(Tea & Ruta).pdf

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1. PHENYLPROPANOIDS AND FLAVONOIDS
TEA AND RUTA
DR. SUNITA PANCHAWAT
Assistant Professor
Department of Pharmaceutical Sciences
MLSU, Udaipur

2. Phenylpropanoids
•Thephenylpropanoidsareafamilyof
organiccompoundswithanaromatic
ringandathree-carbonpropenetailof
coumaricacid,andaresynthesizedby
plantsfromtheaminoacids
phenylalanineandtyrosineviashikimic
acid pathway.

3. •Thephenylpropanoidpathwaystarts
from the aromatic amino
acidphenylalanine(Phe,withthe
phenylpropanoidmoietyC
6–C
3)and
leadstoderivativeswithone,two,or
morearomaticrings(C
6),eachringwitha
characteristicsubstitutionpattern,and
withdifferentmodificationsofthe
propaneresidueofPhe(C
3).

4. •Phenylpropanoidcompoundsconstitutea
broadrangeofstructuralcyclic
substances.Theyareformedasaresultof
deaminationoftheaminoacid
phenylamineby the enzyme
phenylalanine-ammonialyase(PAL).
•Phenylpropanoidscanbestructurally
differentduetohydroxylation,
glycosidation,alkylation, phenylation,
sulfatationandmethylation.

5. Functions:
1.Phenylpropanoidserveasessential
componentsofanumberofstructural
polymers.
2.Theyprovideprotectionfromultraviolet
light.
3.Theyprotectplants,defendagainst
herbivoresandpathogens.
4.Phenylpropanoidsmediateplantpollinator
interactionsasfloralpigmentsandscent
compounds.

6. Classification:
Thereisstillnogenerallyaccepted
classificationofthisgroupofcompounds.
Classificationisbasedoncurrent
impressionsofthebiosynthesisof
phenoliccompounds.Phenylpropanoids
canconvenientlybetreatedasalarge
classofnaturalcompoundsconsistingof
thefollowinggroups;

7. I.Simplephenylpropanoids;
a.Cinnamylalcoholsandtheirderivatives(ethers,
glycosides).
b.Cinnamicacidsandtheirderivatives(esters,glycosides,
otherderivatives).
c.Cinnamides
d.Phenylpropanes.
II.ComplexPhenylpropanoids;
a.Phenylpropanoidglycosidesbasedonphenylethanes.
b.Oxidativecouplingproducts(lignoids):flavolignans;
xanthonolignans;coumarinolignans;alkaloidolignans;
neolignans;lignans(dimersandoligomersof
phenylpropanoids).

8. III.Biogeneticallyrelatedphenylpropanoids
(flavonoids,coumarins).
FLAVONOIDS
Flavonoids(Latinwordflavusmeaningyellow)are
secondarymetabolitesofplantsandfungus.Chemically,
flavonoidscontain15-carbonskeleton,whichconsists
oftwophenylrings(AandB)andaheterocyclicring(a
threecarbonbridge,C).Thiscarbonstructurecanbe
abbreviatedC6-C3-C6.

9. Functions:
1.Toattractpollinatoranimalsflavonoidsplay
importantroleasplantpigmentsforflower
coloration,producingyelloworred/blue
pigmentationinpetals.
2.FlavonoidsinhigherplantsinvolvedinUVfiltration,
nitrogenfixationandfloralpigmentation.
3.Theymayalsoactaschemicalmessengers,
physiologicalregulatorsandcellcycleinhibitors.
4.FlavonoidsincombinationwithRhizobialivinginsoil
canleadtoroothairdeformationandseveralcellular
responsessuchasionfluxesandtheformationofa
rootnodule.

10. Classification:
I.Flavones-RingAissubstitutedbytwophenolic
hydroxylgroupatC-5,C-7.Theyhaveadoublebond
betweenpositions2and3andaketoneinposition4of
theCring.Theserepresentsmajorityofflavonoids.
Flavonesarewidelypresentinleaves,flowersandfruits
asglucosides.Celery,parsley,redpeppers,chamomile,
mintandginkgobilobaareamongthemajorsourcesof
flavones.Examples:Apigenin,Luteolin,Parsley-Apin,
Buchu-Diosmin.

11. II.Flavonols
Comparedwithflavones,flavonolshaveahydroxylgroup
inposition3oftheCring,whichmayalsobe
glycosylated.Flavonolsareflavonoidswithaketone
group.Theyarebuildingblocksofproanthocyanins.
Examples;Buckwheat-Rutin,Ring(Crategus
oxycantha)-Quereitrin.
III.Flavanones
Flavanones,alsocalleddihydroflavones,havetheCring
saturated;therefore,unlikeflavones,thedoublebond
betweenpositions2and3issaturatedandthisisthe
onlystructuraldifferencebetweenthetwosubgroups
offlavonoids.Example;Lemon,sweetorange-
Hespiridin,Bitterorange.

12. IV.Flavanonols
Flavanonols,alsocalleddihydroflavones,arethe3-hydroxy
derivativesofflavanones;theyareanhighly
multisubstitutedsubgroup.Examples:Taxifolin
(dihydroquercetin),dihydrokaemferol.
V.Isoflavones
Asanticipated,isoflavonesareasubgroupofflavonoidsin
whichtheBringisattachedtoposition3oftheCring.
Examples:Sharapunkha-Tephrosin.
VI.Flavanols
Flavnolsarealsoreferredascatechinsaswellflavan-3-ols.
Inflavanolshydroxylgroupisalmostalwaysboundto
position3ofCring.Examples:Catechin,Epicatechin.

13. VII.Anthocyanidins
Anthocyanidinsaretheaglyconesofantocyanins;theyasethe
flavylium(2-phenylchromenyylium)cations.Sugarunitsare
boundmostlytoposition3oftheCringandtheyareoften
conjugatedwithphenolicacids,suchasferulicacid.They
aretheonlygroupofflavonoidsthatgivescolortoplants
(allotherflavonoidsarecolorless).Examples:Pelargonium
flower-Plargonidin,Petuniaflower-Petunidin.
VII.Chalcones
Chalconesdonothavecentralheterocyclicnucleusandare
characterizedbythreecarbonchainwithaketonefunction
andα,βunsaturation.Chalconesareflavonoidswithopen
structure;theyareclassifiedsbecausetheyhavesimilar
syntheticpathways.Examples:Safflorred-Carthamin.

14. Chemical Tests
1.Shinodatest-To dry powder or extract, add 5 ml of
95% ethanol, few drops of concentrated hydrochloric
acid and four pieces of magnesium turnings. A pink or
red colour indicates the presence of flavonoid. Colours
varying from orange to red indicated flavones, red to
crimson indicated flavonoids, crimson to magenta
indicated flavonones.
2.Sodium hydroxide test-About 5 mg of the compound
is dissolved in water, warmed and filtered. 10%
aqueous sodium hydroxide is added to 2 ml of this
solution. This produces a yellow coloration. A change
in colour from yellow to colorless on addition of dilute
HCl is an indication for the presence of flavonoids.

15. TEA AND RUTA

16. TEA
Synonym-Teaplant,TeaShrub,Camelliathea
Biologicalsource-Itconsistsofdriedleavesand
leafbudofTheasinensis,Family:Theaceae
Distribution-India,China,Shrilanka,Indonesiaand
Japan.
BlackTea(IndiaandShrilanka)
GreenTea(ChinaandJapan)

18. ChemicalConstituents-Polyphenols,Catechins
(flavanols).
Majorcatechinsare(-)-epicatechingallate,(-)-
epicatechin.
Othercompoundsarepurinealkaloidsviz.,
caffeine,theophyllineandtheobromine.Trace
compoundspresentinteaareaminoacids,
carbohydrates,proteins,chlorophyll,volatile
organiccompounds,fluoride,aluminium,
minerals,blackandgreenteaareextremely
goodsourceofVitaminC.

27. Uses
1.Purine alkaloids (caffeine, theophyllineand
theobromine)are CNS stimulant and diuretic.
2.Catechins have antioxidant, anticancer and anti-
ageing effects.
3.Green tea used in obesity and weight loss
treatment.

28. RUTA
Synonym-Rue,Gardenrue,Germanrue,Sadab.
Biologicalsource-Itconsistsoffreshanddried
leavesofRutagraveolensL.,Family:Rutaceae
Distribution-ItisnativetotheBalkanPeninsula.It
isnowgrownthroughouttheworldingardens.

31. Chemical Constituents
Glycosides: Flavonoidrutin
Alkaloids: Coquisagenine, skimmianineand
graveoline, furanocoumarins(psoralens),
bergapteneand xanthotoxine.
Volatile oil: Methyl-nonyl-ketone, methyl-n-octyl-
ketoneand methyl-heptyl-ketone.
Alcohol: Methyl-ethyl-carbinol, pinene and
limonenes.
Flavonoid: Rutinand Quercetin

32. Uses
-Rue is used for painful conditions including
headache, arthritis, cramps and muscle spasms.
-In Chinese medicine rue is considered as an
emmenagogue, hemostat, intestinal
antispasmodic, sedative, uterine stimulant,
vermifuge, rheumatism, cold and fever.
-In Poland it is used as an aphrodisiac and
choleretic.
-Medicinally it is used as bitters, an aromatic
stimulant, ecbolicand in suppression of the
menses.