Anthraquinones and Their Structure

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Questions and Answers

At what temperature does anthraquinone sublimate?

  • 200-220 oC
  • 160-180 oC (correct)
  • 220-240 oC
  • 100-120 oC

What is the color change observed when the sublimate of anthraquinone reacts with alkali?

  • Yellow
  • Blue
  • Green
  • Red (correct)

Which acid is used in Borntrager’s test for anthraquinones?

  • Acetic acid
  • Strong sulfuric acid
  • Dilute hydrochloric acid (correct)
  • Concentrated nitric acid

What is the result of boiling anthraquinone glycoside with hydrochloric acid?

<p>Release of anthraquinone (C)</p> Signup and view all the answers

What physical forms are yielded when anthraquinone sublimes?

<p>Needles or droplets (A)</p> Signup and view all the answers

What is the scientific name of the plant known as Senna tora?

<p>Senna tora (B), Cassia tora (C)</p> Signup and view all the answers

Which part of the Senna tora plant is primarily used for medicinal purposes?

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

Which of the following compounds is NOT listed as a key ingredient found in Senna tora?

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

What is a recognized use of Senna tora according to traditional practices?

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

Which family does the Senna tora plant belong to?

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

What is one of the primary uses of St. John's Wort as an external treatment?

<p>Astringent to treat wounds (D)</p> Signup and view all the answers

Which compound in St. John's Wort is linked to photosensitivity?

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

What serious condition can occur when St. John's Wort is used with selective serotonin reuptake inhibitors (SSRIs)?

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

Which of the following is a common side effect of St. John's Wort?

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

What effect does St. John's Wort have on the central nervous system when combined with SSRIs?

<p>Causes muscle spasms (C)</p> Signup and view all the answers

In terms of drug interaction, what role does St. John's Wort play as an inducer?

<p>Inducer of CYP450 (B)</p> Signup and view all the answers

What is a potential gastrointestinal side effect of St. John's Wort?

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

Which of the following symptoms is NOT associated with serotonin syndrome from St. John's Wort?

<p>Reduced body temperature (C)</p> Signup and view all the answers

What part of the plant Boraginaceae is primarily used for medicinal purposes?

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

Which compound is primarily responsible for the red color in the root of Boraginaceae?

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

What is one of the primary uses of alkannin and shikonin?

<p>Natural food colors (A)</p> Signup and view all the answers

Which of the following properties is NOT associated with Boraginaceae?

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

Which condition can Boraginaceae roots help treat?

<p>HIV-1 (D)</p> Signup and view all the answers

Which plant part is used from St. John’s Wort?

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

Which of the following is a known application of the Boraginaceae family in cosmetics?

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

What is a significant role of alkannin and shikonin in medicine?

<p>Anti-tumor activities (B)</p> Signup and view all the answers

What is the effect of using Boraginaceae for external wounds?

<p>Promotes wound healing (B)</p> Signup and view all the answers

Which of the following is NOT a known benefit of Boraginaceae?

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

Which of the following is a common structure found in anthraquinones?

<p>9,10-dioxoanthracene (A)</p> Signup and view all the answers

Anthraquinones can be found in which of the following plant families?

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

Which of the following describes the form in which anthraquinones usually occur in plants?

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

What is the most common structural variation of anthraquinones found in plants?

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

Which type of glycoside is more commonly found in anthraquinones?

<p>O-glycosides (C)</p> Signup and view all the answers

What functional groups are predominantly present in the basic structure of anthraquinones?

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

Which of the following anthraquinones is an example of an O-glycoside?

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

In what kind of chemical structure do anthraquinones generally exist?

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

What is one of the primary roles of anthraquinones in plants?

<p>Act as defense compounds (C)</p> Signup and view all the answers

Which of the following statements is false regarding anthraquinones?

<p>They are exclusively found in monocots. (C)</p> Signup and view all the answers

What is a common side effect of stimulant laxatives?

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

Which condition should stimulant laxatives be avoided in?

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

What can excessive use of stimulant laxatives lead to?

<p>Loss of electrolytes and fluids (A)</p> Signup and view all the answers

In which population is the use of stimulant laxatives particularly cautioned?

<p>Children under 10 (A)</p> Signup and view all the answers

What is a potential metabolic effect of continuous use of stimulant laxatives?

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

What should be done if symptoms such as abdominal pain and rectal bleeding occur after taking stimulant laxatives?

<p>Consult a physician immediately (A)</p> Signup and view all the answers

Which digestive condition is specifically mentioned as a contraindication for stimulant laxatives?

<p>Inflammation of the intestines (C)</p> Signup and view all the answers

What is an important precaution regarding the duration of use for stimulant laxatives?

<p>They should be used for a maximum of 1-2 weeks (B)</p> Signup and view all the answers

What type of laxative is specifically classified as a stimulant laxative?

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

What should be avoided when using stimulant laxatives?

<p>Prolonged use beyond the recommended time (D)</p> Signup and view all the answers

Flashcards

Microsublimation Test

A test used to identify the presence of anthraquinones, a class of organic compounds often found in plants.

Anthraquinone

A specific type of anthraquinone that can be identified using the microsublimation test. Anthraquinones are often present in plants and are used in various applications, such as dyes and pharmaceuticals.

Sublimation

The process of a solid changing directly into a gas, skipping the liquid phase. This occurs when heating anthraquinones during the microsublimation test.

Red Color Reaction with Alkali

A simple chemical reaction that produces a red color when anthraquinones are reacted with an alkali (like sodium hydroxide or potassium hydroxide).

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Borntrager's Test

A test used to detect anthraquinone glycosides, which are anthraquinones combined with sugar molecules.

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Senna Tora

A plant with medicinal properties, specifically its seeds are used for various purposes.

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Fabaceae

A family of flowering plants that includes a wide variety of trees, shrubs, and herbs. It's known for its legume fruits (pods) and its medicinal properties.

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Chrysophanol

A type of anthraquinone present in Senna Tora seeds. It's known for its laxative properties and contributes to the plant's medicinal effects.

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Aloe-emodin

A type of anthraquinone present in Senna Tora seeds. It's characterized by its laxative properties and its presence alongside other anthraquinones in the plant.

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Stimulant Laxative

A type of laxative that stimulates the intestines to help with bowel movements.

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Riththi

A drug that is classified as a stimulant laxative. It promotes bowel movements but can have side effects.

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Abdominal Discomfort

A side effect of Riththi. It can cause discomfort in the stomach.

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Diarrhea and Dehydration

A possible reaction to taking an overdose of Riththi. Can lead to severe diarrhea and loss of fluids.

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Electrolyte Imbalance

A condition that may develop with long-term use of Riththi. It affects the balance of minerals in the body.

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Quinones

A group of important substances found in herbs, often used for external treatments, especially infections.

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Herbal Remedies for Skin Infections

The use of herbs, often for skin infections or external issues.

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External Use of Herbal Remedies

The application of herbal remedies directly to the skin to treat infections.

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Contraindications of Riththi

Medical conditions that prevent the use of Riththi.

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Precautions with Riththi

Important precautions to take when using Riththi. It's crucial to consult a medical professional if discomfort occurs.

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St. John's Wort

A natural remedy often used to treat mild depression, anxiety, and sleep disorders.

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CYP450 Inducer

A substance that increases the activity of certain enzymes (like those involved in drug metabolism) in the liver.

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Selective Serotonin Reuptake Inhibitor (SSRI)

A type of medication that prevents the reabsorption of serotonin in the brain, increasing serotonin levels.

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Serotonin Syndrome

A serious condition that occurs when there are too high levels of serotonin in the body, often resulting from combining certain medications and supplements.

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Hypericin

A type of plant compound with antimicrobial and antiviral properties, found in St. John's Wort.

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Photosensitivity

A condition that makes skin more sensitive to sunlight, often caused by certain medications or herbal supplements like St. John's Wort.

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Neurological and Gastrointestinal Side Effects

A common side effect of St. John's Wort, including dizziness, confusion, tiredness, drowsiness, headache, and digestive issues.

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Herb-Drug Interaction

An interaction that happens when a substance (like St. John's Wort) influences how another substance (like prescribed medication) is processed by the body.

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What is Alkanna?

A plant with red pigments in its root, used for dyeing and cosmetics.

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What is alkannin?

A chemical compound found in Alkanna root, used for dyeing and possesses various medicinal properties.

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What makes Alkanna a useful plant?

This plant's root contains a red substance, which is a naphthoquinone. It's used for dyeing fabrics and as a coloring agent in cosmetics.

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What do Alkanna and Gromwell have in common?

Alkanna and Gromwell share a common characteristic. Describe it.

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How are shikonin and alkannin used?

Shikonin and alkannin are red pigments extracted from Alkanna root. They are commonly used for a specific application.

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Where do we use Alkanna's red pigments?

Alkanna root's red pigments are used for a variety of applications. Name two of them.

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What are the potential benefits of Alkanna root?

Alkanna root offers potential health benefits by possessing specific properties.

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What specific ailments can Alkanna be used to treat?

Alkanna is used in traditional medicine to treat various ailments. Name two of them.

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What are some of the key properties of Alkanna root?

Alkanna is a natural source of various beneficial compounds, but it also contains specific compounds with specific properties.

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Why is Alkanna a significant plant?

Alkanna is a valuable plant with a rich history and is known for its medicinal and cosmetic properties.

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What are Quinones?

A class of organic compounds derived from aromatic compounds like benzene, naphthalene, or anthracene, characterized by a cyclic dione structure. They are often found in nature as benzoquinones, naphthoquinones and anthraquinones.

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What are Anthraquinones?

The most common type of quinone found naturally in plants, derived from anthracene. These compounds often have two keto groups at positions 9 and 10.

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Where are Anthraquinones found in plants?

Plants from the Liliaceae (monocot) and Polygonaceae, Leguminosae (Fabaceae), Rhamnaceae, Rubiaceae, Bignoniaceae (dicot) families often contain anthraquinones.

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What forms can Anthraquinones exist in?

Anthraquinones can be found in two forms: free form or glycoside form. The glycoside form is when the anthraquinone is attached to a sugar molecule.

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Describe the basic structure of Anthraquinone.

Anthraquinone is a cyclic compound with two keto groups at positions 9 and 10, formally derived from anthracene.

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What are some reduced forms of Anthraquinones?

Anthraquinones can be reduced, resulting in different forms such as anthrone, anthranol, oxoanthrone, and dianthrone.

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What are O-glycosides?

A type of glycosidic linkage where the sugar part is directly attached to the oxygen atom of the aglycone, a non-sugar component.

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What are C-glycosides?

A type of glycosidic linkage where the sugar part is directly linked to a carbon atom of the aglycone.

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How are Anthraquinones commonly found in plants?

Anthraquinones are often found in plants as glycosides, where a sugar molecule is attached to the anthraquinone. These glycosides can be either O-glycosides or C-glycosides, with O-glycosides being more common.

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What are Anthraquinones with two hydroxyl groups at positions 1 and 8 called?

Anthraquinone derivatives with two hydroxyl (OH) groups at positions 1 and 8, often found in orange-red colored compounds.

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Study Notes

Quinones

  • Quinones are organic compounds derived from aromatic compounds like benzene, naphthalene, or anthracene.
  • Anthraquinones (AQs) are the most common naturally occurring quinones.
  • AQs are found in both monocots and dicots across various plant families.
  • AQs can exist in free form or as glycosides.

Structure of Anthraquinones

  • The basic structure of anthraquinone is 9,10-dioxoanthracene.
  • It's derived from anthracene and has two keto groups, typically at positions 9 and 10.
  • Anthraquinones often exist in a reduced form, such as anthrone, anthranol, oxanthrone, or dianthrone.
  • AQs frequently occur in plants as glycosides; oxygen-linked glycosides (O-glycosides) are more common than carbon-linked glycosides (C-glycosides).

Classification of Anthraquinones

  • Anthraquinones can be classified into several categories based on their structure and characteristics.
    • Anthraquinones: Found in orange-red compounds, typically hydroxylated at positions 1 and 8. Types include: rhein, aloe-emodin, chrysophanol, emodin, and physcion.
    • Anthrones and Anthranols: Reduced form of anthraquinones. Types include: emodin anthranol, chrysophanol anthranol and chrysophanol. They are isomers and are frequently found in plants.
    • Oxanthrones: Intermediate compounds between anthraquinones and anthrones/anthranols. Types include: Emodin oxanthrones.
    • Aloin-type glycosides: C-glycoside that sugar part linked at C10 of the core structure with a C−C bond. Types include: aloin and chrysaloin.
    • Dianthrones: Derived from two anthrone molecules. Types include: sennidin A, sennidin B, palmidin A, and palmidin B.

Biosynthesis of Anthraquinones

  • Two major pathways are used for anthraquinones biosynthesis:
    • Acetate pathway
    • Shikimate-mevalonate pathway

Tests for Anthraquinones

  • Microsublimation test: Anthraquinone sublimates at 160-180°C, forming needles or droplets, and gives a red color with alkali (ammonium hydroxide or potassium hydroxide).
  • Borntrager's test: The sample is boiled with dilute HCl, then extracted with dichloromethane. Adding ammonium hydroxide to the extract results in a pink to red color, indicating the presence of anthraquinone.
  • Modified Borntrager's test: Used for C-type glycosides, a stronger oxidizing agent is required (e.g., peroxide) to hydrolyze the glycoside.

Pharmaceutical Uses Of Anthraquinones

  • Anthraquinones, especially their aglycone forms in anthrones and anthranols, have stimulant laxative properties due to their effect on colon contractions and water secretion.
  • Anthraquinones also exhibit antimicrobial, antioxidant, and anti-inflammatory activity, among others.
  • Naphthoquinones (e.g., plumbagin) have antimicrobial, antitumor, and anti-inflammatory effects.
  • Some anthraquinones are used in traditional medicine as a topical remedies for skin conditions.

Plant Samples

  • Different plants contain various anthraquinones.
  • Examples include aloe vera, senna, rhubarb, henna, gromwell, alkanna, and St. John's Wort.

St. John's Wort

  • Contains hypericin and pseudohypericin, which are naphthodianthrones.
  • Also contains prenylated phloroglucinols (e.g., hyperforin) and flavonoids.
  • Used as an antidepressant for mild to moderate depression.

Discussion Points

  • The different types of anthraquinone compounds found in various plants.
  • The structural variations in plants contributing to the medicinal properties.
  • The different methods of analysis and extraction of these compounds.
  • The importance of plant identification and standardization in herbal medicine.

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