Organosulfur

Organosulfur
Compounds from
Compounds from
Garlic
Garlic
Zainal
 Introduction
 Organosulfur  organic compounds
that contain sulfur.
 Garlic is a particularly rich source of
organosulfur compounds.
 responsible for its flavor and aroma.

 potential health benefits.

 Chemical
Chemical Composition
Composition and
and
Chemistry
Chemistry
 56- 68% water
 26-30% carbohydrates

 Fresh garlic cloves contain about 2-6

mg/g of gamma-glutamyl-S-
allylcysteine (0.2-0.6% fresh weight)
and 6-14 mg/g of alliin (0.6-1.4%
fresh weight).
 Cotains 4 x as much as onions,
brocolli, cauliflower.
 Garliccontains 33 sulfur compounds
 17 amino acids (including essential
aa)
 Mineral (calcium, copper, iron,
potassium, magnesium, selenium,
zinc)
 Vitamins A, B, C, and E
 Garlic cloves are composed of cysteine sulfoxides
and -glutamylcysteines.
 Allylcysteine sulfoxide (alliin) accounts for
approximately 80% of the cysteine sulfoxides in
garlic.
 When raw garlic cloves are crushed, chopped, or
chewed, an enzyme known as alliinase is
released.
 Allicin breaks down in vitro to form a variety of
fat-soluble organosulfur compounds, including
diallyl trisulfide (DATS), diallyl disulfide (DADS),
and diallyl sulfide (DAS), or in the presence of oil
or organic solvents, ajoene and vinyldithiins 
 Thiosulfinates (2-9 mg/g fresh crushed
garlic).
 Crushing garlic does not change its
gamma-glutamylcysteine content.
 Water-soluble organosulfur compounds,
such as S-allylcysteine, are formed from
gamma-glutamylcysteines during long-
term incubation of crushed garlic in
aqueous solutions, as in the manufacture
of aged garlic extracts
 Bioavability and Metabolism
 Allicin and allicin-derived compounds,
including diallylsufides, ajoene, and
vinyldithiins, never detected in human
blood, urine, or stool.
 Allicin and allicin-derived compounds are
rapidly metabolized.
 The concentration of allyl methyl sulfide in
the breath is an indicator of
their bioavailability.
 Consumption of crushed garlic and
equivalent amounts of allicin, DATS,
DADS, ajoene, and allyl methyl sulfide
resulted in similar increases in breath
concentrations of allyl methyl sulfide.
 Allicin and allicin-derived compounds are
metabolized to allyl methyl sulfide, a
volatile compound that can be measured
in exhaled air.
 Gamma-glutamylcysteines are is absorbed
intact and hydrolyzed to S-allylcysteine
and S-1-propenylcysteine.
 Metabolites of these compounds found in
human urine after garlic consumption.
 The consumption of aged garlic extractas
been found to increase plasma S-
allylcysteine concentrations in humans.
Cardiovascular Disease Prevention
 Inhibition of Cholesterol Synthesis
– Garlic and garlic-derived organosulfur
compounds can decrease
the synthesis of cholesterol by hepatocytes
(liver cells)
– Inhibit 3-hydroxy-3-methyl-glutaryl-coenzyme
A reductase (HMG-CoA reductase), a critical
enzyme in the cholesterol biosynthesis
pathway.
– including sterol 4-alpha-methyl oxidase.
 Anti-inflammatory Activity
– Inflammation appears to play an important
role in the pathology of cardiovascular disease.
– inhibit the activity of the inflammatory
enzymes, cyclooxygenase and lipoxygenase, in
vitro 
– decrease the expression of inducible nitric
oxide synthase (iNOS) in inflammatory white
blood cells (macrophages).
 Inhibition of Arterial Smooth Muscle
Proliferation
– The proliferation and migration of normally
quiescent arterial smooth muscle cells are
central features of vascular diseases,
including atherosclerosis and coronary 
restenosis
– organosulfur compounds from garlic may
inhibit the proliferation and migration of
vascular smooth muscle cells. 
 Antioxidant Activity
– organosulfur compounds can stimulate
the synthesis of glutathione, an
important intracellular antioxidant.
 Hydrogen Sulfide-Mediated
Vasodilatory Activity
– Hydrogen sulfide acts as a vasodilator(relaxes
blood vessels) and thus may have
cardioprotective properties
 Biological Activities Related to
Cancer
 Effects on Carcinogen Metabolism
– Inhibition of Phase I biotransformation
enzymes
 DAS and its metabolites have been found to inhibit
CYP (cytochrome P450) 2E1 activity in vitro
 Oral administration of garlic oil and DAS to humans
has also resulted in evidence of decreased CYP2E1
activity.
– of Phase II biotransformation
enzymes.
 increasingthe activity of phase II enzymes,
such as glutathione S-transferase and quinone
reductase, may help prevent cancer by
enhancing the elimination of potential
carcinogens.
– Enhanced cellular glutathione
synthesis
 garlic-derived organosulfur compounds increase
intracellular glutathione concentrations.
– Enhanced cellular glutathione
synthesis
 garlic-derived organosulfur compounds
increase intracellular glutathione
concentrations.
 Glutathione is an important
intracellular antioxidant. 
 Is required for some phase II
biotransformation reactions
– Antimicrobial Activity
 Thiosulfinates, particularly allicin, plays an
important role in the antimicrobial activity of
garlic.
 Allicin-derived compounds, including DATS
and ajoene, also have some antimicrobial
activity in vitro, although generally less than
allicin.
 Effect of cooking
 The enzyme alliinase can be
inactivated by heat.
 microwave cooking of unpeeled,
uncrushed garlic totally destroyed
alliinase enzyme activity
 some scientists recommend that
crushed or chopped garlic be allowed
to “stand” for at least ten minutes
prior to cooking
Powdered (Dehydrated) Garlic
 Powdered or dehydrated garlic is
made from garlic cloves that are
usually sliced and dried at a low
temperature to prevent alliinase
inactivation.
Principal Organosulfur Compounds in Commercial Garlic Preparations
Product Principal Organosulfur Delivers allicin-derived
Compounds compounds?
Fresh garlic cloves Cysteine sulfoxides (Alliin) Yes, when chopped,
Gamma-glutamylcysteines crushed, or chewed raw. 
Minimal, when garlic cloves
are cooked before crushing
or chopping.
Powdered garlic (tablets) Cysteine sulfoxides (Alliin) Varies greatly among
Gamma-glutamylcysteines commercial products.
Enteric-coated tablets that
pass the USP allicin release
test are likely to provide the
most.
Steam distilled garlic oil Diallyl disulfide Yes
(capsules) Diallyl trisulfide
Allyl methyl trisulfide
Garlic oil macerate Vinyldithiins Yes
(capsules) Ajoene
Diallyl trisulfide
Aged garlic extract™ S-Allylcysteine  Minimal
(tablets or capsules) S-Allylmercaptocysteine
S-1-Propenylcysteine
Growing
Growing Conditions
Conditions and
and Suplement
Suplement