Phytopharmacolgy Flashcards
Monoterpenes C10H16 Essential Oils
Eucalyptus spp., Pinus spp., Valeriana officianalis, Nepeta cataria
Cineol, pinene, iridoid monoterpenes
Sedative, anti-inflammatory
Sesquiterpenes C15H24
EOs or y-lactones
Chamomila recrutita, Commiphora molmol
Antifeedant, anesthetic, antibacterial, antifungal
Chamazulene, bisabolol, gossypol
Sesquiterpene Lactones C15H24
Asteracea Family
Artemisia spp, Inula helenium,
Digestive bitters, antiprotozoal, antimicrobial, anti-inflammatory
Ex. Artemisinin, parthenolide, alantolactone
Alert: dermatitis
Diterpenes C20H32 resins, bitters
Lamiaceae, Berberidaceae Families
Marrubium vulgare, Salvia officinalis
Stomachic, tonic, antiviral, cardiovascular, antimitotic, hepatoprotective
Ex. Marrubin, calumbin, taxol, andrographolide
Triterpenes C30H48 saponins, steroids
Subclasses
Subclasses
Free triterpenes
Saponins- steroidal, triterpenoid
Cardiac glycosides
Phytosterols
Curcubitacins
Quassinoids
Free Triterpenes C30H48
Polyporaceae, Asteraceae, Ganodermaceae Families
Calendula officinalis, Ganoderma lucidum, Poria
Anti-histamine, hepatoprotective, ACE-inhibitor, anti-inflammatory, cholesterol inhibitor, antiviral
Feradiol monoester, ganoderol, ganoderic acid, Poriatin
Saponins- lipophilic aglycone one end, hydrophilic sugar other end
Triterpenoid and Steroidal
Wound cleanser, detergent, anti-cholesterol, membrane permeability, anti-inflammatory
Triterpenoid Saponins
Rosmarinus officinalis, Glycerrhiza glabra, Panax gingseng
Ex. Ginsenosides, glycyrrhetic acid
Steroidal Saponins
Precursors of sex hormones, cortisol, vitamin D
Dioscorea villosa, Phytolacca dacandra, Boswellia serrata
Ex. Boswellic acid, saikosaponins, diosgenin
Cardiac Glycosides Triterpenes
Lactone ring C17, sugar -OH group C3
Liliaceae, Scrophulariaceae, Apocynaceae Families
Digitalis purpurea
Cardiac contractility, bradycardic, diuretic
Ex. Digoxin, lanatosides, hellebrin, olenadrin, convalloside
Phytosterol Triterpenes
Hydroxyl group C3, extra methyl or ethyl chain
Solanaceae, Urticaceae, Burseraceae Families
Withania somnifera, Urtica dioica, Commiphora mulmul
Tumor growth, cholesterol
Ex. Stigmasterol, withanolides, guggulsterones
Tetraterpenes C40H64 Carotenoids
Yellow, orange, red fruits and veg
Ex. Lycopene, lutein, vitamins A, carotenes
Pyridine-Piperidine Alkaloids
Nitrogen 6-member ring
Piperaceae, Solanaceae, Apiaceae Families
Trigonella foenum-graecum, Lobelia inflata
Ex. Nicotine, trigonelline, piperine, lobeline
Quinoline Alkaloids
Bicycling rings benzene, pyridine
Rubiaceae Family
Zanthoxylum americanum
Cardiac
Quinine, arborine,
Isoquinoline alkaloids
Condensation of phenylethylamine with phenylacetylaldehyde
Papervaceae, Berberaceae, Ranunculaceae Families
Hydrastis canadensis, Mahonia aquifolium
Many actions- morphanines, protoberberines, protopines, ipecacs, etc
Tropane Alkaloids
Contain pyrrolidine and piperidine rings
Solanaceae, Erythroxylaceae Families
Atropa belladonna, coca
Ex. Cocaine, atropine, scopalamine
Quinolizidine Alkaloids
2 carbon rings with shared nitrogen
Papillionaceae, Ericaceae, Fabaceae Families
Chelidonodium majus, Vaccinium myrtillus
Cardiovascular, oxytocic
Sparteine, cytisine, myrine
Pyrrolizidine Alkaloids
2 fused 5-member rings with shared nitrogen; diesters at C1, C7
Boraginaceae, Asteraceae, Papilionaceae Families
Symphytum officinale,
Toxic to liver
Symphytine, symladine, intermedidine
Indole Alkaloids
Pyrrole ring fused to benzene ring with multiple ring systems
Apocynaceae, Loganaceae, Rubiaceae, Convovulaceae, Fungi Families
Vinca spp, Claviceps purpurea, Strychnos nux-vomica, Yohimbine Pausinystalia yohimba
Steroidal Alkaloids
Triterpenoids with nitrogen
Solanaceae, liliaceae Families
Potatoes, tomatoes, Veratrum spp
Steroid contraceptive
Ex. Solasodine, solanine, chaconine, proveratrine
Alkaloidal Amines- pseudo alkaloids
Nitrogen is in amino acid side chain on benzene ring
Ephedraceae, Liliaceae, Cactaceae, Poaceae Families
Amanitia muscaria, Psilocybe spp., Ephedra sinica
CNS stimulant, hallucinogenic
Ephedrine, cholchicine, muscarine, mescaline, psilocybin
Purine Alkaloids
Methylated xanthines
Rubiaceae, Theaceae, Sterculaceae, Sapindaceae Families
Camellia sinensis
CNS stimulant, cardiac stimulant, diuretic, bronchial relaxant
Ex. Xanthine, caffeine, theophylline, theobromine
Lectins
Polypeptides that interact with polysaccharides on cell membranes
Fabaceae, Santalaceae, Urticaceae, Phytolaccaceae Families
Legumes, Urtica dioica, Juglans nigra, Phytolacca decandra
Cytotoxic, mitogenic
Glycosides
Glycone sugar attached to aglycone non-sugar
Brassicaceae, Rosaceae, scrophulariaceae, Asteraceae, polygonaceae Families
Anthraquinones, flavonoid, phenylpropanoid, cyanogenic, glucosinolates, iridoid and cardiac
Cyanogenic glycosides
Nitrogen as hydrocyanic/prussic acid
Poaceae, Rosaceae, Fabaceae, caprifoliaceae Families
Sambucus nigra
Expectorant, antitussive, sedative, digestive, cytotoxic
Ex. Amygdalin, prunasin, sambunigrin
Alert: large excessive doses cause inactivation of respiratory enzymes, dizziness, facial redness, CNS depression, death
Phenylpropanoid glycosides
Glucose, C6C2 moiety, C6C3 moiety
Scrophulariaceae, Plantaginaceae, Asteraceae, Lamiaceae, Verbenaceae Families
Verbascum spp, Plantago spp, Echinacea spp, Rhemannia glutinosa
Immunosuppressive, antitumor, analgesic, neurosedative, antiviral, antibacterial
Ex. Verbasocide, echinoside
Anthraquinones
Quinone ring, hydroxyl groups
Yellow-brown pigment
Rhamnaceae, Polygonaceae, Asphodelaceae, Hypericaceae Families
Rhamnus pershiana, Cassia senna, Aloe vera, Hypericum perforatum,
Peristaltic, antidepressant, antiviral, inhibits bacteria
Ex. Rheum emodin, anthracene, sennosides, anthrone
Alert: contraindications pregnancy or spastic colon, cause dependence
Glycosinolates
Mustard oil glycosides
Sulfate subgroup
Brassicaceae Family
Brassica spp, Allium sativa,
Hot, dry, spicy
Anti cancer, appetite stimulant, respiratory congestion, circulation stimulant, antibiotic
Ex. Sinigrin, alliin, glucobrassicin, sinalbin
Iridoid glycosides
Cyclopentan pyran monoterpenoids
Rubiacieae, Lamiaceae, Scrophulariaceae, Gentianaceae Families
Harpagophytum procumbens, Plantago spp
Most bitter compound
Gastrin, bile, appetite, pancreatic, anti fever, anti inflammatory, antimicrobial, laxative, hepatoprotective
Ex. Harpagoside, procumbin, loganin, asperuloside, aucubin
Secoiridoids- iridoid subclass
Opening of loganin 5C ring
Gentianaceae, Scrophulariaceae Families
Gentiana lutea
Amarogentin, gentiopicroside, picroliv
Gums
Monosaccharides and uronic acid
Water soluble
Mimosaceae, Fabaceae, Rosaceae, Fucaceae Families
Acacia spp, Prunus spp, Astragalus membranaceous, Legumes, Kelp
Cough, cold, diarrhea, feet
Ex. Gum arabica
Pectins
Galactouronic acid based carbohydrates
Rosaceae, Rutaceae Families
Apples, citrus
Absorb toxins, lower cholesterol, bulk laxative
Ex. Amarogentin, picroliv, gentiopicroside
Mucilages
Long chain polysaccharides
Boraginaceae, Mulvaceae, Asteraceae, Ulmaceae, Plantaginaceae Families
Symphytum officinalis, Althaea officinalis, Ulmus fulva, Plantago ovulata
Immuno polysaccharides
Insoluble multibranched, triple helix
Ganodermataceae, Meripilaceae, Araliaceae, Apiaceae, Asteraceae Families
Grifola frondosa, Ganoderma lucidum, Echinacea spp, Panax ginseng, Angelica sinensis
Cytokine stimulating, peyers patch
Ex. B-glucans, bupleuran 2II
Fructans
Fructosyl-fructose bond
Branched or linear
Poaceae, Liliaceae, Asteraceae Families
Inula helenium, Arctium lappa, Cynara scolymus, Echinacea spp
Diuretic, immunostimulatory, prebiotic
Ex. Inulin
Phenols
C6H6O aromatic benzene ring hydroxyl
Large group with classes
Warming, toning, immunostimulating, antiseptic, antihelminthic
Phyenylpropanoid phenols
C6C3
Asteraceae, Zingiberaceae, Rubiaceae, Ericaceae Families
Cynara scolymus, Curcumin longa, Arctostaphylus uva-ursi
Analgesic, anti inflammatory, hepatoprotective, hypocholesterolemic, hypotensive, antiseptic, stimulating
Ex. Caffeic acid, coumaric acid, Ferulic acid, cynarin, curcumin, arbutin, synaptic acid
Salicylate phenols- Carboxylated
Benzene ring with hydroxyl and carboxylic acid
Glycosides, esters, or salts
Salicaceae, Rosaceae, Ericaceae Families
Salix alba, Filipendula ulmaria, Gaultheria spp
Analgesic, anti inflammatory, febrifuge, CNS depressant
Ex. Salicylic acid, salicin, populin, spiraein, gaultherin,
Alert: allergy potential with aspirin/salicylates
Lignan phenols-
Bound at C8
Neolignans- bound other positions
Zygophyllaceae, Schisandraceae, Urticaceae, Berbidaceae, Linaceae Families
Larrea tridentata, Urtica dioica,
Cardiovascular, antioxidant, hypotensive, estrogenic, antimicrobial, antiviral, antineoplastic
Ex. Schisandrins, nordihydroguaiaretic acid
Coumarin phenols
Lactones of hydro cinnamic acids
Often glycosides
Furanocoumarins have a furan ring
Apiaceae, Rutaceae, Poaceae, Fabaceae, Ranunculaceae Families
Lavandula officinalis, Acacia cinnamom, Angelica sinensis
Ex. Spasmolytic, photosensitization, hypotensive, anti asthmatic, antimicrobial, antifungal
Ex. Aesculin, Angelican, khellin, psoralen, bergapten
Stilbene phenols
2 benzene rings, one phenolic
Polygonaceae, Myrtaceae, Vitaceae
Vitis vinifera
Antifungal, antioxidant, anti-inflammatory, anti platelet, antiallergenic, anti cancer
Ex. Resveratrol
Quinone phenols
Polycyclic with opposite carbonyl groups
Tannins, flavonoids, anthocyanins
Lythaceae, Juglandaceae, Bignoniaceae, Droseraceae Families
Juglans nigra,
Electron-transport chain, antioxidant, antimicrobial, antifungal, antitumor
Ex. Ubiquinol, menaquinone, benzoquinone, juglone, lawsone,
Tannin polyphenols
Stable crosslinkage with proteins
Hydrolysable and condensed classes
Precipitate in water
Enzyme inhibition in water
Hydrolysable tannins
Phenols and linked sugar
Soluble in water and alcohol
Rosaceae, Fagaceae, Geraniaceae Families
Quercus spp, Filipendula ulmaria, Rubis ideaus,
Mucus membranes, anti inflammatory, antiedema esp infection, reduce bleeding, anti diarrhea,
Ex. Gallic acid, egallic acid, sanguiin, agrimonin, geraniin
Condensed tannin polyphenols
Polymer of catechins and leucoanthocyanins
Partially soluble in water or alcohol, soluble in glycerine
Red residues are insoluble
Oligomeric procyanidins
Theacea, Vitaceae, Pinaceae Families
Camellia sinensis, Vitis vinifera, Pinus spp
Vascular, antioxidant, connective tissue, delay lipid peroxidation
Ex. Epicatechin, pycnogenol
Flavoid polyphenols
2 benzenes, 3C chain
White and yellow pigment
Hydrolysis in intestines, aglycones formed
Brassicaceae, Ericaceae, Asteraceae Families
Silybum marianum, Scutellaria baicalensis, capsicum minimum, citrus, greens, tomatoes, cruciferous, dark cherries, berries
Antioxidant, hypotensive, stabilize membranes
Ex. Rutin, quercetin, kaempferol, myricitin, silymarin, apigenin, baicalein
Subclass Isoflavones
Fabaceae Family
Glycerrhiza glabra, Medicago sativa, Trifolium pratense
Phytoesteogens
Anticancer, menopausal
Ex. Genistein
Anthocyanin polyphenols
Glycosides of flavylium salts
More sugar chains cause deeper pigment
Red, black, blue, purple pigment fruit and flower
Vitaceae, Ericaceae Families
Vitis vinifera, Vaccinium macrocarpon
Micro circulation, diabetic neuropathy and opthomology, stabilize collagen
Ex. Cyanidin, mangostin, betanin, pelarginin
Resins
Insoluble in water
Complex, amorphous
Protect plant
Secreted from pores
Fixed oils
Fatty acid attached to hydrocarbon, methyl end and carbonyl end
Nutritive
Primary metabolite
Fatty acids, alkamides
Fatty acids
Saturated- no double bonds
Monounsaturated 1 double bond
Polyunsaturated 2or more
Arecaceae, Onagraceae, Boraginaceae, Cannabinaceae Families
Serenoa repens,
Cholesterol, inflammation, essential nutrient
Ex. Linoleic acid, palmitic acid, steric acid, oleic acid,
Alkamides fixed oils
Amines and FA form chains
Resistance to hydrolysis
Asteraceae, Piperaceae, Rutaceae, Solanaceae Families
Zanthoxylum americanum, Echinacea spp, Capsicum minimum, Achillea millefolium
Analgesic, anti inflammatory, sialogogue, vermifuge, digestive, circulatory, spasmolytic, carminitive, immunostimulant
Burning, tingling, numbing
Ex. Capsaicin
