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1 Alkaloids Introduc1on and Importance to Humans fentanyl
2 Alkaloids Introduction and Importance to Humans (alkaloids are pharmaceutically and ecologically significant)
3 Introduc)on to alkaloids, and importance to humans Define: = small organic molecules (secondary metabolites) of plants which contain nitrogen (typically in a ring) - alkaloids are pharmaceu)cally significant - tradi1onal and modern uses (25%/75% of drugs are plant derived, mostly alkaloids) - many have neurological effects - presumed due to the presence of nitrogen (mimic neutrotransmieers) - potent toxins and defenses - many highly toxic compounds, and with strong biological effects - interes1ng chemical ecology and co- evolu1on with insects
4 Alkaloid physiological effects are diverse: Quinine (Cinchona officinalis) - an)bio)cs (an1- malarial) Morphine (Papaver somniferum - painkiller (analgesic) Taxol - (Taxus brevifolia) Vinblas)ne (Catharanthus roseus) - an)cancer drug Coniine (Conium maculatum) - toxin Nico)ne (Nico@ana tabacum) insec1cide, s1mulant Atropine(Atropa belladonna) dilate pupils Cocaine (Erythroxylon coca) Tubocurarine (Chondodenron tomentosum) - muscle relaxant
5 General Features and Characteris)cs - N makes them basic in solu1on - > called alkaloids for this reason - structurally diverse: 12,000+ structures - 20% of all plant species have alkaloids - concentrated in specific plant taxa (families, genera, species), but are 'scaeered around' the plant kingdom (independent evolu1on) - biosynthe1cally diverse (arise from different amino acids) - strong biological effects (see ecological examples)
6 Examples of diverse mechanisms of ac)on: - bind/block neuroreceptors (morphine, codeine) - block reuptake of neuroreceptor (cocaine- dopamine) - disrupt cytoskeleton - tubulin (taxol) - mimic neurotransmiker ac)on (nico1ne - acetylcholine) - block cellular signaling (camp phosphodiesterase - caffeine)
7 Alkaloid Families and Biosynthesis (mostly derived from amino acids) Non-protein amino acids: not considered alkaloids but also toxins Heldt, Fig 16.1
8 Pseudoalkaloids: N added late in biosynthesis Protoalkaloids: N not in ring α-solanidine (tripterpene alkaloid of potato)
9 Biosynthesis of Alkaloids General features of alkaloid biosynthesis: - many biosynthe1c steps are required - > complex structures - any one plant typically accumulates a mix of related alkaloids - usually begins with decarboxyla)on of amino acid (eg) tyr - > tyramine, trp - > tryptamine - central intermediate can give rise to different final products: (strictosidine for diverse quinoline alkaloids, re)culine for isoquinoline and poppy alkaloids)
10 Biosynthesis of Quinoline Alkaloids & Central Position of Strictosidine Strictosidine Vincristine/ Vinblastine (monoterpene indole alkaloids C. Bowsher, Plant Biochemistry p. 342
11 Central Position of Reticuline in Isoquinoline Alkaloid Synthesis Isoquinoline Alkaloids Reticuline C. Bowsher, Plant Biochemistry p
12 Biosynthesis of Alkaloids Alkaloids can have organ- specific synthesis and storage: i.e., bark, roots, flowers There is also cell- specific synthesis / storage: - latex ducts and la1cifers for poppy alkaloids - epidermis, idioblasts for Vinca alkaloids Madagascar periwinkle (Catharanthus roseus) Opium poppy (Papaver somniferum)
13 Localiza1on of alkaloid synthesis opium poppy Biosynthesis of components in different cell types: - root and phloem parenchyma cell - la1cifers and idioblasts (DAT)
14 Localiza1on of Vinca alkaloid synthesis in Madagascar periwinkle (Catharantus roseus) phloem parenchyma cells Biosynthesis of components in different cell types: - phloem parenchyma cells (DXS, DXR) - epidermis (TDC, STR) - la1cifers and idioblasts (DAT)
15 Catharanthine accumulates almost en1rely in leaf wax exudates outside of the leaf epidermis, whereas vindoline is found within leaf cells. leaf surface (chloroform wash) chloroform wash whole leaf extract aaer chloroform wash Roepke J et al. PNAS 2010;107: by National Academy of Sciences
16 Model for biosynthesis and secre1on of secondary metabolites produced in the epidermis of C. roseus leaves. Roepke J et al. PNAS 2010;107: by National Academy of Sciences
17 Catharanthine is toxic to insect larvae (silk worm) Catharanthine is also toxic to pathogenic fungi (not shown)
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