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Glycosides Sugar + non-sugar

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1 Glycosides Sugar + non-sugar
In the body they are broken down by enzymes or acids into: sugars= glycone/ water soluble non sugar= aglycone/ active portion Aglycone may be an alcohol, sulfur or phenol compound.

2 Classification of glycosides
Based on the nature of the aglycone Aglycones can be: phenols quinones terpenes steroids Huge variety of medicinal activity from one glycoside to the next.

3 How are they broken down?
Pro-drugs: glycosides remain inactive until they are hydrolized in the large intestines by the help of specialized bacteria This leads to the release of the aglycone which is the active constituent The body can absorb some aglycones better than others depending on the herb

4 Glycosides and Plant Families
Brassicaceae- glucosinolates Rosaceae- cyanogenic glycosides Scrophulariaceae- phenylpropanoid glycosides Asteraceae- phenylpropanoid, flavinoid glycosides Polygonaceae- anthraquinones

5 Cyanogenic Glycosides
Wild Cherry

6 Cyanogenic glycosides
Colorless plant constituent Hydrogen cyanide was first isolated from Prussian blue dye aglycone contains nitrogen BREAK DOWN: Cyanogenic glycoside hydrocyanic acid (prussic acid)  cyanide

7 Cyanogenic Glycosides
Cyanogenic glycosides are found in pits and seeds of apples, apricots, peaches, plums and elderberries leaves and stems. Their function in plants is not really known but they are suspected to be anti-feedants.

8 Cyanogenic glycosides
Main cyanogenic glycosides Amygdalin- found in bitter almonds and peach kernels (Chinese herb) - used in to make Marizpan flavoring in cooking. 2. Prunusin- found in wild cherry bark 3. Sambunigrin- from the leaves of the elder tree, Sambucus nigra Other food plants that contain cyanogenic glycosides include flaxseed and manioc. Manioc root must be boiled and the water discarded in order to remove the toxins.

9 Cyanogenic glycocides-toxicology
In large doses hydrogen cyanide (hydrocyanic acid) inactivates respiratory enzymes, shuts down the CNS and leads to death. However large doses of raw plant material are needed for toxicity to occur. Our bodies can nuetralize cyanides and eliminate them through the urine. Cyanogenic glycosides are broken down slowly and are easily detoxified by the body in smaller doses. 500mg three times a day to produce a toxic effect, which is A LOT!!- there are 4-9 mg hydrogen cyanide per bitter almond You would have to eat 150 bitter almonds a day for a toxic effect!!!

10 Cyanogenic Glycosides: Properties
Sedative and expectorant to the respiratory tract. Wild Cherry Bark (prunus serotina) is a classic prunasin conataining respiratory herb for dry irritable coughs. Apricot kernels in Chinese medicine are used for coughs and asthma. Cooling Hydrocyanic acid cuts down heat at a cellular level. Ex- peach, apple and pear are all cooling fruits that contain Cyanogens. Anti-cancer Amygdalin/Laetrile- has been researched as an anti-tumor remedy.

11 Cardiac Glycosides Digitalis purpurea

12 Cardiac Glycosides Cardiac glycosides have a long history of use in herbalism The famous cardiac glycoside, digitoxin, was isolated in 1785 by William Withering. He found out about the use of foxglove by an elder lady herbalist in his village using it for CHF (dropsy). Of course she gets no credit! Digitoxin and other cardiac glycosides from plants day play a large role in modern medicine.

13 Cardiac Glycosides Found in many medicinal plants such as Digitalis purpurea and lilly of the valley (Convallaria majalis) Direct action on the heart supporting its strength and rate of contraction when it is failing.

14 Cardiac Glycosides- Plant protection
Plants and animals create cardiac glycosides as a strategy for protection against being eaten by other creatures. Some animals, like monarch butterflies, have evolved immunity to the toxins. They consume plants like milkweed (Asclepias syriaca) that are high in cardiac glycosides and store the toxins in their tissues. This makes them poisonous to other predators Used as arrow poisons by hunters

15 Cardiac Glycosides- chemistry
Steroidal structure- 3 six carbon rings and one five-carbon ring The sugar portion of the cardiac glycoside is important in the absorbtion and distribution in the body. The aglycone portion is important in binding to Na/K pumps in the heart cells

16 Cardiac Glycosides CONDITIONS: Used in arrhythmias and congestive heart failure(dropsy) In the past dropsy was the only sign of heart failure. Dropsy (CHF) fluid accumulation in the lower limbs and abdomen due to the heart not being strong enough to handle venous return. ACTIONS: increase the force and speed of contraction Inhibit sodium potassium pump leading to a rise in intracellular calcium which increases contraction of the heart. Decrease heart rate Slows conduction velocity in the pace maker- used for arryhthmias

17 Cardiac glycosides Toxicity- Narrow therapeutic window. The therapeutic dose is not much smaller than the toxic dose. Too high of a dose can make the pace maker more sensitive and lead to atrial fibrillation. Cardiac Glycosides are antagonistic to Potassium. If person is low in K+ they will be more likely to have digitalis intoxication. Taraxicum in combition helps to replenish K+ Digitalis Intoxication- nausea, vomiting, diarrhea, vision disturbances, headache, arrhythmias.

18 Cardiac Glycosides Cardiac remedies in other than drop doses should be used with discretion. Digitalis lasts a long time in the body and its effects are cumulative. Half life is over 6 days! Convallaria should be considered before digitalis because it has a lower toxicity

19 Cardiac Glycosides Plants containing cardiac glycosides include:
Digitalis purpurea- Used for CHF and edema Apocyanum cannabinum (Dogbane) Strophanthus hispidus (Kombe Seed) Adonis vernalis (False Hellibore) Urginea Maritima (Squill) Convallaria margalis (Lily of the Valley)

20 Isothiocyanate glycosides

21 Isothiocyanate glycosides (Glucosinolates)
Found in the Brassicaceae (Mustard) Family. Sulpher link between the glycone and the aglycone. Sulpher is what gives the brassicas their pungent quality. ( Horseradish clears the sinuses, mustard oil opens the lungs) In plants they are used as protection against microbes that disrupt their cell walls.

22 Isothiocyanate Glycosides
Therapeutic Actions: Culinary- black and brown mustard seeds used in cooking are high in nutrients, stimulate digestion. Rubefacients- mustard seed oils act as irritants when applied topically, causing local vasodilation Mustard poultices over the lungs break up congestion. Decongestant for the sinus and bronchial conditions (horseradish, onion and garlic). Large doses may have an emetics effect.

23 Isothiocyanates- goiterogens
When consumed in excess they inhibit pumping of iodine into the thyroid follicles. This leads to goiter formation especially in those who are iodine deficient. pertains more to people who are very iodine deficient like in parts of Asia or central Africa. Isothiocyanate botanicals are low enough not to cause a problem.

24 Isothiocyanate glycosides- Antitumor
Glucobrassicin is widely distributed amongst the Brassicaceae family Glucobrassicin produces indoles when broken down. Indole-3-carbinol and diindoylmethane (DIM) Indoles are known for their ability to induce tumor inhibiting enzymes. Thus are protective against cancer. Indoles do not break down under heat.

25 Isothyocyanate Glycosides
Toxicology: External use of should not be sustained for longer than two weeks because of irritating effects. mustard seed oils should never be used internally or externally because it toxic to the skin and mucus membranes.

26 Saponins Wild Yam (Dioscorrea spp.)

27 Saponins- Definition Saponins are glycosides with foaming characteristics. Saponin- comes from “sapo” in Latin which means soap. Historically soap was made from the soapwart plant. In plants they are anti-feedants and protect plants against microbes and fungi

28 Saponins- synthesis Synthesized from acetyl CoA via the mevalonic pathway (similar to cholesterol in animals) Major economic importance: saponins are used to synthesize pharmaceutical steroids (corticosteroids, estrogens, progesterone and progestins) Agave, fenugreek and wild yam root are examples of plants used for their steroidal properties in the laboratory. Human body doesn’t possess the gut flora to interconvert plant steroids to human steroids. Steroidal saponins from agave have antibacterial, cytotoxic and contraceptive effects. Diosgenins in fenugreek inhibit cholesterol absorption and synthesis. Sapogenins found in fenugreek also lower serum triglycerides, total cholesterol (TC), and low-density lipoprotein cholesterol. Diosgenin and trigogenin (saponins) are chemically similar to estrogen.

29 Saponins- classification
Consist of polycyclic aglycones attached to one or more sugar side chains. Two subcategories of saponins Triterpenoid: pentacyclic structure Steroidal saponins (phytosterols): tetracyclic structure Licorice is a Pentacyclic triterpenoid

30 Saponins= Suds The foaming ability of saponins is caused by the combination of a hydrophobic (fat soluble) aglycone along with the the sugar which is hydrophilic (water loving). Allows lipids to dissolve in water Emulsification in foods that allow water and fat to mix. They have a detergent effect on the skin and the mucus membranes.

31 Saponins Wound healing herbs contain saponins such as calendula.

32 Saponins- Actions Saponins are bitter or acrid in taste
If injected intravenously they cause hemolysis. Use only orally! Destroy the membranes of red blood cells. Lower cholesterol: Because they are structurally similar to cholesterol they interfere with cholesterol absorption Increase cholesterol excretion into the bile which then gets excreted through the feces. Ex. Trigonella foenum-graecum (fenugreek)

33 Saponins- Actions Medicinally they have many uses:
anti-inflammatory: Licorice, wild yam anti-viral: licorice, ashwaganda Digestive: licorice, Expectorant: lobelia, squill Adaptogenic: licorice, gensing,ashwaganda

34 Saponins- reflex expectorants
Acrid and flavor of saponins make them reflex expectorants Reflex expectorants irritate the upper digestive tract causing emesis. This irritation also causes a reflex action via the vagus nerve to promote expectoration. Historically herbalists have used emesis to clear the lungs in chronic bronchitis

35 Saponins- reflex expectorants
Lobelia inflata Cephaelis ipecacuanha (Ipecac) Urginea maritima (Squill) Verbasum thapsus (Mullein flowers) Viola spp (Violet flowers) Glycyrrhiza glabra (licorice)

36 Steroidal Saponins Dioscorea villosa (Mexican wild yam) root
Diosgenin: saponin aglycone NOT PROGESTROGENIC in the body. Complex chemical reactions in the laboratory make it progestrogenic. Naturally it is antispasmodic and anti-inflammatory. Human body cannot convert diosgenin into hormones.

37 Steroidal Saponins Panax gensing (Asian) and P.quinquefoium (American gensing): Gensenosides: immunomodulating, anti-stress, anti-dementia Saponins foam and enhance absorption of other plant constituents. Withania somnifra (Ashwaganda) root Withanolides: calming and immunomodulating Panax gensing

38 Triterpenoid Saponins
Glycyrrhiza glabra (Licorice) Glycyrrhizin- reduces toxicity of other saponins anti-inflammatory, antiviral, immunomodulating, hepatoprotective, anti-ulcer Used as a synergizer in herbal formulas rendering other ingredients more bioavailabe Bupleurum falcatum Hepatoprotective, antiviral, immunostimulating

39 Saponins in medicine making
Saponins are poorly bioavailable in the human body. Other plant constituents present in the plant aid in assimilation of saponins. Saponin rich plants influence absorption of other plant constituents: Help lipophilic constituents of plants be absorbed Saponins in high doses can cause gastric irritation. Better if they are taken with food. Mostly soluble in dilute ethanol (30%), water and lipids

40 Alkaloids

41 Alkaloids Have had a major impact on humanity
Examples are caffeine, morphine, ephedrine, atropine, cocaine and many more… Henbane contains hyoscamine which was known as a flying ointment. Natives using peyote, iboga in africa, south americans and ayahuasca, coca, cacao

42 Alkaloids Most potent of all plant constituents
alkaloids are seen in pharmaceuticals such as codeine, morphine, atropine, pseudoepinephrine and vincristine. High doses will cause vomiting, diarrhea, immediate central nervous system symptoms and death. Important for the herbalists to be careful with herbs that have a high alkaloid content. Many herbs that contain alkaloids such as berberis and California poppy are low toxicity.

43 Alkaloids in the plants
Why do plants have alkaloids? We don’t know, there are just theories… Unclear alkaloids are a way for plants to excrete excess nitrogen, like mammals excrete nitrogen though urea in the urine Alkaloids serve as defenses from predations Alkaloids are a way for the plant to store nitrogen which is hard element to come by.

44 Alkaloids in plants Alkaloids are common in plants: 10-15% of all plants have some kind of alkaloid May be found in roots, leaves, bark, fruit or seeds. Over 40 different alkaloids can be present in one plant, like Vinca major. Vinca Major

45 Alkaloids- chemistry The word alkaloid is derived from vegetable alkali, which refers to their alkaline nature due to the presence of nitrogen Alkaloids are best classified according to their biosynthetic origen. Most are synthesized by the plant from amino acids Psuedoalkaloids- derived from terpenes Difficult to classify alkaloids. Some have nitrogen others don’t, some aren’t even alkaline. For example, mescaline, ephedrine and muscarine don’t have nitrogen. Alkaloids colchicine and ricinine aren’t alkaline.

46 Alkaloids-chemistry General characteristics  alkaline
Contain a nitrogen Part of a heterocyclic ring system Berberine

47 Alkaloids- Properties
Most are white in color when extracted, except berberine alkaloids which are yellow Bitter in taste Soluble in alcohol Tinctures (45% ethanol) are very effective at extracting alkaloids Acetracts extract alkaloids well, such as apple cider vinegar. Less soluble in water This may be a good way to deliver medicine if there is a potential for giving too high of a dose of alkaloids.

48 Alkaloids- Properties
Irreversibly precipitated by tannins. Alkaloid containing medicines should not be tinctured with tannins, unless you wish to counteract the alkaloid. If you want to mix a tincture that has both alkaloids and tannins use 10% glycerine to the tincture. Black tea (Camelia sinensis), cranesbill (Geranium maculatum) or witch hazel (Hamamelis virginiana) are the three remedies for alkaloid poisoning

49 Alkaloids- Actions Analgesics/narcotics- morphine Mydriatics- atropine
Hypertensives- ephedrine Hypotensives- reserpine Stimulants- caffeine, strychnine Antimicrobials- berberine Anti-cancer- vinblastine

50 Alkaloids Many different groups of alkaloids exist
The most common groups that we will be covering in this class are: Tropane Alkaloids- Belladonna, Henbane ect Isoquinoline- California poppy, berberis Pyridine- Tobacco, Lobelia Pyrrolizidine- Comfrey, Western Coltsfoot Indole- Peyote, Iboga Purine- Cacoa, Caffeine

51 Tropane Alkaloids Synthesized from amino acids ornithine or proline.
Mostly Solanaceae family Atropa belladona – Deadly nightshade Datura stramonium- Thornapple Hyoscymus niger- henbane Mandragora officianialis- mandrake Erythroxylum coca - Bolivian coca

52 Tropane Alkaloids Anticholenergics (inhibit parasympathetic nervous system) Smooth muscle relaxants Atropine: dilates pupils, anti-emetic, decreases salivation Hyoscamine: bronchial and intestinal antispasmotic, hallucinagenic Cocaine: Anesthetic (novacaine), narcotic

53 Isoquinoline Alkaloids
Synthesized from amino acid tyrosine Alkaloid Berberine- Hydrastis canadensis and Mahonia root Bitter digestive stimulant GI tonic Anti-microbial Immune stimulant Hydrastis canadensis

54 Isoquinoline alkaloids
Papaver somnifera (opium poppy): papaverine, morphine, codeine Analgesic, antitussive, seditave narcotic Corydalis spp : corydalin Analgesic Ipecac root: emetine Emetic in high dose, reflex expectorant in low dose, anthelmintic Sanguinaria candensis (Bloodroot):sanguinarine Antimicrobial, antineoplastic

55 Isoquinoline alkaloids
Sanguinaria canadensis

56 Isoquinoline Alkaloids
Papaver somnifera

57 Pyridine alkaloids Derived from the B vitamin nicotinin acid
Nitrogen atoms in six-membered benzene rings

58 Pyridine Alkaloids- Actions
Lobeline (lobelia inflata leaf): expectorant, smasmolytic, nicotic agonist Nicotine (Nicotiniana tabacum leaf): Nicotinic agonist, addictive Trigonelline (fenugreek seed): hypolipidemic (lowers blood cholestrol) Piperine (Piper longum fruit): Increases gut permeability, hepatoprotective, used in combination with other herbs to increase efficacy

59 Pyrrolizidine alkaloids
Synthesized from ornithine in plants Ingested by butterflies to protect them from invadors Asteraceae and Boranginaceae families contain PA- ex) comfrey, echinacea and arnica Herbal medicine containing PA are contraversial and have been banned from use in Australia. Only PA with unsaturated bases are hepatotoxic. Asteraceae herbs including echinacea and arnica have saturated PA which are non-toxic.

60 Pyrrolizidine Alkaloids
Hepatotoxic in large doses PA can cause hepatic venous occlusive disease if large doses are ingested When metabolized in liver they cause DNA damage to liver cells which then fibrose around the venules of the liver. Jaundice and liver failure ensue. PA don’t affect everyone equally. Some people may not have sufficient levels of liver enzymes to metabolize PA. Intake of over 3 gm/day of PA can cause liver damage within three months. PA become dangerous after undergoing metabolism by P450 enzymes in the liver. The toxic byproduct (alkylating pyrrole ester) attack DNA, damaging hepatocytes. Hepatocytes are destroyed and fibrosis occurs.

61 Pyrrolizidine Alkaloids
Symphytum off. (Comfrey) has PA Mucilagenous, anti-inflammatory, heals ulcers internally and externally. Has been condemned as toxic by many. Few cases of injury have been reported and of those cases people who were poisoned ate the root which is much higher in PA than the leaves. Glycyrrhizin (saponin from licorice) has been found to protect the liver from PA

62 Pyrrolizidine Alkaloids
Other plants that contain PA: Tussilago farfara (Eastern coltsfoot) Sencio spp (Life root) Borago officianlis ( Borage) Tussilago farfara

63 Pyrrolizidine Alkaloids
Senecio spp. (Liferoot or Ragweed)

64 Indole Alkaloids Large number of medicinal alkaloids are found in this group Derived from tryptophan or tryptamine in plants. Contain 2 nitrogens and often involve multiple rings. Form the basis of several hallucinogenic and pharmaceutical drugs.

65 Indole Alkaloids Apocynacea family- Rauwolfia, Vinca, Catharanthus, Iboga Fungus family- psylocybin mushroom and ergotimine

66 Indole Alkaloids- Reserpine
Reserpine found in Rauwolfia serpentina has been used in Aryuvedic medicine as a hyptotensive, seditave and tranquilizer. Reserpine temporarily inhibits noradreniline and depletes the amino acids in the central nervous system. Hypotensive effects have a slow onset and their duration is long. Use cautiously depression and severe hypotension are indications of overdose. Reserpine blocks the transport of catecholemines (seratonin, NE and dopamine) from their receptors on the nerve endings. Catecholemines are the nuerotransmitters responsible for increasing heart rate, force of contraction of the heart and peripheral resistance.

67 Indole Alkaloids Cantharanthus roseus (Madigascar Periwinkle)
Contain vinblastine and vincristine- antineoplastic used in chemotherapy for childhood luekemia and non-Hodgkin’s lymphoma Vinca minor, major (Common Periwinkle) Vincamine- anti-hemorrhagic and astringent. Does not contain the anti-cancer alkaloids that cantharanus has. Claviceps purpurea (Ergot) Ergotamine- fungus grows on rye. Migraine relief St.Anthony’s Fire- epileptic convulsions and spasms. LSD is derived from ergot. Similar compounds found in Ipomoea spp. (Morning Glory)

68 Other Indole Alkaloids
Pausinystalia yohimbe ( Yohimbe) Yohimbine- Aphrodesiac and nerve tonic Gelsimium sempervirens (Yellow jasmine) Gelsemine- heart tonic, nerve seditave, toxic. Strycnhos nux vomica (Nux Vomica) Strychnine- powerful CNS stimulant in low doses. Toxic Banisteriopsis caapi ( Ayahuasca) Harmine- entheogenic

69 Indole Alkaloids Banisteriopsis caapi

70 Purine Alkaloids Caffeine, theobromine (chocolate), theophylline (from cacao and tea) Methyl xanthines- Derived from the purine nucleotides adenine and guanine with attached methyl groups. Mild stimulants and bronchodilators Theophylline is a drug used for respiratory distress and asthma.

71 Purine Alkaloids Cacao Tree

72 Purine Alkaloids Increase the rate of cardiac contraction
Increase alertness and induce digestive enzyme activity in the GI They act by stimulating the Central nervous system and prolonging the life of hormones, such as adrenaline.

73 Bitters

74 Why are bitters important?
Increase the appetite: Have been used in aperitifs or to induce appetite in convalescence Increase digestive secretions Low enzymes or stomach acid aid in depressed digestive ability and leads to proteins from food penetrating into the wall of the gut. Increases stomach and pancreatic enzyme secretions and aid the body in breaking down food.

75 Bitters Protect gut tissue: Increase the tone of the lower esophageal sphincter Prevent reflux or heart burn, hiatal hernia or esophageal irritation. Promote bile flow: reduces toxic load on liver by flushing out toxic accumililations by increasing bile. Increases bicarbonate from gallbladder and thins bile Gallstone and gallbladder disease

76 Bitters Indicated for symptoms of poor digestions
Belching, loss of appetite, constipation, bloating and nausea after eating. Controversy weather bitters are safe to use with people who have ulcers because too much acid could aggravate the ulcer Bitters increase secretions of bicarbonate from the pancreas which protect the stomach from acid.

77 Some plants containing bitters
Achillea millefolia (Yarrow) Artemesia spp. (Wormwood, mugwort..) Arctium lappa (Burdock) Tanacetum (Feverfew) Taraxicum ( Dandilion) Gentiana lutea (Gentian) Centaurium minus (Centaury) Berberis spp (Oregon Grape) Hammamelis spp (Witch Hazel) Humuls lupus (hops) Tussilago farfara ( Coltsfoot)

78 Acids Weak acids constitute a main part of all plant material
Acids we will cover Unsaturated fatty acids Formic Acid Oxalic Acid Citric Acid Other acids that occur in plants are Acetic, succinic, benzoic and tartaric

79 Unsaturated Fatty Acids
Found universally in plants and less so in animals. Linolenic and arachadonic acids- found in seeds and reproductive tissues of the plants Linolenic acids- found in the green tissues of plants PUFAs (Polyunsaturated fatty acids) are vitally necessary in the diet = ESSENTIAL FATTY ACIDS

80 Essential Fatty Acids Why are they so important?
Build and repair cell membranes Form raw material for prostaglandin production in the body Prostaglandins are important in smooth muscle contractions, inflammatory mediators, and raise blood pressure Example of PUFA- Evening Primrose (Oenothera biennis) has gamma linolenic acid

81 Evening Primrose Used as an anti-inflammatory conditions like rhuematoid arthritis, PMS and eczema

82 Formic Acid The smallest organic acid and the most corrosive to the skin….just like fire ants! Used in counterirritants and vesicants Found in red ants Formic Acid is the sting in stinging nettles Oxidizes and is inactive after being exposed to heat. Cook your nettles to eat them!!

83 Oxalic Acid Forms insoluble salts with minerals such as calcium.
Found in foods such as spinach, beets and parsley Found in the dock and rhubarb families. Oxalic acid bound to iron and calcium is what makes Yellow Dock so highly nutritious. Care needs to be taken to not consume too many oxalate rich foods if there is a history of oxalate kidney stones.

84 Citric Acid Found widely in fruits and berries, especially citrus fruits Cleansing in the body Alkalinizing effect: citrus breaks down into bicarbonate once in the stomach Alkalinizing effect in mouth provides the environment inhospitable to bacteria Increases bile flow from the liver Explains use of lemon for gallbladder cleanses

85 Thank you

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