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Lignans and flavonoids
T.Y.B.Pharm
2018
Lignans
When food containing, lignan precursors are
consumed they are converted to the enterolignans,
enterodiol and enterolactone, by bacteria that
normally colonize the human intestine.
Enterodiol and enterolactone have weak estrogenic
activity but may also exert biological effects through
nonestrogenic mechanisms.
. Because enterodiol and enterolactone can mimic
some of the effects of estrogens, their plant-derived
lignan precursors are classified as phytoestrogens.
Lignan precursors that have been identified in the
human diet include pinoresinol, lariciresinol,
secoisolariciresinol, matairesinol, and others
Introduction Lignans
The term “Lignan” was first introduced by Haworth (1948) to describe a group of dimeric
phenylpropanoids where two phenylpropanoid molecules are attached by its central
carbon (C8). Lignans are a subgroup of non-flavonoid polyphenols.
They are widely distributed in the plant kingdom, being present in more than 55 plant
families, where they act as antioxidants and defence molecules against pathogenic fungi
and bacteria.
Flowing structure contains
a) Phenylpropanoid and b) Lignan
a) Phenylpropanoid unit; b) Lignan structure
Chemical structure of lignans
Their basic chemical structure consists of two phenylpropane unitslinked by a
C-C bond between the central atoms of the respective side chains (position 8
or β), also called β-β’ bond; in these cases the dimers are called neolignans.
Hence, their chemical structure is referred to as (C6-C3)2, and they are included
in the phenylpropanoids group, as well as their precursors:
the hydroxycinnamic acids
Fig. 1 – Phenylpropane unit
Lignans can be found in more than 60 families of vascular plants
and have been isolated from different plant parts, exudates and
resins.
Biological activity of Lignans -are Antiviral ,Anticancer ,Cancer
prevention, Anti-inflammatory, antimicrobial ,antioxidant ,
immunosuppressive, Hepatoprotective, Osteoporosis prevention.
Based on their carbon skeleton, cyclization pattern, and the way in
which oxygen is incorporated in the molecule skeleton, they can be
divided into 8 subgroups:
Main subclasses of Lignans- 1.Furofuran, 2.Furan,
3.Dibenzylbutane, 4.Dibenzylbutyrolactol,
5.Dibenzylbutyrolactones, 6.Aryltetralin, 7.Arylnaphtalene,
8.Dibenzocyclooctadienes.
among these subgroups, the furan, dibenzylbutane and
dibenzocyclooctadiene lignans can be further classified in “lignans
with C9 (9´)-oxygen” and “lignans without C9 (9´)-oxygen”
Furofuran Furan
Dibenzylbutane
They are not present in the free form in nature, but linked to
other molecules, mainly as glycosylated derivatives.
Among the most common lignans, secoisolariciresinol (the most
abundant one), lariciresinol, pinoresinol, matairesinol and 7-
hydroxymatairesinol are found.
 Podophyllotoxin , a naturally occurring aryltetralin lignin, is one
of the most important compound due to its high toxicity and current
use as a local antiviral agent . podophyllotoxin, obtained from plants
of the genus Podophyllum ( Berberidaceae family); it is a mitotic
toxin whose derivatives have been used as chemotherapeutic
agents;
Food rich in lignans
The richest dietary source is flaxseed (linseed), that contains mainly
secoisolariciresinol, but also lariciresinol, pinoresinol and
matairesinol in good quantity . They are also found in sesame
seeds, whole grains.
Biosynthesis of lignans
The pathway starts from 3 of the 4 most common dietary hydroxycinnamic acids: p-coumaric
acid, sinapic acid, and ferulic acid (caffeic acid is not a precursor of this subgroup
of poyphenols). Therefore, they arise from the shikimic acid pathway, via phenylalanine.
The first three reactions reduce the carboxylic group of the hydroxycinnamates to alcohol
group, with formation of the corresponding alcohols, called monolignols, that is, p-coumaric
alcohol, sinapyl alcohol and coniferyl alcohol. These molecules also enter the pathway of
lignin biosynthesis.
The first step, which leads to the activation of the hydroxycinnamic acids, is catalysed by
hydroxycinnamate:CoA ligases, commonly called p-coumarate:CoA ligases , with formation of
the corresponding hydroxycinnamate-CoAs, namely, feruloil-CoA, p- coumaroyl-CoA and
sinapil-CoA.
In the second step, a NADPH-dependent cinnamoyl-CoA: oxidoreductase, also called
cinnamoyl-CoA reductase catalyzes the formation of the corresponding aldehydes, and the
release of coenzyme A.
In the last step, a NADPH-dependent cinnamyl alcohol dehydrogenase, also called monolignol
dehydrogenase , catalyzes the reduction of the aldehyde group to an alcohol group, with the
formation of the aforementioned monolignols.
The next step, the dimerization of monolignols, involves the
intervention of stereoselective mechanisms, or, more precisely,
enantioselective mechanisms. plant lignans exists as (+)- or (-)-
enantiomers,
Hydroxycinnamic acids (hydroxycinnamates) are a class of
aromatic acids or phenylpropanoids having a C6–C3 skeleton.
These compounds are hydroxy derivatives of cinnamic acid.
Biosynthesis of lignans
lignans
lignans
lignans
Flavonoids
Flavonoids are the most abundant polyphenols in human diet, over 4000 have
been identified. Latin word flavus meaning yellow, their color in nature. many of
which are responsible for the attractive colors of flowers, fruits and leaves. In
plants, these compounds afford protection against ultraviolet radiation,
pathogens, and herbivores .
In fruits and vegetables, they are usually found in the form of glycosides and
sometimes as acylglycosides . characterized by the flavan nucleus
Chemically, flavonoids have the general structure of a 15-carbon skeleton, which
consists of two phenyl rings (A and B) and heterocyclic ring (C).
flavan nucleus
Classification of flavonoids-
They can be subdivided into different subgroups depending on the
carbon of the C ring on which B ring is attached, and the degree of
unsaturation and oxidation of the C ring.
Flavonoids in which B ring is linked in position 3 of the ring C are
called isoflavones;
those in which B ring is linked in position 4, neoflavonoids,
 while those in which the B ring is linked in position 2 can be further
subdivided into several subgroups on the basis of the structural
features of the C ring. These subgroup are: flavones, flavonols or
catechins, flavanones, flavanonols, and anthocyanins.
Finally, flavonoids with open C ring are called chalcones.
A) Anthoxanthins
1.flavone- Flavones are mainly found in cereals and herbs
eg luteolin,apigenin,tangeritin
2.Flavonol or 3-hydroxyflavone-
Foods rich in flavonols-The major sources in human diet
are:fruit;vegetables;beverages such as red wine and tea.
eg.Quercetin,kaempferol,myricetin,fisetin,galangin,isorhamnetin,pachypodo
l,rhamnazin,pyranoflavonols,furanoflavonols
B) Flavanones: type of flavonoids, are various aromatic, colorless
ketones derived from flavone that often occur in plants as glycosides.
Flavanone-eg. Hesperetin,naringenin,eriodictyol,homoeriodictyol
C)Flavanonols:class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-
phenylchromen-4-one (IUPAC name) backbone.
Flavanonol or 3-hydroxyflavanone or 2,3-dihydroflavonol eg.taxifolin
or dehydroquercetin,dihydrokaempferol
D) Flavans - The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2H-
chromene skeleton include
1. flavan-3-ols (flavanols),- examples are catechin, gallocatechin, catechin 3-gallate,
gallocatechin 3-gallate,epicatechins.
2. flavan-4-ols
3.flavan-3,4-diols.
flavan-3-ols flavan-4-ols flavan-3,4-diols
D) Anthocyanidins - anthocyanidins are the aglycones of
anthocyanins; Anthocyanins are a very large group of red-
blue plant pigments. Anthocyanins occur in all higher
plants, mostly in flowers and fruits but also in leaves,
stems, and roots. They are very good antioxidants
Health benefits of flavonoids-Their regular consumption is
associated with reduced risk of a number of chronic
diseases, including cancer, cardiovascular disease (CVD)
and neurodegenerative disorders. thy are good
antioxidant and anti-inflammatory ,
Biosynthesis of flavonoids

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Lignans and flavonoids

  • 2. Lignans When food containing, lignan precursors are consumed they are converted to the enterolignans, enterodiol and enterolactone, by bacteria that normally colonize the human intestine. Enterodiol and enterolactone have weak estrogenic activity but may also exert biological effects through nonestrogenic mechanisms. . Because enterodiol and enterolactone can mimic some of the effects of estrogens, their plant-derived lignan precursors are classified as phytoestrogens. Lignan precursors that have been identified in the human diet include pinoresinol, lariciresinol, secoisolariciresinol, matairesinol, and others
  • 3.
  • 4.
  • 5. Introduction Lignans The term “Lignan” was first introduced by Haworth (1948) to describe a group of dimeric phenylpropanoids where two phenylpropanoid molecules are attached by its central carbon (C8). Lignans are a subgroup of non-flavonoid polyphenols. They are widely distributed in the plant kingdom, being present in more than 55 plant families, where they act as antioxidants and defence molecules against pathogenic fungi and bacteria. Flowing structure contains a) Phenylpropanoid and b) Lignan a) Phenylpropanoid unit; b) Lignan structure
  • 6. Chemical structure of lignans Their basic chemical structure consists of two phenylpropane unitslinked by a C-C bond between the central atoms of the respective side chains (position 8 or β), also called β-β’ bond; in these cases the dimers are called neolignans. Hence, their chemical structure is referred to as (C6-C3)2, and they are included in the phenylpropanoids group, as well as their precursors: the hydroxycinnamic acids Fig. 1 – Phenylpropane unit
  • 7. Lignans can be found in more than 60 families of vascular plants and have been isolated from different plant parts, exudates and resins. Biological activity of Lignans -are Antiviral ,Anticancer ,Cancer prevention, Anti-inflammatory, antimicrobial ,antioxidant , immunosuppressive, Hepatoprotective, Osteoporosis prevention. Based on their carbon skeleton, cyclization pattern, and the way in which oxygen is incorporated in the molecule skeleton, they can be divided into 8 subgroups: Main subclasses of Lignans- 1.Furofuran, 2.Furan, 3.Dibenzylbutane, 4.Dibenzylbutyrolactol, 5.Dibenzylbutyrolactones, 6.Aryltetralin, 7.Arylnaphtalene, 8.Dibenzocyclooctadienes. among these subgroups, the furan, dibenzylbutane and dibenzocyclooctadiene lignans can be further classified in “lignans with C9 (9´)-oxygen” and “lignans without C9 (9´)-oxygen”
  • 9. They are not present in the free form in nature, but linked to other molecules, mainly as glycosylated derivatives. Among the most common lignans, secoisolariciresinol (the most abundant one), lariciresinol, pinoresinol, matairesinol and 7- hydroxymatairesinol are found.  Podophyllotoxin , a naturally occurring aryltetralin lignin, is one of the most important compound due to its high toxicity and current use as a local antiviral agent . podophyllotoxin, obtained from plants of the genus Podophyllum ( Berberidaceae family); it is a mitotic toxin whose derivatives have been used as chemotherapeutic agents; Food rich in lignans The richest dietary source is flaxseed (linseed), that contains mainly secoisolariciresinol, but also lariciresinol, pinoresinol and matairesinol in good quantity . They are also found in sesame seeds, whole grains.
  • 10. Biosynthesis of lignans The pathway starts from 3 of the 4 most common dietary hydroxycinnamic acids: p-coumaric acid, sinapic acid, and ferulic acid (caffeic acid is not a precursor of this subgroup of poyphenols). Therefore, they arise from the shikimic acid pathway, via phenylalanine. The first three reactions reduce the carboxylic group of the hydroxycinnamates to alcohol group, with formation of the corresponding alcohols, called monolignols, that is, p-coumaric alcohol, sinapyl alcohol and coniferyl alcohol. These molecules also enter the pathway of lignin biosynthesis. The first step, which leads to the activation of the hydroxycinnamic acids, is catalysed by hydroxycinnamate:CoA ligases, commonly called p-coumarate:CoA ligases , with formation of the corresponding hydroxycinnamate-CoAs, namely, feruloil-CoA, p- coumaroyl-CoA and sinapil-CoA. In the second step, a NADPH-dependent cinnamoyl-CoA: oxidoreductase, also called cinnamoyl-CoA reductase catalyzes the formation of the corresponding aldehydes, and the release of coenzyme A. In the last step, a NADPH-dependent cinnamyl alcohol dehydrogenase, also called monolignol dehydrogenase , catalyzes the reduction of the aldehyde group to an alcohol group, with the formation of the aforementioned monolignols.
  • 11. The next step, the dimerization of monolignols, involves the intervention of stereoselective mechanisms, or, more precisely, enantioselective mechanisms. plant lignans exists as (+)- or (-)- enantiomers, Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid.
  • 13. Flavonoids Flavonoids are the most abundant polyphenols in human diet, over 4000 have been identified. Latin word flavus meaning yellow, their color in nature. many of which are responsible for the attractive colors of flowers, fruits and leaves. In plants, these compounds afford protection against ultraviolet radiation, pathogens, and herbivores . In fruits and vegetables, they are usually found in the form of glycosides and sometimes as acylglycosides . characterized by the flavan nucleus Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings (A and B) and heterocyclic ring (C). flavan nucleus
  • 14. Classification of flavonoids- They can be subdivided into different subgroups depending on the carbon of the C ring on which B ring is attached, and the degree of unsaturation and oxidation of the C ring. Flavonoids in which B ring is linked in position 3 of the ring C are called isoflavones; those in which B ring is linked in position 4, neoflavonoids,  while those in which the B ring is linked in position 2 can be further subdivided into several subgroups on the basis of the structural features of the C ring. These subgroup are: flavones, flavonols or catechins, flavanones, flavanonols, and anthocyanins. Finally, flavonoids with open C ring are called chalcones.
  • 15. A) Anthoxanthins 1.flavone- Flavones are mainly found in cereals and herbs eg luteolin,apigenin,tangeritin 2.Flavonol or 3-hydroxyflavone- Foods rich in flavonols-The major sources in human diet are:fruit;vegetables;beverages such as red wine and tea. eg.Quercetin,kaempferol,myricetin,fisetin,galangin,isorhamnetin,pachypodo l,rhamnazin,pyranoflavonols,furanoflavonols
  • 16. B) Flavanones: type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides. Flavanone-eg. Hesperetin,naringenin,eriodictyol,homoeriodictyol C)Flavanonols:class of flavonoids that use the 3-hydroxy-2,3-dihydro-2- phenylchromen-4-one (IUPAC name) backbone. Flavanonol or 3-hydroxyflavanone or 2,3-dihydroflavonol eg.taxifolin or dehydroquercetin,dihydrokaempferol
  • 17. D) Flavans - The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2H- chromene skeleton include 1. flavan-3-ols (flavanols),- examples are catechin, gallocatechin, catechin 3-gallate, gallocatechin 3-gallate,epicatechins. 2. flavan-4-ols 3.flavan-3,4-diols. flavan-3-ols flavan-4-ols flavan-3,4-diols
  • 18. D) Anthocyanidins - anthocyanidins are the aglycones of anthocyanins; Anthocyanins are a very large group of red- blue plant pigments. Anthocyanins occur in all higher plants, mostly in flowers and fruits but also in leaves, stems, and roots. They are very good antioxidants Health benefits of flavonoids-Their regular consumption is associated with reduced risk of a number of chronic diseases, including cancer, cardiovascular disease (CVD) and neurodegenerative disorders. thy are good antioxidant and anti-inflammatory ,