2015.02.18.
Carbohydrates
(saccharide
saccharides)
s)
Carbohydrates
(saccharides)
1
2
Carbohydrates
(saccharides)
Monosaccharides
• A carbohydrate is an organic compound that
consists only of carbon, hydrogen,
hydrogen, and oxygen
oxygen,
usually with a hydrogen : oxygen atom ratio of 2:1 (as in water);
consist of :
in other words, with the empirical formula Cm(H2O)n
• The term is most common in biochemistry,
where it is a synonym of saccharide.
3 to 6 carbon atoms,
typically a carbonyl group (aldehyde
aldehyde or ketone
ketone)
several hydroxyl groups
• The carbohydrates are divided into 3 chemical
groups: monosaccharides
monosaccharides,,
oligosaccharides
oligo
saccharides and
polysaccharides
3
Aldoses
Ketoses
Ketoses are monosaccharides
Aldoses are monosaccharides
• with an aldehyde group
• with many hydroxyl (─ OH) groups
triose (3 C atoms)
tetrose (4 C atoms)
pentose (5 C atoms)
hexose (6 C atoms)
4
O
║
C─H aldose
│
H─ C─OH
│
H─ C─OH
│
CH2OH
• with a ketone group
• with many hydroxyl (─ OH) groups
Erythose, an aldotetrose
5
triose (3 C atoms)
tetrose (4 C atoms)
pentose (5 C atoms)
hexose (6 C atoms)
CH2OH
│
C=O
C=
O
ketose
│
H─ C─OH
│
H─ C─OH
│
H─C─OH
│
CH2OH
Fructose, a ketohexose
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Photosynthesis
Carbohydrates
• are produced by photosynthesis in plants
• such as glucose are synthesized in plants from CO 2, H2O,
and energy from the sun
• are oxidized in living cells (respiration) to produce CO 2,
H2O, and energy
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8
citrate cycle
schematically
the tricarboxylic acid cycle (TCA cycle), the
Krebs cycle,
or the Szent-Györgyi–Krebs cycle
The reactions in which NAD + is
converted in NADH and GDP to
GTP and FAD to FADH
FADH2
2 means
that energy has been released and
that this energy is stored in these
formed compounds. This energy
can be used for a lot of purposes.
9
Categories of Carbohydrates
Monosaccharides and disaccharides are also known as simple sugars, or simple
carbohydrates, and polysaccharides are also known as complex carbohydrates.
• Simple Carbohydrates: Monosaccharides and Disaccharides
The term "saccharide" means sugar, so monosaccharide literally means one (i.e. "mono")
sugar (i.e. "saccharide") molecule. Monosaccharide sugar molecules are also referred to
as simple sugars or simple carbohydrates. Glucose, also known as blood sugar, and
fructose, also known as fruit sugar, are examples of monosaccharide sugar molecules.
fructose
A disaccharide is composed of two monosaccharides (i.e. two sugar molecules). Maltose
Maltose,
for example, is a disaccharide composed of two glucose monosaccharides, and sucrose
(or table sugar) is a disaccharide composed of a glucose monosaccharide and a fructose
monosaccharide.
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Monosaccharides
Glucose
Fructose
fruits, mel
fruits, mel
• Complex Carbohydrates: Polysaccharides
Polysaccharides, also known as complex carbohydrates, are made up of many ("poly"
means many) glucose molecules. Examples of polysaccharides include starch,
glycogen, and cellulose, all of which are composed of just glucose molecules but differ
in the manner in which the glucose molecules are linked together.
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Galactose
milk sugar
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Disaccharides
Beta vulgaris,
Saccharum officinarum,
fruits
maple syrup
Saccharose
two glucoses
milk, dairy products,
Lactose - milk sugar,
(glucose and galactose)
open aldehyde structure for glucose into a cyclic hemiacetal,
called a glucopyranose
milk products
Maltose
seed-germ
(glucose and fructose )
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/carbhyd.htm
14
Polisaccharides
Amilose
potato, cereals
(starch, linear
glucose polymer)
Amilopectin
potato, cereals
(starch, branched
glucose polymer)
Glikogen
liver, meat (muscle)
(glycogen, branched
glucose polymer)
Cellobiose : 4-O-β-D-Glucopyranosyl-D-glucose
Maltose : 4-O-α-D-Glucopyranosyl-D-glucose
Gentiobiose : 6-O-β-D-Glucopyranosyl-D-glucose
Trehalose : α-D-Glucopyranosyl-α-D-glucopyranoside
Inulin
artichoke, sweet potato
(fructose polymer)
16
For example
•
•
•
•
starch consists of two fractions:
About 20% is a water soluble material called amylose. Molecules of amylose are linear chains of
several thousand glucose units joined by alpha C-1 to C-4 glycoside bonds.
Amylose solutions are actually dispersions of hydrated helical micelles.
The majority of the starch is a much higher molecular weight substance, consisting of nearly a
million glucose units, and called amylopectin.
Molecules of amylopectin are branched networks built from C-1 to C-4 and C-1 to C-6 glycoside
links, and are essentially water insoluble.
blood sugar is the monosaccharide glucose,
table sugar is the disaccharide sucrose, and
milk sugar is the disaccharide lactose (see illustration)
Carbohydrates perform numerous roles in living organisms:
Polysaccharides serve for the storage of energy (e.g., starch and
glycogen), and as structural components (e.g., cellulose in plants
and chitin in arthropods). The 5-carbon monosaccharide ribose is an
important component of coenzymes (e.g., ATP, FAD, and NAD) and
the backbone of the genetic molecule known as RNA. The related
deoxyribose is a component of DNA. Saccharides and their
derivatives include many other important biomolecules that play key
roles in the immune system, fertilization, preventing pathogenesis,
blood clotting, and development
• In food science and in many informal contexts, the term
carbohydrate often means any food that is particularly rich in the
complex carbohydrate starch (such as cereals, bread, and pasta) or
simple carbohydrates, such as sugar (found in candy, jams, and
desserts)
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2015.02.18.
•
Complex oligosaccharides are common components of numerous biologically
important macromolecules. In many of these systems aminosaccharides,
deoxysaccharides and C9 glyconic acids are found linked to more common sugar units
•
Cyclodextrins:
An interesting class of non-reducing oligosaccharides composed of glucopyranose
rings joined 1-4 by alpha-glycosidic bonds are called cyclodextrins.
MONOSACCHARIDES
in crude drugs
- the interior of the cyclodextrin ring is relatively hydrophobic,
these remarkable compounds are able to encapsulate small nonpolar molecules
- they have been used as catalysts and aqueous transport agents
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Honey,, mel
Honey
Apis mellifica L. - the nectar of flowers collected by honey bees ( Apidae),
in the bowels of processed liquid














a sweet food made by bees using nectar from flowers
mixture of sugars and other compounds
carbohydrates: is mainly fructose (38.5%) and glucose (31.0%)
water (10 -20%)
dextrin
essential oils
acids (tartaric acid, malic acid, formic acid)
wax
pigment
vitamin B2
acetylcholin
aminoacids
enzyms (invertase, amylase)
mineralelements
Apitherapy::
Apitherapy
uses the bee products like:
honey,
pollen,
propolis,
royal jelly, and
bee venom
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Propolis
• is a resinous mixture that honey bees
•
•
•
•
collect from tree buds, sap flows, or other botanical sources
it is used as a sealant for unwanted open spaces in the hive
propolis is used for small gaps while larger spaces are usually filled with beeswax
its color depending on its botanical source, the most common being dark brown
Contents:
has approximately 50 constituents
primarily resins and vegetable balsams (50%), waxes (30%, essential oils (10%),
and pollen (5%). Propolis also contains persistent lipophilic acaricides, a natural
pesticide that deters mite infestations
- prenylated acids such as 4-hydroxy-3,5-diprenyl cinnamic acid
- sinapinic acid, isoferulic acid, caffeic acid
- isoflavonoids, flavonoids
Uses:
bactericidal, anti-fungal, anaesthetic and healing proprieties
"possibly effective" for treating cold sores, genital herpes, and post-surgery mouth
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pain
22
Royal jelly
- garatmirigyváladéka the worker bees,
- bee milk
- fed the young worker bees
- royal jelly gets to eat the womb can ovulate
Main components:
- rich in amino-acids,
- trace elements and vitamins (Vitamin B-s)
- mineral- and trace elements
- therapeutically: stimulating, invigorating and exhilarating, restabilizes
(a positive effect on the nerves) and generally revitalizes .
restore the appetite
action on anaemia
strong antibiotic action
action on some skin troubles
cardiovascular and circulatory systems (anaemias, low blood
pressure, arteriosclerosis)
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Adulteration of honey by artificial invert sugar
bee venom
- honey is carefully mixed with chloroform in a porcelain mortar
- the mixture is filtrered trought filter paper into a porcelain disk and the
chloroformic phase is evaporeted on water bath
- to the residue a few drops of freshly prepared resorcinol solution is added
- the color can be temporarily pinkish or light orange
orange, but should not be red
for a longer period of time (1-2 hours)
Venom, medically known as an 'api-toxin‘,
is a bitter colorless liquid
• has about 40 ingredients
• melittin, an anti-inflammatory drug 100 times stronger
than hydrocortisol
• also enzymes, peptides (They seem to reduce swelling and increase blood
circulation)
• treatment for: multiple sclerosis,
chronic fatigue syndrome,
arthritis, rheumatism,
back pain and
skin diseases
Explanation of the reaction:
Pentose type sugars can be transformed into furfurol (hexoses into
oxymethyl--furfurol
oxymethyl
furfurol)) by heating with hydrochloric acid
acid.. Furfurol reacts with
resorcinol at acidic pH, the reaction product (triphenyl
triphenyl--methane type
molecule)) is red in color
molecule
color.. It has to be noted that certain amount of furfurol may
be formed also in genuine honey by prolonged heating or lengthy storage
storage..
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OLIGOSACCHARIDS
disaccharidess
disaccharide
number of sugars
Disaccharids
(C12H22O11)
- maltose
- genciobiose
- cellobiose
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consists of two monosaccharides
2 glucose
- saccharose
glucose + fructose
Monosaccharides
Disaccharide
Glucose + glucose
Glucose + galactose
Glucose + fructose
maltose + H2O
lactose + H2O
sucrose + H2O
(saccharose the most important saccharide of plants)
Trisaccharids
(C18H32O16)
- gencianose
Tetrasaccharids - manneotetrose
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Maltose
Lactose
• a disaccharide also known as malt sugar
• a disaccharide of β-D-galactose and α- or β-D-glucose
• composed of two D-glucose molecules
• contains a β -1,4-glycosidic bond
• is found in milk and milk products
• obtained from the hydrolysis of starch
• linked by an -1,4-glycosidic bond formed from the  −OH on C1 of
the first glucose and −OH on C4 of the second glucose
• used in cereals, candies, and brewing
• found in both the - and β - forms
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2015.02.18.
DISACCHARIDES
Sucrose
• Hydrolysis of sucrose produces an equimolar mixture of glucose and fructose,
that is sweeter than sucrose itself.
1. oneself
• the resulting glucose fructose mixture is called invert sugar
3. sugar part of glycosides
2. unit of polysaccharides
Saccharide (cane sugar , beet sugar)
• Honey is similar to invert sugar, consisting roughly of 38% fructose, 31% glucose,
9% disaccharides such as maltose and 17% water.
Saccharum officinarum (Poaceae)
tropic
Beta vulgaris (Chenopodiaceae)
Europe
Acer saccharum var.nigrum (Aceraceae)
N-America
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Manna -
Fraxinus ornus L. (Oleaceae) – Manna Ash
Pulpa tamarindorum - Tamarindus indica L.
(Caesalpiniaceae)
Tamarind
exudation
(in july – august: transverse cuts )
H CO
2
Manna canellata
Manna in granis (without damage)
Manna in lacrimis (without damage)
Manna communis (contaminated soil)
constituens:
mannit (70-90%)
mannotriose (6-15%)
glucose, fructose, mannose
fraxin (cumarin)
Medicinal uses:
in pediatric: laxative
for adults: diuretic effect
o
HO
o
O glü
HO
CH OH
2
C H
HO
C
H
H
C
OH
H
C
OH
Drog: evergreen tree in Africa, leaves are evergreen, bright green in color,
elliptical ovular, At night, the leaflets close up.
The fruit is an indehiscent legume, sometimes called a pod, 12 to 15 cm in
length, with a hard, brown shell. The fruit has a fleshy, juicy, acidulous
pulp.
Costituents:
fraxin
-
CH2OH
mannitol
10-15% organic acids: tartaric-, acetic-, citric-, formic-, malic-, succinic acid;
amino acids (alanine, leucin, phenylalanine, prolin, serine),
invert sugar (25-30 %),
pectin,
flavonoids
Medicinal uses:
laxans (osmotic)
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POLISACCHARIDES
Homopolisaccharides
POLYSACCHARIDES
• are polymers of D-glucose
• include amylose and amylopectin, starches made of α-Dglucose
• include glycogen (animal starch in muscle), which is made of
α-D-glucose
• include cellulose (plants and wood), which is made of β-Dglucose
CH2OH
Pentoses
- xylan
hemicellulose
Hexoses
- glükozánok
starches, cellulose
fruktozánok
inulin, triticin
inulin
mannozánok
galaktozánok
Polyuronids - polygalacturonide
red algae (agarose)
pectins
Heteropolisaccharides
*mixed sugars - mannogalactan, mannofructosan (fruits)
O
mixed uronicacids - alginic acid (brown algae)
OH
OH
________________
OH
mixed sugars + uronicacids
OH
α-D-glucose
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gums, *mucilages
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STARCHES
2 fractions:
or amylum is a carbohydrate consisting of a large number of glucose units joined
by glycosidic bonds
this polysaccharide is produced by all green plants as an energy store
amilose
amilopectin
30 %
70 %
Amylose
Official: in Ph.Eur. and in VIII. Hungarian Ph.
Solani amylum
Maydis amylum
Tritici amylum
Orizae amylum
- potato
- maize
- wheat
- rice
Medically: Orizae amylum is the most important (4 – 6 µm)
Tropical and subtropical countries:
Maranth
Tapioca
Sago
- /Maranta arundinacea/
- /Manihot esculenta/
- /Metroxylon species/
Amylopectin
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Starches - depositional centers
centers,, stratification
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Celulose
• a polysaccharide of glucose units in unbranched chains
• has β-1,4-glycosidic bonds
• cannot be digested by humans because humans cannot break down
β-1,4-glycosidic bonds
Lana gossypii - Cotton
Rice
Marantha
Gossypium species /Malvaceae/
-90% cellulose
- the seeds are contained in a capsule called a "boll", each seed
surrounded by fibres of two types
- official in the Ph. Hg. VIII.
Potato
Wheat
Lichen islandicus Lichenin
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Iceland moss
40
Dextrans
60 - 200 glucose unit
- 1 : 3 or/and - 1 : 4 bound
• Dextran is a complex, branched glucan (polysaccharide made of
many glucose molecules) composed of chains of varying lengths
(from 3 to 2000 kilodaltons).
• It is used medicinally as an antithrombotic (anti-platelet), to reduce
blood viscosity, and as a volume expander in anemia.
• The straight chain consists of α-1,6 glycosidic linkages between
glucose molecules, while branches begin from α-1,3 linkages.
Izolichenin
42 - 49
glucose unit
- 1 : 3, - 1 : 4 bound
Uses::
Uses
strongly antibiotic and expectorant. It soothes irritated tissues, especially
mucous membranes and is often used in cough medications.
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2015.02.18.
MANNANS
FRUCTOSES
Mannan is one of the major constituent groups of hemicellulose in the wall of
higher plants. Plant polysaccharide that is a linear polymer of the sugar
mannose. Plant mannans have β(1-4) linkages. It is a form of storage
polysaccharide.
Occurrence:
INULINS - mainly fructoses
(ORCHIDACEAE)
Orchis morio L. or Orchis militaris
Constituens:
Uses:
POLISACCHARIDES
Cichorii radix - Chicory root
Graminis rhizoma - Couch grass
Taraxaci radix - Dandelion root
- in Fabaceae seeds,
- conifers
SALEP TUBER -
sweet taste
POLYFRUCTOSANES = INULIN DRUGS
CICHORII RADIX – Cichorium intibus L.
Asteraceae / Compositae /
50 % not soluble mannans
24 % starch
fatty, albumin
Constituens:
20-82 % inulin
lactukopicrine, laktucine
0,1 -2 % cicoriin /bitter taste/
Mucilago salep: inflamed bowel involvement surfaces
Uses: coffee substitutes, antibilious tea
Aldurelation: Colchici tuber
43
Inulin’s drugs
44
CICHORII RADIX – Cichorium intibus L.
Asteraceae / Compositae /
Constituens:
•
•
•
Inulin
20-82 % inulin
lactukopicrine, laktucine
0,1 -2 % cicoriin /bitter taste/
Uses:
- used as a coffee substitute and additive
- may help humans with weight loss, constipation,
improving bowel function, and general health (contains
inulin)
45
46
Agropyron repens L.
Taraxacum officinale - common dandelion
(Poaceae)
Asteraceae (Compositae)
- couch grass
a very common perennial species of grass native to most of Europe, Asia
Constituens:
main components
components::
- 3-8% polyfructane (inulinszerű triticin),
- 10% mucilage- polysaccharide
- saponin
- 2-3% mannitol, inozitol
- 0,01-0,05% essential oils
- agropyren poliin,
- inulin
- taraxacin,
- acrystalline, bitter substance
Taraxacin
bitter glycoside
Uses:
Medical use:
- used in herbal medicine as a mild diuretic and laxative
- for increasing appetite, and for improving digestion
- liver disease
- diabetes
- rheumatic problems
- blood purifier
- to treat inflamed bladders
- painful urination and
- water retention
- also has antiseptic properties
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2015.02.18.
Heteropolysaccharides
Fucus versiculus
– brown algae -
Ph. Hg.VIII.
• Various red algae
Agar-agar
Carragen
•
alginates
Poliuronids (brown algae)
pectins
alginic acids
*mixture of sugars -
mannogalactane, mannofructosane
uronic acids – alginacid (brown algae)
________________
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Heteropolysaccharides
50
GUMS
gums and *mucilages
- considered to be pathological products (formed by injury of the plant)
- soluble in water and gives a viscous, sticky solution
Gums and mucilage have similar constitutions and on
hydrolysis yield a mixture of sugars and uronic acids
- consist of Ca, Mg and K-salts of polyuronides
- hydrolysed: mixture of sugars and uronic acids
- sugars = monosaccharides (mainly galactose, arabinose, xylose)
Gums: are considered to be pathological products
Gums:
Mucilage:: is formed by normal metabolism
Mucilage
- Families: Leguminosae
Rosaceae
Sterculiaceae
Rutaceae
Drugs:
Tragacanth gum
Sterculia gum
Acacia gum
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52
Mucilages
mucilage drugs
- generally normal products of metabolism formed within the cell (intracellular
Althaeae radix et folium - Marshmallow
formation)
Ph. Hg. VIII.
- water storage reservoir, protection for germinating seeds
Althaea officinalis L. (Malvaceae)
- found in: epidermal leaf cells (Senna)
seed coats (linseeds, psyllium)
root:
roots (marshmallow)
barks (Slippery elm)
- plants: Althaea officinalis
Tussilago farfara
Malva officinalis
Plantago psyllium
Verbascum phlomoides
Plantago lanceolata
Linum usitassimus
Trigonella foenumgraecum
folium: 9-10% mucilage
Cyamopsis tetragonolobus
Pyrus cydonia
30% mucilage (glucose, rhamnose, arabinose, galaktose)
30% starches
10% free sugar
10% pectin
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medicinal uses:
teamixtures,
bronchitis
irritable coughs
ulcus
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2015.02.18.
Malvae folium et flos - common mallow
Verbasci flos – Scrophulariaceae
Malva silvestris L. - Malvaceae
Malva neglecta Wallr. - Malvaceae
Ph.Hg. VIII.
Verbascum phlomoides L.
Verbascum densiflorum Bert.
Content:
8% mucilage
tannin
flos: antocyanin pigment, malvin (malvidin-3,5-diglucoside)
Uses: demulcents and emollients
expectorant properties
laxative
Spec. althaeae
Spec. pectorales
OCH
3
O
O
OH
OCH
+
O
HO
OH
OH
HO
OH
OH
Malvidin
3
OH
Content: Amino acids,
phenolic acids
8% mucilage
10% sugar
caffeic acid esters,
verbascocide and forsythoside B.
acidic saponins,
bitter substances (iridoids)
krocetin / pigment/
3,8% flavonoid - hesperidin, rutin
essential oils
fatty oils
O
rutinóz
(ramnóz + glükóz)
rutin
55
Lini semen - Linum usitatissimum L. (Linaceae)
56
Cyamopsidis seminis pulvis
Constituens:
3-5% mucilage / the outer layer of the seed coat / : galactose, ramnose,
xilose,
galakturonicacid,
mannuronic acid
lignans
30-40 % fatty acids
linolacid
linoleinic acid
arachidonic acid
F- vitamin /linol-, linoleinic-arachidonic acid/
sterols and triterpens
25% protein
Cyamopsis tetragonolobus L.
(Fabaceae)
Guar
Middle East, India , Africa
Seed pods , which won Guar gum
Main component: galactomannan - guaran
uses: teamixtures Ph.Hg.VIII. Oleum Lini – for burn
laxative due to its dietary fiber content
controlling levels of cholesterol and blood sugar
lignans of flaxseed possess in vitro antioxidant and estrogen-like properties
57
uses: -
high viscosity 
apetite 
in diabetes
fatty and cholesterine level 
meal and cosmetic industry
Cydoniae semen et fructus
Farfarae folium et flos
Pyrus cydonia L.
Tussilago farfara L. - Asteraceae
Rosaceae
tartalmaz:
58
– Coltsfoot
Content of folium:
- 7-8% mucilage
- equal to the carbohydrate content of the apple
(30% fructose, 24% galactose, 21% arabinose
15% glucose, 6% uronic acid)
- tannins, salts, sterols and inulin
- rich in vitamin C
- pectin and tannin
(pericarpium and semen)
medicinal uses:
semen : 20% mucilage, pectin
- beneficial effects on bacteria in the digestive track
- cough suppressant". bevonószer, csökkenti a köhögési ingert, légúti
gyulladásoknál a hígabb váladékot fellazítja, megkönnyíti a köhögést.
uses:
-used to treat sore throat and to relieve cough
- pectin – antidotum
- rheuma
- digestion
- Don Quijote Sancho Panza used for stomac pain
- a symbol of fertylity
Side effect: toxic pyrrolizidine (senecionine) alkaloids dangeres for liver
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2015.02.18.
Psyllii semen - Ispaghula
Plantago (laxans
laxans)) products
Plantago psyllium L. Plantaginaceae
Isabgol (Plantago
ovata)
DABUR
Husk Plantago ovata
Content:
10-12% mucilage
xilose, arabinose, ramnose, galacturonic acid
Uses:
Plantago Ovata (Isabgol)
bran, Emblica Officinalis
(Amla)
husk
W. Ratje Frøskaller ApS,
Denmark
laxative
reducing blood cholesterol levels (dietary fiber)
Agiolax granulátum
(MADAUS GmbH)
preparation: Agiolax
Plantago ovata semen and
husk, and
sennae fructus
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Plantago lanceolata L.
62
FoeniFoeni
-graeci semen - Fenugreek
(Plantaginaceae
Plantaginaceae))
Trigonella foenumgraecum L.
The plant is a rosette-forming perennial herb, with leafless, silky, hairy flower stems
Components: aukubin glikoside
iridoids;
flavonoids such as aspigenin, scutellarin, caicalein, nepetin and
plantagoside;
triterpenes;
polysaccharides;
plant acids such as fumaric and benzoic acid;
fatty acids such as oleic acid, ursolic, phosphoric and chlorogenic acids
mucilage
vitamin - C
tannin
SiO2, K, Zn
Uses:
antibacterial
cooling inflammation
inflammatory diseases of the respiratory
antitussivum, expectorans
laxative
63
-Papirus Ebers
-breeding
-China: food, medcine, cosmetic
-lactatio
Ingredients: - 30-38% mucilage
- 0,38% trigonellin / quaternary alkaloid /
Fabaceae
COO+
N
CH
3
trigonellin
Uses:
- blood glucose reducing
- anti - diabetic and cholesterol-lowering effect is indicated by clinical trials
- (4 - hidroxyizoleucin) prevention of diabetes
- steroids positively affect the menstrual cycle
- Anabolic effect of bodybuilders used to develop the muscles
- Chinese folk medicine to treat impotence and other sexual problems
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Thanks for your attention65!
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