Farmakognosi

Komposisi nilai
• Kuis : 20%
• Tugas : 50%
• UAS : 30%
 Materi Kuliah
• Fenilpropanoid
• Flavonoid
• Alkaloid : 2
• Terpenoid
• Zat Pahit
 Penugasan
• Membuat makalah dan presentasi terkait produk yg
mengandung metabolit sekunder tsb.
• Batasan tugas : profil produk (nama produk, foto,
komposisi, dosis, cara penggunaan, manfaat/khasiat),
kandungan metabolit yg terkandung, sumber
tumbuhan dan cara isolasi metabolit tsb, mekanisme
aksi metabolit dalam menimbulkan khasiat (bila
khasiatnya banyak, pilih 1 khasiat yg lengkap
mekanisme aksinya, min. Diperoleh dari 5 jurnal)
• Makalah lengkap : cover, daftar isi, isi, kesimpulan,
daftar pustaka
Fenilpropanoid
 Klasifikasi fenilpropan
• Fenilpropanoid (C6-C3)
• Flavonoid (C6-C3-C6)
 Klasifikasi fenilpropanoid
• Asam hidroksisinamat
• Fenilpropena
• Kumarin
• Fenilpropanoid pendek
• Turunan bifenilpropenoid
• Fenilpropanoid BM tinggi phenylpropane

biphenylpropane
 Asam hidroksisinamat
• Asam para-kumarat
• Asam kafeat
• Asam ferulat
• Asam sinapat
 Asam para-kumarat
• Sinonim : asam p-hidroksisinamat
• Sumber biologis : Lidah buaya (Aloe barbadensis
Mill), Mole plant (Euphorbia lathyris L.), Apel
(Malus sylvestris Mill.)
• Pemerian : berbentuk jarum dan memiliki titik
lebur 210-213°C. Mudah larut dalam etanol, eter,
dan air panas, sukar larut dalam air dingin, dan
praktis tidak larut dalam benzen.
• Manfaat : antioksidan, menghambat
pembentukan platelet (in vitro dan in vivo)
 Asam Kafeat
• Sinonim : Asam 3,4-dihidroksisinamat
• Sumber biologis : Kopi (Coffea sp.),
Wintergreen (Gaultheria procumbens L.), Red
clover (Trifolium pratense L.)
• Pembuatan : asam kafeat pada tumbuhan
hanya berada dalam bentuk terkonjugasi,
misal asam klorogenat. Asam ini juga telah
diisolasi dari kopi hijau dan kopi panggang
• Pemerian : bentuk kristal kuning dari larutan air pekat dan
bentuk monohidrat dari larutan encer. Asam kafeat melunak
pada 194°C dan mengurai pada 223-225°C. Mudah larut
dalam etanol dan air panas, agak sukar larut dalam air dingin
• Uji kimia :
1. Asam kafeat berubah warna dari kuning menjadi jingga
dalam media basa
2. Asam kafeat segera membentuk metil ester (C10H10O4) yg
diperoleh sebagai kristal tak berwarna dari air (titik lebur
152-153°C)
• Manfaat : antioksidan, menghambat xantin oksidase,
menghambat replikasi virus Hepatitis B (in vitro dan in vivo)
 Asam ferulat
• Sinonim : asam kafeat 3-metil eter, asam 4-
hidroksi-3-hidroksisinamat
• Sumber biologis : resin Asafoetida (Ferula
assafoetida L.), perdu Saw palmetto (Serenoa
repens (Bartel.), ranting ivy (Hedera helix L.), Pirus
laricio Poir. (Abietineae)
• Pembuatan : diisolasi dari Ferula foetida Reg
(Umbelliferae) dan Pirus laricio Poir. (Abietineae).
Asam ferulat jg dapat disiapkan melalui interaksi
vanilin, asam malonat, dan piperidin dalam
piridin selama 3 minggu dan kemudian endapkan
asam ferulat dengan HCl encer
• Pemerian :
– Bentuk cis : minyak kuning, UVmaks (dalam etanol) :
316nm
– Bentuk trans : jarum ortorombik yg diperoleh dari air,
titik leleh 174°C, UVmaks (dalam etanol) : 236 dan
322nm. Larut dalam air panas, etanol, dan etil asetat,
cukup larut dalam eter, agak sukar larut dalam benzen
dan PE
• Uji identifikasi : asam ferulat dengan larutan NaOH
membentuk garam natrium sehingga menyebabkan
kelarutannya cukup meningkat
• Kegunaan : asam ferulat digunakan sbg pengawet produk
makanan, antioksidan
 Asam sinapat
• Sumber biologis : daun dan ranting European
mistletoe (Viscum album L.) (Loranthaceae)
• Pembuatan : hidrolisis ester kolin asam sinapat dari biji
mustard hitam (Brassica nigra Koch (Cruciferae), baik
dalam media asam maupun dg hidrolisis enzimatik.

• Kegunaan :
1. Asam sinapat digunakan sbg antiseptik,
antispasmodik, dan emetik
2. Asam sinapat juga digunakan pada arteriosklerosis,
stimulan jantung, kanker, hepatosis, dan hipertensi
3. Asam sinapat juga telah digunakan dalam
penanganan epilepsi, histeria, dan debilitas saraf
 Fenilpropena
• Sinonim : sinamal, fenilakrolein, sinamat aldehid
• Sumber biologis : minyak kayu manis Sri Langka
(Cinnamomum verum J.S Presler) (Lauraceae),
balsam Peru (Myroxylon balsamum var.Pereirae
(Royle) Harms (Fabaceae), cengkeh (Syzygium
aromaticum (L.) Merr&Perry (Myrtaceae)
• Pembuatan : minyak kasia (Cinnamomum cassia
Blume) mengandung minyak atsiri 1-2%. Minyak
atsiri ini mengandung sinamaldehid 80-85% yg
diisolasi melalui distilasi fraksional dalam vakum.
• Pemerian : cairan berminyak kekuningan yg
memiliki bau kayu manis yg tajam. Parameter
fisiknya d2525 1,048-1,052; TD100 177,7°C; TD200
199,3°C and TD760 246°C. Sinamaldehid larut
dalam 700 bagian air dan 7 bagian etanol 60%.
Akan tetapi, sinamaldehid tdk bercampur dg
etanol, eter, kloroform, dan minyak.
• Uji kimia : penambahan setetes larutan FeCl3 1%
b/v menghasilkan warna cokelat yg khas
• Kegunaan :
1. Fenilpropena banyak digunakan pd industri
parfum
2. Fenil propena digunakan utk memberikan aroma
pada makanan dan minuman
 Kumarin
• Kumarin
• Hidroksikumarin
– Umbelliferon
– Eskuletin
– Skopoletin
– Dafentin
– Fraksetin
• Furanokumarin
– Psoralen
– Metoksalen
– Bergapten
– Imperatorin
Kumarin
• Sinonim : asam cis-o-lakton kumarinat, kumarin,
kumarinat anhidrat, kamfer biji tonka
• Sumber biologis : Biji tonka (Dipteryx odorata (Aubl)
Willd), Anisi (Pimpinella anisum L.), Seledri (Apium
graveolens L.)
• Pemerian : kristal kumarin memiliki lempeng
ortorombik dan rektangular. Kumarin memiliki bau yg
enak dan wangi mirip dg biji vanili dan rasa terbakar.
• Karakter fisika : titik leleh 68-70°C dan titik didih 297-
299°C. Kumarin larut dalam etanol, kloroform, eter,
minyak, dan larutan NaOH/KOH, agak sukar larut dlm
air panas (1:50), sukar larut dlm air dingin (1:400)
• Kegunaan : kumarin banyak digunakan sbg pemberi
aroma pada formulasi obat
Hidroksikumarin
Umbelliferon
• Synonyms Hydrangin; Skimmetin.
• Biological Sources Umbelliferone is present in a variety of medicinal
plants, for instance: Apium graveolens L. (Apiaceae) Celery; Dipteryx
odorata (Aubl.) Willd. (Fabaceae)-Tonka Bean; Ferula sumbul Hook.
(Apiaceae)-Sumbul; Lavandule angustifolia Mill. (Lamiaceae)-Lavender;
Matricaria chamomilla L. (Asteraceae)-Hungarian Camomile; and
Pimpinella anisum L. (Apiaceae)-Anise.
• Preparation Asafoetida contains resin (40-65%) which consits of chiefly a
resin-alcohol asaresinotannol both in the free or combined form with
ferulic acid, and of course, free umbelliferone is totally absent in the drug.
Thus, umbelliferone is prepared by treating ferulic acid with HCl which
gets converted to umbellic acid and the latter loses a molecule of water to
give rise to umbelliferone
• Umbelliferone may also be obtained by distillation of resin from
Umbelliferae.
• Characteristic Features It is obtained as needles from water. It
develops the characteristic odour of coumarin on heating. Its mp is
225-228°C. It usually sublimes. Its solubility in water is very poor
i.e., it dissolves 1 g in nearly 100 ml of boiling water. It is freely
soluble in ethanol, chloroform, acetic acid and dilute alkaline
solution. It is sparingly soluble in ether and the solutions exhibit a
distinct blue fluorescence.
• Identification Test When 0.5 g of umbelliferone is triturated with
pure sand (SiO2) and 5 ml of HCl, added 5 ml of water, filtered and
to the filtrate added an equal volume of ammonia solution, it gives
a beautiful blue fluorescence.
• Uses
1. It is an important ingredient in most sunscreen lotions and creams.
2. It is most importantly used as an intracellular and pH sensitive
fluorescent indicator and bloodbrain-barrier (BBB) probe.
 Esculetin
• Synonyms Aesculetin; Chicorigenin; 6, 7-Dihydroxy-coumarin.
• Biological Source It is the aglucon of esculin and cichorlin: Esculin is
derived from two different plant sources, namely: (a) the barks of
Crataegus oxycantha L. (Rosaceae)-Hawthorn; and (b) the flowers
of Centarea cyanus Linn., (Compositae). It is a glucoside which upon
hydrolysis gives the aglucon esculetin.
• Esculetin is also obtained from cichorlin, which is a glucoside and
found to be isomeric with esculin. Cichorlin is present in the flowers
of the chicory plant (Chichorium intybus L., family: Compositae).
• Uses : antioxidant, inhibitor human leukemia cell inhibitor,
antiinflamation (in vivo and in vitro)
 Skopoletin
• Synonyms Chrysatropic acid; Gelseminic acid; 6-
Methoxyumbelliferone; β-Methylesculetin; 7-Hydroxy 6-
methoxycoumarin
• Biological Sources It is the aglucone of scopolin. Scopoletin occurs
in the roots of Arnica montana L. (Asteraceae)-Mountain Tobacco,
Leopard’s-bane; leaves of Artemesia abrotanum L. (Asteraceae)-
Southernwood, Old Man; roots and leaves of Atropa belladona L.
(Solanaceae)-Belladonna, Deadly Nightshade; barks of Brunfelsia
uniflorus (Phol.) D. Don. (Solanaceae)-Manaca, Manacan; fruits
of Capsicum annuum L. (Solanaceae)-Chili, Sweet Peppers,
Paprika; oil of the plant Chamaemelum nobile (L.) All. (Asteraceae)-
Roman Comomile; English Camomile, Comomile; and roots
of Withania somniferum (L.) Dunal (Solanaceae)-Ashwagandha.
• Preparation It is obtained by the hydrolysis of the glucoside
scopolin i.e., 7-(β-D glucopyranosyloxy)-6-methoxy-2H-1-
benzopyran-2-one as follows:

• Characteristic Features Scopoletin occurs as prisms or

needles from either acetic acid or chloroform. It melts at
204°C. It is slightly soluble in water or cold ethanol and
quite soluble in hot ethanol and hot glacial acetic acid. It is
moderately soluble in chloroform, but practically insoluble
in the non-polar solvent benzene.
• Uses :
– Antioksidant, antifungal, immunomodulator, hepatoprotective
(in vitro and in vivo)
 Dafentin
• Synonyms 7, 8-Dihydroxycoumarin
• Biological Sources It is the aglucon of daphnin. It is
obtained from the seeds and fruits of Daphne
mezereum L. (Thymelaeaceae)-Mezereon; and the seeds
of Euphorbia lathyris L. (Euphorbiaceae)-Mole Plant,
Petroleum Plant, Caper Spurge.
• Preparation Daphentin is prepared conveniently from its
glucoside known as daphnin i.e., 7, 8-dihydroxycoumarin
7-β-D-glucoside by treating the latter in three different
ways, namely: (i) By boiling with dilute mineral acids; (ii)
By enzymatic hydrolysis; and (iii) By sublimation as given
below:
• Characteristic Features The crystals obtained
from dilute ethanol has a mp 256°C
(decomposes). It undergoes sublimation on
heating. It is soluble in boiling water, hot dilute
alcohol and hot glacial acetic acid. It is found to
be sparingly soluble in ether, chloroform, and
benzene.
• Identification Tests
• 1. An aqueous solution of daphentin gives a
green colouration with FeCl3 solution, which
turns red on the addition of sodium carbonate.
• 2. An alkaline solution of daphentin in alkali
carbonate or alkali gives a yellow colour.
 Fraksetin
• Synonyms 7, 8-Dihydroxy-6-methoxycoumarin.
• Biological Source It is the aglucon of fraxin. Fraxin is
present in the seeds of Acsculus hippocastanum L.
(Hippocastanaceae)-Horse Chestnut.
• Preparation Fraxetin is obtained by
heating fraxin with dilute sulphuric acid to affect the
hydrolysis of glucoside and get the desired aglucon
residue as shown here under:
• Characteristic Features Fraxetin is obtained as
plates from ethanol having mp 228°C. It has
been observed that it turns first yellow at
150°C and subsequently brown at mp. It is
soluble in 10 L of cold water, but in 300 ml of
boiling water. It is somewhat more soluble in
alcohol and practically insoluble in ether.
• Uses : Antioxidant, neuropotective (in vitro)
 Furanokumarin
• Furanocoumarins, represent a class of
relatively more complex coumarins that occur
in various natural plant products. A few
important members of this particular class
are, namely: Psoralen; Methoxsalen;
Bergapten; and Imperatorin.
 Psoralen
• Synonyms Ficusin; 6-Hydroxy-5-Benzofuranacrylic acid d-lactone;
Furo (3, 2-d)-coumarin.
• Biological Source Psoralen belongs to one of a group of
furanocoumarins occurring naturally in more than two dozen
different plant sources, for instance: Rutaceae (e.g., Bergamot,
Limes, Cloves); Umbelliferae (Celery; Parsnips); Leguminosae (e.g.,
Psoralen coryfolia). It is also found in the Rue Oil obtained from
Ruta graveolens L. (Rutaceae)-known as Rue (daun inggu). It is
obtained from the leaves of Ficus carica Linn. (Moraceae)-Figs.
• Characteristic Features Psoralen crystals from ether have two sets
of melting points e.g., 163-164°C and 169-179°C (Spath). It is very
soluble in chloroform, less soluble in alcohol, sparingly soluble in
ether and practically insoluble in petroleum ether (60-80°C).
Identification Tests
• 1. Dissolve 1 mg of psoralen is 5 ml of ethanol and add to it 15 ml of
a mixture made up of 3 parts of propylene glycol, 5 parts of acetic
acid and 43 parts of water. The resulting mixture on being exposed
to the uv-light in a uv-chamber, gives a distinct blue-fluorescence.
• 2. When 1 mg is dissolved in 2 ml ethanol, mixed with two drops of
NaOH solution (0.1 M) and the resulting solution is subjected to uv-
light, it emits a yellow fluorescence.
Uses
1. It is used in the treatment of leucoderma patches.
2. Psoralens have also exhibited photosensitizing and phototoxic
effects in animals and human beings and, hence have been
employed extensively in photochemotherapy for the treatment and
management of vitiligo, psoriasis and mycosis fungoides.
3. It is used orally as laxative
 Metoksalen
Synonyms Xanthotoxin; Meloxine; Ammoidin; Meladinine; 8-
Methoxypsoralen; 8-MOP; 8-MP; Oxsoralen.
Biological Source Methoxsalen is a naturally occurring analogue of psoralen,
found in various species of Rutaceae, Leguminosae, and Umbelliferae. It is
obtained from the fruits of Fragara xanthoxyloides and the fruits of Ammi
majus belonging to the natural order Umbelliferae. It is also found in the
herb Ruta graveolens (Rutaceae).
Isolation The various steps involved are as under:
1. The A. majus fruits are dried, powdered, sieved and extracted with
petroleum ether to complete exhaustion.
2. The petroleum ether extract is filtered and concentrated to obtain a dark
green semi-crystalline solid mass (crude methoxalen) crystallizes out.
3. The residual dark-green solid mass is dissolved in minimum quantity of
ethanol and boiled over an electric water-bath for 45-60 minutes. The
contents are filtered immediately and the filtrate is concentrated under
vacuum. It is cooled in a refrigerator overnight when pale-green crystals
separate out. The crystals of methoxsalen thus obtained are purified first
by washing with boiling water and finally recrystallizing from ethyl acetate.
Characteristic Features
1. It is obtained in two forms: first—as silky needles either from hot water or benzene
+ petroleum ether; secondly—as long rhombic prisms from ethanol + ether, having
mp 148°C.
2. It is odourless but has a distinct bitter taste followed by tingling sensation.
3. It has a pH 5.5.
4. Solubility Profile: It is practically insoluble in cold water; sparingly soluble in boiling
water, liquid petroleum, ether; soluble in boiling ethanol, acetone, acetic acid,
vegetable fixed oils, propylene glycol, benzene; freely soluble in chloroform; and
soluble in aqueous alkalies with ring cleavage, but is reconstituted upon
neutralization.
Identification Tests These are as follows:
1. A few crystals of methoxsalen on being triturated with little sulphuric acid in a
porcelain dish produces an orange-yellow colour that gets changed to light green
finally.
2. Wagner’s Reagent Test: Xanthotoxin gives an instant precipitate with Wagner’s
Reagent (I2 + KI).
3. HNO3 Test: It gives a distinct yellow colouration with dilute HNO3, which on
rendering to alkaline with KOH or NaOH, changes to crimson colour.
Uses
1. It is used extensively in the treatment of leukoderma.
2. It is employed as a pigmentation agent.
3. It is also used in the treatment of psoriasis and mycosis fungoides.
 Bergapten
Synonyms Bergapten; Heraclin; Majudin; Psoraderm; 5-
Methoxypsoralen; 5-MOP.
Biological Source Bergapten is the naturally occurring analogue of
psoralen and an isomer of methoxsalen, mostly found in a wide
variety of plants, such as: roots and fruits of Angelica archangelica
L. (Apiaceae)-Angelica, Garden Angelica, European Angelica; seeds
of Apium graveolens L. (Apiaceae)-Celery; leaves, stems and fruits
of Petroselinum crispum (Mill.) Nym. (Apiaceae)-Parsley; Rue Oil of
Ruta graveolens L. (Rutaceae)-Rue, Garden Rue, German Rue.
Preparation Bergapten was first isolated from the oil of bergamot
from Citrus bergamia Risso., belonging to the natural order
Aurantiodiae*. It was also isolated from Fagara xanthoxyloides
Lam., belonging to family Rutaceae.**
Characteristic Features The crystals obtained from
ethanol are needle-shaped having mp 188°C. It
sublimes on heating. It is practically insoluble in boiling
water, slightly soluble in glacial acetic acid, chloroform,
benzene, and warm phenol. It is soluble in absolute
ethanol (1 part in 60).
Identification Test It gives a distinct yellow-gold
colouration when its solution is treated with a few
drops of concentrate H2SO4.
Uses
1. It is used in photochemotherapy of psoriasis.
2. It has been used to promote tanning in suntan
preparations e.g., creams and lotions.
 Imperatorin

Synonyms Ammidin; Pentosalen; Marmelosin;

Biological Sources It is obtained from the roots and fruits
of Angelica archangelica L. (Apiaceae) (Angelica,
Garden Angelica, European Angelica); from the roots
of Imperatoria osthruthium L. (Umbelliferae); from fruit
of Pastinaea sativa L. (Umbelliferae); and also in the
fruits of Ammimajus (Umbelliferae). However, the seed
oil of A. archangelica is said to contain upto 0.5%
imperatorin.
Uses : anticonvulsant, vasodilator (in vitro and in vivo)
Isolation The various steps involved are as follows:
1. The petroleum ether mother liquor left after the separation of methoxsalen (Xanthotoxin), is
concentrated under vacuo and allowed to cool in a refrigerator overnight when the crude
imperatorin separates out.
2. The crude product is collected, dissolved in ether, filtered and concentrated under reduced
pressure. It is kept in a refrigerator, and the crystals separating out are purified subsequently
by recrystallization from ethanol.
Characteristic Features These are as given below:
1. It is obtained in two forms: First—as prisms from ether, and secondly—as long fine needles
from hot water, having mp 102°C.
2. Solubility Profile: It is practically insoluble in cold water; very sparingly soluble in boiling water;
freely soluble in chloroform; and soluble in benzene, ethanol, ether, petroleum, ether alkali
hydroxides.
Identification Tests These are as stated below:
1. Sulphuric Acid Test: Imperatorin gives an intense deep orange colouration with a few drops of
sulphuric acid which ultimately changes to brown colour.
2. Marqui’s Reagent: It gives an orange colouration with Marqui’s Reagent that rapidly changes to
brown.
3. Tollen’s Reagent (Ammoniacal AgNO3): It reduces Tollen’s Reagent to produce a silver mirror.
4. Fehlings Test: It reduces Fehling’s solution to give a brick-red precipitate of cupric oxide.
5. Nitric Acid Test: It gives a distinct yellow colour on boiling with dilute HNO3, and this colour
changes to purple on being treated with strong alkali e.g. NaOH or KOH.
Sebutkan nama, golongan senyawa, dan manfaat
dari struktur-struktur di bawah ini :

O O HO O O
O

1
2
O

H
O O

3 4
O
O
H3CO
HO OH
OH

HO
HO
5 OCH3 6
 Fenilpropanoid Rantai Pendek
• Berbagai fenilpropanoid rantai pendek yg
terdapat pada banyak herba obat biasanya
diklasifikasikan menjadi 3 kelas utama yaitu :
1.Tidak memiliki rantai samping
2.Memiliki rantai samping dengan 1 atom C, dan
3.Memiliki rantai samping dengan 2 atom C
Fenilpropanoid tidak memiliki rantai OH

samping
• Katekol OH

• Sinonim : Pirokatekol, Pirokatekin, 1,2-

dihidroksibenzen
• Sumber biologis : Anandenathera peregrina
L.speg (Mimosaceae)-Niopo, Yupa; korteks Melia
azedaraeh L.(Meliaceae)-Chinaberry; Rumex
crispus L.(Polygonaceae)-Yellow Dock
• Pembuatan : ekstrak air dapat diperlakukan dg
basa encer scr hati-hati, dan garam natrium yg
dihasilkan dinetralkan utk menghasilkan katekol
dari sumber tumbuhan alam
• Pemerian : katekol diperoleh sbg tablet atau prisma
monoklinat dari toluena. Katekol biasanya mengalami
perubahan warna jika terpajan udara dan cahaya.
• Karakteristik fisik: titik lebur 105°C; d 1,344; TD₇₆₀ 245,5°C.
Katekol larut dlm 2,3bagian air, etanol, benzen, kloroform,
dan eter, sangat larut dlm larutan air alkali dan piridin.
Larutan air katekol diketahui segera berubah mjd cokelat.
• Uji identifikasi: larutkan 0,2g katekol dlm air dan
tambahkan beberapa tetes larutan air FeCl₃ (0,1%b/v).
Perubahan warna menjadi hijau menunjukkan adanya
katekol.
• Kegunaan :
1. Katekol digunakan sbg bahan antiseptik
2. Katekol diketahui digunakan dlm fotografi
3. Katekol juga digunakan dlm pewarnaan bulu binatang
Fenilpropanoid dg rantai samping 1 atom C
COOH

COOH

HO OH

benzoic acid
OH O H

Asam galat
OH

O-D-Glukosa

OCH3

OH

Salisin Vanilin
 Asam Benzoat
• Sinonim : asam drasiklik, asam fenilformat, asam
benzen karboksilat
• Sumber biologis : asam benzoat ditemukan dlm
btk bebas dan kombinasi. Gom benzoin
mengandung asam benzoat 20%, buah buni
(berry) mengandung asam benzoat cukupbesar
0,05%. Minyak Cananga odorata (Lam.)
Hook.f&Thoms.(Fabaceae)-Kenanga; Piper
methysticum Forst.(Piperaceae)-Kava-kava