1
Q
how many isoprenes in diterpenoids, sesterterpenoids, triterpenoids, and tetraterpenoids?
A
4
5
6
8
2
Q
gen role of cytochrome P450 & and?
A
in liver - detoxification
- can introduce toxins too
3
Q
what are diterpenoids made from
A
C20 skeleton from GGPP
- head-tail of IPP + FPP
sometimes GLPP
- FPP +DMAPP
4
Q
A
4
Q
what enz for FPP+IPP = GGPP?
A
farnesyl transferase, Mg2+ or Mn2+
5
Q
T/F diterpenoids are all cyclics
A
false, mostly cyclics with some acyclics
6
Q
types of diterpenoid cyclics (5)
A
- monocyclic
- bicyclic
- tricyclic
- polycyclic
- macrocyclic
7
Q
diterpenoid: ex of 1ry plant metabolism (2)
A
- gibberellin (GA) phytohormones
- phytol side chain of chlorophyll
8
Q
diterpenoid: ex of 2ry plant metabolism (1)
A
- phytoalexins have been shown to confer resistance against pests or pathogens
9
Q
“phytoalexins have been shown to confer resistance against pests or pathogens”
- is this antimicrobial and/or antioxidant?
A
both antimicrobial and antioxidant
10
Q
diterpenoid char (how many, volatility, ease of separation, structure)
A
- several thousands!!! (mod and cyclizing of GGPP)
- not as volatile as sesquiterpenoids (smaller)
- hard to separate and analyze
- 1-5 ring compounds
11
Q
are most diterpenoids oxygenated?
A
yes!
12
Q
diterpenoids: uses, ex
A
drugs, scents, flavours
- Taxol -> breast cancer!
13
Q
diterpenoids: phytol char
- cyclization
- anti-___
- attached to ___
- solubility
- fossil record
- precursor to _____
A
- acyclic
- anti-parasitic
- esterified to porphyrin ring of chlorophyll
- phytol confers lipid solubility to chlorophyll
- in fossils -> early presence of terpenoids + chlorophyll
- precursor to vit E and K!
14
Q
what kind of skeleton does phorbol have
A
tigliane skeleton!
15
Q
what is one of the most common terpenoids?
A
chlorophyll
16
Q
phorbol: uses?
A
- uses in cancer research
- phorbol ester (TPA/PMA) used in carcinogenesis
16
Q
most studied diterpenoid
A
gibberellins (GA)
16
Q
T/F kaurene and ent-kaurene are both found among diterpenoids and used to make GAs
A
false; they are both found, but only ent-kaurene is used to make gibberellins
17
Q
ent-kaurene and kaurene relationship
A
isomer
18
Q
GA biosynthesis (7 steps)
A
- MVA -> GGPP
- cyclization to ent-kaurene
- oxidation of ent-kaurene
- contraction of ring B -> GAs
- lose 1 C
- interconversion
- conjugation
19
Q
GA biosynthesis:
___ exuded from ring,
oxidized by ____
A
C-OH exuded from ring,
oxidized by DHase
20
Q
most common gibberellin =?
A
GA3
21
Q
GA3 modifications (from gibberellin) (3)
A
- double bond
- OH x2
- COOH needed for activity
22
gibberellin uses (in plant)
- promotes flowering
- stem growth
- breaking dormancy (seed)
- enz synthesis
- fruit develop
23
gibberellins commercial uses
- malting in barley (hydrolysis of starch to sugar); sustain fermentation
- increase sugar cane yield + stock growth (~10%)
24
how many C in sesterterpenoid
25
25
sesterterpenoid: types of cyclics/acyclic (6)
- linear
- mono-, bi-, tri-, tetra-, macrocyclic
26
T/F sesterterpenoids are not well researched
true; they are rare
27
sesterterpenoids are important in ______ interactions
host-microbe interactions
28
sesterterpenoids: Arabidopsis thaliana; lack of 2 sesterterpenoids had what effect?
major impact on root microbiota assembly
29
sesterterpenoid ex: leucosesterterpenone use
potential anti angiogenic agent
30
___ is precursor for sesterterpenes?
GFPP
31
where are GFPP made? w what?
formed by _____
- made in plastids (MEP)
- by GFPPS
- formed by plastid localized sesterterpene synthases (SrTS)
32
most if not all triterpenoids are derived from???
acyclic C30 squalene
33
triterpenoids char
- #C
- most are cyclic/acyclic
- what kind of cyclic
- colour?
- mp
- metabolic stability
- C30
- mostly cyclic
- most tetra/pentacyclic
- usu colourless
- high mp
- metabolically stable
34
hows squalene made (rxn)
FPP+FPP (head-head)
35
triterpenoids can be divided into (4)
- true triterpenoids
- steroids
- saponins
- cardiac glycosides
36
triterpenoids: tetra/pentacyclics are found in what subcategory?
true triterpenoids!
37
triterpenoids: where are pentacyclics found? are they common
- common
- waxy coating, bark, some resins
- petroleum
38
triterpenoids: pentacyclics
- beta-amyrin R group
- oleanic acid R group
- Me
- COOH
39
triterpenoids: pentacyclics
limonoids taste
bitter (in citus)
40
triterpenoids: pentacyclics
hopanes importance
marker of petroleum in waste! (refining and spills)
41
triterpenoids: tetracyclics
what is the cholesterol precursor in animals?
lanosterol
42
triterpenoids: tetracyclics
what is the sterol precursor in plants
cycloartenol
43
do insects make steroids?
no! from diet + modification
44
difference b/w lanosterol and cycloartenol
cyclopropane (C9) in lanosterol instead of double bond in cycloartenol
45
diff b/w cholesterol and lanosterol/cycloartenol? (2)
C's removed, O's added
46
downstream cholesterol molecule uses:
- aldosterone
- cortisone
- ecdysones
- aldosterone - H2O balance
- cortisone - anti-inflam
- ecdysones - insect molting (insecticide in plants)
47
triterpenoids: saponin examples and found in (3)
- diosgenin (wild yams)
- hecogenin (agave)
- solanine (green parts of potato)
48
characteristics:
- diosgenin (wild yams)
- hecogenin (agave)
- solanine (green parts of potato)
diosgenin/hecogenin
- foaming like soap
- hemolyze BCs
- fish poison, antifungal, antibiotic
- usu in glycoside form
solanine
- sterol alkaloid and glycoside
- nausea/paralysis, maybe fatal
49
triterpenoids: cardiac glycosides
- made from
- usu ___
- active when ____
- function?
- found in?
- from pregnenolone + acetylCoA
- usu glycoside
- active when sugar removed
- inhibit Na/K pumps in cell membranes!!!!!!
- found in foxglove
50
bufadienolides
- toxicity
- toad poisons
- too toxic for treatment of heart disease (unlike cardenolides?)
- found in few plants
51
cardiac glycosides ex:
- ouabain
- oleandrin
- convallatoxin
found where? is it toxic?
ouabain
- potent cardiac glycoside
oleandrin
- found in oleander, deadly if eaten
convallatoxin
- most toxic cardiac glycoside!!!
- found in lily of valley; deadly!
52
precursor of carotenoids
lycopene
53
what makes carotenoids? & where!!
- chloroplasts of plants and algae
- chromoplasts (ex. tomatoes)
- also photosynthetic bacteria
54
what colours can carotenoids be? why?
- yellow, red, orange in leaves/fruits/flowers
- absorb at 400-500 nm to protect
55
are carotenoids lipid soluble?
yes
56
are carotenoids made in animals?
no, but flamingos, starfish, lobster, sea urchin eat and store them
57
carotenoids are sources of what vit?
vit A - retinol
58
carotenoid synthesis steps (name of 4 precursors) + addition of?
GGPP
..
..
phytofluene
carotene
lycopene
addition of double bonds
59
why do plants change amts of:
xanthophyll-zeaxanthin cycle?
light amount (low/high)
60
terpenoid diversity:
what do P450s generally catalyze?
insertion of oxygen (hydroxylation)
61
land plant P450 families have ___ clans?
11 clans/families
62
terpenes diversify even more by adding __, __, __, or even ___ groups
- acyl
- glycosyl
- benzoyl
- alkaloid
63
T/F allelochemicals are made by plants, animals, and microbes
True, but plants make the most
64
T/F allelochemicals are safer because they are natural
False, can be more toxic than pollutants
65
ex. cassava has __ (allelochemical) and needs to be soaked in H2O
cyanide
66
are allelochemicals found in leaf litter or only alive material?
yes, also found in leaf litter
67
what do phytoalexins do?
defense against fungi and bacteria
68
T/F we don't know a lot of allelochemicals
false; less than terpenoids but still a lot
69
T/F many allelochemicals are not purified and characterized
false
70
general method of allelochemical extraction
- extract with solvent
- partial purification
- test fractions on target
- purify fractions w activity
- test pure compounds
71
what is a potential issue with purifying allelochemicals for specific function?
they might need to work together for the effect
72
effects of allelochemicals (2 major, + minor)
- tonoplast leakage
- membrane dmg
- inhibit nutrient uptake, K uptake, inhibit plant hormones, inhibit protein synthesis, increase membrane permeability
73
juglone:
- effects, made by
- what also acts at same site as juglone
- made by black walnut trees
inhibit:
- e- transport
- PSII (binds to plastoquinone, competitive inhibition)
- CoQ (reduction in mitochondria)
- atrazine
74
how does juglone competitively inhibit photosynthesis (where does it bind)
- inhibit PSII by binding to plastoquinone site!!!
75
why are allelochemicals considered to be env friendly
- low toxicity
- very selective
- biodegradable
76
HABs = ?
- harmful algal blooms
77
how can HABs toxicity affect mussels and shellfish
- accumulate algal toxins
- direct shellfish poisoning (DSP)
78
algicide (4) types mnemonics
- trans femboy nudes please
- terpenoids (least effective)
- fatty acids/esters
- N-containing compounds
- polyphenolics (most effective)
79
most common allelochemical in HABs control?
polyphenolics
80
ex of polyphenolics:
- PHBA from ___
- salicylic acid from ___
- PHBA from lotus
- salicylic acid from asian rice
81
what plant is used to standardize effect of algicides
Microcystis aeruginosa
82
ex of N-containing compounds (3)
- alkaloids
- anilines
- AAs
+ derivatives
83
fatty acids/esters:
- structure
- inhibitory effect at temp
- carboxylic acids w long aliphatic chain
- inhibitory effect <35C
84
what increases algicidal effect in fatty acids/esters (3)
- more unsaturation
- shorter C chain
- odd # C chain
85
algicidal mechanisms:
effects on photosynthesis (6)
- abnormality of pigments, protein complex, e-
- changes in photosynthesis expression
- represses synthesis of core proteins
- higher ROS
- responses of endpoints
- apoptosis
86
behavioural/physiological effects of allelochemical:
allomones
effects are favourable to the sender not the receiver
87
behavioural/physiological effects of allelochemical:
repellents
turn away insects
88
behavioural/physiological effects of allelochemical:
locomotor excitants
cause hypermotility
89
behavioural/physiological effects of allelochemical:
suppressants
reduce the overall activity and impact of insect herbivores
90
behavioural/physiological effects of allelochemical:
deterrents
prevent attacks by insect herbivores
91
behavioural/physiological effects of allelochemical:
arrestants
prevent motility
92
behavioural/physiological effects of allelochemical:
digestibility reducing
negatively impact nutrient uptake and use
93
behavioural/physiological effects of allelochemical:
toxins
generally poisonous
94
list of allelochemicals as insecticides (6)
- alkaloids
- terpenoids
- phenolics
- tannins
- salicylic acid
- glycosides, defense proteins & enz
95
attraction of bees to flowers: ___
seed dispersal:
- flavour/aroma: ___
- colour: ___, ___
repellents:
- capsaicin in _______
- hypericin D ____ (from ___)
- flavonoids
- terpenoids; flavonoids, carotenoids
- hot peppers
- photosensitizes skin; from Saint John's wort
96
Hypericin D:
- effect
- from
- photosensitizes skin
- from Hypericum (Saint John's wort)
97
up-regulation of allelochemicals by what env conditions? (4)
- UV radiation in sunlight
- day length
- stress (protect against oxygen radicals)
- elicitors (phytoallexins)
98
antibiosis def & effect
deleterious impact on well-being of insect herbivores
- mild or fatal, through life cycle disruption/reprod success
99
rice plant resistance against rice gall midge is an example of _____
antibiosis
100
types of plant resistance against insect herbivores (3)
- antixenosis (non-preference)
- antibiosis
- tolerance
101
direct vs indirect resistance
direct: morphological traits and secondary metabolites respond to insect herbivores
indirect: reliance on natural enemies for protection
102
T/F direct and indirect resistance exist for both constitutive and induced resistance
true
103
HIPVs stands for? when're they emitted? direct/indirect
herbivore-induced plant volatiles (HIPV)
- emitted w dmg; indirect resistance
- attract predators and parasitoids
104
anti-herbivory compounds are divided into 4 subgroups:
- cyanogenic glycosides & glucosinolates
- polyphenolics
- nitrogen compounds
- terpenoids
CPNT
105
diversity of angiosperms during ___ period -> sudden speciation in insects
Cretaceous!
106
new patterns of feeding from coevolution from plants and insects incl
sap sucking, leaf mining, gall forming, nectar feeding
107
morphological defense in plants incl
waxy cuticles, spines, setae, trichomes, thorns, hardened leaves, granular minerals, divaricated branching
108
T/F specialists are immune to defense mechanisms of host plants
false
109
parsnip webworms eat ____
furanocoumarins
110
oleander aphids eat _______ on _____
jasmonic acid on sandhill milkweed
111
monarch caterpillars eat ________ on _____
jasmonic acid and SA in sandhill milkweed
112
tobacco hornworms eat _____
nicotine
113
cabbage caterpillars are poisoned by _____
isothiocyanates
114
caterpillars prefer to feed on flowers in Brassicae because they have more _____
glycosinolates -> higher growth rate
115
T/F digestibility reducers are effective against ALL insects; toxins can be overcome by specialists
true! but both generalists and specialists can overcome digestibility reducers too
116
example of generalist that eats cardenolides?
monarch caterpillars (D. plexippus) feed only on plants w cardenolides, and sequester as antipredator defense
117
monarch caterpillars are immune to cardenolides
no, too much cardenolides can kill early instar larvae
118
how do cardenolides taste?
bitter!
119
how do cardenolides defend?
disrupt Na/K flux (membrane)
120
when do phytotoxins come out?
with chewing dmg
121
generalists ___ induced responses and specialists ___ induction of high lvls of protection
suppress
minimize
122
induction of indirect defenses is strong if the specialist is not actively__________?
sequestering toxins
123
compounds like phenol, tannin, peroxidase, polyphenol oxidase, Bt proteins can ___ insect pop
suppress
124
compounds like alkaloids, phenolics, cyanogenic glucosides, polyacetylenes and polythienyls show ___ activity
biocidal
125
geranium makes ____ in petals to defend against _____
effect?
quisqualic
japanese beetles
paralyze within 30min
126
are phytoanticipins always synthesized in plants? ex
yes!
- activate constitutive resistance against corn earworm
127
induced defense is only __ or ___ insect attacks
during or after
128
terpenoids, aromatics, and fatty acids have ___ molecular weight & produced ___ insect dmg
high
after
129
what effect do terpenes from neem have on lepidopteran larvae?
stimulatory effects on chemosensory receptor cells, affect receptors in other organs
130
consistent foliar pattern over growing season with ______(bicyclic monoterpene) present in spring;
____ increased during growing season
- delta-3-carene
- bornyl acetate
131
himachallol and beta-himachalene toxic against?
pulse beetles
132
what do hyperactivity/hyperexcitation result in?
rapid known-down & immobilization
133
insecticidal allelochemical types list (7)
- alkaloids
- terpenoids
- phenolics
- tannins
- salicylic acid
- lignin
- glycosides, defense proteins, enz
134
what do alkaloids affect?
- nerve transmission in insects
- disturb membrane + cytoskeleton
-> leakage of cell
135
how do alkaloids taste? what abt for specialist insects
bitter
- specialists: can be aversive or feeding stimulant
136
T/F jacobine and erucifoline are the most effective pyrrolizidine alkaloids (PAs) against insect herbivores
true!!
137
how do pyrrolizidine alkaloids help w defense?
feeding repellent
138
when are pyrrolizidine alkaloids induced?
dmg to plant roots
139
2 configurations for PAs? which is more common in roots
- tertiary free base (~35%)
- N-oxide (MOST of PAs in roots and overall!)
140
what is cool abt PAs
toxic when reduced to highly unstable toxic pyrroles, not original structure! (S. exigua)
likely by P450 enzymes in gut
141
is N-oxide of PA non-toxic? why or why not?
it is nontoxic!
unable to pass through membranes, cannot be converted into toxic pyrroles directly
142
some generalists can excrete PAs & avoid toxins? if so who
yeah! Spodoptera littoralis
143
does theobromine have a therapeutic use currently?
nope
144
theobromine is the main alkaloid in?
cacao bean husks
145
theobromine occurs naturally in (3);
used mainly to make?
- chocolate, tea, cocoa prod
- caffeine
146
past therapeutics for theobromine (4)
- diuretics
- myocardial stimulants
- vasodilators & smooth muscle relaxants
- salt form to dilate coronary arteries
147
what does theobromine metabolism affect
diff toxicity
148
direct contact of insects w nicotine leads to?
paralysis and eventualy death
149
if tobacco leaf is wounded, plants immediately release a "___" of distress chemicals, called _____
bouquet
GLVs (green leaf volatiles)
150
what do GLVs contain?
long fatty acid chains!
151
nightshade makes ___, which has a __________ effect (2)
atropine
- neurotoxic
- cardiac stimulant
152
nicotine is made and kept in ____;
released when insects feed on leaves and ____ ____
vacuoles;
break vacuoles
153
alpha-pinene + 3-carene: (repel/attract)
- B piniperda
- D frontalis
- D brevicomis
repel
attract
attract
154
"defense against insect pests relies on terpenoids and polyphenols accumulated in ____ ____ of ____"
- are they equally distributed?
resin canals of xylem
- equally distributed through shoots & roots
155
plant steroids and sterols are made with _____ or ____ precursors
vit D or glycosides precursors
156
resin volatiles are present in hemlock; resistance to ________
- also results in accumulation of _______ and _______
woolly adelgid infestation
- accumulation of benzyl alcohol & methyl salicylate
157
monoterpenoid esters, known as ____, are made by chrysanthemum and are neurotoxic for insects
pyrethrin!!!
158
what are pyrethroids (permethrin and cypermethrin)
commercially avail neurotoxic insecticides (synthetic ver of pyrethrins)
159
how/where are diterpenes and carotenoids made?
non-mevalonic acid pathway; plastid organelles
160
in cotton, ___ has isoprene units that's found in __ and ___;
what effect on insects?
gossypol
- latex
- resins
feeding deterrent!
161
what causes poisonous leaves of rhododendron?
diterpenes
162
how does spinach disrupt larval growth and cause death?
makes phytoecdysones!
163
azadirachtin and citronella are ___ (___) and isolated from? why?
limonoids (triterpenoids)
- neem trees, lemon grass
insect attraction/pollination
164
how is citronella used for us?
insect repellent
165
saponins are ___ ____ in cell membranes of some plants
glycosylated triterpenoids
166
how do saponins work?
disrupt cell membrane
167
phenolics pathway & structure
- shikimate-phenylpropanoids-flavonoids pathways
- aromatic 6C ring + hydroxyl group
168
how do plants use phenolic/phenol comopunds?
resistance to insects and pathogens
- some parts are insoluble + not digestible for insects (inefficient)
169
lignin, silymarin, cannabinoids are main examples of ___ used in plant defense
phenolics
170
what promotes oxidative stress in aphids & tissues,
& resistance in mango and brinjal against insects
phenolics! (soluble parts)
171
tannins are prone to ___ in insects under high ____ conditions
oxidization
alkaline
172
tannins are prone to oxidization in insects under high alkaline conditions; leads to?
semi-quinone radicals and quinones
- toxic at high conc
173
tannins:
ellagitannins and gallotannins
- common? toxic?
common! insect toxicity!
174
tannins:
what are 2 constituent elements of plant cell walls
silica and lignin
175
tannins are:
- soft/rigid
- insoluble/soluble
- digestible/indigestible
for insects
rigid, insoluble, indigestible
- grind down mandibles
176
tannins: betulinic acid has very high ___ activity against all stages of Papilio demoleus
antifeedant
177
tannins: why are furanocoumarins highly toxic?
integration into DNA, rapid cell death
178
tannins: anthocyanins and phytoalexins act as?
insect growth inhibitors
179
4 general possible effects of tannins for defense?
- repellent
- deterrent
- growth inhibitor
- death at high dose
180
salicylic acid structure
- aromatic ring with hydroxyl group
181
T/F salicylic acid is involved in:
1) lignin production
2) abiotic stress regulation
3) allelopathy
4) pest resistance
yep
182
in Arabidopsis thaliana, salicylic acid plays a big role in ___ resistance
disease
183
salicylic acid: resistance in ____ aginst Helicoverpa armigera (cotton bollworm);
how?
groundnut
- larval survial, activity of enz
184
how do SA and jasmonic acid signaling pathways work?
mediate INDUCED defense responses by expressing NEG CROSSTALK b/w plant and insect
185
lignin: main roles
structural support
resistance to a/biotic stress
186
lignin: product of ___ pathway
phenylpropanoid
187
lignin:
"monolignols and precursors are made in ER and moved as monolignol-glucosides to cell wall, where lignin is deposited" key points
- made in ER
- moved to cell wall
188
is lignin only for physical protection?
no, can also make toxic byproducts from enz involved in lignin polymerization (phenoloxidase)
189
T/F cyanogenic glycosides are produced by plants and should be made for pest control, but also need to be removed in other crops for food safety
yes!
190
glucosinolate stops feeding activity how?
smells pungent during enz metabolism
- turned into isothiocyanates
191
T/F proteinase inhibitors delay larval development and causes death?
false, only delay larval development, does not cause death
192
where are protein inhibitors usually?
where attack is likely to happen:
seeds, bulbs, leaves
193
alpha-amylase inhibitors are proteins found in legumes that inhibit _______
starch digestion! (amylase)
194
taxol is for? found in? why is this a problem?
- breast cancer treatment
- bark of Pacific Yew tree
slow-growing, low supply
195
why is synthesis of taxol complex?
many chiral centers
196
precursor of taxol
10-deacetylbaccatin III
197
what does taxol directly impact?
microtubules!!! affects mitosis and cytoskeleton
198
difference between taxol and colchicine:
use AND mechanism
taxol: stabilizes microtubules; can't polymerize/depolymerize
colchicine: microtubule disassembly
(only used to study cancer, not for treating)
199
effect of light on taxol production in endophytic fungus in bark
- stops making taxol when exposed to light
- makes more OPSIN (for light protection)
- dependent on light exposure length
BIOL 439
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