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?

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

In which families or groups is sesquiterpene distribution primarily found?

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

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

Matricin and pseudoguaianolide are sesquiterpenes found in chamomile blossoms. Signup and view all the answers

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

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

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

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

What are the structural derivatives referenced along with longipinene?

The structural derivatives referenced include germacranolides and eudesmanolides. Signup and view all the answers

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

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

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

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

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

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

What are the common applications of arnica preparations?

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

Why should arnica not be administered orally?

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

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

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

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

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

Identify one component of Taraxaci herba cum radice.

Sesquiterpene lactones such as taraxic acid. Signup and view all the answers

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

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

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

Taraxic acid glucoside and Taraxcolide glucoside. Signup and view all the answers

What is the primary diuretic effect of dandelion attributed to?

The high content of potassium ions. Signup and view all the answers

What can cause skin eczema in relation to dandelion?

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

List two applications of dandelion in herbal medicine.

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

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

The dried flowering tops of Achillea millefolium. Signup and view all the answers

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

Essential oils and sesquiterpene lactones, particularly guaianolides. Signup and view all the answers

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

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

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

To aid loss of appetite. Signup and view all the answers

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

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

How does Yarrow contribute to digestive health?

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

What is the significance of proazulene in Yarrow?

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

What are the external uses of Yarrow in folk medicine?

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

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

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

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

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

Which components in Yarrow contribute to its antimicrobial effects?

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

What role does Yarrow play in industrial tea blends?

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

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

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

In what way does Yarrow act as a spasmolytic agent?

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

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

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

How do Petasites extracts affect leukotriene synthesis?

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

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

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

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

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

Identify two leukotrienes synthesized from arachidonic acid.

Leukotriene A4 (LTA4) and Leukotriene B4 (LTB4). Signup and view all the answers

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

The main active ingredients are petasins. Signup and view all the answers

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

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

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

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

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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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.