Download plants

Contact with new cultures changed the drinking, eating, recreational habits of Europeans
From Asia came tea, from Africa (Arabia) coffee and from America (Holland) cacao
While beer is the unrefined drink of primitive, happy people, distillation was learned from
the Moors ( Al Cohol). With it came alcoholism, addiction; then smoking, tobacco,
gold and syphilis from America. Crusading is a bad idea, isolationism is good.
The 3 temptations of foreign lands: alcohol + coffee
(moor), tea + opium (asian) + smoking (american)
Medically active substances in Plants
Although medical action of plants like Aloe was known already to Cleopatra. However, the
reduction of the effect to one or a few substances adds to our understanding of larger connection
Anthraquinones: contract gut muscle
also important red pigments
Rheum, Cassia senna,
Aloe, Rhamnus
Mucilage: protect sensitive mucous
membranes in throat, stomach & guts
Ulmus, Linum usit.,
Verbascum, Tussilago
Anthocyanins: important pigments,
UV protectants & antioxidants
Rubus, Vaccinium,
Vitus vinifera
Fagopyrum (rutin),
Vacc. leaves, lemon p
Quercus, Vitus vin.,
Rhus, Acacia catechu
Flavonoids: antioxidants, UV protect,
antioxidants anti-inflamm, capillaries
Tannins: antibacterial, antifeedants,
bind with proteins & alkaloids
Coumarins: Blood thinner (anticoag.),
relaxant, furanoco are photosensitizers
Glucosinolates: skin inflammants,
increase cap. Blood flow, red. Thymus
Apium grav., Gallium
Mellilotus off., Ammi
Rhaphanus (reddish),
Sinapis a, Brassica ni
Medically active substances in Plants
Plants are the biochemically most versatile & advanced kingdom of life, followed by fungi ….
Vitamines: Compound (also ess AA
& FA) that cannot be prod. by humans
Essential oils/ Terpenes/Resins:olfact
perception coupled with emot memory
Nasturtium off (Vit E)
Rosa can hips (Vit C)
Melaleuca tee tree,
Draceana, Thymus
Cardiac Glycosides: off toxin
Cyanogenic Glycosides: in low doses
relaxant (cough), higher cyanide
Digitalis Maianthenu
Alkaloids: multiple inc narcotic action
Bitters: Di- & triterpenes, alkaloids
stimulate digestion
Solanaceae, Asterace
Artemisia, Achillea,
Gentium, Humulus
Fiber: polymeric substances that
accelerate passage through GI tract
Avena, Platanum,
Malus,
Saponins: Triterpene sapogenines +
steroid s., hormonal, hemolytic action
Glycyrrhiza,Solanum
tubers, Saponaria
Prunus serotina
Sambucus, Linum usi
… we might fairly gauge the future of biological sciences, centuries
ahead by estimating the time it will take to reach a complete
comprehensive understanding of odor
Lewis Thomas
The chemical concept:
enzymes + receptors are protein bodies made to recognize a certain molecule
1% of human genes is for immune system –proteins that
recognize old enemies & also adopt to new ones (virus identification +
destruction takes days)
1% of human genes are dedicated to the olfactory system – but
there is no adaptation but instant recognition of a smell.
Ref: Chandler Burr (2002) The Emperor of Scent, Random house , N.Y.
Sensing of primary odors
after Moore et al. 1964
The stereochemical theory of odor, American scientist
Primary odor
Chemicals
Examples
Camphoraceous camphor
moth repellent
Musky
pentadecanolactone Angelica root
Floral
phenylmethylethyl carbinol
roses
flowery
Trans-alpha-ionone
Viola sp.
Peppermint menthone, menthol
mint candy
Ethereal
ethylene dichloride dry-cleaning fluid
Pungent
formic/ acetic acids
vinegar
Putrid
butyl mercaptan
foul eggs
An electronic Nose ?
When a polymer film is exposed to a gaseous vapor, some of the vapor
gets into the film and causes the film to swell. The vapor-induced film
swelling produces an increase in the electrical resistance of the film
because the swelling decreases the number of connected pathways of the
conducting component of the composite material. The detector films are
made from an insulating organic polymer that swells plus an inorganic
conductor such as carbon black, Au, Ag, etc .. The electrical resistance of
the film is then read using simple, low power electronics.
Arrays of chemically sensitive conducting polymer films. that
individually respond with resistance changes to vapors can produce
a distinguishable response patterns like mammalian olfactory senses
flavors and fragrances
Plant names referring to scent & taste
Agathosmus = aromaticus = fragrans = odoratus = fragrant
blandus = mild, pleasing citriodorus = lemon-scented deliciosus =
delicious dulcis = sweet foetidus = evil-smelling glycyrrhizus =
like licorice
graveolens = heavy scented inodorus = scentless
meliodorus = honey-scented oxycarpus = with sour fruit phu = rotten
saccharatus = sugary sweet salsillus = salty suaveolens = sweet smell
fragrant horticulture plants: Daphne odora (spring air), Galium
odoratum (woodruff), Lathyrus odoratus (sweet pea), Myrrhis odorata
(sweet cicely), Nymphea odorata (sweet lotus), Reseda odorata
(mignonette), Viola odorata (sweet violet)
Plant names explained. Botanical terms & their meaning. Bastyr Library
QK. P63. 2005 Horticulture Publications, Boston MA USA 2005
No doctrine but signatures Î “Plants have glands”
Clear giveaways = signatures = anatomical clues that plants have
sequestered lots of active compounds Î glandular trichomes, lacticifers,
idioblasts, resin canals, floral & extrafloral nectaries
Spices and perfumes – Apiacea or carrot/parsley family
Umbelliferae: umbel as inflorescense; flat-topped clusters of flowers
Parsley (Petrosselinum crispum) leaf; dill (Anethum graveolens) leaf; cilantro
(Coriandrum sativum) leaf and fruit (coriander spice)
Spices and perfumes – Labiatea or mint family
Mints have asymmetric, bilabiate (two-lipped) flowers, often in in axial nodes, square
stems and opposite, fragrant leaves
Rosemary (Rosmarinus officinalis), Thyme (Thymus vulgaris) antiseptic; Oregano
(Origanum vulgare), Majoram (Origanum sp); Basil (Ocimum basilicum) Chatreuse;
Sage (Salvia officinalis) stuffing, Peppermint (Mentha piperita); spearmint (Mentha
spicata)
Picture
of leaf
glands
Citrus family
Pressurized vacuoles with essential oils protect citrus fruits.
Interior of these fruits is isolated by thick cuticle and pectin layer.
The Smell of Spring is here:
Daphne odora: earliest strong smelling
flowers on Bastyr and UW Campus
Daphne x Burkwoodii: showy & fragrant spring flowers
Allspice Calycanthus californica both flowers a&
rubbed leaves have wonderful smell
Syringa : lilac flowers strong aromatic smell in spring
Choisya ternata Mexican orange scented spring flowers
Buddleia davidii: distinct fragrance in summer flowers
Hamamelis mollis: Witchhazel spicy-scented winter
flowers
Jasminum nudiflorum: gentle smell of winter flowers
Gardenia jasminoides smell of Hawaii spring/summer
flower
Lonicera Honeysuckle : familiar sweet smell in flowers
Winter jasmin
Scented Flowers are fine, Scented Leaves are divine
Aloysia triphylla Lemon Verbena: lemonscented foliage
Allspice or Sweetshrub Calycanthus floridus
rubbed leaves have smell
Labrador tea Ledum groenlandicum : leaves
used for tea
Lindera benzoin Spicebush crushed leaves with
citrus scent
Rosmarinus officinalis: desinfecting stron smell
of this herb
Sage Salvia officinalis: Sage S fructicosa used in
cooking
Sassafras officinalis: root, bark & leaves strongly
scented
Thymus vulgaris scented herb is actually a shrub
Ruta graveolens Rue : strong scent in foliage
Scent of foliage vs scent of flowers (Kerner’s rule)
ÎKerner von Marilaun (1904)
Kerner’s rule:
Scent of foliage is mostly insect repellent while
Scent of flowers is mostly insect attractant
Alliums (e.g. garlic) honey-smelling flowers,
smelling foliage
Conium maculatum (hemlock) honey-smelling
flower, but repulsive smell of mice for the rest
•Exceptions to the rule Î
same odor in flower and vegetation
Primula auricula,
Viola odorata,
Gaultheria procumbens (wintergreen),
woodruff (Galium odoratum),
Lavendula vera etc.
Scents as a Defense?
Polemonium viscosum has blue to purple flowers.
Some of them have a sweet scent (esters or
terpenes) others have a skunky smell (amines).
The pollinator of the Polemonium is the bumblebee
Bombus kirbyellus, which prefers sweet smelling
flowers without consideration for color.
Îa lot of questions like
“ was there another pollinator before ? or
“do the skunky flowers deter pollen robbers like ants?”
If so it is an example for smell as defense
What about Kerner’s rule: Scent of foliage is mostly insect
repellent while Scent of flowers is mostly insect attractant
William Agosta “ Thieves, deceivers and killers. Tales of
chemistry in nature”, Princeton University Press 2001
5 groups of flower odors
according to Kerner von Marilaun (1904)
Kerner’s rule: Scent of foliage is mostly insect repellent while Scent of flowers
is mostly insect attractant
Alliums (e.g. garlic) honey-smelling flowers, negi smelling foliage
Conium maculatum (hemlock) honey-smelling flower, repulsive smell of mice for
the rest
• Exceptions to the rule (same odor in flower and vegetation):
Primula auricula, Viola odorata, Gaultheria procumbens (wintergreen), woodruff
(Galium odoratum), Lavendula vera etc.
1. Indols:
indol and skatol with the smell of corpses and excrements (repulsive to Pongo
sapiens, decay products of proteins)
• in red to brown flowers and reddish veins of
• Aristolochia (dutchmen’s pipe, shape and smell of decaying tobacco in a. gigas), Asarum
caudatum (wild ginger), Rafflesia species
2 Aminoids: trimethylamine (TMA) smells like herring brine, occur in in flowers of :
• Spiraea, hawthorn (Cretaegus), pear, Mountain ash (Sorbus), dogwood (Cornus)
• Elder berry (Sambucus racemosa), Barberry (Berberis or Mahonia), Chestnut (Castanea),
Horse chestnut (Aesculus hippocastanum), Ash (Fraxinus), Primrose (Oenothera), Ivy
(Hedera), tree of heavens (Ailanthus)
Benzoloids/ Phenolics:
pleasant smell of
Lilac (Syringa vulgaris), similar smell in
the laurels Daphne striata & odorata (indicates similar pollinators)
Lily of the valley (Convallaria majalis)
Narcissess (Narcissus poeticus)
Vanillin smell in Heliotrope, twin flower (Linnea borealis), Daphne
alpina, Nardosmia fragrans
carnations (eugenol),
sweet woodruff Galium/ Asperula odorata (coumarin),
spicebush Lindera benzoin,
Calicanthis (all spice bush)
Choysia (Mexican orange)
(bay laurel)
Kaimonia
Umbellaria (Californiua bay leaf/laurel)
Paulownia, Lonicera (honey suckle)
Meadowsweet (salicylic aldehyde,
)
oil of wintergreen Gaultheria procumbens (methyl salicylate- a relative
Paraffins:
flowers of roses (Pelargonic acid),
valerian (valerianic acid in Valeriana offcinalis)
vine (Vitis vinifera, enanthic acid)
thorn-apple (Datura stramonium)
Petunia flowers, Paeonia flowers
elderberry (Sambucus nigra), tobacco, tomato and other nightshades
honey-scent in flowers of
apricot, cherry, almond, Rhamnus, forget-me-not (Myosotis alpestris) Phlox
(Phlox paniculata)
willows (Salix), Angelica etc.
Terpenes (isoprenoids):
lavender (Lavendula),
citrus, orange flowers (Citrus limon)
same scent also in Gardenias,
in some magnolia flowers and thyme
(Thymus citriodorus)
mints etc.,
Violets (alpha-ionon),
banana oil (isopentenyl acetate),
flavors and fragrances
limonene in citrus fruits and
menthol in the labiatae
vanillin
discovered as the first
natural flavor in
vanilla pods in 1872
Odors – volatile compounds matching olfactory receptors
(1) Aldehydes: acetaldehyde is a pungent volatile imparting odor of
super-ripe fruits, cinnamon aldehyde is giving away
(2) Esters of organic acids: oil of wintergreen is not an oil but an ester
made from salicylic acid and methanol, pine apple odor is ehtylbutyrate
(3) Terpenes (as in essential oils, resins etc.): Steam-distillate pine
needles which are available in huge amounts and give you essential oils
that contain pinene etc.
(4) Amines: Stinking goosefoot Chenopodium has amines that can be
extracted with Na carbonate or NaOH Î trimethylamine that stinks
like fish, try this with skunk cabbage
(5) Sulfur-containing compounds: buthanethiole as in skunks, diallyl
disulfide –odor of wounded garlic, allyl propyl disulfide –odor of onions
(6) Phenolic volatiles: e.g. Coumarins – the “fresh hay” smell from
woodruff, Vanilla leaf and sweet clover, gum benzoin etc.
Flavour – phytochemcials with special meaning to humans
Flavours principles: one has to differentiate between substances
that have been isolated from a spice or that simulate one!
apple ethyl-2-methylbutyrate
banana amylacetate & eugenol
coconut @-nona-lactone
lemon citral (limonene= smell
peach
undeca-lactone
vanilla
vanillin
celery
apiole, myristicine
mushrooms lenthionine
onion
Dipropyl disulphide,
propanethiol lachrymator
Esters : amylacetate
banana
ethyl-methyl butyrate
apple
Harborne JB (1988) Introduction to Ecological Biochemistry, Academic Press London
5 groups of flower odors
according to Kerner von Marilaun (1904)
Kerner’s rule: Scent of foliage is mostly insect repellent while Scent
of flowers is mostly insect attractant
Alliums (e.g. garlic) honey-smelling flowers, negi smelling foliage
Conium maculatum (hemlock) honey-smelling flower, repulsive smell of
mice for the rest
• Exceptions to the rule (same odor in flower and vegetation):
Primula auricula, Viola odorata, Gaultheria procumbens (wintergreen),
woodruff (Galium odoratum), Lavendula vera etc.
1. Indols:
indol and skatol with the smell of corpses and excrements
(repulsive to Pongo sapiens, decay products of proteins)
• in red to brown flowers and reddish veins of
• Aristolochia (dutchmen’s pipe, shape and smell of decaying tobacco in a.
gigas), Asarum caudatum (wild ginger), Rafflesia species
2 Aminoids: trimethylamine (TMA) smells like herring brine, occur in in
flowers of :
• Spiraea, hawthorn (Cretaegus), pear, Mountain ash (Sorbus), dogwood
(Cornus)
• Elder berry (Sambucus racemosa), Barberry (Berberis or Mahonia), Chestnut
(Castanea), Horse chestnut (Aesculus hippocastanum), Ash (Fraxinus),
Primrose (Oenothera), Ivy (Hedera), tree of heavens (Ailanthus)
Benzoloids/ Phenolics:
pleasant smell of
Lilac (Syringa vulgaris), similar smell in
the laurels Daphne striata & odorata (indicates similar pollinators)
Lily of the valley (Convallaria majalis)
Narcissess (Narcissus poeticus)
Vanillin smell in Heliotrope, twin flower (Linnea borealis), Daphne
alpina, Nardosmia fragrans
carnations (eugenol),
sweet woodruff Galium/ Asperula odorata (coumarin),
spicebush Lindera benzoin,
Calicanthis (all spice bush)
Choysia (Mexican orange)
(bay laurel)
Kaimonia
Umbellaria (Californiua bay leaf/laurel)
Paulownia, Lonicera (honey suckle)
Meadowsweet (salicylic aldehyde,
)
oil of wintergreen Gaultheria procumbens (methyl salicylate- a relative
Paraffins:
flowers of roses (Pelargonic acid),
valerian (valerianic acid in Valeriana offcinalis)
vine (Vitis vinifera, enanthic acid)
thorn-apple (Datura stramonium)
Petunia flowers, Paeonia flowers
elderberry (Sambucus nigra), tobacco, tomato and other nightshades
honey-scent in flowers of
apricot, cherry, almond, Rhamnus, forget-me-not (Myosotis alpestris) Phlox
(Phlox paniculata)
willows (Salix), Angelica etc.
Terpenes (isoprenoids):
lavender (Lavendula),
citrus, orange flowers (Citrus limon)
same scent also in Gardenias,
in some magnolia flowers and thyme
(Thymus citriodorus)
mints etc.,
Violets (alpha-ionon),
banana oil (isopentenyl acetate),
Many plants reek but there is one that can smell
Cuscuta (Dodder) is a genus of about 100-170
species of yellow, orange or red (rarely green)
parasitic plants. Formerly treated as the only genus
in the family Cuscutaceae, recent genetic research
placed it in the morning glory family,
Convolvulaceae Dodder can be identified by its thin
stems appearing leafless, with the leaves reduced to
minute scales. It has very low levels of chlorophyll.
The dodder's stem elongates quickly and waves slowly in the air,
checking for odors from other plants. Science (Vol 313; Sept. 29, 2006)
by Runyon, Mescher, and De Moraes at Penn State demonstrates that
dodder use airborne (volatile) chemical cues to locate their host plants.
Seedlings of Cuscuta pentagona exhibit positive growth responses to
volatiles released by tomato and other species of host plants. When given
a choice between volatiles released by the preferred tomato and the nonhost wheat, the parasite exhibited preferential growth toward the former.
Odors – volatile compounds matching olfactory receptors
(1) Aldehydes: acetaldehyde is a pungent volatile imparting odor of
super-ripe fruits, cinnamon aldehyde is giving away
(2) Esters of organic acids: oil of wintergreen is not an oil but an ester
made from salicylic acid and methanol, pine apple odor is ehtylbutyrate
(3) Terpenes (as in essential oils, resins etc.): Steam-distillate pine
needles which are available in huge amounts and give you essential oils
that contain pinene etc.
(4) Amines: Stinking goosefoot Chenopodium has amines that can be
extracted with Na carbonate or NaOH Î trimethylamine that stinks
like fish, try this with skunk cabbage
(5) Sulfur-containing compounds: buthanethiole as in skunks, diallyl
disulfide –odor of wounded garlic, allyl propyl disulfide –odor of onions
(6) Phenolic volatiles: e.g. Coumarins – the “fresh hay” smell from
woodruff, Vanilla leaf and sweet clover, gum benzoin etc.
Leaf alcohol =
cis-3 hexenol
from leaves of
Mentha arvinca or
tomato has
smell of cut grass.
This alcohol is
frequently used in
floral fragrances ,
in fruity flavors and
green tea flavors.
cis-3-Hexenol gives a
fresh green effect
although it is
purely synthetic
Synthetic Odorants
Benzonitrile
PhCN
synthetic
Smells like KIWI shoe polish
aromatic organic abbreviated PhCN.
colourless, with a sweet almond odour.
It is prepared by reaction of sodium cyanide with
bromobenzene. Typical smell of cyanogenic
compounds.
Ref: Chandler Burr (2002) The Emperor of Scent, Random house , N.Y.
6. Esters of organic acids
are highly unstable. Essential (ethereal) oils last (perfumes), esters
hydrolyze during sweating and stink.
Apple smell is imitated by methyl butyric acid, butyric acid itself smells
like rancid butter and is the give-away odor of perspiring humans
(traceable by most animals)
Isoamyl acetate is an ingredient of banana ice cream, but it is also the
attack pheromone for honeybees, you design your own catastrophic
experiment.
isopentenyl acetate has no natural occurrence but it is “the juicy fruit
principle” in artificially flavored drinks
Many/most flowers exude a mixture of odors from different groups:
jasmine, lilly of the valley etc. But insect attraction is not limited
to one sense, but often a combination of odors, color and display
Esters as odoriferous signals
Esters easily hydrolyze during sweating or with bases & acids.
Therefore not used in perfumes.
Apple smell is imitated by methyl butyric acid (when demethylating to
butyric acid it will smell like rancid butter (attack of fem mosquitos)
isoamylacetate is aroma of bananas & also attack signal for honeybees
isopentenyl acetate is artificial fruit aroma,
isobutyl propionate is art. rum aroma, benzyl acetate art peach aroma
ethyl phenylacetate resembles the aroma of honey
Fragrances
Fragrance chemistry is an extremely complex science and art.. There are over 5000
chemicals and materials used in the fragrance industry. A fragrance formula may
contain as few as 10 or as many as several hundred & up to 600 different ingredients.
5. Now let’s make synthetic esters using the following formulas:
acid
1 gram salicyclic acid
alcohol
2 mL methanol
sulfuric acid fragrance
8 -10 drops
wintergreen
10 -15 drops
orange
3 mL acetic acid
2 mL octyl alcohol
4 mL formic acid
2 mL ethanol
2 mL butyric acid
2 mL ethyl alcohol
15 -20 drops
pineapple
2 mL butyric acid
2 mL methanol
15 -20 drops
apple
20 drops
rum
1. Prepare hot water bath with a 400 mL beaker water on a hot plate, to slightly boiling.
2. Add the acid & alcohol ingredients to a test tube.
3. Into that solution you add the catalyst sulphuric acid.
4. place the test tubes into the hot water bath for about one minute.
5. Notice the essence.
6. Bastyr is fragrance-free environment!
flavors and fragrances
Plant smells Î Esters
Pittosporum tobira (Pittosporaceae) Tobira,
is a dense, rounded, evergreen shrub native to Japan, China,
& Korea. The odor of the small flowers is somewhat
reminiscent of orange flowers (neroli).
The main component of the flower oil of tobira is the
ester benzyl acetate
Asparagus officinalis (Liliaceae) has strongly reduced leaves.
Asparagus sap is rich in the amino acid L-asparagine which
contributes ot the taste-enhancing umami character. It was
the first amino acid to be isolated in 1806 from asparagus.
Most people observe a distinct odor from their urine shortly
after eaten asparagus. This is caused by organic sulphur
compounds: like methanethiol, dimethyl sulfide, dimethyl
disulfide etc.
Terpenes (isoprenoids)
1887 Otto Wallach: isoprene rule:
all terpenes are made of C5 units
synthesis starts not from AAs but from
AcCoA Î isopentenenyl PP
Hemiterpenes 5C, pure isoprene reported
to be released from leaves of many plants,
also tiglic + angelic acid, all are volatile
Monoterpenes 10C, volatile & hence
major constituents of essential oils
. .
acyclic MT: myrcene (Laurus nobilis),
geraniol geranium Pelargonium), linalol
(major ingr of Coriandrum sativum . . . .
cyclic MT: menthol (Mentha sp), camphor
pinene (major ingredient of turpentine),
limonene, carvone (Carum carvycaraway
seeds), thujone (convulsant blocks GABA
Cl channels), @ ionone (viola, Channel#6
Simple monocyclic terpenoids
– simple pleasures
Monocyclic terpenoids are known by
their smell
Lemongrass
Cymbopogon Lemongrass is a tall
perennial grass, native to India. It is widely
used as a herb in Asian cuisine. It has a
citrus smell and can be dried and powdered.
Citronella Grass (Cymbopogon nardus)
grows to 2 m and is used for the production
of citronella oil, which is used in soaps, as
a mosquito repellent in insect sprays and
candles, and also in aromatherapy,
Principal chemical constituents of
citronella: geraniol and citronellol are
antiseptics, hence their use in household
disinfectants and soaps.
Sesquiterpenes - volatile (smell!) or bitter (taste!)
Sesquiterpenes 15C
aliphatic & cyclic
artemisinin b antimalaria drug
cardinene (juniper & cedar tree)
santonin is anti-thelmic of
wormwood Artemisia maritima
Acorone is smell of sweetflag
Acorum calamus
Caryophyllene major ingr in
clove oil Eugenia (not eugenol)
Abscisic acid dormancy-inducin
hormon of buds & seeds
Tetrahydroidentin is bitter in
dandelion Taraxacum officinale
humulene bitter in Pilsner beer
gentianin bitter in Gentium liqu
Diterpenes - volatile (smell!) or bitter (taste!)
Diterpenes 20C: aliphatic, cyclic but
no longer volatile Î resins
Gibberellins are plant hormones
taxol yew tree taxus, antimitotic
podolactone from Podocarpus
(evergreen conifer Gondwanaland)
with antileukemic activity
Marrubiin from horehound
Marrubium vulgare vasorelaxant
Clerodanes from Ajuga, Salvia,
Teucrium have antifeedant char.
zoapatanol from Mexican Zoapatle
plant Montanoa toment. abortifacient
Bizarre Plants :Dictamnus
The burning bush Dictamnus albus is a member of the Rutaeceae. Many
plants of dry locations are known to increase production of terpenes to
cool leaf surfaces by terpene transpiration. Dictam, however, produces
so much that it can undergo self-ignition (see burning bush stories in
Bible & Koran) .
It is thought that droplet formation in the leaf focuses sunlight to a
temperature that ignites terpenes which burn like a gas grill using the
stomates as valves.
Plant smells
CloverTrifolium spp (Fabaceae) smell
dominated by acetophenone (24 %), methyl
cinnamate (11 %), 1-phenylethanol (8 %),
Cinnamon tree bark is
dominated by c aldehyde
cinemaldehyde
Clary sage Salvia sclarea (Labiatae) Essential oil made by steam distillation of the
flowering tops has main constituents (-)-linalyl acetate (67 %) and (-)-linalool (16 %).
Ambergris-like nuances are due to oxidative degradation products of the diterpene
sclareol Î (-)-ambrox. Sclareol is the main constituent (> 70 %) of the essential oil
(concrete) made by extraction.
The fragrant clove buds contain 20 % essential oil.
Eugenol (ca. 80 %), eugenyl acetate and caryophyllene
are main constituents.
Allelopathy of the air –volatile terpenes against grasses
Californian chaparral has shrubs Salvia leucophylla & Artemisia
tridentata that create bare circles of soil with a diameter of 1-2 m,
beyond there are some herbs and then start grasslands with Avena,
Bromus, Festuca species
The substances that are released a volatile terpenes that compose a cloud
around the plants and accumulate in dry soil around the roots. The
terpenes are in Salvia l. sagebrush: 1,8-cineole and camphor
.
in Artemisia tr sagebrush: same + pinene + camphene,
The volatiles of the Apiaceae
The volatiles and hence smell of carrot family plants is a complex
mixture of terpenes & phenols. Apiol is a diuretic & the major
constituent of the oil of parley seeds Petrosillium , trans-Anethole
determines smell & taste of of anise seeds Pimpinella anisum. Phenyl
propanoids are water-insoluble phenolics with three-carbon side chains;
anethole and myristicin are determining the semll of nutmeg. Eugenol
is a dental analgesic from oil of cloves but occurs in many plants.
Caffeic & coumaric acid give aroma to coffea beans, raw or roasted.
Monoterpenes: Carvone is major component of Caraway Carum carvi,
linalool is principle const of coriander Coriandrum sativum
Scents as Life’s Elixir? The bee’s way to extract essential oils
We know that the fragrance of flowers is a signal to
guide insect & bat pollinators to the flowers where
they are rewarded by food donations in the form of
either pollen or nectar
However, some plants do not offer food, e.g. orchids.
They offer either illusion of sex (bee orchid), violence
(hammer orchid) or a selection of fine fragrance (bee o)
Euglossine bees are the pollinators of bee orchids,
which reward them with scents generated by glands in
the orchid flowers producing about 60 various scents.
The male bees exude some lipid solvent to their front
feet & mop the scents up to finally collect them in slitopening bags of the hind feet. Bees show intoxication &
falls into a bucket that leads to the anther where a pollen
packet (pollinarium) is glued to its head; funny looks Î
This orchid fragrance Î
extends the life span of the male euglossine bees!
Plants produce specific insect poisons, hormones and
sexual attractants
Mutualism (+ +) or
Commesalism (+ 0) ???
Wound-induced
airborne volatiles
as SOS signals:
insect regurgitant
volicitin (amine)
triggers synthesis of
volatile terpenoids
as wasp attractants
in maize
through methyl
jasmonate in cotton
Through terpenoid
trans-2- hexenal in
Phaseolus
No-man’s land made by allelopathic plants –
Ambrosia artemisifolia – infamous ragweed
volatile communication
Stick insects throw brown, shiny hard-shelled eggs with an
detachable appendage rich in lipids – they mimic seeds
ants transport them to the safety of their nest, severe the
appendage and dump them now far away from home.
Many plants are as sedentary as the stick and need the same
help in propagating their species.
Bloodroot (Sanguinaria canadensis), castor bean (Ricinus
officinalis) and many other seeds have oilbodies that attract
ants that store them safely in their nests undergound, severe
the elaiosome and let them germinate on their well
fertilized garbage dump.
Æ Cape of South Africa invaded by foreign ants and many
plants disappeared
1.signal is oleic acid which also signifies a dead ant Î impulse to get it to exit. oleic
acid is one of the principal unsaturarted fatty acids of plants:
2. signal is 1,2- diolein, insect fat smelling like ant brood
Insects mimicking Plant Seeds
We know that passion flowers mimic the deposition of
eggs on their leaves in order to deter the pregnant butterfly
to deposit her eggs next to their cannibalistic cousins.
But there are insects who mimic plant seeds, in particular
the Stick Insect – a slow moving leaf eater mimicking a
branch. Unlike most soft insect eggs, these have a shell
hardened by Ca salts and take a brown, shiny
appearance of a seed. More important is appearance of a
capitulum rich in fats & resembling seed elaiosomes, that
are detached by foraging ants without damage to the egg.
The ants transport the eggs like seeds to their nests, detach the fat
bodies to feed their larvae and deposit the rest on their junk pile
an ideal breeding ground for plant seeds and a protected place
from predating wasps and plant eaters
A famous plant in S Africa depends on ant propagation: red stump
or Mimetes cucullatus. Introduced Argentine ants do not
transport the seeds & where they rule, the plants rapidly disappear
Stick insect
bloodroot
PAL + blue light Î Phenolics
The plants’ blue-light switch to the synthesis of phenolic metabolites
Plant smells
CloverTrifolium spp (Fabaceae) smell
dominated by acetophenone (24 %), methyl
cinnamate (11 %), 1-phenylethanol (8 %),
Cinnamon tree bark is
dominated by c aldehyde
cinemaldehyde
Clary sage Salvia sclarea (Labiatae) Essential oil made by steam distillation of the
flowering tops has main constituents (-)-linalyl acetate (67 %) and (-)-linalool (16 %).
Ambergris-like nuances are due to oxidative degradation products of the diterpene
sclareol Î (-)-ambrox. Sclareol is the main constituent (> 70 %) of the essential oil
(concrete) made by extraction.
The fragrant clove buds contain 20 % essential oil.
Eugenol (ca. 80 %), eugenyl acetate and caryophyllene
are main constituents.
Synthesis of Phenolic compounds starts from AAs
Phenylalanine Cinnamic acid
Synthesis of phenolics (also called
phenylpropanoids starts from the
aromatic amino acids Phenylalanine
& Tyrosine,but not from Tryptophan
Cinnamic acid is a spice plus a
strong antifungal & allelopathic
Simple Phenolics or phenylpropanoids
Vanillin, first synthesized in 1872
Salicylic acid, Methyl Salicylic acid =wintergreen;
volatile signal) Ferulic acid, Caffeic acid
simple phenols
Methyl salicylate is the so-called “oil” of wintergreen
release of volatile methyl salicylate by leaves of tobacco is also an important signal for
some wasp to attack predating caterpillars
Cinnamonic aldehyde is fragrant
Cinnamon trees are native to South East
Asia, but its origin was mysterious in Europe
until the sixteenth century. Due to the
presence of coumarin, European warned
against consuming large amounts of Cassia
which cause liver and kidney damage in high
concentrations. Ceylon cinnamon has
negligible amounts of coumarin.
Cinnamaldehyde gives cinnamon its
flavor and odor. A pale yellow viscous
liquid from the bark of cinnamon trees and
other species of the genus Cinnamomum
The essential oil of cinnamon bark is
about 90% cinnamaldehyde. from the
cinnomon tree Cinnamomum zeylandicum
by steam distillation of the bark.
Cinnamonum zeylanicum
Camphor
Camphor is a waxy, white solid with a
strong, aromatic odor found in wood of the
camphor laurel (Cinnamomum camphora),
an evergreen tree found in Asia. can also be
synthetically made from oil of turpentine.
It is used for its scent, as an ingredient in
cooking (mainly in India), embalming fluid
Chinese Camphor from the tree
Cinnamomum camphora has poor quality
Borneo camphor comes from tree
Dryobalanops aromatica (after the city
Baros on Borneo. To get camphor you
make incision in the tree and get several
buckets of Camphory juice. Later you
repeat the same halfway down the tree.
After that the tree dies….
Cinnamonum camphora
The Curry Tree & the Curry plant
The curry tree (Murraya koenigii) is a
tropical tree in the Rutaceae, which is native
to India.
The leaves are fragrant and used used in
curries ("curry leaves“ or "sweet neem
leaves." as unavoidable content of curries
in South India,
Not related to Curry Plant, Helichrysum ital.
Helichrysum italicum – the curry plant is a
flowering plant of the daisy family
Asteraceae native to the Mediterranean.
It is called the curry plant because of the
strong thyme-like smell of its leaves.
It has nothing whatsoever to do with the
mixture of spices used in Indian cooking, nor
with the curry tree (Murraya koenigii).
Choysia ternata Mexican Orange
Choysia ternata is a member of the Rutaecea
(Citrus family) . Mexican orange is a small and
compact evergreen broadleaf shrub that gets about
6-8 ft (1.8-2.4 m) tall.
The leaves are opposite and palmately compound
with three elliptic leaflets, each about 2-3 in (5-8
cm) long. When bruised they give off a strong
and pungent smell.
The white 4 or 5-petaled flowers are about 1 in (2.5
cm) across and deliciously fragrant. They stand in
clusters of above the foliage.
Mock-orange (Philadelphus lewesii, are shrubs from 1
to 6 m tall, native to North America, They are named
"mock-orange" since their flowers are similar to those of
oranges and lemons (Citrus) But Philadelphus is a
asterid, not related to Citrus (advanced rosids).
Phenols as flavors
4% of the
beans
catechins
Phenolics Î Coumarins
Characterized by the lactone double ring, volatile with smell of mawn
hay, reduces capillary permeability & edemic swelling
Sources: Apium graveolens (celery
seeds radix), leaves, Angelica,
Gallium odorata = woodruff
Melilotus officinalis (sweet clover)
Achlys triphyllum Vanilla leaf
Tonka beans
Liatis odoratissima = deer tongue
Phenolics Î the bloody DiCoumarins
Coumarin is water-insoluble but in alkaline solution 4-hydroxy coumarin
can be soluble. It is not an anticoagulant but it does fluoresce.
Dicoumarol is an anticoagulant that
functions as a Vitamin K
antagonist (similar to warfarin, for
which it was the inspiration).
Dicoumarol is a natural chemical
substance when coumarin is
transformed in mouldy feeds or
silages by a fungi, into dicoumarol.
Dicoumarol in silaged wet sweetclover hay, was the cause of
bleeding disease in cattle
(identified in WI, USA in 1940)
Mechanism:
prevents formation of prothrombin
Natural Coumarins can kill sheep
Natural Coumarins can kill sheep
Phenolic protect wood for ages
Lebanon cedar was the pride of the
Phoenician fleet. It was not attacked
by fungi or mussels.
However this was also the cause of the
deforestation of North Africa
Phenolic odors
Coumarin benzopyrone;
toxin found in many plants,
notably in tonka bean,
vanilla leaf, vanilla grass
woodruff Galium odoratum,
mullein Verbascum, bison
grass, sweet clover Melilotus
cassia bark, one of the
cinnamon species:
1 teaspoon of cinnamon
powder contains 5.8 to
12.1 mg of coumarin,
a sweet scent of newlymown hay, has been used in
perfumes since 1882.
Banned in foods, not drinks
Plant smells Î Coumarins
Melilotus albus (Fabaceae) White sweetclover
Coumarins are found in many plants - sweetgrass, vernal
grass, sweetclover, woodruff, Vanilla leaf, lavender, tonka
beans, etc.
In the fresh, living plants coumarin is mostly present as a
glycoside (e.g. melilotoside in sweetclover). When the
plants are injured or wither, the glycosides are split by
enzymes. Hence the term “sweet after-death” used for the
smell pf the pillows stuffed by the pioneer women.
coumarine
Couman Coumane ®, a cyclopropane analogue of coumarin from
Flexitral, has just received FEMA GRAS status for use as a flavor.
Tonka (Dipteryx odorata) beans – or the smell of coumarin
The tonka bean is the seed of Dipteryx odorata, the cumaru legume tree
The seed is black and wrinkled in appearance, with a smooth brown
interior. It is known mostly for its fragrance, which is reminiscent of
vanilla, almonds, cinnamon, and clove Î used in perfume & tobacco
before being banned in some countries.
The seed contains coumarin, which
can be lethal Î use in food is banned
in the US by the FDA. Prescription
drugs use more powerful forms of
coumarin.
Tonka is legal in the EU & a fashion
ingredient in French cuisine (mostly
in desserts &stews).
The plant originates from South
America (Guyana, Orinoco region)
Vetiver - oil of tranquility
Vetiver is oil of tranquility
distilled from the rootlets of
Vetiveria zizanoides or
Khus-Khus grass,
imported from Haiti. It has a heavy,
woodsy, earthy-sweet scent. Some
traditional uses: for muscular
aches, to increase circulation, to
relieve melancholy and nervous
tension, for restful sleep.
Emotional profile: for fears,
obsessions, scattered thoughts,
anger and hurt, unworthiness,
neurotic behavior, addiction. Blends
with: sandalwood, ylang ylang,
clary sage, lavender, patchouli,
Oil of tranquility
jasmine and rose.
Vetiver roots
Primary metabolites: L-amino acids H2N- in @ position to -COOH, 23 AAs
essential in all organisms
Secondary metabolites: >200 non-proteinogenic AA, many synthesized
by plants of the legume family: poisonous for most herbis: D-AAs
Decarboxylation of AAs ---> amines,
- COOH ---> -H
Examples for simple amines (can be isolated with cation exchange resin )
Lysin ---> cadaverin H2N(CH2)5NH2
(MO, seeds, flowers)
Ornithine ---> putrescine
H2N(CH2)4NH2 (stinking, MO, flowers)
HO-Tryptophan ---> auxin,
Histidine ----> Histamine
Volatile Amines stink
While phenolic compounds derive from aromatic Amino Acids by deamination, amines derive by decarboxylation (e.g. histidine to histamine)
Decarboxylations of AAs occur naturally in plants and also after death in
animals, especially rapid in fish (methylamine, trimethyl amine). Especially
bad is the smell of putrescine and cadaverine. Plants realized that these
amines attract dung flies as pollinators.
trimethylamine
Putrescine & cadaverine follow this
Bizarre Plants
Monstrous + stinky (amines): Amorphophallus titanum, Rafflesia
arnoldii, Aristolochia grandiflora (Humboldt), Welwitschia mirabilis,
Victoria amazonica, Aztecs’ handflower tree Cheirostemon platanoides
(related to Cocoa tree, Humboldt), Baobab (sausage) trees Adansonia,
boogam trees Idria columnaris (desert in Baja California), elephant or
skunk tree Bursera microphylla (Baja California; tug on leaf & it burps
out a foul smelling, fetid spray over a distance of 50 cm), squirting
cucumber Ecballium elaterum shoots fruit as a rocket over 3 m distance,
slimy mucilage with seeds sticks to the one who touched the fruit
WB Emboden(1974): Bizarre Plants; magical, monstrous, mythical. MacMillan P. NY
Stinking Plants
Corps Flower Titan arum. with sharp points at the pollen
surface. One plant produces a billion grains of pollen that can
stay airborne for days spreading over an area of many miles.
Affects 75 % of all allergy sufferers.
Rafflesia arnoldii. Rafflesia was found in the Indonesian rain forest
by an Indonesian guide working for Dr. Joseph Arnold in 1818, &
named after Sir Thomas Raffles, leader of the expedition
Stinking Iris Iris foetissima. It is known as "stinking" because
some people find the smell of its leaves unpleasant when
crushed or bruised, an odour that has been described as "beefy"
Stinking Hellebore Helleborus foetidus, known variously as
stinking hellebore, dungwort, and bear's foot, is in Ranunculaceae,
native of the mountainous regions of Central and Southern Europe
Skunk cabbage Symphocarpus foetidus is one
of the many stinky plants in its family the
Araeceae.
The burping skunk tree
is a member of the Burseraceae, related to frankincense (Boswellia) and myrrh
(Commiphora) but unlike them it stinks (skunk tree).
The elephant tree Bursera microphylla is native to Northern Mexico, Southern
California and Arizona, especially desert regions. It reaches 5 m in height. The foliage
is made up of long, legume-like leaves which are composed of paired leaflets. It flowers
in rounded yellow buds which open into small, star-shaped white or cream flowers
When you tug on a
leaf it burps and
emits a fine spray
over 50 cmm
distance that is
foul fetid smelling
caused by amines
Scents as a Defense?
Polemonium viscosum has blue to purple flowers.
Some of them have a sweet scent (esters or
terpenes) others have a skunky smell (amines).
The pollinator of the Polemonium is the bumblebee
Bombus kirbyellus, which prefers sweet smelling
flowers without consideration for color.
Îa lot of questions like
“ was there another pollinator before ? or
“do the skunky flowers deter pollen robbers like ants?”
If so it is an example for smell as defense
William Agosta “ Thieves, deceivers and killers. Tales of
chemistry in nature”, Princeton University Press 2001
Stinky plants: the Durian fruit
The Durian is the fruit of
trees from the genus Durio
and has been known and
consumed in southeastern
Asia since prehistoric times,
but has only been known to
the western world for about
600 years.
This is a fruit, which
smells like a rotting
corpse, and has actually
been banned in some hotels
Sulfides, e.g. garlic Allium sativum
Sulfides (except for AA cysteine, methionine) restricted to few families
characterized by obnoxious odor, simple HC sulfides in Allium species
including lachrymators, in Brassica, radish, onions glucosinolates or
mustard oils, thiophenes in Asteracea in association with polyacetylens.
6000 a ago Egypt, garlic produces lots of sulfur-containing volatiles that
repel insects & other herbivores. Inside the vacuoles there is a colorless,
odorless compound called alliin. The cytosolic enzyme allinase
converts alliin into sulfenic acid + ammonia. Two sulfenic acid
molecules combine to allicin – smelly & fiery tasting compound that
breaks down to diallyl disulfide –smelly & a powerful insecticide!!!!
2.
4.
=ÎÎ
3.
=ÎÎ
In vacuole
1.
from plants to war: cotton to gun cotton
1846 Swiss chemist Christian
Schonbein in Basel was doing some
chemical experiments in the kitchen of
his home. He spilled a flask containing
nitric + sulfuric acid (konigswasser – a
solution that cleans all glass & mopped
it up with his wife’s cotton apron.
After this he hung it over the hot oven
for a quick dry. Unfortunately for his
marriage the entire apron flared up &
disappeared.
This was the invention of smokeless
powder or gun cotton. Nitrocellulose
plasticized by camphor was used by
Kodak, as a film base in X-ray films
Nitrocellulose (also: cellulose
nitrate, flash paper) is a
highly flammable compound
formed by nitrating cellulose
through exposure to nitric acid
or another powerful nitrating
agent. When used as a
propellant or slow explosive, it
is also known as guncotton.
Plant smells Î sulfur compounds
The most notorious feature of skunks is their anal scent
glands, which produce a mixture of sulfur-containing
chemicals such as methyl and butyl thiols traditionally
called mercaptans, which have a highly offensive smell
strong enough to ward off bears.
Asparagus officinalis (Liliaceae) has strongly reduced leaves.
Asparagus sap is rich in the amino acid L-asparagine which
contributes ot the taste-enhancing umami character. It was
the first amino acid to be isolated in 1806 from asparagus.
Most people observe a distinct odor from their urine shortly
after eaten asparagus. This is caused by organic sulphur
compounds: like methanethiol, dimethyl sulfide, dimethyl
disulfide etc.
Lab exercise: something to behold for the eye: onion
When onions are sliced or eaten, cells are
broken, allowing the enzyme alliinase to break
down amino acid sulphoxides and generate
sulphenic acids.
A specific sulfenic acid, 1-propenesulfenic
acid, is rapidly rearranged by a second enzyme,
to syn-propanethial-S-oxide, a volatile gas
known as the onion lachrymatory factor or
LF.The gas diffuses through the air and
eventually reaches the eye, where it activates
sensory neurons, creating a stinging sensation.
Tear glands produce tears to dilute and flush
out the irritant. Similar Chemicals are known as
lachrymatory agents
cutting onions under running water or
submerged in a basin of water. Another way to
reduce irritation is by freezing, or by not cutting
off the root of the onion which has a higher
concentration of enzymes
Task1:
1. Cut onion while partner holds a
large sheeth of pH (or yellow red
beet) paper to catch flares of sulfenic
acid.
2. Test for active lachrimatory
factor by cutting an onion + bringing
it near your partner’s head
3. Cut onion under slightly alkaline
water pH 9-10 and test again.
Muscone
Muscone is an oily liquid that is found naturally
as the (-)-enantiomer, but synthetic material is
typically a racemate. It is very slightly soluble in
water and miscible with alcohol. Muscone is
the primary contributor to the odor of musk.
The chemical structure was first elucidated by
Lavoslav Ružička. It is a 15-membered ring
ketone with a methyl group in the 3-position
Natural muscone is obtained from the
glandular secretion of the unfortunate musk
deer, which has been abused for perfumery and
medicine for thousands of years. Since
obtaining natural musk required killing the
endangered animal, nearly all muscone used in
perfumery today is synthetic.
muscone
civetone
Female dear & humans are very sensitive to musk smell during ovulation
Plant Smells resemble Animals
In mammals the males use musks as pheromones. Examples are musk
deer, musk ox, civet and the musk rat producing macrocyclic ketones as
well as lactones. Musk lactones – however - are also found in some
plants Musk odorants in plants are always macrocyclic lactones. In animals,
using musk pheromones can be ketones as well as lactones,.
Angelica seeds have several
macrocyclic musks, e.g
15-pentadecanolide
Ambrette seeds contain an oil with a
musky- to-ambery odour. It's major
component istetradecen-14-olide .
Ambrette seeds Abelmoschus moschatus (Malvaceae) come from a tropical
hibiscus. The seeds contain an oil with a fatty-musky, slightly ambery odour:
5(Z)-tetradecen-14-olide & 7(Z)-hexadecen-16-olide, also called ambrettolide.
Now it is largely replaced by synthetic musks, eg. the isomer 9-hexadecen-16olide is made by the Swiss company Givaudan.
Ambrette Seeds
Abelmoschus moschatus (Abelmosk, Ambrette seeds, Annual hibiscus,
Bamia Moschata, Galu Gasturi, Muskdana, Musk mallow, Musk okra,
Musk seeds, Tropical jewel hibiscus, Yorka okra; syn Hibiscus abelmoschus
is an aromatic and medicinal plant in the Malvaceae native to India
Musk mallow seed oil was once
frequently used as a substitute for
animal musk; however this use is
now mostly replaced by various
synthetic musks due to costs. The
seeds are added to coffee; unripe
pods ("musk okra"), leaves and new
shoots are eaten as vegetables.
considered an insecticide & aphrodisiac
Ambrette seeds Abelmoschus moschatus (Malvaceae) come from a tropical
hibiscus. The seeds contain an oil with a fatty-musky, slightly ambery odour:
5(Z)-tetradecen-14-olide & 7(Z)-hexadecen-16-olide, also called ambrettolide.
Now it is largely replaced by synthetic musks, eg. the isomer 9-hexadecen-16olide is made by the Swiss company Givaudan.
flavors and fragrances
limonene in citrus fruits and
menthol in the labiatae
vanillin
discovered as the first
natural flavor in
vanilla pods in 1872
Human Odors
Human odors are produced by the skin's apocrine sebaceous or sweat
glands, developing during puberty These glands are located in 6 areas1:
1) axillae (underarm pits)
2) nipples of both sexes2 3) The
pubic, genital, and circumanal regions 5) The eyelids 6) The outer ear
This would be called part of a pheromonal system in any other mammal.
humans who smell only the bacterial breakdown products of
glandular secretions. Sebaceous secretions themselves consist
mostly of lipids such as squalene and other esters. When
degraded free fatty acids result, that smell unpleasant. The most
prominent examples of hircine fatty acids have the general
formula (CH3(CH2)nCOOH) and are called butyric acid
(n=2), caproic acid (n=4), and caprylic acid (n=6).
While women's have an acute ability to smell musk , the musky odors of
civetone (civet cat), or exaltolide (a synthetic musk), men are relatively
insensitive to these substances. Moreover, women's sensitivity to these
substances varies as a function of their menstrual cycle. Women on the pill,
women who have had ovarectomies, pregnant women, and post-menopausal
women are as insensitive as men.
Sexual “Chemistry” – myth or suppressed reality?
Mate selection is a highly complex process & we are consciously aware
of only part of it; the rest is either unpredictable or operates outside our
awareness, Certainly, there is nonverbal communication between
people: eye contact, smiles, general body language, pheromones, clothes
outward appearances:
Female: low waist-to-hip ratio, full lips, facial features,
Male: broad shoulders, clear skin, masculine facial features
Smell: Women’s preferences for certain male scents and
other male features change over their cycle. Near ovulation,
they prefer masculine traits and musky smells ; at other
phases they prefer stability.
After sex, the brain releases oxytocin, which results in
companionable feeling of love & social bondage. Sex on a
whim can lead to feelings for a person who is wrong for you.
J. Fast M. Bernstein: “Sexual Chemistry: What is it. How to use it.” Pocket Books , N. Y. 1983
Pheromone perfumes – are they the missing link in sexual chemistry?
Although humans generally rate olfaction as their least important sensory
modality, they spend billions of dollars, years of their effort to modify the way
they smell
In humans the main odor-producing
organ is the skin. Odors are largely
produced by the skin's apocrine
sebaceous glands, which develop during
puberty & are associated with sweat
glands and tufts of hair.
Pherone
Formula M-11
Pheromone
Cologne for
Men to Attract
Women, with
5mg of Human
Pheromones
Perfumes - mimicking undiscovered pheromones?
Perfumes were made in India & Egypt more than 5000 a ago. Chinese & Japanese made scent
clocks burning different odors for the times of day! Perfumes were royal gifts (see Jesus birth)
Since “per fume” = through air you need fixatives (balsams & resins) to
prevent rapid exhaustion of volatile substances called odorants:
1. Concretes (alcoholic extract with removed of alcohol), 2. absolutes, 3.
distilled oils, 4. expressed oils, 5. Tinctures (civet, castoreum, musk)
Perfume = costliest fragrance with 22% essential oils.
Eau de Parfum between 15 and 22% essential oils.
Eau de Toilette (EDT) with 8 to 15% oils.
Eau de Cologne has just 4% essential oils.
Eau Fraiche has 1 to 3% essential oils, is the lightest
plants include anise, bay leaf, bergamot, cardamom, cedar wood, rose,
eucalyptus, frankincense, gardenia, geranium, iris, jasmine, lavender, lemon,
lilac, lily, lily of the valley, magnolia, moss, neroli, orange, orris, patchouli,
pine, raspberry, sage, sandalwood, tuberose, vanilla, violet and ylang-ylang.
animal products include musk from the male musk deer, ambergris
from sperm whales, castoreum a secretion of the beaver and civet
from the civet cat. All are used as fixatives & add mystery to smell
Famous Perfumes
Ernest Beaux created Chanel No. 5 for Coco Chanel in
1921. It has a floral top note of ylang-ylang and neroli,
with a heart of blends of jasmine and rose all above a
woody base of sandalwood and vetiver.
Guerlain's Shalimar launched first in 1925 & relaunched
in 2001. It's a refined oriental feminine fragrance with
iris, vanilla, and rose - a truly sense hitting perfume
1944 saw the introduction of Femme by Rochas. In
1947 Dior launched the ever popular Miss Dior. Max
Factor's Hypnotique and Primitif were popular in
1950s 4711 Eau de Cologne, with its 4711 roll on stick
was especially popular for summer heat perspiration
1977 Yves St. Laurent put 'Opium' perfume in
production huge success with women- a perfume for
sultry evenings.
in the 80s blatant erotic advertising led to the success of
the 1985 Obsession from Calvin Klein. Obsession with
its heavy smell of vanilla was dominant in the market.
Human Pheromones –sure!
Q. Is there any evidence to show that Pheromones are
effective in attracting women?
A: There is plenty of evidence. With the advances in science, the
evidence that pheromones are effective in attracting women is
growing rapidly. Pherlure commercial
"and this pretty sales person walked up and asked if i
need anything and i said just looking and the next thing i
know shes asking me what my phone number was and
what i was doing later tonight......... WOW!!!!!!!!!!! this
stuff is great." RJ, IL
Spices and perfumes – driving forces of human history
In ancient Near Eastern cultures fragrances and spices were used to preserve meat
including human corpses.
Also Egyptian girls used fragrant perfume cones (animal grease) to have a shortdistance effect on the Old Egyptian male. Together with the dress it was devastating.
Perfumes Î tradition or requirement?
Perfume is a mixture of fragrant essential oils and other
odorants, fixatives, and solvents used to give the human body,
animals, objects, and living spaces a pleasant smell.
History: The word perfume derives from Latin "per fumum",
meaning through smoke. Art of making perfumes began in
ancient Mesopotamia, Egypt, Rome &Persia. Ancient East
Asian fragrances were more incense based. The world's oldest
perfumery was in Pyrgos (Cyprus) 4,000 years old perfumes,
60 stills, mixing bowls, funnels and perfume bottles.
The Persian Muslim doctor & chemist Avicenna ( Ibn
Sina) first described the process of extracting oils from
flowers by means of distillation. He discovered liquid
perfumes as mixtures of oil and crushed herbs or petals.
Hungary water was the first European, alcohol-based perfume,
made by court alchemists in the late 1300s from distilling fresh
rosemary (and possibly thyme) with strong brandy, later
additions were lavender, mint, sage, marjoram, costus, lemon.
Aromas & Aromatherapy
1732 Farina in French-occupied Cologne made blend of neroli,
bergamot, lavender & rosemary in grape distil. Î Eau de Cologne
– Napoleon used several bottles a day
1939 Dr. Jean Valnet of the French Army used thyume , clove &
lemon oil for wound treatment & later for psychological treatment
Î the re-birth of the cure by fragrances (which indeed are a
carrier of emotional memory, easy for induced Pavlov reflexes)
Substances in essential oils: lipophilic terpenes, phenols,
esters, aldehydes etc.
Example: Thyme oil:
principal constituents are thymol
(antiseptic) , carvacrol (antiseptic to toxic), cymene, terpinene,
camphene, borneol, linalol, menthone, citral, geraniol, thujanol
used in mouthwash like Listerine brand , make your own:
(3 drops of thymol oil into one ounce of water plus tincture of
Oregon grape! Or other astringents like menthol)
Hydrosols – holograms of plant essence? *
Watery solution, also hydrolate (water milk french), floral water
= condensate water produced during distillation of plant material
for aromatherapy - a form of phytotherapy
Plant materials used to extract essential oils
Flowers: roses, carnations, orange, violets, lavender
Shoots:
mints, rosemary, geranium, citronella, lemon gr
Seeds/fruits:
oranges, lemons, nutmeg
Roots:
sassafras
Wood:
cedar, sandalwood, pine
Gums:
balsam, myrrh
Bark:
cinnamon, cassia
* Catty, S. “Hydrosols; the next aromatherapy” Healing Arts
Press Rochester Vermont, 2001
What the smell of Essential Oils reveals about the ingredients
An essential oil is a mixture of many terpenes plus other volatile
substances turn into gas molecules at room temperature & ar easily distilled
Aniseeed Pimpinella anisum =
trans anethole (75-90 %)
Basil Ocimum basilicum =
linalol (50%), methyl chavicol (25%) etc.
Bay laurel Laurus nobilis = cineol (40 %), pinene, linalol, meth eugenol
Benzoin Styrax benzoin =
coniferyl cinnamate, benzoate, cinnamic ac
Calamus Acorus calamus =
beta-asarone (80 %), oral toxin
Camphor Cinnamonum camphora = cineole (75-95 %), pinene,
Caraway Carum carvi
carvone (60 %), limonene (40%)
cinnamon Cinnamonum zeylandicum eugenol 95%
Wormwood Artemisia absinthium =
71 % thujone, azulene, terpenes
Ylang-ylang Cananga odorata =
methyl & acetyl benzoate, methyl
salicylate, eugenol, geraniol, linalol, terpenes: pinene, cadimene
Some essential oils are not oils at all
esters “oil of Wintergreen” Gaultherai procumbens = methyl salicylate 98 %)
oil of tonka beans Dipteryx odorata = 99 % coumarins = phenolic compounds
garlic Allium sativum allicin, allyl propyl disulphide, citral, linalol
Essential = Fragrant Oils are healing mind & body
Aromatic plants are easily recognized & are used by animals and people for millions of years.
They were soon part of rituals: juniper sprigs are burnt in Tibetan Temples, frankincense in
Roman Catholic Church, Gum Benzoin in Greek & Russian Orthodox Church.
Essential oils are the key components for aroma, taste and flavor in perfumes,
spices, & condiments.
Essential ( misleading term = not like essential amino acids or fatty acids; i.e. a
substance we absolutely require for health but cannot produce) from the distilled
alchemical essence of plants), volatile, fragrant oils. Lipophilic substances taken up
through nose & skin with twofold action: psychological and physiological effects.
Î Aromatherapy is healing mind & body : fragrant oils provide more than aroma
Essential oils are products of steam distillation, mechanical processing of citrus rinds or dry
distillation of natural materials. Essential oils are physically separated from the water phase.
Aromatherapy: established by Rene-Maurice Gattefosse in 1920s, popularized by Dr.
Jean Valnet 1964 with strong reductionist emphasis on pharmacological ingredients,
1978 Paul Belaiche Î 3 volumes on Clinical Use of Aromatherapy for infections etc. :
oils for medicinal use must be genuine ( = unchanged) & authentic (from one plant)
Julia Lawless (1992) The encyclopedia of essential oils. Barnes & Noble BooksN.Y.
Roszak, Theodore (1994) Eco-psychology – voice of the earth. Stuttgart
Antibacterial effects of Fragrant Oils
As Gattefosse demonstrated already during WWI: Fragrant oils are antibiotica as strong
as penicillin – a remedy developed during WW II.
Geraniol: effective
against Candida
yeast
Thymol:
knocks out
Micrococcus flavus
Staphylococcus
aureus, epidermitis
E. coli,
Bacillus subtilis
Geraniol,
thymol &
many other
ingredients
are found in
thyme oil etc.
Paul Belaiche (1978) Phytotherapie et d’Aromatherapie (3 volumes). Paris
Antimicrobial effects of Fragrant Oils
Bactericidal components in essential oils:
Monoterpenes in oils of Tea tree, Niaouli, Eucalyptus radiata, Ravensare aromatica
Phenols in oils of Thyme, Oregano, Mountain savory
Fungicidal components in essential
oils:
Esters in oils of Lavender, Roman chamomile,
Geranium, aldehyde from Cinnamon
Mucolytic components in essential
oils:
Ketones in oils of Eucalyptus dives, Rosemary,
Lactones in Inula graveolens
brochodilatory components in
essential oils:
Terpenes in oils of Pine, Cypress, Hazelnut ,
rubbed on chest for relieve
Paul Belaiche (1978) Phytotherapie et d’Aromatherapie (3 volumes). Paris
Resins –purifying incenses of old
Mastic is the resin Pistacia lentiscus growing in only
a few villages of the island of Chios. Wounded
Pistachio trees have resin flow in August. is chewed
like chewing gum. Î word masticate, trad. Greece
Gum Benzoin is resin produced by the tall Styrax trees (S. benzoin
& S. tonkinense) native to Indochina, also called the Java incense
trees growing no taller than a person. Gum benzoin was used in
Chinese perfumes due to its stable aroma, also in massage oil. The
wounded bark fills with yellow fluid that hardens into a reddish mass.
Gum guggul myrrh –like resin from the Iranina thorn tree Commiphora
mukul, native to western Iran and Eastern India, perfume of Persian women at
the time of Alexander’s conquest..
Balsam of Gilead, Balm of Mecca. Resin from 3 m tall trees
of Commiphora opobalsamum native to Southern Yemen,
kingdom of Saba (queen of Sheba’s gift to Solomon), later
planted from Egypt to Palestine, remedy for ringworm + skin
diseases. B of Gilead from N. American Populus candicans Î
Resins –purifying incenses of old
Sandalwood: from wood and root of parasitic trees
Santalum album, wounding causes gum to flow Î
pure native to Indonesia and India. 1000 BC use in
India as incense, perfume to enhance sexual attraction
(sandalwood resembles male pheromone) and in oil
paste applied as UV-protecting sunscreen!
Red Sandalwood gives red powder like Santalum but lacks
aroma. derived from different trees Pterocarpus santalina that
form forests in Madagascar. Decorative wood for pagodas, statues
etc. , spice in marzipan & biscuits.
Aloeswood resin from tree Aquilaria mallantis native to Eastern has
black hard dense wood. Muslim kingdom of Champa (South Vietn)
Chinese med. uses it for nervousness, Ayurveda for mental illness.
Myrrh reddish-brown resin from dried sap of tree Commiphora
myrrha, native to Yemen & Somalia (Punt). Unlike other resins,
myrrh expands and "blooms" when burned instead of melting or
liquefying .not related to Myrrhis odorata = sweet cicely
Asafoetida – the ersatz Silphium of Greek antiquity
Asafoetida = Europe’s forgotten spice?
from Iran – a repulsively smelling resin
from the Iranian Fennel Ferula asafoetida often adulterated with F. persica
& F. galbanum – all tall stout umbellifers
The secret of it was first discovered by
German botanist Engelbert Kaempfer
who travelled in Iran & Turkey under
cover and wrote 1712 “Five studies of
exoticwonders, political,
scientific and medical”
How to make Incense!
Incense (incendere, "to burn") is composed of aromatic biotic materials, which release
fragrant smoke when burned. Many religious ceremonies employ incense, preparing a
clean air for the gods.
Making Incense needs four basic ingredients:
- an aromatic substance: any herb with a pleasant smell
- a bonding agent to hold cones and cylinders together (base)
- a solvent for the bonding agent
- a substance that supports controlled burning of the cone
Combustible base The combustible base of a direct burning incense mixture not only
binds the fragrant material together but also allows the produced incense to burn with a
self-sustained ember, which propagates slowly and evenly through an entire piece of
incense with such regularity that it can be used to mark time. The base is chosen such
that it does not produce a perceptible smell. Commercially, two types of incense base
predominate:
•Fuel and oxidizer mixtures: Charcoal or wood powder forms the fuel for the
combustion. Gums such as Gum Arabic or Gum Tragacanth are used to bind the
mixture together while an oxidizer such as Sodium nitrate or Potassium nitrate
sustains the burning of the incense. Fragrant materials are combined into the base
prior to formation as in the case of powdered incense materials or after formation
How to make Incense!
Making Incense needs four basic ingredients:
- an aromatic substance: any herb with a pleasant smell
- a bonding agent to hold cones and cylinders together (base)
- a solvent for the bonding agent
- a substance that supports controlled burning of the cone
Common raw incense making materials
Makko powder (Machilus thunbergii),
Borneol camphor(Dryobalanops aromatica),
Sumatra Benzoin (Styrax benzoin),
Omani frankincense (Boswellia sacra),
Guggul (Commiphora wightii),
Golden Frankincense (Boswellia papyrifera),
Tolu balsam (Myroxylon toluifera),
Somalian myrrh (Commiphora myrrha),
Labdanum (Cistus villosus),
Opoponax (Commiphora opoponax),
white Indian sandalwood powder (Santalum
album)