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Notes from Sept. 9th

by: Meghan Shah

Notes from Sept. 9th HORT 3440

Meghan Shah
GPA 3.78

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In class notes on secondary metabolites
Herbs, Spices, and Medicinal Plants
James Affecter
Class Notes
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This 4 page Class Notes was uploaded by Meghan Shah on Tuesday September 13, 2016. The Class Notes belongs to HORT 3440 at University of Georgia taught by James Affecter in Fall 2016. Since its upload, it has received 4 views. For similar materials see Herbs, Spices, and Medicinal Plants in Biology/Anthropology at University of Georgia.

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Date Created: 09/13/16
Notes from Sept 9: Secondary Metabolites  Primary vs. Secondary Metabolites in Plants ○ Carbohydrates, proteins, lipids, and nucleic acids are essential to life  ▪ they’re called primary metabolites because they occur in the major metabolic  pathways and processes of plants (respiration, photosynthesis, cell division,  etc.) ○ Plants produce many other compounds via other metabolic pathways ▪ These are called secondary metabolites. ▪ They serve diverse functions in plants and are often the source of a plant’s  medicinal or culinary value ▪ Many plant toxins belong to this group too. ○ At one time it was thought that these compounds were waster productions of  metabolism. ○ We now know many of them serve important ecological functions in plants,  including: ▪ attracting pollinators for fruit/seed dispersal ▪ inhibiting bacterial and fungal pathogens  ▪ deterring grazing animals and herbivorous insects ▪ Inhibiting the growth of competing plants  Secondary metabolites can be grouped into four large classes of compounds: ○ Terpenes, Phenolics, Alkaloids, and Glycosides. ○ Terpenes ▪ Hydrocarbons – compounds containing only carbon and hydrogen ▪ Include essential oils, resins, and polyterpenes. ▪ Range greatly in size and structure ▪ Resins are used in the production of:  Pharmaceuticals  Rosin  Turpentine  Varnishes  Insecticides  Chewing gum  Oil­based paints ▪ Polyterpenes   include the elastic compounds found in many (new world) plants  Also the natural rubber from the rubber tree (Hevea brasiliensis) ▪ Taxol is a terpene obtained from the Pacific Yew ▪ Carotenoid pigments – the red, yellow, and orange pigments found in plants,  like tomatoes – are terpenes too.  But they’re usually classified as primary metabolites ▪ In essential oils, terpenes provide the flavor and aroma of many herbs and  spices, as well as the scents used in perfumes. ○ Phenolics ▪ All contain one or more aromatic benzene rings (a ring of 6 carbon atoms and 6 hydrogen atoms attached) with one or more hydroxyl (OH) groups ▪ Large and diverse category of compounds  Range from small molecules to large & complex macromolecules ▪ The natural browning of cut surfaces of apples and potatoes are caused by  the interaction of phenolic compounds with oxygen in the air ▪ Some phenolic compounds are essential oils, like clove oil and bergamont  (used to flavor Earl Grey tea) ▪ Flavonoids   Include water soluble pigments known as anthocyanins, found in red  cabbage and many flower petals ▪ Tannins  Utilized as stains, dyes, inks, and tanning agents for leather  Believed to function in plants by discouraging herbivores  Important flavor compounds in tea, red wine, and many fruits ▪ Lignin  Actually a primary metabolite found in the cell walls of many plants  Gives wood its hardness and strength  Composed of thousands of phenolic molecules  Urushiol – contact poison in poison oak and poison ivy that causes the  itchy, blistering rash  Tetrahydrocannabinol (THC) – a phenolic resin and the active ingredient  in marijuana ○ Glycosides  ▪ Compounds made up of a sugar (usually glucose) and a non­sugar molecule ▪ When these compounds are metabolized by animals, the sugar splits off and  the non­sugar component becomes physiologically active.  The non­sugar component is typically a terpene, steroid (a type of lipid), or phenolic compound ▪ Saponins  Combination of a sugar and a steroid  Forms a soapy lather when mixed with water  Used in shampoos and detergents  Bitter tasting; cause gastric upsets  Soapwort – Saponaria officinalis  Saponins from yams are the source of steroids used in the manufacture of human sex hormones  10 species of Dioscorea (yams) are important food crops in the tropics  They are vines that produce large tubers that are rich in starch, some  with additional protein ­ The saponins of yams are a type of steroid that has been used to  make human sex hormones and cortisone ← Early research on the development of the birth control pill was  based on diosgenin extracted from yams and shown to inhibit  ovulation ← Today, synthetics have largely replaced natural compound in  the production of birth control pills ▪ Cardiac Glycosides  The active portion of the molecule is similar to a steroid  These affect the heartbeat   Fatal if consumed in large doses  Digitoxin from foxglove is an important medicine for congestive heart  failure ▪ Cyanogenic Glycosides  These release deadly hydrogen cyanide (HCN) when metabolized   Cassava is the 6  most important food crop in the world, but it’s edible  tubers can cause death by cyanide poisoning if they’re not processed  to remove the toxins by: ­ Soaking ­ Boiling ­ Fermenting ­ Other methods ○ Alkaloids ▪ Nitrogen­containing secondary metabolites that are synthesized by/from  various amino acids ▪ Known for their effects on mammalian physiology, especially the central  nervous system  Many are similar to neurotransmitters found in the brain  Most are considered psychoactive ▪ Some are stimulants:  Caffeine   Cocaine  Ephedrine ▪ Some are depressants:  Morphine  Codeine ▪ In high doses, many alkaloids are deadly poisons, such as the nicotine in  tobacco  ▪ Some alkaloids, such as mescaline, the tropane alkaloids, and the ergot  alkaloids, are hallucinogenic  The release of volatile Sulphur­containing compounds when cells are damaged is  the reason we value many plants in the mustard and onion families. ○ It explains the delayed reactions when we chew mustard seeds ○ Isothiocyanates are sulphur­containing molecules found in the mustard fam ▪ The substrate compound, glucosinate, and the enzyme, myrosinase, are  stored within different compartments of the cells  When cells are broken or crushed, like when we chew them, the substrate  and enzyme are brought into contact and they reaction, producing the  spice flavor compound isothiocyanate ○ The pungent flavor of many plants in the onion fam are due to the presence of  various volatile sulphur compounds that are released when the tissues are cut,  and the substrate compound and enzyme are brought into contact ▪ Garlic is in the onion family; the active ingredient in garlic is allicin.   ▪ The chemically similar active ingredient from onions is known as “the  lacrimatory factor”  Cutting onions under water will wash away some of the lacrimony factor  Cutting onions cold will retard the enzyme activity  After digestion, the sulphur compounds are transported by the blood  stream into the lungs, where they diffuse into exhaled air  That gives you garlic breath  Summary of Major Groups of Secondary Metabolites ○ Terpenes – essential oils, resins, polyterpenes ○ Phenolics – flavonoids, tannin, lignin ○ Glycosides – saponins, cardiac glycosides, cyanogenic glycosides ○ Alkaloids – sulphur­containing compounds, isothiocyanates (mustards),  alliin/allicin (onions)  Our ability to taste certain compounds is genetically determined ○ It all depends on which alleles you’re carrying in your DNA  Flower//Plant Meanings for “Tussie Hussies” ○ Bachelor’s button – hope in love ○ Jasmin – availability ○ Sweet Willian – gallantry ○ Chrysanthemums – cheerfulness ○ Hyacinth – playfulness ○ Basil ­  hatred ○ Aloe – sorrow, bitterness ○ Evening Primrose – inconstancy ○ Hop – injustice ○ Marigold – mental anguish ○ Hellebore – female inconstancy


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