Group of polyphenols in plant matter
The
lignans
are a large group of low molecular weight
polyphenols
found in
plants
, particularly
seeds
,
whole grains
, and vegetables.
[1]
The name derives from the
Latin
word for "wood".
[2]
Lignans are precursors to
phytoestrogens
.
[1]
[3]
They may play a role as
antifeedants
in the defense of seeds and plants against
herbivores
.
[4]
Biosynthesis and metabolism
[
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]
Structures of some lignans
Lignans and
lignin
differ in their molecular weight, the former being small and soluble in water, the latter being high polymers that are undigestable. Both are
polyphenolic
substances derived by oxidative coupling of
monolignols
. Thus, most lignans feature a C
18
cores, resulting from the dimerization of C
9
precursors. The coupling of the lignols occurs at C8. Eight classes of lignans are: "furofuran, furan, dibenzylbutane, dibenzylbutyrolactone,
aryltetralin, arylnaphthalene, dibenzocyclooctadiene, and dibenzylbutyrolactol."
[5]
Many lignans are metabolized by mammalian gut microflora, producing so-called
enterolignans
.
[6]
[7]
Food sources
[
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]
Flax seeds
and
sesame seeds
contain high levels of lignans.
[1]
[8]
The principal lignan precursor found in flaxseeds is
secoisolariciresinol diglucoside
.
[1]
[8]
Other foods containing lignans include cereals (
rye
,
wheat
,
oat
and
barley
),
soybeans
,
tofu
,
cruciferous vegetables
, such as
broccoli
and
cabbage
, and some fruits, particularly
apricots
and
strawberries
.
[1]
Lignans are not present in
seed oil
, and their contents in whole or
ground
seeds may vary according to geographic location, climate, and maturity of the seed crop, and the duration of seed storage.
[1]
Secoisolariciresinol and matairesinol were the first plant lignans identified in foods.
[1]
Typically, lariciresinol and pinoresinol contribute about 75% to the total lignan intake, whereas secoisolariciresinol and matairesinol contribute only about 25%.
[1]
Foods containing lignans:
[1]
[9]
Source
|
Lignan amount
|
Flaxseeds
|
85.5 mg per oz (28.35 g)
|
Sesame seeds
|
11.2 mg per oz
|
Brassica
vegetables
|
0.3-0.8 mg per half
cup
(125 ml)
|
Strawberries
|
0.2 mg per half cup
|
Prevalence and health effects
[
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]
Lignans are the principal source of dietary
phytoestrogens
in typical
Western diets
, even though most research on phytoestrogen-rich diets has focused on
soy
isoflavones
. Lignan's
enterolignan
products
enterodiol
and
enterolactone
have weak
estrogenic
activity, but they may also exert biological effects through non-estrogenic means.
[1]
A 2021 review found that lignans have a positive effect on lipid profiles of patients with
dyslipidemia
related diseases.
[10]
As of 2022 there is limited evidence that dietary intake of lignans is associated with a reduced cancer and cardiovascular disease risk.
[1]
See also
[
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]
References
[
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]
- ^
a
b
c
d
e
f
g
h
i
j
k
"Lignans"
. Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2010
. Retrieved
31 July
2017
.
- ^
From
lign-
(Latin, "wood") +
-an
(chemical suffix).
- ^
Korkina, L; Kostyuk, V; De Luca, C; Pastore, S (2011). "Plant phenylpropanoids as emerging anti-inflammatory agents".
Mini Reviews in Medicinal Chemistry
.
11
(10): 823?35.
doi
:
10.2174/138955711796575489
.
PMID
21762105
.
- ^
Saleem, Muhammad; Kim, Hyoung Ja; Ali, Muhammad Shaiq; Lee, Yong Sup (2005). "An update on bioactive plant lignans".
Natural Product Reports
.
22
(6): 696?716.
doi
:
10.1039/B514045P
.
PMID
16311631
.
- ^
Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis".
Phytochemistry Reviews
.
2
(3): 371?90.
doi
:
10.1023/B:PHYT.0000045487.02836.32
.
S2CID
6276953
.
- ^
Adlercreutz, Herman (2007). "Lignans and Human Health".
Critical Reviews in Clinical Laboratory Sciences
.
44
(5?6): 483?525.
doi
:
10.1080/10408360701612942
.
PMID
17943494
.
S2CID
31753060
.
- ^
Heinonen, S; Nurmi, T; Liukkonen, K; Poutanen, K; Wahala, K; Deyama, T; Nishibe, S; Adlercreutz, H (2001). "In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol".
Journal of Agricultural and Food Chemistry
.
49
(7): 3178?86.
doi
:
10.1021/jf010038a
.
PMID
11453749
.
- ^
a
b
Landete, Jose (2012).
"Plant and mammalian lignans: A review of source, intake, metabolism, intestinal bacteria and health"
.
Food Research International
.
46
(1): 410?24.
doi
:
10.1016/j.foodres.2011.12.023
.
- ^
Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC (2005).
"Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol"
.
British Journal of Nutrition
.
93
(3): 393?402.
doi
:
10.1079/BJN20051371
.
PMID
15877880
.
- ^
Yang, C., Xia, H., Wan, M. (2021).
"Comparisons of the effects of different flaxseed products consumption on lipid profiles, inflammatory cytokines and anthropometric indices in patients with dyslipidemia related diseases: systematic review and a dose?response meta-analysis of randomized controlled trials"
.
Nutrition & Metabolism
.
18
(1): 91.
doi
:
10.1186/s12986-021-00619-3
.
PMC
8504108
.
PMID
34635132
.
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External links
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]