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NatProd > Terpenes And Steroids > Flashcards

Terpenes And Steroids Flashcards

1
Q

6 classification of terpenes according to C5 units

A

Monoterpenes, sesquiterpenes, diterpenes, triterpenes, tetraterpenes and sesterterpenes

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2
Q

Mavalonic Acid is from?

A

Acethyl-CoA

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3
Q

Terebinth tree genus name

A

Pistacia Terebinthus

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4
Q

Contain an
integral number
of five carbon
units called
isoprene

A

Terpenoids and Isoprenoids

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5
Q

IUPAC name of isoprene

A

2-methylbuta-1,3-diene

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6
Q

Isoprene Rule

A

Condensation of successive isoprene
units in a head-to-tail fashion would
produce compounds of formula (C5)n.

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7
Q

Biogenetic Isoprene Rule

A

Terpenoids are assembled from C5 units
(isoprene-like) but the initially formed
structure could be modified enzymatically
in a number of ways to generate the known
skeletal types.

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8
Q

Hemiterpenes with common and natural occurance

A

Isovaleraldehyde and Isovaleric acid

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9
Q

Hemiterpenes that are non-isoprenoid

A

Tiglic acid and isoleucine

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10
Q

Basis of many finished goods

A

Monoterpenes and Sesquiterpenes

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11
Q

Flavoring of processed meat and tinned goods, confectionery, perfumes for cosmetics, soaps and detergents.

A

Monoterpenes and Sesquiterpenes

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12
Q

Terpenoids with C10 units

A

Menthol and camphor

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13
Q

Terpenoids with C20 units

A

Vitamin A

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14
Q

Terpenoids with C30 units

A

Squalene, Vitamin D and Cholesterol

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15
Q

Monoterpene metabolites with six-membered ring containing an oxygen
atom fused to a cyclopentane ring

A

Iridoids

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16
Q

Example of iridoids and their structures

A

Iridomyrmecin, Iridodial, Loganin and Nepetalactone

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17
Q

Function of Iridoids

A

Chemical defense (as irritant) and communication (excitatory effects)

18
Q

Examples of Secoiridoids

A

(SGS)
Secologanin, Gentiopicroside and Sweroside

19
Q

Major constituent of hops and is responsible for the bitter taste of beer

A

Humulone

20
Q

Humulone comes from what?

A

DMAPP

21
Q

Contain furan rings
or tetrahydrofuranyl
moieties

A

Acyclic Sesquiterpenes

22
Q

Examples of Acyclic Sesquiterpenes

A

Freelingyn and davanone

23
Q

Examples of Cyclic Sesquiterpenes with their structures

A

Humulone and γ-Bisabolene

24
Q

Marked biological activity (antitumor) and are Michael acceptors (potent alkylating agents)

A

Sesquiterpene Lactones

25
Q

3 Halogenated sesquiterpenes

A

Novel, Marine organisms are a rich source and Laurencia Pacifica (red algo)

26
Q

Unifying factor is diverse Sesquiterpenes as progenitor

A

Farnesyl
pyrophosphate

27
Q

Oil of lavender

A

Linalol

28
Q

Attar of roses

A

Geraniol

29
Q

Three kinds of communication mediated by
terpenes:

A

Trail laying, sexual attraction, deterrence

30
Q

Attract preys, elicit help in pollination, repel
insects and other herbivores

A

Natural fragrances and flavors

31
Q

An acyclic diterpene
incorporated in
chlorophyll molecule

A

Phytol

32
Q

Fungal origin
and largest group of
sesterterpenes

A

Ophiobolin

33
Q

Terpene class that are relatively small number

A

Sesterterpenes

34
Q

Sesterterpenes that are from from insect
waxes.

A

Gascardic acid

35
Q

Sesterterpenes from sponges of the
genus Ircinia

A

Variabilin

36
Q

Number of carbon skeleton in steriods

A

C27-C29

37
Q

Number of carbon skeleton in triterpenes

A

C-30

38
Q

Common precursor of steroids and triterpenes

A

Squalene

39
Q

Difficult to break down into C5 units
because of extensive rearrangement.

A

Steroids and triterpenes

40
Q

FINDING THE PRECURSORS

A
  1. Locate the geminal dimethyl moiety
    (isopropyl group)
  2. Count 5 carbons
  3. Cut
  4. Continue until all carbons are
    accounted for
41
Q

Found in many
monocyclic
monoterpenoids

A

P-menthane

NatProd (2 decks)

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