Phytopharmacolgy Flashcards

(52 cards)

1
Q

Monoterpenes C10H16 Essential Oils

A

Eucalyptus spp., Pinus spp., Valeriana officianalis, Nepeta cataria

Cineol, pinene, iridoid monoterpenes

Sedative, anti-inflammatory

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2
Q

Sesquiterpenes C15H24
EOs or y-lactones

A

Chamomila recrutita, Commiphora molmol
Antifeedant, anesthetic, antibacterial, antifungal
Chamazulene, bisabolol, gossypol

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3
Q

Sesquiterpene Lactones C15H24

A

Asteracea Family
Artemisia spp, Inula helenium,
Digestive bitters, antiprotozoal, antimicrobial, anti-inflammatory
Ex. Artemisinin, parthenolide, alantolactone
Alert: dermatitis

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4
Q

Diterpenes C20H32 resins, bitters

A

Lamiaceae, Berberidaceae Families
Marrubium vulgare, Salvia officinalis
Stomachic, tonic, antiviral, cardiovascular, antimitotic, hepatoprotective
Ex. Marrubin, calumbin, taxol, andrographolide

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5
Q

Triterpenes C30H48 saponins, steroids
Subclasses

A

Subclasses
Free triterpenes
Saponins- steroidal, triterpenoid
Cardiac glycosides
Phytosterols
Curcubitacins
Quassinoids

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6
Q

Free Triterpenes C30H48

A

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

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7
Q

Saponins- lipophilic aglycone one end, hydrophilic sugar other end
Triterpenoid and Steroidal

A

Wound cleanser, detergent, anti-cholesterol, membrane permeability, anti-inflammatory

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8
Q

Triterpenoid Saponins

A

Rosmarinus officinalis, Glycerrhiza glabra, Panax gingseng
Ex. Ginsenosides, glycyrrhetic acid

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9
Q

Steroidal Saponins

A

Precursors of sex hormones, cortisol, vitamin D
Dioscorea villosa, Phytolacca dacandra, Boswellia serrata
Ex. Boswellic acid, saikosaponins, diosgenin

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10
Q

Cardiac Glycosides Triterpenes
Lactone ring C17, sugar -OH group C3

A

Liliaceae, Scrophulariaceae, Apocynaceae Families
Digitalis purpurea
Cardiac contractility, bradycardic, diuretic
Ex. Digoxin, lanatosides, hellebrin, olenadrin, convalloside

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11
Q

Phytosterol Triterpenes
Hydroxyl group C3, extra methyl or ethyl chain

A

Solanaceae, Urticaceae, Burseraceae Families
Withania somnifera, Urtica dioica, Commiphora mulmul
Tumor growth, cholesterol
Ex. Stigmasterol, withanolides, guggulsterones

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12
Q

Tetraterpenes C40H64 Carotenoids

A

Yellow, orange, red fruits and veg
Ex. Lycopene, lutein, vitamins A, carotenes

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13
Q

Pyridine-Piperidine Alkaloids
Nitrogen 6-member ring

A

Piperaceae, Solanaceae, Apiaceae Families
Trigonella foenum-graecum, Lobelia inflata
Ex. Nicotine, trigonelline, piperine, lobeline

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14
Q

Quinoline Alkaloids
Bicycling rings benzene, pyridine

A

Rubiaceae Family
Zanthoxylum americanum
Cardiac
Quinine, arborine,

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15
Q

Isoquinoline alkaloids
Condensation of phenylethylamine with phenylacetylaldehyde

A

Papervaceae, Berberaceae, Ranunculaceae Families
Hydrastis canadensis, Mahonia aquifolium
Many actions- morphanines, protoberberines, protopines, ipecacs, etc

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16
Q

Tropane Alkaloids
Contain pyrrolidine and piperidine rings

A

Solanaceae, Erythroxylaceae Families
Atropa belladonna, coca
Ex. Cocaine, atropine, scopalamine

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17
Q

Quinolizidine Alkaloids
2 carbon rings with shared nitrogen

A

Papillionaceae, Ericaceae, Fabaceae Families
Chelidonodium majus, Vaccinium myrtillus
Cardiovascular, oxytocic
Sparteine, cytisine, myrine

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18
Q

Pyrrolizidine Alkaloids
2 fused 5-member rings with shared nitrogen; diesters at C1, C7

A

Boraginaceae, Asteraceae, Papilionaceae Families
Symphytum officinale,
Toxic to liver
Symphytine, symladine, intermedidine

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19
Q

Indole Alkaloids
Pyrrole ring fused to benzene ring with multiple ring systems

A

Apocynaceae, Loganaceae, Rubiaceae, Convovulaceae, Fungi Families
Vinca spp, Claviceps purpurea, Strychnos nux-vomica, Yohimbine Pausinystalia yohimba

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20
Q

Steroidal Alkaloids
Triterpenoids with nitrogen

A

Solanaceae, liliaceae Families
Potatoes, tomatoes, Veratrum spp
Steroid contraceptive
Ex. Solasodine, solanine, chaconine, proveratrine

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21
Q

Alkaloidal Amines- pseudo alkaloids
Nitrogen is in amino acid side chain on benzene ring

A

Ephedraceae, Liliaceae, Cactaceae, Poaceae Families
Amanitia muscaria, Psilocybe spp., Ephedra sinica
CNS stimulant, hallucinogenic
Ephedrine, cholchicine, muscarine, mescaline, psilocybin

22
Q

Purine Alkaloids
Methylated xanthines

A

Rubiaceae, Theaceae, Sterculaceae, Sapindaceae Families
Camellia sinensis
CNS stimulant, cardiac stimulant, diuretic, bronchial relaxant
Ex. Xanthine, caffeine, theophylline, theobromine

23
Q

Lectins
Polypeptides that interact with polysaccharides on cell membranes

A

Fabaceae, Santalaceae, Urticaceae, Phytolaccaceae Families
Legumes, Urtica dioica, Juglans nigra, Phytolacca decandra
Cytotoxic, mitogenic

24
Q

Glycosides
Glycone sugar attached to aglycone non-sugar

A

Brassicaceae, Rosaceae, scrophulariaceae, Asteraceae, polygonaceae Families
Anthraquinones, flavonoid, phenylpropanoid, cyanogenic, glucosinolates, iridoid and cardiac

25
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
26
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
27
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
28
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
29
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
30
Secoiridoids- iridoid subclass Opening of loganin 5C ring
Gentianaceae, Scrophulariaceae Families Gentiana lutea Amarogentin, gentiopicroside, picroliv
31
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
32
Pectins Galactouronic acid based carbohydrates
Rosaceae, Rutaceae Families Apples, citrus Absorb toxins, lower cholesterol, bulk laxative Ex. Amarogentin, picroliv, gentiopicroside
33
Mucilages Long chain polysaccharides
Boraginaceae, Mulvaceae, Asteraceae, Ulmaceae, Plantaginaceae Families Symphytum officinalis, Althaea officinalis, Ulmus fulva, Plantago ovulata
34
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
35
Fructans Fructosyl-fructose bond Branched or linear
Poaceae, Liliaceae, Asteraceae Families Inula helenium, Arctium lappa, Cynara scolymus, Echinacea spp Diuretic, immunostimulatory, prebiotic Ex. Inulin
36
Phenols C6H6O aromatic benzene ring hydroxyl
Large group with classes Warming, toning, immunostimulating, antiseptic, antihelminthic
37
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
38
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
39
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
40
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
41
Stilbene phenols 2 benzene rings, one phenolic
Polygonaceae, Myrtaceae, Vitaceae Vitis vinifera Antifungal, antioxidant, anti-inflammatory, anti platelet, antiallergenic, anti cancer Ex. Resveratrol
42
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,
43
Tannin polyphenols Stable crosslinkage with proteins
Hydrolysable and condensed classes Precipitate in water Enzyme inhibition in water
44
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
45
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
46
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
47
Subclass Isoflavones
Fabaceae Family Glycerrhiza glabra, Medicago sativa, Trifolium pratense Phytoesteogens Anticancer, menopausal Ex. Genistein
48
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
49
Resins Insoluble in water
Complex, amorphous Protect plant Secreted from pores
50
Fixed oils Fatty acid attached to hydrocarbon, methyl end and carbonyl end
Nutritive Primary metabolite Fatty acids, alkamides
51
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,
52
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