Alkaloids

Alkaloids

 Distribution
 Properties
 Role in plants
 Defense compounds
 Animal poisoning
 Lupine
 Groundsel
 Larkspur
 Jimson weed (Scopolamine)
 Henban (Atropine)
 Other roles in plants
Lupines
Texas bluebonnet
Effects of alkaloids on humans

 High biological activity

 Produce varying degrees of physiological and
psychological responses - largely by interfering with
neurotransmitters
 others interfere with membrane transport, protein synthesis
or other processes
 In large doses - highly toxic - fatal
 In small doses, many have therapeutic value
 muscle relaxants, tranquilizers, pain killers, mind altering
drugs, chemotherapy
Psychoactive alkaloids
 Although only a small percent are psychoactive,
these get much focus
 Affect the central nervous system - often by
influencing neurotransmitters
 Categories of psychoactive cmpds
 Stimulants
 Hallucinogens
 Depressants
 May also be narcotic (addictive)
Psychoactive alkaloids

Stimulants Hallucinogens Depressants

Cocaine Tropane alkaloids Morphine

Ephedrine Mescaline Codeine

Caffeine Psilocybin Heroin

Ergot alkaloids (LSD)

Alkaloid synthesis

 Most alkaloids are synthesized from a few common

amino acids (tyrosine, tryptophan, ornithine or
argenine, aspartic acid, & lysine)
 Nicotinic acid precursor for part of nicotine
 Purine precursor for caffeine
 Some alkaloids synthesized from terpenes - along
mevalonic acid pathway
 Generally classified by the predominant ring
structure and/or carbon skeleton
Tropane alkaloids

Many of these psychoactive alkaloids

Pyrrolizidine alkaloids
Piperidine alkaloids
Piperidine/Pyridine alkaloids
Purine alkaloids

Figure 3-5 Caffeine

Quinoline alkaloids
Isoquinoline alkaloids
Indole alkaloids

Vindoline
Vinblastine (Catharanthus)
Quinolizidine alkaloids
Steroidal alkaloids
Steroidal alkaloids
Diterpenoid alkaloids
Amine alkaloids

Alkaloids without heterocyclic nitrogen atoms

Other classes of alkaloids

 Betalain alkaloids - pigment alkaloids

 Lycopodium alkaloids - restricted to club
mosses
 Peptide alkaloids