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Metabolit Sekunder
Tim Toksikologi dan Tanaman Obat
FKH UB 2020
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Kompetensi
•Memahami dan menjelaskan tentang metabolit sekunder
Terpenoid Fenolik (Asam fenolat Flavonoid tanin kumarin) Senyawa mengandung nitrogen (Alkaloid)
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METABOLISME
Metabolisme → modifikasi senyawa kimia secara biokimia di dalam organisme dan sel. Metabolisme mencakup sintesis (anabolisme) dan
penguraian (katabolisme) molekul organik kompleks.
Metabolisme biasanya terdiri atas tahapan-tahapan yang melibatkan enzim, yang dikenal pula sebagai jalur metabolisme.
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METABOLISME
Metabolisme total merupakan semua proses biokimia di dalam organisme. Metabolisme sel mencakup semua proses kimia di dalam sel. Tanpa metabolisme, makhluk hidup tidak dapat bertahan hidup.
Produk metabolisme disebut metabolit
Metabolomika : Cabang biologi yang mempelajari komposisi metabolit secara keseluruhan pada suatu tahap perkembangan atau pada suatu bagian tubuh.
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Produk Metabolisme
Urutan terjadinya
• Metabolit primer
• Metabolit sekunder
• Metabolit intermediet
Efek yang timbul
• Zat aktif Farmasetik
• Zat aktif Farmakologik
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Produk Metabolisme
Isolasinya
•Zat aktif
•Zat inert
Status keberadaan
•Genuine
•Artefak
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• Diproduksi untuk menunjang
kehidupan namun tidak vital
• Memiliki aktivitas farmakologi
dan biologi
• Contoh : terpenoid, alkaloid,
flavonoid
Metabolit sekunder
• Esensial untuk hidup : pertumbuhan
normal, perkembangan dan reproduksi
• Berupa enzim fisiologis, menghasilkan
energi misal karbohidrat
• Terlibat langsung dalam fungsi fisiologis
normal : protein dan enzim
• Terdapat di dalam organisme atau sel
• Contoh : glukosa, asam organik
sederhana, asam lemak, protein,
hormon dan enzim
Berdasarkan pembentukan
Metabolit primer
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Berdasarkan sifat
•Zat Aktif oSuatu senyawa kimiawi yang terdapat di dalam suatu
sumber alami (umumnya tumbuhan) yang memberikan sifat khusus dan karakteristik dari tanaman sumber tersebut.
•Zat Inert oZat yang tidak bereaksi secara kimiawi
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Biosintesis Metabolit Sekunder
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•Metabolit sekunder dibentuk melalui jalur sintetis termodifikasi dari metabolit primer, atau dibagi substrat yang berasal dari metabolit primer
• Biosintesis metabolit sekunder sangat beragam tergantung dari goIongan senyawa yang bersangkutan.
• Jalur yang biasanya dilalui dalam pembentukan metabolit sekunder ada tiga jalur, yaitu jalur asam asetat, jalur asam sikimat, dan jalur asam mevalonat.
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(Wink, 2010)
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13 (Wink, 2010)
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Biosyntethic Pathway
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Pentosa
• Glikosida, polisakarida
Asam shikimat
• fenol, tanin, alkaloid aromatik
Asetat-malonat
• fenol dan alkaloid
Asam mevalonat
• terpena, steroid dan alkaloid
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Biosyntethic Pathway
•Penyadapan metabolit dari proses fotosintesis, glikolisis dan siklus Krebs yang merupakan proses menghasilkan energi, sehingga menyediakan zat intermediet untuk biosintesis metabolit sekunder. •Struktur penting yang digunakan dalam biosintesis
metabolit sekunder berasal dari asetil-KoA (Asetil koenzim A), asam shikimat, asam mevalonat dan 1-deoksilulosa 5-fosfat
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(Wink, 2010)
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Karakteristik Umum dan Peranan
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Karakteristik Umum :
•Metabolit sekunder bekerja sebagai pertahanan tanaman terhadap ancaman dari lingkungan maupun dari spesies lain.
• Tumbuhan telah berevolusi untuk beradaptasi lingkungan dengan pengkodean genetik dan beragam enzim yang bermanfaat untuk biosintesis metabolit sekunder.
• Tidak bersifat esensial untuk pertumbuhan atau metabolisme normal.
• Spesifik untuk genus, spesies bahkan strain tertentu.
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Peranan di Tanaman
1. Perlawanan terhadap fungi, amuba, tanaman, serangga, dan hewan
2. Agen transport metal
3. Agen simbiosis
4. Hormon reproduksi
5. Agen komunikasi antar organisme
6. Efektor diferensiasi (sporulasi dan germinasi spora)
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Peranan untuk Manusia
•Kesehatan (antibiotics, enzyme inhibitors, immunomodulators, agen antitumor, growth promoters of animals and plants)
•Nutrisi (pigments and nutraceuticals)
•Meningkatkan produktivitas pertanian (pesticida, insektisida, effectors of ecological competition and symbiosis and pheromones)
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Terpenes and Terpenoids
Phenols
Klasifikasi
Alkaloids
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TERPENOIDS
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Terpenes - class of >20,000 compounds containing carbon atoms in multiples of five
Terpenoids - oxygen-containing terpenes (alcohols, ketones, aldehydes)
(kereviz) (zencefil)
• The name "terpene" is derived from the word "turpentine“ • Terpenes and terpenoids are the primary constituents of
the essential oils of many types of plants and flowers.
rose oil 24
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The basic molecular formulae of terpenes are multiples of that, (C5H8)n where n is the number of linked isoprene -Isoprene - 2-methyl-1,3-butadiene- units. This is called the isoprene rule or the C5 rule.
Compounds containing carbon atoms in multiples of 5 suggest a C5 building block - isoprene units linked in a “head-to-tail” fashion
2-methyl-1,3-butadiene
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Klasifikasi Terpenoid berdasarkan jumlah unit isoprenol C5 pada strukturnya
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Finding the isoprene building block - cyclic compounds
Finding the isoprene building block - sesquiterpenes (C15)
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Finding the isoprene building block - triterpenes (C30) -
Squalene has a natural and vital part in the synthesis of all plant and animal sterols, including cholesterol, steroid hormones, and vitamin D in the human body
Finding the isoprene building block - tetraterpenes (C40)
• Lycopene is responsible for the red color in tomatoes and watermelon
• -carotene is the compound that causes carrots and apricots to be orange
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• Hemiterpenes consist of a single isoprene unit. Isoprene itself is
considered the only hemiterpene, but oxygen-containing derivatives are
hemiterpenoids such as prenol (found in citrus fruits, cranberry, grapes,
raspberry, blackberry, tomato, white bread) and isovaleric acid (found in
in essential oils).
• Monoterpenes consist of two isoprene units and have the molecular
formula C10H16. Examples of monoterpenes are: geraniol, limonene and
terpineol.
• Sesquiterpenes consist of three isoprene units and have the molecular
formula C15H24. Examples of sesquiterpenes are: humulene, farnesenes,
farnesol.
Prenol
isovaleric acid
limonene a strong smell of oranges
terpineol found in pine oil 29
humulene
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taxol used in cancer chemotherapy Taxadiene from enzymes Retinol is one of the forms of vitamin A
• Diterpenes are composed of four isoprene units and have the molecular formula C20H32.
• Examples are cafestol, kahweol, cembrene and taxadiene (precursor of taxol).
• Diterpenes also form the basis for biologically important compounds such as retinol, retinal, and phytol. – They are known to be antimicrobial and antiinflammatory.
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• Sesterterpenes, terpenes having 25 carbons and five isoprene units, are rare relative to the other sizes. – An example of a sesterterpene is geranylfarnesol.
• Triterpenes consist of six isoprene units and have the molecular
formula C30H48. – Squalene, the major constituent of shark liver oil.
• Tetraterpenes contain eight isoprene units and have the molecular
formula C40H64. – Biologically important tetraterpenes include the acyclic lycopene, the
monocyclic gamma-carotene, and the bicyclic alpha- and beta-carotenes.
• Polyterpenes consist of long chains of many isoprene units.
– Natural rubber consists of polyisoprene in which the double bonds are cis.
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Properti Terpenoids dan Aktivitas Farmakologisnya (Kabera et al., 2014)
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PHENOLICS
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PHENOLICS
• Group of secondary plant products or compounds • Composed of a hydroxyl group attached to an aromatic
ring • A broad range of compounds - found in all components
of plants: leaves, flowers, fruit etc • Function of most compounds is unknown • Comprised of many groups: Flavonoids, Tannins, Lignans
etc. – All very chemically diverse!
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Contoh:
• Senyawa fenol sederhana
• Lignan, Neolignan, Lignin
• Stilbena
• Naftokinon
• Antrakinon
• Flavonoid
• Antosianin
• Tanin
• Kumarin
• Kromon & Xanton
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• Lignans were identified in plants and later in biological fluids of mammals.
• As a class of compounds they contain a dibenzylbutane skeleton and in plants they aid in the formation of lignin used to construct the plant cell wall
LIGNANS
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TANNINS • Tannin a general name for a large group of complex
phenolic substances that are capable of tanning animal hides into leather by binding collagen
• Found in almost every plant part - abundant in unripe fruit
• Deter herbivores due to astringent properties - bind saliva and other digestive proteins
• Antimicrobial - tannins in heart wood prevent decay
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TANNINS
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Aktivitas Farmakologis Tannin
• Sebagai astringent terhadap diare
• Sebagai diuretik terhadap tumor lambung dan duodenum
• Antiinflamasi
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FLAVONOIDS • polyphenolic compounds with 15 Carbon
atoms, 2 benzene rings connected by a 3 carbon chain.
• Flower pigments in angiosperms (yellow, red, blue)
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Peranan Flavonoid
• Pada tanaman tongkat tinggi, flavonoid terlibat pada filtrasi UV, fiksasi nitrogen simbiosis, dan pigmen bunga.
• Selain itu juga bertindak sebagai chemical messengers, regulator fisiologis dan cell cycle inhibitor.
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1. Epidemiological studies: • reduced risk of cancer, coronary heart disease, and
osteoporosis
2. Biochemical and Pharmacological activities:
• anti-oxidant
• anti-viral • anti-carcinogenic • anti-inflammatory • anti-angiogenic • anti-estrogenic (estrogenic)
Studi Aktivitas Flavonoid
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44
Flavonoid Structure O
A
B
C
1
2
3
45
6
7
8 1'
2'
3'
4'
5'
6'
O
OH
A
B
C
1
2
5
6
7
8 1'
2'
3'
4'
5'
6'
O
O
A
B
C
1
2
3
5
6
7
8 1'
2'
3'
4'
5'
6'
O
O
A
B
C
1
2
5
6
7
8 1'
2'
3'
4'
5'
6'
O
O
OH
A
B
C
1
2
5
6
7
8 1'
2'
3'
4'
5'
6'
4
3
Base Structure
Flavanonol
Flavone
Flavanone
Flavonol
A
B
C
1
2
5
6
7
8
1'
2'
3'
4'
5'
6'
O
O
Isoflavone
O
O
OH
OH
OH
OH
OH
O
O
OH
OH
OH
OH
OH
O
O
OH
OH
OH
OH
O
O
OH
OH
OH
OH
OH
OH
Quercetin Taxifolin
Kaempferol Myricetin
O
O
OH
OH
OH
O
O
OH
OH
O
O
OH
OH
OH
OH
OH
O
O
OH
OH
OH
Baicalein Chrysin
Morin Galangin
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Flavonoids: source
Fruit and vegetables: (All classes)
Red wine: (Flavanol, Flavonols)
Cocoa: (Flavanols and procyanidins)
Tea: (Flavanols)
Berries: (Anthocyanins)
Citrus: (Flavanone)
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O
O
HO
OH
OCH3
BIOCHANIN A
O
O
HO
OH
OH
GENISTEIN
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ALKALOIDS
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Alkaloids
Definisi:
Alkaloid: “Alkali-like“
•Senyawa (basa) organik yang mengandung atom Nitrogen yang berasal dari asam amino (dan memiliki aktivitas farmakologis dalam kadar rendah)
•Most of them are toxic to other organisms
•Can be extracted by acid-base extraction
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Klasifikasi Alkaloids • True-alkaloid:
– Berasal dari asam amino
– Bersifat basa
– Atom N ada pada cincin heterosiklis
– Terdapat dalam bentuk garam dengan asam organik
– Contoh: atropin, morfin
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Pseudoalkaloid:
•Memiliki karakteristik seperti alkaloid tetapi tidak berasal dari asam amino
•Misal alkaloid terpen (aconitin: akaloid diterpen) dan alkaloid dari jalur metabolisme asetat (coniin), sifat kebasaan rendah
Klasifikasi Alkaloids
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• Protoalkaloid:
Amin sederhana dimana atom nitrogennya bukan merupakan bagian dari cincin heterosiklik, bersifat basa dan berasal dari asam amino, misal meskalin
Klasifikasi Alkaloids
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• Tidak semua senyawa yang mengandung atom N adalah alkaloid, contoh:
asam amino, piridin
• Kebasaan alkaloid berbeda-beda bahkan ada yang bersifat amfoterik misal chepalin dan asam, misal: kolkhisin
Fakta tentang Alkaloids
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• Umumnya merupakan campuran kompleks dari jalur biogenesis yang sama, yang didominasi salah satu konstituen
• Kandungan alkaloid dapat bervariasi pada tiap tahap pertumbuhan tumbuhan
• Alkaloid yang tidak mengandung oksigen dalam struktur kimianya biasanya pada suhu kamar bersifat cair (nikotin, koniin, spartein)
• Alkaloid yang mengandung oksigen akan berbentuk kristal, umumnya kristal tidak berwarna, pada kasus tertentu berwarna (berberine), beberapa berupa amorph
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• Alkaloid yang tidak mengandung oksigen dalam struktur kimianya biasanya pada suhu kamar bersifat cair (nikotin, koniin, spartein)
• Alkaloid yang mengandung oksigen akan berbentuk kristal, umumnya kristal tidak berwarna, pada kasus tertentu berwarna (berberine), beberapa berupa amorph
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Stereokimia: Sebagian besar optik aktif (biasanya levorotatori), kecuali yang termasuk gugus purin
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Kebasaan Tergantung pada keberadaan lone pair elektron dari atom N, tipe heterosiklis dan substitusinya Electron withdrawing group yang dekat dengan atom N menurunkan kebasaan Elektron donating group menaikkan kebasaan
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Kebasaan
•Piridin, kuinolin dan isokuinolin: basa •Pirolidin merupakan basa kuat •Pirol dan indol, bersifat asam
N N
N
NH
NH
NHNH
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•Alkaloid basa biasanya terdapat di tanaman dalam bentuk garam dengan asam mineral seperti HCl, H2SO4, HNO3, atau asam organik seperti asam tartrat, sulfamat dan maleat, mekonat, isobutirat dan benzoat, atau dalam kombinasi dengan tanin •Alkaloid yang non basa adalah alkaloid amida, ammonium kuartener, laktam, N-oxid
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A. Alkaloid heterosiklis yang berasal dari asam amino:
1. Ornithin
2. Lysine
3. Tirosin
4. Fenilalanin
5. Triptofan
6. Asam antranilat
7. Asam nikotinat
8. Histidin
Klasifikasi Alkaloids berdasarkan Biogenesis
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B. Alkaloid heterosiklis yang berasal dari nukleotid purin
C. Alkaloid yang terbentuk melalui transaminasi: terpenoid alkaloid
D. Alkaloid yang terbentuk melalui transaminasi dimana N atom terletak pada eksosiklis
Klasifikasi Alkaloids berdasarkan Biogenesis
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Aktivitas Biologis Alkaloids di Tanaman
• Plant growth regulatory activity – Menghambat pertumbuhan tanaman, misal
Tomatine pada tomat
– Aktivitas antimitotik : narciclassine dan narciprimine pada daffodil
• As phytoalexin (senyawa antimikroba) – Lupanine in Lupinus
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Aktivitas Farmakologis Alkaloids
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Seigler, D.S. 1998. Plant Secondary Metabolism.
Kabera, J.N., Semana, E., Mussa, A.R., He, X. 2014. Plant
Secondary Metabolites : Biosynthesis, Classification,
Function and Pharmacological Properties. Journal of
Pharmacy and Pharmacology; 2 : 377-392
Literature
Wink, M. 2010. Biochemistry of Plant Secondary
Metabolism