Natural Products Chemistry Overview
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Questions and Answers

Which of the following compounds are known for their antioxidant, antimicrobial, and anti-inflammatory properties?

  • Alkaloids
  • Terpenes
  • Phenolic Compounds (correct)
  • Sulfur-Containing Compounds

Alkaloids are typically devoid of nitrogen in their chemical structure.

False (B)

What is the significance of glucosinolates in certain plants?

They are sulfur-containing secondary metabolites that may provide protection against pests.

The basic structural unit of phenolic compounds is a ______ unit.

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

Match the following natural products with their examples:

<p>Terpenes = Camphor Phenolic Compounds = Willow Bark Alkaloids = Nicotine Sulfur-Containing Compounds = Garlic</p> Signup and view all the answers

Which stationary phase is commonly used in column chromatography?

<p>Silica (D)</p> Signup and view all the answers

Gas chromatography is suitable for separating non-volatile compounds.

<p>False (B)</p> Signup and view all the answers

What is one advantage of charcoal chromatography?

<p>It is abundant and cheap.</p> Signup and view all the answers

Capillary electrophoresis separates charged species based on the rate of ______ under an electric field.

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

Match the following chromatography techniques to their primary application:

<p>Ion Exchange Chromatography = Separation of charged species Charcoal Chromatography = Adsorption of molecules High Performance Liquid Chromatography = Column chromatography Capillary Electrophoresis = Separation based on electric field</p> Signup and view all the answers

What type of compounds is High Performance Liquid Chromatography primarily used to separate?

<p>Polar compounds (B)</p> Signup and view all the answers

Polyamide gel chromatography is effective for separating polyphenolic compounds.

<p>True (A)</p> Signup and view all the answers

What is the typical mode of High Performance Liquid Chromatography?

<p>Reverse phase mode using C-18 columns.</p> Signup and view all the answers

What is one of the main uses of X-ray crystallography?

<p>Determining the arrangement of atoms in a crystal (C)</p> Signup and view all the answers

Which plant is commonly known as Reishi or Ling Zhi?

<p>Ganoderma lucidum (D)</p> Signup and view all the answers

The absorption difference of left and right circularly polarized light is used to investigate structural aspects of non-chiral media.

<p>False (B)</p> Signup and view all the answers

Elettaria cardamomum is known for its anti-inflammatory effects.

<p>True (A)</p> Signup and view all the answers

What fundamental principle allows crystallographers to produce a 3D picture of the density of electrons within a crystal?

<p>X-ray diffraction</p> Signup and view all the answers

The _____ is used to identify the functional groups that are present in a compound.

<p>IR spectrum</p> Signup and view all the answers

What is the common name of the plant Prunus africana?

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

The common name of Agaricus blazei is ______.

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

Match the following techniques with their purposes:

<p>Mass Spectrometry = Determine molecular weight and isotopic patterns UV-Vis Spectroscopy = Analyze conjugated systems IR Spectroscopy = Identify functional groups NMR Spectroscopy = Characterize hydrogen and carbon types</p> Signup and view all the answers

Which technique is critical for determining how atoms are connected within a molecule?

<p>H-NMR Spectroscopy (A)</p> Signup and view all the answers

Match the following medicinal plants with their corresponding traditional medicine:

<p>Ganoderma lucidum = Traditional Chinese Medicine Elettaria cardamomum = Ayurvedic Medicine Agaricus blazei = Kampo Medicine Prunus africana = African Medicine</p> Signup and view all the answers

What aspect of a crystalline solid does X-ray crystallography provide information about?

<p>The position and identity of each atom</p> Signup and view all the answers

When using NMR, it is important to note both the chemical shifts and coupling patterns.

<p>True (A)</p> Signup and view all the answers

What does size exclusion chromatography primarily separate based on?

<p>Molecular weight (D)</p> Signup and view all the answers

Mass spectrometry can suggest a plausible molecular formula when used with UV spectroscopy.

<p>False (B)</p> Signup and view all the answers

What technique uses powerful magnets to determine the spin systems in molecules?

<p>Nuclear Magnetic Resonance (NMR) spectroscopy</p> Signup and view all the answers

In size exclusion chromatography, when the solvent is organic, it is referred to as __________.

<p>gel permeation chromatography</p> Signup and view all the answers

Which spectroscopy technique is used to determine the functional groups present in a molecule?

<p>IR spectroscopy (B)</p> Signup and view all the answers

Match the following techniques with their primary purpose:

<p>NMR = Determining spin systems in molecules Mass Spectroscopy = Determining molecular weight UV-VIS Spectroscopy = Determining λmax of a compound Circular Dichroism = Analyzing chiral molecules</p> Signup and view all the answers

UV-VIS spectroscopy can compare theoretical and experimental λmax to check structural plausibility.

<p>True (A)</p> Signup and view all the answers

What is the primary technique for determining the molecular weight of a compound?

<p>Mass Spectroscopy</p> Signup and view all the answers

Which of the following compounds is classified as a terpene?

<p>Taxadiene (C)</p> Signup and view all the answers

All terpenes consist of isoprene units linked in a head-to-tail fashion.

<p>True (A)</p> Signup and view all the answers

What is the molecular formula for diterpenes?

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

A triterpene consists of ______ isoprene units and has the molecular formula C30H48.

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

What is the basic molecular formula for terpenes based on the number of isoprene units?

<p>C10H16 (A)</p> Signup and view all the answers

Tetraterpenes contain six isoprene units.

<p>False (B)</p> Signup and view all the answers

How many isoprene units are found in a molecule of farnesol?

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

Match the following types of terpenes with their molecular formulas:

<p>Monoterpene = C10H16 Diterpene = C20H32 Triterpene = C30H48 Tetraterpene = C40H64</p> Signup and view all the answers

Flashcards

Ethnobotany

The study of how people in different cultures use plants for medicinal purposes.

Ganoderma lucidum

A traditional Chinese medicinal mushroom known for its ability to increase energy and boost immunity.

Ayurvedic Medicine

A traditional Indian system of medicine that uses plants, minerals, and other natural substances to treat illnesses.

Kampo Medicine

A traditional Japanese system of medicine that combines traditional Chinese medicine and other ancient practices.

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African Medicine

A traditional medicine system in Africa that emphasizes the use of plants, herbs, and other natural remedies.

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Terpenes

A large class of naturally occurring organic compounds found in plants and animals, characterized by their multiple of five carbon atoms, forming a basic building block of isoprene.

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Isoprene

A five-carbon (C5) branched hydrocarbon unit that is the basic structural unit for terpenes.

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Isoprene rule

The process of linking isoprene units together in a 'head-to-tail' fashion, forming a longer terpene chain.

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Monoterpenes

Terpenes composed of two isoprene units with the molecular formula C10H16.

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Diterpenes

Terpenes consisting of four isoprene units, having the molecular formula C20H32.

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Triterpenes

Terpenes containing six isoprene units and the molecular formula C30H48.

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Tetraterpenes

Terpenes that consist of eight isoprene units with the molecular formula C40H64.

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Polyterpenes

Terpenes containing a long chain of many isoprene units, examples include natural rubber.

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What are phenolic compounds?

A group of small molecules characterized by their structures having at least one phenol unit. They play a role in plant adaptation to environmental stress conditions, exhibit antioxidant, antimicrobial, and anti-inflammatory properties, and are associated with flavor, color, and sensory properties of beer.

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What are alkaloids?

A class of naturally occurring organic nitrogen-containing bases. They generally contain at least one nitrogen atom in an amine-type structure, react with acids to form salts, and have one or more nitrogen atoms as part of a ring structure. Their names often end in '-ine'.

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What are sulfur-containing compounds?

Plants like the Brassicaceae family can synthesize a wide range of sulfur-containing secondary metabolites including glucosinolates, thiosulfinates (like allicin), and reactive sulfur species. These compounds contribute to the plant's defense mechanisms and unique flavors.

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What is camphor?

A type of terpene found in various plants, known for its characteristic pungent aroma and medicinal properties used in traditional medicine.

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What are terpenes?

A terpene is a large class of naturally occurring organic compounds produced by a variety of plants, fungi, and bacteria. They are known for their diverse biological activities and are often found in essential oils.

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Size Exclusion Chromatography (SEC)

A type of chromatography that separates molecules based on their size. It involves the use of a porous gel matrix, where smaller molecules can penetrate the pores and elute later than larger molecules.

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Gel Permeation Chromatography (GPC)

A specific type of SEC that uses an organic solvent as the mobile phase.

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Infrared (IR) Spectroscopy

A powerful analytical technique that provides insights into the functional groups present in a molecule by analyzing its interaction with infrared radiation. It helps identify specific bonds and functional groups within a molecule, providing valuable information for structure elucidation.

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UV-Vis Spectroscopy

A technique that measures the absorbance of a compound at different wavelengths of ultraviolet (UV) and visible (Vis) light. It can help determine the maximum absorbance wavelength (λmax) of a compound, assisting in identifying the presence of conjugated systems and validating proposed structures.

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Mass Spectrometry (MS)

A technique that separates ions based on their mass-to-charge ratio. It's used to determine the molecular weight of a compound and, in conjunction with IR spectroscopy, can suggest possible molecular formulas.

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Nuclear Magnetic Resonance (NMR) Spectroscopy

A powerful technique used to determine the spin system of a molecule by exposing it to a strong magnetic field and analyzing the interaction between the field and the nuclei present in the molecule. This technique is highly effective in revealing details about the structure of the molecule.

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Circular Dichroism (CD) Spectroscopy

A type of spectroscopy that measures the differential absorption of left and right circularly polarized light. It's particularly useful for studying chiral molecules, as these compounds exhibit different absorptions for the two types of polarized light, providing information about their stereochemistry.

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Column Chromatography

A chromatography technique that uses a packed column filled with a stationary phase (e.g., silica, alumina, cellulose) and a mobile phase (similar to those used in TLC) to separate and purify larger amounts of material.

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Gas Chromatography

A chromatography technique that separates volatile compounds by their different boiling points and affinities to a stationary phase inside a heated column. The separated components are detected as they exit the column.

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Ion-exchange Chromatography

A chromatography technique that separates charged molecules based on their interactions with a charged stationary phase.

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Charcoal Chromatography

A chromatography technique that utilizes activated charcoal as a stationary phase for adsorption of molecules. It is a simple and effective method for separating polar compounds, and it can be used with both organic and aqueous solvents.

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High Performance Liquid Chromatography (HPLC)

A high-resolution chromatography type that utilizes a column packed with a stationary phase (often C-18) and a mobile phase to separate complex mixtures of compounds. The reverse phase mode is the most common, where the stationary phase is nonpolar and the mobile phase is polar.

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Capillary Electrophoresis

A technique that separates charged molecules based on their mobility in an electric field. Molecules migrate at different rates based on their charge and size, leading to separation.

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Polyamide Gel Chromatography

Column chromatography using a stationary phase composed of polyamide beads that can form hydrogen bonds with target molecules, leading to separation based on the strength of these bonds.

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Size-Exclusion Chromatography

A chromatography technique that separates compounds based on their molecular size and shape. Larger molecules elute more quickly than smaller ones, as they do not penetrate the pores of the stationary phase as easily.

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X-ray Crystallography

A technique used to determine the arrangement of atoms in a crystalline solid in three dimensions. It utilizes the diffraction of X-rays by the electron clouds of atoms to create a three-dimensional representation of the electron density within the crystal.

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Circular Dichroism

A method used to measure the difference in absorption of left and right circularly polarized light. This technique helps scientists study the structures of optically active molecules (chiral media).

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Structure Elucidation

The process of determining the structure of a molecule by combining information obtained from various spectroscopic techniques. It involves analyzing the spectra from different methods like IR, NMR, and Mass Spectrometry.

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Infrared Spectroscopy (IR)

A spectroscopy technique that measures the absorption of infrared (IR) radiation by molecules. It helps identify the functional groups present in a molecule based on the specific frequencies of absorption.

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Ultraviolet-Visible Spectroscopy (UV-Vis)

A spectroscopy technique that measures the absorption of ultraviolet (UV) radiation by molecules. It helps determine if a molecule contains conjugated systems by identifying characteristic UV absorption bands.

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Nuclear Magnetic Resonance (NMR) Spectroscopy (specifically, H-NMR)

A spectroscopy technique that measures the absorption of radio waves by the nuclei of atoms, specifically hydrogen nuclei. It provides information about the number of types of hydrogen atoms, their connectivity, and their chemical environment within a molecule.

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Carbon-13 Nuclear Magnetic Resonance (NMR) Spectroscopy (specifically, 13C-NMR)

A spectroscopy technique that measures the absorption of radio waves by the nuclei of carbon atoms. It determines the number and types of carbon atoms present in a molecule based on their chemical environments.

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Study Notes

Introduction to Natural Products Chemistry

  • Natural products chemistry is the study of naturally occurring compounds derived from plants, animals, and microorganisms.
  • These compounds have potential for use in drug discovery.

Metabolism

  • Metabolism is the sum of all chemical reactions in a living organism.
  • It encompasses primary and secondary metabolism.

Primary Carbon Metabolism

  • Primary carbon metabolism is part of the process of how all living things obtain energy and nutrients.
  • This process involves photosynthesis and the Krebs cycle, where CO2 is used as a base to create other compounds necessary for building a cell.

Secondary Carbon Metabolism

  • This process isn't vital to the organism in terms of survival, but plays supporting roles in the organism.
  • This process is important in creating specific compounds needed for the organism to thrive in its environment or defend itself.

Metabolites

  • Metabolites are intermediates in metabolic processes.
  • They include primary and secondary metabolites.

Primary Metabolites

  • Directly involved in the normal growth, development, and reproduction of living organisms.
  • Examples include fermentation products (acetic acid, ethanol, lactic acid, citric acid) and cell constituents (lipids, vitamins, polysaccharides).

Secondary Metabolites

  • Not directly involved in normal growth, development, or reproduction.
  • Usually play a role in the organism, but not crucial for survival.
  • Examples include color, scent, sexual attraction, social communication, defense (plant toxins, antibiotics). Many have unknown functions.

Natural Products

  • A chemical substance produced by a living organism, often with distinctive pharmacological effects.
  • Often taken to mean a secondary metabolite.
  • Small compounds generally characteristic of a specific species or closely related family.

Natural Products Chemistry: Sourcing Natural Products

  • Ethnobotany combines anthropology and botany to study traditional uses of plants.
  • Traditional medicines like Traditional Chinese Medicine, Ayurvedic Medicine, Japanese Kampo Medicine, African Medicine, and Native American Medicine are valuable sources for natural products.

Natural Products Chemistry: Methods of Extraction

  • Solvent extraction: Organic solvents (methanol, ethanol) are used to separate soluble compounds from plant material.
    • Crude extracts are obtained initially. Then further separated using liquid-liquid partitioning.
    • Column chromatography used to yield pure compounds.
  • Steam distillation: For separating compounds with lower boiling points from plant material.
  • Supercritical fluid extraction: Supercritical CO2 is used to extract components from material.

Natural Products Chemistry: Separation Techniques

  • Liquid partitioning: Used to separate compounds based on their solubility in different solvents (like water and hexane).
  • Chromatography:
    • Vacuum liquid chromatography: Separates components based on their interaction with a stationary phase.
    • Column chromatography: Separates components based on their interaction with a packed column (silica, cellulose, etc.)
      • Useful for separating compounds from the column.
    • Thin-layer chromatography: Separates components using a silica gel plate and mobile phase.
    • Gas Chromatography: Useful for volatile analytes (like fatty acids, methyl esters, terpenes).
    • Ion exchange chromatography: Useful for separating charged molecules.
  • Capillary electrophoresis: Separates charged species based on their migration rate in an electric field.
  • Polyamide gel chromatography: Uses resin capable of forming hydrogen bonds. Helpful to separate polyphenolic compounds, flavanols, and flavonoids.
  • Size exclusion chromatography (gel permeation): Separates molecules based on molecular weight using organic solvents.

Natural Products Chemistry: Structure Elucidation

  • Spectroscopy:
    • Infrared spectroscopy (IR): Identifies functional groups in molecules through characteristic absorption patterns.
    • Ultraviolet-visible spectroscopy (UV-Vis): Determines the λmax of a compound, helping to assess its structure.
    • Mass spectroscopy (MS): Determines molecular weight and suggests plausible molecular formulas, often used with IR or NMR.
    • Nuclear magnetic resonance spectroscopy (NMR): Provides detailed structural information by looking at the frequencies at which different atoms interact with the magnetic field, often with Hydrogen NMR and Carbon 13 NMR.
    • Circular dichroism (CD): Provides information about the chirality of molecules in a sample.
    • X-ray crystallography: Determines the 3-dimensional arrangement of atoms in crystalline solids by using X-rays.

Plant Secondary Metabolites

  • Terpenes (Examples: Limonene, Linalool, α-pinene)
  • Phenolic Compounds (Examples: Caffeic acid, Cinnamic acid, p-coumaric acid, ferulic acid, sinapic acid)
  • N-Containing Compounds (Examples: Nicotine, Cocaine)
  • Sulfur-Containing Compounds (Examples: Allicin, Glucosinolates, Phytoalexins)

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