Phytopharmacolgy Flashcards

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
Q

Cyanogenic glycosides
Nitrogen as hydrocyanic/prussic acid

A

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
Q

Phenylpropanoid glycosides
Glucose, C6C2 moiety, C6C3 moiety

A

Scrophulariaceae, Plantaginaceae, Asteraceae, Lamiaceae, Verbenaceae Families
Verbascum spp, Plantago spp, Echinacea spp, Rhemannia glutinosa
Immunosuppressive, antitumor, analgesic, neurosedative, antiviral, antibacterial
Ex. Verbasocide, echinoside

27
Q

Anthraquinones
Quinone ring, hydroxyl groups

A

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
Q

Glycosinolates
Mustard oil glycosides
Sulfate subgroup

A

Brassicaceae Family
Brassica spp, Allium sativa,
Hot, dry, spicy
Anti cancer, appetite stimulant, respiratory congestion, circulation stimulant, antibiotic
Ex. Sinigrin, alliin, glucobrassicin, sinalbin

29
Q

Iridoid glycosides
Cyclopentan pyran monoterpenoids

A

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
Q

Secoiridoids- iridoid subclass
Opening of loganin 5C ring

A

Gentianaceae, Scrophulariaceae Families
Gentiana lutea
Amarogentin, gentiopicroside, picroliv

31
Q

Gums
Monosaccharides and uronic acid

A

Water soluble
Mimosaceae, Fabaceae, Rosaceae, Fucaceae Families
Acacia spp, Prunus spp, Astragalus membranaceous, Legumes, Kelp
Cough, cold, diarrhea, feet
Ex. Gum arabica

32
Q

Pectins
Galactouronic acid based carbohydrates

A

Rosaceae, Rutaceae Families
Apples, citrus
Absorb toxins, lower cholesterol, bulk laxative
Ex. Amarogentin, picroliv, gentiopicroside

33
Q

Mucilages
Long chain polysaccharides

A

Boraginaceae, Mulvaceae, Asteraceae, Ulmaceae, Plantaginaceae Families
Symphytum officinalis, Althaea officinalis, Ulmus fulva, Plantago ovulata

34
Q

Immuno polysaccharides
Insoluble multibranched, triple helix

A

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
Q

Fructans
Fructosyl-fructose bond
Branched or linear

A

Poaceae, Liliaceae, Asteraceae Families
Inula helenium, Arctium lappa, Cynara scolymus, Echinacea spp
Diuretic, immunostimulatory, prebiotic
Ex. Inulin

36
Q

Phenols
C6H6O aromatic benzene ring hydroxyl

A

Large group with classes
Warming, toning, immunostimulating, antiseptic, antihelminthic

37
Q

Phyenylpropanoid phenols
C6C3

A

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
Q

Salicylate phenols- Carboxylated
Benzene ring with hydroxyl and carboxylic acid
Glycosides, esters, or salts

A

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
Q

Lignan phenols-
Bound at C8
Neolignans- bound other positions

A

Zygophyllaceae, Schisandraceae, Urticaceae, Berbidaceae, Linaceae Families
Larrea tridentata, Urtica dioica,
Cardiovascular, antioxidant, hypotensive, estrogenic, antimicrobial, antiviral, antineoplastic
Ex. Schisandrins, nordihydroguaiaretic acid

40
Q

Coumarin phenols
Lactones of hydro cinnamic acids
Often glycosides
Furanocoumarins have a furan ring

A

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
Q

Stilbene phenols
2 benzene rings, one phenolic

A

Polygonaceae, Myrtaceae, Vitaceae
Vitis vinifera
Antifungal, antioxidant, anti-inflammatory, anti platelet, antiallergenic, anti cancer
Ex. Resveratrol

42
Q

Quinone phenols
Polycyclic with opposite carbonyl groups
Tannins, flavonoids, anthocyanins

A

Lythaceae, Juglandaceae, Bignoniaceae, Droseraceae Families
Juglans nigra,
Electron-transport chain, antioxidant, antimicrobial, antifungal, antitumor
Ex. Ubiquinol, menaquinone, benzoquinone, juglone, lawsone,

43
Q

Tannin polyphenols
Stable crosslinkage with proteins

A

Hydrolysable and condensed classes
Precipitate in water
Enzyme inhibition in water

44
Q

Hydrolysable tannins
Phenols and linked sugar

A

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
Q

Condensed tannin polyphenols
Polymer of catechins and leucoanthocyanins

A

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
Q

Flavoid polyphenols
2 benzenes, 3C chain

A

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
Q

Subclass Isoflavones

A

Fabaceae Family
Glycerrhiza glabra, Medicago sativa, Trifolium pratense
Phytoesteogens
Anticancer, menopausal
Ex. Genistein

48
Q

Anthocyanin polyphenols
Glycosides of flavylium salts
More sugar chains cause deeper pigment

A

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
Q

Resins
Insoluble in water

A

Complex, amorphous
Protect plant
Secreted from pores

50
Q

Fixed oils
Fatty acid attached to hydrocarbon, methyl end and carbonyl end

A

Nutritive
Primary metabolite
Fatty acids, alkamides

51
Q

Fatty acids
Saturated- no double bonds
Monounsaturated 1 double bond
Polyunsaturated 2or more

A

Arecaceae, Onagraceae, Boraginaceae, Cannabinaceae Families
Serenoa repens,
Cholesterol, inflammation, essential nutrient
Ex. Linoleic acid, palmitic acid, steric acid, oleic acid,

52
Q

Alkamides fixed oils
Amines and FA form chains

A

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