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Pharmacognosy & Pharmaceutical Biology > Terpenoids > Flashcards

Terpenoids Flashcards

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1
Q

terpenoids are also known as

A

isoprenoids

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2
Q

terpenoids are produced from acetyl coenzyme A using which metabolic pathway

A

mevalonic acid

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3
Q

most important groups of terpenoids include

A

sesquiterpenoids (C15)and monoterpenoids (C10)

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4
Q

sesquiterpenes and monoterpenes often used as (3)

A
  • flavoring agents or in perfumes
  • monoterpenes active constituents in oral products and disinfectants
  • sequiterpene lactones - anti-cancer agents
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5
Q

volatile monoterpenes and sesquiterpenes are derived from

A

volatile oils extracted from plants

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6
Q

terpenoids in nature occur as

A

complex volatile oil mixtures

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7
Q

terpenoids are isolated from (5)

A
  • specialized oil cells
  • oil cavities - schizogenous or lysigenous
  • glandular hairs - libiatae
  • modified parenchyma cells
  • oil tubes
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8
Q

in conifers oil is produced in which tissues

A

all tissues

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9
Q

the structural variation of terpenoids is due to

A

different folding patters or cyclization

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10
Q

terpenoid oils that occur in nature are a complex mixture of

A
  • hydrocarbons and oygenated terpenoid derivatives
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11
Q

volatile oils are classifed according to the nature of the

A

terpenoid constituent

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12
Q

name the terpenoid consituent for each oil name below:

  • hydrocarbon containing (Turpentine)
  • alcohols (monoterpenes) - Corriander & Geranium
  • aldehydes (mono terpenes) - lemon grass
  • ketones (monoterpenes) - spearmint
  • ethers (monoterpenes) -eucalyptus
A
  • Turpentine - pinenes; camphene
  • Corriander & Geranium - linalol; geraniol
  • lemon grass - cintronellal, citral
  • spearmint - carvone
  • eucalyptus - cineole
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13
Q

how are terpenoids extracted

A
  • primarily distallation
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14
Q

what doe the extraction method selection depend upon (3)

A
  • nature of plant material
  • location of oil producing cells
  • stability of oil being extracted
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15
Q

what are the methods of extraction of terpenoids (6)

A
  1. hydrodistillation
  2. expression
  3. enfleurage
  4. solvent extraction
  5. destructive distillation
  6. liquid CO2
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16
Q

what are the 3 methods of distillation in hydrodistillation and what are each best suited for

A
  • water distillation
    • non-heat labile; dried plants
  • water & steam distillation
    • heat labile, fresh or dried plants
  • steam distillation
    • fresh plants
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17
Q

describe the water distillation process, what is it used for

A
  • extraction of terpentine from wood sources
  • non-heat labile i.e. those not damaged by boiling
  • dried plant materials
  • e.g. terpentine
  • Process
    • dried plants placed in distillation chamber
    • heated to boiling
    • volatile oil and water condenses in condensing chamber
    • separate oil/water fractions
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18
Q

describe the water/steam distillation process and what it is used for

A

used for

  • fresh or dry materials
  • can be used with heat labile oils
  • e.g. clove oil

process

  • finely ground plant materials added to chamber
  • covered with water
  • steam piped in
  • volatile oil carried by steam to condensing chamber
  • separate water/oil layers
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19
Q

describe the steam distillation process and what it is used for

A

Uses

  • fresh plants
  • e.g. spearmint peppermint

Process

  • macerate plants place on perforated trays or wire baskets
  • steam forced through plant
  • oils carried up in steam into receiving chamber
  • separate oil/water layer
20
Q

the expression process is useful for this type of oils, why

A
  • heat labile e.g. citrus oils
  • no heat applied, oil glands in fruit peel
21
Q

describe the expression process

A
  • oil glands in fruit peel pierced by projections then rolled through a mill which extracts oils
  • water spray removes oil from peels
  • oil separated from water by centrifugation
22
Q

enfleurage is commonly used in this industry

describe the process

A
  • perfume
  • removal of oils from petals

process

  • oil from flower petals extracted into cold fat or fixed oils
  • petals placed on glass plates covered with cold fat or fixed oils
  • after period of time petals replaced
  • once fat/oil has absorbed as much oil as possible it is extracted with alcohol
  • the alcohol extract is used in perfume
  • the oil is concentrated form by evaporation of alcohol
23
Q

what is a modified enfleurage method of extraction, describe the process

A
  • pneumatic method
  • warm air is passed through the petals, oil picked up into air
  • oil laden air sprayed with spray of melted fat
  • oil separated from fat via alcohol extraction

alternate

heat flowers in hot fat to extract oil, filter then cool

24
Q

solvent extraction method involves the use of_________and what is an advantage

A
  • low boiling point solvents (benzene) to extract the oil
  • more natural oil scent due to lower temperature than distillation
25
Q

destructive distillation is used for the extraction of these oils

describe the process

A
  • pine oils , wood resin e.g. pine tar

Process

  • heat plant in absence of water
  • plant decomposes and liberated volatile oil
  • condensed volatile oil collected in chamber where separated into 2 layers
  • remaining plant material carbonized
26
Q

the CO2 method of extraction is used for _____ and offers these advantages

A
  • low molecular weight species of terpenoid oils
  • good recovery, as no heat, can be used with all types of oils
27
Q

describe the CO2 extraction process

A
  • liquify gas under pressue
  • introduced into vessel containing plant material
  • CO2 carries volatile oil into reservoir
  • CO2 is vaporized, oil left behind
28
Q

what are the most important clinical applications of monoterpenes (4) and sesquiterpenes (3)

A
  • monoterpenes
    • anthelmintic
    • disinfectant
    • irritant
    • sedative
  • sesquiterpenes
    • analeptic agent
    • antibiotic
    • anthelmintic
29
Q

monoterpenoids such as ___6_____are still used in disinfectants and antiseptic agents.

A
  1. thymol
  2. menthol
  3. geraniol
  4. citronellal
  5. citral
  6. carvone
30
Q

which two terpenoids are used as antiseptics in oral preparations e.g. mouthwash & toothpaste

A
  • thymol
  • carvacol
31
Q

name a use of terpenoids in anthelmintic and or as an insecticidal

A

e.g. citronella

32
Q

how do terpenoids work as irritants, provide example

A
  • camphor used as irritant
  • rubefacient, irritates skin turns red, but the produces localized anesthetic effect
33
Q

terpenoids can act on the CNS and cause the following effects (3)

A
  • central stimulating
  • central sedating
  • central narcotic
34
Q

what is a terpenoid that has:

a central stimulating effect

a central sedative effect

A
  • a central stimulating effect
    • camphor
  • a central sedative effect
    • valerian
35
Q

what is a carminative

A

relieves gas

e.g. ginger, peppermint

36
Q

feverfew is a sesquiterpene lactone used for

A

migraines and arthritis

37
Q

rowachol is a monoterpene used in relief of

A

gall stones

38
Q

peppermint has been used in treatment of

A

IBS

39
Q

why is the quality control of terpenoids difficult (3)

A
  • because the molecules are complex in nature
  • seasonal variation in oil production
  • batch to batch consistency is difficult
40
Q

what are 3 ways in which standardization of terpenoids can be achieved

A
  1. physicochemical methods
  2. chromatographic analysis
  3. spectroscopic analysis
41
Q

physicochemical methods for anlysis of terpenoids include (7)

A
  1. freezing point
  2. optical rotation
  3. refractive index
  4. solubility in alcohol
  5. total alcohol ocncentration
  6. total esters
  7. nonvolatile residue
42
Q

which terpenoid is not assessed for optical rotation

A

turpentine

43
Q

why are physicochemical methods alone not suitable for standardization of terpenoids

A

adulteration methods have become sophisticated therefore orthoganal approach is best

44
Q

chromatographic methods used in the standardization of terpenoids include (3), when is each used

A
  • TLC
    • during characterization
  • GC
    • during characterization with TLC, then routinely GC
    • good for qualitative and quantitative
    • get fingerprint
  • HPLC
    • for complex oils where overlapping peaks present
    • after GC using fractions
45
Q

spectroscopic methods for standardization of terpenoids include

A
  • mass spec coupled with GC or HPLC

Pharmacognosy & Pharmaceutical Biology (14 decks)

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