Steroid compounds

• They are considered derivatives of a hypothetical

hydrocarbon
• called steran which comprises 3 cyclohexane nuclei and
1 condensed cyclopentanic nucleus:
a

Steran

• Steroid compounds differ in their functional groups and

side chains grafted onto the steric nucleus, the presence of
double bonds and the existence of a large number of
stereoisomers.
Steroizi naturali Nr. atomi de carbon Hidrocarbura fundamentală

Hormoni estrogeni 18

Estran

Hormoni androgeni 19
( testosteron )
Androstan

Hormoni corticosteroizi şi
21
progestageni
Pregnan

Acizi biliari 24 Colan

Steroli 27

Colestan
 Sterols
• Steroid alcohols are present in all
living organisms.
• This category includes cholesterol and
its metabolic products, bile acids.
 Cholesterol
• Steroid with 27 carbon atoms derived
from cholesterol hydrocarbon
• It is not found in plants, microorganisms
and invertebrates
• The most important sterol in the animal
kingdom
• It is in the constitution of all lipoprotein
membranes
• In the blood it is either in free form or
• esterified with fatty acids in the
constitution
• plasma lipoproteins (chylomicrons, VLDL,
LDL, HDL)
 Cholesterol
17

3
HO 5
6
Cholesterol
It has a weak amphipathic character
Cholesterol esters are among the most hydrophobic cellular
constituents
It has a structural role, being present in most cell membranes
It is the precursor of all steroid compounds: bile acids, steroid
hormones, vitamin D3
In the liver it is converted into bile acids which are eliminated
in the form of bile salts, with the aqueous flow of bile through
the intestine.
 Bile acids
• They are products of cholesterol catabolism
• They are the main components of the ball
• They are steroids with 24 carbon atoms,
derivatives of colan hydrocarbon.

• Primary bile acids are synthesized in the liver:

• Cholic acid (3α, 7α, 12α trihydroxycolanic)
• Chenodeoxycholic acid (3α, 7α
dihydroxicolanic)
 Bile acids
OH

COOH COOH

HO OH HO OH

Acid colic Acid

chenodezoxicolic
• In the liver it is conjugated with taurine (H2N-
CH2-CH2-SO3H)
• or glycochol (H2N-CH2-COOH) forming
conjugated bile acids: glycocholic acid,
• taurocholic, glycochenodeoxycholic acid and
taurochenodeoxycholic acid
 Acizii biliari
Acizi biliari conjugati

OH OH

CO CO
HO OH NH HO OH NH
CH2 CH2

- CH2
COO
SO3-
Acid gliocolic Acid taurocolic

• From the liver, conjugated bile acids reach the

bile where, due to the alkaline pH, they turn
into bile salts, which are eliminated with the bile
in the duodenum.
 Acizii biliari
• Due to the amphipathic nature, bile salts
interact with water and other lipids to
form mixed micellar aggregates: non-
polar molecules (triglycerides and
cholesterol esters) are in the center of
the micelle, and outside are polar
molecules (phosphatides, free
cholesterol).
• Bile salts play a role in emulsifying lipids
in the intestine
Micele lipidice
 Acizii biliari
• After the lipids have been hydrolyzed by the
specific enzymes and absorbed into
enterocytes, the bile salts remain in the
intestine and are converted into secondary
bile acids (by losing the –OH group in
position 7):
• Deoxycholic acid (3α, 12 α dihydroxycolic)
• Lithocolic acid (3 α hydroxycolanic acid)
 Acizii biliari
Acizi biliari secundari
OH

COOH COOH

HO HO

Acid deoxicolic Acid litocolic

• In the distal part of the ileum, secondary bile acids
are absorbed by an active mechanism and reach the
liver through the port system, where they are
transformed again into primary bile acids and resume
the enterohepatic circuit.
• Some of the secondary bile acids escape reabsorption
and are eliminated in the feces (0.8 g / day), being
the major form of cholesterol elimination.