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Botanical Materia Medica II > Week 2 - Plant Chemistry Part 2 - Volatile Oils, Resins, Terpines, Saponins, Alkaloids, Cardiac Glycosides, Polysaccharides, Sterols, and More... > Flashcards

Week 2 - Plant Chemistry Part 2 - Volatile Oils, Resins, Terpines, Saponins, Alkaloids, Cardiac Glycosides, Polysaccharides, Sterols, and More... Flashcards

1
Q

Terpenes

A
  • Monoterpenes
  • Sesquiterpenes
  • Diterpenoids
  • Triterpenoids
  • Tetraterpenes - Carotenoids
  • Polyterpenoids
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2
Q

Terpenoids

A
  • Synthesized from DMAPP and IPP 5-carbon precursors

- Range from small to large and have many effects

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3
Q

Monoterpenes

A
  • Low molecular weight
  • 10-carbon molecules
  • Structural variations
    > Monocyclic, bicyclic, acyclic
  • Components of essential oils
  • Varied effects (antiseptic to vulnerary to psychotropic)

Examples

  • Linalool
  • Pulegone
  • Alpha-thujone
  • Thymol
  • Cineol
  • Carvacrol
  • Citral A
  • Terpinen-4-ol
  • D-limonene
  • Perillyl Alcohol
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4
Q

Monoterpene Lactone

A
  • Nepetalactone (found in catnip) is as effective as DEET, but 10x less toxic
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5
Q

Iridoids

A
  • Bitters
  • Basic structure is a cyclopentane ring fused to a 6-membered oxygen heterocycle
  • Often occur as glycosides

Example
- Aucubin

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6
Q

Secoiridoid Glycosides

A
  • Two 6-membered rings fused together
  • Some of the most bitter constituents known
  • Causes bitter principles of Gentiana lutea
    > Amarogentin
    > Gentiopicrin
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7
Q

Sesquiterpenes

A
  • 15 carbons
  • Volatile
  • Have acyclic, monocyclic, and bicyclic forms

Examples

  • (-)-alpha-bisabolol
  • Chamazulene
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8
Q

Sesquiterpene Lactones

A
  • Artemisnin found in Artemisia
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9
Q

Essential Oils

A
  • Contain small aromatic molecules
  • Phenylproponoids, monoterpenes, sesquiterpenes, and hemiterpenes in the form of alcohols, aldehydes, ethers, esters, ketones, and peroxides
  • Suffix tells us what molecule is
    > Alcohol -ol
    > Ketone -one
    > Aldehyde -al
    > ether -ole
  • Identify and verify quality of essential oils by organoleptic evaluation and gas chromatographs
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10
Q

Diterpenes

A
  • Too heavy to be volatile
  • Grindelic acid
  • Ginkolides
  • Paclitaxel
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11
Q

Resins

A
  • Amorphous blob from coniferous trees
  • Mixture of terpenoid molecules and other aromatic compounds that combine to form a solid or semi-solid substance that is excreted by plants for protection or in response to injury
  • Solid/semi-solid structure comes from di- or triterpenes
  • Aromatic portion is from mono- and sesquiterpenes
  • Aromatic components can be distilled from heavier resinous components
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12
Q

Gum Resins

A
  • Resins that have a polysaccharide component as well as volatile oils and heavier terpenes
  • Boswelia spp. (Frankincense)
    > Very powerfully anti-inflammatory d/t triterpenes
    > Essential oils don’t have the same anti-inflammatory effects as resin!
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13
Q

Triterpenes

A
  • 30-carbon skelton
  • Usually pentacyclic
  • Usually occur as water-soluble saponins
  • Aglycones are oil-soluble
  • Precursors to plant steroids

Examples

  • Ursolic Acid
  • Oleanolic Acid
  • Both found in Rosemary, Thyme, Lavender, Hawthorne, Olive, and others
  • Chemoprotective, hepatoprotective, anticarcinogenic, and anti-inflammatory
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14
Q

Triterpene Glycosides

A
  • Actein
    > One of a group of triterpene glycosides in Actea racemosa
    > Bound to a xylose glycone
    > Have anti-estrogenic and pro-apoptotic effect on breast cancer cells
    > Not a classic phytoestrogen! (does not sit on estrogen receptor)
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15
Q

Triterpenoid Saponins

A
  • 30-carbon skeleton
  • Aglycone is lipophilic
  • Sugars are hydrophilic
  • Overall molecule is amphipathic

Example
- Glycyrrhizin

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16
Q

Steroidal Saponins

A
  • 27-carbon skeleton
  • Have multiple sugar units attached (usually 3-5)
  • Many are anti-inflammatory and adaptogenic
  • Suffix “-genin” denotes the aglycone

Examples

  • Diosgenin
  • Dioscin
17
Q

Phytosterols

A
  • Tetracyclic
  • Act in plant cell membranes like cholesterol in animal cell membranes
  • Plant growth regulators
  • Found in plant oils and lipophilic extracts
    > Avocado or olive oils
18
Q

Cardiac Glycosides

A
  • Tetracyclic sterol skeleton with an additional 5-membered lactone ring attached to the aglycone
  • Cardioactive substances
    > From Digitalis spp.
    > From Convallaria spp. (less dangerous than Digitalis)
  • Low Dose!

Example
- Digitoxin

19
Q

Tetraterpenes (Carotenoids)

A
  • 40-carbon chains
  • Lipophilic, multiple conjugated double bonds
  • Terminal cyclic structures
  • Various carotenoids concentrate in tissues providing antioxidant protection
    > Ex: lutein and zeaxanthin concentrate in the macula giving it a yellow color
  • Lycopene is the precursor molecule
  • Beta-carotene (example?)
20
Q

Xanthophylls

A
  • Are oxygenated carotenoids
  • Have ketone, hydroxyl, and epoxide groups on their rings
  • Lutein
21
Q

Alkaloids

A 
- Nitrogenous molecules
     > Nitrogen is often contained in a heterocyclic ring
- Occur as salts or N-oxide in plants
- Have an alkaline nature
- Soluble in hydroethanolic menstrum
  • If put vinegar in tincture, it’ll pull more of the alkaloid out (acid-alcohol)
  • Dramatic in action, contain N, better w/ acid, end in -ine
  • Nonheterocyclic, pyridine, piperdine, pyrrolizidine, indole, quinoline, isoquinoline, purine/methyxanthines, tropane
22
Q

Nonheterocyclic Amines

A
  • There are cyclic structures, but the nitrogen isn’t within them

Examples

  • Ephedrine
  • Mescaline
23
Q

Methylxanthines

A
  • Also known as purine alkaloids
  • Nitrogen in cycle

Examples

  • Theophylline
  • Theobromine
  • Caffeine
24
Q

Pyridine Alkaloids

A
  • Some have one nitrogen, but others have many

Examples

  • Nicotine
  • Trigonelline
25
Q

Piperidine Alkaloids

A
  • Lobeline from Lobelia
  • Piperine from Piper nigra
  • Coniine
    > Very toxic (caused death of Socrates)
26
Q

Pyrrolizidine Alkaloids

A 
- Necine system!!
     > Two cycles joined together
- Some of these are toxic
      > Why we recommend not taking Comfrey internally
     > Can have sequellae years later
  • Found in Symphytum officinale (Comfrey), Tussilago farfara (Coltsfoot), and Petasites spp.
  • Potentially hepatotoxic and hepatocarcinogenic
  • Ones saturated at the 1,2 position of the necine ring are non-toxic
    > E. purpura
  • The macrocyclic and mono- and diesters have varying degrees of toxicity
27
Q

Quinoline Alkaloids

A
  • Not considered polyphenolic because has nitrogen

- Quinine was used to treat malaria

28
Q

Isoquinoline Alkaloids

A
  • Nitrogen is in a different spot

- Berberine

29
Q

Indole Alkaloids

A
  • Reserpine
30
Q

Tropane Alkaloids

A
  • Seen in low-dose Solanaceae family

Example
- Atropine
> Racemic mixture of D- and L- Hyoscymine
> Found in Belladonna, Hyoscyamus, and Stramonium

  • Symptoms from anticholinergic poisoning are Blind as a Bat, Mad as a Hatter, Red as a Beet, and Hot as Hades
31
Q

Polysaccharides

A

Inulin

  • Oligosaccharide
  • Sources: onion, garlic, artichoke, dandelion, burdock, chicory (up to 80%)
  • Named for Inula helenium
  • Prebiotic
  • Soluble fiber
32
Q

Pectins

A
  • Heteropolysaccharides that can trap water in a 3-D structure
  • Soluble fiber
  • Helical galacturonic acid backbone with varying sugar side groups
  • Long chain
  • Fruits (pears, apples, blueberries
  • Hawthorne berries cook into a gelatinous mass
33
Q

Mucilage

A
  • Form gels or slime with water
  • Found in Althea officinalis and Ulmus fulva
  • Generally soothing and emollient
  • Significant crossover between mucilages and immunomodulating polysaccharides (why they can help with IBD)
34
Q

Immunomodulating Polysaccharides

A
  • Complex mixtures of heteropolysaccharides and polysaccharide protein complexes that effect the function of the immune system
  • Studied modes of action vary from stimulation of hematopoiesis to increasing production of various cytokines
  • Common names of Ips: Arabinogalactans, Acemannans, PSI, PSII, PS-K (from trametes versicolor), and beta-Glucans (from mushrooms)

Botanical Materia Medica II (6 decks)

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