Mini Lecture Fundamental Basic Science 1

Fakultas Kedokteran Universitas Wijaya Kusuma Surabaya

Senin, 20 September 2021, jam 14.00-14.50

1. Structure aspect of Lipid

NOER KUMALA INDAHSARI,S.SI, M.Si

VISI DAN MISI FAKULTAS
KEDOKTERAN
UNIVERSITAS WIJAYA KUSUMA SURABAYA
PERIODE 2019 - 2023

VISI
“Menjadi fakultas kedokteran bereputasi nasional pada tahun
2023 dan internasional pada tahun 2031 dengan
menghasilkan lulusan kompeten, unggul dan berorientasi
komunitas berjiwa kewijayakusumaan.”

MISI
1.Menyelenggarakan dan mengembangkan pendidikan kedokteran bermutu untuk
menghasilkan lulusan yang kompeten, unggul, berorientasi komunitas, berjiwa
kewijayakusumaan;
2.Menyelenggarakan dan mengembangkan penelitian serta publikasi ilmiah yang
mendukung perkembangan ilmu pengetahuan teknologi bidang kedokteran,
berorientasi komunitas berjiwa kewijayakusumaan;
3.Menyelenggarakan dan mengembangkan pengabdian pada masyarakat sesuai
dengan kebutuhan masyarakat sebagai upaya penerapan dan pengembangan ilmu
pengetahuan, teknologi kedokteran yang berorientasi komunitas berjiwa
kewijayakusumaan;
4.Meningkatkan tata kelola FK-UWKS yang profesional, akuntabel, transparan dan
bermutu.
 KEDOKTERAN
UNIVERSITAS WIJAYA KUSUMA SURABAYA

“Kewijayakusumaan adalah budaya

perilaku dan sikap, teguh, teteg, tatag,
tanggon, dan trapsila yang tampil secara
reflektif di manapun, kapanpun, dan dalam
kedaan apapun sebagai ciri
khas/karakter/jati diri keluarga besar
Universitas Wijaya Kusuma Surabaya “
Teguh
Teteg
Tatag
:berarti konsisten dan bertanggung jawab terhadap janji
:berarti tidak mudah goyah keteguhannya
:berarti tidak gentar menghadapi rintangan.
Tanggon :berarti dapat dipercaya/amanah.
Trapsila :berarti berperilaku santun dan rendah hati
 Macromolecule

• Large organic molecules.

• Also called POLYMERS.
POLYMERS
• Made up of smaller “building blocks”
called MONOMERS.
MONOMERS
• Examples:
1. Carbohydrates
2. Lipids
3. Proteins
4. Nucleic acids (DNA and RNA)
2. LIPIDS
Introduction
• Any member of a large and diverse group of
oils, fats, and fat like substances that occur
in living organisms and that
characteristically are soluble in organic
solvents but only sparingly soluble in
aqueous solvents.
• Lipids are not polymers, but mostly small
molecules.
• Chief cellular storage form of energy
• Role in cellular structure and biochemical
functions
 Role of lipid
1. energy source,
2. helps to hold the body organs and nerves in position,
3. vital organ protection,
4. body temperature isolation,
5. cell wall structure,
6. skin and hair lubrication,
7. aids transport and absorption of the fat-soluble vitamins
LAMPHIPATHIC LIPIDS Form Membranes, Micelles,
Liposomes, & Emulsions

 In general, lipids are insoluble in water since they contain a

predominance of nonpolar (hydrocarbon) groups. However, fatty
acids, phospholipids, sphingolipids, bile salts, and, to a lesser
extent, cholesterol contain polar groups

 Therefore, a part of the molecule is hydrophobic, or water

insoluble; and a part is hydrophilic, or water soluble. Such
molecules are described as amphipathic

 They become oriented at oil-water interfaceswith the polar group

in the water phase and the nonpolar group in the oil phase. A
bilayer of such amphipathic lipids is the basic structure in
biologic membranes
LIPIDS ARE CLASSIFIED AS SIMPLE
OR COMPLEX
1. FATTY ACIDS
• Simplest form of lipids
• Carboxylic acids with HC side chain O

• Usually contains an even number of carbon

ǁ
atoms (14C- 20C) – biosynthesis of fatty acid
R-C
– OH
occurs with sequential addition of 2 carbon atom.
• Chain may be saturated (containing no double
bonds) or unsaturated (containing one or more
double bonds)
• It occurs mainly in esterified form.
• Fats of animal origin are more simple than that of
plant origin.
• Palmitic acid and stearic acid – most common
 Unsaturated Fatty Acids

• Fatty acids may be further subdivided as follows

– Monounsaturated (monoethenoid, monoenoic)
acids, containing one double bond.
– Polyunsaturated (polyethenoid, polyenoic) acids,
containing two or more double bonds.
– Eicosanoids: These compounds, derived from eicosa-
(20-carbon) polyenoic fatty acids, comprise
the prostanoids, leukotrienes (LTs) and lipoxins (LXs).
Prostanoids include prostaglandins (PGs), prostacyclins
(PGIs), and thromboxanes (TXs).
 Essential fatty acids
• The fatty acid cant be synthesized by the body
and therefore has to be supplied in the diet.
• Ex: Linoleic Acid, Linolenic Acid
• Archidonic acid becomes essential – precursor
linoleic acid is not provided in the diet
• Functions of EFA
–Membrane structures and functions
–Transport of cholesterol
–Formation of lipoprotein
–Prevention of fatty liver
• Deficiency of EFA : Phrynoderma – toad skin
Food source
• SAFA sources: meat and products, poultry,
especially the skin part, etc
• MUFA sources: Avocado, olive, peanut, almond.
• PUFA sources:
Omega-6: leavy vegetable, seeds, nuts, grains,
vegetable oil, meat, etc.
Omega-3: fats and oil (canola, soybean, walnut,
wheat germ, margarine and shortening), nuts
and seeds (butternuts, walnuts, soybean
kernels), vegetables (soybeans), human milk,
etc.
 Review of Fatty Acid
Nomenclature

• Chain length
– Most fatty acids have an equal number of
carbons
• Fish oil is rich in odd-numbered FAs
• Double bonds
– Number
– Location from methyl or carboxyl end
– Degree of “saturation”
H H2 H H H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH
 Fatty-acid Nomenclature

• Named according to
chain length
– C18

H2 H2 H2 H2 H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH
 Fatty-acid Nomenclature

• Named according to the number of

double bonds
– C18:0

H2 H2 H2 H2 H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH

Common
Common name:
name:
Stearic
Stearic acid
acid
 Fatty-acid Nomenclature

• Named according to the number of

double bonds
– C18:1

H2 H2 H2 H H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H H2 H2 H2 OH

Common
Common name:
name:
Oleic
Oleic acid
acid
 Fatty-acid Nomenclature

• Named according to the

location of the first double bond from the non-
carboxyl end (count from the methyl end)
– Omega system (e.g., omega 3, 3)
– n–system (e.g., n–3)

H H2 H H H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH
 Fatty-acid Nomenclature

H2 H2 H2 H H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H H2 H2 H2 OH

Omega 9 or n–9 fatty acid

H2 H2 H H H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H H2 H H2 H2 H2 OH
Omega 6 or n–6 fatty acid
H H2 H H H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH
Omega 3 or n–3 fatty acid
 2.Triglyceride
• A triglyceride is
composed of an alcohol
called glycerol
covalently bonded to
three fatty acid
molecules by
dehydration synthesis
reactions. This process
forms three ester groups
between the alcohol and
one with each fatty acid
chain. Is this a saturated or unsaturated
Fat? Why or Why not?
It is saturated because there are no double bonds between carbon atoms in the
fatty acid hydrocarbon chains.
TRIASILGLISEROL/TRIGLYCERIDA
 3. WAX
:
They are esters of higher fatty acids with higher mono hydroxy
aliphatic alcohols(e.g. Cetyl alcohol)
Have very long straight chain of 60-100 carbon atoms
They can take up water without getting dissolved in it
Used as bases for the preparation of cosmetics, ointments, polishes,
lubricants and candles.
In nature, they are found on the surface of plants and insects.

figure CETIL ALKOHOL and MIRISIL ALKOHOL

beeswax
4. Phospholipids
Phosphatidate

O H2 C O C R2

R1 C O CH O

H2 C O P O

O
phosphatidate

In phosphatidate:
 fatty acids are esterified to hydroxyls on C1 & C2
 the C3 hydroxyl is esterified to Pi.
 O

O H2C O C R2

R1 C O CH O

H2C O P O X

O
glycerophospholipid

In most glycerophospholipids (phosphoglycerides),

Pi is in turn esterified to OH of a polar head group (X):
e.g., serine, choline, ethanolamine, glycerol, or
inositol.
.
 O

O H2 C O C R2

R1 C O CH O

H2 C O P O

O H

OH OH
H OH
OH H
phosphatidyl- H H
inositol
H OH

Phosphatidylinositol, with inositol as polar head

group, is one glycerophospholipid.
In addition to being a membrane lipid,
phosphatidylinositol has roles in cell signaling.
 O

O H 2C O C R2

R1 C O CH O CH3
+
H 2C O P O CH2 CH2 N CH3

O CH3

p h o sp h atid ylch o lin e

Phosphatidylcholine, with choline as polar

head group, is another glycerophospholipid.
It is a common membrane lipid.
 O

O H2C O C R2
Each glycerophospholipid
R1 C O CH O
includes
 a polar region: H2C O P O X
glycerol, carbonyl O
O
of fatty acids, Pi, & the glycerophospholipid
polar head group (X)
 non-polar hydrocarbon
tails of fatty acids (R1, R2).
5. SFINGOLIPID
 Merupakan derivat sfingosin atau yang mempunyai
struktur mirip misalnya dihidrosfingosin

Gambar sfingosin dan dihidrosfingosin

Sphingophospholipids
 Sphingolipids

Seramida adalah derivat sfingosin yang mengandung

gugus asil dari asam lemak. Gugus ini terikat pada gugus
asam amino dalam bentuk amida. Seramida terdapat dalam
jumlah kecil pada jaringan hewan mapun tumbuhan
 Sphingolipids
Sfingomielin merupakan sfingolipid yang
mengandung fosfat. Sfingomielin terdapat terutama
dalam jaringan syaraf. Dalam otak jg terdapat
sfingomielin yang mengandung sfingosin dengan
beberapa ikatan rangkap.
 Sphingolipids
 Golongan sfingolipid yang mengandung karbohdrat
disebud GLIKOLIPID, contohnya: serebrosida
 Serebrosida terdapat dalam jaringan syaraf
Hidrolisis Serebrosida akan menghasilkan molekul
sfingosin, asam lemak dan heksosa, terutama galaktosa
dan kadang glukosa
6. Terpen
 Merupakan senyawa yang terdiri atas beberapa
molekul isoprena (2-metilbutadiena) atau senyawa
yang mempunyai struktural dengan isprena

Terdiri atas kelipatan dari 5 atom karbon

Contoh: sitral, pinen, geraniol, kamfer, karoten,
vitamin A, fitol dan skualen
 7.Steroids
 Merupakan derivat perhidklopentanofenantrena.Ada 3
Cincin A,B,C adalah penanthrena dan cincin D adalah siklo
pentana termasuk dlm suatu kelompok yang disebut
STEROID. Kesamaan antara rumus struktur senyawa-
senyawa steroid ini ialah adanya struktur inti, sebagai berikut:
GAMBAR INTI STEROID
 TATA NAMA
1. Untuk memberi nama steroid digunakan patokan: yaitu beberapa jenis
hidrokarbon yang mempunyai rumus tertentu sebagai senyawa asal, misalnya
etiokolana, alopregana, andostana, pregnana, estrana
 TATA NAMA

2. Garis vertikal pada atom C 10 dan 13 menunjukkan gugus metil

3. Jika terdapat ikatan rangkap maka namasenyawa diberi akhiran ena dan
untuk dua ikatan rangkap diberi akhiran –diena
4. Posisi ikatan rangkap ditunjukkan dengan tanda segitiga (∆) dengan
angka di bagian atasnya yang menyatakan atom C yang menjadi awal
ikatan rangkap tersebut.
Contoh:
a. ∆5- androstena berarti ikatan rangkap berawal dari atom C 5 dan berakhir
pada atom C6.
b. ∆7.9.11- androstadiena berarti ada 2 ikatan rangkap, yg pertama berawal
pada C7 dan berakhir pada C8, yang kedua berawal pd C9 dan berakhir
pd C11 bukan pd C10
5. Bila pd atom C terdapat atom oksigen dlm bentuk C=O diberi tambahan –
on
6. Bila tdp gugus –OH diberi tambahan –ol
7. Bila tdp gugus aldehid diberi tambahan -al
 Contoh: ∆1.3.5-estratriena-3ol-17-on, artinya terdapat 3 ikatan rangkap yaitu pd C1
dan C2, C3 dan C4, C5 dan C6, gugus –OH pd C3, atom O pd C17

8.Kadang digunakan tanda (α) dan (β) untuk menyatakan konfigurasi suatu garisbila
dibandingkan keseluruhan struktur.
Contoh: pada molekul testosteron gugus –OH pd atom C17 sama dg kedua gugus
metil pd atom C 10 dan C13 diberi tanda (β).

GAMBAR TESTOSTERON
GAMBAR TESTOSTERON
Referensi

• Murray R, Bender D, • Ngili Y., Biokimia;

Botham K, Kennely P, Konsep-konsep dan
Rodwell V, Weil P, Latihan Soal.1th ed ,
Harper 2017, Pebnerbit
Boichemistry.29th ed., Rekayasa Sains
2014
Bandung
• Gurr M, Harwood J,
Faryn K, Lipid
Biochemistry and
Introduction. 5th ed,
2002