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Ph Ch 128 3rd Exam > Mevalonate 1 > Flashcards

Mevalonate 1 Flashcards

1
Q

Modified terpenes where oxygen is added and methyl groups were moved or removed

A

Terpenoids

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2
Q

Units arising from acetate via mevalonic acid;

Branched chain 5-C units with 2 unsat. bonds

A

Isoprene

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3
Q

Other name for isoprene

A

2-methyl-1,3-butadiene

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4
Q

Class with 1 isoprene unit

A

Hemiterpene

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5
Q

Class with 2 isoprene units

A

Monoterpenes

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6
Q

Class with 3 isoprene units

A

Sesquiterpenes

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7
Q

Class with 4 isoprene units

A

Diterpenes

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8
Q

Class with 5 isoprene units

A

Sesterterpenes

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9
Q

Class with 6 isoprene units

A

Triterpenes

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10
Q

Class with 8 isoprene units

A

Tetraterpenes

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11
Q

Decomposition products from various natural cyclic hydrocarbons

A

Isoprene

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12
Q

2 biochemically active isoprene units

A 
Dimethylallyl diphosphate (DMAP)
Isopentenyl diphosphate (IPP)
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13
Q

Pathways in isoprene biosynthesis

A

Mevalonate

Methylerythritol phosphate

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14
Q

Hemiterpene intermediates for more complex terpenoids

A

DMAPP

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15
Q

Alkylating agent for meroterpenoids formation

A

DMAPP

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16
Q

Used as flavouring agents in pharmaceutical, confectionery, and perfume products

A

Monoterpenes

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17
Q

Used in liniments against rheumatic pain

A

Camphor

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18
Q

Used in ointments and liniments as a remedy against itching

A

Menthol

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19
Q

Used as an aromatic bitter tonic and as a remedy for poor apetite

A

Bitter-orange peel

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20
Q

Used in bactericidal preparations

A

Thymol and carvacrol

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21
Q

Isomers of geranyl PP

A

Linalyl PP

Neryl PP

22
Q

It undergoes ionization that permits change of attachment of diphosphate group and change in the stereochemistry

A

Geranyl PP

23
Q

Monoterpenes in structural form

A

Acyclic
Monocyclic
Bicyclic

24
Q

Monoterpenes classified by their functional groups

A 
Simple hydrocarbons
Alcohols
Ketones
Aldehydes
Acids
Phenols
25
Q

Used for cyclic monoterpene biosynthesis

A

Linallyl PP and neryl PP

26
Q

3 acyclic monoterpenes

A

Hydrocarbons
Aldehydes
Alcohols

27
Q

Hydrocarbons (acyclic monoterpene)

A

ß- myrcene

(+)-alpha-phellandrene

28
Q

Derived from linallyl PP or neryl PP

A

Monocyclic monoterpenes

29
Q

Fates of menthyl/a-terpinyl cation monocyclic monoterpene

A

Quenching with nucleophiles, water
Loss of a proton
Cyclization
Wagner-Meerwein (1,3-hydride shift) rearrangement

30
Q

Fates of menthyl/a-terpinyl cation bicyclic monoterpenes

A

Folding the cationic side-chain of menthyl cation towards the double bond w/ an aid of an enzyme
Loss of proton and formation of cyclopropane ring
Wagner-Meerwein rearrangement (1,2-hydride shift)

31
Q

Types of bicyclic monoterpenes

A 
Pinane
Camphane/bornane
Fenchane
Isocamphane
Carane
Thujane
32
Q

Terpenoids derived fom C5 units that do not link in a regular head-to-tail coupling mechanism

A

Irregular monoterpenes

33
Q

Family where irregular monoterpenes are limited to

A

Asteraceae

34
Q

2 irregular monoterpenes

A

Chrysanthemic acid

Pyrethric acid

35
Q

Irregular monoterpene derived from DMAPP and IPP

A

Pyrethric acid

36
Q

Cyclopropane structures from 2 isoprene units

A

Chrysanthemic acid

37
Q

Found in nature as an ester such as pyrethrins, cinerins, and jasmolins

A

Pyrethric acid

38
Q

Pyrethric acid is the insecticidal component of pyrethrum flowers, the flower heads of _______ _______ (Fam. _____)

A

Chrysanthemum cinerariaefolium (Fam. Asteraceae)

39
Q

Monoterpenoids with iridane skeleton which contains a cyclopentane ring fused to a six-membered oxygen heterocycle

A

Iridoids

40
Q

Powerful attractant and stimulants for cats

A

Nepetalactone

41
Q

Source of nepetalactone

A

Catmint, Nepeta cataria (Fam. Lamiaceae)

42
Q

Key intermediate in the biosynthesis of other iridoid structures, terpenoid indole alkaloids, and tetrahydroisoquinoline alkaloids

A

Loganin

43
Q

Representative of secoiridoids

A

Secologanin

44
Q

A secoiridoid contributing to the bitter taste of the Gentian root herbal drug

A

Gentiopicroside

45
Q

Source of gentiopicroside

A

Gentian root, Gentiana lutea (Fam. Gentianaceae)

46
Q

Epoxyiridoid ester with sedative activity of the crude drug

A

Valtrate

47
Q

Source of valtrate

A

Valeriana officinalis (Fam. Valerianaceae)

48
Q

General term for natural products whose structures may be divided into isoprene units

A

Terpenes

49
Q

Aldehydes (acyclic monoterpenes)

A

Geranial (Z-citral)
Citronellal
Neral (E-citral)

50
Q

Alcohols (acyclic monoterpenes)

A

Citronellol
Geraniol
Linalool
Nerol

Ph Ch 128 3rd Exam (4 decks)

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