COMPUSI LIGNANICI

Definitie
produsi de condensare fenilpropanici
forma macromoleculara - in membrana celulara
dimeri in sucul celular
Structura chimica / Clasificare
pinorezinol

cubebina

conidendrina

 Podophylli rhizoma / Podophyllinum = podofilina

Podophyllum peltatum

Berberidaceae

Compozitie chimica
derivati lignanici (40%)

flavonoli

ulei volatil

podofilol (podofilorezina)

R1

R2

O
O

O
O

H3CO

OCH3

ceara

R1

R2

R3

podofilotoxina

OH

CH3

desoxipodofilotoxina

CH3

desmetilpodofilotoxina

OH

a-peltatina

OH

b-peltatina

OH

CH3

OR3

Actiune terapeutica si intrebuintari

Podophyllinum
act. purgativa beta-peltatina
- 0,01-0,05 g x 3-4ori / zi adulti
- 3 mg / zi ptr. fiecare an varsta - copii
act. colagoga 0,01-0,05 g
act. antibacteriana si antimicotica
act. citotoxica - antimitotic metafaz-specific
extracte uleioase sau alcoolice 25-30%
- CONDYLINE, WARTEC
- dimineata si seara 3 zile consecutiv
- pauza 4 zile
- se repeta de cel mult 5 ori

veruci

CICLUL CELULAR:
interfaza:
perioada G1

perioada S

perioada G2

mitoza:
profaza (a)

metafaza (b)

anafaza (c)

telofaza (d)

H
R

OH
CH2OH

O
HO

OH

CO NH NH CH2 CH3

O
O
H3CO

OCH3

O
O

OCH3

H3CO

OCH3
OCH3

mitopozid

etopozid

R
CH3

tenipozid

 mitopozid PRORESID SP-I

- cancer cutanat

melanom

sarcom

- 5 mg/kg/zi 30 mg/kg/zi
etopozid ETOPOSIDE, SINTOPOSID, VEPESID
- leucemie

- boala Hodgkin

- limfoame nehodgkiene

- cancer testicular

- cancer de san
- carcinom pulmonar cu celule mici
- 100-120 mg/m2/zi 4-5 zile; 3-4 sapt. - leucemie
- 60-120 mg/m2/zi 5 zile cancer pulmonar cu cel. mici
cancer testicular

 tenipozid VUMON
- boala Hodgkin

- limfoame nehodgkiene

- cancer de vezica urinara

- tumori cerebrale maligne
- 30 mg/m2/zi 5 zile; pauza 10 zile
- 40-50 mg/m2/zi 2 ori/sapt. timp de 6-9 sapt.
- 100 mg/m2 la 2 sapt. timp de cateva luni
efecte adverse
etopozid
- leucopenie

- trombocitopenie

- alopecie

- eruptii cutanate

- hepatotoxicitate

- neurotoxicitate

 tenipozid
- eruptii cutanate

- hepatotoxicitate

- neurotoxicitate
Schisandrae semen
Schisandra chinensis

Schisandraceae

Compozitie chimica
derivati lignanici

ulei volatil

OR 1
R 2O
CH3O
CH3O

Actiune terapeutica si
CH3O

intrebuintari

OCH3

act. hepatoprotectoare
R1

schizandrina A
gomisina A

R2
CH3

CH3
CH2

act. antioxidanta

Alti derivati lignanici cu importanta terapeutica

secoizolaricirezinol-diglucozida
H3CO

O Glc

HO

OH

O Glc

HO

OH
flora
intestinala

OCH3

OH

OH

enterodiol
O
HO
O

OH

enterolacto
na

CUMARINE
coumarou Tonka Dipteryx odorata / Fabaceae

Definitie
subst. de natura vegetala
deriv. de benzopiran functie cetonica in
O

Raspandire
alge, ciuperci, licheni
Fabaceae
Apiaceae
Rutaceae
Lamiaceae

benzopiran
(croman)

alfa-pirona
(cumalina)

alfa-benzopirona
(cumarina)

Structura chimica / Clasificare

deriv. de cumarina propriu-zisi

R3
R2

Gl

2
6

R1

HO

3
5

esculina

R 1 =R 2 =R 3 =H
R 1 =R 3 =H, R 2 =OH
R 1 =R 3 =H, R 2 =OCH3
R 1 =R 2 =OH, R 3 =H
R 1 =OCH3, R 2 =OH, R 3 =H
R 1 =OCH3, R 2 =R 3 =OH

cumarina
umbeliferona
herniarina
esculetol
scopoletol
fraxetol

 terpenilcumarine

CH3O

imperatorina

ostol
OH

OH

piranocumarine

visnagan

 furanocumarine

4-fenilcumarine

R2
O

CH3O

HO

R1
R 1 =R 2 =H
R 1 =H, R 2 =OCH3
R 1 =OCH3, R 2 =H

psoralen
xantotoxina
bergapten

dalbergina

izocumarine

izocumarina

 dicumarine
HO

cumestani
HO

HO

matzukazelactona

O O

CH2
OH

OH
dicumarol

metilcumestrol

OCH3

Preparare
comb. glicozidate
- apa fierbinte

- alcool

comb. neglicozidate
- solventi organici nepolari
Proprietati fizico-chimice
solide

cristalizate

miros aromat, caracteristic

fluorescenta in UV
solubilitate
Reactii de identificare
fluorescenta in UV mediu alcalin

Determinare cantitativa
hidroxiacizi aromatici + p-nitro-anilina diazotata /
ac. sulfanilic diazotat

Actiune terapeutica si intrebuintari

act. anticoagulanta dicumarol
inhiba modificarea fiziologica, dependenta de vit. K, a
unor proteine procoagulante sintetizate in ficat:
- protrombina

- factorii VII, IX, X

precursori
CH2
CH2

COOH
carboxilaza /
reductaza

KH2

K
epoxireductaza

K-epoxid
factor de coagulare normal
CH2
HOOC

CH

COOH

 activi pe cale orala

act. lenta si de lunga durata
tromboembolii - profilactic
tromboza venoasa profunda
infarct miocardic
efecte adverse accidente hemoragice
contraindicatii
sarcina

sindroame hemoragice

leziuni susceptibile la sangerare

interactiuni medicamentoase
heparina antiagregante plachetare
antiinflamatoare nesteroidiene
disulfiram, metronidazol, omeprazol, eritromicina,
peniciline, cefalosporine (2, 3), steroizi anabolizanti
barbiturice, rifampicina, grizeofulvina, carbamazepina
deriv. de semisinteza
acenocumarol - TROMBOSTOP, SINTROM
biscumacetat de etil
fenprocumona

warfarina

 Meliloti herba
Melilotus officinalis

M. altissima

sulfina comuna

sulfina inalta

Fabaceae

Compozitie chimica
cumarine (1%)
C 6H11O5
O

OH
COOH

COOH

melilotozida
(produs proaspat)

cumarina
(produs uscat)

acid cumarinic

R1
R2

cumarina
umbeliferona
scopoletol

R1
H
OH
OH

R2
H
H
OCH3

melilotina

O
3

COOH HO

ac. polifenolcarboxilici
O

ac. oleanolic

ulei volatil
polizaharide

acid melilotin-cumarinic

Actiune terapeutica si intrebuintari

act. antiedematoasa

15 20 g extract / zi

act. de capilarprotectoare
act. de imbunatatire a circulatiei venoase si limfatice
act. cicatrizanta
cumarina
antiedematos
imunomodulator

polizaharide

antistres-adaptogen

imunostimulator

insuf. venoasa cronica

tromboflebita

sindrom post-trombotic

hemoroizi

edem limfatic
contuzii

luxatii

fragilitate capilara cutanata

efecte adverse - cumarina (400 7000 mg/zi + cimetidina)

diaree

greata

vertij

insomnie

varsaturi

contraindicatii

disfunctii hepatice

interactiuni medicamentoase
aspirina

warfarina

infuzie
extract fluid
CEAI AROMATIZANT PENTRU BAI
VENALOT
PASCOVENOL
PHLEBODRIL

 Hippocastani cortex
Aesculus hippocastanum

Hippocastanaceae

castan salbatic

castan porcesc
RO

Compozitie chimica
cumarine

flavone

taninuri catehice

alantoina

escina

HO

esculetol

R=H

esculozida

R = Gl

H3CO

H3CO
HO

RO

OR

fraxetol
fraxozida

R=H
R = Gl

scopoletol
R = H scopolozida
R = Gl

OR 4
21
22

OR 3
28

OH

OH

R 1O
R2

baringtogenol C
protoescigenol
-escina

R1
H
H
catena glucidica

R2
H
OH
H/OH

R3
H
H
COCH3

R4
H
H
angeloil
tigloil
-metilbutiril
izobutiril

Actiune terapeutica si intrebuintari

esculozida / esculetol
creste rezistenta peretelui vascular
scade permeabilitatea peretelui vascular
absoarbe UV - B
escina
act. antiexsudativa

act. antiedematoasa

insuficienta venoasa periferica

fragilitate capilara

tromboflebita

hemoroizi

decoct

ulcer varicos

ceaiuri antihemoroidale
ceaiuri antiflebitice

ANAVENOL

 Angelicae radix
Angelica archangelica
angelica

anghelina

Apiaceae

Compozitie chimica
cumarine

H3CO

furanocumarine

OCH3
xantotoxina

OR
ostol

O
O

angelicina

bergapten

R = CH3

izoimperatorina

R=

 ac. polifenolcarboxilici

ac. grasi

flavonoide

taninuri
O

HO

OH

O
archangelenona

ulei volatil (0,36-1,9%) 80-90% hidrocarburi monoterpenice

- alfa, beta felandren

- alfa pinen

- beta cariofilen

- bisabolol

- lactone macrociclice (tri-, penta-, heptadecanolide)

Actiune terapeutica si intrebuintari

act. carminativa

act. stomahica

ulei volatil
act. coleretica

act. colecistokinetica

act. antifermentativa

act. antispastic uterina

act. rubefianta
efecte adverse

fotodermatoze

contraindicatii

ulcer gastric si duodenal

decoct
IBEROGAST

GASTRITOL

STOVALID

CARVOMIN

 Ammi majoris fructus

Ammi majus

Apiaceae

Compozitie chimica
furanocumarine (1%)
taninuri

mucilagii

R2
O

8
5

flavonoide

O
4

R1

psoralen
bergaptenOCH3
xantotoxina
(8-MOP)
izopimpinelina
imperatorina

Actiune terapeutica si intrebuintari

act. fotosensibilizatoare
psoriazis

vitiligo

ulei volatil

R1
H
H

R2
H

H
OCH3
H

OCH3
OCH3
O-CH2-CH=C(CH3)2

 act. fotosensibilizatoare furanocumarine

sensibilizeaza pielea la lumina solara UV-A (320-400 nm)
PUVA = fotochimioterapie
psoriazis - inhibarea sintezei de ADN si a diviziunii cel.
H

O
H

0,65 mg 8-MOP/kg p.o.; dupa 2 ore expunere la UV

repetare la 2 3 zile

1 doza la 1 4 sapt.

 vitiligo stimularea sintezei de melanina

20 40 mg 8-MOP p.o./zi; dupa 2 ore expunere la UVA
sol. 0,1% - badijonaj local o data/sapt.; dupa 1 ora
expunere la UVA
efecte adverse
tulburari gastrointestinale
prurit

stare de nervozitate

reactii fototoxice cancer dermic

contraindicatii
insuficienta cardiaca si renala
ac. nalidixic, tetracicline, sulfamide,
grizeofulvina, fenotiazine

 OXSORALEN

MELADININE

Ammi visnagae fructus

Ammi visnaga

khella
Apiaceae

Compozitie chimica
piranocumarine (0,2-0,5%)

furanocromone (2-4%)
R3

R
visnagan

visnadina

R2

R1

OR

dihidrosamidina

O CO CH3

samidina

H
CO
CO
CO

R1

R2

R3

OCH3

CH3

OCH3

visnagina H

CH3

OCH3

kelinol

OCH3

CH3

OH

kelol

CH2OH

OCH3

kelenina

CH2-O-C6H11O5

OCH3

amiol

OCH3

CH2OH

OCH3

kelina

 furanocumarine

flavone

lipide

proteine

ulei volatil

Actiune terapeutica si intrebuintari

kelina
spasmolitic
- bronhii

- coronare

- cai renale

- cai biliare

- tract gastrointestinal

visnadina
spasmolitic

coronarodilatator

flavone
act. diuretica
kelina

100 mg x 3/zi p.o. sau 80-300 mg i.v.

bronsita spastica

bronsita astmatiforma

astm bronsic

angina pectorala

colici renale, biliare, intestinale

vitiligo

psoriazis

efecte adverse
somnolenta

obnubilare

cefalee

greata

voma

inapetenta

visnadina
angina pectorala

miocardita

STENOCRAT - drajeuri
- 30 mg extract de paducel
- 54 mg extract de Ammi visnagae fructus
5 mg kelina
- 2 drajeuri x 3 / zi
CARDUBEN - tablete
- 35 / 100 mg visnadina
- 100 mg x 3 / zi
- 35 mg x 3 4 /zi