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PHARMACOGNOSY II
PHAR306
6th Semester
1st Lecture
Prof. Dr. Müberra Koşar
Eastern Mediterranean University
Faculty of Pharmacy
Department of Pharmacognosy
INTRODUCTION
ESSENTIAL OILS
(VOLATILE OILS / ETHEREAL OILS / AETHEROLEA)
• are volatile in steam,
• chemical and physical properties are different from fixed oils.
• are secreted in oil cell, in secretion ducts or cavities or in
glandular hairs
• are frequently associated with other substances (gums, resins
etc.)
• are separated from the aromatic plants as a mixture of
terpenes.
INTRODUCTION
• EOs are found in these organs of plants;
– glandular hairs
– glandular pockets
– glandular channels
– parenchyma cells that are undergone changes
• EOs are found in these parts of plants;
– fruit (Apiaceae)
– pericarp (Rutaceae)
– petals (rose)
– leaf
– bark
– root
INTRODUCTION
COMPOSITION of ESSENTIAL OILS
• terpenic compounds
– acetate-mevalonate pathway
• aromatic compounds
– shikimic acid pathway
• others
– straight chain hydrocarbons
– nitrogen and sulphur bearing compounds
INTRODUCTION
USE of ESSENTIAL OILS
• in treatment (eucalyptus oil)
• as flavor (lemon oil)
• in perfumery (rose oil)
• as starting material for the synthesis of some compounds
(turpentine)
• as antiseptic preservative (oregano oil-high phenol content)
• antispasmodic (ginger, thymian, mint, chamomile oil)
• aromatherapy
TERPENES
THE ROLE of TERPENES in PLANTS
• help pollination
fragrant/aromatic terpenes (volatile terpenes) makes plant attractive 
pollination
• protective
some of the less volatile and strong bitter terpenes prevents other animals
to eat the plants  antifeedant (any substance that inhibits normal
feeding behaviour)
• phytohormone
another group of terpenes play a role as growth regulators
TERPENES
TERPENES
• isoprene are molecular hydrocarbonds (2-methyl-1,3-
butadiene) with (C5H8)n structure
• isoprene units are linked together in the form  head-to-tail
(isoprene rule) oxygenated, hydrogenated and
dehydrogenated derivatives are called terpenoids
(isoprenoids)
TERPENES
• Otto Wallach (1847-1931)
• have worked on essential oils
• defined „isoprene rule“
• won a Nobel Prize in 1910 in
chemistry
TERPENES
ISOPRENE RULE
• myrcene is formed by the linkage/connection of head-to-tail
binding of isoprenes
TERPENES
ACCORDING to the NUMBER of ISOPRENE UNITS
• hemiterpenes C5
• monoterpenes C10
• sesquiterpenes C15
• diterpenes C20
• sesterterpenes C25
• triterpenes C30
• sesquarterpenes C35
• tetraterpenes C40
• polyterpenes Cn
TERPENES
HEMITERPENES
isoprene prenol
isovaleric acid isovaleramide
MONOTERPENES
ACYCLIC
MONOCYCLIC
BICYCLIC
hydrocarbon alcohol aldehyde
hydrocarbons
alcohols
aldehydes
ketones
oxides
sabinane type pinane type camphane type carane type fenchane type
TERPENES
TERPENES
I. ACYCLIC MONOTERPENES
a. Hydrocarbones
myrcene ocimene
TERPENES
I. ACYCLIC MONOTERPENES
b. Alcohols
linalool geraniol citronellol
TERPENES
I. ACYCLIC MONOTERPENES
c. Aldehydes
citral citronellal
TERPENES
II. MONOCYCLIC MONOTERPENES
a. Hydrocarbones
limonene a-phellandrene b-phellandrene
TERPENES
II. MONOCYCLIC MONOTERPENES
b. Alcohols
menthol a-terpineol
TERPENES
II. MONOCYCLIC MONOTERPENES
c. Aldehydes
phellandral perillaldehyde safranal
TERPENES
II. MONOCYCLIC MONOTERPENES
d. Ketons
pulegone carvone
TERPENES
II. MONOCYCLIC MONOTERPENES
d. Oxides
eucalyptol
TERPENES
III. BICYCLIC MONOTERPENES
a. Sabinane Type
sabinene a-thujene
TERPENES
III. BICYCLIC MONOTERPENES
b. Pinane Type
a-pinene b-pinene
TERPENES
III. BICYCLIC MONOTERPENES
c. Carane Type
3-carene carone 4-carene
TERPENES
III. BICYCLIC MONOTERPENES
d. Camphane Type
camphor borneol
TERPENES
III. BICYCLIC MONOTERPENES
e. Fenchane Type
fenchane
TERPENES
SESQUITERPENES
a-bisabolol b-bisabolol b-caryophyllene
TERPENES
SESQUITERPENES
cadinene santonine farnesol
TERPENES
TERPENES
TERPENES
TERPENES
OCIMENE
• Ocimum basilicum
• Origanum sp.
• Mentha sp.
• Salvia sp.
TERPENES
MYRCENE
• Laurus nobilis
• Cymbopogon sitratus
• Thymus sp.
• Ylang ylang
• Humulus lupulus
• Petrocelinum sp.
TERPENES
CITRAL
• Backhausia citriodora
• Litsea citrata
• Cymbopogon citratus
• Ocimum sp.
• Lindera sp.
• Citrus aurantium var. amara
• Eucalyptus sp.
• Citrus sp.
TERPENES
CITRONELLAL
• Melissa officinalis
• Cymbopogon sp.
• Eucalyptus citriodora
TERPENES
LINALOOL
• Lamiaceae
• Lauraceae
• Rutaceae
• Ocimum sp.
• Artemisia sp.
TERPENES
GERANIOL
• Rosae oleum
• Cymbopogon martini
TERPENES
CITRONELLOL
• Rosae oleum
• Cymbopogon martini
• Pelargonium sp.
TERPENES
a- and b-PHELLANDRENE
• Eucalyptus sp.
• Ferula communis
• Abies balsamea
TERPENES
PULEGONE
• Mentha pulegium
• M. piperita
• Nepeta cataria
TERPENES
CARVONE
• Carum carvi
• Anethum graveolens
TERPENES
α-TERPINEOL
• Melaleuca sp.
• Pinus sp.
• Citrus aurantium var. amara
TERPENES
EUCALYPTOL (1,8-cineol)
• Eucaliptus sp.
• Cinnamomum sp.
• Laurus nobilis
• Artemisia vulgaris
• Salvia sp.
• Cannabis sativa
TERPENES
SESQUITERPENES
• acyclic (a-farnesene, farnesol)
• monocyclic (bisabolol, bisabolene)
• bicyclic azulene and naphthalene derivatives
• hernandulcin: a non-calorie sweetener
• gossypol: is obtained from cotton. Antimitotic and Chinese men uses in
the traditional art for medication as birth control
TERPENES
DITERPENES
abietic acid phytol
TERPENES
DITERPENES
• Montana tomentosa: zoapatanol; birth control
• Stevia rebaudiana: stevioside, rebaudioside; sweetener
• Rabdosia rubescens: oridonin, lasiokaurin; cytotoxic
• Salvia dividonum: salvinorin; hallucinogen
• Salvia miltiorrhiza: quinones; heart diseases and antioxidant defenses.
• Sideritis mugronensis: boryatrol; anti-inflammatory, analgesic
• gibberellin: plant hormones
TERPENES
• Coniferae: abietic acid; pests and pathogenic molecules
• Taxus baccata and T. brevifolia: Taxol; mitosis inhibitor-antitumoral
• Docetaxel (Taxotere®): type of chemotheraphy drug
• Paclitaxel (Anzatax®, Taxol®): metastatic ovarian cancer and breast cancer
TERPENES
• Teucterium sp.: teuflavoside; antiulcer
• Scutularia sp.: skutellon A-D, skutellon A-D, skutallisin,
skutorientalin; lung, liver and rectal tumors
• Laurencia obtusa: laurensianol; antibiotic
• Corals: sinullarin; antitumoral
TERPENES
TRITERPENES
bilabolid
betunilic acid
TERPENES
• Betula sp.: Betulinik asit; melanoma
• Aesculus hippocastanum: escin; anti-inflammatory
• Ruscus aculeatus: ruscogenin, ruscoside, ruscin; venous
insufficiency
• Glycyrrhiza glabra: antiulcer
• Hedera helix: α-hederin; antihelmentic
• Quillaja saponaria: immunomodulator; chemotheraphy and
transplantation
• Panax ginseng: adaptogenic
TERPENES
• Agave sp.:Diosgenin,heoxgenin
• Similax sp.: similagenin, sarsapogenin
• Glycine soja: stigmasterol, sitesterol
• Spirasolans

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Chapter 1.pdf ,,,,,,,,,,,,,,,,,,???????????