Analysis of macro nutrients

2 CARBOHYDRATES

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 1/33
 Carbohydrates

2.1 CLASSIFICATION, STRUCTURE AND

CHEMICAL CHARACTERISTICS

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 2/33
 Contents
1 Introduction
2 Monosaccharides
3 Disaccharides
4 Oligosaccharides
5 Polysaccharides
Exercises

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 3/33
 1 Introduction (1/6)
Carbohydrates
• The most abundant organic compounds on earth
• Composition: C, H, O
• General empirical formula Cx(H2O)y
• Function:
Body  macro nutrient: major source -70%- of energy (about 4
kcal/g or 17 kJ/g), satiety, cell metabolism, apart of cells, dietary
fibers, prebiotic
Food  taste: sweetener, colour: browning agent, texture -from
cripness to smooth- (stabilizer, gels, foams, filler, thickening agent,
edible film, fat replacer)

Sources: Belitz and Grosch 1999, p. 237; Fennema 1996, p. 158; Kusnandar 2010, p. 80;
BeMiller 2010, p. 149
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 4/33
 1 Introduction (2/6)
Energy value of carbohydrates (1/2)
1 gram of carbohydrates
• Photosynthesis:
• 6 CO2 + 6 H2O  C6H12O6 + 6 O2 (ΔH: 675 kcal/mol)
• MW C6H12O6 = 180
 1 mol C6H12O6 (hexoses)  675/180 = 3.75 kcal/g
1 gram of sucrose
• 3.95 kcal/g sucrose
• Digestibility of sucrose = 98 %
 Digestible calorie = 3.95 x 98% = 3.87 kcal/g sucrose

Source: Winarno 1997, p. 16f

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 5/33
 1 Introduction (3/6)
Energy value of carbohydrates (2/2)
1 gram of polysaccharides (starch)
• Polymerization of hexoses  polysaccharides  4.18 kcal/g starch
• Digestibility of starch = 98-99%
• Total digestible energy of 1 g starch
= 0.98 x 4.18 = 4.0 kcal/g starch

Source: Winarno 1997, p. 16f

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 6/33
 1 Introduction (4/6)
Classification based on the digestibility
1 Digestible carbohydrate or available carbohydrate or glycemic
carbohydrate: simple sugars (mono- and disaccharides), starch,
dextrin and glycogen
2 Indigestible carbohydrate or unavailable carbohydrate or non-
glycemic carbohydrate: oligosaccharides  flatulence (stachyose,
raffinose, verbaskose), cellulose, hemicelluloses, pectin, gum and
lignin

Source: Winarno 1997, p. 18ff; Belitz and Grosch 1999, p. 237ff; Fennema 1996, p. 158ff;
Kusnandar 2010, p. 81; BeMiller 2010, p. 149
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 7/33
 1 Introduction (5/6)
Classification based on the analytical characteristic
1 Crude fiber: indigestible
2 Nitrogen Free Extract (NFE):
 other compounds which are not measured during proximate
analysis
 rough estimation of carbohydrate content
NFE = 100 - % (water + fat + protein + crude fiber +ash)

What are the constituent components of NFE?

Source: Winarno 1997, p. 18ff; Belitz and Grosch 1999, p. 237ff; Fennema 1996, p. 158ff;
Kusnandar 2010, p. 81
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 8/33
 1 Introduction (6/6)
Classification based on the molecular structure
1 Monosaccharide
2 Disaccharides  2 monosaccharide residues (glycosidic linkage)
3 Oligosaccharides  3-10 monosaccharide residues
4 Polysaccharides  >10 monosaccharide residues

What is polymerization degree?

Source: Winarno 1997, p. 18ff; Belitz and Grosch 1999, p. 237ff; Fennema 1996, p. 158ff;
Kusnandar 2010, p. 81; BeMiller 2010, p. 149
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 9/33
 2 Monosaccharides (1/8)
 Simple sugars
Basic stucture (based on functional group)
1 Polyhydroxyl + aldehide  aldoses
Trioses (3C), e.g.: Glyceraldehyde
Tetroses (4C), e.g.: Erythrose, Threose
Pentoses (5C), e.g.:
- Apiose (parsley, cerely seed)
- Arabinose, Xylose (hemicelluloses, pectine, glycosides)
- Ribose (RNA, DNA)
Hexoses (6C), e.g.: (abundant in fruits and vegetables)
- Galactose
- Glucose
- Mannose
Source: Belitz and Grosch 1999, p. 240; Fennema 1996, p. 161; Kusnandar 2010, p. 84; BeMiller
2010, p. 149
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 10/33
 Rosanoff structure of D-aldoses

Source: Belitz and Grosch 1999, p. 239

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 11/33
 2 Monosaccharides (3/8)
2 Polyhydroxyl + ketose  ketoses
Hexuloses (6C), e.g.: Fructose: honey
Heptulose (7C), Octulose (8C), Nonulose (9C): avocado fruit

Source: Belitz and Grosch 1999, p. 241; Fennema 1996, p. 162; Kusnandar 2010, p. 87
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 12/33
 2 Monosaccharides (4/8)
Rosanoff structure of D-ketoses

Source: Belitz and Grosch 1999, p. 240

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 13/33
 2 Monosaccharides (5/8)
3 Polyhydroxyl  glycitol/alditol (sugar alcohols)
e.g.: 6C  mannitol, xylitol, sorbitol (pears, apples, plums,
mushrooms, strawberry)
4 Polyhydroxyl + carboxilic acid  gluconat
5 Polyhydroxyl + aldehide + carboxilic acid  uronic acid
e.g.: galacturonic acid

oxidation
alcohol  aldehide  carboxilic acid
alditol  aldose  aldonic acid
glucose  reduction  glucitol/sorbitol
fructose  reduction  glucitol +mannitol

Source: Belitz and Grosch 1999, p. 241; Fennema 1996, p. 168; Kusnandar 2010, p. 82
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 14/33
 2 Monosaccharides (6/8)
3 projections: Fischer, Haworth, and chair conformation

Sources: Fennema 1996; Belitz et al. 2009; Kusnandar 2010, p. 85ff

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 15/33
 2 Monosaccharides (7/8)
Basic stucture
• Dextro- and Levo- formation (D and L)
OH on Cn-1  right (D) or left (L)
• α- and β- formation
OH on Cn-1 + aldehides/ketoses group  hemiacetal formation
 “jembatan oksigen“  haworth projection
α  below the ring
β  above the ring
• OH on C1 (aldoses  aldehide group) / C2 (ketoses  ketose
group)  reducing group  reducing sugars

Sources: Fennema 1996; Belitz et al. 2009; Kusnandar 2010, p. 90

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 16/33
 2 Monosaccharides (8/8)
Reducing sugars + amino compounds  maillard reaction
Galactose > mannose > glucose > fructose
Amino compounds?....
Trigger factors: t, T,aw (0.5-0.8), ionic metal (Cu, Fe), SO2
Products:
- Brown pigments  melanoidins
e.g.: baking/roasting foods, condensed milk, dried soups
- Volatile compounds  aroma flavor substances like pirazine
e.g.: coffee, grilled meat and fish
- Reductive compounds  reductones
- Losses of ess. aa  lysine, cysteine, methionine
- Cross linkage of protein  induce diabetes
Source: Belitz and Grosch 1999, p. 258; Fennema 1996, p. 171; Kusnandar 2010, p. 97
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 17/33
 3 Disaccharides (1/4)
Basic stucture
• 2 saccaride residues
• Glycosidic bound

Examples
• Maltose  ….  hydrolysis of starch
• Lactose  ….  milk
• Sucrose  ….  abundant in fruits and vegetables, honey

Which one is reducing sugars and which one is not? and why?

Source: Belitz and Grosch 1999, p. 258; Fennema 1996, p. 171; Kusnandar 2010, p. 97
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 18/33
 3 Disaccharides (2/4)

Chemical structure of sucrose?

Sources: Fennema 1996, p. 323; Belitz et al. 2009, p. 9; Kusnandar 2010, p.207
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 19/33
 3 Disaccharides (3/4)

Glucose - α (1-2) - Fructose

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 20/33
 3 Disaccharides (4/4)
Level of sweetness
• Saccarine 20000-70000
• Cyclamate 3000-8000
• Aspartame 200
• Acesulfame-K 200
• Fructose 1.3
• Xylitol 1.01
• Maltose 1.0
• Galactose 0.4-0.6
• Sucrose 1.0
• Glucose 0.56
• Invert sugar 0.85-1.0
• Xylose 0.59

Source: Kusnandar 2010, p. 95

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 21/33
 4 Oligosaccharides (1/3)
Basic stucture
• 3 - 9 saccaride residues
• Glycosidic bound

Examples
• Trisaccharides: raffinose (soybean, mung bean, sugar beet, sugar
cane, sweet potato
• Tetrasaccharides: stachyose (legumes, artichoke, soybean)
• Pentasaccharides: Verbaskose (cereals)
• FOS (Fructo-Oligosaccharides): dahlias, asparagus, wheat, banana,
onion
 might be fermented by microflora (probiotic) in colon

Source: Belitz and Grosch 1999, p. 258; Fennema 1996, p. 171; Kusnandar 2010, p. 97
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 22/33
 4 Oligosaccharides (2/3)

Source: Belitz and Grosch 1999, p. 258; Fennema 1996, p. 171; Kusnandar 2010, p. 97
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 23/33
 4 Oligosaccharides (3/3)

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 24/33
 5 Polysaccharides (1/5)
Basic stucture
• 10 - >200 saccaride residues
• Glycosidic bound
• “karbohidrat kompleks“

Examples
• Digestible: maltodextrin (DP 10-200), starch (amilosa, amilopectin)
• Indigestible: cellulose, hemicellulose, pectin, inulin

Source: Winarno 1997, p. 27; Belitz and Grosch 1999, p. 283; Fennema 1996, p. 178; Kusnandar
2010, p. 104f
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 25/33
 5 Polysaccharides (2/5)
1. Pati
• Tidak larut dalam air dingin, alkohol dan eter
• Mengembang dan membentuk pasta dengan air hangat 
viskositas makanan
• Dapat dihidrolisis oleh enzim dan asam menghasilkan dekstrin,
maltosa, dan glukosa
• Membentuk warna biru dengan iodine
• Terdiri dari dua jenis: amilosa (linier  ikatan α1-4) dan
amilopektin (bercabang, ikatan α1-4 dan α1-6)  karakteristik
pasta dan nasi

2. Dextrin
• Produk konversi pati oleh asam atau enzim
• Dextrin amilodextrin erytrodextrin maltofdextrin
• Membentuk warna coklat dengan iodine
Source: Winarno 1997, p. 27ff; Belitz and Grosch 1999, p. 297f; Fennema 1996, p. 178ff;
Kusnandar 2010, p. 104f
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 26/33
 5 Polysaccharides (4/5)
3. Glikogen
• Cadangan karbohidrat pada hewan (hati dan otot)
• Terdiri dari satuan α-D-glukosa
• Membentuk warna merah dengan iodine
• Mempunyai BM < dari BM pati
• Bersifat koloidal dalam air

4. Selulosa
• Bersama hemiselulosa, pektin, dan protein membentuk
struktur jaringan sel tanaman
• Terdiri dari satuan β-D-glukosa dengan ikatan 1-4
• Tidak dapat dicerna oleh enzim-enzim pencernaan manusia
• Hidrolisis memerlukan asam-asam kuat
• Sukar larut dalam air, asam, atau basa encer
• Tidak bereaksi dengan iodine

Source: Winarno 1997, p. 27; Belitz and Grosch 1999, p. 28;2ff Fennema 1996, p. 178ff;
Kusnandar 2010, p. 104f
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 28/33
 5 Polysaccharides (5/5)
5. Hemiselulosa
• Dapat diekstrak oleh alkali
• Non-fibrous
• Terdiri dari unit xylan, pentosa, dan metil uronat
• Mudah larut dalam alkali tapi sukar larut dalam asam
6. Pectin
• Stabilizer (milk, juices), thickening (jams, jellies, ice cream, yoghurt)
• Heteropolisakarida dari asam poligalakturonat
• Dapat membentuk gel
7. Inulin
• Diperoleh dari umbi articoke dan dahlia
• Sedikit larut dalam air dingin dan asam
• Tidak memberikan warna merah atau biru dengan iodine
• Hidrolisis menghasilkan laefulosa
Source: Winarno 1997, p. 27; Belitz and Grosch 1999, p. 282; Fennema 1996, p. 178ff;
Kusnandar 2010, p. 104f
AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 29/33
 Exercises
1. Sebutkan komponen monosakarida dari senyawa berikut dan
contoh sumber bahan pangannya!
a. starch b. dextrin c. cellulose
d. glycogen e. hemicelluloses f. pectin
g. raffinose h. sucrose i. Lactose
j. maltose k. stachyose l. trehalose

2. Which one is available and which one is unavailable carbohydrate ?

a. starch b. cellulose c. glycogen
d. FOS e. maltose f. raffinose
g. D-xylose h. D-mannitol j. glycerol

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 30/33
 Exercises
3. Please describe the structure of these compounds based on the
projection of Fischer and Haworth!
a. Glucose b. Fructose c. Galactose

4. What is the different between dietary fiber and crude fiber?

5. What is the different between soluble fiber and insoluble fiber?

6. What is the different between enzymatic and non-enzymatic

browning reaction? Please give some examples of each!

7. Mention some examples of functional carbohydrates!

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 31/33
 References (1/2)
Figures
Carbohydrates. http://healthy-eating.org.uk/wp-content/uploads/2011/02/Complex-
Carbohydrates.jpg
Glucose Haworth.
http://upload.wikimedia.org/wikipedia/commons/6/64/Glucose_Haworth.png
Linear and ring form of glucose. http://html.rincondelvago.com/000280461.png
Lactose and maltose.
http://accessscience.com/loadBinary.aspx?filename=107910FG0050.gif
Conformation structure of glucose.
http://131.104.156.23/Lectures/CHEM_207/CHM_207_Pictures_NMR/NMR_karpl
us_glucosecolor.gif
Sucrose http://themedicalbiochemistrypage.org/images/sucrose.jpg
FOS http://jn.nutrition.org/content/128/6/934/F1.expansion.html
http://jn.nutrition.org/content/128/1/11/F2.expansion.html

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 32/33
 References (2/2)
Kusnandar F. 2010. Kimia pangan: Komponen makro. Dian Rakyat: Jakarta.
Winarno FG. 1997. Kimia pangan dan gizi. PT Gramedia Pustaka Utama:
Jakarta.
Belitz H-D, Grosch W, Schieberle P. 2009. Food Chemistry. 4th revised and
extended Edition. Springer-Verlag: Berlin, Heidelberg.
Fennema OR. 1996. Food Chemistry. 3rd Ed. Marcel Dekker, Inc. : New York,
Basel, Hongkong.
BeMiller JN. 2010. Carbohydrate analysis. In: Nielsen SS. Food analysis. 4th
ed. Springer, New York.

AZG team – Department of Community Nutrition – Faculty of Human Ecology – IPB 33/33