Lignans & Lignin

6/14/2017
LIGNANS & LIGNIN
naturachem67@gmail.com
 PLANTLIST
 IPNI
 KEW
 SCIENCEDIRECT
 PUBMED
http://gen.lib.rus.ec/scimag/
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 The term “Lignan” was first introduced by Haworth (1948) to

describe a group of dimeric phenylpropanoids where two C6-C3
are attached by its central carbon (C8),
 More recently, Gotlieb (1978) proposed that micromolecules with

two phenylpropanoid units coupled in other manners, like C5-C5´
for example should be named “neolignans” (Umezawa, 2003).
 According to Gordaliza et al (2004), lignans can be found in more
than 60 families of vascular plants and have been isolated from
different plant parts, exudates and resins.
 Lignans are typically found as dimeric

phenylpropanoids derivatives and are found
in woody tissues and resin of plants.
 Most of lignans are free form, seldom as
glycoside.
 They have antitumor, antiviral, liver
protective, etc. activities.
 The two phenylpropanoid units mostly
linked through the β-C atom of the C3 side
chains.
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Properties:
Colourless crystal, no volatility, insoluble in

water, soluble in organic solvents.
 Optical Activity: one or more chiral center.
 The optical activity is related to biological
activities.
 The optical activity is easily changed by acid.
Biosynthesis of Lignan & Lignin
 lignins and lignans are both originated from C6-C3 units,

thus indicating that these metabolites are biosynthesized
through the same pathway in the earlier steps.
 aromatic aminoacids L-phenylalanine and L-tyrosine are
produced from shikimic acid pathway, and then
converted in a series of cinnamic acid derivatives.
 The reduction of these acids via coenzyme A of related
esters and aldehydes forms three alcohols (p-coumaryl
alcohol, coniferyl alcohol and sinalpyl alcohol) that are
the main precursors of all lignins and lignans.
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Lignans vs Lignin
Lignans
 Lignans (and neolignans) are Lignin
 Lignin is a complex aromatic biopolymer formed of hydroxycinnamyl
dimers of hydroxy cinnamyl alcohols, which are connected to each other with various linkages . It is
alcohols. three-dimensional in structure and is formed between other constituents
of the cell wall, having covalent linkages to cellulose, hemicelluloses and
 Lignans function in plants not proteins.
well understood.  The most important function of lignin is to strengthen the cell walls of
plants
 Lignans are differrentiated  Lignin is the 2nd most abundant source of organic material on the earth
after oxidative coupling. (cellulose).
 Lignin has no ordered, repeating structure, but has secondary structure.
 Lignin is racemic, or mosty racemic, polymer on the order of 10K Daltons;
lignans are always chiral owing to a stereocontrolled oxidative coupling.
 Still not much known with regards to the assemblage process of lignin;
significantly more about lignans is known.
 Monomeric constitution of lignin highly dependant on specific plant, but
mostly p-coumaryl, coniferyl, and sinapyl alcohols.
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Podophyllotoxin: 2 C6C3
[Coniferylalcohol]
 Dried root & rhizhome of Podophyllum peltatum [May apple, mandrake]
(Berberidaceae) USA & Canada
 Structure elucidated in 1930’s; planar structure with 4 chiral centers
 C2H5OH extract = Podophyllin (20% podophyllotoxin, 10% β-peltatin, 5% α-
peltatin)
 Traditionally as cathartic, purgative, antiviral, warts remedy
 Trans lactone ring is essential for anti-tumor action; aromatization of ring
C↓activity. Too toxic to be used clinically!
 [OH-] converts into inactive isomer (e.g.epi-podophyllatoxin)
 Classified as microtubule inhibitor [inhibits polymerization of tubulin and stop
cell division at the beginning of metaphase]
Etoposide and teniposide
 As semisynthetic anticancer agents developed from 4’-

demethylepipodophyllotoxin
 They act as Topo II inhibitors (prevention of DNA synthesis and replication)
 Etoposide : small cell lung cancer, breast cancer, leukemia & Hodgkin’s
disease,…
 Teniposide : brain and bladder cancer,…
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Nordihydroguaiaretic Acid
 Isolated from the leaves of Larrea divaricata

HO
 12% yield
HO
 NDGA is a proven antioxidant
 Used in fats and oils in food.
 Produced synthetically from petroleum based
OH starting material.
OH
Medicinal uses
 Large amount of research devoted to investigating

medicinal properties of lignans.
 Particularly from tropical hardwoods and grasses.
 Example 1999 reference: 35 lignans isolated from the twigs of Tazus
mairei (a shrub) for possible use as drugs.
 Studies have found certain medicinal properties:
 Antiviral, antitumor , antioxidant
 Lignans are phytoestrogens
 These are compounds produced by plants which are similar
in structure to oestrogen and ehibit oestogenicity.

Lignans & Lignin

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6/14/2017

LIGNANS & LIGNIN

 The term “Lignan” was first introduced by Haworth (1948) to

 More recently, Gotlieb (1978) proposed that micromolecules with

 Lignans are typically found as dimeric

Colourless crystal, no volatility, insoluble in

Biosynthesis of Lignan & Lignin

 lignins and lignans are both originated from C6-C3 units,

Etoposide and teniposide

 As semisynthetic anticancer agents developed from 4’-

 Isolated from the leaves of Larrea divaricata

 Large amount of research devoted to investigating

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