ISOLASI DAN IDENTIFIKASI

FENOL DAN POLIFENOL

(FENOL, FLAVONOID, KUMARIN,
TANIN)
 PENDAHULUAN
± 8000 Jenis senyawa fenol tanaman
Fenol sederhana dg 1 cincin aromatik, BM
rendah
Fenol komplek atau polifenol
Umumnya ditemukan di alam dalam bentuk
berkonjugasi dengan gula atau asam organik
 Biosynthesis of phenolics
Shikimic acid pathway is most common in plants. Converts simple
carbohydrates into aromatic amino acids. Not present in animals.
 Most plant phenolics are derived from cinnamic acid
formed from phenylalanine by phenylalanine ammonia lyase (PAL) enzyme.

PAL activity is inducible: fungal infection, low nutrient levels, high light

PAL
 KLASIFIKASI
• 1. SENYAWA FLAVONOID
• 2. SENYAWA NON FLAVONOID
 TIPE UTAMA SENYAWA FENOLIK
1. FENOL SEDERHANA - KUMARIN
2. LIGNIN
3. FLAVONOID – 2 cincin aromatik
anthocyanins, flavones/flavonols
4. TANIN TERKONDENSASI : polimer flavonoid
5. TANIN TERHIDROLISIS :
fenol + gula
BM lebih kecil dari tanin terkondensasi
1. simple phenolics

Fig. 13.10
Involved in
defense against
insect herbivores
and fungi, some may
have allelopathic
function.
 Simple phenolics

Caffeic acid
& ferulic acid
implicated in
allelopathy.

Fig. 13.11 Psoralen is one

of several
phototoxic
furanocoumarins,
(UV activated)
Simple phenolics

Fig. 13.11
 2. Lignin
Second most abundant compound in plants.

Highly branched polymer of phenylpropanoid groups (benzene-C3)

- often found in vessel elements, tracheids,
and stems; confers structural support.
Primary structural
role!

- Secondary role as a herbivore deterrent by

reducing digestibility of plant matter

- also difficult for microbes to degrade; its

presence slows litter decomposition.
 SIMPLE PHENOL
The phenolic compounds in this
group often also possess
alcoholic, aldehydic and
carboxylic acid groups; they
include eugenol (a phenolic
phenylpropane), vanillin (a
phenolic aldehyde) and various
phenolic acids, such as salicylic,
ferulic and caffeic acids.
POLY PHENOL

Stilbene diphenilethylene
PHYSICAL & CHEMICAL PROPERTIES

Stable
Volatile
unstable
Simple
phenols
Stable
Non
volatile
Unstable
PHYSICAL & CHEMICAL PROPERTIES

Hot
Stable
Poly extraction
phenols Cold
unstable
extraction
 POLARITY

Free Non polar

Phenols
Glycoside Polar
 IDENTIFICATION

Phenol Aglicon &

hydrolized
glycoside glicon

Aglicon
• FeCl3 ---- green or blue
• UV254 --- quenching, both simple phenol & polyphenol
• UV 365 --- Fluoresence, all polyphenol.
Glycon : KMnO4 ---- white with a purple blackground (TLC)
 TUGAS
1 kelas dibagi menjadi 8 kelompok sesuai urut
absen.
Tugas kelompok: membuat makalah dan PPT
Tugas individu : materi yang diberikan ke tugas
kelompok (MS word, topik---uraian, daftar
pustaka)
PPT dipresentasikan mgu depan (pertemuan ke
7)
 TOPIK
KEL SENYAWA POIN YG DIBAHAS
1 Thymol 1. Struktur
2. Tanaman penghasil
2 Eugenol 3. Khasiat / kegunaan
3 4. Sifat fisika kimia senyawa
Coumarin 5. Cara ekstraksi (pelarut dan metode ekstraksi)
4 Emodin 6. Fraksinasi dan isolasinya
7. Identifikasi dengan uji tabung
5 Lawson 8. Identifikasi dengan KLT dan kromatogramnya
6 9. Pustaka
EGCG
7 Rutin
8 Mangiferin
 Reference
• Trease and Evans, 2009, Pharmacognosy.
• Shah B and Seth, A.K., 2010, Text Book of
Pharmacognosy and Phytochemistry.
• Wagner and Bladt, 1999, Plant Drug Analysis.