Natural Products from Mevalonate Pathway

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Questions and Answers

What are the two primary pathways for the biosynthesis of IPP?

Mevalonic acid and 1-deoxy-D-xylulose 5-phosphate (correct)

Mevalonic acid and glucose-6-phosphate

Mevalonic acid and D-fructose

2-Amino acids and 1-deoxy-D-xylulose 5-phosphate

Which property is characteristic of monoterpenoids?

They are typically solid at room temperature.

They are non-volatile and colorless.

They are volatile and have intensely pungent odors. (correct)

They have low odor intensity.

Which of the following is a representative example of a monoterpenoid?

β-caryophyllene

Parthenolide

Artemisinin

Menthol (correct)

Which sesquiterpenoid is traditionally used to treat malaria?

Artemisinin (D) Signup and view all the answers

What is the chemical formula of sesquiterpenoids?

C15H24 (D) Signup and view all the answers

Which class of terpenoids can be classified based on their carbocyclic skeleton?

Sesquiterpenoids (D) Signup and view all the answers

What type of product is Cineole known for?

Eucalyptus oil supporter (A) Signup and view all the answers

What is a common use of menthol?

To provide relief from bronchitis and nasal congestion. (B) Signup and view all the answers

What is the main difference between terpenes and terpenoids?

Terpenoids contain oxygen, whereas terpenes do not. (A) Signup and view all the answers

Which of the following is true about isoprene units in terpenoid formation?

Isoprene units follow the isoprene rule in their linkage. (B) Signup and view all the answers

What molecular formula represents a monoterpenoid?

C10H16 (A) Signup and view all the answers

How are terpenoids classified based on the number of carbon atoms?

They are categorized by the number of isoprene units. (B) Signup and view all the answers

What is the function of isopentenyl pyrophosphate (IPP) in the biosynthesis of terpenoids?

It serves as an important intermediate in the synthesis. (A) Signup and view all the answers

Which category of terpenoids contains more than 500 carbon atoms?

Polyterpenoids (C) Signup and view all the answers

What type of terpenoid contains exactly four isoprene units?

Diterpenoids (A) Signup and view all the answers

In terpenoid nomenclature, what is the challenge with systematic names?

They tend to be overly lengthy and complex. (D) Signup and view all the answers

What are triterpenoids primarily known for?

Being components of resins and latex in plants (B) Signup and view all the answers

Which of the following is a type of triterpenoid saponin?

Dioscin (B) Signup and view all the answers

What primary color trait do tetraterpenoids/carotenoids provide in organisms?

Yellow, orange, red, and purple colors (B) Signup and view all the answers

Which compound is known to function as a source of vitamin A?

Beta-Carotene (A) Signup and view all the answers

What role do carotenoids play in animals?

As photoprotective and cancer prevention agents (B) Signup and view all the answers

What is the major form of vitamin A?

Retinol (B) Signup and view all the answers

Which function is associated with tetraterpenoids/carotenoids in plants?

Photosynthetic accessory pigments (C) Signup and view all the answers

Which of the following foods is a common source of vitamin A?

Animal organs (C) Signup and view all the answers

What is the primary medicinal application of Forskolin derived from Coleus forskohlii?

Management of bronchial asthma (D) Signup and view all the answers

Which group of triterpenoids is characterized by a steroid carbon skeleton?

Tetracyclic triterpenoids (B) Signup and view all the answers

Which of the following compounds is not a type of diterpenoid?

Forskolin (D) Signup and view all the answers

What distinguishes pentacyclic triterpenoids from tetracyclic triterpenoids?

Number of rings in the carbon skeleton (D) Signup and view all the answers

What is the mechanism of action of Ginkgolides derived from Ginkgo biloba?

Inhibition of platelet-activating factor (PAF) (C) Signup and view all the answers

Study Notes

Natural Products from Mevalonate & Deoxyxylulose Phosphate Pathway (Terpenoids)

Terpenoids are a group of compounds, mainly found in plants, that includes hydrocarbons known as terpenes and oxygen-containing compounds.
Essential oils are primarily composed of terpenoids.
Terpenoids are built from two or more five-carbon units called isoprene units.
Isoprene is 2-methyl-1,3-butadiene (C₅H₈).
Isoprene units are typically linked in a head-to-tail fashion (isoprene rule).
The number of isoprene units is a basis for classifying terpenoids.

Classification of Terpenoids

Monoterpenoids (C₁₀H₁₆):
- Characterized by their volatility and pungent odors.
- Essential for fragrances and flavors.
- Examples: limonene, menthol, and camphor.
Sesquiterpenoids (C₁₅H₂₄):
- The largest class of terpenoids.
- Examples: β-cadinene and β-caryophyllene.
- Includes sesquiterpenoid lactones, characterized by a specific ring structure.
- Further classified into types like germacranolides, eudesmanolides, and guaianolides based on their ring structures.
- Examples: artemisinin (used in malaria treatment) and parthenolide.
Diterpenoids (C₂₀H₃₂):
- Non-volatile and often found in plants, fungi, and insects.
- Examples: forskolin, ginkgolide, and taxol.
Triterpenoids (C₃₀H₄₈):
- Can be classified into tetracyclic (steroid skeleton) and pentacyclic subgroups.
- Examples: lanosterol, lupeol, and β-amyrin.
- Many triterpenoids combine with sugars to form saponins, which are often components of plant resins, latex, or cuticles.
Tetraterpenoids/Carotenoids (C₄₀H₆₄):
- Responsible for yellow, orange, red, and purple colors in living organisms.
- Act as photoprotective agents, photosynthetic accessory pigments, and membrane stabilizers in plants and microorganisms.
- Crucial as a source of vitamin A and for photoprotection and cancer prevention in animals.
- Examples: vitamin A and β-carotene.

Biosynthesis of Terpenoids

Terpenoids are synthesized using isopentenyl pyrophosphate (IPP) as a key intermediate.
IPP is derived from two metabolic pathways: the mevalonic acid (MVA) pathway and the 1-deoxy-D-xylulose 5-phosphate (DOXP) pathway.

Terpenoids in Pharmacy

Many terpenoids are crucial components in various pharmaceutical applications, including fragrance, flavoring agents and treatments like camphor, cineole and menthol for topical applications and remedies, and artemisinin and parthenolide are used to treat malaria and other conditions.
Pharmaceutical applications utilizing terpenoids come from a diverse range of plants and are part of the chemical compounds extracted from those plants.

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Description

Explore the fascinating world of terpenoids, including their structure, classification, and significance in nature. Learn about the isoprene rule and the different categories of terpenoids such as monoterpenoids and sesquiterpenoids. This quiz delves into essential oils and their composition, providing insight into their unique properties.