1. AGR2451 Lecture 14 (M. Raizada) Mid-term Exam coming up Review session (in class)coming up Reading for this week (Lecture 14 + 15): p.328-354 Plants, Genes and Agriculture (On Reserve) Review and completion of last lecture: Lecture 14 Notes - Plants and the Environment II – “Chemical Ecology” 1. INTRODUCTION/OVERVIEW Evolution created complex nutrient molecules, complex carbon structures and storage tissues. Viruses, bacteria, fungi, insects, herbivores want to get access to all of this. How do pathogens gain access inside plant tissues? From Biochemistry and Molecular Biology of Plants, page 1104 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 Slide 14.1

2. first defense is waxy cuticle and cell wall plants are immobile but not defenseless plants are simple morphologically; instead they have invested in complex biochemistry land plants use >50,000 chemicals (“secondary metabolites”) to interact with their environments up to 10% of the dry mass of plants is made up of chemicals designed for defense against predators toxic secondary metabolites are stored in the vacuole until needed worldwide preharvest crop losses are 14% from insects; 12% from disease; 10% from weeds; additional losses occur post-harvest including worms and insects that feed on seeds/storage organs 2. Overview of Plant Pathogens there has been co-evolution of plant pathogens (viruses, bacteria, fungi) including herbivores (insects, etc.) and the toxic chemistry of land plants how do plant toxins damage pathogens? 1/6 th of all food grown is consumed by insects insects are often specialists which only feed on one or a few species, but there can also be generalists plants evolved toxic chemicals for all insects, but then a few insects developed resistance, hence these are the specialists in farmer’s fields, the specialists thrive because of an abundant food supply of a single species and hence these insects multiply crop rotation is very useful for combatting specialists (corn - soybeans combat northern corn rootworm in the U.S. midwest). Why?

3. 2. Overview of Plant Pathogens nematodes – several hundred species feed on plants, usually roots – and can grow outside or inside cells where they suck photosynthate viruses – their DNA can move through plasmodesmata, but do not infect meristems. Why do viruses not infect meristems? if bacteria invade conductive tissues, then water cannot be transported, so cause wilts if bacteria spread rapidly and kill cells, then called blights Agrobacterium also produces or mimics plant hormones to create tumor galls of 100,000 fungal species, 8000 cause plant diseases – they produce enzymes which can digest cell walls and then spread from cell to cell; plant rusts are among the worst diseases, caused by Basidiomycete fungi From Biochemistry and Molecular Biology of Plants, page 1106 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 Slide 14.3

4. 3. CLASSES OF SECONDARY METABOLITES (>50,000) -3 main pathways (terpenes, alkaloids, phenylpropanoids) A. Terpenes (>25,000 types) 5C skeleton (isoprene) as 2,4,6, 8 or more polymers; the smaller ones (5C,10C) are volatile Images from Biochemistry and Molecular Biology of Plants, pp. 1252 and 1255 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 What molecule does the 5C skeleton originate from? can be volatile, released by epidermal gland cells as in flowers (as perfumes) terpenes are essential oils found in herbs and spices that give peppermint, basil or sage their smells; they are the aromatic substance in the resin of wounded conifer trees thyme Lemon Leaf Secretory cavity Gland Hair of spearmint Resin Duct of pine Slide 14.4

5. A. Terpenes (continued) why is volatility useful? 1) warn insects of plant toxicity 2) attract insect pollinators or herbivores to eat fruits terpenes include leaf feeding deterrants, allelopathic agents, insecticides, pollinator attractants and anti-herbivore agents From Biochemistry and Molecular Biology of Plants, page 1267 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 Slide 14.5 40C version of terpene constitutes carotenoids such as lycopene which gives tomato its red colour. Why are carotenoids useful and how do they function? antioxidants: ring structures absorb high energy electrons

6. B. Alkaloids (>12,000 types) synthesized from amino acids Tryptophan, Tyrosine, Phenylalanine, Lysine and Arginine; all contain Nitrogen Images from Biochemistry and Molecular Biology of Plants, pp. 1288, 1269, 1271 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 alkaloids affect the central nervous system, so used in medicines (include morphine, codeins, ephedrine), as well as stimulants or sedatives (caffeine, cocaine, and nicotine) Socrates drank hemlock, an alkaloid, to die (execution in 399 BC) Cleopatra used henbane to dilate her pupils to look more alluring to her male political rivals Slide 14.6

7. B. Alkaloids (continued) some larvae gather alkaloids from plants and convert them into pheromones stored in abdominal scent organs nicotine: one of the first and most effective insecticides used by humans. Herbivory stimulates nicotine synthesis in wild tobacco caffeine: at very low levels, caffeine kills the larvae of the tobacco hornworn by inhibiting an essential enzymatic reaction Images from Biochemistry and Molecular Biology of Plants, page 1273 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 Slide 14.7

8. C. Phenylpropanoids (>8000 compounds) skeleton consists of C6 + C3: phenyl ring of 6 carbon with a hydroxyl (OH) group attached to a 3 carbon tail they are derived from amino acids Phenylalanine or Tyrosine through loss of the amino (NH2) group Images from Biochemistry and Molecular Biology of Plants, page 1287 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 many compounds involved in cell wall structural role and hence were essential for adaptation of plants onto land includes the phenolics = 6C ring with an OH (hydroxyl group); this constitutes 40% of the organic carbon in the biosphere. Why so much and in what form? Slide 14.8

9. C. Phenylpropanoids - lignin (cont’d) lignin is a complex polymer of phenol which is deposited into cell walls of the vascular tissue of plants to give them strength lignin accounts for 20-30% of the dry weight of all vascular plant tissues whereas cellulose permits water transport, it is lignin that blocks it; hence lignin required to transport water so essential for land plant evolution lignin is often produced after pathogen attack to seal up the infected cells and because it is toxic Images from Biochemistry and Molecular Biology of Plants, page 1300 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 tannins are polymers of phenols which react with proteins to make them less digestible; high levels of tannins in forage crops deter feeding by cattle. Tannins may also give leaves an unpleasant taste Slide 14.9

10. 3. Phenylpropanoids - the flavonoids flavonoids (4500 compounds): these give flowers their colour as pigments, flavonoids are often found inside plant vacuoles Images from Biochemistry and Molecular Biology of Plants, page 1303 + 1305 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 though they are also feeding deterrants and signalling molecules (legume-Rhizobium signal); Slide 14.10

11. C. Phenylpropanoids coumarin (a flavonoid) of which there are 1500 types can cause internal bleeding in mammals, includes a rodenticide psoralen (a flavonoid) is derived from celery and is used to treat skin disordersincludes anticancer drugs such as taxol plant phenolics contribute to fragrances and flavours Images from Biochemistry and Molecular Biology of Plants, page 1315 B. Buchanan, W. Gruissem, and R. Jones ASPP Publishing, Rockville, MD, 2000 Slide 14.11

12. D. Unusual amino acids plants produce up to 300 nonprotein amino acids within their seeds. Why? E. Inhibitors of Insect Digestive Enzymes plants produce proteins such as amylase inhibitors and protease inhibitors which inhibit insect digestion of starch and protein in the insect gut by direct binding to the enzyme At the molecular level, how do insects (and other pathogens) gain resistance to these secondary metabolites? 4. HERBICIDES/PESTICIDES and HUMAN HEALTH Central Problem: need to breed for plants that have pesticides in leaves/ vegetative parts, but not in edible parts. Our ancestors bred away pesticides in seeds and other storage organs, yet simultaneously increased the nutrients at these sinks, and so now we compensate with artificial pesticides applied to the plant surface. example: wild lima beans have high leves of cyanogenic glucosides, whereas cultivated lima beans have very low level, so cultivated plants are more susceptible to attack by insects and pathogens often, modern agriculture has substituted good farming practices for herbicides and pesticidesstressful (dense) conditions Slide 14.12

13. Metabolites and Human Health (continued) about half of the secondary compounds that have so far been tested cause cancer in lab rodents at various doses, whereas others can prevent cancer, but there is very limited research in this area what is natural? organic marketing makes it seem as if the only source of pesticides are human what are the secondary metabolites found in herbs? In “natural/ancient” medicines? which are often leaves or roots (vegetative structures). What are the problems associated with applied pesticides? Slide 14.13