NUTRACEUTICAL

AND
FOOD
CHEMISTRY

2020-2021
 Sofia Gulia
presents

LIGNANS &

CURCUMIN AND CURCUMINOIDS

INTRODUCTION

Therapeutically,
PHYTOESTROGENS are
divided into three classes:
• isoflavones
• cumestans
• lignans
INTRODUCTION- Phytoestrogens

The main activities are similar to the estrogen ones, reducing problems
deriving from a deficiency or an excess of them.

Other effects seem to be reduced: the side effects of menopause, blood

cholesterol levels, the risk of cardiovascular events, the risk of fractures in
the presence of osteoporosis, the incidence of so-called female tumors.
LIGNANS
Lignans are substances of natural origin that
help us maintain a healthy heart and strengthen
the immune system. Contained in the woody
tissues of more than 55 plant species, in
cereals, rye, and some vegetables (carrots,
broccoli, cabbage, strawberries and berries).

The richest source is represented by flax seeds,

which mainly contain secoisolariciresinol, but
in good quantities also lariciresinol, pinoresinol
and matairesinol. They are also found in
sesame seeds.

FLAX SEEDS
They are also present in other foods, but in lower
concentrations. Examples include:

• Drinks
• Fruit
• Vegetables
• Lentils and beans.

Their presence in whole grains and, to a

lesser extent, in red wine and fruit means
that, at least in the population following a
Mediterranean-type diet, they represent the
main source of phytoestrogens.
 CHEMICAL STRUCTURE
Their chemical structure consists of two units of phenylpropane linked through a carbon- carbon bond also known as β-β’ bond.
Less frequently, bonds 3-3 ', 8-O-4', or 8-3 'are observed. In these cases the dimers are called NEOLIGNANS.
On the basis of the carbonaceous skeleton they can be divided into 8 subgroups:
• furans
• furofurans
• dibenzylbutanes
• dibenzylbutyrolactones
• dibenzocyclooctadiadienes
• dibenzylbutyrolactol
• Aryltraline
• arylnaphatlene.

In nature they are not present in free form but linked to other molecules, generally glycosylates. Among the most common are
secoisolariciresinol (the most abundant) but in good quantities also are lariciresinol, pinoresinol, matairesinol and 7-
hydroxymatairesinol.
 CHEMICAL
SYNTHESIS

• The first three reactions reduce the

carboxylic groups of
hydroxycinnamates to alcoholic
groups.

• The next step: dimerization

IMPORTANCE FOR HUMAN HEALTH

Their importance for human health derives to a large extent from the
metabolization they that undergo in the colon by the intestinal microbiota,
which operates deglycosilations.
The product of the reactions are the so-called mammalian lignans or
enterolignans.
 Podofillotossina

Lignans have also triggered pharmacological interest.

Examples include:

LIGNANS: • Podophyllotoxin- obtained from plants of the genus

PHARMACOLOGICAL Podophyllum (Berberidaceae family), a mitotic toxin
INTEREST whose derivatives have been used in chemotherapy;
• Arctigenin and tracheologine- obtained from tropical
climbing plants, which have antiviral properties and
have been tested in the search for a drug for the
treatment of AIDS. The results are promising, but much
work is still needed in this area of medicine.

Arctigenina
 PHARMACOLOGICAL INTEREST

Lignans are therefore recognized for their ability to prevent and COMBAT
CERTAIN FORMS OF CANCER and in particular prostate, colon and skin
cancer.

Hower is important to remember that when we talk about cancer the prevention
is implemented, not only by following a diet rich in lignans, isoflavones and
antioxidants, but also by adopting a careful lifestyle.
METABOLISM AND It has been hypothesized that a good part of them is
absorbed at the level of the mammary adipose tissue. For
BIOAVAILABILITY this reason they are excellent candidates for the prevention
of breast cancer. In addition, the remaining unabsorbed
part remains in the intestine, where it exerts a preventive
Breast and colorectal cancer prevention action against colorectal cancer (CRC).
 Sesamine, present in sesame oil, induced growth
arrest in MCF-7 breast cancer cells by blocking the
correct progression of the cell cycle in phase G1. In
light of the results obtained, in this way lignans
SESAMINE inhibit the development of various types of cancer

SESAMINE
 SCIENTIFIC STUDIES

In one study it was noted an absorption of about 50% of pinoresinol by JIMT1

breast cancer cells between 2 and 24 h after intake, while the absorption of
acetoxypinoresinol was already about 40% after 1 h from hiring. On the other
hand, in a research it was shown that Caco-2 colorectal cancer cells, after 4 hours
of exposure to a concentration of 40 μM of pinoresinol, had absorbed only 2%, of
which 75% in conjugate form.
 SCIENTIFIC STUDIES

The study showed that pinoresinol is internalized by means of a concentration

gradient. Since the transporter for pinoresinol is not specific, lignans could also be
absorbed by other cell types where it could exert other biological effects.
Interactions between lignans and some foods that could affect their absorption,
plasma half-life and elimination cannot be ruled out. However, it has not yet been
clarified how lignans are internalized within target cells
SCIENTIFIC STUDIES- Nettle

This study sheds light on the composition and biosynthesis of lignan in nettle, providing a
good basis for further functional analysis of DIR and PLR and, ultimately, for engineering
lignan metabolism in plant and cell cultures.
NETTLE

We are talking about nettle in relation to a large group of

lignans to which the beneficial effect of the plant is
attributed in numerous ailments.
 PINORESINOL-LARICIRESINOL REDUCTASE (PLR)
DIR and PLR
HO

O
H3C

Lignans show considerable diversity in their OH

basic chemical structure due to the different O

degree of oxidation and substitution of their

aromatic fractions. This heterogeneity is mainly
determined through reactions mediated by CH3
executive proteins (DIR) and pinoresinol- O

lariciresinol reductase (PLR) OH

Thus, 14 genes encoding leading proteins (UdDIR s) and 3 pinoresinol-lariciresinol
reductase (UdPLR s) genes were identified in nettle.
BLASTN and BLASTX analyzes against the transcriptome of nettle leaves were also performed
at the oneKP database to examine and verify the results obtained. Some sequences have been
reconstructed to obtain the full length.
In a total of 14 DIRs identified, 8 contains a reading frame between 178 and 203 amino acids
 AMINO ACIDS SEQUENCES

Alignment of the amino acid sequence of DIR from U.

dioica and selected sequences of A. thaliana (At). Five
conserved motifs (I - V) previously reported in have been
identified in the amino acid sequences of the UdDIRs and
are underlined in red.
PHILOGENETIC TREE

To further understand the

evolutionary relationships of
DIRs between U. dioica and other
plant species, an unrooted
phylogenetic tree was constructed
using 218 DIR protein sequences
from different plant species.
 CURCUMIN
AND
CURCUMINOIDS
 HISTORY

"There is also a vegetable, which has all the properties

of real saffron, as well as color, but which is not real
saffron. (Curcuma) is held in high regard, and is an
ingredient in all their dishes ".

- Marco Polo
 CURCUMINOIDS

Curcuminoids are the main bioactive

constituents of turmeric.
Turmeric, in turn, is obtained from the
tuberized rhizomes of the Curcuma longa L.
plant (Zingiberacee family)

After being properly washed, boiled and

dried, the rhizomes are pounded with
specific tools and reduced to the thin
yellow powder that we all know. The
curcuminoid content of turmeric is around
3-5%.
Curcuminoids give the spice the classic yellow-
orange color, which allows it to be used as a food
additive (reported as E100). They are also
responsible for its health effects.

They consist of a mixture of elements such as:

• Curcumin 75%
• dimethoxy-curcumin 16%
• bis-dimethoxy-curcumin 8%
 EXTRACTION OF CURCUMINOIDS

Contrary to what one might think, the extraction of curcuminoids from turmeric is not
simple and requires adequate timing and technologies. Specifically, the synthesis of
curcumin, that is strongly influenced by other factors.
 PROPERTY OF CURCUMINOIDS
Together with the essential oil and its active ingredients, curcuminoids characterize the biological properties of Turmeric.

At the moment, different clinical trials and numerous experimental studies attribute to curcuminoids, in
particular curcumin, properties:

• Hepatoprotective
• Antioxidants
• Anti-inflammatory
• Gastroprotective
• Cardioprotective
• Neurotrophic
• Antidepressants
• Hypoglycemic drugs CURCUMINOIDE- Chemycal structure
• Anticancer
• Antiaging
 ANTI-INFLAMMATORY PROPERTIES

Curcuminoids inhibit the production of

prostaglandins. Important studies have also
characterized the excellent skin permeability
of these active ingredients.
ANTI-INFLAMMATORY
PROPERTIES
PSORIASIS

In one clinical study, five out

of ten patients were reported
to have 90% resolution of
psoriasis after 2-6 weeks of
treatment with curcumin gel,
while the rest of the patients
had 50-85% improvement
after 3-8. weeks of
treatment.
CHOLERETIC AND
COLAGOGUE PROPERTIES

Numerous studies, both

experimental and clinical,
have shown how the intake of
Curcuminoids can significantly
influence bile secretion.
 The intake of Curcumin and Curcuminoids has proved
effective, both in an experimental and clinical setting, in
significantly reducing plasma concentrations of cholesterol
and triglycerides.

In two clinical studies involving over 200 people with type

IPOLIPIDEMIC 2 diabetes or metabolic syndrome, a combination of 1,000
mg / day of curcumin and 10 mg / day of piperine lowered
PROPERTIES total cholesterol and LDL and VLDL (the "bad" type ),
while it increased HDL cholesterol (the "good" type).

CHOLESTEROL
 ANTI- Numerous studies indicate that curcumin can reduce the growth
of cancer cells in the laboratory and inhibit the growth of tumors
CANCER in animals.

PROPERTIES
ANTIDEPRESSIVE AND NEUROTROPHIC PROPERTIES

A recent review of clinical studies suggests that curcumin in combination with standard
therapy reduces symptoms of depression.
Curcumin has been shown to cross the blood-brain barrier delaying or
even reversing neurodegenerative diseases and preventing age-related
cognitive decline
ANTIDIABETIC PROPERTIES

Curcuminoids can improve glucose metabolism and

reduce the effects of diabetes on the body.
In a clinical study of 100 people with type 2 diabetes, a
combination of 500 mg / day of curcumin and 5 mg /
day of piperine, taken for 3 months, lowered blood
sugar.
 CURCUMIN
Curcumin is the main biologically active component of Turmeric.

The chemical formula of Curcumin is C21H20O6, it is also known as diferuloylmethane

STANDARDIZED EXTRACT CURCUMIN 95%

The standardized extract contains at least 95% Curcuminoids, Curcumin,

Demethoxysurcumin and Bisdemetossicurcumin, the full range of
antioxidants extracted from Turmeric. It is the exact percentage used in
numerous clinical studies.
Unlike many other antioxidants, curcuminoids are able to both prevent the
formation of free radicals and neutralize existing free radicals, and are
considered effective bioprotectors due to this dual activity.
500 MILLIGRAM
CAPSULES

The recommended dose is one to four

capsules per day, to be taken with meals,
to minimize any inflammatory processes
during ingestion and digestion.
 CROHN'S DISEASE

Curcumin blocks both the production and the action of TNF.

ALZHEIMER
Research has found that curcumin can help the immune system "clear"
the brain of beta amyloid, the main constituent of the plaques found in
Alzheimer's disease. Since Alzheimer's is caused in part by amyloid-
induced inflammation, Curcumin has been shown to be effective
against Alzheimer's disease.
UNDESIRABLE EFFECTS AND
CONTRAINDICATIONS

Several studies have shown that Curcumin is not toxic to humans, up to 8000
mg / day (16 capsules per day). The FDA classifies Turmeric as a GRAS
(General Recognition And Safety) substance, or "Generally Recognized
Safe".
 BIBLIOGRAPHY
• Kyung-A Hwang & Kyung-Chul Choi, “Anticarcinogenic Effects of Dietary Phytoestrogens and Their
Chemopreventive Mechanisms”17 Feb 2014

• Dr. Nicola Tazzini, «Lignani: cosa sono, struttura, sintesi, metabolismo, dove si trovano» 6 Oct 2015,
Tuscany Diet.
https://www.tuscany-diet.net/2015/10/06/lignani-definizione-struttura-biosintesi-metabolismo-alimenti/

• Xu X, Guignard C, Renaut J, et al. Approfondimenti sulla composizione e biosintesi di Lignan nell'ortica

(Urtica dioica L.)