Plant Constituents
Part I
School of Traditional Western Herbalism
May 2010
Sharon Woodard ND,
Kathryn Kloos ND (candidate)
Copyright 2010
What we are talking about
• Primary Metabolites: what the plant makes for
basic life support
– Carbohydrates
– Proteins
– Lipids
• Secondary Metabolites: everything else
what plants make to solve problems of life
support: predation, environmental stress,
growth, reproduction
The scope we are dealing with
Estimate of 275,000 diff species on earth
Each has hundreds to thousands different
unique chemicals
Individual plants in different situations
produce unique chemical Profiles
Any variation in the combination of these
variables produces its own synergy and
effects
But wait, there’s more!
Plants constantly monitor their environment and
respond by changing their chemistry
• Seeds:
– create their own sterile womb
– contain food for the journey
• roots: create a biosphere around themselves
• mature plants:
– Create and feed complex communities that provide
it with food , communication and protection
– produce medicine for themselves
– protect themselves from predation
And more complexity
• All these chemicals vary based on species,
season, time of day, individuality of plant,
environmental stressors and plants can
change what is produced based on need.
how do we approach this topic?
Medico scientific mindset:
botanicals are a source of chemicals.
break down the crude material into
constituents, study in unrelated components,
make decisions about what is extraneous and
what is active enabling a predictable result.
Goal: predictability of action. Control over the
process. Manageability of the study. Isolate
parts, disregard the integrity of the whole.
Traditional Herbalism approach
Understand the individual constituents
Become aware of the patterns of different
constituents in the whole plant
Start to recognize the emerging logic and
personality of the plant
Apply this knowledge in a specific and
individualized fashion.
Today we are starting that process…
The fad of the hour is to break down
substances, not into patterns, but into piles of
unrelated substances. Herbs are not ultimate
discreet substances and therefore do not fit
this paradigm. They are inconvenient.
Sickness is something which has outsmarted
the little bit of nature within us, so it is very
intelligent. If we hope to contend with it, we
have to be humble.
• Matthew Wood The Book of Herbal Wisdom
The Anthroposophical approach;
• Matter vs form: something informs matter to
take shape. The information over time allows
matter to turns this form into a gesture.
(analogous to doctrine of signatures)
• Disease is disorganized form and that
disorganization can be corrected by
reconnecting to the organizing information
• Plants work as healing forces because they
bring information and form back to tissue.
Reasons to understand the
constituents
1. to explain and provide evidence for the
historically understood actions.
2. to suggest new uses that aren’t part of
traditional usage.
3. to increase practionor literacy and make the
written literature more available.
4. to use appropriate methods for processing
and delivery of the medicine.
5. to be aware of toxicology
Before we start
Basic Organic chemistry
see Handout
Botanical production of herbal constituents
see Handout
Carbohydrates: Polysaccharides
Carbohydrates: Polysaccharides
Definition
huge structures made up of long chains of
sugar derivatives and/or urionic acid
molecules linked together.
Characteristics are determined by the type of
sugar and how they are bonded.
CHO: Function in plants
Structural; provide rigidity of cell walls or
flexibility of form as in algae
Energy storage: poly saccharides in plants,
glycogen in animals
Protection against injury
from dehydration: soak and hold onto water
from predation or infection via physical
barrier or toxic reaction
CHO: Behavior in general
Form gels: the strands knit together in a way
that traps liquid. The tighter the weave the
more rigid the form.
Can be broken down with addition of solvants
or minerals.
Tend to be sticky or tacky.
CHO: General Properties
• Hydrophilic; attracts water
• Indigestible: usually not digestible, but even
if they are broken down the are inert
• Physical properties of soothing, protecting
demulcent, emollient
• Taste, energetics: Bland, neutral, cooling and
sweet, lubricating, mild
• Gesture: trapped water
CHO: Solubility, delivery of medicine;
Precipitates in alcohol
Soluble in water
• mucilages form long slimy chains: less water
soluble
• Gums are branched chains creating a matrix
or tacky gel: absorb more water
Pharmacology: Mucilages
LOCAL:
• demulcent; sooths and protects irritated, exposed
areas in GI and skin
• Retain heat due to high water content
• In GI: soothing, protecting ulcerated area, Resistant to
digestive secretions and often reach the colon intact.
• Laxative: draws in moisture and bulk increases
peristalsis
• Antidiarrheal: absorb excess water in colon
• Absorb toxins and waste
• Calms the enteric nervous system
CHO: Pharmacology: Mucilages
REFLEX:
Demulcent effect in the GI occurs simultaneously in the
urinary and respiratory tract as well.
What?
All three systems share an embryonic connection and
share information through common nerve pathways.
• Bronchial: calm irritable cough, Reduce spasm,
lubricate passages
Symphytum off.
• Urinary ducts: reduce colic due to stones, infections
Althea off.
Examples of gums and mucilage
Gums
Acacia spp. :Gum Arabic; very water soluble,
makes a soothing syrup and effective emulsifier.
Is digested and absorbed but nontoxic
Prosopis spp. :Mesquite Gum
Prunus spp. : Cherry gum
Mucilages
Linum spp; Flax seed
Plantago spp. : Psyllium seed
Ulmus fulva: slippery elm bark
Symphytum off. Comfrey rt
Althea off marshmallow rt.
Tussilago farfara coltsfoot
Immunostimulating polysaccharides
A specific class of very large branched chains of sugar
molecules
Somehow the combination of its 3D structure and the
nature of the bonds stimulates the immune system
leading to
-immune stimulation; active recruitment of WBC
both directly and through remote chem messages
-immune modulation: somehow, the immune
system becomes leaner and more precise.
-anti tumor activity: somehow makes the immune
response to tumors more effective
Immunostimulating polysaccharides
the chlorella example
Chlorella, single cell fresh water algae
-on earth for 2.5 billion years so it knows how to survive
- has the highest concentration of chlorophyll of any plant
- has an extremely efficient DNA repair
- very large branched chain polysaccharides
How it stimulates our immune system
1. Increases interferon: a chemical messenger that works locally and
systemically.
2. Stimulates all the WBC: MQ, T and B making it anti viral and
antibacterial.
3. Shown to tighten gums and grow new tissue in the mouth
4. (cell wall) Chelates out cadmium, pesticides, PCBs
5. Used in liver toxicity, constipation, anti viral regimes, ulcers, skin
problems, allergies, asthma, HT….
IMMUNOSTIMULATING
POLYSACCHARIDES: pharmacology
• Immunmodulating:
stimulate cytokines which then increase proliferation and differentiation
of MQ, T and B cells, antitumor and antibody activity
Ex; Grifola frondosa : Maitake mushroom
• Immune stimulating:
stim WBC, ( all of them; MQ,mono, NK): anti-inflam, bactericidal,
Immunmodulating ( calms auto immune issues)
Ex; Ganoderma lucidum: Rieshi
increases production of interferon which stim MQ, anti tumor, anti viral
Ex: Chlorella, single cell fresh water algae
• Anti tumor; MQ activation; but different from CA drugs, not cytotoxic
instead it just increases the immune systems attack on the tumor.
Ex; Lentinus edodes: shiitake
IMMUNOSTIMULATING
POLYSACCHARIDES
Mysteries:
1. chemical assays don’t show these properties
only biologic testing can produce these results and
the results are consistent.(effects only living systems)
2. somehow the 3D structure effects the immune system:
broken bonds or denatured shapes don’t have the
same effect.
3. Yet they, as a group are indigestible: if they were
broken down as in regular digestion, then it would be
individual sugars no bonds, no geometric shape.
4. Hot water infusions seem to be most effective.
Immune stimulating Polysaccharides
theories of action:
1. The intact molecule is taken into the gut cells intact
through pinocytosis then released whole into the
bloodstream.
- really? Huge molecules are antigenic, the gut works
hard to avoid this. We work hard at healing leaky gut.
Seems unlikely.
2. Its as if these constituents help the body deal with
tumors more efficiently, as if the immune system has
more information. Its as if there is a mobilization of
the immune system.
Is this an example of an exchange of information
between species?
Examples of herbs with
Immunstimulating polysaccharides
•
Aloe spp.
•
•
Actractylodes spp. •
•
Astragalus
•
•
Baptisa tinctoria
•
•
Seranoa seeulata
•
• Eleutheroccus senticosus •
•
Cinnamomum bark •
•
Codonopsis pilosula •
•
Curcuma zedoaria
•
•
Isatis indigotica
Panex notoginseng
Bupleurum root
Glycyrrhiza root
Panax pseudoginseng
Rehmannia root
Salvia miltiorrhiza
Zizyphusfruit
Echanacea spp
Angelica sinensis
Misc polysaccharides: Pectins
Found mainly in roots and fruits,
• Galactouronic carbohydrates, in plant cell wall
• Properties similar to gums;
absorptive and bulk laxative
antiseptic and healing paste for ulcers
diarrhea and dysentery: absorbs liquid, slows
slows glucose absorption in gut
Fructans
Soluble in hot water, it’s a storage form of polymers of fructose
Inulin: main one used in phytotherapy
not digested passes to GI unchanged
increases renal flow
stabilizes blood sugar
Diuretic
Immunostimulating
Found in:
Poaceae: grass fam, Liliacease: lily fam, Asteraceae
Arctium lappa, Inula helenium
Cynara scolymus Taraxicum off.
Echinacea spp. Cichorium intybus
Helianthus tuberose Jerusalem artichoke
Seaweed gums
in marine environment flexibility more imp than rigidity:
mainly used for thickening and gelling
huge water holding capacity (1:200), moisten, soften:
Red algae: agar- agar: not assimilated, won’t ferment, non toxic: perfect
bulk laxative adds bulk and hydrates, creating, forms rinse able textures
(toothpastes)
Ex; carrageenan
ex.: chondrus crispus: Irish moss
indications; cough, UTI, bronchitis.
Brown algae; kelp, alginic acid: hemostatic dressing, taken after a meal to
coat gastric mucosa, thickening and binding, anti cancer
Ex: Fucus vesiculosis; Bladderwrack; Alginic acid, most common
used, can bind to strontium in body and chelate it out
Seaweeds
FYI: seaweeds have ability to concentrate heavy
metals and metalloids (ex. Arsenic and
antimony).
Yarnell warns that carrageenan sources are
overharvested, consider the source or use
alternatives.
Lectins: cell communication
Large complicated molecules:
Proteins that bind to sugar residues on membranes
in specific ways for a specific period of time.
They appear to bind with receptors on cell
which then release cytokines
which then affect the activity of other cells.
Cells known to be affected by lectins:
RBC,WBC, spleen, liver, thymus, vascular tissue
immunostimulating: stimulates B and T lymphocytes
antitumor, antineoplastic: monitor growth
allergic response, anaphylaxis: Hemagglutination
Lectins: Potential toxicity
Absorbed intact, esp. in stomach
disruptive though body can stay ahead of the
destruction (usually)
and easily destroyed in cooking as in the case
of Fabacea fam.: Peanut, soybean, lentil,
Canavalia, green beans
That said, susceptible people could experience
overactive response and anaphylaxis.
Lectins: plant sources
they are in all cells, even our own
Plant lectins bind to animal lectins, visa versa
All plasma proteins and enzymes are bound by
some plant lectins or another.
This can activate or inactivate those proteins.
this is toxic or therapeutic
Lectins: some examples
• Avocado lectins block binding of Strep. mutans
to tooth surface: stops decay process
• Tomato lectins bind trypsen and pepsin,
deactivating them. We usually eat them
raw..(bummer)
• Mistletoe stimulates MQ, stim. immune
system, induce CA cell apoptosis (iscador)
• Various lectins are hemaglutenins used in lab
determination of blood types
Carbohydrates: summary
• Mucilages and gums
• Immunostimulating polysaccharides
• Misc
– Pectins
– Fructans
– Lectins
– Seaweed gums
Aromatic Phenols
Aromatic Phenols
Aromatic means containing a benzene ring:
6 carbons that share electrons in a way that
creates a stable ring structure.
Think of the ring as an indivisible building block
Think of there being two levels of building
blocks:
a single ring with different accessories
multiple rings with different accessories
Aromatic phenols:
Fun things to build with phenols
Single rings:
– Simple phenols
Multiple rings:
– Phenlypropanoids
• Flavonoids
• Isoflavonoids
• Tannins
– Hydrolysable
– proanthocyanidins
• Phenolic volatile oils
• Lignans
– Flavinoids
– Isoflavinoids
– Coumarins
– Anthroquinones
Phenols: General Properties
Phenol is the standard for antimicrobials; its effect
is the scale others are judged by.
Bactericidal, antiseptic, antihelmintic
Can be caustic, vesicant and anesthetic
Inhibits WBC activity, like most antimicrobials
It can do this because it’s a small stable molecule , it
reaches tissues intact and then wrecks havoc.
Taste: Bitter
Simple Phenols: examples
Usually not found free in the plant but as
Phenolic Glycosides:
Salicin: Salix spp. willow, viburnum
populous spp. poplar bark.
Populin: Populus
Gaultherin: Gaultheria spp. Wintergreen
Spiraein: Filipendula spp. Meadow sweet
Esters: usually less active and less irritating
Methyl salicylate; Filipendula spp Meadow
sweet, Gaultheria spp.
Salicylaldehyde: Filipendula ulmaria
Salycilates: Function in plant
Antimicrobial: The caustic nature of this weak acid creates
structural damage to cell walls of invaders
Hormonal role:
• In environmental stress conditions signals expression of
genes leading to protective activities.
• Flowering: raises temp in plant right before blooming
which volatilizes fragrances. Also involved in orchestration
of flowering process
• Resistance to and protection from pathogens;
locally at the site of damage
but then quickly through rest of plant
• travels through the plant via phloem
Salycilates: pharmacology
Externally: weak antiseptic, irritant, brings blood flow to area
Internally: pain relief/ anti-inflammatory
strong antipyretic: increases peripheral blood flow, sweat production.
balancing action on thermogenic center of hypothalamus
in pyrexia (elevated temperature) lowers temp
or increases heat to compensate for heat loss through
increased circ.
Cholegogue:
increase volume and concentration bile production
Catabolic: increase protein breakdown
(but not increased disposal through kidneys, problem in gout)
Analgesic:
systemic: depresses CNS,
local: prostaglandin COX2 inhibition (it blocks release of
inflamatory PG)
Phenlypropanoids: role in plant
Antioxidant
in response to biotic or abiotic stresses such as
infections, wounding, UV irradiation, exposure
to ozone, pollutants, and other hostile
environmental conditions
metabolic wastes: are present in parts that are
leaving the plant
Attractants for seed dispersal
Phenylpropanoids; pharmacology
some examples of the complexity
Cafeic acid: in all plants, building block of lignins
Analgesic, anti-inflammatory, promotes intestinal activity
Cynarin: Cynara scolymus globe artichoke
Hepatoprotective, hypercholesterolemia
Curcumin: Curcuma longa turmeric
Anti inflammatory, hypotensive, hepatoprotective
Arbutin; Pyrus communis pear tree, Arctostaphylo uva-ursi
Urinary tract antiseptic, diuretic (hydrolyzes to
hydroquinone)
Eugenol, thymol
Phenolic essential oils
role in plant
• Protection from pathogens and predation
• Antimicrobial, antihelmintic, antifungal
Phenolic essential oil: Eugenol
Found in: Eugenia caryophyllata: clove,
Geum urbanum: cloveroot,
Cinnamomum zelanicum: cinn. (but not C. cassia),
also in bay leaf, nutmeg and allspice
Pharmacology; Anesthetic, antiseptic
external rubeficant, counter irritant
internally: sialagogue, carminative, antispasmodics.
Used
In dentistry for cauterization, disinfectant
In toiletries: toothaches and mouthwashes
Phenolic essential oil: Thymol
Thymus vulgares Thyme
Monarda punctata horsemint
Antifungal, antiseptic, antihelmintic
20X stronger then phenol
Topically needs to be diluted to 1-2%,
thyme EO is 20-30%
Internally is poorly absorbed so best on surfaces
What is absorbed is less mucosally irritating
than phenol.
Phenolic esters
Found in:
celery, aniseed, cloves, basil, tarragon
Safrole; Sassafras albidum, Camphora spp, cocoa,
nutmeg, pepper
char: irritant, toxic
Myristicin; nutmeg and mace, also in black pepper,
carrot, parsley, dill
char: toxic in high doses
Methylchavicol; in oil of basil,
char: skin irritant
Multiple phenol rings
• Tannins
hydrolysable
proanthocyanidins
• Flavonoids
• Isoflavones
• Anthocyanins
• Coumarins
TANNINS: function in plants
Held in storage throughout the plant;
ubiquitous: leaves, buds, roots, seeds, stems
Released and activated when the cells breakdown
Function: irreversibly binds and precipitates out proteins
Astringent;
dries out, contracts tissue, stops leakage of fluid
recreates barrier
Bind surface proteins to harden damaged area
Inhibitory to viruses, bactericidal
Could be metabolic waste of the plant
Tannins: properties
Soluble in alcohol and water
In dilute amounts can form precipitates with
proteins nitrogenous bases, polysaccharides,
some alkaloids, some glycosides
Most are kept to the gut
Therefore useful as antidotes.
Tannins: pharmacology:
only works at point of contact
Treat burns and wounds:
Complex to form a tough protective barrier
Vasoconstrict surface capillaries; hemostatic
Protect from infection and invasion
Reduce swelling and inflammation
Internally: on mucosa orifices
Curdle mucus secretions,
Pucker epithelial tissue and stop more secretion
Anti-inflammatory;
neutralize enzymes, lymph stasis
Antidiarrheal
Tannins: two main types
(usu found in same plant but one is more dominant)
Hydrolysable
simple phenols bound to glucose that are easily split via
acids or enzymes
Ubiquitous, but in small amounts
why tinctures are all brown
Gallic acid, Ellagic acid
Soluble in water
Found in: Geranium maculatum; cranesbill, Agrimony
eupatoria
Tannins: Hydrolysable
pharmacology
Water proofing damaged or inflamed tissue,
reduce swelling
Dry mucous membranes; stops hypersecretion
Prevent mild bleeding, surface vasoconstriction
Reduce uterine bleeding
Binding in gut: antidiarrheal
Antiseptic: antibacterial, antifungal
External use: douche, eyewash, snuff
Tannins: Proanthocyanidins
Condensed ; massive polymers of Flavonoids
Properties: partially soluble in water, alcohol,
but adding glycerite increases solubility
The red insoluble substance found in tinctures
that have been long exposed to light
Function in plants:
Attractant; pollination and seed dispersal
Tannins: Proanthocyanidins: examples
(aka pycnogenols)
Craetagus laaevigata and monogyna hawthorne
Vaccinium myrtillus,(bilberry) V Corybosum (blueberry),
V macrocarpon (cranberry)
Ribes nigrum (black currant)
Vitis vinifera Linne : grapes
Pinus palustra, Pinu maritime
Camillia sinensis (up to 30%)
Hamamelis virginiana
Areca catehu betel nut
Tannins: Proanthocyanidins
general properties
Taste: sour, puckering and astringent
Galenic definition: dry, acts to strengthen
bind, stop fluxes, however, it can spoil
nourishment
Tannins: Proanthocyanidins
medicinal uses
Cardiovascular system:
vasoprotective, antiedema, reduces capillary
permeability, protects vision
antioxidant, inhibits proteolytic enzymes
blocks adhesion of some pathogens in gut and
urinary tract (cranberry)
Tannins: Solubility
Very soluble in water
soluble in glycerin
somewhat in alcohol
Problems:
Discoloration; turn blue black, green black w/ mineral salts
Precipitates: with alkaloids, metals and proteins
create sludge at the bottom of bottle
(dangerous if its an alkaloid)
Solutions:
Glycerin will bind tannins and keep from precipitating
Flavonoids: general properties
3 ring structure that occurs freely or as a
glycoside
Found in most higher plants: not algae
Flavus (Latin) yellow which most are.
Properties:
bitter/sweet, usually as glycosides
Esp in flowers, fruits and leaves
Flavonoids
Role in plants:
plant pigments: yellow, orange, red
color attracts pollinators
or protects plant from insects via toxin
UV protection of the plant
light screens, photosensitization
antioxidants
Flavonoids; pharmacology
Pharmacological:
predominantly on the vascular system
decrease capillary fragility and permeability
stabilizes and calms peripheral circulation
anti-inflammatory, recycles Vit C
diuretic, antispasmodic
antiseptic, antitumor, antiallergy
inhibits enzyme systems
stops destructive processes
Flavonoids: examples
Creataus oxyacantha; Hawthorne, Achillea millefolium:
achillea, Sambusca nigra; elder, Fagopyrum esculentum;
buckwheat, Tilia spp.; Linden, Scutellaria baicalensis and
lateriflora, Gingko biloba, Silybum marianum, Passiflora
incarnata, Thymus vulgares
Specific examples
Rutin; from Ruta graveolens ;
AKA vitamin P ( for permeability factor)
Quercetin
Apigenin
Hesperiden;
Silymarin; protects hepatocytes, induces phase 1 detox,
protects mitochondria form lipid peroxidation, cause
hepatic regeneration
Flavonoids:
a word about vitamin C
Always found with bioflavonoid
always in a fruit acid bioflavonoid complex
Ascorbic acid on its own cannot heal all cases of
scurvy
Flavonoids regenerate spent Vit C
(why we separate them is not logical)
Anthocyanins ; properties
Properties: Pigments found in flowers and fruits:
red, blue, black flowers and fruits
Found as glycosides: as the amount of sugars
and methyl groups increase
color changes from orange to blue
metals and co pigments also change it to blue
Ex; cyanidin, delphinidin
Anthocyanins: role in plant
UV protection
Attractant
Anthocyanins: Pharmacology
Microcirculation: esp. in ophthalmology
Stabilize collagen and protect connective tissue
Anthocyanins: Sources
Vaccinium myrtillus,(bilberry) V Corybosum
(blueberry), V macrocarpon (cranberry)
Ribes nigrum frustus (black current)
Vitis vinifera semen (grape)
Pinus maritma cortex ( maritime pine)
Sambucus nigrum elder berries
Isoflavones
Polyphenol structure only found in Fabacea fam.
role in plant:
antifungal, inhibit pathogen and cause diseased
tissue to die.
attractants for symbiotic rhizobia: in fact w/o them
legumes cannot create nitrogen fixing nodules. Other
plants use flavonoids to do this too.
Isoflavones: Sources
Fabacea fam:
Pueraria montana var lobata kudzu
Medicago sativa alfalfa
Trifolium repens red clover
Glycyrrhiza glabra licorice
Glycine max soy
Isoflavones: pharmacology
Estrogen amphoteric:
weakly binds to estrogen receptors competing
for receptors w/ endogenous hormones
high levels estrogen: lowers the effect
low levels estrogen: increases and supports
effect.
antifungal, antiparasitic?
Coumarins
Phenol with a pyrone ring (ring with O on it)
Has anticoagulant properties mb because it is
similar and competes with vit K, so we don’t
inject or use topically.( it is broken down in the
gut so doesn’t work at anti-coagulant)
Sweet vanilla, clover, fresh mown hay smell used to
make fragrance in perfume industry.
Protective for the plant; works like a pesticide
Found in; lavender, licorice, apricots, cherry,
cinnamon and strawberries, dong quai
Anthroquinone
Properties: bitter, usually found as a glycoside
Uses: dyes, purgatives
Effect in the body: complex;
The bile and gut bacteria split the sugar off;
the aglycone is absorbed and mysteriously
causes the release of prostaglandins which
irritate the bowel smooth muscle increasing
peristalsis.
Anthroquinone
Specific cases; contraindications
Prolonged use leads to decreased tone;
atonicity can be increased
Excessive tension can cause constipation
In that case: tx nervous system not the bowels.
Short term not for extended use
Anthroquinone
Effect of the whole plant or synergistic
friends
can contain tannins too:
Docks and English rhubarb
binding effect allows use in diarrhea
carminatives tone down the spasm of the
Anthroquinones
dill, fennel, aniseed
Anthroquinones: examples
Rubia tinctorum; madder
Cassia angustifolia; senna
Rhamnus frangula; Cascara sagrada
Rhuem palmatum; rhubarb rt
Rumex crispus; yellow dock
Aloe vera; aloes
Volatile Oils
Volatile oils (essential oils)
the life essence
Content of plants can vary from .005% to 10% of
the plant.
Consistency and content change in response to
weather, time, location, community and season.
Volatile oils represent incredible concentration:
To make 1 lb of EO it takes:
50 lbs Eucalyptus, 150 lbs Lavender,
500lbs sage, thyme or rosemary,
2-3,000lbs Rose petals!!!
Volatile Oils: Role in plants
General theme of communication
Attractant or deterrent
Deter insects, pathogens and predators
attracts pollinators or seed dispersal help
Composition can change
with season, time, location
Has a pheromone like quality: it orchestrates
activity around itself and is responsive to the
environment
Volatile oils: examples of role in plants
• Myrhh: exudes a thin cloud around the plant
that protects it from the sun.
• Roots: exude selective pesticides and selective
bacterial attractants creating a preferred safe
biotic community.
• Areal parts: exude selective attractants or
distractants of both insects and microbes and
other competitive plants.
volatile oils: general pharmacology
aromatherapy
EO  olfactory rec.  olfactory lobe Limbic
Limbic system: direct effect on sexual and
emotional behavior and digestion
The limbic system responds to odor the same as
emotions and continues to even after acclimation
to the scent.
How? Presumably at a hormone driven level. EO
can influence emotional states and manipulate
hormone response.
volatile oils: general pharmacology
Antiseptic; lipid solubility allows
Easy entry and disrupt pathogens
Easily travel into all the compartments of the
body
Increase the amount of WBC in the blood
volatile oils: pharmacology
Irritant: by stimulating tissue they contact
they increase circulation; increase capillary flow
or stimulate nerve endings and reflex
increasing salivation, gastric secretions,
appetite
improve peristalsis
expectoration; clearing in stomach wall or
congested lungs
volatile oils: pharmacology
Relaxant; general effect on CNS;
Usually tranquilizing
Antispasmodic; relaxation from the neck down
Mint, European vervain
Volatile oils: general chemistry
Really complex varied group:
Most are colorless (except azulenes: blue)
Most lighter than H2O (except cinnamon)
Don’t become rancid, but do oxidize, vaporize
and resinify when exposed to air and light.
Are soluble in alcohol, lipids, can be steam
distilled
Volatile oil: chemistry
Skeleton of isopropene units linked in chains or
cyclic
Variability comes from the functional groups
attached in different ways to that skeleton and
the 3D structure of the molecule.
Terpine: just the isoprene skeleton, nothing fancy
added
Terpinoid; term for the isoprene skeleton with other
functional groups on it.
Volatile oils: organization based on
functional groups
1.
2.
3.
4.
5.
6.
7.
8.
Hydrocarbons
Alcohol
Aldehyde
Ketone
Phenol
Phenolic ester
Oxide
Ester
Volatile oils: organization
based on isoprene units
• Monoterpanoids: 2 isoprene units
– But also really structurally diverse: cyclic, chains,
enantiomers
– Most common volatile oils
– Responsible for most fragrance and flavor, pungent
• Sesquiterpenoids: 3 isoprene units
– Most common terpenoids in plants
– Most are bitters or have anti- tumor, microbial or are toxic
– Sesquiterpenoid lactones are the main volatile compounds
have a closed ring with Cs and an O and a ketone next to it.
• Triterpenoids: 6 isoprene units: too heavy to be volatile
• Tetraterpanoids: (AKA carotenoids) 8 isoprene units
Volatile oil: general chemistry
Monoterpenoids
Complex: the molecules are constantly shifting
around bonds and each shift is a different
compound. The EO is a constantly changing
slurry of chemical activity.
Plus the functional groups and 3D structural
effect function
Still we can generalize function
(really over generalize, subject of deeper study)
General properties; Monoterpenes
on CNS
Carminative;
Local; reflex on nerve endings in gut, spasmolytic
strengthens, coordinates peristalsis
Central: sedative probably in the hippocampus
(general relay of the whole brain.)
Citronella, citral, limonene,
citronellol, citronellal, geraniol
General properties; Monoterpenes
Topically or through direct action
Antiseptic
Fungicidal , antihelmintic; thymol, ascaridole
(Chenopodium ambrosiodes)
Repel insects; citronella
Rubeficant-stim; menthol, camphor, borneol
Expectorant: cineol (Eucalyptus)
pinene (Angelica archangelica)
borneol (Thymus off.)
Diuretic: dioshenol (Barosma betulina)
terpineol (Juniperus communis)
Volatile oils: Monoterpanoids
pharmacology
Camphor
CNS stimulant, antipuritic, rubeficant, mucolytic
Toxic in high doses
Pipertone; Eucalyptus dives; broad leaf peppermint
Non irritant mucolytic for sinus and bronchitis
Isopinocamphone; oil of hyssop
Mucolytic, muscle relaxant
Thujone, pulegone
Toxic, can induce convulsions,
Mucolytic, esp for respiratory congestion
Volatile Oils: sesquiterpenoid lactones
• Bitters: stimulate GI (more later)
• Irritants:
– Haptens: combines with other molecules to form
antigen
– Can cause dermatitis: messes with enzyme activity
of sulphur containing proteins, can cause
glutathione depletion
SESQUITERPINES; Azulenes
Chamazulene (Matricaria and Achillea)
Guaiazulene (Guaiacum off.)
Extracted;
steam distillation
or hot water infusion
Be careful to capture and collect steam
Properties; azulenes
Anti-inflammatory, antispasmodic
reduce histamine induced reactions
Calm nervous system
Peripherally; viscera
Centrally: HA, anxiety
Mitigates anaphylaxis; allergy, asthma, eczema
Topically antiseptic
Volatile Oils: action in the body
Menthol: Mentha Piperita; peppermint,
cooling, slight anesthetic, reflex vasodilatation
antiseptic, antiparasitic, good for ringworm, carminative esp of
colitis, bowel dz.
can have cumulative irritation of the mucus membranes.
Camphor; Cinnamomum camphora: camphor plant, Artemisia spp,
Chrysanthemum spp (feverfew), Rosmarinus off.
- rubeficant, anti-inflammatory, anesthetic due to cooling
- digestive stim, circulatory stim, dilates coronary arteries and
strengthens heart.
Thujone; Salvia off
-antiseptic, carminative but can be toxic in quantity
-stimulates smooth muscle, estrogenic properties
-small doses calms restores the CNS, visceral antispasmodic
Volatile Oil: toxicity
Chronic toxicity is not well studied
Acute toxicity: really hard to take in enough to be
toxic
Ketones: neurotoxic – epiletiform, tetaniform
episodes, psychic , sensory diturbances
Thujone; thuja, wormwood, tansy, safe
Pinocamhone; Hyssop
Monterpene; high doses camphor, menthol,
cineole. E-anthole
Resins
Resins: function in plant
protection from fungi, insects or wounding
Released during cell breakage
flows out as a liquid, hardens forming a seal.
Antimicrobial, antifungal, antibacterial
Resins: general properties
Amorphous mixture
Acrid and astringent
Insoluble in water, soluble in alcohol and fixed
oils
Heavier than water with high boiling pt
Oleo resin: a resin with volatile oils and gums
Balsam;the aromatic acids: cinnamic and
benzoic acid mixed with resin
Resins: solubility
Soluble in 90% alcohol
Resins: examples
Resins; guaiacum (Guaiacum spp) colophony (Pinus
spp) dragons blood (Daimonrops spp)
Oleo resins: abundant in conifers: turpentine (Pinus
spp) copaiba (Copaifera spp.)mastic ( Pistachia)
Oleo resin gums; myrrh (Commiphora molmol),
frankincense (Boswellia spp) asafetida (ferula
foetida) and gamboges (Garcinia hanburii)
Balsams: balsam of Peru (yroxylon pereiae), balsam
of Tolu (Myroxylon balsamum) and storax
(Liqudambar orientalis) balsam
Resin: pharmacology
Antiseptic as a skin wash for wounds
Stimulates phagocytosis
Intermission