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Botanical Materia Medica II > Week 1 - Plant Chemistry Part 1 - Phenolic Compounds > Flashcards

Week 1 - Plant Chemistry Part 1 - Phenolic Compounds Flashcards

1
Q

Pharmacognosy

A
  • The study of physical, chemical, biochemical, and biological properties of drugs, drug substances, or potential drugs or drug substances of natural origin, as well as the search for new drugs from natural sources
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2
Q

Secondary Metabolites

A
  • Compounds that are not directly involved in the growth, reproduction, or photosynthesis of plants
  • Derived from primary metabolites
  • Have a vast array of functions
  • Generally associated with the defense from other organisms, attraction of pollinators and other symbiotes, and protection from environmental factors such as UV radiation
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3
Q

Naming Constituents

A
  • Usually based on Latin names
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4
Q

Phenolic Compounds

A
  • Aromatic (benzene) ring with an -OH group

- Range from simple compounds with a single aromatic ring to complex polymeric molecules

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5
Q

Common Properties of Phenolic Constituents

A
  • Resonance stabilization
  • Antioxidants
  • Anti-inflammatory
  • Anti-cancer
  • Many phenolics are colorful pigments
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6
Q

Phenolics

A
  • Simple phenolics
  • Phenolic glycosides
  • Tannins
  • Proanthocyanidins
  • Coumarins
  • Furanocoumarins
  • Anthraquinones (and their glycosides)
  • Naphthoquinones
  • Phenolic Acids
  • Chromones
  • Furanochromones
  • Flavonoids
  • Isoflavones
  • Lignans
  • Stilbenes
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7
Q

Simple Phenolic Compounds

A
  • Contain a single aromatic ring
  • Often form glycosides
  • Varying side groups
  • Smaller molecules are volatile
Examples
- Eugenol
     > Present in Syzgium aromaticum (Clove), Artemesia spp., Cinnamomum spp., Ociumum spp.
     > Component of the essential oils
- Vanillin
- Methyl Salicylate
     > Volatile constituent found in Gaultheria procumbens (Wintergreen) and Betula spp. (Birch)
     > Potential for toxicity
- Humulone
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8
Q

Phenolic Glycosides

A
  • Phenolic compound with a sugar group
  • The sugar moiety is known as the glycone
  • The phenolic portion is known as the aglycone

Example
- Arbutin
> From Arctostaphylos uva-ursi
> Hydroquinone plus glucose

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9
Q

Phenolic Acids

A
  • At least one phenolic ring with an acidic carboxyl group
Examples
- Ellagic acid
     > Found in berries, grapes, and pomegranate
     > Anti-inflammatory
     > Anti-carcinogenic
- Gallic acid
     > Found in grapes, berries, and nuts
     > Anti-inflammatory
     > Anti-carcinogenic
- Salicylic acid
     > Anti-inflammatory
     > Analgesic
     > Antipyretic
     > Not the same effect on platelets as acetylsalicylic acid (aspirin)
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10
Q

Tannins

A
  • Astringent
  • Have the ability to cross-link collagen fibers, tightening tissues
  • Phenolic acids (such as gallic acid or ellagic acid) with ester linkages to a central glucose molecule

Example
- Geraniin
> Found in Geranium maculatum and other spp.

Plants high in tannins

  • Quercus spp. (Oak)
  • Hamammelis virginiana (Witch Hazel)
  • Aesculus hippocastanum (Horse Chestnut)
  • Camellia sinensis
  • Cinnamomum spp.
  • Rheum spp. (Rhubarb)
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11
Q

Coumarins and Furanocoumarins

A
  • Derivatives of alpha-pyrone
  • Aromatic
  • Produce a fresh-cut grass aroma
  • Components of essential oils
  • Furanocoumarins have a photosensitizing effect
  • Responsible for the grapefruit juice effect (CYP3A4 and CYP3A5 inhibitors)
  • Commonly found in leguminoseae, apiaceae, and rutaceae families

Examples of coumarins

  • Archangelicin
  • Umbelliferone
  • Aesculetin

Examples of furanocoumarins

  • Bergapten
  • Psoralen
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12
Q

Chromones and Furanochromones

A
  • Derivatives of benzo-gamma-pyrone

Example of chromones
- Eugenin
> In Syzgium aromaticum (Clove) and carrots
> Contributes a bitter taste

Example of furanochromones
- The primary active constituents of Khella (Bishop's Weed)
     > Ammi visnaga
     > Khellin
     > Visnagin
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13
Q

Naphthoquinones

A
  • Pigmented molecules
  • Fungicidal
  • Antibacterial
  • Insecticidal
  • Phytotoxic
  • Cytostatic
  • Anti-carcinogenic
  • Anti-helminthic

Example
- Juglone
> Darkly-pigmented
> From Juglans nigra (Black Walnut)

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14
Q

Anthraquinones

A
  • Polyphenolic compounds
  • Many are pigmented
  • Most well-known class of plant-based laxatives and purgatives
  • Many occur as glycosides
Examples
- Hypericin
     > From Hypericum perforatum (St. John's Wort)
     > Non-laxative
- Sennidin
     > From Cassia senna
- Aloin
     > From Aloe spp.
- Emodin and frangulin
     > From Rhamnus purshiana or Rhamnus frangula (Buckthorn)
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15
Q

Flavonoids

A
  • Colorful
  • Cooling
  • Anti-inflammatory
  • Made up of 3 aromatic rings
  • Flavus = yellow
  • Flavones
  • Favonols
  • Flavanones
  • Flavan-3-ols
  • Isoflavones
  • Biflavones
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16
Q

Flavone

A 
Examples
- Chrysin
     > Found in Passiflora (Passionflower)
- Apigenin
     > Found in Petroselinum (Parsley)
- Luteolin
     > Found in Cynara scolymus (Artichoke)
     > Found in many culinary herbs
- Vitexin
     > Flavone glycoside
     > Found in Vitex agnus-castus
17
Q

Flavanones

A 
Examples
- Eriodictyol
      > Found in Yerba santa
- Hesperitin
- Naringenin
     > CYP450 inhibitor
18
Q

Flavonol

A 
Examples
- Quercitin
- Kaempherol
- Rutin
     > Flavonol glycoside
19
Q

Flavan-3-ol

A
  • Catechins

- Epicatechins

20
Q

Isoflavone

A
  • Phytoestrogens found in soy, red clover, and kudzu

Examples

  • Genestein
  • Diadzein
  • Formononetin
21
Q

Biflavones

A
  • Two flavonoid molecules stuck together
    Example
  • Amentoflavone
    > Found in Ginkgo, Hypericum, and Rhus spp.
22
Q

Anthocyanidins

A
  • Structurally related to flavones, but carry a charge
  • Greek antho = flower, kyanos = blue
  • Smaller than anthocyanins
  • Often dark red/blue/purple
  • Pigments are pH-dependent
  • Sap pigments
  • Based on the flavylium ion (+)

Examples

  • Pelargonidin
  • Cyanidin
  • Peonidin
  • Delphinidin
  • Petunidin
  • Malvidin
23
Q

Anthocyanins

A
  • Anthocyanidins with a sugar moiety (glycosides)
  • Generally odorless and flavorless
  • Mildly astringent
  • Very colorful (red and blue)
  • In fruits
24
Q

Condensed Tannins/Proanthocyanidins

A
  • Related to flavonoid pigments
  • No sugar moiety
  • Oligomers and polymers of flavon-3-ol moieties
  • Not readily hydrolyzed to simpler molecules
  • Astringent

Examples of proanthocyanidins

  • Crataegus spp. (Hawthorne) oligomeric proanthocyanidins (OPCs)
  • Cinnamon
  • Green Tea
  • Cocoa
  • Linden flower
  • Wild cherry
  • Grape seed and skin
  • Apples
  • Pine bark
25
Q

Lignans

A
  • Dimeric compounds formed by two phenylpropene derivatives
  • Major class of phytoestrogens
  • Have antioxidant functions
  • Some forms have toxicity
    > Podophyllotoxin
  • Some are hepatoprotective
    > Silybin and Silymarin

Flax lignans

  • Occur in flax as lignan precursors that are changed by enteric bacteria to enterolignans (such as enterodiol and enterolactone)
  • Secoisolariciresinol is the dominant lignan precursor found in Flax seeds
  • Enterolactone is the product of bacterial metabolism

Plants known for their lignans

  • Linum usitatissimum (Flax)
  • Silybum marianum (Milk Thistle)
  • Schisandra chinensis
  • Zanthoxylum clava-herculis
  • Eleutherococcus
Neolignans
- Phenylpropene units linked head-to-head or head-to-tail
- Examples
     > Magnolol
     > Honokiol
26
Q

Stilbenes

A
  • Great antioxidant capacity
  • Two phenolic rings connected by a conjugated bridge
  • Example
    > Resveratrol
27
Q

Other Phenolic Compounds - Curcumin

A
  • Found in Turmeric
  • Two phenolic rings joined by conjugated alpha and beta carbonyl groups to form a diketone
  • Very antioxidant
28
Q

Other Phenolic Compounds - Rosmarinic Acid

A
  • Anxiolytic

Found in

  • Melissa officinalis (highest amount)
  • Mentha piperita (Peppermint)
  • Thymus vulgaris (Thyme)
  • Ocimum sanctum (Holy Basil, Tulsi)
  • Ocimum basillicum (Basil)
  • Origanum majorana (Marjoram)
  • Rosmarinus officinalis (named for) (Rosemary)
29
Q

Other Phenolic Compounds - Capsaicin

A
  • Phenolic portion with an amide and an aliphatic tail

- Some classify it as a phenolic compound, and others classify it as a pseudo-alkaloid

30
Q

Propolis

A
  • Cottonwood trees put out buds with a sticky phenolic resin
  • Bees collect the resin and make it into propolis
  • Strong antimicrobial that protects the hive
  • Used medicinally for immunomodulatory, anti-inflammatory, and anti-ulcer effects

Botanical Materia Medica II (6 decks)

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