PHARMACOGNOSY AND PLANT CHEMISTRY LECTURE

Central Philippine University – College of Pharmacy- Second Semester- PRELIMS

TRANSCRIBED BY: Chan, K.E

TYPES OF MONOTERPENES
VOLATILE OIL
Types:
• ethereal oil or essential oil
• odorous 1. acyclic (linear) monoterpenes- ex: mercenes,
• evaporate when exposed to the air geraniol, citral, citronellal, citronellol, linalool, halomon
• colorless 2. monocyclic monoterpenes - ex: limonene, p- cymene,
• immiscible with water menthol, thymol, carvacrol
• soluble in alcohol and other organic solvents 3. bicyclic monoterpenes - ex: pinene, carene, sabinene,
• high refractive indices camphene, thujone, camphor, borneo, eucalyptol

SPECIALIZED SECRETORY STRUCTURES FOUND IN

SESQUITERPENES
PLANT PART S
• a class of terpenes that consist of 3 isoprene units
• glandular hairs – Labiatae • molecular formula C15H24
• modified parenchymal cell - Piperaceae
• oil tubes (vittae) – Umbelliferae Types:
• lysigenous/schizogenous passages - Pinaceae,
Rutaceae 1. acyclic - ex: farnesene
2. monocyclic - ex: zingiberene, humulene
OTHER PLA NT PARTS THAT CONTAIN VOLATILE OILS 3. bicyclic - ex: cardinenes, caryophyllene
4. tricyclic - ex: longifolene, copaene, patchoulol
• petals - rose
• bark and leaves - cinnamon AROMATIC COMPOUNDS
• pericarp - umbelliferous fruits " glandular hairs - mints
• rind - orange • these are compounds that consists
o volatile may be formed directly by the protoplasm, of 1 or more rings that contains
by decomposition of the resigenous layer of the cell alternating single and double bonds
wall, or by the hydrolysis of certain glycosides. in its chemical structure.

CHEMICAL CONSTITUENTS

Terpene derivatives - formed via the acetate- mevalonic acid

pathway. PHENYLPROPANOID
• another major group of volatile oil constituents
Aromatic compounds - formed via the shikimic acid- • they contain the C6 phenyl ring with an attached C3
phenylpropanoid route
propane side chain
ex: phenols, phenol ethers
CHEMISTRY OF VOLATILE OILS
• stereoptenes

ex: present in small quantities

TERPENES
• Natural products whose METHODS OF OBTAINING VOLATILE OILS
structures are divided into
isoprene units. 1. Distillation
a) water distillation
b) water and steam distillation
c) direct steam distillation
2. Expression
MONOTERPE NES
a) sponge process
• Composed of 2 isoprene units b) ecuelle method
• Molecular formula C10H16 c) machine process
• They can occur in acyclic, monocyclic, and bicyclic,
forms as hydrocarbons an as oxygenated derivatives
such as alcohols, aldehydes, ketones, phenols, oxides
and esters.

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 PHARMACOGNOSY AND PLANT CHEMISTRY LECTURE
Central Philippine University – College of Pharmacy- Second Semester- PRELIMS
TRANSCRIBED BY: Chan, K.E

3. Extraction ➢ Extracts- concentrated preparations of vegetable or

animal drugs obtained by removal of the active
a) maceration constituents of the respective drugs with suitable
b) percolation menstrua, evaporation of all or nearly all of the solvent
c) digestion and adjustment of the residual masses or powders to the
d) infusion prescribed standards (USP)
e) decoction ➢ Menstruum- solvent used for extraction
➢ Marc- the inert fibrous and other insoluble remaining
4. Enzymatic hydrolysis after extraction.

5. Enfleurage
6. Destructive distillation
DISTILLATION
▪ water distillation - applied to plant material that is
dried and not subject to injury by boiling. ex: turpentine
▪ water and steam distillation - employed for either
dried or fresh substances that maybe injured by boiling.
ex: cinnamon, clove
▪ direct steam distillation - applicable to fresh plant
drugs. ex: peppermint, spearmint
EXPRESSION
• this method produces the most fragrant product because
there are few volatile oils whose aroma is not injuriously
affected by the action of heat.
ex: citrus family (orange, lemon, bergamot, lime)
EXTRACTION
MACERATION
• the plant is placed in a closed container with the
extracting solvent and allowed to stand at room
temperature for a period of time (3 to 7 days) with
frequent agitation.
• the mixture then is filtered, the marc is pressed.
• the combined liquid are clarified by filtration or
decantation
PERCOLATION
• in this method, the material in a well- ›closed container is
subjected to a slow flow of fresh solvent at intervals until
sufficient active ingredient is extracted(4 hours)
DIGESTION
• a form of maceration which gentle heat is used during
the process of extraction.
• it is used when moderately elevated temperature is not
objectionable and the solvent efficiency of the
menstruum is increased thereby.

PRINCIPAL METHOD OF EXTRACTION:

INFUSION
• Maceration Percolation • the plant material is placed in a pot and ›wetted with
• Digestion cold water.
• Infusion • boiling water is poured over it, then left to stand.
• Decoction • it is then covered with a lid for about 15 minutes after
➢ Involves the separation of medicinally active portions of which the crude drugs is poured off.
plants or animal tissues from the inactive or inert
components by use of selective solvents in standard DECOCTION
extraction procedures.
• the crude drug is boiled in a specified volume of water
for a defined time.
• Then cooled and filtered.
• this procedure is suitable for extracting soluble, heat
stable plant constituent

ENZYMATIC HYDROLYSIS
• The volatile oil is obtained by hydrolysis with enzymes

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 PHARMACOGNOSY AND PLANT CHEMISTRY
Central Philippine University – College of Pharmacy- Second Semester- PRELIMS
TRANSCRIBED BY: Chan, K.E
ENFLUORAGE
• Often used in the production of volatile oil ›content of
fresh plant parts which are so small.
• An odorless, bland, fixed oil or fat is spread in a thin
layer on glass plates. The flower petals are placed on the
fat for a few hours.
• After the fat has absorbed as much fragrance, the oil is
then removed by extraction with alcohol.
DESTRUCTIVE DISTILLATION
• Is a means of obtaining empyreumatic oils.
• This dry distillation process is used in the production of
volatile oils from wood or resin
Ex: members of family Pinaceae and Cupressaceae
LECTURE
• beta myrcene - very rare acclic monoterpene
hydrocarbons found in myricia, lemon, myristica oils
• cadinene - occurs in juniper tar, a typical
sesquiterpene hydrocarbon
• beta caryophyllene – a bicyclic sesquiterpene
found in wormwood, peppermint, cinnamon, clove
oils
TURPENTENE OIL
• Spirits of turpentine
• A volatile oil drug chiefly of hydrocarbons
Source: oleoresin of Pinus palustris, Fam. Pinaceae that yields
terpene oils exclusively
Uses: counterirritant, expectorant, stimulant to mucous
membrane

PHARMACEUTICAL USES ALCOHOL VOLATILE OI L

• FLAVOURING AGENT • Acyclic alcohols (that are terpene derivatives)
• PERFUMING AGE o ex: geraniol, linalool, citronellol
o Pharmaceutical Formulations • Monocyclic alcohols
o ex: menthol, alpha terpineol
o Foods
• Dicyclic terpene alcohols
o Beverages o ex: borneol (from Borneo camphor)
o Cosmetic Industries • Sesquiterpene alcohols
• MEDICINAL AGENT o ex. zingiberol
• PEPPERMINT - dried leaf and flowering top of Mentha
Carminative Local Anesthetic piperita
Anthelmintic Sedative
Diuretics Local irritant Fam. Labiatae
Antiseptic Insect Repellant
Insect repellent Source of Vit. A constituent: volatile oil, resin, tannin

CLASSIFICATION OF VOLA TILE OILS uses: flavor (chewing gum), carminative. stimulant. &
counterirritant
1. hydrocarbons 5. phenols
2. alcohols 6. phenolic ethers DRUG SOURCES:
3. aldehydes 7. oxides
4. ketones 8. esters • cardamon oil
• corander oil
• rose oil
HYDROCARBON VOLATILE OIL • orange flower
• limonene - the most widely • juniper oil
• pine oil
distributed of the monocyclic
• peppermint oil
terpenes. occurs in: citrus,
thyme, mint, myristica,
caraway, cardamom, ALDEHYDE VOLATILE OILS
coriander • acyclic aldehyde
• p-cymene - found in o ex: citral (mixture of geranial, neral &
coriander, thyme, cinnamon, citronellal)
myristica oil • cyclic or aromatic includes cinnamaldehyde and vanilin
• pinene - a dicyclic monoterpene found in conifer (vanilla, benzoin, tolu, Peru balsams)
oils, lemon, anise, eucalyptus, thyme, fennel,
coriander, orange flower, myrstica oil.
• sabinene- a dicyclic monoterpene of the Thione
class found in cardamom, lemon oils

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 PHARMACOGNOSY AND PLANT CHEMISTRY LECTURE
Central Philippine University – College of Pharmacy- Second Semester- PRELIMS
TRANSCRIBED BY: Chan, K.E
• SPEARMINT -dried, leaf and flowering, top of Mentha
DRUG SOURCES: spicata, M. viridis, M. cardiaca

• cinnamon Fam. Labiatae constituents: resin, tannin, volatile oil that

• cinnamon oil contains carvone
• orange oil
• lemon pec elemon oil uses: flavor, carminative
• hamamelis water
• citronella oil DRUG SOURCES of KETONE VOLATILE OIL:
• CINNAMON - or Saigon cinnamon is the dried bark of
Cinnamomum loureirii • Camphor
Fam. Lauraceae • spearmint
• caraway
constituents: volatile oils, mannitol, tannin uses: flavor
• buchu
and carminative • wormwood
• LEMON PEEL - the outer yellow rind of the fruit of • cedar leaf
Citrus limon,
Fam. Rutaceae constituents: volatile oil hesperidin, bitter
PHENOL VOLATILE OILS
principle, calcium oxalate
uses: flavor, stimulant, stomachic 2 kinds of phenols that occurs in volatile oils:
• Lemon oil - the volatile oil obtained by expression,
without the aid of heat, from the fresh peel of the fruit of 1. those that are PRESENT NATURALLY
C. limon, with or without the previous separation of the 2. those that are PRODUCED as the result of destructive
pulp and the peel. distillation of certain plant products.
constituents: 90% terpenes chiefly limonene;
monoterpene hydrocarbons: beta pinene and alpha thymol & carvacrol- the most important phenols in volatile oils
terpinene; citral
use: flavor, stimulant, carminative, stomachie o Thymol - a phenol obtained from:

neral and geranial (citral) - the most important contributors to 1. thyme oil - Thymus vulgaris
lemon oil flavor.
2. horsemint oil- Monarda punctata, Monarda didyma
neryl and geranyl acetates - the primary esters in lemon
3. ajowan oil- Carum copticum
note: lemon oil that has a terebinthinate odor must not be
used or dispensed, such an odor indicates decomposed terpenes 4. synthetically prepared from m-cresol or p-cymene
or added turpentine oil
2 ways of treating the oil to obtain thymol crystals:
6 PROCESSES UTILIZED IN THE RECOVERY OF OIL OF
LEMON 1. it maybe subjected to freezing temperatures causing
the thymol to crystallize.
• grating
• sponge process 2. it maybe treated with sodium hydroxide solution
• ecuelle e piquer
• machine process uses: antifungal, antibacterial, employed topically in lotions,
• cold pressed creams, and oint.
• distillation
Phenol volatile oil drug sources:

KETONE VOLATILE OI LS • thyme

• myrcia oil
• Monocyclic terpene ketones • creosote
o Ex. Menthone, carvone, piperitone, pulegone, • juniper tar
diosphenol (crystalline ketone in buchu) • pine tar
• Dicyclic ketone • clove
o Ex. Camphor, fenchone, thujone o CLOVE - from dried flower bud of Eugenia
o CAMPHOR - a ketone obtained from caryophyllus
Cinnamomum camphora, Fam. Myrtaceae
Fam. Lauraceae
uses: topical antipruritic, rubefacient, and anti- constituents: gallotannic acid, oleanolic acid
infective eugenin
synthetic camphor- is made from pinene
(turpentine) uses: flavor, Carminative

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 PHARMACOGNOSY AND PLANT CHEMISTRY LECTURE
Central Philippine University – College of Pharmacy- Second Semester- PRELIMS
TRANSCRIBED BY: Chan, K.E

o Formation of methyl salicylate (Hydrolyzed w/

PHENOLIC ETHER VOLATILE OIL gaultherase)
• anethole & safrole - more important phenolic ether
gaultherin + water saliculate → methyl salicylate
volatile oil
• phenolic ether volatile oil sources:
o fennel
o anise
o Star anise
o Nutmeg
NUTMEG - or myristica is the dried, ripe seed
of Myristica fragrans
Fam. Myristicaceae
constituents: safrole, & myristicin
uses: flavor and condiment

OXIDE VOLATILE OILS

• EUCALYPTUS OIL - from the dried, scythe-shaped leaf
of Eucalyptus globulus
Fam. Myrtaceae
constituents: 70-85% cineole (or eucalyptol, also called
cajuputol because it occurs in cajuput), phellandrene,
piperitone
uses: flavor, antiseptic, diaphoretic, expectorant

ESTER VOLATILE OIL

most common esters that occur in volatile oils:

o acetates of terpineol
o acetates of borneol
o acetates of geraniol
o allyl isothiocyanate (in mustard oil)
o methyl salicylate (in wintergreen oil)

Ester volatile oil drug sources:

• lavender
• pine needle
• mustard
• gaultheria
o GAULTHERIA - wintergreen, teaberry or
checkerberry.
Gaultheria procumbens, Fam. Ericaceae
the odor is distinct and aromatic
the taste is aromatic and astringent
constituents: methyl salicylate
uses: flavor for aromatic cascara sagrada
fluidextract, local irritant, antiseptic, antirheumatic
• Methyl salicylate - maybe produced:

1. synthetically

2. maceration with subsequent distillation with steam

from the leaves of G. procumbens or from the bark of
Betula lenta

other names: gaultheria oil, wintergreen oil, betula oil, or sweet

birch oil

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