F A Macias

Summary

Country: Spain

Publications

  1. ncbi request reprint Bioactive steroids from Oryza sativa L
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real Cadiz, Spain
    Steroids 71:603-8. 2006
  2. doi request reprint Characterization of three saponins from a fraction using 1D DOSY as a solvent signal suppression tool. Agabrittonosides E-F. Furostane saponins from Agave brittoniana Trel. spp. Brachypus
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real, Cadiz, Spain
    Magn Reson Chem 48:350-5. 2010
  3. ncbi request reprint Sesquiterpene lactones as allelochemicals
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, 11510 Puerto Real, Spain
    J Nat Prod 69:795-800. 2006
  4. ncbi request reprint Optimization of benzoxazinones as natural herbicide models by lipophilicity enhancement
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, C República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 54:9357-65. 2006
  5. ncbi request reprint New herbicide models from benzoxazinones: aromatic ring functionalization effects
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, Avenida República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 54:9843-51. 2006
  6. ncbi request reprint Allelopathy--a natural alternative for weed control
    Francisco A Macias
    Grupo de Alelopatia, Department of Organic Chemistry, University of Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    Pest Manag Sci 63:327-48. 2007
  7. ncbi request reprint Characterization of the fraction components using 1D TOCSY and 1D ROESY experiments. Four new spirostane saponins from Agave brittoniana Trel. spp. Brachypus
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real, Cadiz, Spain
    Magn Reson Chem 45:615-20. 2007
  8. ncbi request reprint Evolution and current status of ecological phytochemistry
    Francisco A Macias
    Grupo de Alelopatía de Cádiz GAC, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, 11510 Puerto Real Cadiz, Spain
    Phytochemistry 68:2917-36. 2007
  9. ncbi request reprint Helikauranoside a, a new bioactive diterpene
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510, Puerto Real, Cadiz, Spain
    J Chem Ecol 34:65-9. 2008
  10. doi request reprint Bioactive apocarotenoids from Tectona grandis
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real Cadiz, Spain
    Phytochemistry 69:2708-15. 2008

Collaborators

Detail Information

Publications43

  1. ncbi request reprint Bioactive steroids from Oryza sativa L
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real Cadiz, Spain
    Steroids 71:603-8. 2006
    ..In the case of ergosterol peroxide the activity was higher than the commercial herbicide Logran. This is the first report of potential allelopathic activity of steroids on weeds based on their phytotoxicity...
  2. doi request reprint Characterization of three saponins from a fraction using 1D DOSY as a solvent signal suppression tool. Agabrittonosides E-F. Furostane saponins from Agave brittoniana Trel. spp. Brachypus
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real, Cadiz, Spain
    Magn Reson Chem 48:350-5. 2010
    ..In addition, the methoxylation of these furostane saponins in the presence of MeOH was studied...
  3. ncbi request reprint Sesquiterpene lactones as allelochemicals
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, 11510 Puerto Real, Spain
    J Nat Prod 69:795-800. 2006
    ..The most phytotoxic compounds were helivypolide F and 15-hydroxy-3-dehydrodeoxyfruticin, both of which have a carbonyl group at C-3 conjugated with two double bonds...
  4. ncbi request reprint Optimization of benzoxazinones as natural herbicide models by lipophilicity enhancement
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, C República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 54:9357-65. 2006
    ..Because optimal lipophilicity values for phytotoxicity vary with the tested plant, these new derivatives constitute a more selective way to take advantage of benzoxazinone phytotoxic capabilities...
  5. ncbi request reprint New herbicide models from benzoxazinones: aromatic ring functionalization effects
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, Avenida República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 54:9843-51. 2006
    ..and Avena fatua L.) were compared by means of a proposed selectivity index, which displayed 7F-D-DIBOA as the most selective of the tested benzoxazinones...
  6. ncbi request reprint Allelopathy--a natural alternative for weed control
    Francisco A Macias
    Grupo de Alelopatia, Department of Organic Chemistry, University of Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    Pest Manag Sci 63:327-48. 2007
    ....
  7. ncbi request reprint Characterization of the fraction components using 1D TOCSY and 1D ROESY experiments. Four new spirostane saponins from Agave brittoniana Trel. spp. Brachypus
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real, Cadiz, Spain
    Magn Reson Chem 45:615-20. 2007
    ..Moreover, the work represents a new approach to structural elucidation of saponins in refined fractions by NMR investigations...
  8. ncbi request reprint Evolution and current status of ecological phytochemistry
    Francisco A Macias
    Grupo de Alelopatía de Cádiz GAC, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, 11510 Puerto Real Cadiz, Spain
    Phytochemistry 68:2917-36. 2007
    ..Some final remarks are made to summarize our opinion about the immediate future of phytochemical ecology and phytochemical studies...
  9. ncbi request reprint Helikauranoside a, a new bioactive diterpene
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510, Puerto Real, Cadiz, Spain
    J Chem Ecol 34:65-9. 2008
    ..Helikauranoside A (4) was the most active (-84%, 10(-3)M; -56%, 10(-4)M). These results suggest that this new compound may be involved in defense mechanisms of H. annuus...
  10. doi request reprint Bioactive apocarotenoids from Tectona grandis
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real Cadiz, Spain
    Phytochemistry 69:2708-15. 2008
    ..Those compounds that presented higher levels of activity were assayed on standard target species (Lactuca sativa, Lycopersicum esculentum, Lepidium sativum and Allium cepa)...
  11. doi request reprint Modified benzoxazinones in the system Oryza sativa-Echinochloa crus-galli: an approach to the development of biorational herbicide models
    Francisco A Macias
    Allelopathy Group, Department of Organic Chemistry, University of Cadiz, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 56:9941-8. 2008
    ..These results confirm the potential of D-DIBOA as a lead herbicide for the control of Echinochloa spp. in rice crops...
  12. doi request reprint Megalanthine, a bioactive sesquiterpenoid from Heliotropium megalanthum, its degradation products and their bioactivities
    Francisco A Macias
    Departamento de Quimica Organica, Universidad de Cadiz, Puerto Real, Spain
    J Chem Ecol 35:39-49. 2009
    ..The positive results recorded in the antifungal and antifeedant tests suggest, however, that this chemical is relevant in several ecological interactions involving H. megalanthum...
  13. doi request reprint Multifunctionalised benzoxazinones in the systems Oryza sativa-Echinochloa crus-galli and Triticum aestivum-Avena fatua as natural-product-based herbicide leads
    Francisco A Macias
    Department of Organic Chemistry, University of Cadiz, Puerto Real, Cadiz, Spain
    Pest Manag Sci 66:1137-47. 2010
    ..An evaluation of the bioactivity of these compounds on the systems Oryza sativa-Echinochloa crus-galli and Triticum aestivum-Avena fatua is reported here...
  14. doi request reprint New chemical clues for broomrape-sunflower host-parasite interactions: synthesis of guaianestrigolactones
    Francisco A Macias
    Grupo de Alelopatia, Depto de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Puerto Real, Cadiz, Spain
    J Agric Food Chem 57:5853-64. 2009
    ..We have named this new class of compounds guaianestrigolactones (GELs)...
  15. doi request reprint Aromatic-ring-functionalised benzoxazinones in the system Oryza sativa-Echinochloa crus-galli as biorational herbicide models
    Francisco A Macias
    Allelopathy Group, Department of Organic Chemistry, University of Cadiz, Avda Republica Saharaui, S N, 11510 Puerto Real, Cadiz, Spain
    Pest Manag Sci 65:1104-13. 2009
    ..This emphasises the need for alternative treatments in which herbicidal compounds from a natural origin could be included...
  16. ncbi request reprint Rediscovering the bioactivity and ecological role of 1,4-benzoxazinones
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, Avda Repiúlica Saharaui, s n 11510 Puerto Real, Cadiz, Spain
    Nat Prod Rep 26:478-89. 2009
    ..The versatility of the benzoxazinone skeleton, in addition to its relative chemical simplicity and accessibility, makes these chemicals amongst the most promising sources of bioactive compounds that are natural in origin...
  17. doi request reprint Combined strategy for phytotoxicity enhancement of benzoxazinones
    Francisco A Macias
    Allelopathy Group, Department of Organic Chemistry, University of Cadiz, Avda Republica Saharaui, s n 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 58:2047-53. 2010
    ..These results support our previous research and conclusions regarding the steric, electronic, and solubility requirements to achieve the maximum phytotoxic activity...
  18. doi request reprint Isolation and phytotoxicity of terpenes from Tectona grandis
    Francisco A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Puerto Real, Cadiz, Spain
    J Chem Ecol 36:396-404. 2010
    ..The compounds that presented the highest phytotoxic activity are the diterpenes 9 (2-oxokovalenic acid) and 12 (19-hydroxyferruginol)...
  19. ncbi request reprint Structure-activity relationship (SAR) studies of benzoxazinones, their degradation products, and analogues. Phytotoxicity on problematic weeds Avena fatua L. and Lolium rigidum Gaud
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, 11510 Puerto Real, Spain
    J Agric Food Chem 54:1040-8. 2006
    ..The bioactivity of aminophenoxazines has been correlated by their aqueous solubility-lipophilicity predicted by means of computational methods...
  20. ncbi request reprint Isolation and synthesis of allelochemicals from gramineae: benzoxazinones and related compounds
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, 11510 Puerto Real Cadiz, Spain
    J Agric Food Chem 54:991-1000. 2006
    ..All of the methodologies employed allowed the desired compounds to be obtained in high yield and in an easy-to-scale manner...
  21. ncbi request reprint Bioactive carotanes from Trichoderma virens
    F A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    J Nat Prod 63:1197-200. 2000
    ..The trichocaranes significantly inhibited the growth of etiolated wheat coleoptiles: 40% at 10(-4) M with 1 and 2 and 86% at 10(-3) M with 3...
  22. ncbi request reprint Sesquiterpene lactones with potential use as natural herbicide models. 2. guaianolides
    F A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 48:5288-96. 2000
    ..Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead compounds...
  23. ncbi request reprint Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx
    F A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    J Org Chem 65:9039-46. 2000
    ..The levels of activity shown by breviones B, C, and E in the etiolated wheat coleoptiles bioassay, especially breviones E (100% inhibition) and C (80% inhibition) both at 10(-4) M, suggest them as lead compounds for new agrochemicals...
  24. ncbi request reprint Search for a standard phytotoxic bioassay for allelochemicals. Selection of standard target species
    F A Macias
    Departamento de Quimica Organica, Universidad de Cadiz, C República Saharaui s n, Cadiz, Spain
    J Agric Food Chem 48:2512-21. 2000
    ....
  25. ncbi request reprint Bioactive terpenoids from sunflower leaves cv. Peredovick
    Francisco A Macias
    Grupo de Alelopati a, Departamento de Qui mica Orgánica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real, Spain
    Phytochemistry 61:687-92. 2002
    ..The sesquiterpenes heliannuol A and helibisabonol A and the sesquiterpene lactone leptocarpin inhibited the growth of etiolated wheat coleoptiles...
  26. ncbi request reprint Degradation studies on benzoxazinoids. Soil degradation dynamics of 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and its degradation products, phytotoxic allelochemicals from gramineae
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, Facultad de Ciencias, C República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 52:6402-13. 2004
    ..Astron soil. AMPO was the final degradation product observed for DIMBOA in the soils and experimental conditions selected. Consequences for activity and stability of these compounds in relation to allelopathy are discussed...
  27. ncbi request reprint Bioactive lignans from a cultivar of Helianthus annuus
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 52:6443-7. 2004
    ..The structure-activity relationships are discussed...
  28. ncbi request reprint Bioactive apocarotenoids annuionones F and G: structural revision of annuionones A, B and E
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real Cadiz, Spain
    Phytochemistry 65:3057-63. 2004
    ..The isolation of higher amounts of annuionones A and E allowed us to realize a more comprehensive spectroscopical study. We propose a revised structure for annuionone A, B and E based on careful re-analyses of new spectroscopical data...
  29. ncbi request reprint Structure-Activity Relationships (SAR) studies of benzoxazinones, their degradation products and analogues. phytotoxicity on standard target species (STS)
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui, S N, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 53:538-48. 2005
    ..2-Deoxy derivatives of natural benzoxazinones display a wide range of activities that allow proposing them as new leads for natural herbicide models with a 1,4-benzoxazine skeleton...
  30. ncbi request reprint Allelopathy. A natural strategy for weed control
    F A Macias
    Grupo de Alelopatia, Departamento de Química Orgánica Facultad de Ciendas, Universidad de Cádiz Apdo 40, E 11510 Puerto Real, Cadiz, Spain
    Commun Agric Appl Biol Sci 69:13-23. 2004
  31. ncbi request reprint Sesquiterpene lactones with potential use as natural herbicide models (I): trans,trans-germacranolides
    F A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 47:4407-14. 1999
    ..The levels of radicle inhibition obtained with some compounds on wheat are totally comparable to those of Logran and allow to propose them as lead compounds...
  32. ncbi request reprint Application of Hansch's model to guaianolide ester derivatives: a quantitative structure-activity relationship study
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apdo 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 53:3530-9. 2005
    ..Finally, a second hydroxyl group enhances differences of activity between alkylic side chain derivatives by increasing differences in van der Waals interactions...
  33. ncbi request reprint Structure-activity relationship studies of benzoxazinones and related compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, c o República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 53:4373-80. 2005
    ..Their activities confirm the direction proposed in our previous SAR study, which establishes D-DIBOA to be the best lead for natural herbicide model development with benzoxazinone structure...
  34. ncbi request reprint Natural and synthetic podolactones with potential use as natural herbicide models
    F A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apartado 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 48:3003-7. 2000
    ..The specific structural requirements related to their activities are studied. On the basis of these results, their use as potential natural herbicide models is proposed...
  35. ncbi request reprint Allelopathy as a new strategy for sustainable ecosystems development
    Francisco A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Spain
    Biol Sci Space 17:18-23. 2003
    ....
  36. ncbi request reprint Degradation studies on benzoxazinoids. Soil degradation dynamics of (2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-(2H)- 1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and its degradation products, phytotoxic allelochemicals from Gramineae
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apartado 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 53:554-61. 2005
    ..APO was not degraded after three months in soil, suggesting that its degradation rate in soil is very slow...
  37. ncbi request reprint SAR studies of sesquiterpene lactones as Orobanche cumana seed germination stimulants
    Juan C G Galindo
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, C República Saharaui s n, Apartado 40, 11510 Puerto Real, Cadiz, Spain
    J Agric Food Chem 50:1911-7. 2002
    ..These properties could be related to their biological activity...
  38. ncbi request reprint Dehydrozaluzanin C: a potent plant growth regulator with potential use as a natural herbicide template
    F A Macias
    Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Cadiz, Puerto Real, Spain
    Phytochemistry 54:165-71. 2000
    ..These results confirm DHZ as a potent plant growth regulator and a good candidate for the development of new herbicide models...
  39. doi request reprint SFE kinetics of bioactive compounds from Helianthus annuus L
    Lourdes Casas
    Department of Chemical Engineering, Food Technology and Environmental Technologies, Faculty of Science, University of Cadiz, Puerto Real, Cadiz, Spain
    J Sep Sci 32:1445-53. 2009
    ..The extractions were carried out in a pilot plant with an extraction vessel with a capacity of 2 L...
  40. doi request reprint Sesquiterpenes as immunosuppressants
    Alba Muñoz-Suano
    Departamento de Bioquímica y Biología Molecular Inmuologia, Universidad de Cadiz, Hospital Universitario de Puerto Real, Unidad de Investigacion, Carretera NIV Km665, 11510 Puerto Real, Cadiz, Spain
    Transplantation 88:S24-30. 2009
    ..The search for new immunosuppressive drugs is a high priority. Sesquiterpenes constitute a family of compounds with a great variety of biological activities due to their reactive moieties...
  41. doi request reprint Application of Hansch's model to capsaicinoids and capsinoids: a study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids
    Gerardo F Barbero
    Department of Analytical Chemistry, University of Cadiz, Avda Republica Saharaui, S N, Puerto Real, Cadiz, Spain
    J Agric Food Chem 58:3342-9. 2010
    ..coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds...
  42. ncbi request reprint Heliespirones B and C: two new plant heliespiranes with a novel spiro heterocyclic sesquiterpene skeleton
    Francisco A Macias
    Grupo de Alelopatia, Departamento de Quimica Organica, Universidad de Cadiz, Facultad de Ciencias, C República Saharaui s n, 11510 Puerto Real, Cadiz, Spain
    Org Lett 8:4513-6. 2006
    ..The structural elucidation was based on extensive spectral studies. A probable biogenesis of heliespirone skeleton is proposed and discussed. The structure of heliespirone B has been confirmed by X-ray diffraction analysis...
  43. doi request reprint Aneugenic effects of benzoxazinones in cultured human cells
    Elena Arroyo
    Grupo de Alelopatia, Departamento de Quimica Organica, Facultad de Ciencias, 11510 Puerto Real, Cadiz, Spain
    Mutat Res 695:81-6. 2010
    ..Our findings indicate that benzoxazinoids could be potential genotoxins for human cells...