Explain about characterisctic of lipid and its function

1. Structures and Reactions of Naturally
Occurring Compounds Containing Oxygen
Functional Groups

2. CH2O2C(CH2)16CH3
CHO2C(CH2)16CH3
CH2O2C(CH2)16CH3
H
CH2OH
CHOH
CH2OH
+ 3 H2O + 3 CH3(CH2)16CO2H
tristearin
gliseril tristearat)
suatu lemak yang khas
gliserol
(gliserina)
asam stearat
suatu asam lemak
C25H51CO2C28H57 C27H55CO2C32H65 C15H31CO2C16H33
Dlm lilin lebah dlm lilin carnauba setil palmitat
(cetyl palmitate)
dalam spermaceti*
Fats
17.1 LIPIDS
Waxes

3.  Insert table 23.1 page 1132
3

4. 4

5. Nama asam Struktur Sumber
Jenuh:
butirat CH3(CH2)2CO2H Lemak susu
palmitat CH3(CH2)14CO2H Lemak hewani dan
nabati
stearat CH3(CH2)16CO2H Lemak hewani dan
nabati
Tak-jenuh:
palmitoleat CH3(CH2)5CH=CH(CH2)7CO2H Lemak hewani dan
nabati
oleat CH3(CH2)7CH=CH(CH2)7CO2H Lemak hewani dan
nabati
linoleatb CH3(CH2)4CH=CHCH2CH=CH
(CH2)7CO2H
Minyak nabati
linolenatb CH3CH2CH=CHCH2CH=CHCH2CH=
CH(CH2)7CO2H
Minyak biji rami
arakidonatb CH3(CH2)4(CH=CHCH2)4(CH2)2CO2H Minyak nabati
Asam lemak pilihan dan sumbernyaa

6. 6

7. ◦ Hydrogenation of Triacylglycerols
 Liquid vegetable oils can be partially hydrogenated to yield
solid cooking fats
 Partial hydrogenation isomerizes some of the cis double bonds
to trans double bonds
 “Trans” fats have been associated with increased risk of
cardiovascular disease
7

8. Sabun dan Deterjen
CH2O2C
CHO2C
CH2O2C
Suatu trigliserida jenuh:
Dapat sesuai menjadi suatu
kisi yang mampat

9. Suatu trigliserida tak-jenuh
CH2O2C
CHO2C
CH2O2C
Tidak dapat sesuai dengan baik
untuk membentu kisi

10. ◦ Biological Functions of Triacylglycerols
 Triacylglycerols are primarily used as an energy reserve in
animals
 When they are metabolized they yield more than twice the
amount of energy per gram that carbohydrates do
 Fats are a form of long-term energy storage, whereas
carbohydrates are a source of rapid-release energy
◦ Saponification of Triacylglycerols
 Basic hydrolysis of triacylglycerols yields salts of carboxylic
acids and glycerol
10

11. Contoh:
CH2O2C(CH2)16CH3
CHO2C(CH2)16CH3
CH2O2C(CH2)16CH3
kalor
CH2OH
CHOH
CH2OH
+ 3 NaOH + 3 CH3(CH2)16CO2 Na
tristearin gliserol
Sodium stearat
Suatu sabun
tetes
minyak
tetes
minyak
Dalam air sabun, tetes-tetes minyak saling menolak karena
muatan gugus karboksilat sabun sama tandanya

12. Suatu misel (dari) ion-ion alkilkarboksilat suatu sabun

13. Lambang umum untuk suatu surfaktan:
Ekor hidrofobik Kepala hidrofobik
C11H23 CO
O
Na CH2 N
CH3
CH3
C12H25 Cl
O
CH2OH
H
H
OH
OC12H25
H
H
HO
H
HO
Suatu surfaktan
anionik
Suatu surfaktan kationik
(suatu benzalkonium klorida)
Suatu surfaktan netral

14. Permukaan air
2 RCO2
¯ + Ca2+  (RCO2)2Ca
Tak larut

15. CH2 CHCH3
Na2CO3
SO3
SO3 Na
C6H6
SO3H
H2SO4
4
polimerisasi
propilena "tetrapropilena"
suatu detergen yang
tak-biodegradabel

16. CH3(CH2)11 SO3 Na
Natrium p-dodesilbenzenasulfonat
(natrium p-dodecylbenzenesulfonate)
CH3(CH2)11OSO3
¯ Na+
Natrium dodesil sulfat
(natrium lauryl sulfate)

17. Bilayer Membranes: Fosfolipid
R'CO
O
C H
CH2OCR
O
CH2OPOCH2CH2N(CH3)3
O
O
R'CO
O
C H
CH2OCR
O
CH2OPOCH2CH2NH3
O
O
N kuaterner
N primer
Dua tipe fosfogliserida:
Suatu lesitin, atau
fosfatidilkolina
Suatu sefalin, atau
fosfatidiletanolamina
Simbol umum suatu fosfogliserida:
Ekor hidrofobik Kepala hidrofobik

18. R'COCH
O CH2OCH
CH2OPOCH2CH2NH3
CHR
O
O
C
C
H
H CHOH
CHNH
CH3(CH2)12
C(CH2)22CH3
CH2OPOCH2CH2N(CH3)3
O
O
O
Suatu plasmalogen
sfingomielin
Suatu sfinolipid

19. X =
H  asam fosfatidat
serine  fosfatidilserin
etanoleamin  fosfatidileta-
nolamin (sefalin)
kolin  fosfatidilkolin (lesitin)
inositol  fosfatidilinositol
R1= sfingosin  sfingomielin
asam fosfatidat  difosfatidil-
gliserol (kardiolipin)
R2 – C – O – CH
CH2 – O – C – R1
CH2 – O – P – O- X
O-
O
bagian hidrofilik
bagian hidrofobik
O
O
● Fungsi
- komponen utama membran hayati → transfer ion/
sekresi senyawa tertentu melalui membran

20. Glikolipid
glikoprotein
Luar sel/organel
Dalam sel/organel
Intigral protein
Periferal protein
protein
karbohidrat
lipid
● Fungsi lain:
- Lesitin: dalam otak, jaringan saraf, kuning telur, kedelai
→ pengemulsi pada transfer lipid/lemak oleh darah
- Sefalin : dalam jaringan otak → penggumpalan darah
Contoh model ‘fluid mosaic’

21. Bagian luar sel
(suatu medium berair)
Kepala hidrofilik
Ekor hidrofobik Protein tertanam
Bagian dalam sel (suatu medium berair)
Lapisan rangkap fosfolipid dalam suatu membran sel

22. KJM5230 - H06
17.2 Terpenoide Natural Products
O
Isopentenylpyrophosphate
(C-5)
P P
O P P
O
P
O
O
H
3 ATP
OH
HO
O
HO
Mevalonate
(C-6)
N
N N
N
NH2
O
O
OH
HO
P
O
OH
O
P
O
OH
O
P
O
OH
HO
ATP, Adenosine-5'-triphosphate
P
O
Isopentenylpyrophosphate
(C-5)
P P
Rearrange
O
Dimethylallylpyrophosphate
(C-5)
P P
O P P
H
O
trans-Geranylpyrophosphate
(C-10)
P P
Monoterpenes (C-10)
Ex.
OH
Geraniol (+) Limonene
C-10: Monoterpenes
C-15: Sesquiterpenes
C-20: Diterpenes
C-25: Sesterterpenes
C-30: Triterpenes
Natures leaving group

23. KJM5230 - H06
Monoterpenes Voilatile compds, smell, taste etc.
OH
trans-Geraniol
OH
(-)-citronellol (-) Linalool
OH
OH
(+)--Terpineol (-)-Menthol
HO
(+)-Carvone
O
OH
Thymol
O
(+) Camphor -Pinene -Pinene
The Chiral Pool
Pyrethrines
Insecticides from Chrysanthemum cinerariifolium
R
O
O
R'
C-10
Cl
Cl
O
O
O
Synth. analog
more stable
mixt of isomers
Permetrin, Nix®
Shampoo, Lice, scabies
C-10
O
H
H
OH
Tetrahydrocanabinol
O
O
H
H
OH
Nabilone
Antiemetic (not reg N.)
Cannabinoids,
from Cannabis sativa (Hemp)

24. KJM5230 - H06
Diterpenes (C-20) Isopentenyl-
pyrophosphate
(C-5)
O P P
H
O
trans-Geranylpyrophosphate
(C-10)
P P
O
trans, trans-Farnesylpyrophosphate
(C-15)
P P
Isopentenyl-
pyrophosphate
(C-5)
O P P
H
Sesquiterpenes
O
all trans-Geranylgeranylpyrophosphate
(C-20)
P
P
Diterpenes
HO
Phytol
N
N
N
N
Mg
O
CO2Me
H
H
H
O
O
Chlorophyll A
Vitaminee E (-Tocopherol)
O
HO
C-20
Vitamine K1
O
O
Head to tail coupling

25. KJM5230 - H06
Triterpenes (C-20) O
trans, trans-Farnesylpyrophosphate
(C-15)
P P O
P
P
+
tail to tail coupling
Squalene (C-30)
O
HO Lanosterol
H
Squalene
epoxidase
Enzyme-Nu
H
HO
H
H
Enz--Nu
H
Squalene
epoxide
cyclase
(Animals)
H
HO
Cycloartenol
H
HO
H
H
Enz--Nu
H
(Plants)
H
H
B
B
H
Stereoids

26. CH2OH
-karotena
Suatu tetraterpena jingga
trans-vitamin A
2
[O]

27. TAXOL
•Anti-cancer agent
•Pacific Yew Tree
•Ovarian
•Testicular
•Lung
•Breast
•Stabilizes microtubules and prevents
disassembly and re-polymerization

28. KJM5230 - H06
Steroids
A B
C D
1
2
3
4
5
6
7
8
9
10
11
12
13
14 15
16
17
17
17
10
5
A / B trans fused
10
A / B cis fused
5
B / C og C / D always trans (animals)
Cholesterol
Sex hormones
Estrogens
Progesterones
Testosteron and anabolic stereoids
Corticoids
Glucocorticostereoids
Cortison etc. etc.
Mineralcorticostereoidsr
Aldosterone
Digitalis glycosides
Fucidinic acid (antibiotic)
Brassinostereoids (Plant growth hormones)
etc. etc.
HO Lanosterol
(C-30)
H
20 steps
HO
H
H
H
Cholesterol
(C-27)

29. Cholesterol
Cholesterol has a molecular formula of C27H45OH and
it is composed of a hydrocarbon tail ring structure with 4
hydrocarbon rings as well as a hydroxyl group attached
to the carbon 3.

30. Cholesterol is a lipid synthesized by virtually all
cells, but especially liver, intestine, adrenal
cortex, and reproductive tissues
Functions of cholesterol:
• structural component of membranes
• precursor of bile salts, steroid hormones, &
vitamin D

31. CH2
OPP CH2
OPP
CH3
CH2
H
OPP
CH2
OPP
CH2
OPP
H
OPP
C5 C10
CH2
OPP
C15
:B
C15 + C15
squalene
C5 C5
C30
Squalene is the precursor
of all steroids in both
plants and animals.
IPP
DMAPP

32. squalene
O
H
O
H +
“OH+”
+
..
+
..
O
H
CH3
CH3
CH3
CH3
C
H3
CH3
H
H
H
O
H
+
CH3
CH3
C
H3
CH3
CH3
CH3
H
H
O
H
lanosterol
B:
9
The proton at
C9 is lost in an
elimination =
double bond from
C8 to C9
8
9
yellow groups
rearrange by
1,2-shifts
elimination

33. Female Sex Hormone
 Estrogen
Estrogen is derived from terpenes and it carries with 4
condensed rings like others steroid derivatives. A rings
has a hydroxyl group and oxygen substituent present
while the D ring is extending with an alkyl chain.

34. Progestins
Progesterone is the model molecule of sex
hormones. It consists of four interconnected
cyclic hydrocarbons. There are ketone and
oxygenated functional groups with two methyl
branches exit in the structure

35. CH3
H3C
O
CCH3
H
O CH3
O
OH
C CH
Progestin
Progestin
Menekan ovulasi
Noretinodrel
Suatu progestin sintetik
CH3
O
OH
CH3
Metandrostenolon
Suatu steroid pembangun-jaringan

36. Male Sex Hormone
Testosterone
Testosterone naturally produced in the human body has the chemical
formula C19H28O2. Testosterone is referred as a "bioidentical
hormone" which represents the similar chemical structure to natural
synthesized hormone.