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What’s a phenolic compound? A secondary product that contains a phenol group - a hydroxyl functional group on an aromatic ring. OH Phenolics are a chemically.

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Presentation on theme: "What’s a phenolic compound? A secondary product that contains a phenol group - a hydroxyl functional group on an aromatic ring. OH Phenolics are a chemically."— Presentation transcript:

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3 What’s a phenolic compound? A secondary product that contains a phenol group - a hydroxyl functional group on an aromatic ring. OH Phenolics are a chemically diverse group: many different properties and functions.

4 Biosynthesis of phenolics Shikimic acid pathway is most common in plants. Converts simple carbohydrates into aromatic amino acids. Not present in animals.

5 Most plant phenolics are derived from cinnamic acid formed from phenylalanine by phenylalanine ammonia lyase (PAL) enzyme. PAL PAL activity is inducible: fungal infection, low nutrient levels, high light

6 Major types of phenolics 1. Simple phenolics - e.g. coumarins 2. Lignin - 2nd most abundant compound in plants 3. Flavonoids - two aromatic rings, 2 pathways anthocyanins, flavones/flavonols 4. Condensed tannins polymerized flavonoids 5. Hydrolyzable tannins made of phenolic acids and sugars smaller molecules than condensed tannins

7 Fig simple phenolics Involved in defense against insect herbivores and fungi, some may have allelopathic function.

8 Caffeic acid & ferulic acid implicated in allelopathy. Psoralen is one of several phototoxic furanocoumarins, (UV activated) Simple phenolics Fig

9 Insects usually roll leaves for protection from predation and to create a habitat Sometimes insects roll leaves to prevent furanocourmarins from being activated Furoanocoumarins can certain light wavelengths. (common in Umbelliferae family – celery, parsnip) Leaf rolling insects

10 Furanocoumarins can bind to DNA or react with lipids and proteins

11 Fig Simple phenolics

12 2. Lignin Second most abundant compound in plants. Highly branched polymer of phenylpropanoid groups (benzene-C 3 )

13 -often found in vessel elements, tracheids, and stems; confers structural support. Primary structural role! - Secondary role as a herbivore deterrent by reducing digestibility of plant matter -also difficult for microbes to degrade; its presence slows litter decomposition.

14 Fig Flavonoids - basic structure is two aromatic rings joined by a 3C bridge. a)anthocyanins b)flavones c)flavonols d)isoflavonoids

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16 a) Anthocyanidins and anthocyanins are pigments that give plant tissues red, blue, and purple color. Pollinator attraction Disperser attraction Fig Flavonoids

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18 b & c) flavones and flavonols UV absorbing protection against UV ( nm) insect pollinator attraction Flavonoids continued How we see the golden eyes… How honeybees see golden eyes… UV absorbing flavonols are present in the inner part of petals

19 Rhizobium is attracted to legumes through signaling by isoflavanoids released from roots. d) Isoflavonoids common in legumes antimicrobial properties also involved in signalling e.g. attracting rhizobia

20 Tannins Condensed -formed by polymerization of flavonoid units -common in woody plants Hydrolyzable - contain phenolic acids: gallic acid, & simple sugars - smaller molecules than condensed tannins - more easily hydrolyzed and degraded Tannins reduce growth and survival of many different kinds of herbivores Also act as antioxidants - eat your isoflavonoids Johnny!

21 Many foods contains tannins (e.g. tea, red wine) and have some healthy side effects for humans (e.g. disallowing constriction of blood vessels) Tannins also make protein less digestible. Animals can sense high levels of tannins in their food and opt for another food resource (e.g. mule deer, beavers). High levels of tannins in diet can actually kill some animals.

22 Condensed tannins are polymerized flavonoids.

23 Hydrolyzable tannins are made of phenolics and sugars. Fig

24 The term “tannin” is derived from the tanning process in which raw animal hides are preserved by rubbing tannins on them. The tannins help to complex the proteins and keep them from degrading. This protein-binding property of tannins lends them their toxicity to herbivores. tannins can bind digestion enzymes in the gut of herbivores.tannins can bind digestion enzymes in the gut of herbivores. tannins also form complex polymers when bound to proteins which are difficult to digest, thus decreasing the nutritional value of the plant material.tannins also form complex polymers when bound to proteins which are difficult to digest, thus decreasing the nutritional value of the plant material.

25 Tannins can reduce nutritional value of tissues by binding to proteins, making them less digestible. Care for a spot of milk in your tea? Fig

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27 Creosote bush, Larrea tridentata Leaves are 10-25% phenolic resin. 40% of resin is NDGA (nordihydroguaiaretic acid), remainder is o-methylated flavones and flavonols. Deters insect herbivory. Mammalian herbivores select older leaves (less resin).

28 USDA formerly used NDGA as an antioxidant to prevent rancidity in food. Now known to cause liver and kidney disease in lab animals. Creosote has long been used in traditional Native American and Mexican herbal medicine Active compounds in creosote leaves. · NDGA and similar compounds. · Amino acids. · Flavonoids. · Volatile oils. · Triterpenes. · Saponins.

29 Creosote applications in herbal therapy · To dissolve urinary kidney stones. · Anti inflammatory for respiratory ailments (asthma) and arthritis · To eliminate gallstones · Against urinary infections · For the treatment of venereal disease · As an abortifacient · Against diabetes · Bronchitis and colds · Rheumatism · Against some types of cancer · As a mouthwash against tooth decay and halitosis

30 After life effects of phenolic compounds. Plant litter decomposition, and release of nutrients from decomposing litter, are strongly influenced by the chemical composition of the litter. Litter higher in tannins and lignin decomposes more slowly. Lignin/Nitrogen ratio Decomposition rate

31 Bill Shakespeare, secondary chemist


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