Alkaloids

Alkaloids are a diverse group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. They are produced by a large variety of organisms including bacteria, fungi, plants, and animals. Many alkaloids are toxic to other organisms and are produced as secondary metabolites for defense.

Many alkaloids are toxic...

Diagram of alkaloid biosynthesis
Figure 1: Phase 1: The "Common Pathway" (Tyrosine to Reticuline)
Diagram of nicotine chemical structure
Figure 2: Nicotine Structure

1. Chemical Classification

Amino Alkaloids (Protoalkaloids)

Derived from amino acids but lack the nitrogen in the heterocyclic ring.

  • Ephedrine: Ephedra spp.
  • Mescaline: Lophophora spp. (Cacti)
  • Colchicine: Colchicum autumnale
Aporphine Alkaloids
  • Boldine: Peumus boldus
  • Magnoflorine: Mahonia spp. (Oregon Grape)
Indole Alkaloids

Derived from Tryptophan.

  • Vincamine: Vinca minor
  • Psilocybin: Psilocybe spp. (Fungi)
  • Strychnine: Strychnos nux-vomica
  • Gramine: Phalaris arundinacea (Reed Canary Grass)
Isoquinoline Alkaloids

Derived from Tyrosine.

  • Berberine: Mahonia spp., Berberis spp.
  • Morphine/Codeine: Papaver somniferum
  • Sanguinarine: Sanguinaria canadensis
Piperidine Alkaloids

Derived from Lysine or Acetate. Often highly toxic.

Purine Alkaloids (Xanthines)

Pseudoalkaloids related to DNA bases.

  • Caffeine: Camellia sinensis, Coffea
  • Theobromine: Theobroma cacao
Pyrrolizidine Alkaloids (PAs)

Hepatotoxic compounds derived from Ornithine.

  • Senecionine: Senecio jacobaea (Tansy Ragwort)
  • Symphytine: Symphytum officinale (Comfrey)
  • Cynoglossine: Cynoglossum officinale (Houndstongue)
Quinoline Alkaloids
  • Quinine: Cinchona spp.
  • Dictamnine: Dictamnus albus
Quinolizidine Alkaloids

Derived from Lysine. Common in Fabaceae.

Steroidal Alkaloids

Based on a triterpene skeleton.

Tropane Alkaloids

Derived from Ornithine. Anticholinergic properties.

  • Scopolamine: Datura stramonium (Jimsonweed) Toxic
  • Atropine: Atropa belladonna
  • Hyoscyamine: Hyoscyamus niger (Henbane)

2. Detailed Chemical Profiles

Berberine (Isoquinoline)

  • Berberine is from the protoberberine group of isoquinoline alkaloids [Ramawat NP]
  • "Pharmacological data also suggest that combining berberine-containing herbs with other botanical synergists might prove even more effective." (CBMed)
  • Berberine salts have been used in ophthalmic products, usually in eye drops and eyewashes. [Leung ENCI]
  • Interactions:
    • Ciclosporin: "Berberine appears to increase the bioavailability and trough blood levels of ciclosporin.... Although the increase in ciclosporin levels is not sufficiently severe to suggest that the concurrent use of berberine should be avoided, it may make ciclosporin levels less stable." [HMI Stockey]
    • Paclitaxel: An in vitro study found that pre-treatment with berberine blocked the anticancer effects of paclitaxel in six cancer cell line cultures (oral cancer, gastric cancer and colon cancer). [HMI Stockey]

Distribution: Mahonia spp. (Oregon Grape), Berberis spp., Coptis spp., Hydrastis canadensis.

Activities: Antibacterial, antifungal, amoebicidal, antiarrhythmic, antiinflammatory. "Berberine has marked antibacterial effects and is used as a bitter tonic... Since it is not appreciably absorbed by the body, it is used orally in the treatment of various enteric infections." (PFAF)

Cytisine (Quinolizidine)

Also known as: Ulexine, Baptitoxine, Sophorine.

Distribution: Laburnum spp., Cytisus scoparius (Scotch Broom), Sophora secundiflora (Mescal bean).

Hazards

  • Toxicity: "A piece of the root the size of a pea can kill a man." [Remington USD20]
  • Teratogenic: Implicated as teratogens in higher animals. [Rosenthal HerbV1]

Pharmacology

"Cytisine binds strongly to nicotinic receptors, causing initially stimulation and at higher doses blockade of the ganglionic receptors similar to the effects of curare." [DP2] It has served as the lead compound for varenicline (smoking cessation drug).

Muscarine

"The first drug known to have a selective action on organs innervated by the autonomic nervous system." [ACP23]

Distribution

  • Amanita muscaria (Fly Agaric)
  • Clitocybe dealbata & C. rivulosa (Sweating Mushrooms)
  • Inocybe spp. (Fiber caps)

Symptoms (PSL Syndrome)

"Profuse sweating is the most frequent symptom, often accompanied by salivation and lacrimation (production of tears)... within 15 to 30 minutes." [Trudell MPNW]

Solanine & Solanidine (Steroidal Glycoalkaloid)

Toxic alkaloids found in Solanaceous plants. "Solanine... inhibits RNA reverse transcriptase... and causes hemolysis of membranes." [Reigosa Alleleopathy]

Distribution

  • Solanum tuberosum (Potato) - especially green skins and sprouts.
  • Solanum nigrum (Black Nightshade) - unripe berries.
  • Solanum dulcamara (Bittersweet Nightshade) - whole plant.

Toxicity & Cooking

"Unfortunately glycoalkaloids are heat stable... boiling (4.7% loss), microwaving (15% loss) and deep-frying (nil loss)... Unpeeled potatoes will retain their toxicity no matter what type of cooking process is used because the highest alkaloid levels are located within the 1 mm from the outside surface." [Cheryll_Williams]

Symptoms: Nausea, diarrhea, burning throat, cardiac dysrhythmia, hallucinations, paralysis. Doses of 3-6 mg/kg can be fatal.

Veratridine (Steroid-derived)

A neurotoxin that binds to voltage-gated sodium channels.

Distribution: Veratrum viride (False Hellebore), Schoenocaulon officinale.

Activity: "The toxic effects... are more morbidly impressive and violent than those from coniine."

Alkamides (see Amines) (Fatty Acid Amides)

"In alkamides, amines are combined with unsaturated fatty acids by amide linkages... responsible for the sharp, burning or tingling taste associated with herbs." [Pengelly TCMP]

CompoundNotable SourcesActivity
Spilanthol Spilanthes spp. Analgesic, "Toothache plant" effect.
Pellitorine Piper longum Insecticidal.
Sanshool Zanthoxylum (Prickly Ash) Tingling sensation.
Dodeca-2E,4E-dienoic acid isobutylamide Echinacea spp. Immunomodulatory, inhibits COX-2.

Amines (Biogenic)

"Low molecular weight organic bases... formed by the decarboxylation of amino acids."

  • Melatonin (Indolamine): Found in walnuts, cherries, and various seeds. Regulates circadian rhythm.
  • Polyamines (Spermine, Spermidine, Putrescine): Found in various plant tissues; involved in cell proliferation.
  • Tyramine: Can cause hypertensive crisis in individuals taking MAOIs. Found in aged/fermented foods.

References & Citations

[1.1] Stegelmeier, B.L. (2011). "Pyrrolizidine Alkaloid–Containing Toxic Plants." USDA-ARS.

[1.2] Merck Veterinary Manual, "Pyrrolizidine Alkaloidosis in Animals."

[2.1] Panter, K.E. et al. (2012). "Piperidine alkaloids: human and food animal teratogens." PubMed.

[3.3] Galiano Conservancy, "Meet the Plants: Phalaris arundinacea."

[5.1] PMC 7153348, "Analysis of alkaloids (indole, isoquinoline, tropane)."

[5.2] Britannica, "Alkaloid Classification."

[5.4] Wikipedia, "Solanaceae/Alkaloids."

Note: Citations marked [User Source] refer to original text provided in the Eflora database (e.g., MNP Dewick, Pengelly TCMP).