diversity of terpenoids Flashcards
terpenoids produced in what three areas of cell?
ER, mitochondria and plastids
in what ways are terpenoids diverse? 5 catagoties
chemistry/skeleton
chemical reactions
plant features
stress and enviornmental factors
genetics
what are 5 basic factors that enable terpenoid diversity?
arms race
nature
defense
commensalism
mutualism
how did “arms race” enable diversity of terpenoids?
the ability of plants to make new terpenoids arose via selection - with slow global changes of enviornment, ‘old’ plants with ‘older’ terpenoids weren’t as effective as newer terpenoids
evolution involved in diversity of terpenoids prior to the
emergence of plants
emergence of new _____ that encode for new _______ supports diversity
genes
metabolites
terpeniods were used in the middle east back in the day for
disease treatments, artifacts using amber, scents, waterproofing
the terpenoid beta-carotene is a precursor for
vitamin A
which terpenoids contributes to food colouring and flavour (herbs, spices, wine)
BLAZN
bixin
lycopene
astaxanthin
zingiberne
nootkatone
the antimicrobial and insecticidal properties of terpenoids allows use for
food preservation, mouthwash, disinfectants, insect repellants, etc
these two terpenoids are anti cancer agents because they are toxic to cells:
TV
taxol
vinblastine
hormone terpenoids examples
P(t)SD
progesterone (birth control)
steroids
diosgenin
terpenoids with neuro-toxic effects
C(a)TS
cardenolides
tetrahydrocannabinol (THC)
Salvinorin A
terpenoids can be found in trees: _______ in northern hemisphere and _____ in australia
conifers
eucalyptus
the molecular mechanism to make terpenoids is ____________ reactions
condensation
give a two sentence summary of the terpenoid condensation reaction
- two molecules combine to form single molecule
- results in removal of water
three types of condensation reactions
head to tail
head to head
head to middle
the condensation reactions use _______ _________ instead of _____ _________
prenyl diphosphates
free prenyls
C5 -> _______ terpenoid
hemi
C10 -> _____ terpenoid
mono
C15 -> ______ terpenoid
sesqui
head to tail reaction occurs via ______ and _______ prenyl diphosphates
trans and cis
head to head rxn of 2 trans sesquiterpenyl diphosphates x2 C15 -> C____
ex. of a C___ is ______
C30
sterols
head to head rxn of 2 trans diterpenyl diphosphates x2 C20 -> C____
ex. of a C____ is ______
C40
carotenoid
alpha and beta carotene found in __________ tissue
photosynthetic
absiscic acid and strigolactones are degradation products of ____________
carotenoids
rubber is made of hundreds of C5 units attached to _________ polyprenyl starter
trans
terpenoid rxns catalyzed by ______ _________
terpene synthases (TPSs)
TPSs use _________ __________ as precursors (what is the basic terpene skeleton?)
prenyl diphosphates
___________ —( )—> ___________ intermediates ——-> diverse terpene products
prenyl diphosphates
TPSs
carbocation intermediates
T/F: it take many amino acid mutations in a TPS to produce many new terpenoids
no, it only takes 1 single aa change to produce multiple terpenes
TPS genes occur as a family of ___ - ____ genes per genome, enabling new terpenes to appear through ________ and ________
30-100 genes
mutation and selection
a carbocation is an ion with a _______ charged carbon
positively
carbocations go though ________ reactions which affect ___________
rearrangement reactions
stability
stability of carbocations achieved through ________
resonance
when a carbon skeleton is rearranged, this makes it a _________ ________ of the original molecule
structural isomer
terpenoids interation with water is generally:
hydrophobic or lipophilic
concentration of TRI-terpene sterols in cell membranes affects membrane ________
fluidity
terpenes can be recognized as hormones by specific _______
receptors
a plant can have multiple forms of a hormone due to different _________ reactions
modification
modification reactions help refine the effect of the _________ on the __________
hormone
receptor
how terpenoids used in plants for defence
toxins, repellants, attracting predators
some plants evolved counter-defense mechanisms against predators/herbivores though…
addition of more complex compound or modification of existing molecule
plants adapt the use terpenoids for mutualism. explain
that terpenoid may be toxic to some, but selectivly identfy organisms that are beneficial to the plant
