Terpenes and Isoprene Quiz
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Questions and Answers

Plant ______ are extensively used for their aromatic qualities.

terpenoids

Isoprene is recognized as the basic constituent of ______.

terpenes

The ______ rule hypothesizes a universal isoprene precursor.

biogenic isoprene

Acetyl CoA is the precursor for ______ biosynthesis.

<p>steroid</p> Signup and view all the answers

Isopentenyl pyrophosphate is identified as the precursor to all ______.

<p>isoprenoids</p> Signup and view all the answers

The molecular formula of isoprene is ______.

<p>C5H8</p> Signup and view all the answers

Terpenes may be linked together 'head to ______' to form linear chains.

<p>tail</p> Signup and view all the answers

The basic molecular formulas of terpenes are multiples of (C5H8)______.

<p>n</p> Signup and view all the answers

Sesterterpenes are terpenes having 25 carbons and five ______ units.

<p>isoprene</p> Signup and view all the answers

The molecular formula of triterpenes consists of C______H48.

<p>30</p> Signup and view all the answers

The linear triterpene squalene is derived from the coupling of two molecules of ______ pyrophosphate.

<p>farnesyl</p> Signup and view all the answers

Tetraterpenes contain eight isoprene units and have the molecular formula C______H56.

<p>40</p> Signup and view all the answers

Monoterpenes consist of two isoprene units and have the molecular formula C______H16.

<p>10</p> Signup and view all the answers

The prototypical acyclic monoterpenoid formed through hydrolysis is ______.

<p>geraniol</p> Signup and view all the answers

The most common ring size in monoterpenes is a ______-membered ring.

<p>six</p> Signup and view all the answers

Monoterpenes may be ______ or contain rings.

<p>linear</p> Signup and view all the answers

Acetyl CoA is the precursor leading to isopentenyl pyrophosphate (IPP), which is the universal precursor for all ______ synthesis.

<p>isoprenoid</p> Signup and view all the answers

The initial steps of the pathway involve three molecules of acetyl-CoA fused to produce ______, known as HMG-CoA.

<p>3-hydroxy-3-methylglutaryl-CoA</p> Signup and view all the answers

HMG-CoA is reduced by HMG-CoA reductase, which is the rate-limiting reaction in ______ biosynthesis.

<p>cholesterol</p> Signup and view all the answers

Mevalonate is phosphorylated by mevalonate kinase and ______, a distinct soluble enzyme.

<p>5-phosphomevalonate kinase</p> Signup and view all the answers

GPP derivatives are associated with ______, a type of terpene.

<p>monoterpene</p> Signup and view all the answers

FPP derivatives can form sesquiterpenes, leading to ______ and steroids.

<p>sterols</p> Signup and view all the answers

Diterpenes consist of four isoprene units and have the molecular formula ______.

<p>C20H32</p> Signup and view all the answers

Isoprene itself is considered the only hemiterpene, while prenol and isovaleric acid are examples of ______.

<p>hemiterpenoids</p> Signup and view all the answers

A common six-membered ring system found in ginger oil is called ______.

<p>zingiberene</p> Signup and view all the answers

Caryophyllene is a classic bicyclic sesquiterpene obtained from the oil of ______.

<p>cloves</p> Signup and view all the answers

One example of a tricyclic compound is ______.

<p>longifolene</p> Signup and view all the answers

Diterpenoids are often encountered in the resins of ______.

<p>conifers</p> Signup and view all the answers

The most common diterpene, which is an acyclic alcohol side chain of chlorophyll, is ______.

<p>phytol</p> Signup and view all the answers

More than ______ different diterpenoid structures have been defined.

<p>3,000</p> Signup and view all the answers

Squalene is known as the simplest triterpenoid in its ______ form.

<p>acyclic</p> Signup and view all the answers

Cyclizations of monoterpenes and sesquiterpenes lead to macrocyclic diterpenes like ______.

<p>casbene</p> Signup and view all the answers

The common example of a sapogenin is ______.

<p>diosgenin</p> Signup and view all the answers

Saponins can hemolyze red blood cells and are known to kill small animals such as ______.

<p>fish</p> Signup and view all the answers

Derris elliptica is traditionally used for poisoning ______.

<p>fish</p> Signup and view all the answers

Bile acids are synthesized in the ______.

<p>liver</p> Signup and view all the answers

Saponins can give a thick ______ when mixed with water.

<p>foam</p> Signup and view all the answers

The most abundant bile acids in human bile are chenodeoxycholic acid and ______.

<p>cholic acid</p> Signup and view all the answers

Saponins contribute to various properties in herbal medicine and are distributed in over ______ plant families.

<p>90</p> Signup and view all the answers

Sapogenins are oxygenated C27 ______ with an hydroxyl group in C-3.

<p>steroids</p> Signup and view all the answers

Bile acids are carried from the liver to the ______, where they are stored for future use.

<p>gallbladder</p> Signup and view all the answers

The synthesis of bile acids is one of the predominant mechanisms for the excretion of excess ______.

<p>cholesterol</p> Signup and view all the answers

Within the intestines, primary bile acids are acted upon by bacteria and converted to secondary bile acids like ______.

<p>deoxycholate</p> Signup and view all the answers

The rate limiting step in bile acid synthesis is catalyzed by the ______.

<p>7α-hydroxylase</p> Signup and view all the answers

Bile acids are ______ by the intestines and delivered back to the liver via the portal circulation.

<p>reabsorbed</p> Signup and view all the answers

The carboxyl group of bile acids is conjugated via an amide bond to either glycine or ______.

<p>taurine</p> Signup and view all the answers

These conjugation reactions yield ______ and tauroconjugates, respectively.

<p>glycoconjugates</p> Signup and view all the answers

The ultimate fate of bile acids is secretion into the ______, where they aid in the emulsification of dietary lipids.

<p>intestine</p> Signup and view all the answers

Flashcards

Isoprenoids

A large class of natural products found in all living organisms, with over 25,000 known types.

Terpenoids

Compounds derived biosynthetically from isoprene units.

Isoprene

The basic constituent of terpenes, a 5-carbon molecule with the formula C5H8.

Isoprene Rule/C5 Rule

The principle that terpenoids are built from repeating isoprene units (C5H8).

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Isopentenyl pyrophosphate

Key precursor to all isoprenoids; an 'active isoprene'.

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Bloch and Lynen

Scientists who elucidated the biosynthetic pathway of isoprenoids.

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Terpenes structure

Can be linear chains or cyclic structures formed from linked isoprene units.

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Biogenic isoprene rule

Ruzicka's hypothesis that a universal isoprene precursor exists for all isoprenoids

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Isopentenyl pyrophosphate (IPP)

A universal precursor for all isoprenoid synthesis.

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Non-mevalonate pathway

Alternative pathway for IPP synthesis using 1-deoxy-D-xylulose 5-phosphate (DOXP).

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HMG-CoA reductase

Enzyme crucial in animal cholesterol biosynthesis, catalyzing the reduction of HMG-CoA to mevalonate.

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Mevalonate

Intermediate in cholesterol biosynthesis forming from HMG-CoA reduction.

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Hemiterpenes

Terpenes composed of one isoprene unit.

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Monoterpenes

Terpenes formed from two isoprene units (C10H16).

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Sesquiterpenes

Terpenes consist of three isoprene units (C15H24).

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Diterpenes

Terpenes built from four isoprene units (C20H32).

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Isoprene Units

Five-carbon structural units that combine to form terpenes.

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Squalene

A linear triterpene crucial in steroid synthesis, found in shark liver oil.

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Tetraterpenes

Terpenes with eight isoprene units, formula C40H56. Examples include carotenoids.

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Carotenoids

Biologically important tetraterpenes, often acting as pigments.

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Monocyclic Sesquiterpene

A sesquiterpene with a single ring structure. It contains 15 carbon atoms and is derived from three isoprene units. Examples include zingiberene found in ginger.

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Macrocyclic Sesquiterpene

A sesquiterpene with a large ring structure containing 15 carbon atoms formed by joining the ends of a chain. An example is humulene.

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Bicyclic Sesquiterpene

A sesquiterpene with two rings. These can incorporate a variety of ring sizes, with classic examples including caryophyllene found in cloves and cadinene.

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Aromatic Bicyclic Sesquiterpenoid

A bicyclic sesquiterpene containing an aromatic ring. Examples include vetivazulene and guaiazulene.

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Tricyclic Sesquiterpene

A sesquiterpene with three rings. Examples include longifolene, copaene and patchoulol.

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Phytol

The acyclic alcohol side chain of chlorophyll. A classic example of a diterpene, it acts as a building block for many other diterpenes.

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Macrocyclic Diterpene

Diterpenes with large rings formed by cyclization similar to the monoterpenes and sesquiterpenes. Examples include casbene, cembrene, and taxadiene.

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Saponin

A type of natural compound found in plants that creates a soapy foam and can kill small animals.

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Sapogenin

The sugar-free part of a saponin molecule, responsible for its specific biological activity.

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Diosgenin

A common sapogenin that can be converted into important steroid hormones.

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Bile Acids

The end products of cholesterol utilization, synthesized by the liver and helping digest fats.

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Cholesterol Utilization

The process of breaking down cholesterol to produce essential bile acids.

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Primary Bile Acids

The most abundant bile acids in human bile, such as chenodeoxycholic acid and cholic acid.

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Foam Test for Saponins

A simple test to detect the presence of saponins in plants by observing foam formation when shaken with water.

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Quinoa Saponin

A type of saponin found in quinoa, a grain with nutritional value.

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Secondary bile acids

Bile acids transformed by bacteria in the intestines. They are formed from primary bile acids through chemical modifications.

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7α-hydroxylase

The enzyme responsible for the rate-limiting step in bile acid synthesis. It adds a hydroxyl group at the 7th carbon position of the cholesterol molecule.

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Bile acid conjugation

The process where bile acids attach to either glycine or taurine within the liver. This makes them more water-soluble, aiding in their secretion and reabsorption.

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Glycoconjugates

Bile acids conjugated with glycine. These conjugates are more water-soluble than the unconjugated forms.

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Tauroconjugates

Bile acids conjugated with taurine. These conjugates are also more water-soluble than the unconjugated forms.

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Bile acid reabsorption

The process where bile acids are reabsorbed from the intestines and returned to the liver via the portal vein. This recycling system conserves these valuable molecules.

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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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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.

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