1. An
Organic
Chemist’s
Perspec3ve
on
“Paleo”
Mathieu
P.
Lalonde,
Ph.
D.
Ancestral
Health
Symposium
August
6th
2011

2. Credibility:
The
Presenter’s
Currency
Harvard
Department
of
Chemistry
Pfizer
Lecture
Hall
and
Chemical
Biology

3. The
Evolu3onary
Approach:
Observa3on
≠
Causa3on
Our
ancestors
and
modern
hunter-­‐gatherers
consumed
a
diet
mostly
devoid
of
grains,
legumes,
and
dairy.
Our
ancestors
and
modern
hunter-­‐gatherers
were
virtually
free
of
diseases
of
civilizaFon.
Invalid
inference:
Consuming
a
diet
mostly
devoid
of
grains,
legumes,
and
dairy
will
allow
us
to
be
free
of
diseases
of
civilizaFon.
Rader,
A.
W.;
Sloutsky,
V.
M.
Processing
of
Logically
Valid
and
Logically
Invalid
CondiFonal
Inferences
in
Discourse
Comprehension.
Journal
of
Experimental
Psychology:
Learning,
Memory,
and
Cogni=on
2002,
28(1),
59–68.

5. Observa3onal
Epidemiology
as
a
Tool
for
Genera3ng
Hypotheses
Mixture
of
saturated,
polyunsaturated
and
monounsaturated
fats
in
hunter-­‐
gatherer
and
typical
western
diets
The
Paleo
Diet
Update
v3,
#3
-­‐
The
Paleo
Concept
Typical
Hunter-­‐
Western
Diet
gatherer
diet
Ques3ons:
1)
Is
saturated
fat
is
responsible
for
the
poor
health
outcomes
in
the
Western
diet?
2)
What
if
saturated
fat
is
beneficial
but
hunter
gatherers
were
not
consuming
enough
due
to
its
scarcity?
3)
Were
the
levels
of
polyunsaturated
faYy
acids
in
hunter-­‐gatherers
diets
too
high?
Invalid
inference:
EmulaFng
the
dietary
faYy
acid
profile
of
hunter-­‐gatherers
will
lead
to
improved
health.

6. Observa3onal
Epidemiology
as
a
Tool
for
Genera3ng
Hypotheses
Ques3ons:
1)
Are
Americans
consuming
too
many
calories
from
carbohydrate?
2)
Are
Americans
not
consuming
enough
protein?
Invalid
inference:
The
calculated
average
macronutrient
raFo
of
hunter-­‐gatherer
populaFons
is
the
healthiest.
Cordain,
L.;
Friel,
J.
NutriFon
101.
The
Paleo
Diet
for
Athletes:
A
Nutri=onal
Formula
for
Peak
Athle=c
Performance,
1st
ediFon;
Rodale
Books,
2005,
pp.
84.

7. Food:
A
Selec3ve
Agent
in
Evolu3on
“The
immense
biological
variability
among
individuals
has
overpowering
significance.
The
examples
shown
above
lend
support
to
this
thesis.
Much
theore=cal
and
prac=cal
knowledge
can
be
gained
from
study
of
biological
individuality.
Nutri=onal
variability
on
an
interna=onal
level
requires
that
we
be
aware
of
these
intricacies
and
interac=ons.
The
global
approach
necessitates
cau=on
in
implemen=ng
worldwide
nutri=onal
programs
based
on
mean
requirements
derived
in
a
specific
culture.
This
narrow
orienta=on
overlooks
the
importance
of
man’s
nutri=onal
individuality,
a
reflec=on
of
evolu=on.”
Kretchmer,
N.;
Food:
A
SelecFve
Agent
in
EvoluFon.
In
Food,
Nutri=on
and
Evolu=on;
Walcher,
D.
N.;
Kretchmer,
N.,
Eds.;
Masson
Publishing
USA,
Inc.:
New
York,
1981,
pp.
48.

8. Tishkoff,
S.
A.;
Reed,
F.
A.;
Ranciaro,
A.;
Voight,
B.
F.;
BabbiY,
C.
C.;
Silverman,
J.
S.;
Powell,
K.;
Mortensen,
K.
M.;
Hirbo,
J.
B.;
Osman,
M.;
Ibrahim,
M.;
Omar,
S.
A.;
Lema,
G.;
Nyambo,
T.
B.;
Ghori,
J.;
Bumpstead,
S.;
Pritchard,
J.
K.;
Wray,
G.
A.;
Deloukas,
P.
Convergent
AdaptaFon
of
Human
Lactase
Persistence
in
Africa
and
Europe.
Nature
Gene=cs
2006,
39,
31–40.

9. Perry,
G.
H.;
Dominy,N.
J.;
Claw,
K.
G.;
Lee,
A.
S.;
Fiegler,
H.;
Redon,
R.;
Werner,
J.;
Villanea,
F.
A.;
Mountain,
J.
L.;
Misra,
R.;
Carter,
N.
P.;
Lee,
C.;
Stone,
A.
C.
Diet
and
the
EvoluFon
of
Human
Amylase
Gene
Copy
Number
VariaFon.
Nature
Gene=cs
2007,
39(10),
1256–1260.,

10. Food:
A
Selec3ve
Agent
in
Evolu3on
Invalid
inference:
We
evolved
over
millions
of
years
without
consuming
foods
that
became
readily
available
upon
the
advent
of
agriculture,
hence,
we
are
not
adapted
to
these
evoluFonary
novel
foods.

11. Food:
A
Selec3ve
Agent
in
Evolu3on
Is
it
safe
to
assume
that
we
are
not
adapted
to
any
food
that
became
readily
available
and
part
of
the
human
diet
a7er
the
advent
of
agriculture?
Doesn’t
this
suggest
that
a
species
cannot
discover
a
new,
be=er
source
of
food?
Didn’t
our
ancestors
discover
a
new,
be=er
source
of
food
when
they
began
scavenging
bone
marrow
and
brains
and
didn’t
this
impact
their
development?
Does
this
mean
that
all
foods
that
were
available
prior
to
the
advent
of
agriculture
a
re
inherently
healthier?
Invalid
inference:
We
evolved
over
millions
of
years
without
consuming
foods
that
became
readily
available
upon
the
advent
of
agriculture,
hence,
we
are
not
adapted
to
these
evoluFonary
novel
foods.

12. The
Evolu3onary
Approach:
Beware
of
the
Selec3on
Bias
Remember
that,
at
the
end
of
the
day,
all
hypotheses
must
be
tested
before
they
can
be
shown
to
be
valid
or
invalid.
Even
if
some
may
appear
less
valid
than
others
when
considering
testability,
simplicity,
scope,
fruiVulness,
and
conserva3sm.
Approaching
a
problem
by
thinking
the
solu3on
is
at
hand
because
the
hypothesis
relies
on
evolu3on
will
only
lead
to
poor
science.

13. The
Periodic
Table
of
the
Elements

14. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Valence
Electrons,
Bonding
&
Geometry
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Valence Electrons H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
LF
C N O
alonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H
H H
Copyright
Structure P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Kekulé Mathieu
H C H H N H H O H F F
H H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
109.5° 104.5°
Molecular Geometry H H C H N H O F F
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H H
H H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
Fluorine
P.
Lalonde
107.3°
Hydrogen Methane Ammonia Water
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Linear Linear
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Tetrahedral
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

15. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Hydrocarbons
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH
H opyright
Mathieu
P.
Halonde
Copyright
MH H P.
Lalonde
H L H H athieu
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
H.
Lalonde
H
H C H C C
P
C H C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
LC
H H C H C alonde
Copyright
Mathieu
P.
Lalonde
H C C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H
H H HH H H HH H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Methane Ethane Propane Butane
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
LH H H CH H H HMH H H P.
Lalonde
H HH HH H H H H H H H H H alonde
opyright
athieu
Copyright
MC C C PCLalonde
Copyright
C athieu
P.
Lalonde
Copyright
Mathieu
P.
Halonde
H
C athieu
.
H H
C
C
C MC
C
C
C
C
C
C
C
C
C
C
C
C
C
L
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H HH H H HH HH HH HH HH HH HH HH H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
POctadecaneopyright
Mathieu
P.
Lalonde
Pentane .
Lalonde
C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
The
bond
angles
in
the
chain
are
drawn
as
120
°
for
convenience
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

16. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Double
Bond
Geometry
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H H
Copyright
Mathieu
P.
LCC
C
alonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
C C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
C H C C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
trans: hydrogen atoms on opposite cis: hydrogen atoms on the same
sides of a disubstituted double bond. side of a disubstituted double bond.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH H H H H athieu
P.
Oalonde
CH H H H Mathieu
P.
Lalonde
O H H H H H H H H H H opyright
M L H H H opyright
Copyright
C C C C C .
Lalonde
C opyright
Mathieu
P.
C alonde
C opyright
Mathieu
P.
Lalonde
HO
C
C
C Mathieu
P C
C
C
C CC
C
C
C
C
H
HO L C
C
C C C
C
C
C H
C H HH HH H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
LH H H HCH H H H Mathieu
P.
Lalonde
H HH HH HH H H H HH HH HH H alonde
opyright
C C C C H
H C C C C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
H athieu
P.
Lalonde
M
H HH HH HH H
Copyright
Mathieu
Acidalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Elaidic
P.
L (18:1n-9) Oleic Acid (18:1n-9)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
trans-Octadec-9-enoic Acid
omega
carbon cis-Octadec-9-enoic Acid
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

17. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Bond-­‐Line
Formulas
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
PH Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O H H H H H H H
.
H H H H H H H H O
C C C C C C C C C H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO C C C C C C C C C
HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Acid (18:0) P.
Lalonde
H H H H H H H H H H H H H H H H H H
Stearic Mathieu
Stearic Acid (18:0)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O H H H H H H H
O
C C C C C H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO C C C C C H H H H H H
HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H H H H H H H C
H C
C
C
C
C
C
C
H
CH3
H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
M(18:1n-9) P.
Lalonde
H H H H H H H H
Oleic Acid athieu
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Oleic Acid (18:1n-9)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
H .
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H
H P H H
H
H C H C C H C H
Copyright
Mathieu
H .
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O C
HC
C H C PC CH C
H C
C O
Copyright
Mathieu
HH LH C C C Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO
C
C
C
H C
C
P.
Halonde
H C H HO Me
H H H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H H H H H Docosahexaenoic Acid (22:6n-3)
Docosahexaenoic Acid (22:6n-3)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mre
implied
and
omi]ed.
Hydrogen
atoms
a athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Ldrawn
bCopyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Carbon
atoms
are
not
alonde
ut
implied
to
be
located
at
the
end
and
junc3on
of
every
line.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Electron
pairs
can
be
drawn
or
omi]ed.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

18. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Stereochemistry
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Dichlorofluoromethane Bromochlorofluoromethane
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
mirror mirror
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
MHathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H H H
Copyright
MCathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
C C C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Br athieu
P.
Lalonde
F Cl Cl F F Br M F
Cl Cl Cl Cl
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
MHathieu
P.
Lalonde
Hopyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
C H H
Copyright
MCathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
C C C
Copyright
Mathieu
F Cl P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
F athieu
P.
Lalonde
F Cl F Br M Cl
Cl Cl Cl Br
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lmirror images (S) (R)
superimposable alonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
mirror images Lalonde
non-superimposable Mathieu
P.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Enantiomers

19. Basic
Organic
Chemistry
Knowledge
is
Important
hYp://www.greenmedinfo.com/blog/franken-­‐thyroxine-­‐making-­‐your-­‐thyroid-­‐condiFon-­‐worse

20. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Structure
and
Func3on:
Thyroxine
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
mirror
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
I O O I
HO I I OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
NH2 NH2
I O O I
Copyright
Mathieu
P.
LIalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
I
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
L-Thyroxine, T4
Levothyroxine
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(thyroid hormone)
NaOH 180 °
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
I O I O
HO I HO I
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
LOH
O alonde
Na [H2O]x
Copyright
Mathieu
P.
Lalonde
2Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
NH NH2
I O I O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
I I
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Levothyroxinealonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Mathieu
P.
L sodium Dextrothyroxine
(thyroid hormone) (cardiac side-effects)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

21. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Structure
and
Func3on:
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Elaidic
vs
Oleic
Acid
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
1Mathieu
P.
Lalonde
O •Increases CETP activity
Copyright
Mathieu
P.
Lalonde
Copyright
MCH3 •Induces dyslipidemia2,3
athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO
•Impairs endothelium function3
Copyright
Mathieu
P.
Acid (18:1n-9) Elaidic
Lalonde
Copyright
Mathieu
P.
Lalonde
insulin sensitivity.4•Decreases
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Diastereomers: stereoisomers that are not mirror images
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
•Improves glycemic tolerace through increased
HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
glucagon-likeMathieu
P.
Lalonde
secretion of Copyright
peptide-15
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH3 •Reduces blood pressure.6
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Oleic Acid (18:1n-9)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
1)
Abbey,
M.;
Nestel,
P.
J.
Plasma
Cholesteryl
Ester
Transfer
Protein
AcFvity
is
Increased
when
Trans-­‐Elaidic
Acid
is
SubsFtuted
for
Cis-­‐Oleic
Acid
in
the
Diet.
Atherosclerosis
1994,
106,
99–107.
2)
Bendsen,
N.
T.;
Chabanova,
E.;
Thomsen,
H.
S.;
Larsen,
T.
M.;
Newman,
J.
W.;
Stender,
S.;
Dyerberg,
J.;
Haugaard,
S.
B.;
Astrup,
A.
Effect
of
Trans
FaYy
Copyright
Mathieu
P.
LL.;
Katan,
M.
B.
Replacement
of
Dietary
Saturated
P.
LAcids
by
Trans
Copyright
Mathieu
P.
Lalonde
alonde
Copyright
Mathieu
FaYy
alonde
FaYy
Acids
Lowers
Serum
HDL
Cholesterol
and
Impairs
Acid
Intake
on
Abdominal
and
Liver
Fat
DeposiFon
and
Blood
Lipids:
A
Randomized
Trial
in
Overweight
Postmenopausal
Women.
Nutri=on
and
Diabetes
2011,
doi:10.1038/
nutd.2010.4.
3)
de
Roos,
N.
M.;
Bots,
M.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Endothelial
FuncFon
in
Healthy
Men
and
Women.
Arterioscler.
Thromb.
Vasc.
Biol.
2001,
21,
1233–1237.
4)
ChrisFansen,
E.;
Schnider,
S.;
Palmvig,
B.;
Tauber-­‐Lassen,
E.;
Pederson,
O.
Intake
of
a
Diet
High
in
trans
Monounsaturated
FaYy
Acids
or
Saturated
FaYy
Acids.
Effects
on
Postprandial
Insulinemia
and
Glycemia
in
Obese
PaFents
with
NIDDM.
Diabetes
Care
1athieu
P Lalonde
Copyright
Mathieu
P Lalonde
Copyright
Mathieu
P Lalonde
Copyright
M 997,
20,
881–887.
.
.
.

22. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Structure
and
Func3on:
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Glucose
vs
Fructose
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
HO
OH
HO
OH
O
Copyright
Mathieu
P.
OH
Lalonde
OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH HO OH
HO
OH
O O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO HO HO OH HO
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH
!-D-(+)-Glucopyranose "-D-(+)-Glucopyranose
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
PD-Fructofuranose
(36.4% in solution) (63.6% in solution) .
(32% in solution)
Lalonde
Copyright
Mathieu
P.
Lalonde
D-Fructopyranose
(68% in solution)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH O OH OH OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO HO
H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH OH O
Copyright
Mathieu
P.
LO
C6H12 6
alonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
C6H12O6
Copyright
Mathieu
P.
Hexose Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Aldose, Lalonde
Ketose, Hexose
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
D-(+)-Glucose "-D-(–)-Fructose
(0.003% in solution)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

23. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Structure
and
Func3on:
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Adrenaline
Biosynthesis
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
Phenylalanine Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
P.
Lalonde
O
Tyrosine
O
hydroxylase hydroxylase HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P2.
Lalonde
NH2
HO
NH2
HO
NH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Phenylalanine
(amino acid)
Tyrosine
(amino acid)
L-DOPA
(precursor to catecholamine neurotransmitters)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
DOPA
decarboxylase
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
OH athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
M H OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
MHO
HO N
Phenylethanolamine
N-methyltransferase HO NH2
Dopamine
!-hydroxylase
athieu
P.
Lalonde
NH2
CH3
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
MHO
HO HO
athieu
P.
Lalonde
(stress hormone, Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
neurotransmitter)
Epinephrine (a.k.a. adrenaline) Norepinephrine Dopamine
(stress hormone, neurotransmitter) (neurotransmitter, neurohormone)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

24. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Structure
and
Func3on:
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Biologically
Ac3ve
Phenethylamines
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH
OH
opyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH H OH H
Copyright
Mathieu
P.
Lalonde
CN
NH2
opyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
N N
CH3 CH3
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH3 CH3
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Phenethylamine Albuterol (+)-Pseudoephedrine (–)-Pseudoephedrine
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(psychostimulant) (bronchodilator) (Sudafed, decongestant) (bronchodilator)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
OH Lalonde
Copyright
Mathieu
P.
Lalonde
O
P.
H CH3O NH2
H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
NH2
N N
H2N
Copyright
3 athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH M
CH3
CH3O
CH3 CH3
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO CH3O
Copyright
Mathieu
(psychostimulant) opyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(+)-Amphetamine
(psychostimulant)
P.
Lalonde
C
(+)-Methamphetamine Labetalol
(antihypertensive drug)
Mescaline
(psychoactive drug)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
possible stereoisomers
mixture of all 4 P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde

25. Natural
Products

26. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Plant-­‐Derived
Natural
Products
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Structural: Biologically Active Natural Compounds
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
CH3
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
N opyright
Mathieu
P.
Lalonde
HO
OH N
C O
Copyright
HOathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
M O
O N
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
N CH3
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O opyright
Mathieu
P.
Lalonde
HO O H3C C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH Caffeine
n
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
(psychoactive stimulant) Mathieu
P.
Lalonde
Cellulose
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
L3alonde
Copyright
Mathieu
P.
Lalonde
H C H3C
OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
3Lalonde
Copyright
Mathieu
P.
Lalonde
H H C
O N O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O H O
OH O O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
CH3
Defense: Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Paclitaxel O O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(mitotic inhibitor used in cancer therapy)
HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H CH3
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
N
H3CO CH
Copyright
Mathieu
P.
Lalonde
Copyright
3 athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
M
O
Copyright
Mathieu
P.
LCapsaicinopyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
alonde
C

27. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Plant-­‐Derived
An3nutri3onal
Factors
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
enzyme inhibitors
Tannins Digestive
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Proanthocyanidins R1 O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(forage legumes) OH HO OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO O
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO Copyright
Mathieu
P.
Lalonde
R 2
OH
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
OH OH
OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
Chlorogenic acid
HO O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(sunflower seeds)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
Copyright
Mathieu
1=R2alonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Propelargonidin: R P.
L =H
Procyanidin: R1=OH, R2=H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Prodelphinidin: R1=R2=OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Toxic Amino Acids
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
NH2 O
Copyright
O athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H2N N M OH
An3nutrients
or
an3nutri3onal
factors:
Substances
that
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Canavanine NH2
(leguminous plants) can
reduce
absorpFon
and
uFlizaFon
of
nutrients,
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Cmay
produce
undesirable
efficiency
of
digesFon,
and
opyright
Mathieu
P.
Lalonde
O O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
not
a
substance
possesses
HO S S OH health
effects.
Whether
or
Copyright
Mathieu
P.
Lalonde
NH2 NH anFnutriFve
properFes
depends
on
the
digesFve
process
Copyright
Djenkolic acid Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Mathieu
P.
2
of
the
animal
that
ingested
the
substance.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
(djenkol beans)

28. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Plant-­‐Derived
An3nutri3onal
Factors
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Phytates N Cyanogenic Glycosides
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OO OH
C
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
P
O
O
P O
O
O O
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
P
O O
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O P
HO OH
OH OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
N .
C alonde
O O
O
O
HO PL
P O O Linamarin
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
beans, flax) Copyright
Mathieu
P.
H alonde
O
O
O P
(cassava, lima Lalonde
O
H L
OO O O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Phytic Acid
OH
HO OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
OH Lalonde
(seeds)
Amygdalin
P.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mapricot, black cherry)
(bitter almond, athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH FODMAPs
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO
Oxalate O HO
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
O .
H alonde
Copyright
Mathieu
P.
Lalonde
H P LO OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O HO O
OH OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
O
OH
HO OH
O
HO OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
O OH Lalonde
Copyright
Mathieu
P.
Lalonde
OH
OH OH
Raffinose
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
asparagus Mathieu
P.
Lalonde
Oxalate
(beans, cabbage, brussels sprouts, broccoli, Copyright
Xylitol
(occurs in many plants) (berries, oats, mushrooms)
Copyright
Mathieu
P.
Lalonde
Copyright
other vegetables Lalonde
Copyright
Mathieu
P.
Lalonde
as well as
Mathieu
P.
and whole grains)
Copyright
Mathieu
iP.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
&
pepFdomorphins,
Other
an3nutrients
nclude:
Saponins
&
glycoalkaloids,
prolamine
proteins
Mathieu
P.
Lalonde
Copyright
Mhytoestrogens.
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
goitrogens,
p athieu
P.
Lalonde

29. Concentra3on
of
an3nutrients
in
maize
Concentra3on
of
an3nutrients
in
rice
Edeogu,
C.
O.;
Ekuma,
C.
E.
AnFnutrient
Level
in
Staple
Food
Crops
in
Ebonyi-­‐Nigeria.
Research
Journal
of
Environmental
Sciences
2007,
1(6),
302–309.

30. Concentra3on
of
an3nutrients
in
yams
Concentra3on
of
an3nutrients
in
cassava
Concentra3on
of
an3nutrients
in
cowpea
Concentra3on
of
an3nutrients
in
yambean
Edeogu,
C.
O.;
Ekuma,
C.
E.
AnFnutrient
Level
in
Staple
Food
Crops
in
Ebonyi-­‐Nigeria.
Research
Journal
of
Environmental
Sciences
2007,
1(6),
302–309.

31. Mean
concentra3on
of
chymotrypsin
inhibitors
(IU)
in
staple
foods
Edeogu,
C.
O.;
Ekuma,
C.
E.
AnFnutrient
Level
in
Staple
Food
Crops
in
Ebonyi-­‐Nigeria.
Research
Journal
of
Environmental
Sciences
2007,
1(6),
302–309.

32. Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Saponins
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Me OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Me Me Me
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
MH Me P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO
athieu
Copyright
Mathieu
P.
oralonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Me Me
H L
3-Epikatonic acid
HO OH
Copyright
MGuar sapogenin (aglycone)
athieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
triterpene (C30)
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
OH Lalonde
Copyright
Mathieu
P.
Lalonde
O
O
PO
.
OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Me O H O OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H
HO OH
H
Copyright
Mathieu
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
O P.
OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO
Me Me Me
O
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
H Me
Copyright
Mathieu
P.
Halonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Me OH HO
HO O O
LO H
Me Me
Copyright
Mathieu
P.
Lalonde
CGuar meal saponin
O
H opyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
H Oathieu
P.
Halonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
HO M O L
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH OH
O
OH
Common saccharides: Glucose, galactose,
glucuronic acid, xylose, rhamnose or methylpentose
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Me OH
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
OH
Copyright
areathieu
P.
ofalonde
oropyright
Mathieu
P.
Lalonde
ability to form Mathieu
P.
Lalonde
Saponins M glycosides L steroids C triterpenes that were named for their Copyright
stable, soap-like foams
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
Copyright
Mathieu
P.
Lalonde
in aqueous solutions.