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Secondary metabolites

Secondary metabolites. Glycosides Tannins Alkaloids. І. Glycosides - the sugar (glycoside) and the non-sugar (aglycone) moieties. glucosidases. glycoside. Sugar residue (glycol) + aglycone. Glycosides types : Anthraquinone Phenolic 3. Pigment 4. Coumarin 5. Cardio glycosides

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Secondary metabolites

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  1. Secondary metabolites • Glycosides • Tannins • Alkaloids

  2. І. Glycosides -the sugar (glycoside) and the non-sugar (aglycone) moieties. glucosidases glycoside Sugar residue (glycol) + aglycone

  3. Glycosides types : • Anthraquinone • Phenolic 3. Pigment 4. Coumarin 5. Cardio glycosides 6. Saponins 7. Iridoids 8. Tioglycosides 9. Cyanogenic

  4. 1. Anthraquinone glycosides - withaglycone anthracene and its derivatives • Aloe - emodin (Aloe vera - Aloe, Liliaceae) • Rheine (Rheum officinale - Rhubarb Polygonaceae) • Hypericin (Hypericum perforatum - St. John's wort, Hypericaceae) • Chrysophanol (Senna obtusifolia -senna, Fabaceae) Action: theyare the stimulant cathartics and exert their action by increasing the tone of the smooth muscle in wall of the large intestine.

  5. 2. Phenolic glycosides - with aglycone benzene ring combined with an alcohol. Gallic acid - in bark of oak (Quercus sp., Fagaceae), leaves of tea (Thea sinensis, Theaceae), tanning sumac - Rhus coriaria, Anacardiaceae) Structural formula of phenol Caffeic acid - in the resin of coniferous, poplar buds

  6. Ellagic acid - Rubus idaeus (raspberry, Rosaceae), R. caesius (blackberry) Salicylic acid - bark of white willow (Salix alba, Salicaceae)

  7. Arbutin- bearberry(Arctostaphyllos uva-ursi, Ericaceae Family) Eugenol – clover genus Trifolium (Fabaceae Family) Gossypol - cotton(Gossypium hirsutum, Malvaceae Family) Action :antiseptic, anthelminitic & caustic activity

  8. 3. Pigment glycosides - flavonoids and anthocyanins Flavonoids glycosides (flavonoids) - with aglycone flavone or isoflavone gives yellow color of plant parts

  9. Action: antioxidant, anti - inflammation, antibacterial, cardiovascular diseases - inhibit coagulation and thrombus formation

  10. Anthocyanins (anthocyans) - with aglycone anthocyanin • a subgroup offlavonoids, which give plants their distinctive colors- blue to violet • present in the vacuolar sap of the epidermal tissues of flowers and fruit • formation depends on the breakdown of sugars in the presence of bright light • found In flowers& fruits - to atract pollinators and eaters • in photosynthetic tissues (leaves and stems) - a "sunscreen", protecting cells from high-light damage by absorbing blue-green and ultraviolet light, thereby protecting the tissues fromphotoinhibition (high-light stress).

  11. Cyanidin - grapes, blueberries, cherries Malvidin – common mallow (Malva sylvestris, Malvaceae) Delphinidin– larkspur (Consolida regalis, Ranunculaceae) Pelargonidin –pelargonium (Pelargonium sp., Geraniaceae) Peonidin –peony(Paeonia peregrina,Paeoniaceae) The sugar-free molecule - is called anthocyanidins Action: increase the elasticity of capillary blood vessels - bleeding diuretic, antispasmodic, stimulate Cardio Vascular System (CVS), antioxidants.

  12. Autumn coloration (including red) - the result of breakdown of green chlorophyll, which unmasks the already-present orange, yellow, and red pigments(carotenoids, xanthophylls, and anthocyanins). 

  13. 4. Coumarin glycosides - with coumarin aglycone Coumarin - green shield bug (Anthoxantum odoratum, Poaceae), lady's bedstraw (Galium odoratum, Rubiaceae) Dicoumarol - Sweet clover (Melilotus alba & M. Officinalis – Fabaceae) Psoralen – fig(Ficus carica, Moraceae), parsley (Apium graveolens, Apiaceae) Pastinatsin, Bergapten – parsnips(Pastinaca sativa, Apiaceae) Umbelliferone – carrot (Daucus carota, Apiaceae), coriander (Coriandrum sativum, Apiaceae) Aesculin – in the bark of Aesculus hippocastanum – horse chesnut (Hippocastanaceae) Coumarin molecule

  14. Action: • protect skin from UV light • Anticoagulant – inhibit hepatic synthesis of vitamin K-dependent coagulation factors • antifungicidal properties

  15. 5.Cardiac glycosides – increase cardiac output by increasing the force of contractionof the cardiac muscle Cardiac glycosides – types: - Cardenolides: • Strophanthin, ubain (Strophantus combe, Erythroxilaceae) • Digitoxin, digoxin (Digitalis purpurea, Scrophullariaceae) • Oleandrin (Nerium oleander, Apocynaceae) • Convalozid, Convalatoxin (Convallaria majalis, Liliaceae) • Adoni toxin (Adonis vernalis, Ranunculaceae) • Periplocinum (Periploca graeca, Apocynaceae) - Bufadienolides: • Helleborine (Helleborus odorus, Ranunculaceae) • Scilaren(Allium maritimum, Liliaceae) Action: diuretic, emetic, insecticide

  16. Initial inhibition of potassium sodium(K/ Na) ATPase - increasing on  intracellular sodium (Na) concentration 3 Na = 1Ca • Secondary activation of potassium - sodium – exchange pump in the cell membrane • increase the concentration of intracellular free calcium

  17. 6. Saponin glycosides (saponins)– with sapogenin aglycone(С27) or triterpene (С30). Molecule of sapogenin

  18. Saponins types: Steroidal saponins: Ruskogenin - mouse thorn (Ruscus aculeatus, Liliaceae) Diosgenin– Dioscorea sp. (Dioscoreaceae), Trigonella sp. (Fabaceae) Usage: the basis for the synthesis of steroid hormones and derivatives of cortisone Triterpenic saponins: - Aescin - horse chestnut (Aesculus hippocastanum, Hyppocastanaceae) • Saporubin - soapwort (Saponaria officinalis, Caryophyllaceae) • Glycyrrhizin - liquorice(Glycirhiza glabra, Fabaceae) • Primula saponin - Primrose(Primula officinalis, Primulaceae) • Header saponin – ivy (Hedera helix, Araliaceae) • Panax saponin - Ginseng (Panax ginseng, Araliaceae) Action: expectorant

  19. 7. Iridoid glycosides - with aglycone iridoids (С10). Iridomyrmex purpureus Iridoidmolecule

  20. Types of iridoid glycosides: Aucubin - Plantain - Scrophulariaceae family (Plantaginaceae) Harpagoside - Lamiaceae family (Lamiaceae) Amarogentin, gentiopicrin(secoiridoids) - Gentianaceae family (Gentianaceae) Valtrate, isovalerate (valepotriats) -Valerianaceaefamily (Vallerianaceae) Asperulozid - RubiaceaeFamily Action: appetite exciting, sedative, anti-inflammatory

  21. 8. Tioglycosides – sulfur containing glycosides Mustard glycosides - Brassicaceae family Sinalbin - white mustard (Sinapis alba) Sinigrin - black mustard(Sinapis nigra) Action:bile eviction, appetite exciting, diuretic, expectorant

  22. 9.Cyanogenic glycosides– withaglycone cyanidegroup Hydrogen cyanide – final product of cyanogenic glycosides degradation A cyanide group - construction

  23. Amygdalin - in representatives of Rosaceae family - cherry, almond, apricot, apple

  24. Prunazin - Scrophulariaceae family(Scrophullariaceae) Sambunigrin – Rubiaceae family (Rubiaceae) – Sambucus nigra Linamarin– Linaceae family (Linaceae) Durin– Poaceae family (Poaceae) – Sorghum bicolor Inflorescence of Sambucus nigra Contents of Cyanicogenic glycosides in Eucalyptus globulusleaf Action:laxative, sedative, antitumor

  25. ІІ. Tannins -complex nitrogen- free organic compounds with many hydroxyl groups Molecule of tannic acid

  26. Basic property of tannins - precipitation of proteins

  27. Types of tannins: • Hydrolyzable tannins - with a strong astringent action 1а. Gallotannins – Gallic acid , digallic acid 1 b. Ellagotanins - leaves of sumac, madder, alder, walnut, oakand oakgalls

  28. 2. Condensed tannins – catechins and gallocatechins Acacia catechu (Fabaceae Family)

  29. Plant sources of catechin tannins - strawberry leaves, persimmon, pomegranate, hazelnuts; • firbark, acacia, chestnut; • coffee, tea, wine , beer, chocolate Action: • antibiotic • herbicide • inflammatory factor •   nutritional supplement - E 181 *Catechin tannins accumulate in large quantities in the meristem cells of the roots of certain species to inhibit the growth of neighboring species - allelopathy !The tannins are easily connected with ions of metals (Fe +) - iron deficiency anemia

  30. Roots and bark of plants - sources of tannin

  31. Freshwater dolphins in tannins saturated waters of the Amazon River

  32. ІІІ. Alkaloids - nitrogen-containing organic compounds of alkaline nature. They are synthesized from amino acids or organic acids. Types:trueproto alkaloidsand pseudo alkaloids 1. True alkaloids: •   Pyridine •   Piperidine • Tropane •   Quinoline •   Isoquinoline •   Quinolizidine •   Indole

  33. True alkaloids - with N in the main chain, formed from amino acids • Pyridine alkaloids nicotine, anabazin- tobacco(Nicotiana tabacum, Solanaceae); trigonelline - fenugreek(Trigonella foenum – graecum, Fabaceae)

  34. Piperidine alkaloids - with saturated heterocyclic ring, i.e., piperidine nucleus. Poison hemlockConium maculatum (Apiaceae)

  35. Sedamin - yellow sedum(Sedum acre, Crassulaceae) Lobeline – Lobelia inflata (Campanulaceae) Piperine - black pepper (Piper nigrum, Piperaceae) Isopeletierin– pomegranate (Punica granatm, Punicaceae) Sedum acre Lobelia inflata

  36. Tropane alkaloids Tropane molecule Atropine group - solanine, atropine, scopolamine, hyoscyamine –Solanaceae family – potato, datura, belladonna, henbane. Action: sedative, anticonvulsant, pesticide Cocaine group - cocaine, ecgonine –Erythroxylaceae family - leaves of the coca bush (Erythroxylon coca) Action: strong CNS stimulant, local anesthetic

  37. Quinoline alkaloids - Quinoline alkaloids such as quinine can be derived from amino acid L-tryptophan: Echinopsin - globe thistles (Genus Echinops , Asteraceae) Dictamin - Gasplant (Dictamnus albus, Rutaceae) Quinine, cinchonine - Cinchona (Cinchona succirubra, Rubiaceae)

  38. Application of quinine Quinine molecule Action: antipyretic, tonic, antimalarials

  39. Isoquinoline alkaloids • Opium group - papaverine, morphine, codeine, thebaine, glaucine, helitropin, chelidonine, protopin, berberine, sanguinarine – Papaveraceae family • Amarilide group - galantamine, nivalin, likorin - Amaryllidaceaefamily Action: treat atonyto digestive canal and uterus, paresis and paralysis, antidote to curare • Curare alkaloids – tubocurarine, alferin, toxiferin Strychnos toxifera Action - a muscle relaxant Strychnos toxifera – Loganiaceae Family

  40. Quinolizidine alkaloids- they are nitrogen-containingheterocyclic compounds. lupine, cytisine, sparteine - genus Laburnum, Cytisus, Sophora (Fabaceae family) –nicotine acetylcholine receptor agonist • Action: medically used to help with smoking cessation

  41. Indole alkaloids - containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole alkaloids. • Loganiaceae Family Strychnine, brucine - Strychnosnux-vomica (Strychnine tree) Action: neuro stimulating, anesthetic, a muscle relaxant

  42. Apocynaceae Family Reserpine - indian snakeroot (Rauwolfia serpentina) • Action: hypertension and neuro - mental disorders treatment,insanity, snakebite, cholera, central nervous system stimulator. • Vincaceae Family Vinca alkaloids: vincamine, vincarpin, vinblastine, vincristine - Genus Vinca (Periwinkle) –anti-mitotic and anti-microtubule  agents - used in chemotherapy for cancer - inhibiting the ability of cancer cells to divide.

  43. Serotonin = phytoserotonin: - in fruits - serotonin regulates intestinal activity, its presence of plants may serve as a way of ensuring seeds are passed through and expelled by the digestive tract quickly - laxatives effect. - In drying seeds- helps to dispose of accumulating ammonia.  Another functions: • Growth regulation • Xylem sap exudation • Flowering • Ion permeability • Plant morphogenesis • Regulation of ripening Sources:walnuts, hickory,pineapples, banana, kiwi fruit, plums and tomatoes, spines of stinging nettles

  44. Proto Alkaloids - with N in the side chain Ephedrine (Ephedra sinica) Action - a stimulant, appetite suppressant, amphetamine replacement + + =

  45. Mescaline – Lophophora williamsii (Cactaceae), Acacia berlandieri (Fabaceae) Action - psychedelic (cause hallucinations, penetrating)

  46. Colchicine alkaloids • Colchicine, colchamin – Liliaceaefamily – supress cell division Colchicum automnale

  47. Pseudo Alkaloids - not formed from amino acids Types: •   terpene •   steroid •   purine alkaloids Delphinium fussum

  48. Terpene alkaloids Aconitine grupe aconitine - larkspur(Ranunculaceae family) – strong neurotoxins used as a local anesthetic Action: can interact with the voltage-dependent sodium-ion channelsin the cell membranes of excitable tissues-cardiac, skeletal muscles and neurons \ Results: paresis & paralysis

  49. Steroid alkaloids - cyclopamine, veratramine - California corn lily(Veratrum californicum- Liliaceae Family) - solanidine, chaconine, tomatidin - Solanaceae Family Action: suppress cell division, metabolic exchange, hormone replacements

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