Plant ConstituentsPart I

School of Traditional Western HerbalismMay 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 earthEach has hundreds to thousands different unique chemicalsIndividual plants in different situations produce unique chemical ProfilesAny 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 constituentsBecome aware of the patterns of different

constituents in the whole plantStart to recognize the emerging logic and

personality of the plantApply 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 chemistrysee Handout

Botanical production of herbal constituentssee Handout

Carbohydrates: Polysaccharides

Carbohydrates: Polysaccharides

Definitionhuge 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 alcoholSoluble in water• mucilages form long slimy chains: less water

soluble• Gums are branched chains creating a matrix

or tacky gel: absorb more water

Pharmacology: MucilagesLOCAL:• 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 mucilageGumsAcacia spp. :Gum Arabic; very water soluble, makes a soothing syrup and effective emulsifier.Is digested and absorbed but nontoxicProsopis spp. :Mesquite GumPrunus spp. : Cherry gum

Mucilages Linum spp; Flax seedPlantago spp. : Psyllium seedUlmus fulva: slippery elm barkSymphytum 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 polysaccharidesthe 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 system1. 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 mouth4. (cell wall) Chelates out cadmium, pesticides, PCBs5. 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: Rieshiincreases 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 Polysaccharidestheories 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

FructansSoluble in hot water, it’s a storage form of polymers of fructose

Inulin: main one used in phytotherapynot digested passes to GI unchanged

increases renal flowstabilizes blood sugarDiureticImmunostimulating

Found in: Poaceae: grass fam, Liliacease: lily fam, Asteraceae

Arctium lappa, Inula helenium Cynara scolymus Taraxicum off. Echinacea spp. Cichorium intybusHelianthus tuberose Jerusalem artichoke

Seaweed gumsin 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 cancerEx: 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 communicationLarge complicated molecules:

Proteins that bind to sugar residues on membranesin 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 lymphocytesantitumor, antineoplastic: monitor growthallergic response, anaphylaxis: Hemagglutination

Lectins: Potential toxicity

Absorbed intact, esp. in stomachdisruptive 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 sourcesthey are in all cells, even our own

Plant lectins bind to animal lectins, visa versaAll 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 blockThink 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, antihelminticCan be caustic, vesicant and anestheticInhibits WBC activity, like most antimicrobialsIt can do this because it’s a small stable molecule ,

it reaches tissues intact and then wrecks havoc.Taste: Bitter

Simple Phenols: examplesUsually not found free in the plant but as Phenolic Glycosides:

Salicin: Salix spp. willow, viburnumpopulous spp. poplar bark.

Populin: PopulusGaultherin: Gaultheria spp. WintergreenSpiraein: Filipendula spp. Meadow sweet

Esters: usually less active and less irritatingMethyl 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: pharmacologyExternally: weak antiseptic, irritant, brings blood flow to areaInternally: pain relief/ anti-inflammatory strong antipyretic: increases peripheral blood flow, sweat production. balancing action on thermogenic center of hypothalamus

in pyrexia (elevated temperature) lowers tempor 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

Antioxidantin 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; pharmacologysome 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 oilsrole 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 irritantinternally: sialagogue, carminative, antispasmodics.

UsedIn dentistry for cauterization, disinfectantIn toiletries: toothaches and mouthwashes

Phenolic essential oil: ThymolThymus vulgares Thyme Monarda punctata horsemint

Antifungal, antiseptic, antihelmintic20X stronger then phenol

Topically needs to be diluted to 1-2%, thyme EO is 20-30%

Internally is poorly absorbed so best on surfacesWhat 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, toxicMyristicin; nutmeg and mace, also in black pepper, carrot,

parsley, dillchar: toxic in high doses

Methylchavicol; in oil of basil,char: skin irritant

Multiple phenol rings

• Tanninshydrolysableproanthocyanidins

• 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 breakdownFunction: 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: propertiesSoluble in alcohol and waterIn dilute amounts can form precipitates with proteins nitrogenous bases, polysaccharides, some alkaloids, some glycosides Most are kept to the gutTherefore 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; hemostaticProtect from infection and invasion

Reduce swelling and inflammationInternally: on mucosa orifices

Curdle mucus secretions,Pucker epithelial tissue and stop more secretionAnti-inflammatory;

neutralize enzymes, lymph stasisAntidiarrheal

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 enzymesUbiquitous, but in small amountswhy tinctures are all brownGallic acid, Ellagic acidSoluble in water

Found in: Geranium maculatum; cranesbill, Agrimony eupatoria

Tannins: Hydrolysablepharmacology

Water proofing damaged or inflamed tissue, reduce swelling

Dry mucous membranes; stops hypersecretionPrevent mild bleeding, surface vasoconstrictionReduce uterine bleedingBinding in gut: antidiarrheal Antiseptic: antibacterial, antifungalExternal use: douche, eyewash, snuff

Tannins: Proanthocyanidins

Condensed ; massive polymers of Flavonoids Properties: partially soluble in water, alcohol,

but adding glycerite increases solubilityThe 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 hawthorneVaccinium myrtillus,(bilberry) V Corybosum (blueberry), V

macrocarpon (cranberry)Ribes nigrum (black currant)Vitis vinifera Linne : grapesPinus palustra, Pinu maritimeCamillia sinensis (up to 30%)Hamamelis virginiana Areca catehu betel nut

Tannins: Proanthocyanidinsgeneral properties

Taste: sour, puckering and astringentGalenic definition: dry, acts to strengthen

bind, stop fluxes, however, it can spoil nourishment

Tannins: Proanthocyanidinsmedicinal uses

Cardiovascular system:vasoprotective, antiedema, reduces capillary permeability, protects visionantioxidant, inhibits proteolytic enzymesblocks adhesion of some pathogens in gut and urinary tract (cranberry)

Tannins: SolubilityVery soluble in water soluble in glycerinsomewhat in alcohol

Problems: Discoloration; turn blue black, green black w/ mineral saltsPrecipitates: 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 algaeFlavus (Latin) yellow which most are.Properties:

bitter/sweet, usually as glycosidesEsp in flowers, fruits and leaves

FlavonoidsRole in plants:

plant pigments: yellow, orange, redcolor attracts pollinatorsor protects plant from insects via toxin

UV protection of the plantlight screens, photosensitization

antioxidants

Flavonoids; pharmacology

Pharmacological:predominantly on the vascular system

decrease capillary fragility and permeabilitystabilizes and calms peripheral circulation

anti-inflammatory, recycles Vit Cdiuretic, antispasmodicantiseptic, antitumor, antiallergyinhibits enzyme systems

stops destructive processes

Flavonoids: examplesCreataus 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 examplesRutin; from Ruta graveolens ;

AKA vitamin P ( for permeability factor)QuercetinApigeninHesperiden;

Silymarin; protects hepatocytes, induces phase 1 detox, protects mitochondria form lipid peroxidation, cause hepatic regeneration

Flavonoids: a word about vitamin C

Always found with bioflavonoidalways 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 protectionAttractant

Anthocyanins: Pharmacology

Microcirculation: esp. in ophthalmologyStabilize 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 kudzuMedicago sativa alfalfaTrifolium repens red cloverGlycyrrhiza glabra licoriceGlycine max soy

Isoflavones: pharmacology

Estrogen amphoteric:weakly binds to estrogen receptors competing for

receptors w/ endogenous hormoneshigh levels estrogen: lowers the effectlow 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 pesticideFound in; lavender, licorice, apricots, cherry, cinnamon

and strawberries, dong quai

Anthroquinone

Properties: bitter, usually found as a glycosideUses: dyes, purgativesEffect 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; contraindicationsProlonged 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

AnthroquinoneEffect 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 sagradaRhuem palmatum; rhubarb rtRumex 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 communicationAttractant or deterrent

Deter insects, pathogens and predatorsattracts pollinators or seed dispersal helpComposition 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 pharmacologyaromatherapy

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 allowsEasy entry and disrupt pathogensEasily travel into all the compartments of the bodyIncrease the amount of WBC in the blood

volatile oils: pharmacology

Irritant: by stimulating tissue they contact they increase circulation; increase capillary flowor stimulate nerve endings and reflex

increasing salivation, gastric secretions, appetiteimprove peristalsis

expectoration; clearing in stomach wall or congested lungs

volatile oils: pharmacology

Relaxant; general effect on CNS;Usually tranquilizingAntispasmodic; 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 cyclicVariability 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. Hydrocarbons2. Alcohol3. Aldehyde4. Ketone5. Phenol6. Phenolic ester7. Oxide8. 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 chemistryMonoterpenoids

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; Monoterpeneson CNS

Carminative; Local; reflex on nerve endings in gut, spasmolytic

strengthens, coordinates peristalsisCentral: sedative probably in the hippocampus

(general relay of the whole brain.)

Citronella, citral, limonene, citronellol, citronellal, geraniol

General properties; MonoterpenesTopically or through direct action

Antiseptic Fungicidal , antihelmintic; thymol, ascaridole

(Chenopodium ambrosiodes)Repel insects; citronellaRubeficant-stim; menthol, camphor, borneolExpectorant: 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 hyssopMucolytic, 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 infusionBe careful to capture and collect steam

Properties; azulenes

Anti-inflammatory, antispasmodicreduce histamine induced reactions

Calm nervous systemPeripherally; viscera

Centrally: HA, anxietyMitigates anaphylaxis; allergy, asthma, eczema

Topically antiseptic

Volatile Oils: action in the bodyMenthol: 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 studiedAcute toxicity: really hard to take in enough to be

toxic Ketones: neurotoxic – epiletiform, tetaniform

episodes, psychic , sensory diturbances Thujone; thuja, wormwood, tansy, safe

Pinocamhone; HyssopMonterpene; high doses camphor, menthol, cineole. E-anthole

Resins

Resins: function in plant

protection from fungi, insects or woundingReleased during cell breakage flows out as a liquid, hardens forming a seal.

Antimicrobial, antifungal, antibacterial

Resins: general properties

Amorphous mixtureAcrid and astringentInsoluble in water, soluble in alcohol and fixed oilsHeavier than water with high boiling ptOleo resin: a resin with volatile oils and gumsBalsam;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 woundsStimulates phagocytosis

Intermission