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Chem 185 Natural Products Chemistry > TERPENOIDS > Flashcards

TERPENOIDS Flashcards

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1
Q

mostly _____________extraction is employed to extract phenolic compounds

A

water

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2
Q

terpenoids are produced in what pathways?

A

mevalonic acid pathway
methyl erythritol phosphate pathway

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3
Q

_____________are the largest class of secondary metabolites.

A

Terpenoids or terpenes

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4
Q

The word “terpene” comes from ___________, the yellow to brown thick oleoresin which is obtained as an exudate from the terebinth tree (Pistacia terebinthus)

A

turpentine

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5
Q

Terpenes are historically, culturally and economically important:

A

✓ oleoresins
✓ distillates
✓ essential oils and perfumes
✓ drugs and steroids

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6
Q

terpenes vs terpenoids

A

terpenes pertains to the hydrocarbon part
terpenoid contains oxygen

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7
Q

terpenoids are mostly insoluble in water. true or false

A

true

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8
Q

____________formulated by Leopold Ruzicka.

A

Isoprene rule

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9
Q

_________represents the basic skeletal structure of the C5 unit

A

Isoprene

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10
Q

The most prolific producer of isoprene-type polymers is the ____________

A

rubber tree, Hevea brasiliensis.

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11
Q

the name of the reaction in producing limonene or condensing 2 isoprene units

A

diels-alder reaction

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12
Q

Class of terpenoids
C5
C10
C15
C20
C25
C30
C40

A

hemiterpenes
monoterpenes
sesquiterpenes
diterpenes
sesterterpenes
triterpenes
tetraterpenes

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13
Q

___________ is the C5 precursor of all terpenoids
also known as pyrophosphate

A

Isopentenyl diphosphate (IPP)

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14
Q

The ___________ operates in the cytoplasm and is responsible for the smaller terpenes and the phytosterols (sesquiterpenes and polyterpenes)

A

mevalonic acid (MVA) pathway

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15
Q

The _________________ operates in plastids and is responsible for the chloroplast terpenes (monoterpenoids, diterpenoids, and tetraterpenoids)

A

methyl erythritol phosphate
(MEP) pathway

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16
Q

the pathway that occurs in animals and higher plants

A

MVA pathway

17
Q

pathway first found in bacteria and green algae

A

MEP Pathway

18
Q

the pathway occurs in plants

A

MVA - usually
MEP- small

19
Q

the pathway that occurs in animals

A

only MVA

20
Q

pathways in organisms
Bacteria
Archaea
Green Algae
Fungi
Plants
Animals

A

MVA or MEP
MVA
MEP
MVA
MVA and MEP
MVA

21
Q

3R-Mevalonic acid
(MVA) is biosynthesized
from ___________

A

three acetates

22
Q

MVA is converted to
______________________
which is converted to
its isomer, ______________

A

isopentenyl diphosphate(IPP)
dimethylallyl diphosphate (DMAPP)

23
Q

__________. Acetyl-CoA (citric acid cycle) undergoes condensation with another acetyl-CoA molecule to form acetoacetyl-CoA via ______________

A

claisen condensation
acetoacetyl-CoA thiolase

24
Q

________________. Acetoacetyl-CoA condenses with another acetyl-CoA molecule to form 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) via ______________

A

aldol condensation
HMG-CoA synthase

25
Q

_______________. HMG-CoA is reduced to mevalonate by NADPH. This is the rate limiting step in cholesterol synthesis, which is why this enzyme is a good target for pharmaceuticals (statins) via __________________

A

Reduction
HMG-CoA reductase

26
Q

mevalonate undergoes ___________ and ____________ to form isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP)

A

phosphorylation
decarboxylation

27
Q

eukaryotes - phosphorylates at 5th carbon
archaea - phosphorylates at 3rd carbon. true or false

A

true

28
Q

Just a note!
Glyceraldehyde-3-phosphate
(GAP) and phosphoenolpyruvate
(PEP) are formed from glucose GAP condenses
with PEP to form
MEP. MEP is
converted to IPP
which forms its
isomer DMAPP.

A
28
Q

difference between MVA and MEP

A

in MEP - production of both DMAPP and IPP simultaneously
MVA - IPP needs to be isomerize to produce DMAPP

28
Q

Just a note!
the terpene family is formed by condensation of C5 (IPP) units

C10, monoterpenes (geranyl pyrophosphate)
C15, sesquiterpenes (farnesyl pyrophosphate)
C20, diterpenes (geranyl geranyl pyrophosphate)

C30 terpenes (squalene) are formed
by head-to-head
dimerization of C15
sesquiterpenes.

C40 terpenes (carotenes) are formed
by head-to-head
dimerization of C20
sesquiterpenes.

This leads to the
triterpenes, steroids, and
carotenes.

A
28
Q

_______________ are characteristic plant natural products, in particular, in the flowers.
These are important materials for perfumes
and food flavors.
They are classified structurally into the following: acyclic, monocyclic, bicyclic and tricyclic.

A

Monoterpenes

28
Q

is the starting point for the
monoterpenes.

A

Geranyl diphosphate (C10H17-OPP)

29
Q

the reaction called in the formation of cyclic monoterpenes

A

diels alder

30
Q

type of monoterpenoids in the general form of cyclopentanopyran

rearranged monoterpenes which have a characteristic fused 5/6
membered ring structure, typically found in plants as glycosides, most often bound to glucose

A

Iridoids

31
Q

(sesqui = “one and a half”) are derived from C15
farnesyl diphosphate (FPP).
serve as plant defense compounds, sensory
attractants or fragrance odors. The structures displayed by these
compounds attest to the rich chemistry that is found in plants.

A

Sesquiterpenes

32
Q

___________functionality is characteristic of sesquiterpenes and is found most widely in the Compositae family.
derived by oxidation and cyclization of the isopropyl side chain of the cyclized sesquiterpene

A

a-methylene-y-lactone

33
Q

Addition of another isopentenyl diphosphate (C5) group to farnesyl diphosphate (C15) forms geranylgeranyldiphosphate (GGPP,C20).

A

Diterpenes, C20

33
Q

General properties of terpenoids

A

lighter than water, boil 410K - 460 K
few are solids, usually volatile in steam
high refractive index
insoluble in water
optically active

33
Q

chemical properties of terpenoids

A

-unsaturated compounds
-undergo polymerization, dehydrogenation, addition reactions
-easily oxidized and thermally decomposed
-labile, readily isomerized

Chem 185 Natural Products Chemistry (16 decks)

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