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Questions and Answers
Plant ______ are extensively used for their aromatic qualities.
Plant ______ are extensively used for their aromatic qualities.
terpenoids
Isoprene is recognized as the basic constituent of ______.
Isoprene is recognized as the basic constituent of ______.
terpenes
The ______ rule hypothesizes a universal isoprene precursor.
The ______ rule hypothesizes a universal isoprene precursor.
biogenic isoprene
Acetyl CoA is the precursor for ______ biosynthesis.
Acetyl CoA is the precursor for ______ biosynthesis.
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Isopentenyl pyrophosphate is identified as the precursor to all ______.
Isopentenyl pyrophosphate is identified as the precursor to all ______.
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The molecular formula of isoprene is ______.
The molecular formula of isoprene is ______.
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Terpenes may be linked together 'head to ______' to form linear chains.
Terpenes may be linked together 'head to ______' to form linear chains.
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The basic molecular formulas of terpenes are multiples of (C5H8)______.
The basic molecular formulas of terpenes are multiples of (C5H8)______.
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Sesterterpenes are terpenes having 25 carbons and five ______ units.
Sesterterpenes are terpenes having 25 carbons and five ______ units.
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The molecular formula of triterpenes consists of C______H48.
The molecular formula of triterpenes consists of C______H48.
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The linear triterpene squalene is derived from the coupling of two molecules of ______ pyrophosphate.
The linear triterpene squalene is derived from the coupling of two molecules of ______ pyrophosphate.
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Tetraterpenes contain eight isoprene units and have the molecular formula C______H56.
Tetraterpenes contain eight isoprene units and have the molecular formula C______H56.
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Monoterpenes consist of two isoprene units and have the molecular formula C______H16.
Monoterpenes consist of two isoprene units and have the molecular formula C______H16.
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The prototypical acyclic monoterpenoid formed through hydrolysis is ______.
The prototypical acyclic monoterpenoid formed through hydrolysis is ______.
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The most common ring size in monoterpenes is a ______-membered ring.
The most common ring size in monoterpenes is a ______-membered ring.
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Monoterpenes may be ______ or contain rings.
Monoterpenes may be ______ or contain rings.
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Acetyl CoA is the precursor leading to isopentenyl pyrophosphate (IPP), which is the universal precursor for all ______ synthesis.
Acetyl CoA is the precursor leading to isopentenyl pyrophosphate (IPP), which is the universal precursor for all ______ synthesis.
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The initial steps of the pathway involve three molecules of acetyl-CoA fused to produce ______, known as HMG-CoA.
The initial steps of the pathway involve three molecules of acetyl-CoA fused to produce ______, known as HMG-CoA.
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HMG-CoA is reduced by HMG-CoA reductase, which is the rate-limiting reaction in ______ biosynthesis.
HMG-CoA is reduced by HMG-CoA reductase, which is the rate-limiting reaction in ______ biosynthesis.
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Mevalonate is phosphorylated by mevalonate kinase and ______, a distinct soluble enzyme.
Mevalonate is phosphorylated by mevalonate kinase and ______, a distinct soluble enzyme.
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GPP derivatives are associated with ______, a type of terpene.
GPP derivatives are associated with ______, a type of terpene.
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FPP derivatives can form sesquiterpenes, leading to ______ and steroids.
FPP derivatives can form sesquiterpenes, leading to ______ and steroids.
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Diterpenes consist of four isoprene units and have the molecular formula ______.
Diterpenes consist of four isoprene units and have the molecular formula ______.
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Isoprene itself is considered the only hemiterpene, while prenol and isovaleric acid are examples of ______.
Isoprene itself is considered the only hemiterpene, while prenol and isovaleric acid are examples of ______.
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A common six-membered ring system found in ginger oil is called ______.
A common six-membered ring system found in ginger oil is called ______.
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Caryophyllene is a classic bicyclic sesquiterpene obtained from the oil of ______.
Caryophyllene is a classic bicyclic sesquiterpene obtained from the oil of ______.
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One example of a tricyclic compound is ______.
One example of a tricyclic compound is ______.
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Diterpenoids are often encountered in the resins of ______.
Diterpenoids are often encountered in the resins of ______.
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The most common diterpene, which is an acyclic alcohol side chain of chlorophyll, is ______.
The most common diterpene, which is an acyclic alcohol side chain of chlorophyll, is ______.
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More than ______ different diterpenoid structures have been defined.
More than ______ different diterpenoid structures have been defined.
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Squalene is known as the simplest triterpenoid in its ______ form.
Squalene is known as the simplest triterpenoid in its ______ form.
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Cyclizations of monoterpenes and sesquiterpenes lead to macrocyclic diterpenes like ______.
Cyclizations of monoterpenes and sesquiterpenes lead to macrocyclic diterpenes like ______.
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The common example of a sapogenin is ______.
The common example of a sapogenin is ______.
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Saponins can hemolyze red blood cells and are known to kill small animals such as ______.
Saponins can hemolyze red blood cells and are known to kill small animals such as ______.
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Derris elliptica is traditionally used for poisoning ______.
Derris elliptica is traditionally used for poisoning ______.
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Bile acids are synthesized in the ______.
Bile acids are synthesized in the ______.
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Saponins can give a thick ______ when mixed with water.
Saponins can give a thick ______ when mixed with water.
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The most abundant bile acids in human bile are chenodeoxycholic acid and ______.
The most abundant bile acids in human bile are chenodeoxycholic acid and ______.
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Saponins contribute to various properties in herbal medicine and are distributed in over ______ plant families.
Saponins contribute to various properties in herbal medicine and are distributed in over ______ plant families.
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Sapogenins are oxygenated C27 ______ with an hydroxyl group in C-3.
Sapogenins are oxygenated C27 ______ with an hydroxyl group in C-3.
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Bile acids are carried from the liver to the ______, where they are stored for future use.
Bile acids are carried from the liver to the ______, where they are stored for future use.
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The synthesis of bile acids is one of the predominant mechanisms for the excretion of excess ______.
The synthesis of bile acids is one of the predominant mechanisms for the excretion of excess ______.
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Within the intestines, primary bile acids are acted upon by bacteria and converted to secondary bile acids like ______.
Within the intestines, primary bile acids are acted upon by bacteria and converted to secondary bile acids like ______.
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The rate limiting step in bile acid synthesis is catalyzed by the ______.
The rate limiting step in bile acid synthesis is catalyzed by the ______.
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Bile acids are ______ by the intestines and delivered back to the liver via the portal circulation.
Bile acids are ______ by the intestines and delivered back to the liver via the portal circulation.
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The carboxyl group of bile acids is conjugated via an amide bond to either glycine or ______.
The carboxyl group of bile acids is conjugated via an amide bond to either glycine or ______.
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These conjugation reactions yield ______ and tauroconjugates, respectively.
These conjugation reactions yield ______ and tauroconjugates, respectively.
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The ultimate fate of bile acids is secretion into the ______, where they aid in the emulsification of dietary lipids.
The ultimate fate of bile acids is secretion into the ______, where they aid in the emulsification of dietary lipids.
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Study Notes
Terrestrial Natural Product Chemistry - Mevalonate Pathways: Terpenes and Steroids
- Terpenes are a diverse class of hydrocarbons predominantly produced by plants, especially conifers.
- They are the primary components of resin and turpentine derived from resin.
- Turpentine is a mixture of isomeric terpene hydrocarbons, obtained by distilling pine gum.
- Turpentine oil is used topically for joint, muscle, nerve pain, and headaches. It's also inhaled to alleviate chest congestion associated with lung diseases.
- In food and beverages, distilled turpentine oil is utilized as a flavoring agent.
- Terpenoids are chemically modified forms of terpenes, often resulting from oxidation or rearrangement of the carbon skeleton.
Terpenes and Steroids
- Terpenes and terpenoids are the primary constituents of essential oils in plants and flowers.
- Essential oils are commonly used as flavor additives in food, perfumes, aromatherapy, and traditional/alternative medicines.
- Synthetic variations of natural terpenes and terpenoids greatly expand the range of aromas in perfumery and food additives.
Essential Oil Composition
- The composition of essential oils varies based on the plant source.
- Common examples of terpenes and terpenoids include p-cymene (thyme and cumin), (-)-citronellol (rose and geranium), thymol (thyme), farnesol (citronella and lemon grass), menthol (peppermint), and camphor.
- Phenolics like cinnamaldehyde (cinnamon), eugenol (cloves, nutmeg, bay leaf, and basil) are also components of essential oils.
- Essential oils exhibit a wide array of properties and functions, including antibacterial and analgesic effects, contributing to scents, and acting as natural insecticides.
Spearmint's Essential Oil and Rosemary Essential Oil
- Spearmint's essential oil has a cooling effect on nerves and muscles, and is used topically to treat muscular pain, headaches, migraines, and as an antibacterial agent for wound healing.
- Rosemary essential oil enhances memory, improves mood, reduces mild depression, increases alertness, soothes digestion, relieves muscle aches and pain, acts as an anti-itch agent, insecticide, anti-inflammatory, antioxidant, antiseptic, antibacterial, and anti-fungal.
Spearmint Essential Oil Composition
- Key compounds in spearmint essential oil include carvone (81.4%), limonene (4.78%), cis-dihydrocarvone (2.3%), trans-dihydrocarvyl acetate (1.93%), menthone (0.99%), β-bourbonene (0.34%), octanol-3 (0.11%), and others.
Isoprenoids
- Isoprenoids are widespread in all living organisms, comprising a large class of natural products.
- Isoprene, a 5-carbon compound (2-methyl-1,3-butadiene), forms the structural basis for terpenes.
- Ruzicka’s "biogenic isoprene rule" stipulates isoprene as a universal precursor for isoprenoid synthesis.
- Bloch and Lynen’s discoveries elucidated the mevalonate pathway, a key biosynthetic pathway for isoprenoids, including the biosynthesis of steroid hormones.
- Key intermediates in this pathway are isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP).
Mevalonate Pathway
- The mevalonate pathway synthesizes IPP and DMAPP, vital precursors for a broad array of isoprenoids, including terpenes, steroids and more.
- Acetyl-CoA is a key input precursor of the mevalonate pathway
- The mevalonate pathway generates a plethora of terpenoid and steroid structures.
- Key enzymes in this pathway include HMG-CoA Synthase and HMG-CoA Reductase.
Isoprenoids Classification
- Hemiterpenes: Consisting of a single isoprene unit.
- Monoterpenes: Two isoprene units (C10H16).
- Sesquiterpenes: Three isoprene units (C15H24).
- Diterpenes: Four isoprene units (C20H32).
- Sesterterpenes: Five isoprene units (C25H40).
- Triterpenes: Six isoprene units (C30H48).
- Tetraterpenes: Eight isoprene units (C40H56).
- Polyterpenes: Multiple isoprene units.
Terpenoids and Steroids - Additional Information
- Plant terpenoids are extensively used in traditional herbal remedies and are under investigation for various pharmaceutical uses
- Terpenoids provide the aromas of eucalyptus, cinnamon, cloves, and ginger. Several well-known compounds include citral, menthol, camphor
- Plant terpenoids play a significant role in herbal remedies and many diverse medicinal applications are being researched.
Cardiac Glycosides, Bufadienoids, and Cardenolides
- Cardiac glycosides are steroids that exert a strong effect on the cardiac system.
- Cardenolides and bufadienoids are two major groups of cardiac glycosides, distinguished by the types of rings they possess.
Saponins, Sapogenins, and Bile Acids
- Saponins are steroids or triterpenoids with various properties, including the ability to create thick foam and hemolyse red blood cells.
- Sapogenins form the aglycon component of saponins.
- Bile acids are the end products of cholesterol metabolism in mammals, typically containing a carboxyl group at C-24 and hydroxyl groups on the steroid nucleus.
Additional Information - Bile Acids
- Bile acids have crucial functions in the emulsification of dietary lipids in the intestines, are synthesized in the liver, and stored in the gallbladder.
- Bile acids are reabsorbed by the intestines and return to the liver for reuse.
- These acids, often conjugated with glycine or taurine, are further modified to yield glycoconjugates or tauroconjugates, respectively.
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Description
Test your knowledge on terpenes and isoprene biosynthesis with this comprehensive quiz. Explore concepts such as molecular formulas, biosynthetic precursors, and the structural characteristics of terpenes. Perfect for students studying plant biochemistry or organic chemistry.
