Hợp chất tự nhiên pot

HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
Noi Dung Chuong Trinh (18t)
Phan I: Terpenes
Phan II: Steroids
Phan III: Alkaloids
Phan IV: Cac hop chat tu nhien quan trong khac
CAC HOP CHAT TU NHIEN
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1-TERPENES
Terpen la ten duoc Dumas dat cho tinh dau co trong dau turpentine vao nam 1866. Terpene
phan bo rong rai trong tu nhien, thanh phan de bay hoi trong cac loai dau thuc vat. Cau
truc cua terpene bao gom cac monomer duoc goi la isoprene. Isoprenoid la ten goi khac cua
terpen.
Myrcene duoc tach tu bayberry oil
Cau truc camphor duoc xac dinh boi Bredt vao nam 1893, Pinene boi Wagner 1894, citral
boi Tiemann 1895, β-carotene duoc tach tu carrots vao nam 1837 boi Wackenrodder va den
nam 1907 cau truc chinh xac da duoc xac dinh boi Willstaetter.
Giai doan tu 1945, phat minh ky thuat sac ky, pho, nhieu terpenes da duoc xac dinh.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
Mot So Terpenes
O
O
Camphor Pinene Citral
OH
β-carotene

Vitamin A
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1 Su Phan Loai Terpenes
Terpenes
Isoprene
units
Carbon
atoms
1
Monoterpenes 2 10
2 Sesquiterpenes 3 15
3
Diterpenes 4 20
4 Sesterpenes 5 25
5
Triterpenes 6 30
6
Carotenoids 8 40
7 Rubber > 100 > 500
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.1 MONOTERPENES
Monoterpenes la thanh phan tinh dau thom co trong la, hoa qua cua mot so loai thuc vat
nhu Labiatae, Pinaceae, Rutaceae, Umbelliferae. Tinh dau thom duoc dung trong cong
nghe hoa my pham, nuoc hoa, chat mau, mui thuc pham.
Mot so monoterpenes nhu camphor o dang tinh khiet, con da so o dang hon hop cac dong
phan (isomers) kho tach.

Tren 700 cau truc da duoc xac dinh.
Monoterpenes duoc chia lam 03 loai: acyclic, monocyclic va bicyclic.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.1.1 ACYCLIC MONOTERPENES
Acyclic monoterpenes pho bien la geraniol, linalool, nerol va citronellol. Citronellol o dang
tu do hoac dang ester trong nhieu loai dau thuc vat (Rutaceae) duoc su dung trong cong
nghe nuoc hoa.
Acyclic monoterpenes co the duoc xem la dan chat cua 2,6-dimethyloctan.
2,6-dimethyloctan
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.1.1 ACYCLIC MONOTERPENES
Acyclic monoterpenes pho bien la geraniol, linalool, nerol va citronellol. Citronellol o dang
tu do hoac dang ester trong nhieu loai dau thuc vat (Rutaceae) duoc su dung trong cong
nghe nuoc hoa.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.1.2 MONOCYCLIC MONOTERPENES
Monocyclic monoterpenes pho bien la limonene, α-terpineol, terpinolene cung voi 02 loai
tinh dau kha pho bien cua la bac ha la menthol va menthone.
Monocyclic monoterpenes co the duoc xem la dan chat cua cyclohexane voi nhom the
methyl va isopropyl.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.1.2 MONOCYCLIC MONOTERPENES

Monocyclic monoterpenes pho bien la limonene, α-terpineol, terpinolene cung voi 02 loai
tinh dau kha pho bien cua la bac ha la menthol va menthone.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.1.3 BICYCLIC MONOTERPENES
Bicyclic monoterpenes tinh dau pho bien trong mot so loai thuc vat α-pinene, β-pinene,
borneol va thujone.
O
pinene
camphor
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.2 SESQUITERPENES
Sesquiterpenes la thanh phan tinh dau thom co trong la Labiatae, Rutaceae, Myrtaceae and
Pinaceae.
OH
O
O
OH
Abscisic acid (Hormone thuc vat)
Farnesol
. Curcumene
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.3 DITERPENES
Diterpenes la thanh phan resin co nhiet do soi cao cua phan con lai sau khi chung cat tinh
dau.

.
Vitamin A
OH
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.3 DITERPENES
Dang hoat dong nhat cua vitamin E la α-tocopherol (chuoi phytyl bao hoa).
α-tocopherol, co cau hinh tuyet doi 2R-(4'R,8'R)-5,7,8-trimethyltocol, tocol la 02 vong
ngung tu.
.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.3 DITERPENES
α-tocopherol duoc tach ra tu dau mam hat lua mi vao nam 1936, ten tocopherol bat nguon
tu tieng Greek phero nghia la "to bring" va tu tocos, nghia "childbirth”.
Vitamin E tac nhan chong oxi hoa.
.
Vitamin K duoc tim thay 1929 tu nghien cuu cua H. Dam ve qua trinh chuyen hoa
cholesterol trong chim, ong nhan thay nhung trieu chung suy giam moi tu nhung con chim
co che do an kieng chat beo, de bi chay mau, va thoi gian dong mau keo dai.
Nam 1939 nhom nghien cuu Doisy da tach duoc vitamin K tu dich chiet hexane.
Nam 1943 giai Nobel y hoc da duoc trao cho 02 tac gia da kham pha ra vitamin K.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.3 DITERPENES
.
HOA HOC DAI CUONG

Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.4 SESTERPENES
.
Sesterpenes duoc tach tu vo cua con trung va tu nam.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
1.1.5 TRITERPENES
.
Triterpenoids tao ra nhom lon cac hop chat tu nhien steroids, sterols.
Squalene la chat trung gian sinh hoc cua tat ca cac triterpenoids.
Dau gan ca map
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2. STEROIDS - CHOLESTEROL
.
Steroids la loai lipid co nhieu chuc nang trong doi song, la dan chat tu squalene bang phan
ung dong vong, dehydrogen hoa, phan ung the.
Steroids co cau truc co ban gom he 04 vong ngung tu A, B, C, D.
Cholesterol la steroid co so luong lon nhat, la chat trung gian cua tat ca cac steroids trong
dong vat. Nguoi truong thanh co trung binh khoang hon 200 g cholesterol chua trong cac
mo co the, luong lon trong nao va tuy song. Cholesterol la thanh phan boi dap thanh mach
mau, can tro su luu thong cua mau trong he tuan hoan. Cholesterol o dang tu do nhom
alcohol hoac duoc ester hoa boi cac acid beo khac nhau.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2. STEROIDS - CHOLESTEROL

.
OH
H
H
A
B
C D
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23

24
25
26
27
He vong ngung tu trong steroids
Cau truc Cholesterol
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2. STEROIDS - CHOLESTEROL
.
Che do an co cholesterol lien quan den benh dong mo trong mach mau (atherosclerosis) va
benh tim mach.
Ham luong high-density lipoproteins (HDL) va low-density lipoproteins (LDL) trong mau
can duoc xem xet.
Cholesterol la lipid hau nhu khong tan trong nuoc, nen phai duoc nhu tuong hoa de co the
di chuyen trong mau, nho vao chuc nang cua lipoproteins co the nhu tuong hoa va phan bo
lipid khap co the.
HDL dong vai tro chuyen cholesterol tu te bao vao gan de duoc oxi hoa thanh acid mat, chat
dong vai tro quan trong trong qua trinh tieu hoa va bai tiet cholesterol khoi co the. Vi the,
neu luong HDL cao lien quan den “good” cholesterol.
LDL mang cholesterol den te bao qua do tao su ngung dong cholesterol o thanh mach. Neu
luong LDL cao lien quan den “bad” cholesterol va la nguyen nhan cua benh tim mach, xo
vua mach mau. Luong LDL tang cao o nhung nguoi hut thuoc, an che do an nhieu mo.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2.1 VITAMIN D
.
OH

H
H
OH
H
H
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25

26
27
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
7-Dehydrocholesterol

Vitamin D
3
sunlight
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2.1 VITAMIN D
.
Vitamin D
3
co vai tro trong qua trinh hap thu Ca
2+
o ruot non, neu ham luong vitamin D
3
giam se keo theo tinh trang suy giam Ca
2+
trong co the anh huong den su phat trien xuong
(benh Rickets).
Thuc chat benh Rickets do moi truong thieu anh sang. Ca tich luy vitamin D
3
bang qua
trinh khac, dau gan ca la nguon giau vitamin D
3
.
OH
H
H
1
2
3

4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
Ergosterol from yeast, tao vitamin D
2
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2.2 ACIDS MAT

.
Phan chinh cholesterol trong co the duoc su dung de tao cac acid mat. Su oxi hoa trong gan
da chuyen phan chuoi hydrocarbon C
8
H
17
va them nhieu nhom OH tren khung steroid.
Acid Cholic la acid mat pho bien nhat.
Muoi mat dong vai tro quan trong trong qua trinh tieu hoa mo.
OH
H
H
OH
OH
CX
O
1
2
3
4
5
6
7
8
9
10
11
12
13
14

15
16
17
18
19
20
21
22
23
X = OH : Acid Cholic
X = NHCH
2
CH
2
SO
3
Na :
sodiumtaurocholate
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2.3 CORTICOSTEROIDS
.
Vo ngoai tuyen thuong than la nguon tao ra phan lon corticosteroids. Giong acid mat,
corticosteroids cung duoc tao ra tu cholesterol bang su oxy hoa, voi su cat dut chuoi alkyl
tren vong D. Cortisol la chat pho bien cua corticosteroids, trong khi cortisone la chat duoc
biet den nhieu nhat. Cortisone thong thuong duoc chi dinh nhu la thuoc khang viem, dac
biet trong chi dinh dieu tri viem khop.
Corticosteroids cho thay tac dong sinh ly hoc, mot trong nhung chuc nang quan trong la
duy tri can bang dich dien giai trong co the. Corticosteroids cung dong vai tro dieu hoa

chuyen hoa cua carbohydrates.
HOA HOC DAI CUONG
Y – DUOC – RHM Dr. DANG Van Hoai
DAI HOC Y DUOC TP. HO CHI MINH
2.3 CORTICOSTEROIDS
.
H
H
OH
O
OH
O
OH
H
H
OH
O
O
OH
O
1
2
3
4
5
6
7
8
9
10

11
12
13
14
15
16
18
19
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
18
19
Cortisol
Cortisone