Low-molecular-weight metabolite systems chemistry

Frontiers in Environmental Science

Volumn 3, Issue MAR, 2015, Pages

  Hadacek, Franz ^a   Bachmann, Gert ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

Biotransistors; Charge transfer complexes; Chemoelectrical signaling system; Coordination complexes; Primary metabolism; Redox chemistry; Secondary metabolism; Semiconductors

Indexed keywords

EID: 85041330200     PISSN: None     EISSN: 2296665X     Source Type: Journal    
DOI: 10.3389/fenvs.2015.00012     Document Type: Review

References (182)

1. Amdursky, N., Molotskii, M., Gazit, E., and Rosenman, G. (2010). Elementary building blocks of self-assembled peptide nanotubes. J. Am. Chem. Soc. 132, 15632-15636. doi: 10.1021/ja104373e
2. Anarat-Cappillino, G., and Sattely, E. S. (2014). The chemical logic of plant natural product biosynthesis. Curr. Opin. Plant Biol. 19, 51-58. doi: 10.1016/j.pbi.2014.03.007
3. Apel, K., and Hirt, H. (2004). Reactive oxygen species: metabolism, oxidative stress, and signal transduction. Annu. Rev. Plant Biol. 55, 373-399. doi: 10.1146/annurev.arplant.55.031903.141701
4. Asensi-Fabado, M. A., and Munné-Bosch, S. (2010). Vitamins in plants: occurrence, biosynthesis and antioxidant function. Trends Plant Sci. 15, 582-592. doi: 10.1016/j.tplants.2010.07.003
5. Astier, J., Kulik, A., Koen, E., Besson-Bard, A., Bourque, S., Jeandroz, S., et al. (2012). Protein S-nitrosylation: what's going on in plants? Free Radic. Biol. Med. 53, 1101-1110. doi: 10.1016/j.freeradbiomed.2012.06.032
6. Ball, P. (2008). Water as an active constituent in cell biology. Chem. Rev. 108, 74-108. doi: 10.1021/cr068037a
7. Bar-Even, A., Flamholz, A., Noor, E., and Milo, R. (2012). Rethinking glycolysis: on the biochemical logic of metabolic pathways. Nat. Chem. Biol. 8, 509-517. doi: 10.1038/nchembio.971
8. Barnes, J., Anderson, L. A., and Phillipson, J. D. (2001). St John's wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties. J. Pharm. Pharmacol. 53, 583-600. doi: 10.1211/0022357011775910
9. Bartoli, C. G., Casalongué, C. A., Simontacchi, M., Marquez-Garcia, B., and Foyer, C. H. (2013). Interactions between hormone and redox signalling pathways in the control of growth and cross tolerance to stress. Environ. Exp. Bot. 94, 73-88. doi: 10.1016/j.envexpbot.2012.05.003
10. Bednarek, P., and Osbourn, A. (2009). Plant-microbe interactions: chemical diversity in plant defense. Science 324, 746-748. doi: 10.1126/science.1171661
11. Betina, V. (1989). Mycotoxins. Chemical, Biological, and Environmental Aspects. Amsterdam: Elsevier.
12. Bleecker, A. B., and Kende, H. (2000). Ethylene: a gaseous signal molecule in plants. Annu. Rev. Cell Dev. Biol. 16, 1-18. doi: 10.1146/annurev.cellbio.16.1.1
13. Boyton, R. J. (2002). Pulmonary defences to acute respiratory infection. Br. Med. Bull. 61, 1-12. doi: 10.1093/bmb/61.1.1
14. Bräse, S., Gläser, F., Kramer, C. S., Lindner, S., Linsenmeier, A. M., Masters, K.-S., et al. (2013). The Chemistry of Mycotoxins. New York, NY: Springer.
15. Buchanan, B. B., Gruissem, W., and Jones, R. L. (eds.). (2009). Biochemistry & Molecular Biology of Plants. Rockville, MD: American Soc. of Plant Physiologists.
16. Burns, J., Gardner, P. T., O'Neil, J., Crawford, S., Morecroft, I., McPhail, D. B., et al. (2000). Relationship among antioxidant activity, vasodilation capacity, and phenolic content of red wines. J. Agric. Food Chem. 48, 220-230. doi: 10.1021/jf9909757
17. Cabello-Hurtado, F., Gicquel, M., and Esnault, M.-A. (2012). Evaluation of the antioxidant potential of cauliflower (Brassica oleracea) from a glucosinolate content perspective. Food Chem. 132, 1003-1009. doi: 10.1016/j.foodchem.2011.11.086
18. Calabrese, E. J. (2005). Paradigm lost, paradigm found. The re-emergence of hormesis as a fundamental dose response model in the toxicological sciences. Environ. Pollut. 138, 378-411. doi: 10.1016/j.envpol.2004.10.001
19. Carlson, N. R. (2014). Physiology of Behavior. Harlow: Pearson Ecucation, Inc.
20. Cheng, Q., and Qian, M.-L. (2012). Piezoelectric effect of cell's membrane. J. Acoust. Soc. Am. 131, 3246. doi: 10.1121/1.4708114
21. Chobot, V., and Hadacek, F. (2009). Milieu-dependent pro- and antioxidant activity of juglone may explain linear and nonlinear effects on seedling development. J. Chem. Ecol. 35, 383-390. doi: 10.1007/s10886-009-9609-5
22. Christensen, L. P., and Brandt, K. (2006). Bioactive polyacetylenes in food plants of the apiaceae family: occurrence, bioactivity and analysis. J. Pharm. Biomed. Anal. 41, 683-693. doi: 10.1016/j.jpba.2006.01.057
23. Clouse, S. D., and Sasse, J. M. (1998). Brassinosteroids: essential regulators of plant growth and development. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49, 427-451. doi: 10.1146/annurev.arplant.49.1.427
24. Crichton, C. R. (2008). Biological Inorganic Chemistry-An Introduction. Amsterdam: Elsevier.
25. Crozier, A. (ed.). (2006). Plant Secondary Metabolites: Occurence, Structure and Role in the Human Diet. Oxford: Blackwell Publ.
26. Curtis, P. J., and Cross, B. E. (1954). Gibberellic acid. A new metabolite from the culture filtrates of Gibberella fujikuroi. Chem. Ind. 35, 1066.
27. Davies, E. (1987). Action potentials as multifunctional signals in plants-A unifying hypothesis to explain apparently disparate wound responses. Plant Cell Environ. 10, 623-631. doi: 10.1111/j.1365-3040.1987.tb01844.x
28. Davies, E. (1993). Intercellular and intracellular signals and their transduction via the plasma membrane-cytoskeleton interface. Semin. Cell Biol. 4, 139-147. doi: 10.1006/scel.1993.1017
29. Davies, K. J. A. (2000). Oxidative stress, antioxidant defenses, and damage removal, repair, and replacement systems. IUBMB Life 50, 279-289. doi: 10.1080/15216540051081010
30. De Rosa, M., Gambacorta, A., and Gliozzi, A. (1986). Structure, biosynthesis, and physicochemical properties of archaebacterial lipids. Microbiol. Mol. Biol. Rev. 40, 70-80.
31. De Tullio, M. C. (2010). Antioxidants and redox regulation. Changing notions in a changing world. Plant Physiol. Biochem. 48, 289-291. doi: 10.1016/j.plaphy.2010.02.011
32. De Tullio, M. C. (2012). Beyond the antioxidant: the double life of vitamin C. Subcell. Biochem. 56, 49-65. doi: 10.1007/978-94-007-2199-9_4
33. Demain, A. L. (1996). "Fungal secondary metabolim: regulation and function," in A Century of Mycology, ed B. C. Sutton (Cambridge; New York: Cambridge University Press), 233-254.
34. Demidchik, V. (2015). Mechanisms of oxidative stress in plants: from classical chemistry to cell biology. Environ. Exp. Bot. 109, 212-228. doi: 10.1016/j.envexpbot.2014.06.021
35. Denisov, E. T., and Denisova, T. G. (2009). The reactivity of natural phenols. Russ. Chem. Rev. 78, 1047-1073. doi: 10.1070/RC2009v078n11ABEH004084
36. D'Haeze, W., and Holsters, M. (2002). Nod factor structures, responses, and perception during initiation of nodule development. Glycobiology 12, 79R-105R doi: 10.1093/glycob/12.6.79R
37. Diamond, J. M., and Wright, E. M. (1969). Biological membranes: the physical basis of ion and nonelectrolyte selectivity. Annu. Rev. Physiol. 31, 581-646. doi: 10.1146/annurev.ph.31.030169.003053
38. Dixon, R. A. (2001). Natural products and plant disease resistance. Nature 411, 843-847. doi: 10.1038/35081178
39. Dorf, R. C., and Svoboda, J. A. (2001). Introduction to Electric Circuits. New York, NY: Wiley.
40. Doukas, P. H. (1975). "The role of charge-transfer processes in bioactive materials," in Drug Design, ed E. J. Ariëns (New York; London: Academic Press), 133-169.
41. Eberson, L. E. (1987). Electron Transfer Reactions in Organic Chemistry. Berlin; New York: Springer.
42. Evert, R. F., Eichhorn, S. E., Langenfeld-Heyser, R., and Esau, K. (2009). Esau's Pflanzenanatomie. Meristeme, Zellen und Gewebe der Pflanzen: Ihre Struktur, Funktion und Entwicklung. Berlin: De Gruyter.
43. Fani, R., and Fondi, M. (2009). Origin and evolution of metabolic pathways. Phys. Life Rev. 6, 23-52. doi: 10.1016/j.plrev.2008.12.003
44. Farmer, E. E., Gasperini, D., and Acosta, I. F. (2014). The squeeze cell hypothesis for the activation of jasmonate synthesis in response to wounding. New Phytol. 204, 282-288. doi: 10.1111/nph.12897
45. Farquhar, E., and Hasler, P. (2005). A bio-physically inspired silicon neuron. IEEE T. Circuits I 52, 477-488. doi: 10.1109/TCSI.2004.842871
46. Ferrier, D. R., and Harvey, R. A. (2014). Lippincott's Illustrated Reviews: Biochemistry. Philadelphia, PA: Wolters Kluwer Health; Lippincott Williams & Wilkins.
47. Firn, R. (2010). Nature's Chemicals. The Natural Products that Shaped Our World. Oxford: Oxford University Press.
48. Firn, R. D., and Jones, C. G. (2009). A Darwinian view of metabolism: molecular properties determine fitness. J. Exp. Bot. 60, 719-726. doi: 10.1093/jxb/erp002
49. Fraenkel, G. S. (1959). The raison d'etre of secondary plant substances; these odd chemicals arose as a means of protecting plants from insects and now guide insects to food. Science 129, 1466-1470. doi: 10.1126/science.129.3361.1466
50. Fraústo da Silva, J. J. R., and Williams, R. J. P. (2001). The Biological Chemistry of the Elements. The Inorganic Chemistry of Life. Oxford, UK: Oxford University Press.
51. Fridovich, I. (1998). Oxygen toxicity. A radical explanation. J. Exp. Biol. 201, 1203-1209.
52. Fromm, J., and Lautner, S. (2012). "Generation, transmission, and physiological effects of electrical signals in plants," in Plant Electrophysiology: Signaling and Responses, ed A. G. Volkov (Berlin: Springer), 207-232.
53. Fujita, M., Fujita, Y., Noutoshi, Y., Takahashi, F., Narusaka, Y., Yamaguchi-Shinozaki, K., et al. (2006). Crosstalk between abiotic and biotic stress responses: a current view from the points of convergence in the stress signaling networks. Curr. Opin. Plant Biol. 9, 436-442. doi: 10.1016/j.pbi.2006.05.014
54. Fukada, E. (1984). Piezoelectricity of natural biomaterials. Ferroelectrics 60, 285-296. doi: 10.1080/00150198408017529
55. Funk, C. D. (2001). Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 294, 1871-1875. doi: 10.1126/science.294.5548.1871
56. Fusetani, N. (2012). "Marine natural products," in Natural Products in Chemical Biology, ed N. Civjan (Hoboken, NJ: Wiley), 31-64.
57. Gershenzon, J. (2002). "Secondary metabolites and plant defense," in Plant Physiology, eds L. Taiz and E. Zeiger (Sunderland, MA: Sinauer), 283-303.
58. Giles, G. I., and Jacob, C. (2002). Reactive sulfur species. An emerging concept in oxidative stress. Biol. Chem. 383, 375-388. doi: 10.1515/BC.2002.042
59. Gooday, G. W. (1978). Functions of trisporic acid. Philos. Trans. R. Soc. Lond. B Biol. Sci. 284, 509-520. doi: 10.1098/rstb.1978.0086
60. Gotter, A. L., Kaetzel, M. A., and Dedman, J. R. (1998). Electrophorus electricus as a model system for the study of membrane excitability. Comp. Biochem. Physiol. A 119, 225-241. doi: 10.1016/S1095-6433(97)00414-5
61. Gräfe, U. (1992). Biochemie der Antibiotika. Struktur - Biosynthese - Wirkmechanismus. Heidelberg: Spektrum Akad. Verlag.
62. Greenhill, J. V., and Grayshan, P. (1992). "The cevane group of Veratrum alkaloids," in The Alkaloids, eds A. Brossi and G. A. Cordell (San Diego, CA: Academic Press), 177-237.
63. Greenstein, B., and Wood, D. F. (2011). The Endocrine System at a Glance. Chichester: Wiley-Blackwell.
64. Groß, F., Durner, J., and Gaupels, F. (2013). Nitric oxide, antioxidants and pro-oxidants in plant defence responses. Front. Plant Sci. 4:419. doi: 10.3389/fpls.2013.00419
65. Grubb, C. D., and Abel, S. (2006). Glucosinolate metabolism and its control. Trends Plant Sci. 11, 89-100. doi: 10.1016/j.tplants.2005.12.006
66. Gruhlke, M. C. H., and Slusarenko, A. J. (2012). The biology of reactive sulfur species (RSS). Plant Physiol. Biochem. 59, 98-107. doi: 10.1016/j.plaphy.2012.03.016
67. Gülçin, I., Beydemir, S., Alici, H. A., Elmastas, M., and Büyükokuroglu, M. E. (2004). In vitro antioxidant properties of morphine. Pharmacol. Res. 49, 59-66. doi: 10.1016/j.phrs.2003.07.012
68. Hadacek, F. (2002). Secondary metabolites as plant traits: current assessment and future perspectives. Crit. Rev. Plant Sci. 21, 273-322. doi: 10.1080/0735-260291044269
69. Hadacek, F., Engelmeier, D., Bachmann, G., and Chobot, V. (2011). Hormesis and a chemical raison d'etre for secondary plant metabolites. Dose-Response 9, 79-116. doi: 10.2203/dose-response.09-028.Hadacek
70. Halliwell, B. (2006). Reactive species and antioxidants. Redox biology is a fundamental theme of aerobic life. Plant Physiol. 141, 312-322. doi: 10.1104/pp.106.077073
71. Halliwell, B., and Gutteridge, J. M. C. (2007). Free Radicals in Biology and Medicine. Oxford: Oxford University Press.
72. Hardeland, R. (2008). Melatonin, hormone of darkness and more - occurrence, control mechanisms, actions and bioactive metabolites. Cell. Mol. Life Sci. 65, 2001-2018. doi: 10.1007/s00018-008-8001-x
73. Hartmann, T. (2007). From waste products to ecochemicals. Fifty years research of plant secondary metabolism. Phytochemistry 68, 2831-2846. doi: 10.1016/j.phytochem.2007.09.017
74. Hauser, C. A. E., and Zhang, S. (2010). Peptides as biological semiconductors. Nature 468, 516-517. doi: 10.1038/468516a
75. Hedden, P., and Thomas, S. (eds.). (2006). Plant Hormone Signaling. Oxford, UK: Blackwell.
76. Heimburg, T. (2012). The capacitance and electromechanical coupling of lipid membranes close to transitions: the effect of electrostriction. Biophys. J. 103, 918-929. doi: 10.1016/j.bpj.2012.07.010
77. Hercules, D. M. (1969). Chemiluminescence from electron-transfer reactions. Acc. Chem. Res. 2, 301-307. doi: 10.1021/ar50022a003
78. Heyland, A., Hodin, J., and Reitzel, A. M. (2005). Hormone signaling in evolution and development: a non-model system approach. BioEssays 27, 64-75. doi: 10.1002/bies.20136
79. Hille, B. (2001). Ion Channels of Excitable Membranes. Sunderland, MS: Sinauer.
80. Hiramoto, K., Ojima, N., Sako, K., and Kikugawa, K. (1996). Effect of plant phenolics on the formation of the spin-adduct of hydroxyl radical and the DNA strand breaking by hydroxyl radical. Biol. Pharm. Bull. 19, 558-563. doi: 10.1248/bpb.19.558
81. Ishibashi, M., Yamaguchi, N., Sasaki, T., and Kobayashi, J. (1994). Amphidinolide N, a novel 26-membered macrolide with remarkably potent cytotoxicity from the cultured marine dinoflagellate Amphidinium sp. J. Chem. Soc. Chem. Commun. 12, 1455-1456. doi: 10.1039/c39940001455
82. Ishimaru, Y., Hamamoto, S., Uozumi, N., and Ueda, M. (2012). "Regulatory mechanism of plant nyctinastic movement: an ion channel-related plant behavior," in Plant Electrophysiology: Signaling and Responses, ed A. G. Volkov (Berlin: Springer), 125-142.
83. Jaeken, L., and Matveev, V. V. (2012). Coherent behavior and the bound state of water and K+ imply another model of bioenergetics: negative entropy instead of high-energy bonds. Open Biochem. J. 6, 139-159. doi: 10.2174/1874091X01206010139
84. Jaffe, L. F. (1977). Electrophoresis along cell membranes. Nature 265, 600-602. doi: 10.1038/265600a0
85. Jansen, B. J., and de Groot, A. (2004). Occurrence, biological activity and synthesis of drimane sesquiterpenoids. Nat. Prod. Rep. 21, 449-477. doi: 10.1039/b311170a
86. Jarvis, B. B., and Miller, J. D. (1996). "Natural products, complexity and evolution," in Phytochemical Diversity and Redundancy in Ecological Interactions, eds J. T. Romeo, J. A. Saunders, and P. Barbosa (New York, NY: Plenum Press), 265-294.
87. Jerzmanowski, A., and Archacki, R. (2013). "Hormonal signaling in plants and animals: an epigenetic viewpoint," in Epigenetic Memory and Control in Plants, eds G. Grafi and N. Ohad (Berlin, New York: Springer), 107-125.
88. Jung, I. L., and Kim, I. G. (2003). Thiamine protects against paraquat-induced damage: scavenging activity of reactive oxygen species. Environ. Toxicol. Pharmacol. 15, 19-26. doi: 10.1016/j.etap.2003.08.001
89. Kappus, H., and Sies, H. (1981). Toxic drug effects associated with oxygen metabolism: redox cycling and lipid peroxidation. Experientia 37, 1233-1241. doi: 10.1007/BF01948335
90. Keown, D. (2014). The Spark in the Machine. How the Science of Acupuncture Explains the Mysteries of Western Medicine. London; Philadelphia: Singing Dragon.
91. Kim, J., Yun, S., Mahadeva, S. K., Yun, K., Yang, S. Y., and Maniruzzaman, M. (2010). Paper actuators made with cellulose and hybrid materials. Sensors 10, 1473-1485. doi: 10.3390/s100301473
92. Kindermann, M., Stahl, I., Reimold, M., Pankau, W. M., and von Kiedrowski, G. (2005). Systems chemistry. Kinetic and computational analysis of a nearly exponential organic replicator. Angew. Chem. Int. Ed. 44, 6750-6755. doi: 10.1002/anie.200501527
93. Kinzel, H. (1989). Stoffwechsel der Zelle. Die zentralen Vorgänge des Stoffwechsels mit ihren physikalisch-chemischen Grundlagen. Stuttgart: Ulmer.
94. Kovacic, P., and Somanathan, R. (2009). Novel, unifying mechanism for mescaline in the central nervous system. Electrochemistry, catechol redox metabolite, receptor, cell signaling and structure activity relationships. Oxid. Med. Cell. Longev. 2, 181-190. doi: 10.4161/oxim.2.4.9380
95. Langenheim, J. H. (2003). Plant Resins. Chemistry, Evolution, Ecology, and Ethnobotany. Portland, OR: Timber Press.
96. Leppard, G. G. (1995). The characterization of algal and microbial mucilages and their aggregates in aquatic ecosystems. Sci. Total Environ. 165, 103-131. doi: 10.1016/0048-9697(95)04546-D
97. Levin, M., Thorlin, T., Robinson, K. R., Nogi, T., and Mercola, M. (2002). Asymmetries in H+/K+-ATPase and cell membrane potentials comprise a very early step in left-right patterning. Cell 111, 77-89. doi: 10.1016/S0092-8674(02)00939-X
98. Ling, G. N. (2001). Life at the Cell and Below-Cell Level. The Hidden History of a Fundamental Revolution in Biology. Melville, NY: Pacific Press.
99. López-Lara, I. M., and Geiger, O. (2010). "Formation of fatty acids," in Handbook of Hydrocarbon and Lipid Microbiology, ed K. N. Timmis (Berlin: Springer), 385-395.
100. Lovley, D. R. (2011). Powering microbes with electricity: direct electron transfer from electrodes to microbes. Environ. Microbiol. Rep. 3, 27-35. doi: 10.1111/j.1758-2229.2010.00211.x
101. Lovley, D. R. (2012). Electromicrobiology. Annu. Rev. Microbiol. 66, 391-409. doi: 10.1146/annurev-micro-092611-150104
102. Macielag, M. J. (2011). "Chemical properties of antimicrobials and their uniqueness," in Antibiotic Discovery and Development, eds T. J. Dougherty and M. J. Pucci (New York, NY: Springer), 793-820.
103. Maischak, H., Zimmermann, M. R., Felle, H. H., Boland, W., and Mithöfer, A. (2010). Alamethicin-induced electrical long distance signaling in plants. Plant Signal. Behav. 5, 988-990. doi: 10.4161/psb.5.8.12223
104. Marrè, E. (1979). Fusicoccin: a tool in plant physiology. Annu. Rev. Plant. Physiol. 30, 273-288. doi: 10.1146/annurev.pp.30.060179.001421
105. Marschner, P. (ed). (2012). Marschner's Mineral Nutrition of Higher Plants. Amsterdam: Elsevier.
106. Martin, R. (1972). Piezoelectricity. Phys. Rev. B 5, 1607-1613. doi: 10.1103/PhysRevB.5.1607
107. Matveev, V. V. (2010). Native aggregation as a cause of origin of temporary cellular structures needed for all forms of cellular activity, signaling and transformations. Theor. Biol. Med. Model. 7:19. doi: 10.1186/1742-4682-7-19
108. McCaig, C. D., Rajnicek, A. M., Song, B., and Zhao, M. (2005). Controlling cell behavior electrically: current views and future potential. Physiol. Rev. 85, 943-978. doi: 10.1152/physrev.00020.2004
109. McKinlay, A. C., Morris, R. E., Horcajada, P., Férey, G., Gref, R., Couvreur, P., et al. (2010). BioMOFs: metal-organic frameworks for biological and medical applications. Angew. Chem. Int. Ed. 49, 6260-6266. doi: 10.1002/anie.201000048
110. Mendelsohn, R., and Balick, M. J. (1995). The value of undiscovered pharmaceuticals in tropical forests. Econ. Bot. 49, 223-228. doi: 10.1007/BF02862929
111. Michal, G. (ed.). (1999). Biochemical Pathways. New York, NY: Wiley.
112. Mindnich, R., Möller, G., and Adamski, J. (2004). The role of 17 beta-hydroxysteroid dehydrogenases. Mol. Cell. Endocrinol. 218, 7-20. doi: 10.1016/j.mce.2003.12.006
113. Modriansky, M., Tyurina, Y. Y., Tyurin, V. A., Matsura, T., Shvedova, A. A., Yalowich, J. C., et al. (2002). Anti-/pro-oxidant effects of phenolic compounds in cells: are colchicine metabolites chain-breaking antioxidants? Toxicology 177, 105-117. doi: 10.1016/S0300-483X(02)00199-3
114. Møller, I. M., Jensen, P. E., and Hansson, A. (2007). Oxidative modifications to cellular components in plants. Annu. Rev. Plant Biol. 58, 459-481. doi: 10.1146/annurev.arplant.58.032806.103946
115. Nakagawa, T., Sakurai, T., Nishioka, T., and Touhara, K. (2005). Insect sex-pheromone signals mediated by specific combinations of olfactory receptors. Science 307, 1638-1642. doi: 10.1126/science.1106267
116. Nakamura, H., Kobayashi, J., Ohizumi, Y., and Hirata, Y. (1982). Isolation and structure of aaptamine a novel heteroaromatic substance possessing a-blocking activity from the sea sponge Aaptos aaptos. Tetrahedr. Lett. 23, 5555-5558. doi: 10.1016/S0040-4039(00)85893-1
117. Nasonov, D. N. (1962). Local Reaction of Protoplasm and Gradual Excitation. (Mestnaya Reaktsiya Protoplazmy I Rasprostranyayushcheesya Vozbuzhdenie). Jerusalem: Published for the National Science Foundation, Washington, by the Israel Program for Scientific Translations; (available from the Office of Technical Services, U.S. Dept. of Commerce, Washington).
118. Niklas, K. J., and Spatz, H.-C. (2012). Plant Physics. Chicago, IL: The University of Chicago Press.
119. Noble, D. (2006). The Music of Life: Biology Beyond Genes. Oxford, UK: Oxford University Press.
120. Noor, E., Eden, E., Milo, R., and Alon, U. (2010). Central carbon metabolism as a minimal biochemical walk between precursors for biomass and energy. Mol. Cell 39, 809-820. doi: 10.1016/j.molcel.2010.08.031
121. Ochiai, E.-I. (2008). Bioorganic Chemistry. A Survey. Amsterdam: Elsevier.
122. Pavlovic, A. (2012). "The effect of electrical signals on photosynthesis and respiration," in Plant Electrophysiology: Signaling and Responses, ed A. G. Volkov (Berlin: Springer), 33-62.
123. Pieterse, C. M. J., Leon-Reyes, A., Van der Ent, S., and Van Wees, S. C. M. (2009). Networking by small-molecule hormones in plant immunity. Nat. Chem. Biol. 5, 308-316. doi: 10.1038/nchembio.164
124. Pollack, G. H. (2001). Cells, Gels, and the Engines of Life. A New, Unifying Approach to Cell Function. Seattle, WA: Ebner & Sons.
125. Pollack, G. H. (2013). The Fourth Phase of Water. Beyond Solid, Liquid, and Vapor. Seattle, WA: Ebner & Sons.
126. Preston, R. R., and Wilson, T. E. (2013). Lippincott's Illustrated Reviews. Physiology. Philadelphia; London: Lippincott Williams & Wilkins.
127. Pross, A. (1985). The single electron shift as a fundamental process in organic chemistry: the relationship between polar and electron-transfer pathways. Acc. Chem. Res. 18, 212-219. doi: 10.1021/ar00115a004
128. Pross, A. (1995). Theoretical and Physical Principles of Organic Reactivity. New York, NY: Wiley.
129. Pross, A. (2005). On the chemical nature and origin of teleonomy. Orig. Life Evol. Biosph. 35, 383-394. doi: 10.1007/s11084-005-2045-9
130. Pross, A. (2012). What is Life? How Chemistry Becomes Biology. Oxford, UK: Oxford University Press.
131. Ramel, F., Birtic, S., Cuiné, S., Triantaphylidés, C., Ravanat, J.-L., and Havaux, M. (2012). Chemical quenching of singlet oxygen by carotenoids in plants. Plant Physiol. 158, 1267-1278. doi: 10.1104/pp.111.182394
132. Reese, R. E., Betts, R. F., and Gumustop, B. (2000). Handbook of Antibiotics. Philadelphia, PA: Lippincott Williams & Wilkins.
133. Rohmer, M. (1999). The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat. Prod. Rep. 16, 565-574. doi: 10.1039/a709175c
134. Romeo, J. T., Ibrahim, R., Varin, L., and de Luca, V. (eds.). (2000). Evolution of Metabolic Pathways. Amsterdam; New York: Pergamon.
135. Rosenthal, G. A. (1982). Plant Nonprotein Amino and Imino Acids. Biological, Biochemical, and Toxicological Properties. New York, NY: Academic Press.
136. Ruiz-Mirazo, K., Briones, C., and de la Escosura, A. (2014). Prebiotic systems chemistry: new perspectives for the origins of life. Chem. Rev. 114, 285-366. doi: 10.1021/cr2004844
137. Sahoo, N., Hoshi, T., and Heinemann, S. H. (2014). Oxidative modulation of voltage-gated potassium channels. Antioxid. Redox Signal. 21, 933-952. doi: 10.1089/ars.2013.5614
138. Schmid, N. B., Giehl, R. F. H., Döll, S., Mock, H.-P., Strehmel, N., Scheel, D., et al. (2014). Feruloyl-CoA 6'-hydroxylase1-dependent coumarins mediate iron acquisition from alkaline substrates in Arabidopsis. Plant Physiol. 164, 160-172. doi: 10.1104/pp.113.228544
139. Schöning, M. J., and Poghossian, A. (2002). Recent advances in biologically sensitive field-effect transistors (BioFETs). Analyst 127, 1137-1151. doi: 10.1039/b204444g
140. Schrödinger, E. (1944). What is Life? Cambridge, UK: Cambridge University Press.
141. Seigler, D. S. (1998). Plant Secondary Metabolism. London: Chapman & Hall.
142. Seybold, S. J., Huber, D. P. W., Lee, J. C., Graves, A. D., and Bohlmann, J. (2006). Pine monoterpenes and pine bark beetles: a marriage of convenience for defense and chemical communication. Phytochem. Rev. 5, 143-178. doi: 10.1007/s11101-006-9002-8
143. Shahat, A. A., Ibrahim, A. Y., Hendawy, S. F., Omer, E. A., Hammouda, F. M., Abdel-Rahman, F. H., et al. (2011). Chemical composition, antimicrobial and antioxidant activities of essential oils from organically cultivated fennel cultivars. Molecules 16, 1366-1377. doi: 10.3390/molecules16021366
144. Shapiro, J. A. (2011). Evolution. A View from the 21st Century. Upper Saddle River, NJ: FT Press Science.
145. Silverman, R. B. (2002). The Organic Chemistry of Enzyme-Catalyzed Reactions. Amsterdam; Boston: Academic Press.
146. Smith, E. A., and Macfarlane, G. T. (1996). Enumeration of human colonic bacteria producing phenolic and indolic compounds: effects of pH, carbohydrate availability and retention time on dissimilatory aromatic amino acid metabolism. J. Appl. Bacteriol. 81, 288-302. doi: 10.1111/j.1365-2672.1996.tb04331.x
147. Song, B., Zhao, M., Forrester, J. V., and McCaig, C. D. (2002). Electrical cues regulate the orientation and frequency of cell division and the rate of wound healing in vivo. Proc. Natl. Acad. Sci. U.S.A. 99, 13577-13582. doi: 10.1073/pnas.202235299
148. Spindler, K.-D., Hönl, C., Tremmel, C., Braun, S., Ruff, H., and Spindler-Barth, M. (2009). Ecdysteroid hormone action. Cell. Mol. Life Sci. 66, 3837-3850. doi: 10.1007/s00018-009-0112-5
149. Srinivasan, K. (2014). Antioxidant potential of spices and their active constituents. Crit. Rev. Food Sci. Nutr. 54, 352-372. doi: 10.1080/10408398.2011.585525
150. Sze, S. M. (1981). Physics of Semiconductor Devices. New York, NY: Wiley.
151. Szent-Györgyi, A. (1957). Bioenergetics. New York, NY: Academic Press.
152. Szent-Györgyi, A. (1960). Introduction to a Submolecular Biology. New York; London: Academic Press.
153. Szent-Györgyi, A. (1968). Bioelectrics. New York, NY: Academic Press.
154. Tarakhovskaya, E. R., Maslov, Y. I., and Shishova, M. F. (2007). Phytohormones in algae. Russ. J. Plant. Physiol. 54, 163-170. doi: 10.1134/S1021443707020021
155. Tian, B., and Hua, Y. (2005). Concentration-dependence of prooxidant and antioxidant effects of aloin and aloe-emodin on DNA. Food Chem. 91, 413-418. doi: 10.1016/j.foodchem.2004.06.018
156. Torssell, K. (1993). Natural Product Chemistry. A Mechanistic and Biosynthetic Approach to Secondary Metabolism. Stockholm: Swedisch Pharmaceutical Press.
157. Triantaphylidès, C., and Havaux, M. (2009). Singlet oxygen in plants: production, detoxification and signaling. Trends Plant Sci. 14, 219-228. doi: 10.1016/j.tplants.2009.01.008
158. Vestergaard, C. L., Flyvbjerg, H., and Møller, I. M. (2012). Intracellular signaling by diffusion: can waves of hydrogen peroxide transmit intracellular information in plant cells? Front. Plant Sci. 3:295. doi: 10.3389/fpls.2012.00295
159. Voeikov, V. (2001). Reactive oxygen species, water, photons and life. Biol. Forum 94, 193-214. doi: 10.1400/22857
160. Voeikov, V. (2006). "Biological significance of active oxygen-dependent processes in aqueous systems," in Water and the Cell, eds G. H. Pollack, I. V. Cameron, and D. N. Wheatly (Dordrecht: Springer), 285-298.
161. Volkov, A. G., Adesina, T., Markin, V. S., and Jovanov, E. (2008). Kinetics and mechanism of Dionaea muscipula trap closing. Plant Physiol. 146, 694-702. doi: 10.1104/pp.107.108241
162. Volkov, A. G., Foster, J. C., and Markin, V. S. (2010). Signal transduction in Mimosa pudica: biologically closed electrical circuits. Plant Cell Environ. 33, 816-827. doi: 10.1111/j.1365-3040.2009.02108.x
163. von Lintig, J. (2012). Metabolism of carotenoids and retinoids related to vision. J. Biol. Chem. 287, 1627-1634. doi: 10.1074/jbc.R111.303990
164. Waldie, T., McCulloch, H., and Leyser, O. (2014). Strigolactones and the control of plant development: lessons from shoot branching. Plant J. 79, 607-622. doi: 10.1111/tpj.12488
165. Wall, M. E., and Wani, M. C. (1995). Camptothecin and taxol: discovery to clinic-thirteenth Bruce F. Cain Memorial Award Lecture. Cancer Res. 55, 753-760.
166. Wang, J., Soisson, S. M., Young, K., Shoop, W., Kodali, S., Galgoci, A., et al. (2006). Platensimycin is a selective FabF inhibitor with potent antibiotic properties. Nature 441, 358-361. doi: 10.1038/nature04784
167. Watson, J. (2013). Oxidants, antioxidants and the current incurability of metastatic cancers. Open Biol. 3:120144. doi: 10.1098/rsob.120144
168. Webb, M. E., Marquet, A., Mendel, R. R., Rébeillé, F., and Smith, A. G. (2007). Elucidating biosynthetic pathways for vitamins and cofactors. Nat. Prod. Rep. 24, 988-1008. doi: 10.1039/b703105j
169. Weng, J.-K., and Noel, J. P. (2012). The remarkable pliability and promiscuity of specialized metabolism. Cold Spring Harb. Symp. Quant. Biol. 77, 309-320. doi: 10.1101/sqb.2012.77.014787
170. Wildon, D. C., Thain, J. F., Minchin, P. E. H., Gubb, I. R., Reilly, A. J., Skipper, Y. D., et al. (1992). Electrical signalling and systemic proteinase inhibitor induction in the wounded plant. Nature 360, 62-65. doi: 10.1038/360062a0
171. Williams, D. H., Stone, M. J., Hauck, P. R., and Rahman, S. K. (1989). Why are secondary metabolites (natural products) biosynthesized. J. Nat. Prod. 52, 1189-1208. doi: 10.1021/np50066a001
172. Williams, R. J. P., and Fraústo da Silva, J. J. R. (2006). The Chemistry of Evolution. The Development of Our Ecosystem. Amsterdam; Boston: Elsevier.
173. Williams, R. J. P., and Rickaby, R. E. M. (2012). Evolution's Destiny. Co-evolving Chemistry of the Environment and Life. Cambridge, UK: Royal Society of Chemistry.
174. Wink, M., and Schimmer, O. (2010). "Molecular modes of action of defensive secondary metabolites," in Functions and Biotechnology of Plant Secondary Metabolites, ed M. Wink (Chichester: Wiley-Blackwell), 21-261.
175. Wink, M., and van Wyk, B.-E. (2008). Mind-Altering and Poisonous Plants of the World. Portland, OR: Timber Press.
176. Woodward, A. W., and Bartel, B. (2005). Auxin: regulation, action, and interaction. Ann. Bot. 95, 707-735. doi: 10.1093/aob/mci083
177. Wu, Q.-H., Wang, X., Yang, W., Nuessler, A. K., Xiong, L.-Y., Kuca, K., et al. (2014). Oxidative stress-mediated cytotoxicity and metabolism of T-2 toxin and deoxynivalenol in animals and humans: an update. Arch. Toxicol. 88, 1309-1326. doi: 10.1007/s00204-014-1280-0
178. Yamanaka, N., Rewitz, K. F., and O'Connor, M. B. (2013). Ecdysone control of developmental transitions: lessons from Drosophila research. Annu. Rev. Entomol. 58, 497-516. doi: 10.1146/annurev-ento-120811-153608
179. Zhang, T., and Lin, W. (2014). Metal-organic frameworks for artificial photosynthesis and photocatalysis. Chem. Soc. Rev. 43, 5982-5993. doi: 10.1039/C4CS00103F
180. Zhao, M., Jin, T., McCaig, C. D., Forrester, J. V., and Devreotes, P. N. (2002). Genetic analysis of the role of G protein-coupled receptor signaling in electrotaxis. J. Cell Biol. 157, 921-927. doi: 10.1083/jcb.200112070
181. Zimmermann, M. R., Maischak, H., Mithoefer, A., Boland, W., and Felle, H. H. (2009). System potentials, a novel electrical long-distance apoplastic signal in plants, induced by wounding. Plant Physiol. 149, 1593-1600. doi: 10.1104/pp.108.133884
182. Zimmermann, M. R., and Mithöfer, A. (2013). "Electrical long-distance signalling in plants," in Long-Distance Systemic Signaling and Communication in Plants, ed F. Baluška (Berlin; New York: Springer), 291-308.