alkaloid biosynthesis

sunlight + water = ENERGY + SUGAR cysteine, glycine, serine tryptophan QUINOLINE: quinine INDOLE: vinblastine, reserpine, ergotamine strychnine, ajmalicine, yohimbine, psilocybin, harmaline shikimate pathway purines XANTHINE: caffeine theobromine, theophylline phenylalanine Glycolysis cinnamic acid ISOQUINOLINE: berberine papaverine, sanguinarine, opium morphine, codeine, corydaline tyrosine

nucleic acids alkaloids

SUGARS

(PEP)

PHENYLALKYLAMINE: cocaine, mescaline, ephedrine

amino acids pyruvate amino acids, alkaloids mevalonate/deoxyxylulose h TERPENOID: aconitine IRIDOIDAL: Valerian alkaloids STEROIDAL: solanidine,Veratrum alk. acetate / polyketide pathway coniine glutamate cadaverine lysine QUINOLIZIDINE: PIPERIDINE: lupinine lobeline sparteine ornithine

amino acids

acetyl-CoA aspartate

Citric Acid Cycle

TROPANE: atropine, hyoscyamine, scopolamine, nicotine putrescine PYRROLIZIDINE: symphytine, senecionine, hygrine

histidine INDOLIZIDINE: swainsonine, castanospermine

IMIDAZOLE: pilocarpine

ALKALOIDS DERIVED FROM AMINO ACIDS

Tryptophan Indole vinblastine (Cantharanthus) is synthesized as an anticancer drug reserpine (Rauwolfia) is synthesized as a drug to lower blood pressure ergotamine (Claviceps purpurea) is synthesized as a migraine vasoconstrictor drug Quinoline quinine (Cinchona) is antimalarial over 30 quinoline alkaloids are found in rue (Ruta graveolens) Xanthoxylum sp. (prickly ash) contains quinoline alkaloids Phenylalanine Phenylalkylamine cocaine (Erythroxylum), mescaline (Lophophora), ephedrine (Ephedra) Tyrosine Isoquinoline berberine (Berberis) is antimicrobial and astringent papaverine (Papaver) and other morphine alkaloids are analgesic and most are addictive sanguinarine (Sanguinaria) Ornithine Tropane atropine, hyoscyamine, scopolamine (Atropa, Hyoscyamus, Datura) act on the central nervous system nicotine (Nicotiana) is an irritant and paralyzant Pyrrolizidine symphytine (Symphytum and Cynoglossum) and senecionine (Senecio) have hepatotoxic properties; some pyrrolizidine alkaloids (e.g., those found in Echinacea) are not hepatotoxic Aspartate Quinolizidine lupinine (Lupinus) is poisonous to livestock sparteine (Chelidonium, celandine) and (Sarothamnus scoparius, scotch broom) Lysine Piperidine (these alkaloids stimulate, then block autonomic nervous activity) lobeline (Lobelia inflata) is a parasympathomimetic Histidine Imidazole pilocarpine (Pilocarpus jaborandi) is used to relieve glaucoma symptoms Non-amino acid alkaloids: Purine / Xanthine caffeine (Caffea), theobromine (Theobroma cacao), theophylline (Camillia) are stimulant Terpenoid (alkaloids made from components of the mevalonate and deoxylulose pathways: delphinine (Delphinium), aconitine (Aconitum), solanine (Solanum) Steroid (alkaloids made from components of the mevalonate pathway) protoveratrines (Veratrum, false hellebore)