Plant Chem 2

Question 1

Terpenoids

Answer 1

synthesized from DMAPP and IPP (5-carbon chain precursors w/phosphates)
have a wide variety of sizes and effects

Question 2

Monoterpenes

Answer 2

10-carbon
low molecular weight – volatile (like EO’s)
can be cyclic or not
small changes to structure give them very different effects

Question 3

Antiseptic Monoterpines

Answer 3

Thymol - Wild Oregano (also in Thyme)
Cineol - Eucalyptus
Carvacrol - Oregano
Citral A - Lemongrass
Terpinen-4-ol - Melaleuca alternifolia

Question 4

Citrus Monoterpenes

Answer 4

D-limonene - Lemon
Perillyl Alcohol -
both very anti-carcinogenic

Question 5

Monoterpene Lactones

Answer 5

Lactone = O included in the ring structure

Nepetalactone - Catnip (bug repellent)

Question 6

Iridoids

Answer 6

Bitters
structure: cyclopentane ring fused to a 6-membered oxygen heterocycle
often as glycosides (+sugar)

Question 7

Secoiridoid Glycosides

Answer 7

some of the most bitter compounds known
found in Gentiana lutea
structure has 2 6-membered rings w/O
not volatile (large)

Question 8

Sesquiterpenes

Answer 8

15 Carbons - still volatile

Chamazulene & alpha-bisabolol - Chamomile (anti-inflam compounds)

Question 9

Sesquiterpene Lactones

Answer 9

Artemisinin - from Wormwood, anti-malarial drug (tea or tincture daily)

Question 10

Essential Oils

Answer 10

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)

Question 11

Diterpenes

Answer 11

non-volatile, 20-carbons
Grindelic acid - Grindelia
Ginkgolides - Ginkgo
Paclitaxel -

Question 12

Resins

Answer 12

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)

Question 13

Gum Resins

Answer 13

resins w/a polysaccharide component and volatile oils and heavier terpenes
Boswelia spp. (Frankincense)

Question 14

Triterpenes

Answer 14

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

Question 15

Triterpene Glycosides

Answer 15

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

Question 16

Triterpenoid Saponins

Answer 16

30-carbon skeleton
Aglycone is lipophilic, but sugars are hydrophilic = amphipathic molecule
Ex: Glycyrrhizin

Question 17

Steroidal Saponins

Answer 17

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

Question 18

Phytosterols

Answer 18

tetracyclic
act in plant cell membranes like cholesterol in ours
plant growth regulators
found in plant oils & lipophilic extracts

beta-sitosterol

Question 19

Cardiac Glycosides

Answer 19

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

Question 20

Tetraterpenes (Carotenoids)

Answer 20

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

Question 21

Xanthophylls

Answer 21

oxygenated carotenoids

can have ketone, hydroxyl, epoxide groups

Question 22

Alkaloids

Answer 22

Nitrogenous molecules (N is often in a ring)
occur as salts or N-oxides in plants
alkaline
soluble in hydroethanolic menstrum

Question 23

Nonheterocyclic Amines

Answer 23

there are cyclic structures, but N is not in the cycle

Ex: Ephedrine, mescaline

Question 24

Methylxanthines

Answer 24

purine alkaloids
Ex: Theophylline, Theobromine, Caffeine
–N included in rings

Question 25

Pyridine Alkaloids

Answer 25

Ex: Nicotine, Trigonelline (Fenugreek)

Question 26

Piperidine Alkaloids

Answer 26

Piperidine base

Ex: Lobeline, Piperine (black pepper), Coniine

Question 27

Pyrrolizidine Alkaloids

Answer 27

Pyrrole base
Ex: Symphytine
Necine system – pyrrole + another 5-member ring bound
some are hepatotoxic
Found in Symphytum (Comfrey), Tussilago farfara, Petasites spp.
varying degrees of toxicity

Question 28

Qinoline Alkaloids

Answer 28

Quinoline base

Ex: Quinine

Question 29

Isoquinoline Alkaloids

Answer 29

Isoquinoline base

Ex: Berberine

Question 30

Indole Alkaloids

Answer 30

Indole Base

Ex: Reserpine

Question 31

Tropane Alkaloids

Answer 31

Tropane base - complicated 3D structure
Ex: Atropine (Belladonna, toxic) = Hyoscymine mixture
Seen in plants driving sympathetic fxns

Question 32

Polysaccharides - Inulin

Answer 32

Inulin is oligosaccharide
Seen in onions, garlic, artichoke, dandelion, burdock, chicory
prebiotic, soluble fiber

Question 33

Pectins

Answer 33

heteropolysaccharides that can trap water in a 3D structure
soluble fiber
helical galacturonic acid backbone w/varying sugars

Question 34

Mucilage

Answer 34

for gels/slime w/water
Found in Althea officinalis (marshmallow), Ulmus fulva (slippery elm)
soothing, emollient
usu mucilages are also immunomodulating polysaccharides

Question 35

Immunomodulating Polysaccharides

Answer 35

complex mixtures of heteropolysaccharides and polysac protein complexes that effect the immune system
actions vary from stim of hematopoiesis to inc production of CKs
Ex: Arabinogalactans, Acemannans, beta-glucans