Plant Chem 2 Flashcards
Terpenoids
synthesized from DMAPP and IPP (5-carbon chain precursors w/phosphates)
have a wide variety of sizes and effects
Monoterpenes
10-carbon
low molecular weight – volatile (like EO’s)
can be cyclic or not
small changes to structure give them very different effects
Antiseptic Monoterpines
Thymol - Wild Oregano (also in Thyme) Cineol - Eucalyptus Carvacrol - Oregano Citral A - Lemongrass Terpinen-4-ol - Melaleuca alternifolia
Citrus Monoterpenes
D-limonene - Lemon
Perillyl Alcohol -
both very anti-carcinogenic
Monoterpene Lactones
Lactone = O included in the ring structure
Nepetalactone - Catnip (bug repellent)
Iridoids
Bitters
structure: cyclopentane ring fused to a 6-membered oxygen heterocycle
often as glycosides (+sugar)
Secoiridoid Glycosides
some of the most bitter compounds known
found in Gentiana lutea
structure has 2 6-membered rings w/O
not volatile (large)
Sesquiterpenes
15 Carbons - still volatile
Chamazulene & alpha-bisabolol - Chamomile (anti-inflam compounds)
Sesquiterpene Lactones
Artemisinin - from Wormwood, anti-malarial drug (tea or tincture daily)
Essential Oils
small, aromatic molecules
phenylpropanoids, monoterpenes, sesquiterpenes, hepiterpes
alcohol = -ol, ketone = -one, aldehyde = -al, ether = -ole
EO’s DO NOT HAVE RESIN COMPONENTS (don’t have di- and triterpenes)
Diterpenes
non-volatile, 20-carbons
Grindelic acid - Grindelia
Ginkgolides - Ginkgo
Paclitaxel -
Resins
mixture of terpenoid molecules & other aromatic compounds that combine to form a solid or semi-solid substance excreted by plants in response to injury
solid portion is often di- and triterpenes
aromatic portion is often mono- and sesquiterpenes (–can be distilled out of the resin)
Gum Resins
resins w/a polysaccharide component and volatile oils and heavier terpenes
Boswelia spp. (Frankincense)
Triterpenes
30-carbon skeleton usu pentacyclic usu water-soluble saponins Aglycones are oil-soluble precursors to plant steroids
Ursolic Acid and Oleanolic Acid – both found in Rosemary, Thyme, Lavender, Hawthorn, Olive, &others. Chemoprotective, hepatoprotective, anti-carcinogenic, anti-inflam
Triterpene Glycosides
Actein - from Actea racemosa (cohosh)
compound bound to xylose glycone
Have anti-estrogenic and pro-apoptotic effect on breast cancer cells
not a classic phytoestrogen – doesn’t sit in estrogen receptor
Triterpenoid Saponins
30-carbon skeleton
Aglycone is lipophilic, but sugars are hydrophilic = amphipathic molecule
Ex: Glycyrrhizin
Steroidal Saponins
27-carbon skeleton
have multiple sugar units
many anti-inflam and adaptogenic molecules
–modulate hormone activity, but it’s not hormone replacement
-genin = aglycone
Ex: Diosgenin, Dioscin
Phytosterols
tetracyclic
act in plant cell membranes like cholesterol in ours
plant growth regulators
found in plant oils & lipophilic extracts
beta-sitosterol
Cardiac Glycosides
tetracyclic sterol skeleton w/a 5-membered lactone ring on an aglycone
cardioactive substances from plants like Digitalis spp. and Convallaria spp.
–slow and strengthen the heartbeat, generally low-dose herbs
Tetraterpenes (Carotenoids)
40-carbon chains (only CH)
lipophilic, w/terminal cyclic structures
carotenoids concentrate in tissues providing antioxidant protection
Ex: lutein & zeaxanthin in macula give it a yellow color
Lycopene is the precursor
Xanthophylls
oxygenated carotenoids
can have ketone, hydroxyl, epoxide groups
Alkaloids
Nitrogenous molecules (N is often in a ring)
occur as salts or N-oxides in plants
alkaline
soluble in hydroethanolic menstrum
Nonheterocyclic Amines
there are cyclic structures, but N is not in the cycle
Ex: Ephedrine, mescaline
Methylxanthines
purine alkaloids
Ex: Theophylline, Theobromine, Caffeine
–N included in rings
