Volatile OilsInternal Use, Chemistry,

Pharmacology, Toxicology

Christopher Hobbs, Ph.D., L.Ac., A.H.G.

Presenter

Essential Oil Therapeutics

Recommended Books

Essential Oils (= volatile oils)

• Complex mixtures

– Green leafy volatiles

– Hydrocarbons (“high notes”)

– Monoterpenes (middle notes, moderately volatile)

• Esters, alcohols, ketones, phenolics

– Sesquiterpenes (low notes, not too volatile)

• Essential oils can contain several hundred identified compounds

• Plant families known for their essential oils include Apiaceae, Lamiaceae, Lauraceae, Myrtaceae, and Asteraceae

Mono-, Sesquiterpenes

Observed Functions in plants

• Protection

– Antifeedants mammals, insects, aphids, etc.

– Allelopathic, Anti microbial, antiviral, antifungal properties

– Seed germination inhibitors

– Seedling inhibitors

– Pheromone mimics to interfere with mating

• Signaling

– plant behavior changes when exposed to airborne volatile compounds on a gradient

Predators cause change in EO composition

Essential Oils

• Complex mixtures of monoterpenes—some essential oils contain several

hundred identified compounds

• Families commonly containing essential oils include the parsley family

(Apiaceae), mint family (Lamiaceae), laurel family (Lauraceae), and the

eucalyptus family

• Essential oils penetrate the skin, are used topically as antiinflammatory and

antimicrobial agents

• Internally as mild sedatives (lemon balm, chamomile), antiinflammatory and

antispasmodics (chamomile, yarrow) and flavor ingredients

• Many more uses as aromatherapy, cosmetics, perfumes, and for internal use,

food and flavor, and medicine

Essential Oil Products

• Oral, Skin Applications

• Addition to tablets, capsules

• Tinctures

• Syrups

• Throat lozenges

• Oral irrigators

• “Cosmedics”—i.e. mouth rinses, shampoos

• Salves, creams

• Medicated fixed oils (SJW oil + lavendar)

Quality

• Distilling oils damage or eliminate “high note” compounds

• Consider a vacuum chamber

• Some commercial products are overheated,

solventextracted (hexane), become much less complex

(GC/MS)

• Some are spiked with synthetics

• Some might contain lipophilic or volatile contaminants

(herbicides)

Quality Issues

• Identity, purity, spiking, analysis, organic

• Safety issues

• Applications

• Materia medica (top 20 oils)

• Setting up a home business

• Resources

Other Quality Issues

• Organically-grown

• Fair trade

• Testing

• Organoleptic (smell, taste)

• The standard is the fresh plant (lavendar, rosemary)

• GC/MS

• LC/MS

• HPLC

Essential Oils—High Variation

• Different population of the same species vary widely in composition—

standardization desirable

• Achenes from 11 indigenous populations of fennel were studied by GC/MS

• Estragole, trans-anethole, fenchone, limonene, and alpha-pinene

• Four different groups were seen

– Hi estragole (63%) and low trans-anethole (3%)

– Estragole (ca. 43% and trans-anethole (ca. 22%)

– Estragole (ca. 23%) and trans anethole (ca. 64%)

– Low estragole (ca. 8%) and high trans-anethole (64%)

• Source: Barazani et al. 1999. Planta Medica 65:486.

Variation—Chemotypes

• Variation—Chemotypes

• Chemotaxonomy

• Variation within a species in different parts of their range

– Hybridization, polyploidy

– Phenotype, genotype

– Predators, browsers (leaf hoppers)

– Manufacturing methods

– Valerian

– Lack of standardization

Basic Metabolic Pathways Secondary Compounds

Four Major Chemical Pathways

Phenyl

Propanoids

Cinnamic acid

Phenolic acids

Quinones

Coumarins

Flavonoids

Anthocyanins

Tannins

Lignin

Terpenes

Alkaloids

Fatty Acids

Isoprene: Basic Building Blocks

Many terpenes are built up from the isoprene or iso-pentane units (C5) linked together in various ways with different ring closures, degrees of unsaturation, and functional groups

Terpenes Built from Isoprenes

• Monoterpenes (C10)

• Sesquiterpenes(C15)

• Diterpenes (C20)

• Triterpenes (C30)

• Carotenoids

• C5 isoprene units

Monoterpenes

• Molecules containing 10 carbon atoms

• Monoterpenes are volatile, slightly water-soluble, more soluble in alcohol

• They are a main constituent of many essential oils

• They can occur as an open chain, single ring, or double ring structure

– Can occur as esters, alcohols, ketones

• Many are aromatic, effect the nervous system, and relax smooth muscle like the bowel; other effects

Sesquiterpenes C15 Compounds

• Sesquiterpenes: C15 compounds

• Component of essential oils

• Examples are the chamazulenes

• About 5,000 have been reported

• Most produced through the mevalonicpathway

• Antispasmodic, antiinflammatory

• Sesquiterpene lactones:

– Over 4,000 reported

– Especially common in Daisy family

• Feverfew (Tanacetumparthenium)

• Yarrow, chamomile

– Tend to be bitter

– Can cause allergic reactions

– Usually crystaline compounds that are not particularly volatile

35.9

0 (E

)-b-O

cim

ene

36.3

5 A

rtem

isia

keto

ne

36.6

8 g-T

erp

inene

36.9

5 tr

ans-

Sabin

ene h

ydra

te

38.0

6 1-N

onen-3

-ol

38.6

0 p-C

ymenene

39.1

0 p-M

enth

a-2

,4(8

)-die

ne

39.3

0 ci

s-S

abin

ene h

ydra

te

39.6

3 Lin

alo

ol

39.8

5 IS

OA

MY

L 2

-ME

TH

YLB

UT

AN

OA

TE

40.1

8 IS

OP

EN

TY

L 2

-ME

TH

YLB

UT

AN

OA

TE

40.4

5 T

hujo

ne

40.5

9 1-O

ct-3

-enyl

ace

tate

40.9

8 tr

ans-

p-M

enth

a-2

,8-d

ienol

41.4

2 (E

)-4,8

-Dim

eth

ylnona-1

,3,7

-triene

42.2

0 C

am

phor

42.3

7 M

enth

a-2

,8-d

ien-1

-ol<

trans-

para

->

43.6

5 P

inoca

rvone

44.5

3 B

orn

eol

44.8

2 Lava

ndulo

l44.8

9 V

irid

ene

45.0

3 tr

ans-

1-P

henyl

-1-p

ente

ne

46.0

8 M

eth

yl s

alic

ylate

46.4

2 a-T

erp

ineol

46.6

7 2-(

2-P

YR

IDY

L)-

3-(

TR

IME

TH

YLS

ILY

L)-

5,6

,7,8

-TE

TR

AH

YD

RO

QU

INO

LIN

E46.9

2 M

yrte

nol 48.4

1 tr

ans-

Carv

eol

49.2

7 ci

s-C

arv

eol

49.6

5 C

arv

one

50.2

0 3-H

EX

EN

YL 2

-ME

TH

YLB

UT

AN

OA

TE

53.7

8 B

orn

yl a

ceta

te

54.1

3 .(

+-)

-LA

VA

ND

ULO

L A

CE

TA

TE

59.4

6 C

ubebene<alp

ha->

59.5

6 C

yclo

hexa

silo

xane, dodeca

meth

yl-

61.3

0 C

opaene<alp

ha->

61.8

2 B

ourb

onene<beta

->

62.0

8 Is

odauca

-4,7

(14)-

die

ne

62.1

5 b-E

lem

ene

62.5

3 C

ubebene<beta

->

64.1

6 Is

oca

ryophyl

lene

64.7

1 b-C

opaene

65.0

1 C

opaene<beta

->

65.4

3 A

rom

adendre

ne

65.7

1 C

adin

a-3

,5-d

iene

66.2

7 H

um

ule

ne<alp

ha->

66.7

7 ci

s-M

uuro

la-4

(15),

5-d

iene

67.6

6 M

uuro

lene<gam

ma->

68.0

0 g-M

uuro

lene

68.3

1 S

elin

ene<beta

->

68.7

1 g-A

morp

hene

68.9

6 B

icyc

logerm

acr

ene

69.1

3 M

uuro

lene<alp

ha->

69.4

1 F

arn

ese

ne<(E

,E)-

alp

ha->

69.5

5 d-A

morp

hene

69.9

4 g-C

adin

ene

70.4

9 d-C

adin

ene

71.0

8 C

adin

a-1

,4-d

iene

72.7

1 G

erm

acr

ene B

40.00 45.00 50.00 55.00 60.00 65.00 70.00

2.0e6

4.0e6

6.0e6

[VULGARIS] TIC #1

Artemisia vulgaris Chromatogram

Sesquiterpenes

Monoterpenes

Higher retention time

Camphor

Isocaryophyllene

GC/MA for Detection and Identification of Terpenes

Gas Chromatogram Diagram

Combi-Pal Autosampler

SPME

Small polymer micro-extraction

Mass Spectrometer

(Text File) Spec 14696 (60.08 min):

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 2200

50

100

39

41

43

51

55

57

65

67

72

79

81

87

91

93

95105

111

121

128

136141

153 167

210

47.3

8 V

erb

enone

47.9

2 B

uta

noic

acid

, 2-m

eth

yl-

4-m

eth

ylp

enty

l este

r48.0

9 tr

ans-P

iperito

l

49.7

5 2,3

-Dehydro

-1,4

-cin

eol

49.8

9 N

era

l

50.4

7 .(

Z)-

3-H

EX

EN

YL IS

OV

ALE

RA

TE

50.6

1 H

exyl 2-m

eth

yl buta

noate

51.4

3 G

era

nio

l

51.6

4 A

scari

dole

51.9

9 G

era

nia

l

52.9

6 tr

ans-S

abin

en h

ydra

te a

ceta

te

53.4

5 C

um

inic

alc

ohol

53.7

1 T

huja

nol aceta

te<

iso-3

->53.8

8 B

orn

yl aceta

te53.9

6 Is

opro

pyl phenyla

ceta

te

54.1

6 tr

ans-S

abin

yl aceta

te

54.6

0 C

arv

acro

l

56.1

0 S

abin

yl aceta

te<

trans->

(A

c v

s.

IPP

)

57.9

0 S

ilphip

erf

ol-5-e

ne

58.0

6 E

ugenol

58.8

1 exo-I

socam

phanyl aceta

te

59.5

1 C

ubebene<

alp

ha->

59.6

1 C

yclo

hexasilo

xane, dodecam

eth

yl

60.0

6 (E

)-Jasm

one

60.3

7 B

enzyl 2-m

eth

ylb

uty

rate

60.4

9 N

ery

l aceta

te

60.7

1 (Z

)-Jasm

one

61.4

6 C

opaene<

alp

ha->

61.6

5 M

odheph-2

-ene 61.9

1 B

ourb

onene<

beta

->

62.1

3 b-C

ubebene

48.00 50.00 52.00 54.00 56.00 58.00 60.00 62.00

0.5e7

1.0e7

1.5e7

[A. douglasiana, 1 hr] TIC #1

Detection, Determination

• Software

– MassFinder 4

– NIST MS search software

– AMDIS

• Databases—Mass Spectral Libraries

– Wiley 8 (399,000 spectra)

– NIST 05 (532,000 spectra)

– Adams, MF4 (about 3,000 spectra (fragrance)

Determining Identity of Peaks

• Two separate experiments

• Retention time is adjusted to an international standard based on lab’s particular GC/MS machines

• Mass spectral data is matched to large databases (> 400,000 compounds)

Spec 14696 (60.08 min): 2-Cyclohexene-1-methanol, 2,6,6-trimethyl-

30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210 220

31

41

41

45

4555

57

59

59

67

69

72

79

81

81

83

8593

93

97

97

105

107

111

121

123

128 136

136

141 153

154

167 210

Is EO chemistry tied to phylogeny?

• Defence compounds, signaling compounds are more tied to

environmental influences

– Differences in EO composition even in the same genus is caused

by gene expression →protein production (enzymes) →terpenes

• Structural compounds (like cellulose, lignin) are more tied

to phylogeny (conserved)

• Nutrition (carbohydrates, proteins, fatty acids)

58.3

9 d-E

lem

ene

59.1

5 S

ilphin

-1-e

ne

59.5

2 C

ubebene<

alp

ha->

59.6

1 C

yclo

hexasilo

xane, dodecam

eth

yl

60.3

6 Is

oborn

yl pro

pio

nate

60.6

8 Is

ole

dene

60.8

6 C

yclo

sativene

61.0

4 Y

langene<

alp

ha->

61.2

2 Longic

ycle

ne

61.3

7 C

opaene<

alp

ha->

61.6

6 M

odheph-2

-ene

61.8

7 B

ourb

onene<

beta

->

62.3

0 E

lem

ene<

beta

->

62.6

1 b-C

ubebene

62.7

5 b-E

lem

ene

63.3

0 b-L

ongip

inene

64.5

0 C

ary

ophylle

ne(E

-)

64.8

2 S

elin

a-3

,6-d

iene

65.0

6 b-C

opaene

65.4

9 A

rom

adendre

ne

65.7

5 C

adin

a-3

,5-d

iene

66.0

2 4aH

,10aH

-Guaia

-1(5

),6-d

iene

66.3

5 H

um

ule

ne<

alp

ha->

66.8

2 cis

-Muuro

la-4

(15),

5-d

iene

67.3

7 A

rom

adendr-

9-e

ne

68.3

4 G

erm

acre

ne D

68.5

2 S

elin

ene<

beta

->68.7

1 B

icyclo

sesquip

hella

ndre

ne

68.8

2 G

erm

acre

ne D

69.0

9 B

icyclo

germ

acre

ne

69.2

7 M

uuro

lene<

alp

ha->

69.5

0 F

arn

esene<

(E,E

)-alp

ha->

69.6

4 d-A

morp

hene

70.0

3 g-C

adin

ene

70.1

9 cis

-Cala

menene

70.3

8 S

elin

ene<

7-e

pi-alp

ha->

70.5

7 d-C

adin

ene

70.6

9 Z

onare

ne

70.9

5 G

uaia

-9,1

1-d

iene

71.1

3 C

adin

a-1

,4-d

iene

71.4

8 C

adin

ene<

alp

ha->

72.0

2 b-C

ary

ophylle

ne o

xid

e

72.5

8 (E

)-N

ero

lidol

73.5

4 4a-H

ydro

xygerm

acra

-1(1

0),

5-d

iene

73.8

4 á-C

AR

YO

PH

YLLE

NE

OX

IDE

75.2

6 C

opaborn

eol

77.2

0 C

ubenol

60.00 62.50 65.00 67.50 70.00 72.50 75.00 77.50

0.5e7

1.0e7

1.5e7

0.5e7

1.0e7

1.5e7

[A. franserioides, 1 hr] TIC #1

[A. douglasiana, 1 hr] TIC #2

Germacrene DCaryophyllene

A. franserioides

A. douglasiana

Both taxa from the vulgaris clade

59.1

0 P

resilp

hip

erf

ol-

7-e

ne

59.4

8 C

ubebene<

alp

ha->

60.7

1 C

lovene

61.0

0 Y

langene<

alp

ha->

61.3

5 C

opaene<

alp

ha->

61.5

9 M

odheph-2

-ene

61.8

3 B

ourb

onene<

beta

->62.0

0 Is

ole

dene

62.0

8 b-C

ubebene

62.5

5 C

ubebene<

beta

->

63.2

7 Is

ocom

ene<

beta

->

63.6

5 Italic

ene

64.1

2 C

ary

ophylle

ne(E

-)

64.3

3 O

pposita-4

(15),

11-d

iene

64.7

4 S

elin

a-3

,6-d

iene

65.0

2 b-C

opaene

65.2

1 B

erg

am

ote

ne<

alp

ha-t

rans->

65.4

5 A

rom

adendre

ne

65.7

4 C

ala

rene

65.9

8 C

adin

a-3

,5-d

iene

66.1

6 S

elin

a-4

(15),

6-d

iene

66.2

8 H

um

ule

ne<

alp

ha->

66.4

6 S

elin

a-4

(15),

7-d

iene

66.8

0 cis

-Muuro

la-4

(15),

5-d

iene

67.3

6 4,5

-di-

epi-A

risto

lochene

67.6

2 C

adin

a-1

(6),

4-d

iene<

trans->

67.8

2 g-M

uuro

lene

68.1

8 G

erm

acre

ne D

68.5

3 S

elin

ene<

beta

->

68.7

5 M

uuro

lene<

gam

ma->

69.0

2 B

icyclo

germ

acre

ne

69.1

6 M

uuro

lene<

alp

ha->

69.5

8 d-A

morp

hene

70.0

0 g-C

adin

ene

70.1

6 cis

-Cala

menene

70.5

6 d-C

adin

ene

70.6

8 Z

onare

ne

71.1

1 C

adin

a-1

,4-d

iene

71.4

7 C

adin

ene<

alp

ha->

58.00 60.00 62.00 64.00 66.00 68.00 70.00

0.5e7

1.0e7

1.5e7

0.5e7

1.0e7

1.5e7

[CH5-25B] TIC #1

[CHINEN3] TIC #2

A. chinensis

A. mauiensis

60.4

0 Is

oborn

yl pro

pio

nate

60.6

1 N

ery

l aceta

te

60.9

0 C

yclo

sativene

61.0

8 C

yclo

sativene

61.4

1 C

opaene<

alp

ha->

61.9

0 B

ourb

onene<

beta

->

62.1

2 a-F

unebre

ne

62.6

1 b-C

ubebene

63.2

0 Italic

ene

63.6

5 cis

-a-B

erg

am

ote

ne

64.2

2 C

ary

ophylle

ne(E

-)

64.7

8 C

opaene<

beta

->

65.0

6 b-C

opaene

65.2

4 B

erg

am

ote

ne<

alp

ha-t

rans->

65.4

7 S

esquis

abin

ene A

65.7

6 C

adin

a-3

,5-d

iene

66.0

4 4aH

,10aH

-Guaia

-1(5

),6-d

iene

66.3

2 H

um

ule

ne<

alp

ha->

66.5

9 N

ery

lpro

pio

nate

66.8

1 C

adin

a-1

(6),

4-d

iene<

cis

->

67.3

7 4,5

-di-

epi-A

risto

lochene

67.7

9 N

eocalli

tropsene<

alp

ha->

67.9

7 C

urc

um

ene<

gam

ma->

68.2

1 G

erm

acre

ne D

68.4

3 A

morp

ha-4

,7(1

1)-

die

ne

68.7

9 Z

ingib

ere

ne<

alp

ha->

69.0

5 B

icyclo

germ

acre

ne

69.1

7 M

uuro

lene<

alp

ha->

69.3

5 (Z

)-a-B

isabole

ne

69.6

0 d-A

morp

hene

69.7

8 b-C

urc

um

ene

69.9

9 g-C

adin

ene

70.3

4 C

adin

ene<

gam

ma->

70.5

3 d-C

adin

ene

71.1

2 C

adin

a-1

,4-d

iene

71.4

7 C

adin

ene<

alp

ha->

73.8

4 á-C

AR

YO

PH

YLLE

NE

OX

IDE

60.00 62.00 64.00 66.00 68.00 70.00 72.00 74.00

0.5e7

1.0e7

1.5e7

2.0e7

2.5e7

0.5e7

1.0e7

1.5e7

2.0e7

2.5e7

[A_CALIF1] TIC #1

[CHINEN3] TIC #2

A. chinensis

A. californica

• Essential oils penetrate the skin, enter the circulation

• Topically as antiinflammatory and antimicrobial agents

• Locally-active for relieving pain and stagnation of injuries, neuropathies

• Internally as mild sedatives (lemon balm, chamomile)

• Antiinflammatory and antispasmodics (chamomile, yarrow)

• Flavor, aroma ingredients for foods and drink (orange, cinnamon, mint)

Commercial Uses

Other Human Value of Volatile Oils

• Antiseptic properties of volatile oils known since antiquity

• Thyme, sage, hyssop, basil, rosemary, ginger all have strong anti-microbial

properties, used in cooking, preserves meats

• Enbalming proceedures

• Impart flavor, aroma to food, drinks

• “Aromatherapy”

Pharmacological Effects

• Stabilizes mast cells, reducing histamine (pro-

inflammatory) release

• Smooth muscle relaxant (trachea, intestine, bronchi)

• Strong inhibitor of TNF-alpha, IL-beta, some effect on

chemotactic cytokines

• Reduces inflammation

• Sedative

• Antimicrobial

Safety of Essential Oils

• Dilute in fixed oil if irritation occurs on skin (2-3 drops/ml)

• Check for sensitivity

• Keep out of reach of children, use safety caps

• Be aware of potentially toxic oils

• Pennyroyal, wormwood, mugwort, sage

• Caution in children under 6 years of age

• Skin sensitivity with sun exposure

• Bergamot, grapefruit, angelica

• Don’t use near the eyes or put into ears

• High phenolic oils can irritate the eyes—oregano, thyme, clove, helichrysum

• Caution during pregnancy, especially oils with putative hormone-like activity—clary sage,

sage, tansy, juniper, fennel

Potentially Toxic Oils

• Boldo--ascaridole

• Camphor—stimulates nervous system

• Mugwort (and other Artemisia spp.)

• Pennyroyal—abortifaciant

• Rue—allelopathic (ketones)

• Sage (Salvia spp.)--thujone

• Star Aniseed (Illicium)--anethole

• Thuja—contains thujone

• Wintergreen—methyl salicylate

• Wormseed—highly toxic (ascaridole)

• Wormwood (other Artemisia spp.)—contains thujone

Estrogenic Effects

• Geraniol, nerol and trans-anethole show some activity in high concentrations

• Eugenol—antiestrogenic activity

• Anethole has definite estrogenic activity, also antifertility activity; appears to

be safe

• 80-90% in Pimpinella anisum and Illicium verum (star anise) and 50-60% in

fennel seed oil

• Estrogenic effects of oils not due to anethole alone

Estragole—Suspected Carcinogen

• Some varieties of fennel

• Much lower

• Basil

• Tarragon (Artemisia dracunculus)

• Very low

• Hyssop

Internal Use

Whole Life Oils

Diluting Essential Oils

Source: Johnson: EBEOT

Irritation from Oral Ingestion of EO

• “Based on current knowledge, and the available literature,

oral administration of essential oils does not pose a long-

term risk of damage to the oral cavity, esophagus, stomach,

or intestines when taken in reasonable dosages and with

food.”

• Some EO can have an antiinflammatory, healing effect on

mucous membranes (i.e. orange, turmeric, ginger)

• For review of the relevant literature:

• Johnson, Dr. Scott A.. Evidence-Based Essential Oil Therapy: The Ultimate Guide to the Therapeutic and Clinical Application of

Essential Oils (Kindle Locations 1191-1192). Scott A. Johnson Professional Writing Services, LLC. Kindle Edition.

Absorption

• 1-2 drops of EO swished in the mouth for oral health

– Lavender, peppermint, orange oil, lemon oil, etc.

• For treating esophagus or bronchial area, add 1-2 drops to

honey

• For delivery to the stomach (H. pylori, gastritis, etc.), add

1-2 drops to gel caps

• For delivery to the LI, SI, add to carrier oil (avocado, olive,

etc.)

Essential Oils in Tablets, Capsules

• Enhancing medicinal effects (try Counter Attack)

• Sensory appeal—flavor, smell, “compliance”

• Orange, peppermint

• Antibacterial, antifungal, antiviral effects

• Oregano, thyme, tea tree

• Digestive, “Qi-regulating” effects

• Ginger, peppermint, caraway, fennel (help prevent indigestion from dietary

supplements—most common side effect)

• Antispasmodic, antiinflammatory effects

• Chamomile, yarrow

• Sedative, calming effects

• Valerian, orange, lemon balm

Antibacterial, Antifungal

• Add to products to treat infections

• Respiratory tract

• Urinary tract

• Apply to soles of feet, in syrups

• Tablets, capsules, teas (Good Earth Cinnamon tea)

• Vaginitis, cystitis, colds, flu, bronchitis,

• Sinusitis

Digestive Aids

• Antispasmodic essential oils for relieving pain, gas,

discomfort of overeating, dyspepsia

• For liver products—i.e. liver Qi stagnation

• “free and easy wanderer” (Bupleurum spp. has EO)

– get it in teas but not extractions?—volatiles lost

• For flavoring laxatives, liver products

• Gas—”4 Seed Tea”

– fennel, fenugreek, flax, caraway

Sedatives, Calmatives

• Anxiety, nervousness

• Insomnia

– Lemon balm

– Valerian

– Lavender (high linalool)

– Fleabane (high linalool)

Antispasmodic, Antiinflammatory

• Intestinal cramps, pain, distension

• Bronchial spasms, inflammation

• Sinus inflammation

• Uterine cramps

External Products

Cosmetics

• Perfumes—essential oil blends

• Deodorants—sage

• Creams

• Salves

• Bath salts

• Shampoo and Cream Rinse

Carriers

• Small, highly lipophilic molecules

• Carry other larger or more hydrophilic compounds into the

dermis and the capillary system via the blood and lymph

• Excellent for treating local areas

• Pain, spasms, infections, trauma

• Delivery of larger compounds like

• triterpenes (steroids)

• Essential oils can carry green tea polyphenols—sun protection

Treating Infections

• Add to creams, salves

• Apply diluted—2-4 drops / tsp (1 ml)

• Apply some undiluted (caution)

• Some people develop sensitivity

• Can erode dermis—highly irritating

• Ketones like Thyme oil

• Oregano, thyme, manuka, tea tree oil most active

Treating Pain, Inflammation

• Inflammation (azulenes)

• Chamomile, yarrow, mugwort

• High chamazulene variety of Artemisia arborescens

– (up to 40%), low thujone

• Pain

• Everlasting (Helichrysum italicum)

• Roman chamomile

• Blood-movers (ginger, cinnamon)

• Methyl salicylate: wintergreen, cherry birch, Polygala spp., Ceanothus spp.,

Cercocarpus spp.

Mint Family Lamiaceae

• Many medicinal genera

– Rosmarinus, Salvia, Thymus, Mentha, Origanum, Scutellaria, Lavandula

• Opposite leaves, bilabiate flowers, aromatic herbs

• Over 200 compounds identified from the essential oil of lavender

Apiaceae

• Parsley Family (formerly Umbelliferae)

– Fennel seed

– Angelica spp.

– Lovage (Ligusticum spp.)

– Desert parsley (Lomatium spp.)

– Parsley seed, root

Laurel Family Lauraceae

• Mainly tropical

family

• Several important

commercial trees

– Cinnamon,

camphor, bay tree

Thujone: Mutagenic, Hepatotoxic

• Neurotoxic, hepatotoxic, mutagenic in animal tests, bacterial assays

• Found in Salvia, Artemisia (wormwood, mugwort)

• Not particularly water soluble, so a traditional tea of wormwood is safer than alcoholic tincture

• One active ingredient of the hallucinogenic drink, absinthe

Valerian Valeriana spp.

• Monoterpenes are important part of activity

– isovaleric acid, 3-methylvaleric acid, limonene, etc.

– “Valerian monoterpenes produce unprecedented enhancememnt of GABA action at GABA A receptors” (Johnson, 2004)

• The valepotriates (C15) are known as antidepressant anxiolytics in Germany, where valerian extracts are commonly prescribed by doctors

• Fairly unstable, which partly accounts for the uneven quality of valerian products

• Mutagenic in some assays, but poorly absorbed and breakdown products are not mutagenic, but still active

Sesquiterpenes C15 Compounds

• Sesquiterpenes: C15 compounds

• Component of essential oils

• Examples are the chamazulenes

• About 5,000 have been reported

• Most produced through the mevalonicpathway

• Antispasmodic, antiinflammatory

• Sesquiterpene lactones:

– Over 4,000 reported

– Especially common in Daisy family

• Feverfew (Tanacetumparthenium)

• Yarrow, chamomile

– Tend to be bitter

– Can cause allergic reactions

– Usually crystaline compounds that are not particularly volatile

Chamomile

• German chamomile is Matricaria

recutita L.

• Roman chamomile is

Chamamaelum nobile L.

• Both contain monocyclic

sesquiterpenes such as bisabolol,

bicyclic sesquiterpenes such as

chamazulene

• Used traditionally for painful

digestion, cramps;

antiinflammatory skin

preparations

• Safe during pregnancy and

nursing

• Traditional teas are active, but ethanolic extracts are more potent

Essential oils

• Essential oils are volatile, b.p. 130-180 f

• Contain esters, monoterpenes, sesquiterpenes

• Families: Lamiaceae, Apiaceae, Rutaceae, Lauraceae, Myrtaceae

• Potent plants containing essential oils: Thymus, Eucalyptus, Salvia, Rosmarinus

Essential oils also have

antimicrobial, sedative,

antiinflammatory effects, among

others

Production

Essential Oil Production

• Enfleurage (flower extraction

with cold fat)

• Steam distillation

• Solvent extraction

Materia Medica—Top 20

• Oregano, thyme (antimicrobial)

• Tea tree (antimicrobial)

• Ginger (analgesic, blood mover)

• Lemon balm (calmative, sleep aid)

• Valerian (sedative, sleep aid)

• Chamomile (blue) (antiinflammatory)

• Mugwort (ext. only-antiinflammatory)

• Orange (calmative, flavor enhancer)

• Cinnamon (blood mover, pectoral)

• Wintergreen (external) (analgesic)

• Yerba santa (expectorant)

• Eucalyptus (antihistamine)

• Helichrysum (antihistamine, skin)

• Clove (analgesic, antimicrobial)

• Lavendar (relaxant, calmative)

• Rosemary (energizer, antioxidant)

• Juniper (antimicrobial, diuretic)

• Pine (expectorant, mucolytic, antiseptic)

• Cedar (antimicrobial, antiviral)

• Fennel (carminative, digestive aid)

Rosemary

Rosmarinus officinalis

• Native of Mediterranean area

• Essential oil contains mainly camphor; 1,8-cineol, pinene

• Besides antibacterial effects, effective against Candida albicans, and also a good blood-mover (emmenagogue)

• Also mild nervous system stimulant (camphor), antiinflammatory

• Dose: up to 10 drops/day (diluted)

Thyme and Thymol

• Effective against a wide variety of

pathogenic bacteria and fungi,

especially S. aureus, Vibrio

parahaemolyticus, Salmonella

typhimurium, etc.

• Effective against C. albicans,

Tinea spp., Aspergillus spp.

• Dilute 1:10 in olive oil for

external use; or use 1:5 tincture of

recently-dried herb

• Can cause skin irritation

• Toxic internally

Int J Food Microbiol 3:349; 1986. Appl. Environ. Microbiol 39:818; 1980

Oregano, Thyme Oils

• Thyme—1.0 – 2.5% volatile oil; minimum 40% should be

thymol + carvacrol (Ph. Eur.)

• Oregano—thymol (0-21%); carvacrol (0-85%) Quality!

• Quality—synthetic oils vs. natural oils (GC/MS); natural more

complex

• Both more effective than either alone

• Carvacrol + thymol less effective than whole oil in vivo

• Action: damage in membrane integrity, which further affects

pH homeostasis and equilibrium of inorganic ions

• Strong antioxidant properties of oil + phenolics (rosmarinic

acid, etc.)

• Dose: 1-2 drops in tea; gum irrigator; 0.2-0.4 ml enteric

Thyme

• Spasmolytic, antimicrobial,

expectorant

• Bronchitis, colds, pneumonia

• Coughs in syrups,

mouthwashes, toothpastes

• Easily toxic with overdose

• 1-2 drops in syrup or lozenges;

tincture, 10-25 drops several

times daily; tea, ½ tsp dried

herb/cup (infusion)

• As a tea, tincture for worms

Oregano

• Oreganum vulgare

• Often contains more thymol,

carvacrol than thyme

• Quality varies widely

• Commercial oils often synthetic

• Commercial products often

diluted with fixed oils

Eucalyptus globulus

Eucalyptus oil

• E. globulus native to Tasmania,

widely planted as wind breaks, etc.

• Essential oil contains about 85%

1,8-cineol

• Essential oil and 1-8-cineol has

proven antibacterial activity(E. coli,

Streptococcus, Mycobacterium, etc.)

• Also antiinflammatory

(prostaglandin-inhibitory),

antisecretory, expectorant

• Dose: 1-3 drops (diluted) or in steam

Eucalyptus

• Effective for helping to relieve symptoms

• Colds, flu, sinusitis

• Decongestant (mast cell stabilizer)

• Use in inhalers, 1-2 drops /ml in tinctures

• Candies, syrups

• Mouthwashes

Essential Oils in Dentistry

• Study found that manuka, tea tree, or eucalyptus oils were

bacteriocidal for a variety of oral pathogens

• Effective at 0.2%, exposure of 30 seconds

• No cytotoxicity was found

• Applications in oral irrigators

• Takarada et al, 2004

Myrtaceous Oils

• Members of the Myrtaceae

• Eucalyptus, cajeput,

• manuka, kanuka, niaouli, tea

tree

• All oils are active, especially

against gram positive bacteria

• Manuka and tea tree oils may be

most potent (Harkenthal et al,

1999)

Mint Family Lamiaceae

• Many medicinal genera

– Rosmarinus, Salvia,

Thymus, Mentha,

Origanum, Scutellaria,

Lavandula

• Over 200 compounds

identified from the

essential oil of lavender

Apiaceae

• Parsley Family (formerly Umbelliferae)

– Fennel seed

– Angelica spp.

– Lovage (Ligusticum spp.)

– Desert parsley (Lomatium spp.)

– Parsley seed, root

Laurel Family Lauraceae

• Mainly tropical family

• Several important commercial trees– Cinnamon

– Camphor

– Bay tree

Thujone: Mutagenic, Hepatotoxic

• Neurotoxic, hepatotoxic, mutagenic in animal tests, bacterial assays

• Found in Salvia, Artemisia (wormwood, mugwort)

• Not particularly water soluble, so a traditional tea of wormwood is safer than alcoholic tincture

• One active ingredient of the hallucinogenic drink, absinthe

Valerian Valeriana spp.

• Volatile terpenes are known

as antidepressant anxiolytics

in Germany, where valerian

extracts are commonly

prescribed by doctors

• Valerenone, valeric acid, etc.

are active sedative

compounds

• GABA A receptor agonist

Chamomile Sesquiterpenes

• German chamomile is Matricaria recutita L.

• Roman chamomile is Chamamaelum nobile L.

• Both contain monocyclic sesquiterpenes such as bisabolol, bicyclicsesquiterpenes such as chamazulene

• Used traditionally for painful digestion, cramps; antiinflammatory skin preparations

• Safe during pregnancy and nursing

Traditional teas are active, but ethanolic extracts are more potent

Plants produce monoterpene glycosides

• The group of Croteau (1988) found that monoterpenes can

be converted to water-soluble glycosides, that may be

freely transported throughout the plant, for instance the

rhizomes or roots

• Roots produce volatile terpenes, significant in root-

rhizosphere interactions (Flores et al, 1999)

Resources

• Simpler’s Botanical Company

– 1 800 652-7646 Sebastapol, CA

• Original Swiss Aromatics

– 1 415 459-3998

• Pacific Institute of Aromatherapy

– 1 415 479-9120

• Oak Valley Herb Farm (Kathi Keville)

– 1 530 265-9552