Chapter 4.

Vitamins and
Coenzymes
Lecture 1. Water-soluble vitamins
and coenzymes
Lecture 2. Fat-soluble vitamins
 Introduction of Vitamins

• Organic molecules, essential for the

normal growth and development,
required in tiny amounts
• Cannot be synthesized by mammalian
cells, must be supplied in the diet
 The Classification of Vitamins

 Water-soluble ： thiamineVB1, riboflavinVB2,

pantothenic acid （ VB3 ） , niacin （ VPP 、 VB5 ） ,

VB6, biotin （ VB7 ） , folic acid （ VB11 ?VB9 ） ,

cobalaminVB12, VC

 Fat-soluble ： VA 、 VD 、 VE 、 VK
 Lecture 1

Water-soluble Vitamins and Coenzymes

 1. VitB3

 Nicotinamide Coenzymes
 Containing: nicotinic acid , nicotinamide
 Coenzyme ： NADH and NADPH
 Function ： the coenzyme of
dehydrogenase ， transfer of hydride anion
 The nicotinamide coenzymes play a role in
many oxidation–reduction reactions.
 Mechanism ：
• Deficiency
• Pellagra.

呕吐、失眠、疲劳
Snapshot 7-8, p, 238
 2. VitB2

 Riboflavin—— precursor for the

coenzymes FAD, FMN
 Flavin Coenzymes

Riboflavin powder
 FMN, FAD

Coenzyme ：

Flavin mononucleotide
FMN

Flavin adenine dinucleotide

FAD
Function ： electron acceptors and donors
in the oxidation-reduction reactions
 FMN + 2H == FMNH2
 FAD + 2H == FADH2
Deficiency ： Growth retardation
 3. VB5, Pantothenic Acid
 Coenzyme A
 “Pantothenic acid”
 Function:
This coenzyme is involved in acyl-
group–transfer reactions
 Deficiency:
4. VB1 （ Thiamin ）
 Thiamin pyrophosphate （ TPP ）
 The first discovery of vitamin
 Structure ：
Coenzyme: thiamine pyrophosphate
TPP
- cofactor for the pyruvate dehydrogenase

-α-ketoglutarate dehydrogenase catalyzed

reactions

-the coenzyme of pyruvate decarboxylase

-the transketolase catalyzed reactions of

the pentose phosphate pathway.
 Deficiency ： beriberi
sources ：

Snapshot 7-6, p, 236

 5. VitB6
 Pyridoxine
 Coenzyme ： pyridoxal
phosphate （ PLP ） and pyridoxamine
phosphate （ PMP ） （— NH3)

 Function ：
 Coenzymes of amino acid metabolism (transamination ,
decarboxylation, racemization)
Deficiency ：
- Anemia
- Skin problems
- Sores in the mouth
Snapshot 7-11, p, 243
 6. VitC
 Ascorbic Acid

Reduction Oxidation
 Function ：

• Prevention of scurvy （ protect the membrane ）

• Participate in oxidation-reduction reaction
• The coenzyme of prolyl hydroxylase
（ the synthesis of collagen protein ）

 Deficiency ： scurvy
Snapshot 7-5, p, 232
 6. Biotin
 Vitamin H （ VB7 ）
 Cocarboxylase

O
Urea C
HN NH
HC CH
Thiophene
H2C CH (CH2)4 COOH
S Pentanoate 【戊酸】
Function ：
Biotin is a
prosthetic group
for enzymes that
catalyze carboxyl
group transfer
reactions
and ATP-
dependent
carboxylation
reactions.
 7. Folic Acid （ Folate ）
 VitM, VB11

6-Methylpteridin p-Aminobenzoic acid (PABA)

Pteroic acid Glutamic acid

Peteroylglutamic acid
 Coenzymes ： tetrahydrofolic acid （ THFA, FH4 ）

 Function ： the coenzyme of one-carbon

units transferase
 -CH3 、 -CH2- 、 -C(O)-H 、 =C-
 Deficiency: megaloblastic anemia
 8. VB12

 Cobalamin
 Function ： Methyltransferases, Methyl (-CH3)
group transfers between two molecules.

 Deficiency ： pernicious anemia

Snapshot 7-10, p, 242
 9. Lipoic Acid
 Forms ： lipoic acid （ oxidized form ） and
dihydrolipoic acid （ reduced form ）

 Function ： electron carrier ； acyl group carrier

 Lecture 2

Fat-soluble Vitamins
 1. VA

 Retinol
 Sources ： animals and β-carotene

CH3 CH3 CH3 CH3

CH3 H CH3 H
C CH2OH C CH2OH
C C CH C C C CH C
H H H H H H

H3C CH3 H3C CH3

VA1 VA2
retinol dehydroretinol
 Deficiency: Night Blindness
Snapshot 7-1, p, 219
 2. VD
 Function ：
Promotes calcium （ Ca ） and
phosphonium （ P ） absorption into intestine.

CH3
CH3 H CH3 Skin of animals ：
C C C C C
H H2 H2 H2 CH3 7-dehydrocholesterol
CH3

CH3
CH3 H CH3
HO C C C C C
H H 2 H 2 H2 CH3
UV CH2

230~300nm
HO VD3
 Deficiency: rickets, osteomalacia
Snapshot 7-2, p, 223
3. VE

 -Tocopherol

  ，， and  are physiological

active.
  -Tocopherol is the most active form.
 Functions ：

 Maintaining animal procreating ability,

anti-infertilitas.
 An antioxidant in cells ： prevent the
oxidation of unsaturated fatty acids.
 Promote metabolism of heme.
Sources and Deficiency
Snapshot 7-3, p, 226
 4. VK
 They are 2-methyl-1,4-naphthoquinone (3-) derivatives

VK1
12
43

VK2
 Functions ： promote the blood clotting
• Blood coagulation: prothrombin (factor II), factors
VII, IX, and X, and proteins C, S, and Z
• Bone metabolism: osteocalcin, also called bone Gla
protein (BGP), matrix Gla protein (MGP),[36] and
periostin.
• Vascular biology: growth arrest-specific protein 6
(Gas6)
 Deficiency: coagulopathy
Snapshot 7-4, p, 228