flavenoids Flashcards
flavenoids are derived from ______ (via malonate) and ______
acetate and phenylalanine
flavenoids are _____ soluble
water
flavenoids absorb ____ and ____ light, as they are ______
UV and visible
photoactive
who makes flavenoids and who does not make them
plants make
animals do not make (butterflies get colour via flavenoids in diet)
flavonoids have ____ structure
polyphenolic
flavenoid characteristics in plants:
in ___ part of plant
flower ______
UV absorbing compounds in leaf ______
_______ scavengers
phyto______ (fungicides)
used for ________
in all parts of plant
flower pigments
UV absorbing compounds in leaf epidermis
free radical scavengers
phytoalexins (fungicides)
used for taxonomy
flavonoids inhibit ______, used by _____ plants for _____/_____. they have a _____ molecular weight
enzymes
higher
defense and growth
low
T/F: flavenoids only found in flower petals
F bc flavenoids found in all part of plant
responsible for ____ and ___ of flowers
___ pollinators
promote ______ dispersion
_____ germination
_____ and ____ of seedlings
protect plants from stress by acting as ___ filters
aroma and flaour
attract
fruit
seed
growth and development
UV
flavenoids play a role in _____ resistance, _____ accimilation and _____ tolerance
drought
heat
freezing
there are over _____ (#) flavenoids total,
but _____ (#) share ____ (#) skeletons
6000
3000, 24
types of flavenoid modifications:
1. most are conjugated to _____ at the OH groups, and glycosides gives _____ solubility
- many are O-____ and O-____ at OH’s, which gives ____ solubility
- chelate metals
- can be _____ized and ______ized
sugars, water
O-methylated, O-acetylated, lipid
dimerized and oligomerized
classification of flavonoid divided into subgroups based on the _____ that the rings attach to, degree of ____ ,and _____ at that ring
carbon
unsaturation
oxidation
when B ring is linked in position 3 of C ring = _____-flavonone
iso-flavone
when B ring is linked in position 4 of C ring = _____-flavonone
neo-flavonoid
when B ring is linked in position 2 of C ring = _____-flavonone
other subgroups
FLAVONES
found in leaves, flowers and fruits as _____
sources:
examples:
glucosides
citrus!!, celery, parsley, peppers, mint
a(pig)let talking
apigenin, lutolin, tangeritin
FLAVANONES
seen mostly in ____
linked to health benefits because…
taste:
beneficial health effects:
examples:
citrus (lemon, orange, grape)
free radical-scavenging activity
bitter
antioxidant, anti-inflammatory, cholestrol lowering
not enjoying home (NEH)
naringenin, eriodicdyol, hesperitin,
ISOFLAVONES
seen in _____ and _____
precursor for synthesis of _____
strong use for ______
examples:
beans and microbes
phytoalexins
defense
GD (german daddy)
genistein and daidzein
NEOFLAVONOIDS
different backbone because…
example: _____, isolated in what year?
found in ______
no OH group at position 2
calophyllolide, 1951
Sri Lankan tree
FLAVANOLS
__-hydroxy derivitives of ______
no _____ bond at positions __ and __
seen mostly in
3-OH, flavanones
double, 2=3
fruit
ANTHOCYANINS
gives fruit _____, which depends on ___ or ____/___ at the OH groups on the joined rings
seen in ___ layer of fruit
examples
colour
PH, acetylation/methylation
outer
MDC (mermadia crustacian delphine)
malvidin, cyanidin, delphinidin
CHALCONES
no _____ ring, only ____
aka “____-chain flavonoids”
seen in
examples
third, 2
open-chain
tomato, berries, wheat
___ classes of flavenoids based on oxidation state of central ____ ring
12
pyran
synthesis of flavonoids:
1._________ pathway to make ________
2. _________ + _______ via ________ ->_______
3. _____ and _____ to make diverse flavonoids
phenylpropanoid
4-coumaroyl CoA
4-coumaroyl CoA
3 malonyl CoA
chalcone synthase
chalcone
redox and modifications
localization of flavanoids in plants: FLOWERS
- antho______
- flavonones as ________
- seen in _____ of petals because contribute to ______
anthocyanins
co-pignments
epidermal, colour
_______ are the precursor to all flavonoids
chalcones
localization of flavanoids in plants: LEAVES
- anthocyanin _______
- ____ colour, examples in veggies ____
- usually in ____ layer
- reflect ___ and ____ with interferaence of ___ to give purple colour
pigmentation
purple, red cabbage, red onion
epidermal
blue and red, interference of chlorophyll
localization of flavanoids in plants:
- UV absorbing pigments in ____ layer of leaves
- in ______ as free radical scavengers
epidermal
mesophyll
localization within plant cell:
- in _____ of cell
- biosynthesis occurs in the ____
- enzymes associated with _____ mebrane around vacuole
vacuole
cytoplasm
tonoplast
flavenoids made in _____, transporteed into _____ when the _____ is attached.
cytoplasm
vacuole
glycosyl
in vacuole, ____ of flavonoids form which gives flower _____.
also seen in chloroplasts/cytoplasm which is important for ________ scavenging.
extracellular flavonoids in waxy layers and cuticles are _______, and examples are ______ and ______
aggregates, colour
free radical
methylated, fungicide, bacteriacide
flower colouring:
- cyan
- pigments = ______
- pyran ring is ____ charged and if attacked by OH, it loses its ______
- ph of vacuole is ____ which ______ protects charge, but still suseptable to OH attack so additional protection done by _____ of the molecules to preserve colour
anthocyanins
positivly, colour
acidic, weakly
aggregation
anthycyanin stabilization ______ via ______. the four types are:
1. intramolecular _______
2. ______ complexity
3. _____ association
4. intermolecular ______
in vivo, aggregation
1. copigmentation
2. metal complexity
3. self association
4. copigmentation
as concentration of anythocyanins increases, ______ saturates
absorbance
T/F: if aggregation occurs, concentration increases in proportion to number of molecules. therefore aggregates absorb as multiple molecules
F: if aggregation occurs, concentration does NOT increase in proportion to number of molecules
dimers, trimers aborb as single molecules; aggregates absorb as a single molecule
for aggregates to form, ______ must be free
4-OH
self association:
anthocyanins stack in ___ fashion, promote __-__ interactions and _____ interactions.
association protects the ___ ring charge from OH- attack
planar
pi-pi
lipophilic
positive
intermolecular co-pignmenation:
- protects anthocyanin ___ charge
- shifts ______ of pigments
- held together by __-__ interactions
- ____ promote association
- ______ (stable/unstable)
- acetylated through _____ groups
- ____ colour
positive
max wavelength
pi-pi
glycosyls
stable
glycosyl
blue
metal complexes:
- aggregate using ____ metal
- ______ complex
Mg2+ colour
large
yellow flower colouring from a combindation of ______ + ______. the wavelenth of transmission is ____-_____
anthocyanins and carotenoids
550-600
flavonoids that absorb UV are synthesized in response to ____, in ____ layer of leaves. absorb at ___-___nm
UVB radiation
epidermal
290-350
flavenoid making mechanisms (x4)
- ____ scavenging
- ____ _____ inhibition
- anti-______
radical
xanthine oxidase
anti-inflammaiton
what step in synthesis of flavonoids is the committal step?
step 2
4-coumaroyl CoA + 3 malonyl CoA via chalcone synthase -> chalcone
modifications of chalcone to make diverse terpenoids
glycosylation, methylation, metalation, oligomerization
T/F: each aggregate has different colour
TRUE!!
cyanoplast is a flavenoid ______
aggregate
photosynthetically active radiation (cisible light) at what nm?
what part of plant does it make flavenoids in (penetrate to)?
400-700nm
mesophyll
UVA radiation at what nm?
what part of plant does it make flavenoids in (penetrate to)?
320-400nm
mesophyll
UVB radiation at what nm?
what part of plant does it make flavenoids in (penetrate to)?
290-320nm
upper epidermis
why is UVB increasing today?
loss of ozone layer
flavenoids are primary or secondary?
secondary
T/F: all flavanoids induced by UVB
false, only some flavanoids induced by UBV
two examples of FLAVONES
a(pig)-let (AL)
apigenin
luteolin
two examples of ISOFLAVONES
german daddy (GD)
genistein and daidzein
two examples of FLAVONOLS
HN (hell no)
hesperetin
narigenin
two examples of FLAVANALS
quite kinky (QK)
quercetin
kaempferol
two examples of CHALCONES
phoney challenges (PC)
phloretin
chalconarigenin
3 examples of ANTHOCYANINS
mermadia crustacian delphine (MCD)
malvidin
cyanidin
deiphindin
