Sesquiterpenes and Their Applications in Plants
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Questions and Answers

What is the basic carbon skeleton structure of sesquiterpenes?

Sesquiterpenes have a carbon skeleton consisting of 15 carbon atoms.

Identify two main types of sesquiterpenes based on their structure.

Regularly built sesquiterpenes and irregularly built sesquiterpenes.

How many naturally occurring sesquiterpene lactones are of pharmaceutical interest?

Approximately 5000 naturally occurring representatives.

What role does farnesyldiphosphate play in sesquiterpene biosynthesis?

<p>Farnesyldiphosphate acts as a key intermediate in the biosynthesis of sesquiterpenes.</p> Signup and view all the answers

In which families or groups is sesquiterpene distribution primarily found?

<p>Sesquiterpenes are mainly found in the Asteraceae family, liverworts, basidiomycetes, algae, and marine organisms.</p> Signup and view all the answers

What type of compounds are matricin and pseudoguaianolide, and where can they be commonly found?

<p>Matricin and pseudoguaianolide are sesquiterpenes found in chamomile blossoms.</p> Signup and view all the answers

What is the significance of vapor distillation in the extraction of matricin?

<p>Vapor distillation is significant for extracting matricin because it preserves the compound's integrity and volatility.</p> Signup and view all the answers

List two classes of compounds mentioned in the content that are derived from plants.

<p>Two classes of compounds are flavonoids and phenolic carboxylic acids.</p> Signup and view all the answers

What are the structural derivatives referenced along with longipinene?

<p>The structural derivatives referenced include germacranolides and eudesmanolides.</p> Signup and view all the answers

How do 7-O-glycosides and 7-O-malonyl glycosides of apigenin and luteolin contribute to plant properties?

<p>These glycosides contribute to the antioxidant and anti-inflammatory properties of plants.</p> Signup and view all the answers

What is the mechanism by which sesquiterpene lactones inhibit NF-κB?

<p>They inhibit NF-κB through the covalent modification of SH groups by the α-methylene-γ-lactone.</p> Signup and view all the answers

List two types of inflammatory mediators whose expression is inhibited by sesquiterpene lactones.

<p>Cytokines such as IL-1β and TNF-α.</p> Signup and view all the answers

What are the common applications of arnica preparations?

<p>Arnica is used in ointments and tinctures for bruises, rheumatic muscle complaints, and insect bites.</p> Signup and view all the answers

Why should arnica not be administered orally?

<p>Due to possible side effects associated with oral ingestion.</p> Signup and view all the answers

What is the parent plant for Löwenzahn, and what family does it belong to?

<p>The parent plant is Taraxacum officinale L., and it belongs to the Asteraceae family.</p> Signup and view all the answers

What parts of the dandelion plant are used in herbal preparations?

<p>Both the above-ground and below-ground dried plant parts are used.</p> Signup and view all the answers

Identify one component of Taraxaci herba cum radice.

<p>Sesquiterpene lactones such as taraxic acid.</p> Signup and view all the answers

What type of allergy potential does arnica have within the Asteraceae family?

<p>Arnica has a high sensitization potential for contact allergies.</p> Signup and view all the answers

What are the two main types of glucosides found in dandelions?

<p>Taraxic acid glucoside and Taraxcolide glucoside.</p> Signup and view all the answers

What is the primary diuretic effect of dandelion attributed to?

<p>The high content of potassium ions.</p> Signup and view all the answers

What can cause skin eczema in relation to dandelion?

<p>Intensive contact with dandelion sap due to Taraxic acid glucoside.</p> Signup and view all the answers

List two applications of dandelion in herbal medicine.

<p>Production of infusions and as a base for combination preparations for dyspeptic disorders.</p> Signup and view all the answers

Which plant part is primarily used in the formulation of Millefolii herba?

<p>The dried flowering tops of Achillea millefolium.</p> Signup and view all the answers

What compounds are found in Millefolii herba that are significant for its medicinal properties?

<p>Essential oils and sesquiterpene lactones, particularly guaianolides.</p> Signup and view all the answers

What is the minimum concentration of essential oil required for Millefolii herba according to PhEur?

<p>At least 2 ml/kg.</p> Signup and view all the answers

What is one common use of dandelion extracts in herbal medicine?

<p>To aid loss of appetite.</p> Signup and view all the answers

What are the main pharmacological effects of Yarrow (Millefolii herba)?

<p>Yarrow exhibits anti-inflammatory, spasmolytic, antimicrobial, antifungal, and choleretic effects.</p> Signup and view all the answers

How does Yarrow contribute to digestive health?

<p>Yarrow can help with loss of appetite and dyspeptic disorders due to its bitter effect from sesquiterpene lactones.</p> Signup and view all the answers

What is the significance of proazulene in Yarrow?

<p>Proazulene, a sesquiterpene lactone, contributes to the anti-inflammatory properties of Yarrow.</p> Signup and view all the answers

What are the external uses of Yarrow in folk medicine?

<p>Yarrow is used externally for wound healing and treating inflammatory skin diseases.</p> Signup and view all the answers

What is the allergenic potency of Yarrow, and what compounds contribute to it?

<p>Yarrow has medium allergenic potency, potentially caused by compounds such as ⍺-peroxyachifolid.</p> Signup and view all the answers

What is the primary parent plant of Wormwood (Absinthii herba)?

<p>The primary parent plant of Wormwood is Artemisia absinthium L.</p> Signup and view all the answers

Which components in Yarrow contribute to its antimicrobial effects?

<p>Essential oils, sesquiterpene lactones, and polyacetylenes in Yarrow contribute to its antimicrobial effects.</p> Signup and view all the answers

What role does Yarrow play in industrial tea blends?

<p>Yarrow is commonly used in industrial tea blends to promote digestive health.</p> Signup and view all the answers

What are sesquiterpene lactones, and why are they significant in Yarrow?

<p>Sesquiterpene lactones are a type of compound in Yarrow that provide anti-inflammatory and bitter properties.</p> Signup and view all the answers

In what way does Yarrow act as a spasmolytic agent?

<p>Yarrow acts as a spasmolytic agent primarily through its essential oils and flavonoids.</p> Signup and view all the answers

What is the primary role of 5-lipoxygenase in the formation of leukotrienes?

<p>5-lipoxygenase catalyzes the conversion of arachidonic acid into leukotrienes.</p> Signup and view all the answers

How do Petasites extracts affect leukotriene synthesis?

<p>Petasites extracts inhibit the synthesis of leukotrienes, including LTB4 and cysteinyl leukotrienes.</p> Signup and view all the answers

What is the significance of 5-Hydroperoxyeicosatraenoate (5-HPETE) in leukotriene synthesis?

<p>5-HPETE is a precursor in the biosynthesis of leukotrienes from arachidonic acid.</p> Signup and view all the answers

What is one key effect of petasin on intracellular calcium levels?

<p>Petasin inhibits the release of intracellular Ca2+ from mitochondria.</p> Signup and view all the answers

Identify two leukotrienes synthesized from arachidonic acid.

<p>Leukotriene A4 (LTA4) and Leukotriene B4 (LTB4).</p> Signup and view all the answers

What are some active ingredients in Petasites extracts responsible for their effects?

<p>The main active ingredients are petasins.</p> Signup and view all the answers

How does the inhibition of 5-lipoxygenase by petasin affect inflammation?

<p>Inhibition of 5-lipoxygenase reduces leukotriene production, thus lowering inflammation.</p> Signup and view all the answers

What is not well understood regarding the molecular mechanisms of iso- and neopetasins?

<p>The exact mechanisms by which iso- and neopetasins inhibit leukotriene synthesis are unclear.</p> Signup and view all the answers

Flashcards

What are sesquiterpenes?

Sesquiterpenes are a large group of terpenes with 15 carbon atoms, composed of 3 isoprene units. They are common in plants, especially in the Asteraceae family, and also found in other organisms like liverworts, fungi, algae, and marine life.

What makes sesquiterpenes 'irregular'?

Sesquiterpenes are often built with irregularities, where methyl groups move or rings break, making their structure more complex.

What are sesquiterpene lactones?

Sesquiterpene lactones are a special type of sesquiterpene featuring a lactone ring within their structure. They are important in pharmaceuticals due to their diverse biological activities.

What is the key precursor for sesquiterpene biosynthesis?

Farnesyldiphosphate is a key starting molecule for building sesquiterpenes. It can be used directly, or rearranged into nerolidyldiphosphate before further processing.

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How are sesquiterpenes built?

The biosynthesis of sesquiterpenes involves several steps, starting with farnesyldiphosphate, which can either be used directly or be rearranged before being converted into a variety of sesquiterpenes.

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Pseudoguaianolide

A type of sesquiterpene with a guaiane-like structure, found in chamomile, responsible for its blue color when heated.

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Matricin

A compound found in chamomile blossoms that can be converted into a blue compound, azulene, upon heating.

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Vapor Destillation

The process of heating a compound to convert it into a volatile form, often using a specialized apparatus.

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Germacranolide

A type of sesquiterpene with a germacrane-like structure.

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Eudesmanolide

A type of sesquiterpene with a eudesmane-like structure.

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Sesquiterpene lactones

A group of organic compounds with a specific molecular structure, characterized by a 15-carbon skeleton and often exhibiting biological activity.

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10-alpha-methyl-pseudoguaianolide

A type of sesquiterpene lactone with a specific structural feature: a methyl group attached to carbon 10 and a 1,2-dimethylcyclopentane ring system.

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Transcription factor

A protein that regulates the expression of genes involved in the immune response, often triggered by inflammation.

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NF-κB (Nuclear Factor kappa-B)

A specific transcription factor involved in activating genes that trigger inflammation, playing a key role in immune responses.

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NF-AT (Nuclear Factor of Activated T-cells)

Another important transcription factor involved in regulating immune responses and inflammation.

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Inhibition

The biological effect of slowing down a reaction or process, often used to describe the reduction of inflammation or cell signaling.

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Covalent modification

A chemical reaction where a molecule binds to a functional group of another molecule, forming a new compound.

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Alpha-methylene-gamma-lactone

A reactive chemical group found in some sesquiterpene lactones, capable of forming covalent bonds with thiol groups (SH) in proteins.

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Taraxacolide Glucoside

A type of sesquiterpene lactone found in dandelion.

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Taraxic Acid Glucoside

A type of sesquiterpene lactone found in dandelion. It is a contact allergen, causing skin eczema with intensive contact.

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Inulin

A natural, sweet-tasting carbohydrate found in dandelion, especially in the spring. It is a storage form of energy for the plant.

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Taraxaci herba cum radice

A herb used in herbal medicine, derived from the dandelion plant (Taraxacum officinale). It is used to treat indigestion, urinary problems, and mild biliary disorders.

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Millefolii herba

A herb used in herbal medicine, derived from the common yarrow plant (Achillea millefolium). It is known for its anti-inflammatory and wound-healing properties.

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Essential Oil from Yarrow

A volatile compound extracted from yarrow (Achillea millefolium) containing a mixture of compounds, primarily terpenes. It gives the plant its characteristic aroma.

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Guaianolides

A specific type of sesquiterpene lactone found in yarrow (Achillea millefolium). Proazulene is a precursor to azulene, a compound with anti-inflammatory properties.

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Petasites Extracts

A group of plant-derived compounds with anti-inflammatory and spasmolytic effects, known for inhibiting leukotriene synthesis.

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Petasin

A naturally occurring compound found in Petasites extracts, known for inhibiting the production of leukotrienes.

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Leukotriene B4 (LTB4)

A potent inflammatory mediator produced in the body, involved in allergic reactions and inflammation.

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Cysteinyl Leukotrienes (LTC4, LTD4, LTE4)

A family of inflammatory mediators that play a role in allergic responses and inflammation.

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Platelet Activating Factor (PAF)

A substance that triggers the release of calcium from cellular compartments, leading to the activation of 5-lipoxygenase (5-LO).

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5-Lipoxygenase (5-LO)

An enzyme responsible for the production of leukotrienes from arachidonic acid.

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Release of intracellular Ca2+

A process where intracellular calcium is released from mitochondria, necessary to activate 5-lipoxygenase (5-LO) in leukocytes.

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Mechanism of LT Inhibition by Petasins

The molecular mechanisms by which petasins inhibit the synthesis of leukotrienes are not fully understood.

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What is an analog?

A compound that is similar in structure and properties to a compound called the parent compound. It usually has the same skeleton but one or more substituents have been altered in a way that affects the properties of the molecule.

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What is vapor distillation?

The process of extracting volatile compounds from a plant material by heating it with steam, allowing the steam to carry the compounds away, followed by condensation of the steam and separation of the desired compound from the water.

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What is Proazulene?

A natural compound found in plants, specifically in chamomile blossoms, that has a blue color. It's used for its anti-inflammatory and anti-spasmodic properties in medicine.

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What is 'Arzneidrogen'?

Plants that are considered a source of medicine and are used to extract active compounds for medicinal purposes.

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What is ⍺-peroxyachifolid?

The active compound found in yarrow plant, known for its role in causing allergic reactions of the delayed type.

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What is Yarrow (Millefolii herba)?

A plant used in herbal remedies, traditionally used for its anti-inflammatory and digestive health benefits, sometimes used for wound healing. It contains a diverse set of compounds including essential oils and sesquiterpene lactones.

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What is Wormwood (Absinthii herba)?

A plant used in herbal remedies, traditionally used for its anti-inflammatory and digestive health benefits, sometimes used for wound healing. It contains a diverse set of compounds including essential oils and sesquiterpene lactones.

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How does yarrow have spasmolytic effects?

The essential oil, flavonoids, and sesquiterpene lactones in yarrow contribute to its anti-spasmodic action, helping to relax muscles in the digestive tract, reducing discomfort.

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How does yarrow have anti-inflammatory effects?

Yarrow, containing sesquiterpene lactones and proazulene, contributes to its anti-inflammatory properties, helping to reduce inflammation in the body.

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Study Notes

Isoprenoids - Terpenes and Terpenoids

  • Isoprenoids are classified by the number of carbon atoms.
  • Sesquiterpenes are a C15 unit (C10 + C5).

Sesquiterpenes

  • Sesquiterpenes have a carbon skeleton of 15 carbons, broken down into 3 isoprene units.
  • Many sesquiterpenes have irregular structures due to methyl migration or ring cleavage.
  • Sesquiterpenes form the largest group of terpenes (>12,000 representatives).
  • Sesquiterpene lactones are of pharmaceutical interest (~5000 naturally occurring).
  • They are practically ubiquitous in the Asteraceae family.
  • They are also found in other organisms like liverworts, basidiomycetes, algae, and marine organisms.

Biosynthesis of Sesquiterpenes

  • Farnesyldiphosphate (FPP) is a key intermediate, either directly or after rearrangement to nerolidyldiphosphate.
  • Conversion to cyclic terpenes occurs via cationic intermediate stages.

Sesquiterpene Lactones

  • The characteristic feature of sesquiterpene lactones is a γ-lactone ring.
  • An important subgroup has a reactive methylene group at the α-position of the lactone ring carbonyl group, allowing for 1,4-addition.
  • Additional reactive structural elements like α,β-unsaturated carbonyls or epoxides may be present.
  • Common in Asteraceae (over 200 species).
  • They are biologically active compounds, with a bitter or pungent taste and potential for local skin irritation, allergic reactions, and relatively high toxicity upon systemic administration.

Sesquiterpene-containing Raw Materials

  • Raw materials and pure substances containing sesquiterpenes and therapeutically used substances are detailed with examples (e.g. different types containing Eudesmane, Pseudoguaianolide, etc.).
  • This includes specific plant types like Arnica flowers (Anicae flos, Arnikablüten), Dandelion root and herb (Taraxaci herba cum radice, Löwenzahn), Yarrow (Millefolii herba, Schafgarbenkraut) and Wormwood (Absinthii herba, Wermutkraut).
  • Each of these plant-derived substances contains specific sesquiterpenes and other compounds (essential oils, flavonoids, etc.).
  • Applications: The uses and effects of these plant based substances are described.

Extraction with Supercritical Gases (SFE)

  • Supercritical Fluid Extraction (SFE) uses supercritical CO2, especially for extracting thermolabile substances.
  • CO2 is readily available, inexpensive, and non-toxic.
  • This method allows for selective extraction of lipophilic compounds (adjusting gas density) and can be combined with entrainers (additives) to increase polarity, but not excessively as that could reduce selectivity.
  • SFE is used industrially to decaffeinate coffee, remove flavourings, and produce extracts.

Petasites Rhizome and Folium

  • Petasites extracts have anti-inflammatory and spasmolytic effects.
  • The active ingredients are petasins, specifically inhibiting leukotriene synthesis.

Artemisinin

  • Artemisinin is a cadinan-type sesquiterpene from Artemisia annua L.
  • It is an effective antimalarial agent, active in nM concentrations.
  • Its therapeutic use involves selective uptake by infected erythrocytes.

Other Important points:

  • Sesquiterpenes are valuable for various types of medicine and industrial applications.
  • Their biological properties and practical applications are influenced by their chemical structures, particularly their presence in specific types and amounts in individual plants.

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2.3 Sesquiterpenes PDF

Description

This quiz explores the structure, types, and significance of sesquiterpenes, including their biosynthesis and pharmaceutical applications. Participants will learn about key compounds derived from plants and the mechanisms by which sesquiterpene lactones exert their effects. Test your knowledge on these fascinating natural products and their roles in botany and medicine.

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