flavenoids Flashcards by Ang R

flavenoids are derived from ______ (via malonate) and ______

acetate and phenylalanine

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flavenoids are _____ soluble

water

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flavenoids absorb ____ and ____ light, as they are ______

UV and visible
photoactive

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who makes flavenoids and who does not make them

plants make
animals do not make (butterflies get colour via flavenoids in diet)

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flavonoids have ____ structure

polyphenolic

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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

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flavonoids inhibit ______, used by _____ plants for _____/_____. they have a _____ molecular weight

enzymes
higher
defense and growth
low

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T/F: flavenoids only found in flower petals

F bc flavenoids found in all part of plant

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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

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flavenoids play a role in _____ resistance, _____ accimilation and _____ tolerance

drought
heat
freezing

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there are over _____ (#) flavenoids total,
but _____ (#) share ____ (#) skeletons

6000
3000, 24

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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

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classification of flavonoid divided into subgroups based on the _____ that the rings attach to, degree of ____ ,and _____ at that ring

carbon
unsaturation
oxidation

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when B ring is linked in position 3 of C ring = _____-flavonone

iso-flavone

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when B ring is linked in position 4 of C ring = _____-flavonone

neo-flavonoid

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when B ring is linked in position 2 of C ring = _____-flavonone

other subgroups

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FLAVONES
found in leaves, flowers and fruits as _____
sources:
examples:

glucosides
citrus!!, celery, parsley, peppers, mint

a(pig)let talking
apigenin, lutolin, tangeritin

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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,

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ISOFLAVONES
seen in _____ and _____
precursor for synthesis of _____
strong use for ______
examples:

beans and microbes
phytoalexins
defense

GD (german daddy)
genistein and daidzein

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NEOFLAVONOIDS
different backbone because…
example: _____, isolated in what year?
found in ______

no OH group at position 2
calophyllolide, 1951
Sri Lankan tree

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FLAVANOLS
__-hydroxy derivitives of ______
no _____ bond at positions __ and __
seen mostly in

3-OH, flavanones
double, 2=3
fruit

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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

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CHALCONES
no _____ ring, only ____
aka “____-chain flavonoids”
seen in
examples

third, 2
open-chain
tomato, berries, wheat

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___ 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