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Transcript of Internal Use, Chemistry, Pharmacology, Toxicology€¦ · · 2016-09-10lab’s particular GC/MS...
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