This document provides information about alkaloids, including: - Alkaloids are organic compounds containing at least one nitrogen atom, usually in a heterocyclic ring. They are found in plants and some animals. - Important classes of alkaloids discussed include isoquinolones (including berberine), purines (including caffeine and theobromine), tropanes (including those in plants like Datura and Brugmansia), and pyrrolidines/piperidines (including nicotine, lobeline, and coniine). - Alkaloids have diverse physiological effects including stimulation, sedation, antimicrobial properties, and more. Several medically important alk

1. 1
NTR5302
Alkaloids
Pharmacognocy
Ellen Kamhi PhD, RN, AHG, AHN-www.
naturBaClnurse.com

2. Content on some slides in
this presentation :
Used With Permission
from Lisa Ganora
This is indicated by LG on the
bottom left corner of the
slide.
2
LISA GANORA
www.herbalconstituents.com
© 2010 Lisa Ganora
LG

3. 3
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
View Link:
http://shekharalk.blogspot.com/2008_08_01_archive.html

4. Alkaloids end in the suffix –INE
Examples: Caffeine, Ephedrine, Morphine,
Berberine, Reserpine, Nicotine, Lobeline
etc.
They are all structurally diverse
Bitter taste
Over 10,000 have been identified and
many new alkaloids are described daily
4
Alkaloids

5. The name “Alkaloid” refers to the
alkaline nature of most of these
chemicals, due to the presence of an
amino group.
Most alkaloids are derived from four
different amino acids:
Lysine (eg. Sedamine)
Phenylalanine (eg. Ephedrine)
Tyrosine ( eg. Mescaline)
Tryptophan ( eg. Quinine, Lysergic
Acid)
5
Alkaloids

6. Vary Greatly but have some Common Features:
Most are derived from Amino Acids
Visit link:
http://www.usm.maine.edu/~newton/Chy251_253/Lectures/AminesII/alkaloids.html
They are sparingly soluble in water
and alcohol
They contain Nitrogen
Most are alkaline (basic) due to their
amino nitrogen
6
Alkaloids

7. Alkaloids
FUNCTIONS IN PLANTS:
Poisonous agents that protect the
plants against insects, fungus,
predators
7
End products of nitrogen
detoxification
Regulate growth factors
Reserve substances which can supply
nitrogen when needed

8. 8
Alkaloids
Distribution:
Found in animal kingdom in
Fire Ants & Toad Venom
Most occur in annual flowering plants
Often poisonous but can also be
powerful medicine
Link: http://www.herbs2000.com/h_menu/alkaloids.htm

9. Alkaloids
http://en.wikipedia.org/wiki/Colorado_River_Toad
http://www.eitangrunwald.com/AZ803/AZ803%20Large/809Bufo_alvarius_DM.jpg
9
Bufo Alvarius
THE
PSYCHEDELIC
TOAD
Sonoran Desert

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

11. Alkaloids
MEDICINAL ALKALOIDS: Examples
 Morphine - analgesic - Opium poppy
 Ephedrine - stimulant- Ephedra, Ma
Huang
 Reserpine - relaxant- Rauwolfia serpentina
11
(Indian snakeroot)
 Theophylline - bronchial relaxant –
Camellia sinensis (tea)
 Quinine - anti-malarial agent - Chinchona
 Berberine – antimicrobial - Golden Seal,
Barberry

12. SAMPLE CATEGORIES:
12
Monocyclic
Bicyclic
Polycyclic
Pyrrolidine
Piperidine
Tropane
Purine
Isoquinoline
Indole
Quinoline
Alkaloids

13. 13
Alkaloids
Ring Systems:
LG

14. 14
Monocycli
Contains
only one
c
ring
Nicotine
Alkaloids

15. 15
BICYLIC
Two Rings
Alkaloids

16. POLYCYCLIC Many Rings
includes strychnine, lysergic acid,
cannabinol, morphine, heroin and
16
codeine.
Alkaloids

17. 17
Alkaloids
Pyrrolidine
Piperidine
Pyrrolizidine
Tobacco
http://www.marvistavet.com/assets/images/tobacco_pzlant.gif

18. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
18
The nitrogen is either in
a 5 or 6 member ring
Very poisonous in
nature
http://www.henriettesherbal.com/PAs/PAs-toxicity.html

19. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
Poison Hemlock
(Conium
maculatum)
19
Poison used to kill
Socrates

20. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
Used in
Homeopathic
medicine for
extreme vertigo,
dizziness
Weakness, nausea
& motion sickness
Piperidine 6 sided
ring
20
Coniine From
Water Hemlock

21. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
21
 Antismoking preparations
 Competitive antagonist-nicotine
 Relaxant and
bronchodilator
 Contains 14 alkaloids-lobeline
 Asthma, bronchitis
 Adverse effects: nausea,
dizziness- similar to
caffeine
 Do not use during
pregnancy/nursing
Lobelia (Lobelia
inflata)
LOBELIA
LG

22. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
22
LOBELIA
Bronchodilator
Antispasmodic
Respiratory stimulant
Reduces nicotine cravings:
stimulates nicotinic
receptor sites
Excess is emetic, toxic
Lobeline

23. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
23
Lobeline

24. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
Extremely toxic alkaloid
50 mg is FATAL (.7-.1
mg/cig)
Used as an insecticide
Cholinergic receptor
agonist
http://www.answers.com/topic/nicotinic-Enhances acetylcholine
Muscles ‘twitch’ and
spasm
Then respiratory
24
paralysis
Nicotine

25. 25
Alkaloids

26. Alkaloids:PYRROLIDINE(5)
PIPERIDINE(6)
Lobelia: Smoking Cessation Methods
26
1. NEURO ASSOCIATIVE
CONDITIONING:
 smoke cigarette,
followed by 10 drops
of lobelia
extract/tincture
Repeat until nauseous
Smoking = Nausea
instead of Smoking =
Pleasure
2. COLD TURKEY
SUPPORT:
Go cold turkey - take
10 drops lobelia to
arrest the urge
3. SUBSTITUTION:
Smoke lobelia, works
well with mullein

27. Alkaloids : PYRROLIZIDINE
http://en.wikipedia.org/wiki/Tussilago_farfara COL2T7SFOOT
LG

28. Alkaloids : PYRROLIZIDINE
28
LG

29. Alkaloids : PYRROLIZIDINE
 The actual toxicity arises in the liver from metabolites of
1,2-unsaturated PAs known as pyrrole or pyrrolic
derivatives
 These are capable of forming DNA
adducts & can act as alkylating agents
which damage proteins lining the interior
of blood vessels
 Veno-occlusive liver disease
High doses damage vessels
in heart & lungs
29
http://www.mdpi.org/ijms/papers/i3090948.pdf
LG

30. Alkaloids : PYRROLIZIDINE
VOD ( Veno-oclusive Disease) 30
LG

31. 31
Alkaloids

Tropane

32. Alkaloids: TROPANE
Condensed pyrrolidine-pipidine
alkaloids
Found in the Solanacea-jimsonweed,
32
henbane,
belladonna, mandrake
Hallucinogenic
Brugmansia (Angels Trumpet) tree datura
http://www.meb.uni-bonn.de/giftzentrale/pflanzen/engelstrompete.jpg

33. 33
Alkaloids: TROPANE
Datura stramonium
Link To: www.naturalstandard.com Jimson Weed

34.  Jimsonweed, Locoweed, Sacred
Datura
 Ayurveda prescribed Datura for
asthma thousands of years ago
 Known in Europe as ‘Potter’s
asthma cure’
34
Alkaloids: TROPANE
 Old remedy for
hemorrhoids
(salve)
 Antispasmodic
 Narcotic anodyne
LG  Psychotropic

35. Alkaloids: TROPANE
Datura (Jimson Weed)
Intentional misuse- eat seeds, drink
tea and/or smoke cigarettes made
from dried flowers
35
Found in classic herbal
asthma preparations:
 Asthmador
 Barter's Powder
 Kinsman's Asthmatic Powder
 Green Mountain Asthmatic
Compound
 Haywood's Powder

36. Alkaloids: TROPANE
Erythroxylacea :
another plant
family rich in
tropanes
Coca Leaves :
source of the
alkaloid COCAINE
36
Cocaine

37. 37
Alkaloids
PURINE
Kola Nut
Xanthine
Coffee
Caffeine

38. 38
Alkaloids: PURINE
Technically not alkaloids
(not made directly from
amino acids)
Caffeine
Theobromine
Theophylline
LG

39. Alkaloids: PURINE
http://www.benbest.com/health/xanthines.gif 39

40. Alkaloids: PURINE
 CAFFEINE
coffee, tea, yerba mate
40
 THEOBROMINE
cocao
 THEOPHYLLINE
camellia (Tea), guarana

41. Alkaloids: PURINE
Caffeine is the chief
methylxanthine
constituent
CNS stimulant
Increases heart rate,
respiration
Diuretic
41
COFFEE
OVERDOSE: tachycardia,
insomnia, tremors, epigastric
pain, headache, nausea
LG

42. Alkaloids: PURINE
Theobromine is the
major constituent
Small amounts of caffeine
Trace amounts of
theophylline
Small amounts of
anandamide
(endogenous cannabinoid)
Tryptophan
Phenylethylamine (PEA) =
endogenous amphetamine
Tyramine (migraine 42
trigger)
Mood elevation; depression
CACAO
LG

43. 43
Alkaloids: PURINE
TEA (Camellia sinensis)
Caffeine is the major
methylxanthine
Theophylline is present in
small amounts
Theophylline used as a drug
for asthma & bronchospasm
‘Side effects’ similar to
caffeine
Stimulant, diuretic
LG

44. Alkaloids: PURINE
Guaraná, Kola, Yerba Maté
44
Guaraná & Kola:
caffeine
Yerba Maté:
caffeine, theobromine
All contain
polyphenolic
antioxidants in
addition
to methylxanthines
Photo © Martin Wall 2003
LG

45. Alkaloids: PURINE
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
45
Diuretic
CNS stimulant
Anorexia
Relax
bronchospasm
Enhances NSAID
analgesia
Cardiac & Resp.
stimulant
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&
dopt=AbstractPlus&list_uids=16919674&query_hl=9&itool=pubmed_docsum

46. http://www.1adventure.com/archives/images/red-poppy-flowers-picture-lowres.Alkaloids
46
ISOQUINOLON
E

47. Alkaloids: ISOQUINOLONE
47
LG

48. Alkaloids: ISOQUINOLONE
Derived from the amino acids
Tyrosine and Phenylalanine
Largest group of alkaloids: includes
Berberine
Canadine
Tetrahydropalmatine
(THP)
Morphine
Sanquinine
48

49. Alkaloids: ISOQUINOLONE
49
Medicinal
Actions:
Anti-microbial
Chologogue/choleret
ic
Enzyme inhibitor
Antitumor
Pain suppressant
Cough suppressant
Hypnotic
Relaxant
Antispasmodic

50. Alkaloids: ISOQUINOLONE
 Yellow in color
 Soluble in ETOH
 Highest concentration in
Root bark
 Amoebicidal
 Antibacterial (Swap on
tonsils for strep throat)
 fungal
 antitumor
 bitter
 hepatic
 Mucus membrane
support
50
BERBERINE

51. Alkaloids: ISOQUINOLONE
Found in 23 genera
Important sources:
Phellodendron
(Phellodendron
amurense)
Bloodroot
(Sanguinaria canadensis)
Chinese Goldenseal
(Coptis chinenesis )
51
BERBERINE
Golden Seal
(Hydrastis
canadensis)
Oregon Grape Root
(Mahonia
Aquafolium)
Barberry
(Berberis spec)

52. Alkaloids: ISOQUINOLONE
Nitrogen
(blue)
BERBERINE
Oxygen
(red) Hydrogen
52
(cyan)
Carbon
(magenta)
antimicrobial molecule in Oregon Grape
LG

53. Alkaloids: ISOQUINOLONE
Goldenseal & Oregon Grape
 Contain berberine & related alkaloids:
antibacterial, antifungal; antibiotic
alternative
 Tonic for mucous membranes
 Useful for upper respiratory conditions &
UTI’s
53
BERBERINE
LG

54. Alkaloids: ISOQUINOLONE
54
LG

55. Alkaloids: ISOQUINOLONE
BERBERINE
MDR Pump: Multi Drug Resistant
http://www.ncbi.nlm.nih.gov/pubmed/12842327
55
Pump
Biological mechanism used by a
cell to rid itself of chemicals
PGP: P-glycoprotein efflux pump
Study on mechanism of action of
5’-MHC-D & pheophorbide-A

56. Alkaloids: ISOQUINOLONE
BERBERINE
Antibacterial: Staphylococcus aureus
MDR pump (PGP) ejects the berberine
5’-MHC-D & pheophorbide-A inhibit
PGP
Berberine stays inside bacteria, kills it
56
Exophysiological
Synergy

57. Alkaloids: ISOQUINOLONE
57
Early Study on Synergy
LG

58. Alkaloids: ISOQUINOLONE
58
GOLDENSEAL
(Hydrastis
canadensis)
Endangered species
Root most medicinal
Watch for leaf capsules
at lower prices

59. Alkaloids: ISOQUINOLONE
GOLDENSEAL
Hydrastine, a strong antibacterial &
fungicide
59
Berberine
Berberastine
Hydrastine
LG

60. Alkaloids: ISOQUINOLONE
Goldenseal Medicinal Use:
http://www.vitaminshoppe.com/content/en/healthguide/hncontent.jsp
?org=VSI&ContentID=2099007&category=Herb&title=Goldenseal&type=
60
Link:
GOLDENSEAL

61. Alkaloids: ISOQUINOLONE
OREGON GRAPE
(Mahonia
aquafolium)
http://www.chlorischile.cl/cursoonline/guia3/mahoni6a.1jpg

62. Alkaloids: ISOQUINOLONE
62
OREGON GRAPE
Berberine & relatives
predominate
Some hydrastine
Actions very similar
to Goldenseal
Berberine
LG

63. Alkaloids: ISOQUINOLONE
OREGON GRAPE
Oregon Grape Medicinal Use:
63
http://www.vitaminshoppe.com/content/
en/healthguide/hncontent.jsp?org=VSI&intsource=hc&ContentID=
2141009&category=Herb&title=Oregon%20Grape&type=

64. Alkaloids: ISOQUINOLONE
64
LG

65. Alkaloids: ISOQUINOLONE
65
CORYDALIS Species
yán hú suo

66. Alkaloids: ISOQUINOLONE
66
Canadine
CORYDALIS Yan Hu Suo
Canadine is found in
Corydalis yan huo su
The most powerful pain
killer in Chinese medicine
Has hypotensive
properties

67. Alkaloids: ISOQUINOLONE
CORYDALIS Yan Hu Suo
Tetrahydropalmatine
(THP)
 THP found in Corydalis
 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
http://en.wikipedia.org/wiki/Tetrahydropa6lm7atine
Link:

68. Alkaloids: ISOQUINOLONE
POPPY (Papaver somniferum)
68 68
 Morphine
 Codeine

Papaverine

69. Alkaloids: ISOQUINOLONE
POPPY Morphine
69
Powerful analgesic,
narcotic
sedative and
anti-spasmodic
Morphine has derived
its
name from the Greek
God of sleep
Morpheus

70. Alkaloids: ISOQUINOLONE
POPPY Morphine
70 70
CNS Depressant
Exact Mechanism of
action unknown
Believed to prevent
the release of
acetylcholine
which blocks the
perception of pain
Link
http://www.elmhurst.edu/~chm/vchemb
ook/674narcotic.html

71. Alkaloids: ISOQUINOLONE
BLOODROOT (Sanguinaria canadensis)
71 71
Major constituents:
sanguinarine &
chelerythrine
Sanguilutine, sanguirubine,
chelilutine, chelirubine
Antifungal, antibacterial,
anti-inflammatory
Highly effective against
dental plaque bacteria
Sanguinarin
LG e

72. Alkaloids: ISOQUINOLONE
72 72
BLOODROOT
 Antibacterial, antiviral
against HPV and
condylomata (genital warts)
 Used to treat cervical
dysplasia & cancer-in-situ
 Used in Mouthwash to
stimulate epithelial growth
and repair of gingival tissue
LG

73. Alkaloids: ISOQUINOLONE
BLOODROOT
http://www.vitaminshoppe.com/content/en/healthguide
/hncontent.jsp?
intsource=hc&org=VSI&ContentID=2047005&categ
ory=Herb&title=Bloodroot&type=
73 73
Bloodroot Medicinal Use:

74. 74
Alkaloids:
 Indole
Indian Snakeroot
(Rauwolfia serpentina)
home.caregroup.org/.../Herbs/Rauwolfia_serpe.htm

75. 75
Alkaloids: INDOLE
Includes:
Reserpine
Harmine
Quinine
Yohimbine

76. Alkaloids: INDOLE
Indian Snakeroot (Rauwolfia serpentina)
home.caregroup.org/.../Herbs/Rauwolfia_serpe.htm
http://photos.merinews.com/upload/imageGallery/bigImage/1242386705661-snake
76 76
%20root%20plant.jpg

77. Reserpine:
Lowers BP, decreases
catecholamines
Peripheral
vasodilation
Depression 15% of
patients
77 77
Alkaloids: INDOLE
Reserpin
e
Indian Snakeroot

78. Harmine:
Powerful relaxant
with serotonin-like
action
Entheogen in high
amounts
78 78
Alkaloids: INDOLE
Passion Flower (Passiflora incarnata)

79. Medicinal Use of
Passion Flower:
79 79
Alkaloids: INDOLE
Passion Flower
http://www.vitaminshoppe.com/c
ontent/en/healthguide/hncontent.
jsp?
org=VSI&ContentID=2142002&c
ategory=Herb&title=Passion
%20Flower&type=

80. 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
80 80
Alkaloids: INDOLE

81. 81 81
Alkaloids: INDOLE
Yohimbine
Two sterioisomers: Alpha and Beta
NON SUPERIMPOSIBLE
MIRROR IMAGES
LG

82. X
Alkaloids: INDOLE
R enantiomer S enantiomer
X
Receptor binding site
Receptor binding site
LG
Why isomerism matters: receptor 8s2pecificity

83. Gelsemium (Gelsemium sempervirens)
83 83
Alkaloids: INDOLE
YELLOW JASMINE

84. Gelsemine Used in homeopathy
for
Dull
Droopy
Drowsiness
Flu weakness myalgia
Neuralgia
Migraines
Visual disturbances
84 84
Alkaloids: INDOLE

85. Alkaloids: QUINOLINE
CHINCHONA (Cinchona pubescens)
85 85
www.Rain-tree.com

86. Alkaloids: QUINOLINE
Common names: Quinine bark,
quinine,
China bark, Peruvian bark, Jesuit's
bark,
Quina-quina, Calisaya bark, Fever
tree
86 86
CHINCHONA
Alkaloids:
 Quinine
 Quinidine
 Cinchonidine

87. Alkaloids: QUINOLINE
87 87
Quinine

88. Alkaloids: QUINOLINE
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.
88 88
Quinine

89. Alkaloids: QUINOLIZIDINE
89 89
Scotch Broome
(Cytisus
scoparius)
Alkaloid:
Sparteine