Ethnobotany. Lecture 25
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1 Ethnobotany. Lecture 25 Alexey Shipunov Minot State University March 28th, 2011 Shipunov (MSU) BIOL March 28th, / 42
2 Outline 1 Shipunov (MSU) BIOL March 28th, / 42
3 Polyketides and derived products Short molecules with interleaving ketogroups Many antibiotics (e.g., tetracycline, erythromycin) Shipunov (MSU) BIOL March 28th, / 42
4 Tetracycline Shipunov (MSU) BIOL March 28th, / 42
5 Glycerides Saturated fats Unsaturated fats, especially omega-n-unsaturated Shipunov (MSU) BIOL March 28th, / 42
6 Shikimic acid and derived products Phenylpropenes, like eugenol Lignans like podophyllotoxin Shipunov (MSU) BIOL March 28th, / 42
7 Shikimic acid Shipunov (MSU) BIOL March 28th, / 42
8 Podophyllotoxin Shipunov (MSU) BIOL March 28th, / 42
9 Coumarins Phytoalexins with anti-bacterial properties Some (psoralens from umbel family plants and bergapten from citrus family) are phototoxic Shipunov (MSU) BIOL March 28th, / 42
10 Psoralen Shipunov (MSU) BIOL March 28th, / 42
11 Flavonoids Derivatives of phenylpropane (C 6 C 3 ) Strong antioxidants Examples: naringin from grapefruit, quercetin from oak and other plants, resveratrol from grapes Shipunov (MSU) BIOL March 28th, / 42
12 Quercetin (flavonoid) Shipunov (MSU) BIOL March 28th, / 42
13 Tannins Similar to flavonoids, but much heavier Bind to proteins and provide astringent taste Shipunov (MSU) BIOL March 28th, / 42
14 Terpenes and monoterpenes Terpenes = isoprenoids, derivatives of isoprene (C 5 unit) Monoterpenes are simplest, they are constituents of volatile (essential) oils Examples: menthol from mint, myrcene from Eucalyptus, camphor, iridoids like valepotriates from valerian Shipunov (MSU) BIOL March 28th, / 42
15 Isoprene and mototerpenes Shipunov (MSU) BIOL March 28th, / 42
16 Didrovaltrate (iridoid) Shipunov (MSU) BIOL March 28th, / 42
17 Sesquiterpenes Have C 15 skeleton Example: artemisinin from sage Shipunov (MSU) BIOL March 28th, / 42
18 Artemisinin (sesquiterpene) Shipunov (MSU) BIOL March 28th, / 42
19 Diterpenes Have C 20 skeleton Example: taxol from yew tree (actually, mostly from its endophyte Taxomyces) Shipunov (MSU) BIOL March 28th, / 42
20 Taxol (diterpene) Shipunov (MSU) BIOL March 28th, / 42
21 Triterpenes Have C 30 skeleton and (often) four condensed rings Examples: steroids, glycyrrhetic acid from liquorice and resins Shipunov (MSU) BIOL March 28th, / 42
22 Glycyrrhetic acid (triterpene) Shipunov (MSU) BIOL March 28th, / 42
23 Tetraterpenes Have C 40 skeleton and four condensed rings Carotenes, like β-carotene from carrot and lycopene from tomato Shipunov (MSU) BIOL March 28th, / 42
24 β-carotene (tetraterpene) Shipunov (MSU) BIOL March 28th, / 42
25 Glycosides I Glycosides are any radicals binded to monosaccharides Cyanide glycosides have HCN (cyanide group) Example: amygdalin from almond Glucosinolates contain allyl isothiocyanate group Example: mustard oils of cabbage family plants Shipunov (MSU) BIOL March 28th, / 42
26 Amygdalin (cyanide glycoside) Shipunov (MSU) BIOL March 28th, / 42
27 Glycosides II Cardiac glycosides are steroid-like Example: digotoxin from foxglove (Digitalis) Anthraquinone glycosides contain anthraquinone nucleus (3-ring system) Examples: aloin from Aloë, cascaroside from cascara (Rhamnus purchiana); often laxative Shipunov (MSU) BIOL March 28th, / 42
28 Digitoxin (cardiac glycoside) Shipunov (MSU) BIOL March 28th, / 42
29 Aloin (antraquinone glycoside) Shipunov (MSU) BIOL March 28th, / 42
30 Alkaloids I Alkaloids are most important pharmaceutical components from plants They are based on heterocyclic rings and related to nucleic bases Pyridine-like alkaloids are based on pyridine ring Examples: nicotine, coniin from hemlock Shipunov (MSU) BIOL March 28th, / 42
31 Pyridine alkaloids Shipunov (MSU) BIOL March 28th, / 42
32 Alkaloids II Phenylalkamine alkaloids are amines, not heterocycles Ephedrine which is similar to adrenaline; hallucinogenic mescaline from peyote cactus (Lophophora williamsii); dangerous colchicine from autumn crocus (Colchicum) Quinoline and isoquinoline alkaloids contain more than two rings Famous group: quinine from Cinchona tree; morphines from opium poppy; tubocurarine, main component of curare poison from Chondrodendron; emetine from ipecac (Caephaelis) Shipunov (MSU) BIOL March 28th, / 42
33 Phenylalkamine alkaloids Shipunov (MSU) BIOL March 28th, / 42
34 Quinine (quinoline alkaloid) Shipunov (MSU) BIOL March 28th, / 42
35 Morphine (isoquinoline alkaloid) Shipunov (MSU) BIOL March 28th, / 42
36 Alkaloids III Indole alkaloids contain connecting nitrogen atom Examples: reserpine from snake root (Rauvolfia), LSD which is a chemical analog of ergotamine from ergot fungus which is a rye parasite; brucine which is a powerful poison from nux-vomica (Strychnos). Tropane alkaloids contain tropane chair Examples: hyosciamine from deadly nightshade (Atropa) and cocaine from Erythroxylon Xanthine alkaloids are derivatives of xanthine (with two ketone groups) Examples: caffeine, theophylline, theobromine from coffee, tea and cocoa, respectively Shipunov (MSU) BIOL March 28th, / 42
37 Ergotamine and LSD (indole alkaloids) Shipunov (MSU) BIOL March 28th, / 42
38 Brucine (indole alkaloid) Shipunov (MSU) BIOL March 28th, / 42
39 Tropane alkaloids Shipunov (MSU) BIOL March 28th, / 42
40 Xanthine alkaloids Shipunov (MSU) BIOL March 28th, / 42
41 Summary Polyketides are source chemicals to many antibiotics Derivatives of shikimic acid are phenylpropenes, lignans, coumarins, flavonoids and tannins All terpenes (including carotenes, steroids and resins) are derivatives of isoprene Glycosides is an artificial group Alkaloids are relavives of nucleic bases; they are most important plant chemicals Shipunov (MSU) BIOL March 28th, / 42
42 For Further Reading Appendix For Further Reading A. Shipunov. Ethnobotany [Electronic resource] onwards. Mode of access: M. Heinrich and others. Fundamentals of pharmacognosy amd phytotherapy (selected chapters). [Electronic resource]. Churchhill Livingstone, Mode of access: school/biol_310/heinrich2004_fund_pharm_part.djvu Pages Shipunov (MSU) BIOL March 28th, / 42
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