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(SLU) PHARMA 112L > ACT 6: TERPENOIDS, RESINS, TANNINS > Flashcards

ACT 6: TERPENOIDS, RESINS, TANNINS Flashcards

1
Q
  • hydrocarbons of plant origin and refer to the oxygenated, hydrogenated, and dehydrogenated derivatives of hydrocarbons
  • originates from the mixture of ___________ in ___________
  • only limited to a class of terpenoid compounds called ________
  • also the building blocks of ___________, joined together in a head-to-tail fashion.
A
  • isomeric hydrocarbons (C10H16) in turpentine oil
  • monoterpene hydrocarbon (C5H8)2
  • isoprene units

TERPENOIDS

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2
Q

PHYSICAL CHARACTERISTICS

  • generally colorless compounds and are lighter than water
  • boiling point is between the range of 150-180 °C.
  • optically active liquids (few terpenoids are solid) and are insoluble in water but soluble in organic solvents.
  • The pleasant-smelling parts of the plants like flowers, leaves, stems, bark, wood, and fruits are due to some volatile oils known as ______________
A
  • essential oils

TERPENOIDS

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3
Q

PHYSICAL CHARACTERISTICS

  • chief constituents of essential oils are terpenoids having atoms up to _____.
  • located in the __________ of plant cells.
  • Essential oils are sometimes present in _______________ on the leaf surface, whereas carotenoids are mainly associated with __________in leaves and __________ in petals.

_____ & ___________ are primarily found in gums and resins. Some triterpenoids are also present in the animal kingdom.

A
  • C15
  • cytoplasm
  • special glandular cells
  • chloroplast; chromoplast
  • Di- and triterpenoids
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4
Q

The ambergris contains a terpene called ________ and _________.

A

ambroxan and ambrinol

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5
Q
  • lipid-soluble pigments widely distributed in all plants, including bacteria.
  • Carotenoids are either unsaturated hydrocarbon form or their oxygenated derivatives known as _________.
  • Crocin obtained from ____________ is the only water-soluble carotenoid present in plants.

a. Hydrocarbons: _________ & __________
b. Xanthophylls: ________, ________, _________

A
  • xanthophylls
  • Crocus sativus

a. Carotenes and Lycopene
b. Zeaxanthin, Capsanthin, and Lutein

TETRATERPENOIDS (carotenoids)

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6
Q
  • odorous, volatile principles of plant and animal sources.
  • produce their characteristic odor when these oils evaporate when exposed to air, hence known as _________ or ________.
  • represent the essence of active constituents of the plant, hence also known as _________.
A

volatile or ethereal oils

essential oils

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7
Q
  • Chemically derived from terpenes (mainly ______ & ______) and their oxygenated derivatives
  • soluble in alcohol and other organic solvents, practically insoluble in water, and lighter than water (Clove oil is heavier).
  • possess characteristic odor and have a high refraction index
  • Most of them are optically active.
  • colorless liquids, but when exposed to air and direct sunlight, these become darker due to ________.
  • Unlike _______, volatile oils do not leave permanent grease spots on filter paper.
  • not saponified with alkalis.
A

(mainly mono and sesquiterpene)

oxidation

fixed oils

VOLATILE OIL

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8
Q

Volatile oils are secreted in special structures like duct cells, schizogenous or lysogenous glands, trichomes, and vittae.

Volatile oils are commonly found in families like:

  1. Lamiaceae: _________
  2. Apiaceae: ________, ________, ________, _________
  3. Lauraceae: _________
  4. Asteraceae: ________
  5. Zingiberaceae: ________, _______
  6. Myrtaceae: ________, ________
  7. Poaceae: ___________
A
  1. Peppermint
  2. Coriander, Fennel, Caraway, Cumin
  3. Cinnamon
  4. Marigold
  5. Cardamom, Ginger
  6. Clove, Eucalyptus
  7. Lemon grass
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9
Q
  • poorly defined chemically but are more related to each other in their physical properties and appearance.
  • amorphous mixtures of essential oils, oxygenated products of ______, and _________.
  • obtained as ________ from plants and considered the end product of _________.
A
  • terpenes, carboxylic acids
  • exudates
  • metabolism

RESINS

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10
Q
  • generally solid or semi-solid amorphous products of complex chemical nature and usually insoluble in water but soluble in an organic solvent like alcohol, volatile oils, fixed oils, benzene, and ether.
  • also complex mixtures of several compounds;
  • _________ units are the fundamental building blocks of all true resins.
  • These are non-crystallizable translucent masses that soften and melt on heating and burn with smoky flames on ignition.
  • denser than water and contain a large number of carbon atoms
A

isoprene (C5H8)

resin

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11
Q
  • occur in different secretory structures like resin cells (_____), Schizo or Schizolysogenous ducts or cavities (_______), and glandular hairs (_______).
  • sources include gymnosperms (present in the family Pinaceae (Pinus sp.) known as ________ and ________ mainly composed of hydrocarbons) and angiosperms which may include the following
    families:
  • Cucurbitaceae: ________
  • Fabaceae: ________
  • Dipterocarpaceae: ________
  • Burseraceae: ________
  • Apiaceae: ________
  • Zingiberaceae: ______ & ______
  • Cannabinaceae: ________
  • Convovulaceae: ________
  • used in mummification during the embalming process
A
  • Ginger; Pinus sp.; Cannabis
  • Colophony and Tar-

Colocynth
Tolu Balsam
Gurjan Balsam
Myrrh
Asafoetida
Ginger and Turmeric
Cannabis
Jalap

  • myrrh

RESINS

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12
Q

classifications of resins

A

ON THE BASIS OF THEIR…

  1. FORMATION
    a. physiological resins
    b. pathological resins
  2. CHEMICAL NATURE
    a. resin acids
    b. resin alcohols
    c. resin phenols (resinotannols)
    d. ester resins
    e. resenes
  3. OCCURENCE WITH OTHER SECONDARY METABOLITES
    a. oleoresins
    b. gum resin
    c. oleogum resins
    d. glycoresins
    e. balsams
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13
Q
  1. ON THE BASIS OF THEIR FORMATION
A

a. PHYSIOLOGICAL RESINS
b. PATHOLOGICAL RESINS

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14
Q
  • formed as a normal product of metabolism without making injury to the plants and mainly present in specialized cells like:

Schizogenous glands: _________

Secretion cells: _________

Oil glands: _________

Oil ducts: _________

A

Copaiba
Ginger
Clove
Apiaceae fruits

PHYSIOLOGICAL RESINS

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15
Q
  • formed due to a wound, injury, or abnormal circumstances on the plant and produce a number of resin ducts.
  • ______, ______, ______, ______
A
  • Benzoin, Colophony, Balsams, Aloe resin

PATHOLOGICAL RESINS

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16
Q
  1. ON THE BASIS OF CHEMICAL NATURE
A

a. RESIN ACIDS
b. RESIN ALCOHOLS
c. RESIN PHENOLS (RESINOTANNOLS)
d. ESTER RESINS
e. RESENES

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17
Q
  • HMW acids, AKA _______.
  • In combination with alkali, these form their metallic salts known as _________.
  • generally found in a free state or in combination with resin alcohols as esters (from Colophony, copaiba, frankincense)
A
  • resinolic acids
  • resonates

RESIN ACIDS

18
Q
  • HMW compounds, also known as ________, occur either in free form or as esters in combination with _______ acids or ______ acids.
  • These are tetra or pentacyclic alcohols and usually derivatives of ________ (from Storax).
A

resinols

  • balsamic acids or resin acids
  • amyrines

RESIN ALCOHOLS

19
Q
  • HMW compounds with a phenolic group, occur either in free form or as esters.
  • soluble in aqueous alkali solution due to the formation of __________
  • These are insoluble in water and soluble in alcohol and ether. These give color reactions with FeCl3

_______, _______, _______

A
  • phenoxide

Peru balsam, Tolu balsam, and Benzoin

RESIN PHENOLS (RESINOTANNOLS)

20
Q
  • esters of resin alcohol or resinotannols with resin acids or balsamic acids.
  • On treatment with alkali, these are mostly converted to _________

_______, ______, _______

A

free acids

Asafetida, Benzoin and Storax

ESTER RESINS

21
Q
  • complex neutral, chemically inert HMW hydrocarbons generally found in a free state
  • neither show any characteristic property nor effected by moisture and light
  • soluble in ______ and ______ but insoluble in water (_____, ______).
A

chloroform and benzene

mastic, myrrh

RESENES

22
Q
  1. ON THE BASIS OF OCCURENCE WITH OTHER SECONDARY METABOLITES
A

a. oleoresins
b. gum resin
c. oleogum resins
d. glycoresins
e. balsalms

23
Q
  • homogenous mixtures of resins and volatile oils
  • depending on the amount of volatile oil, these may exist as a liquid, solid or semisolid

(_____, _____, _____, _____, _____).

A

OLEORESINS

Copaiba, Canada balsam, Capsicum, Ginger, and Turpentine

24
Q
  • Naturally occurring mixtures of resin with gum

(______).

A

Gamboage

GUM RESINS

25
Q

Naturally occurring combinations of volatile oil, gum, and resin

(______, ______).

A

Myrrh, Asafetida

OLEOGUM RESINS

26
Q
  • Resins in combination with sugars as glycosides.
  • These can be hydrolyzed with acids to get glycone and aglycone parts.

(_______, _______)

A

Jalap and Podophyllum

GLYCORESINS

27
Q
  • Naturally occurring resinous mixtures containing cinnamic acid, benzoic acids, and/or their esters

(______, ______, ______, _____).

A

Benzoin, Balsam of tolu, Balasam of Peru, Storax

BALSAMS

28
Q

PHARMACEUTICAL APPLICATION OF RESINS:

  • local irritants and hence act as local cathartics (_____)
  • anti-cancer (_____),
  • bronchial asthma (_____)
  • also used externally as a mild antiseptic in the form of tinctures (_____) ointment and plasters (_________ & ________).

Resins are also used in the preparation of emulsion and sustained release formulations.

A
  1. Jalap
  2. Podophyllum
  3. Cannabis
  4. Benzoin; Turpentine and Colophony
29
Q
  • mixture of complex organic, non-nitrogenous substances derivatives of polyhydroxy benzoic acid (________) with the ability to precipitate proteins (________)
  • high molecular weight (500 to> 20000) and are non-crystallizable
  • soluble in water (forming ___________), dilute alkali, alcohol, glycerol, and acetone while sparingly soluble in ethyl acetate, chloroform, and other organic solvents
  • Aqueous solutions of tannins are _______ due to the presence of free _______ and _______. They precipitate heavy metals, alkaloids, glycosides, and gelatin (proteins) from solutions.
A
  • polyphenols
  • astringent
  • colloidal solution
  • acid
  • phenolic and carboxylic groups

TANNINS

30
Q
  • this combined with proteins by cross-links making raw animal skin to leather and on application to the living surface it renders proteins resistant to proteolytic enzymes (astringent property), which forms the basis of therapeutic application of tannins;
  • which is due to the formation of hydrophobic bonds between collagen fibers that imparts resistance to water, heat, and abrasion.
A
31
Q
  • widely distributed in the plant kingdom
  • localized in specific plant parts such as leaves, fruits, barks, or stems
  • often found in immature fruits and disappear during ripening.
  • mainly present in ______ and ________ in higher plants in solution form.
  • The hydrolyzable tannins are characteristic of _____ plants, while condensed tannins are found in all plants, including _________ and _________
A
  • cell saps and vacuoles
  • dicot
  • pteridophytes and Gymnosperms

TANNINS

32
Q

2 categories of tannins

types of tannins

A

ON THE BASIS OF

  1. chemical nature
  2. biogenetic origin

+++++++++

  1. hydrolysable tannins
    a. gallotannins
    b. ellagitannins
  2. condensed tannins
  3. complex tannins
  4. pseudo tannins
33
Q
  • esters of sugars and phenolic acid molecules (______ & ______), hydrolyzed by mineral acids, alkalis, and tannase enzymes, yielding gallic acid or __________________ with sugar (mainly glucose).
  • this on dry distillation yield _______, and reaction with FeCl3 produce a ________ precipitate.
  • These are further subdivided into ________ & ________ based on their product of hydrolysis.
A
  • gallic acid and ellagic acid
  • hexahydroxydiphenic acid
  • pyrogallol
  • bluish-black

gallotannins and ellagitannins

HYDROLYSABLE TANNINS

34
Q
  • simplest ones, also known as ___________
  • _______, _______, _______, ______
A
  • galloylglucose
  • Nutgall, Rhubarb, Clove, and Chest nut

GALLOTANNINS

35
Q

composed of phenolic acids as a dimer of gallic acid and attached to a glucose molecule (_____).

A
  • oak

ELLAGITANNINS

36
Q
  • also called flavolans, proanthocyanidins, nonhydrolyzable tannins, catechol tannins, and phlobatannins.
  • resistant to hydrolysis and do not contain sugar molecule
  • On treatment with acids or enzymes, these are converted to a red water-insoluble compound called ________, which imparts typical brownish color to many plant materials, mainly bark.
  • On treatment with ferric chloride give brownish green color, with dilute HCI yields ________ that gives a red color with matchstick on reaction with lignin, with vanillin HCI gives red color and precipitated with bromine water (Green tea, Cinnamon bark, Cinchona bark, Wild cherry bark, Oak, Coca, Catechu).
A
  • phlobaphene
  • phloroglucinol

CONDENSED TANNINS

37
Q

formed by the combination of hydrolyzable and condensed tannins

A

COMPLEX TANNINS

38
Q
  • also known as ________ or _____________
  • high molecular weight compounds do not respond to protein precipitation tests (Gallic acid).
A
  • prototannins or tannin precursors

PSEUDO TANNINS

39
Q

PHARMACEUTICAL APPLICATION OF TANNINS:

  • astringent property
  • used in GIT problems, burns, the leather industry, and for the formation of inks.
  • precipitates proteins and is traditionally used as a ___________ and internally for the protection of the surface of the mouth and throat
  • also act as anti-diarrheal agents and antidotes in the poisoning caused by heavy metals, alkaloids, and glycosides
  • reduced nowadays because tannic acid causes necrosis of the liver.
  • Recently it has been demonstrated that tannins are useful as an anticancer and anti-HIV agent.
A
  • styptic agent
40
Q

refers to extracting, screening, and identifying medicinally active substances found in plants

A

phytochemical screening

  1. Identification and Collection of plant material
  2. Washing and garbling
  3. Drying
  4. Grinding
  5. Extraction of Phytochemicals
  6. Analysis of phytochemicals

(SLU) PHARMA 112L (17 decks)

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