1944).
30. 2-synthon to 2-substituted butenolides. Tetrahedron Lett 27:1391-1394 (1986).
31. Boukouvalas J, Lachance N, Ouellet M and Trudeu M, Facile access 4-aryl-2(5H)-furanones by Suzuki cross coupling: efficient synthesis of rubrolides C and E. Tetrahedron Lett 39:7665-7668 (1998).
32. Izawa S and Good NE, Inhibition of photosynthetic electron transport and photophosphorylation. Methods Enzymol 24:355-377 (1972).
33. Allen JF and Holmes NG, Electron transport and redox titration, in Photosynthesis, Energy Transduction: a Practical Approach, ed. by Hopkins MF and Baker NR. IRL Press, Oxford, pp. 103-141 (1986).
34. King-Díaz B, Esquivel B, Terrones MH and Lotina-Hennsen B, Metabolitos secundários de plantas mexicanas como posibles agentes herbicidas, in Avances en Bioquímica y Biología Molecular de Plantas, ed. by Lugo IB and Tavera HL. UNAM Press, México DF, pp. 111-134 (2001).