Alkaloids, Medicinal Plant Chemistry and Botanical Medicine Uses

1. The Alkaloids
Alkaloids are organic compounds with at least one
nitrogen atom, usually in a heterocyclic ring
Difficult to define
Do not represent a homogeneous group on the
chemical, biochemical or physiological viewpoint
Most either sedate or stimulate

2. The Alkaloids
Alkaloids end in the suffix -INE
– Caffeine, Ephedrine, Morphine, Berberine, Reserpine,
Nicotine, Lobeline etc.
– They are all structurally diverse
– Bitter taste
– Over 10,000 have been ID’ed and many new alkaloids are
described daily

3. Alkaloids: Chemistry
Extremely varied
Common Features:
– 1. They are sparingly soluble in water
– 2. Most are solid at room temperature, except,
nicotine, coniine (Conium maculatum) and sparteine
(Scotch Broome)
– 3. Most are basic do to their amino nitrogen

4. Function of alkaloids in Plants
• Poisonous agents that protect the plants against
insects, fungus, predators
• End products of nitrogen detoxification
• Regulate growth factors
• Reserve substances which can supply nitrogen
when needed

5. DISTRIBUTION OF
ALKALOIDS
• Found in animal kingdom in Fire ants
& Toad venom
• Most occur in annual flowering plants
• Often poisonous but can also be
powerful medicine

6. Medicinal Alkaloids
Morphine- analgesic -Opium poppy
Ephedrine- stimulant- Ephedra, Ma Huang
Reserpine- relaxant- Rauwolfia serpentina ( Indian
snakeroot)
Theophylline- bronchial relaxant- Camellia sinensis
(tea)
Quinine- anti-malarial agent-Chinchona
Berberine- antimicrobial- Golden Seal, Barberry

7. Monocyclic Alkaloids
Contain only one ring.
Nicotine

8. Bicyclic Alkaloids
Tropane- 1,4 nitrogen bridge

9. Polycyclic Alkaloids
include strychnine, lysergic acid, cannabinol, morphine, heroin and codeine.

10. Actions of Alkaloids
• Antidepressants
• Respiratory
stimulation
• Cardiac stimulants
• Muscle relaxants
• Addictive
•
•
•
•
•
•
•
Nervous stimulation
Nervous suppression
Analgesia
Antimicrobial
Entheogenic
Mydriatics (atropine)
Miotics (Physostigmine,
Pilocarpine)

11. Pyrrolidine (5) and Piperidine (6)
• The nitrogen is either
in a 5 or 6 member
ring
• Very poisonous in
nature

12. Poison Hemlock
Conium maculatum
Poison used to kill
Socrates

13. Coniine from water hemlock
• Used in Homeopathic
medicine for extreme
vertigo, dizziness
• Weakness, nausea &
motion sickness
• Piperidine 6 sided ring

14. Lobelia (Lobelia inflata)
•
antismoking preparations
•
Competitive antagonist- nicotine
•
Relaxant and bronchodilator
•
Contains 14 alkaloids- lobeline
•
Asthma, bronchitis
•
Adverse effects: nausea, dizzinesssimilar to caffeine
•
Do not use during
pregnancy/nursing

15. Lobeline

16. Nicotine
Source:http://www.intox.org/databank/documents/supplem/supp/sup2_60.gif
•
•
•
•
50 mg is FATAL
Used as an insecticide
Extremely toxic alkaloid
Cholinergic receptor agonist
http://www.answers.com/topic/nicotin
• Enhances acetylcholine
• Muscles ‘twitch’ and spasm
• Then respiratory paralysis

17. •

18. Lobelia
Smoking Cessation
Neuro Associative Conditioning:
- smoke cigarette,
followed by 10 drops
of lobelia
extract/tincture
– Repeat until nauseous
– Smoking = Nausea
instead of Smoking =
Pleasure
Cold Turkey Support:
Go cold turkey - take 10
drops lobelia to arrest the
urge
Substitution:
Smoke lobelia, works well
with mullein

19. Tropane alkaloids
:
PHOTO
http://www.meb.uni-bonn.de/giftzentrale/pflanzen/engelstrompete.jpg
Condensed pyrrolidinepipidine alkaloids
Found in the Solanaceajimsonweed, henbane,
belladonna, mandrake
-Brugmansia (Angels
Trumpet)tree datura,
LEFT)
Hallucinogenic

20. Datura stramonium
www.esc.nsw.gov.au

21. Jimson Weed
Intentional misuse- eat seeds,
drink tea and/or smoke
cigarettes made from dried
flowers
Found in classic herbal asthma
preparation:
Asthmador
Barter's Powder
Kinsman's Asthmatic Powder
Green Mountain Asthmatic
Compound
Haywood's Powder

22. Cocaine: Tropane alkaloid
• Erythroxylacea :
another plant family
rich in tropanes
• Coca Leaves- source
of the alkaloid
COCAINE

23. PURINE ALKALOIDS
http://www.benbest.com/health/xanthines.gif

24. PURINE EFFECTS
•
•
•
•
• Enhances NSAID
Diuretic
analgesia
CNS stimulant
• Cardiac & Resp.
Anorexia
stimulant
Relaxes bronchospasm
Effects can be surprising: The effects of caffeine on the
inducibility of atrial fibrillation. Conclusion: the presence of
caffeine may result in an unexpected reduction of AF
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Ret

25. ISOQUINOLINE alkaloids
•
•
Largest group of
alkaloids
•
•
Derived from the amino •
acids Tyrosine and
•
Phenylalanine
•
•
•
Anti-microbial
Chologogue/choleretic
Enzyme inhibitor
Antitumor
Pain suppressant
Cough suppressant
Hypnotic
Relaxant
Antispasmodic

26. BERBERINE
Found in 23 genera
Important sources:
Mahonia spp., Berberis,Spp., Coptis
spp., Hydrastis canadensis,
Phellodendron, Sanguinaria (blood
root)
Yellow in color
Soluble in ETOH
Highest concentration in Root bark
Amoebicidal,antibacterial & fungal,
antitumor,bitter,hepatic
Swap on tonsils for strep throat
Mucus membrane problems

27. Oregon grape
Mahonia aquafolium
http://www.chlorischile.cl/cursoonline/guia3/mahonia.jpg

28. Golden Seal
Hydrastis canadensis
• Endangered species
• Root most medicinal
• Watch for leaf
capsules at lower
prices

29. Corydalis yanhuosu

30. Canadine
• Found in Corydalis
yan huo su (the most
powerful pain killer in
Chinese medicine) and
Hydrastis canadensis
• Has hypotensive
properties

31. Tetrahydropalmatine (THP)
• Found in Corydalis
yanhusuo
• 40% as strong as
morphine;vinegar extract
strongest
• THP is nonaddictive
• Potentiates acupuncture
analgesia
• Used in all types of pain
in China; one of Nature’s
most potent pain relievers

32. Morphine
• Powerful
analgesic,narcotic,
• sedative and antispasmodic
• Derived from the dried
latex of Papaver
somniferum

33. Sanguinarine
Derived from Bloodroot
(Sanguinaria canadensis)
Celandine (Chelidonium
majus)
• Antibacterial, antiviral:
papilloma virus,genital
worts, cervical dysplasia
• Mouthwash to stimulate
epithelial growth and
repair of gingival tissue

34. Indole Alkaloids
Reserpine
Rauwolfia (Indian
Snakeroot)
• Lowers BP, decreases
catecholamines
• Peripheral vasodilation
• Depression 15% of patients

35. Passion Flower
Passiflora incarnata
Harmine
• Powerful relaxant with
serotonin-like action
• Entheogen in high
amounts
• Passiflora incarnata
6:1 solid extract for
stress

36. Yohimbine
Pausinystalia yohimbe
• Two sterioisomers: Alpha and Beta
• Act as
– Serotonin antagonist
– Increases heart rate
– Increases Erection
Adverse effects include: anxiety, insomnia,
tachycardia, heart palpitations

37. Quinoline alkaloids
Quinine, Quinidine, cinchonidine
Common names: Quinine bark,, quinine,
China bark, cinchona yellow cinchona, red
cinchona, Peruvian bark, Jesuit's bark,
quina-quina, calisaya bark, fever tree
www.Rain-tree.com

39. Quinine bark
Source: rain-tree.com
• Cinchona, or quinine bark, is one of the
rainforest's most famous plants
• Treatment for malaria
• In Brazilian herbal medicine quinine bark is
considered a tonic, a digestive stimulant, and
fever-reducer. It is used for anemia,
indigestion, gastrointestinal disorders, general
fatigue, fevers, malaria and as an appetite
stimulant.

40. Gelsemium sempervirens

41. Gelsemine
• Used in homeopathy
for
–
–
–
–
–
–
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Dull
Droopy
Drowsiness
Flu weakness myalgia
Neuralgia
Migraines
Visual disturbances

42. Scotch Broome