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
2
Q
Terpenoids
A
- Synthesized from DMAPP and IPP 5-carbon precursors
- Range from small to large and have many effects
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
4
Q
Monoterpene Lactone
A
- Nepetalactone (found in catnip) is as effective as DEET, but 10x less toxic
5
Q
Iridoids
A
- Bitters
- Basic structure is a cyclopentane ring fused to a 6-membered oxygen heterocycle
- Often occur as glycosides
Example
- Aucubin
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
7
Q
Sesquiterpenes
A
- 15 carbons
- Volatile
- Have acyclic, monocyclic, and bicyclic forms
Examples
- (-)-alpha-bisabolol
- Chamazulene
8
Q
Sesquiterpene Lactones
A
- Artemisnin found in Artemisia
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
10
Q
Diterpenes
A
- Too heavy to be volatile
- Grindelic acid
- Ginkolides
- Paclitaxel
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
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!
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
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)
15
Q
Triterpenoid Saponins
A
- 30-carbon skeleton
- Aglycone is lipophilic
- Sugars are hydrophilic
- Overall molecule is amphipathic
Example
- Glycyrrhizin
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)
