TERPENOIDS

Question 1

mostly _____________extraction is employed to extract phenolic compounds

Answer 1

water

Question 2

terpenoids are produced in what pathways?

Answer 2

mevalonic acid pathway
methyl erythritol phosphate pathway

Question 3

_____________are the largest class of secondary metabolites.

Answer 3

Terpenoids or terpenes

Question 4

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

Answer 4

turpentine

Question 5

Terpenes are historically, culturally and economically important:

Answer 5

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

Question 6

terpenes vs terpenoids

Answer 6

terpenes pertains to the hydrocarbon part
terpenoid contains oxygen

Question 7

terpenoids are mostly insoluble in water. true or false

Answer 7

true

Question 8

____________formulated by Leopold Ruzicka.

Answer 8

Isoprene rule

Question 9

_________represents the basic skeletal structure of the C5 unit

Answer 9

Isoprene

Question 10

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

Answer 10

rubber tree, Hevea brasiliensis.

Question 11

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

Answer 11

diels-alder reaction

Question 12

Class of terpenoids
C5
C10
C15
C20
C25
C30
C40

Answer 12

hemiterpenes
monoterpenes
sesquiterpenes
diterpenes
sesterterpenes
triterpenes
tetraterpenes

Question 13

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

Answer 13

Isopentenyl diphosphate (IPP)

Question 14

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

Answer 14

mevalonic acid (MVA) pathway

Question 15

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

Answer 15

methyl erythritol phosphate
(MEP) pathway

Question 16

the pathway that occurs in animals and higher plants

Answer 16

MVA pathway

Question 17

pathway first found in bacteria and green algae

Answer 17

MEP Pathway

Question 18

the pathway occurs in plants

Answer 18

MVA - usually
MEP- small

Question 19

the pathway that occurs in animals

Answer 19

only MVA

Question 20

pathways in organisms
Bacteria
Archaea
Green Algae
Fungi
Plants
Animals

Answer 20

MVA or MEP
MVA
MEP
MVA
MVA and MEP
MVA

Question 21

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

Answer 21

three acetates

Question 22

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

Answer 22

isopentenyl diphosphate(IPP)
dimethylallyl diphosphate (DMAPP)

Question 23

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

Answer 23

claisen condensation
acetoacetyl-CoA thiolase

Question 24

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

Answer 24

aldol condensation
HMG-CoA synthase

Question 25

_______________. 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 __________________

Answer 25

Reduction HMG-CoA reductase

Question 26

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

Answer 26

phosphorylation decarboxylation

Question 27

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

Answer 27

true

Question 28

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.

Question 28

difference between MVA and MEP

Answer 28

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

Question 28

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.

Question 28

_______________ 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.

Answer 28

Monoterpenes

Question 28

is the starting point for the monoterpenes.

Answer 28

Geranyl diphosphate (C10H17-OPP)

Question 29

the reaction called in the formation of cyclic monoterpenes

Answer 29

diels alder

Question 30

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

Answer 30

Iridoids

Question 31

(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.

Answer 31

Sesquiterpenes

Question 32

___________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

Answer 32

a-methylene-y-lactone

Question 33

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

Answer 33

Diterpenes, C20

Question 33

General properties of terpenoids

Answer 33

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

Question 33

chemical properties of terpenoids

Answer 33

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