Imidazole Alkaloids

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

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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)??????????

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

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Pilocarpine

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

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Pilocarpine HCl or Pilocarpine HNO3

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

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Steroidal Alkaloids??????

• ?????????????????????,???????????????,?????????,??
  ????????????,???????????,????????????????????????
  ?????(Buxaceae) ????(Liliaceae)??????
• ??????????(Veratrum viride)????(Veratrum album)???

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

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White hellebore???

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

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

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

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Purine Alkaloid ??????

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

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Biogenetic origins of Purine Alkaloids
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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)????????????

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Theophylline

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

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Theobromine

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

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? ? ? ? ???????? ??????? ?????? ????? ?????? ????
Caffeine 1 3
Theophylline 2 1
Theobromine 3 2
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??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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• ??-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?

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Kola ??

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

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Cola nitida
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Guarana ???

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

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Maté or Paraquay Tea????????

• ??-??????(Aquifoliaceae)??,????(Ilex
  paraguariensis St. Hil.)???
• ??-???
• ??-Caffeine??2?Caffeotannic acid?25?
• ??-???????,??????????

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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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?? Ephedra

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

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

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Ephedrine

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

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

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???

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

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

• Ephedrine HCl
• ????????????,?????
• ???????,???????
• ?????????Ephedrine ???

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Peyote ??

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

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

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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?????

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Colchicum ???

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

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Colchicine

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

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

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