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Imidazole Alkaloids

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Title: Imidazole Alkaloids


1
Imidazole Alkaloids
2
  • Imidazole (or glyoxaline) ?????????Pilocarpine???,
    Pilocarpine?????????,????Imidazole?????????????,?
    ????????????(histidine) ,???????????,??Pilocarpine
    ????

3
Pilocarpus ?????
  • ??-Jaborandi?
  • ??-?????????(Rutaceae)?????Pilocarpus jaborandi
    Holme?P. pinnatifolius Lemaire?P. microphyllus
    Stapf?
  • ??-?????
  • ??-
  • 1. Pilocarpus jaborandi???????????? (Pernambuco
    jaborandi),???????
  • 2. P. microphyllus??????????? (Maranham
    jaborandi) ,???????????
  • 3. P. pinnatifolius??????????? (Paraguay
    jaborandi)??????????

4
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5
  • ??-
  • ?????(Pilocarpine)??0.51?Isopilocarpine?Pilocarp
    idine?Pilosine?
  • Pilocarpine??????,?????imidazole????????(Pilocarpi
    c acid)???????
  • ??????????,??????????????????????

6
Pilocarpine
  • Pilocarpic acid???,????????????,????????
  • ????????????????????????,???????????????????,????
    ???,?????,???????,???????????
  • ??-Pilocarpine???????Muscarinic???,???????????
  • ??-????????(glaucoma) ,?????,????????????????????
    ???,???????????,???????????trabecular??,????????

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9
Pilocarpine HCl or Pilocarpine HNO3
  • ?????????,????????Pilocarpine HCl ?0.2510 ?
    Pilocarpine HNO3?0.56 ?????????????????????????

10
Steroidal Alkaloids??????
  • ?????????????????????,???????????????,?????????,??
    ????????????,???????????,????????????????????????
    ?????(Buxaceae) ????(Liliaceae)??????
  • ??????????(Veratrum viride)????(Veratrum album)???

11
Veraturm viride ???
  • ??-American hellebore or Green hellebore?
  • ??-????????,???(Veratrum viride Aiton)??????
    Veratrum????vere?ater ,??truly?black,
    viride?????green ?
  • ??- New England,????North Carolina Tenessee
    northern Geogia????????

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13
  • ??-??????????
  • Steroidal base (Alkamines)??????????Cevadine?Germ
    idine?Germitrine?Neogermitrine?Neoprotoveratrine?V
    eratridine????Germidine?Germitrine????????
  • Alkamines glucosidesPesudojervine?Veratrosine?
  • AlkamineGermine?Jervine?Rubijervine?Veratramine?
  • ??-???????????????????

14
White hellebore???
  • ??-European hellebore?
  • ??-????????,???(Veratrum album L.)??????
  • ??-?????????????,????????
  • ??-????????

15
  • ??-
  • ???????,??????????????Protoveratrine A and B
    (???A?B )?

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17
  • Protoveratrine A ? Protoverine Acetic acid
    Methylbutyric
  • Acid Methylhydroxybutyric acid
  • Protoveratrine B ? Protoverine Acetic acid
    Methylbutyric
  • Acid Methyldihydroxybutyric acid
  • ??-?????????????,???????????????????????

18
Purine Alkaloid ??????
  • Purine??6??????(pyrimidine)?5???imidazole?????????
    ????????,??????????????????
  • ???????????????2,6-dioxypurine (???Xanthine)????(m
    ethylated)????????(Caffeine)???(Theophylline)????
    (Theobromine) ?????????????

19
Biogenetic origins of Purine Alkaloids
20
Caffeine
  • 1,3,7-Trimethylxanthine
  • ?????????????(Guarana)???(Cola)????(Maté)
    ???????,????????????? (Tea sweepings)
    ???????????
  • ????????????,???,??????????
  • Caffeine??citric acid?salicylates?benzoates?bromid
    es?????,??????,???Caffeine??citric acid?sodium
    benzoate?????????????????????(Analeptics)
    ???????(acute circulation failure)????????????

21
Theophylline
  • 1,3-Dimethylxanthine
  • ?theobromine?????,?1885?????,???caffeine????
  • ???,??,?????????,???120???,???????????????????
  • Theophylline??????????????????,????(Bronchial
    asthma)????????????????????????(Emphysema)??????Th
    eophylline????????

22
Theobromine
  • 3,7-Dimethylxanthine
  • ??????????(Theobroma cacao)????
  • ???,?????????,?260????,??????,???????????????????,
    ????????????????
  • ???????????,?????????

23
? ? ? ? ???????? ??????? ?????? ????? ?????? ????
Caffeine 1 3
Theophylline 2 1
Theobromine 3 2
24
??Tea
  • ??-Thea
  • ??-????????,?(Camellia sinensis)????????
  • ??-????????????
  • ??-???????
  • ??- Caffeine (Theine)?14,??? Theophylline?Theobr
    omine?AdenineGallotannic acid?15
    ?0.75???????????????
  • ??-?????????????????

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Coffee ???
  • ??-Coffee seed?Coffee bean?
  • ??-????????,??(Coffea arabica L.?C. liberica
    Hiern)???????
  • ??-?????????????????????????,?????????????????????
    (??)???

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29
  • ??-Caffeine?12?Trigonelline 0.2535Tannin10
    13???,?Trioleoylglycerol?tripalmitoylglycerol??1
    5?glucose?dextrin1013????
  • ??????,??????????,???????Caffeol??,?50?furfurol??
    ??valerianic acid?phenol?pyridine??????????caffein
    e??chlorogenic acid??????,caffeine?????????,?????,
    ???????condenser???caffeine?

30
Kola ??
  • ??-Cola?Kolanut?
  • ??-????????,Cola nitida (Ventent) Schott et
    Endlicher???Cola????????(Cotyledon)?
  • ??-???????????
  • ??-Caffeine???1,kolanut????3.5????(Theobromine)?
    ?1??,??Kolacatechin?

31
Cola nitida
32
Guarana ???
  • ??-Brazilian cacao?
  • ??-???????(Sapinaceae)?????,???(Paullinia cupana
    Kunth)???????
  • Guarana?????????????????
  • ??-???????
  • ??-???(Caffeine)?2.55?Catechutannic acid?25?
  • ??-????????????

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34
Maté or Paraquay Tea????????
  • ??-??????(Aquifoliaceae)??,????(Ilex
    paraguariensis St. Hil.)???
  • ??-???
  • ??-Caffeine??2?Caffeotannic acid?25?
  • ??-???????,??????????

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36
Alkaloidal amines????
  • ????????????,?????????,???????(Aytpical
    alkaloids),??Protoalkaloid?Non-heterocyclic
    alkaloid ?Biological amine,?Ephedrine??Alkaloid
    amine,Colchicine??Alkaloid amide?
  • ???????????(phenylethylamine)???,????????????(Phen
    ylalanine)????(Tyrosine),?Colchicine????
  • ?????Tryptamine?????????????????Tryptophan????(Hor
    deum vulgare)?Gramine??????(Psilocybe
    semperviva)?Psilocybin?????????Serotonin?Bufotenin
    e?

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38
?? Ephedra
  • ??-Ma-Huang
  • ??-????????,???(Ephedra sinica Stapf)?????(E.
    equisetina Bunge)????(E. distachya L.)???????????
  • ??-?????????????????
  • ??-???????,????,?????,?????????,???????????

39
E. sinica
40
E. equisetina
41
E. distachya
42
  • ??-???(Ephedrine?(-)-erythro- a-1-(Methylamino)
    ethyl benzyl alcohol)????,??Mayers
    ??????????????(d-N-Methylephedrine)?????(d-Pseudoe
    phedrine)?????(d-N-Methylpseudoephedrine)?????(l-N
    orephedrine)??????(d-Norpseudoephedrine)?

43
Ephedrine
  • (-)-erythro-a-1-(Methylamino) ethyl benzyl
    alcohol
  • ???????,??L-1-Phenyl-1-acetylcarbinol?????????????
    ????
  • ??????????,?????????????????

44
  • Ephedrine???????????????alpha (a)?beta1
    (b1)?beta2 (b2)??????????beta??????,?????????(Aden
    yl cyclase)???????3,5-????(c-AMP)
    ,?alpha?????????
  • Ephedrine?????????b2???????,???????,?b1???????????
    ??????????(inotropic effect) ?
    a??????????????????????

45
???
  • ????Ephedrine??????????????????,??????????????????
    (Insomnia)???(nervousness) ?

46
  • Ephedrine sulfate
  • ???????????,?????
  • ?????(Hypotension)????????????,????????
  • Ephedrine HCl
  • ????????????,?????
  • ???????,???????
  • ?????????Ephedrine ???

47
Peyote ??
  • ??-Mescal buttons
  • ??-?????????,???(Lophophora williamsii (Lem.)
    Coulter)??????
  • ??-???????????????
  • ??-????Mescaline(3,4,5-Trimethoxy-ß-phenylethylami
    ne)???Anhalanine?Anhalamine?Anhalidine?

48
  • ??-??????,????????,?????????????,???????
  • ????????(Psilocybe mexicana Heim)???Psilocybin?LSD
    ?????????????????????

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51
Khat ??????
  • ??-Abyssinina Tea?
  • ??-??????(Celastraceae)??,??????(Catha edulis
    Forsk)?????
  • ??-??????????
  • ??-?????l-Cathinone,?????????d-Amphetamine,???Cate
    cholamine?????????????Cathinone???????d-Norpseudoe
    phedrine (80)?l-Norephedrine (20)?
  • ??-?????????????????????

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  • WHO?????????????????,???????cathionone???,????????
    ????,??Khat?????

54
Colchicum ???
  • ??-Meadow saffron seed?Autumn crocus?
  • ??-????????,???(Colchicum autumnale
    L.)????????(Corm)??????????,??????????????
  • ??-???????????,??????????
  • ??-???Tropolone??????(Colchicine)?Autumnaline?
    Democoline???????????0.8,??????0.6?

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56
Colchicine
  • ??- Colchicum autumnale???Colchicum??,????????????
    ???????????,???????????????,??????????????
  • ?????????????,??????????,????????????????
  • ???(Gout)??????,colchicine??????(Leukocyte)???,???
    ????????,?????????,??,???????????????
  • Colchicine??????

57
  • Colchicine????????(Antimitotic)
    ,?????,??????????????????(Spindle fibers)
    ,????????colchicine????????,??,??????????????

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