Quinoline and Isoquinoline Alkaloids
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Questions and Answers

What is the primary biosynthetic origin of quinoline alkaloids?

  • Fulvic acid
  • Lactic acid
  • Tyrosine
  • Anthranilic acid (correct)

Which plant family is recognized as a rich source of quinoline alkaloids?

  • Rubiaceae (correct)
  • Berberidaceae
  • Annonaceae
  • Rutaceae

Which of the following is NOT a property of quinine?

  • Anti-inflammatory
  • Antipyretic
  • Analgesic
  • Antihypertensive (correct)

From which amino acid are isoquinoline alkaloids derived?

<p>Tyrosine (B)</p> Signup and view all the answers

Isoquinoline alkaloids are commonly found in which of the following plant families?

<p>Berberidaceae (B)</p> Signup and view all the answers

What characteristic do quinidine and quinine share?

<p>They are both present in cinchona bark. (A)</p> Signup and view all the answers

The quinoline nucleus has become important in what area of research?

<p>Anticancer compound development (B)</p> Signup and view all the answers

Which alkaloid is associated primarily with Cephaelis ipecacuanha?

<p>Ipecacuanha alkaloids (B)</p> Signup and view all the answers

What type of alkaloids are noscapine and papaverine classified as?

<p>Benzyl-isoquinoline alkaloids (A)</p> Signup and view all the answers

What is the main use of naloxone?

<p>Narcotic antagonist for heroin addiction (D)</p> Signup and view all the answers

Which plant is the source of vinblastine and vincristine?

<p>Periwinkle plant (A)</p> Signup and view all the answers

What is the primary active compound found in Calabar beans?

<p>Eserine (D)</p> Signup and view all the answers

Which alkaloids are derived from the fungus Claviceps purpurea?

<p>Ergot alkaloids (C)</p> Signup and view all the answers

In which of the following is the distribution of indole alkaloids most prevalent?

<p>Found in both flowering plants and fungi (C)</p> Signup and view all the answers

What type of activity is primarily associated with narceine?

<p>Antispasmodic (C)</p> Signup and view all the answers

Which of the following is considered a synthetic form of an opioid?

<p>Heroin (D)</p> Signup and view all the answers

Which alkaloid is most active and less toxic for use in obstetrics?

<p>Ergometrine (A)</p> Signup and view all the answers

What is a symptom of ergot poisoning seen in Anthony's fire?

<p>Burning skin (B)</p> Signup and view all the answers

Which group of alkaloids is known to be water insoluble?

<p>Both B and C (B)</p> Signup and view all the answers

Which of the following alkaloids is primarily used for treating migraine headaches?

<p>Ergotamine (D)</p> Signup and view all the answers

What is the chemical formula for Ergometrine?

<p>C19H22O2N3 (D)</p> Signup and view all the answers

What is one of the main active ingredients in ipecac used for suspected poisoning?

<p>Cephalein (A)</p> Signup and view all the answers

Which alkaloid belongs to the ergotamine group and was discovered by Smith & Timmis?

<p>Ergosine (D)</p> Signup and view all the answers

What gastrointestinal effect can result from ergot poisoning?

<p>GIT effects such as nausea (C)</p> Signup and view all the answers

Which condition is a contraindication for the use of ipecac?

<p>Ulcers (C)</p> Signup and view all the answers

What notable effect is shared by all natural ergot alkaloids on the uterus?

<p>Induce contractions (C)</p> Signup and view all the answers

What type of receptors does tubocurarine act on?

<p>Cholinergic nicotinic receptors (A)</p> Signup and view all the answers

Which of the following is a potential risk of misuse of ipecac in individuals with anorexia nervosa?

<p>Severe myopathy (A)</p> Signup and view all the answers

Which of the following substances is considered a safer alternative to tubocurarine?

<p>Vecuronium (C)</p> Signup and view all the answers

What is the family classification of Papaver somniferum, the opium poppy?

<p>Papaveraceae (A)</p> Signup and view all the answers

What type of compound is tubocurarine classified as?

<p>Quaternary ammonium compound (C)</p> Signup and view all the answers

Which component of opium is known for its strong CNS depressant activity?

<p>Morphine (B)</p> Signup and view all the answers

Flashcards

Quinoline Alkaloid Origin

Quinoline alkaloids are derived from anthranilic acid.

Where are Quinoline Alkaloids Found?

Quinoline alkaloids are primarily found in plants belonging to the Rutaceae family, but also occur in the Annonaceae and Moraceae families.

Cinchona spp.

Cinchona species, belonging to the Rubiaceae family, are a rich source of quinoline alkaloids like quinine, quinidine, cinchonine, and cinchonidine.

Sterioisomers in Cinchona

Cinchona alkaloids exist as stereoisomers, with quinine and cinchonidine being (-) stereoisomers, while quinidine and cinchonine are (+) stereoisomers.

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Isoquinoline Alkaloid Origin

Isoquinoline alkaloids are derived from tyrosine.

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Isoquinoline Alkaloid Distribution

Isoquinoline alkaloids are widely distributed in various plant families, including Papaveraceae, Berberidaceae, Fumariaceae, Menispermaceae, Ranunculaceae, Rutaceae, and Annonaceae.

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Cephaelis Ipecacuanha

Cephaelis ipecacuanha, commonly known as ipecac, belongs to the Rubiaceae family and contains isoquinoline alkaloids in its roots.

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Uses of Quinoline Alkaloids

Quinine has antipyretic, antimalarial, analgesic, and anti-inflammatory properties, along with a bitter taste. Quinidine is used for treating cardiac arrhythmias.

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Ipecac: What does it do?

Ipecac is a plant that produces irritation in the stomach lining, inducing vomiting. It's often used in cases of suspected poisoning.

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Ipecac: When is it used?

Ipecac is used to induce vomiting in cases of suspected poisoning. It's also used for severe amoebic dysentery and as an expectorant to help clear the respiratory tract.

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Ipecac: Side effects?

While effective in some cases, Ipecac has several side effects including damage to the heart, liver, kidneys, intestines, and muscles. It's contraindicated in digestive disorders like ulcers and Crohn's disease.

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Tubocurarine: What is it?

Tubocurarine is an alkaloid found in the stems of the plant Chondodendron tomentosum, commonly known as curare. It belongs to the family Menispermaceae and is a powerful muscle relaxant.

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Tubocurarine: How does it work?

Tubocurarine works by blocking the transmission of nerve signals to muscles, leading to muscle paralysis. It acts as a competitive antagonist at cholinergic nicotinic receptors at the neuromuscular junction.

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Tubocurarine: Contraindications?

Tubocurarine is contraindicated in asthmatic patients and those with allergies due to potential respiratory issues. It's also contraindicated in patients with certain pre-existing conditions.

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Opium Poppy: What is it?

The opium poppy (Papaver somniferum) is a plant that produces opium, a dried milky exudate obtained from its unripe capsules.

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Opium Poppy: Key Compounds

Opium contains several important compounds, including morphine, codeine, and thebaine. These compounds are strong bases that have a high potential for central nervous system depression.

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Ergot Poisoning

A toxic condition caused by consuming ergot-infected grains, characterized by symptoms such as burning skin, hallucinations, gangrene, and gastrointestinal issues.

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Ergot Alkaloids

A group of naturally occurring compounds produced by the ergot fungus (Claviceps purpurea) that have powerful effects on the body.

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Ergometrine (Ergonovine)

A water-soluble ergot alkaloid known for its strong uterine contractions.

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Ergotamine

A water-insoluble ergot alkaloid primarily used to treat migraines.

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Ergotoxine Group

A group of water-insoluble ergot alkaloids that have various physiological effects.

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Lysergic Acid

A core component of ergot alkaloids, responsible for their physiological activity.

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Ergometrinine

A similar ergot alkaloid to ergometrine, also known for its uterine contractions.

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Ergotaminine

A similar ergot alkaloid to ergotamine, also used for migraines.

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What are benzyl-isoquinoline alkaloids?

Benzyl-isoquinoline alkaloids are a group of alkaloids that contain a benzyl-isoquinoline ring system. They are found in plants like opium poppy, and some have medicinal properties.

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What is Noscapine (Narcotine)?

Noscapine (Narcotine) is a benzyl-isoquinoline alkaloid found in opium poppy. It has an antispasmodic effect and is a weak base.

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What is Papaverine?

Papaverine is another benzyl-isoquinoline alkaloid found in opium poppy. It has antispasmodic activity and is a weak base.

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What is Naloxone?

Naloxone is a narcotic antagonist that blocks the effects of opioids like heroin. It has no analgesic effect, meaning it doesn't relieve pain.

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What are indole alkaloids?

Indole alkaloids are a class of alkaloids that contain an indole ring structure. They are often found in plants and sometimes fungi, and some have significant biological activity.

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What are Vinca alkaloids?

Vinca alkaloids are a group of alkaloids derived from the Catharanthus roseus plant (Periwinkle). They are used in cancer treatment, with notable examples being Vinblastine (VLB) and Vincristine (LC).

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What are ergot alkaloids?

Ergot alkaloids are derived from the fungus Claviceps purpurea, which grows on rye. They have medicinal properties and were historically known for causing ergotism, a disease characterized by symptoms like gangrene and hallucinations.

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What are Calabar beans?

Calabar beans are the dried seeds of Physostigma venenosum, a plant found in West Africa. They contain the alkaloid physostigmine (eserine), which has medicinal properties.

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Study Notes

Quinoline and Isoquinoline Alkaloids

  • Quinoline alkaloids are derived from anthranilic acid.
  • Isoquinoline alkaloids are derived from tyrosine.
  • Quinoline alkaloids are mainly found in Rutaceous plants, but also found in Annonaceae and Moraceae families.
  • Cinchona spp. belongs to the Rubiaceae family. The bark is a rich source of quinine, quinidine, cinchonine and cinchonidine.
  • Quinine has antipyretic, antimalarial, analgesic, anti-inflammatory properties and a bitter taste.
  • Quinidine is used for treating cardiac arrhythmias.
  • The quinoline nucleus is now of interest in the development of anticancer compounds.
  • Isoquinoline alkaloids are widely distributed in Papaveraceae (tetrahydro-bases), Berberidaceae, Fumariaceae, Menispermaceae, Ranunculaceae, Rutaceae, and Annonaceae plants.
  • Cephaelis ipecacuanha (ipecac) belongs to the Rubiaceae family. Alkaloids present in roots, used for suspected poisoning. Main active compounds include emetine, cephalein and psychotrine. Ipecac causes gastric irritation leading to vomiting.
  • Ipecac is used orally in suspected poisoning or severe amoebic dysentery, and as an expectorant. It is contraindicated in digestive disorders.
  • Large doses of emetine can damage the heart, liver, kidneys, intestinal tract, and skeletal muscles.
  • Misuse can lead to anorexia nervosa, bulimia, myopathy, lethargy, erythema, cardiotoxicity and even death.
  • Chondodendron tomentosum: stems are a source of curare (d-tubocurarine), belonging to the Menispermaceae family. Tubocurarine is a benzylisoquinoline type, quaternary ammonium compound. It is soluble in water and alcohol, but insoluble in chloroform, acetone and ether.
  • Tubocurarine is a competitive antagonist at cholinergic nicotinic receptors at the neuromuscular junction. It is relatively contraindicated in asthmatic patients and those with allergic tendencies. It is now replaced by safer skeletal muscle relaxants like rocuronium, vecuronium and atracurium.
  • Papaver somniferum: commonly known as opium poppy, belonging to the Papaveraceae family. Opium is the air-dried, milky exudate obtained from unripe capsules of the plant.
  • Morphine, Codeine, and Thebaine are phenanthrene-based, strong alkaline, highly toxic compounds with significant CNS depressant activity.
  • Noscapine (Narcotine), Narceine, and Papaverine contain benzyl-isoquinoline, are weak bases, slightly toxic and have significant antispasmodic activity.
  • Naloxone is a narcotic antagonist with no analgesic effect. Used in heroin addiction, competing with narcotics for sites on narcotic receptors.

Indole Alkaloids

  • Indole alkaloids are a class of alkaloids containing an indole structural moiety. Many include isoprene groups, and are thus called terpene indole or secologanin tryptamine alkaloids.
  • Indole alkaloids are widely distributed in flowering plants, also found in fungi (ergot) and some Convolvulaceae species.
  • Physostigma venenosum: Calabar beans (dried ripe seeds), west Africa, major active is physostigmine. Physostigmine (eserine) is present to the extent of 0.15-0.3%.
  • Vinca alkaloids: Obtained from Catharanthus roseus (periwinkle plant) of the Apocynaceae family. 90 alkaloids have been isolated. Vinblastine (VLB) and Vincristine (LC) are significant examples.

Ergot Alkaloids

  • Ergot is the dried sclerotium of the fungus Claviceps purpurea, arising in the rye ovary of Europe.
  • In the Middle Ages, humans suffered from St. Anthony's fire (ergot poisoning). Burning skin, insects crawling under skin, and loss of hands and feet (gangrene) were symptoms.
  • Six pairs of alkaloids are known, divided into three groups : water soluble (Ergometrine or Ergonovine), water insoluble (Ergotamine), and water insoluble (Ergotoxine) groups.
  • Alkaloids are combined with lysergic acid or isolysergic acid, which contribute to their physiological activity.
  • Ergot derivatives are used in obstetrics (for uterine contractions), prevention of migraine, and potentially Parkinson’s disease (dopamine agonists).

Assignment

  • Identification tests for different alkaloid classes.
  • Physical and chemical properties of quinoline and isoquinoline alkaloids.
  • Doses of ipecac used locally for various conditions.
  • Notes on Rauwolfia serpentina.

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Isoquinoline and Quinoline Alkaloids PDF, PHA 3, 1/7/2021

Description

Explore the fascinating world of quinoline and isoquinoline alkaloids, derived from anthranilic acid and tyrosine respectively. Learn about their sources, properties, and medicinal uses, including their role in treating malaria and cardiac arrhythmias. This quiz covers key plants and their alkaloid content.

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