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Terpenoids Flashcards

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
destructive distillation is used for the extraction of these oils describe the process
* 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
the CO2 method of extraction is used for _____ and offers these advantages
* low molecular weight species of terpenoid oils * good recovery, as no heat, can be used with all types of oils
27
describe the CO2 extraction process
* liquify gas under pressue * introduced into vessel containing plant material * CO2 carries volatile oil into reservoir * CO2 is vaporized, oil left behind
28
what are the most important clinical applications of monoterpenes (4) and sesquiterpenes (3)
* monoterpenes * anthelmintic * disinfectant * irritant * sedative * sesquiterpenes * analeptic agent * antibiotic * anthelmintic
29
monoterpenoids such as \_\_\_6\_\_\_\_\_are still used in disinfectants and antiseptic agents.
1. thymol 2. menthol 3. geraniol 4. citronellal 5. citral 6. carvone
30
which two terpenoids are used as antiseptics in oral preparations e.g. mouthwash & toothpaste
* thymol * carvacol
31
name a use of terpenoids in anthelmintic and or as an insecticidal
e.g. citronella
32
how do terpenoids work as irritants, provide example
* camphor used as irritant * rubefacient, irritates skin turns red, but the produces localized anesthetic effect
33
terpenoids can act on the CNS and cause the following effects (3)
* central stimulating * central sedating * central narcotic
34
what is a terpenoid that has: a central stimulating effect a central sedative effect
* a central stimulating effect * camphor * a central sedative effect * valerian
35
what is a carminative
relieves gas e.g. ginger, peppermint
36
feverfew is a sesquiterpene lactone used for
migraines and arthritis
37
rowachol is a monoterpene used in relief of
gall stones
38
peppermint has been used in treatment of
IBS
39
why is the quality control of terpenoids difficult (3)
* because the molecules are complex in nature * seasonal variation in oil production * batch to batch consistency is difficult
40
what are 3 ways in which standardization of terpenoids can be achieved
1. physicochemical methods 2. chromatographic analysis 3. spectroscopic analysis
41
physicochemical methods for anlysis of terpenoids include (7)
1. freezing point 2. optical rotation 3. refractive index 4. solubility in alcohol 5. total alcohol ocncentration 6. total esters 7. nonvolatile residue
42
which terpenoid is not assessed for optical rotation
turpentine
43
why are physicochemical methods alone not suitable for standardization of terpenoids
adulteration methods have become sophisticated therefore orthoganal approach is best
44
chromatographic methods used in the standardization of terpenoids include (3), when is each used
* 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
spectroscopic methods for standardization of terpenoids include
* mass spec coupled with GC or HPLC

Pharmacognosy & Pharmaceutical Biology (14 decks)

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