O CH3 CH3 O CH3 CH3 CH3 CH3

Vitamin K1 (Phytonadione) 2-Methyl-3-phytyl-1,4-naphthoquinone

O CH3 CH3 O CH3 CH3 n CH3

n = 4 = Vitamin K2 (30) Menaquinone-6 n = 5 = Vitamin K2 (35) Menaquinone-7

O CH3

OCOCH3 CH3

O
Vitamin K3 (Menadione) 2-Methyl-1,4-naphthoquinone

OCOCH3
Vitamin K4

R R' A B R'' R'''

Antihemorrhagic activity significant biologic activity is manifested in compounds with the following structure when:

1. Ring A is aromatic or hydroaromatic

2. Ring A is not substituted 3. Ring B is aromatic or heteroaromatic 4. R = OH, CO, OR, OAc (the R in OR = CH3, CH2CH3 5. R = CH3

6. R = H, sulfonic acid, dimethylamino, or an alkyl grp containing 10 or more C atoms. A double bond in the , - position of this alkyl grp enhances potency, whereas if the double bond is further removed, it exerts no effect. Isoprenoid grps are more effective than straight chains. In the vit. K2 (30) type compds, the 6,7-mono-cis-isomer is significantly less active than all-trans- or the 18,19 mono-cis-isomer. This also was true of the vit K2 (20) isoprenolog. A vit. K2 (25) isoprenolog was 20% more active than vit.K1
(37).

7. R = H, OH, NH2, CO, OR, Ac (the R in OR = CH3- or CH3CH2-)

Decreased antihemorrhagic activity is obtained when:

1. Ring A is substituted 2. R is an alkyl group larger than a methyl group 3. R is a -OH grp 4. R contains a OH (hydroxyl) grp in a side chain

Vitamin K content of selected foods:

Food Brocolli Brussels sprouts g/100g 200 220

Cabbage, Chinese
Cabbage, red Cabbage, white Green onions Kale Lettuce Parsley

175
50 80 60 750 120 700

Spinach
Turnip greens Watercress

350
300 200