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Questions and Answers
Considering the biosynthetic origin of terpenoids, which statement best explains their structural diversity?
Considering the biosynthetic origin of terpenoids, which statement best explains their structural diversity?
- The cyclization and rearrangement of a limited set of isoprenoid precursors generate a wide array of terpenoid structures. (correct)
- Random mutations in isoprenoid synthase genes result in unpredictable structural variations in terpenoids.
- Terpenoids are derived from a variety of non-isoprenoid precursors, leading to diverse structures.
- Enzymatic reactions introduce a limited number of modifications to a vast array of isoprenoid precursors.
How does the shared biosynthetic origin of terpenoids influence their classification and study?
How does the shared biosynthetic origin of terpenoids influence their classification and study?
- It necessitates classification based on bioactivity rather than structure due to the variability in modifications.
- It complicates classification due to convergent evolution, leading to structural similarities across different classes.
- It hinders comparative studies due to the inability to trace evolutionary relationships between different terpenoids.
- It allows for a systematic classification based on the number of isoprene units and subsequent modifications. (correct)
If a newly discovered natural product is suspected to be a terpenoid, what experimental evidence would most strongly support this hypothesis?
If a newly discovered natural product is suspected to be a terpenoid, what experimental evidence would most strongly support this hypothesis?
- Isolation of the compound from a plant source known to produce essential oils.
- Observation of antimicrobial activity against a broad spectrum of bacteria and fungi.
- Detection of significant UV absorption, indicating the presence of conjugated double bonds.
- Characterization of its fragmentation pattern by mass spectrometry, revealing repeating isoprene units. (correct)
Considering the role of enzymes in terpenoid biosynthesis, what is the most likely outcome of a mutation that alters the active site of a terpene synthase?
Considering the role of enzymes in terpenoid biosynthesis, what is the most likely outcome of a mutation that alters the active site of a terpene synthase?
How does the principle of 'repeated carbon units' in terpenoid biosynthesis relate to the concept of modularity in natural product synthesis?
How does the principle of 'repeated carbon units' in terpenoid biosynthesis relate to the concept of modularity in natural product synthesis?
While terpenoids are known for their widespread presence in higher green plants, what crucial enzymatic process fundamentally enables their biosynthesis?
While terpenoids are known for their widespread presence in higher green plants, what crucial enzymatic process fundamentally enables their biosynthesis?
What characteristic of terpenoids primarily dictates their diverse range of functions within plants, from defense mechanisms to hormonal regulation?
What characteristic of terpenoids primarily dictates their diverse range of functions within plants, from defense mechanisms to hormonal regulation?
Given the complexity of plant metabolism, what challenge do researchers face when attempting to isolate and identify specific terpenoids from plant extracts?
Given the complexity of plant metabolism, what challenge do researchers face when attempting to isolate and identify specific terpenoids from plant extracts?
How might the principles of metabolic engineering be applied to enhance the production of a specific, high-value terpenoid in a plant species?
How might the principles of metabolic engineering be applied to enhance the production of a specific, high-value terpenoid in a plant species?
If a plant species normally produces a particular monoterpene in low quantities, how can elicitation be used to enhance its production as a defense mechanism?
If a plant species normally produces a particular monoterpene in low quantities, how can elicitation be used to enhance its production as a defense mechanism?
Flashcards
What are terpenoids?
What are terpenoids?
Naturally occurring organic compounds found widely in nature.
Terpenoid biosynthesis?
Terpenoid biosynthesis?
Most green plants can create these compounds through biosynthesis.
Terpenoids origin
Terpenoids origin
Organic compounds created by most plants.
Terpenoids
Terpenoids
Compounds formed from repeating carbon units.
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Building blocks of terpenoids
Building blocks of terpenoids
Repeated carbon units.
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Biosynthetic origin
Biosynthetic origin
Terpenoids are made through the same biochemical process.
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Repeated units formation
Repeated units formation
Combination of smaller units to form larger molecules.
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- Terpenoids are naturally occurring organic compounds.
- They are the most widely distributed natural compounds.
- They are biosynthesized by almost all higher green plants.
- Lower plants like bacteria and fungi produce interesting terpenoids.
- Marine organisms produce some abnormal terpenoid compounds.
- In the animal kingdom, they are detected in defense secretion of some insects and are termed "insect pheromones."
- About 50,000 terpenoid compounds have been detected and isolated; their chemical structures have been elucidated.
- This surpasses the number of any other naturally occurring compounds.
- Terpenoids are of common biosynthetic origin, forming from repeated carbon units.
- Each unit has 5 carbon atoms.
- These units are branched chain.
- They are also unsaturated.
- The units are termed isoprene units; isoprenoid is sometimes used to designate these compounds.
- Terpenoids have chemically diverse and numerous structures, starting from simple C5 units and multiplying to form higher terpenoid compounds.
- Hemiterpenoids contain C5.
- Monoterpenoids contain C10.
- Tetraterpenoids contain C40.
- Polyterpenoids contain nC5.
- Varying the type, number, and position of functional groups can create a huge number of compounds.
- The most important structural feature of terpenoids is their derivation from monomeric structural units called isoprene units.
- This was first reported by O. Wallach in 1887.
- This was later confirmed experimentally through chemical analysis of thermal decomposition products.
- Terpenoid compounds range in molecular weight, from low (volatile oils), to medium (steroids), to high (rubber).
- Terpenoids consist of a number of 5-carbon units derived from 2 methyl-butadiene.
- In 1925, Prof Ignold determined isoprene units are linked together in a systematic fashion known as Head to Tail linkage.
- Prof Ruzicka crowned it the "isoprene Rule" in 1953, stating that terpenoids are formed from multiple isoprene units according to head to tail linkage.
- Some compounds of terpenoid origin do not obey the isoprene rule: Artemisiaketone and 2-cholesterol are always exceptions.
General vs Exceptional Modes
- Terpenoid formation from isoprene units follows 2 modes
- Terpenoid formation can follow a general mode
- Terpenoid formation can follow an exceptional mode.
- The general mode is known as linear combination mode.
- In this mode isoprene units condensed together in head to tail fashion forming straight chains.
- With exceptional modes, terpenoid compounds form from linear combination compounds via chemical or mechanical modification, e.g., rearrangement, cleavage, cyclization, degradation, and dimerization and polymerization.
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