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Alkaloids: Alkaloids Definition: the term alkaloid (alkali-like) is commonly used to designate basic heterocyclic nitrogenous

compounds of plant origin that are physiologically active


Distribution and occurrence: Rare in lower plants. Dicots are more rich in alkaloids than Monocots. Families rich in Alkaloids: Apocynaceae , Rubiaceae , Solanaceae and Papaveracea . Families free from Alkaloids: Rosaceae , Labiatae Distribution in Plant:: Distribution in Plant : All Parts e.g. Datura . Barks e.g. Cinchona Seeds e.g. Nux vomica Roots e.g. Aconite Fruits e.g. Black pepper Leaves e.g. Tobacco Latex e.g. Opium

Forms of Alkaloids::
Free bases Salts with Organic acids e.g. Oxalic, acetic acids Salts with inorganic acids e.g. HCl, H 2 SO 4 . Salts with special acids: e.g. Meconic acid in Opium Quinic acid in Cinchona Glycosidal form e.g. Solanine in Solanum Forms of Alkaloids:

Function in Plants:
They may act as protective against insects and herbivores due to their bitterness and toxicity. In certain cases, the final products of detoxification ( waste products) . Source of nitrogen in case of nitrogen deficiency.act as growth regulators in certain metabolic systems.

Nomenclature:: Trivial names should end by " ine " .these names may
refer to: The genus of the plant, such as Atropine from Atropa belladona . The plant species , such as Cocaine from Erythroxylon coca . The common name of the drug, such as Ergotamine from ergot. The name of the discoverer , such as Pelletierine that was discovered by Pelletier.The physiological action , such as Emetine that acts as emetic, Morphine acts as narcotic. A prominent physical character , such as Hygrine that is hygroscopic.

Prefixes and suffixes: : Prefixes: "Nor-" designates N- demethylation or Ndemethoxylation , e.g. norpseudoephedrine and nornicotine . "Apo-" designates dehydration e.g. apomorphine . " Iso -, pseudo-, neo-, and epi -" indicate different types of isomers. Suffixes: "-dine" designates isomerism as quinidine and cinchonidine . "- ine " indicates, in case of ergot alkaloids, a lower pharmacological activity e.g. ergotaminine is less potent than ergotamine

Physical Properties:: I- Condition: Most alkaloids are crystalline solids .


Few alkaloids are amorphous solids e.g. emetine. Some are liquids that are either: Volatile e.g. nicotine and coniine, or Non-volatile e.g. pilocarpine and hyoscine . II- Color: The majority of alkaloids are colorless but some are colored e.g.: Colchicine and berberine are yellow. Canadine is orange. The salts of sanguinarine are copper-red

Chemical Properties:: I- Nitrogen: Primary amines R-NH 2 e.g. Norephedrine


Secondary amines R 2 -NH e.g. Ephedrine Tertiary amines R 3 -N e.g. Atropine Quaternary ammonium salts R 4 -N e.g d Tubocurarine II- Basicity : R 2 -NH > R-NH 2 > R 3 -N Saturated hexacyclic amines is more basic than aromatic amines.

According to basicity Alkaloids are classified into: According to basicity


Alkaloids are classified into Weak bases e.g. Caffeine

Strong bases e.g. Atropine Amphoteric * Phenolic Alkaloids e.g. Morphine Alkaloids with Carboxylic groups e.g. Narceine Neutral alkaloids e.g. Colchicine Extraction, Purification and Isolation of Alkaloids from Powdered plants: Method I: The powder is treated with alkalis--------- to liberates the free bases that can then be extracted with water immiscible organic solvents.
Method II: The powdered material + extracted + water or aqueous alcohol containing dilute acid . Alkaloids are extracted as their salts together with accompanying soluble impurities . Method III: The powder + extracted + water soluble organic solvents such as MeOH or EtOH which are good solvents for both salts and free bases

Quinoline e.g.quinine and quinidine

natural white crystalline alkaloid having


antipyretic (fever-reducing), antimalarial, analgesic (painkilling), anti-inflammatory properties and a bitter taste
Quinidine:Antiarrhythmic agents are a group of pharmaceuticals that are used to suppress abnormal rhythms of the heart (cardiac arrhythmias

Isoquinoline e.g. papaverine


Papaverine ( /ppvrin/)[1] is an opium alkaloid antispasmodic drug(drug supress involuantry contraction of muscle), used primarily in the treatment of visceral spasm, vasospasm (especially those involving the heart and the brain), and occasionally in the treatment of erectile dysfunction.(sexual dysfunction characterized by the inability to develop or maintain an erection of the penis during sexual performanc)

Phenantherene e.g. Morphine phenanthrene is a composite of phenyl and anthracene

An alkaloid extracted from opium: used in medicine as an analgesic(RELIEVE PAIN) and sedative Sedative: A drug that calms a patient down, easing agitation and permitting sleep,

Slide 15: Indole e.g.ergometrine Imidazole e.g. pilocarpine Purine e.g. caffeine Slide 16: Steroidal e.g. Solanum and Veratrum alkaloids Terpenoid e.g. Taxol

Phenantherene e.g. Morphine phenanthrene is a composite of phenyl and anthracene

An alkaloid extracted from opium: used in medicine as an analgesic(RELIEVE PAIN) and sedative Sedative: A drug that calms a patient down, easing agitation and permitting sleep,

Slide 15: Indole e.g.ergometrine Imidazole e.g. pilocarpine Purine e.g. caffeine Slide 16: Steroidal e.g. Solanum and Veratrum alkaloids Terpenoid e.g. Taxol

Slide 15: Indole e.g.ergometrine

Ergometrine can be used to control excessive bleeding following childbirth. Ergometrine helps the uterus contract back and controls blood loss as it does this. Imidazole e.g. pilocarpine

Pilocarpine is a parasympathomimetic alkaloid ( a drug or poison that acts by stimulating or mimicking the parasympathetic nervous system (PSNS)he parasympathetic nervous system (PSNS) is one of the two main divisions of the autonomic nervous system (ANS). The ANS is responsible for regulation of internal organs and glands, which occurs unconsciously. To be specific, the parasympathetic system is responsible for stimulation of "rest-and-digest" activities that occur when the body is at rest, including sexual arousal, salivation, lacrimation (tears), urination, digestion, and defecation.

Purine e.g. caffeine

Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant i drug It is most commonly consumed by humans in infusions extracted from the bean of the coffee plant and the leaves of the tea bush

Terpenoid : taxol

Taxol is Chemotherapy drug that is given for breast cancer.

Pyrrolizidine alkaloids: Pyrrolizidine alkaloids

Pyrrolizidine alkaloids (PAs) are a group of naturally occurring alkaloids based on the structure of pyrrolizidine.

Tropane alkaloids: Tropane alkaloids:bELLADONA TYPE:ATROPINE i

Tropane is a nitrogenous bicyclic organic compound. It is mainly known for a group of alkaloids derived from it (called tropane alkaloids), which include, among others, atropine and cocaine tropane

atropine

Atropine :An anticholinergic agent is a substance that blocks the neurotransmitter acetylcholine in the central and the peripheral nervous system. Cocaine: a crystalline alkaloid from the coca plant. It acts as a stimulant, appetite suppressant, and anesthetic

Tropane Alkaloids: Tropane Alkaloids They are ester alkaloids resulted from the coupling of organic acids with amino alcohol (Base). The parent base is the Tropane base. Tropane Alkaloids are classified into: 1- Solanaceous Tropane Alkaloids. 2Erythroxylon ( Coca ) Alkaloids. STRUCTURE OF TROPANE

Ephedra Ephedraceae sinica: Ephedra Ephedraceae sinica An evergreen shrub native to central Asia Predominant active alkaloid- ephedrine Other active alkaloids include: pseudoephedrine norephedrine norpseudoephedrine PHENYLPROPANOL AMINE

SES: Phenylpropanolamine (PPA) is used to treat nasal congestion associated with the common cold, allergies, hay fever,
Phenylpropanolamine Hydrochloride

AMPHETAMINE

drugs that increase levels of the neurotransmitters norepinephrine, serotonin, a dopamine in the brain. They are commonly used as stimulants and appetite suppressants. t

drugs that increase levels of the neurotransmitters norepinephrine, serotonin, and dopamine in the brain. They are commonly used as stimulants and appetite suppressan

Epinephrine, also known as adrenalin , is a hormone that is responsible for the "fight or flight" reaction in mammals. Chemically, it mobilizes the body's defense system, inducing the release into the blood of large amounts of glucose from stores in the liver and muscles. This burst of energy is the familiar "adrenalin rush" one experiences when frightened or excited.

Serotonin, a hormone found in the brain, is a neurotransmitter which has much control over several brain functions. Serotonin, also known as 5-hydroxytryptamine, 5HT, is also found in other areas of the body including the central nervous system, the intestinal wall, and the large blood vessels.Serotonin deficiency or a decrease in the serotonin level is most likely to blame for depression, aggression, anxiousness, and elevated pain sensitivity.

Dopamine is a neurotransmitter that is naturally produced in the body. It is present in the regions of the brain that regulate movement, emotion, motivation and the feeling of pleasure.Since Dopamine is a chemical messenger, it is similar to adrenaline. It activates the dopamine receptors. Patients suffering from Parkinsons disease lack Dopamine in the brain. To remedy that, a synthetic precursor to dopamine such as L-DOPA can be given, since this will cross the blood-brain barrier.

What is Ephedrine So what exactly is ephedrine? Classified as a sympathomimetic drug (a beta-1 and beta-2 adrenergic receptor agonist), its a central nervous system stimulant that increases serum levels of norepinephrine. The herbs ma huang, ephedra sinica and Sida cordifolia contain ephedrine, which structurally is similar to amphetamines.1 . Drugs that are more selective beta-2 agonists are generally preferred for treatment of asthma.1

Ephedrines Role in Athletic Performance and Weight Loss

Structures: Vinblastine (Vincaleukoblastine) is produced by coupling of Catharanthine and Vindoline.(breast cancer and bleeding) Vinblastine is used for: Treating certain types of cancer. It is usually used in combination with other antineoplastic agents. Vinblastine is an antineoplastic agent. It works by interfering with the reproduction of tumor cells. antineoplastic agents travel the body and destroy cancer cells

Vincristine (leurocristine) has CHO istead of CH 3 in the vindoline part of Vinblastine.(childhood tumor and constipation) Vincristine is a naturally occurring compound that is extracted from periwinkle plants. It belongs to a group of chemicals called alkaloids. The chemical structure and biological action of vincristine is similar to vinblastine Vincristine prevents the formation of microtubules in cells. treat leukemia. It to treat Hodgkin's disease. Vincristine is also used less frequently to treat other types of cancer.

Hemlock type(pyridine/piperidine ) alkaolid Piperidine alkaloids: Piperidine alkaloids Structure of coniine

Poison hemlock-conium Indian tobacco-lobelia

Semisynthetic derivatives:: Semisynthetic derivatives: Vindesine: It is used for treatment of acute lymphoid leukemia in children.

Vinorelbine: It is an oral anticancer with broader activity and lower neurotoxicity than vinblastine .

Piperidine/Pyridine alkaloids: Piperidine /Pyridine alkaloids

Nicotine/tobacco type(pyrollidine-pyridine derivative) structure of nicotine

Purine alkaloids: Purine alkaloids Figure 3-5 Caffeine COFEE or CAFFEINE TYPE(PURINE ALKALOID) STRUCTURE OF CAFFEINE

Diterpenoid alkaloids: Diterpenoid alkaloids-larspur type-diterpenoid type

Amine alkaloids: Amine alkaloids Alkaloids without heterocyclic nitrogen atoms Mescaline type

Quinoline alkaloids: Quinoline alkaloids STUCTURE OF QUININE:

Quinine tree-Cinchona

ISoquinoline alkaloids: Isoquinoline alkaloids-OPIUM/MORPHINE TYPE

Indole alkaloids: Indole alkaloids Vindoline Vinblastine ( Catharanthus ) ERGOT TYPE(INDOLE ALKAOID)ERGONOVINE

Lupine type(Quinolizidine alkaloids) that is cytisine type) Lupinine structure

STEROIDAL ALKALOID(TOMATO/Solanine typeglycoalkaoid) Solanidine

Steroidal alkaloid(veratrum type) Veratramine

Alkaloid synthesis: 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

ISoquinoline alkaloids: Isoquinoline alkaloids-OPIUM/MORPHINE TYPE

Indole alkaloids: Indole alkaloids Vindoline Vinblastine ( Catharanthus ) ERGOT TYPE(INDOLE ALKAOID)ERGONOVINE

Alkaloid class pyrolidine

Biosynthetic precursor ornithine

example nicotine

tropane
piperidine yrrolizidine

ornithine
lysine(or acetate) ornithine

Atropine,cocaine
coniine retrosine

quinolizidine
isoquinoline indole

lysine
tyrosine tryptophan

lupinine
morphine Reserpine, strychnine