SEMESTER
FINAL EXAM MATERIALS CHEMISTRY CULTURE
Name : Yunita Rubi Lestari
NIM : RSA1C110007
Course : Chemistry of Natural Product
Credits : 2
Lecturer : Dr. Syamsurizal, M.Si
Time : 22-29 December 2012
1).
Jelaskan dalam jalur biosintesis triterpenoid, identifikasilah faktor-faktor
penting yang sangat menentukan dihasilkannya triterpenoid dalam kuantitas yang
banyak.
Answer :
Triterpenoid
Triterpenoid carbon skeleton is a compound derived from the six units (units) and in the biosynthesis of isoprene derived from C30 acyclic hydrocarbons, ie skualena.
More than 4000 kinds of triterpenoids have been isolated with more than 40 kinds of basic framework that has been known and in principle is the cyclization of skualen. This compound is a compound colorless, crystalline, often high melting point and active optics.
Triterpenoid carbon skeleton is a compound derived from the six units (units) and in the biosynthesis of isoprene derived from C30 acyclic hydrocarbons, ie skualena.
More than 4000 kinds of triterpenoids have been isolated with more than 40 kinds of basic framework that has been known and in principle is the cyclization of skualen. This compound is a compound colorless, crystalline, often high melting point and active optics.
Triterpenoids
consisting of frame with 3 cyclic 6 which joined berupaka cyclic 5 or 6, which
has a cyclic 4 functional groups on specific cyclic. While
naming further simplified by giving the numbering on each carbon atom, thus
facilitating the determination of the substituents on each carbon atom. Terpenoida
a wide range of structures that arise as a result of subsequent secondary
reactions such as hydrolysis, isomerization, oxidation, reduction and
cyclization over-geranil, farnesil-and-geranil geranil pyrophosphate.
Triterpenoid
widespread in resin, cork and kutin plants. Resin
is a triterpenoid acid often together with xanthan gum polysaccharide in amber.
Triterpenoid
alcohol also are free and as glycosides. Triterpenoid
acyclic hydrocarbons skualena important only for the first time isolated from
shark liver oil but is also found in some nights epikutikula and vegetable oil
(olive oil). Triterpenoid
compound best known as lanosterol contained in wool grease, yeast and some
compounds of higher plants. Triterpenoid
eufol tetrasiklik like alcohol and acids from Euphorbia sp of Elemi Canarium
commune.
Triterpenoids
are pentacyclic triterpenoid most important thing. These compounds are found
in seprimitif sphagnum plants but the most common is the seed plants, free and glycosides. Triterpenoid nonglikosida often found as excretion and the work as a protective cuticle or cause resistance to water.
Several kinds of physiological activity of triterpenoids which is the active component of the plant has been used as a medicinal plant remedy diabetes, menstrual disorders, pecks snake, skin disorders, liver damage, and malaria.
Skualena is a steroid derivative of the basic framework has four rings as follows:
Triterpenoids have a very bitter taste, especially present in Rutaceae plants, Meliceae and Simaroubeaceae as limonin in citrus fruits (also classified as a sense of bitter alkaloids) and kukurbitasin D in Cucurbitaceae plants and diosgonin. In the form of triterpenoids found in plant sap of Euphorbia and Havea.
in seprimitif sphagnum plants but the most common is the seed plants, free and glycosides. Triterpenoid nonglikosida often found as excretion and the work as a protective cuticle or cause resistance to water.
Several kinds of physiological activity of triterpenoids which is the active component of the plant has been used as a medicinal plant remedy diabetes, menstrual disorders, pecks snake, skin disorders, liver damage, and malaria.
Skualena is a steroid derivative of the basic framework has four rings as follows:
Triterpenoids have a very bitter taste, especially present in Rutaceae plants, Meliceae and Simaroubeaceae as limonin in citrus fruits (also classified as a sense of bitter alkaloids) and kukurbitasin D in Cucurbitaceae plants and diosgonin. In the form of triterpenoids found in plant sap of Euphorbia and Havea.
Triterpenoid
Biosynthetic
Based on its mechanism of acetyl-CoA
via the mevalonic acid pathway produces isopentyl
pyrophosphate (IPP), which later became dimethyl
berisomerisasi alipirofosfat (DMPP) assisted with the isomerase enzyme, which
produces IPP and
DMPP join geranil
Pyrophosphate (GPP) to form monoterpenoid compounds,
then GPP and
IPP merged by the
same mechanism produces farnesil
pyrophosphate (FPP) to form sesquiterpenoid compound, combined with
the subsequent FPP FPP with a path similar
mechanisms will produce triterpenoid
compounds. In this
biosynthetic pathway could be modified to
increase the amount of production triterpenoid more and with
less time.
One of the factors that determine the quantity produced triterpenoid much on triterpenoid biosynthetic pathway enzymes. The enzyme in the biosynthesis of triterpenoids may also determine the amount that will be generated. This is because the growing number of enzymes that act on biosynthetic pathways, it will be the more triterpenoid obtained. The use of enzymes in the biosynthesis of the triterpenoids itself as a catalyst. Where it is known that the function of the use of enzymes that can accelerate the reaction, but did not participate react. But in this biosynthetic pathway inhibition also occurred that would lead to mevalonic triterpenoids produced a little.
One of the factors that determine the quantity produced triterpenoid much on triterpenoid biosynthetic pathway enzymes. The enzyme in the biosynthesis of triterpenoids may also determine the amount that will be generated. This is because the growing number of enzymes that act on biosynthetic pathways, it will be the more triterpenoid obtained. The use of enzymes in the biosynthesis of the triterpenoids itself as a catalyst. Where it is known that the function of the use of enzymes that can accelerate the reaction, but did not participate react. But in this biosynthetic pathway inhibition also occurred that would lead to mevalonic triterpenoids produced a little.
2).
Jelaskan dalam penentuan struktur flavonoid, kekhasan signal dan intensitas
serapan dengan menggunakan spektrum IR dan NMR. Berikan dengan contoh
sekurang-kurangnya dua struktur yang berbeda.
Answer :
Flavonoids are a group of
phenolic compounds found in fruits and vegetables.
Compound has 15 carbon atoms, consists of two substituted
benzene rings connected
by a single aliphatic chain
containing three carbon atoms (Figure 1.7). The basic
framework of the system structure
of flavonoids is C6-C3-C6.
Figure 1.7. structure of Flavonoids
Flavonoids have been studied have a wide range of biological activity.
Flavonoids act as anticancer, antiviral, anti-inflammatory,
reducing the risk of cardiovascular
disease and play a role in the
capture of free radicals. The
power of the antioxidant activity of flavonoids depends
on the number and position of OH groups contained
in the molecule. The more substitutes a hydroxy group on the flavonoid, the greater
the activity antiradikalnya.
The existence of ortho-catechol group (3'4'-OH) on the B ring
of flavonoids is an important
determinant of high antioxidant
capacity (Andersen et al., 2006).
• The intensity of the IR absorption:
In the long-wave infrared
spectrophotometry and wave number is the value used to indicate the position of the absorption spectrum.
Where in the intensity of the absorption of flavonoids is displayed hydroxyl (3227 cm-1) and (1628 cm-1).
Where in the intensity of the absorption of flavonoids is displayed hydroxyl (3227 cm-1) and (1628 cm-1).
• The intensity of the NMR absorption spectrum:
Samples under appropriate conditions flavonoids can adsorbing
area radio frequency electromagnetic radiation, radio depends on
the nature of the sample. A plot of peak frequency versus absorption
peak intensity gives an NMR spectrum
3). Dalam
isolasi alkaloid, pada tahap awal dibutuhkan kondisi asam atau basa. Jelaskan
dasar penggunaan reagen tersebut, dan berikan contohnya sekurang-kurangnya tiga
macam alkaloid.
Alkaloid is an alkaline compound containing nitrogen
atoms satuatau more and usually a cyclical system. Alkaloids
mengandungatom carbon, hydrogen, nitrogen, and usually contains many alkaloids
oksigen.Senyawa contained in the roots, seeds, wood and leaves daritumbuhan and
also of animals. Metabolismedari
alkaloid compounds is the result of plant and used as a backup for the
synthesis of the plant alkaloid protein.Kegunaan is as protective of pests,
plants and regulator amplifier hormones work. Alkaloids have physiological
effects. Source
is a flowering plant alkaloid, angiosperms, animals, insects, marine organisms
and microorganisms. Mengandungalkaloid
plant families that are Liliaceae, solanaceae, Rubiaceae, and papaveraceae
(Tobing, 1989).
Classification
of Alkaloids
Alkaloids not have a systematic name, so namadinyatakan as
trivial as codeine, morphine, heroin, quinine, kofein, nicotine. Almost
all were given the trivial name suffix-in that characterizes alkaloid.Sistem
alkaloid widely accepted classification is the division alkaloidmenjadi three
groups, namely real alkaloid, protoalkaloid and pseudoalkaloid.Suatu ways of
classifying alkaloid is a nitrogen based heterocyclic jeniscincin which is part
of the structure molekul.Jenisnya namely
pyrrolidine, piperidine, quinoline, isokuinolin, indole, pyridine dansebagainya
(Robinson, 1995). The structure of
the types of alkaloids presented dalamgambar
Isolation
of Alkaloids
a. Alkaloid extracted from the leaves of plants, flowers,
fruit, bark, dried and crushed danakar. Extraction
of alkaloids in umumadalah as follows:
Alkaloid extracted with certain solvents, such as ethanol, and then evaporated.
Alkaloid extracted with certain solvents, such as ethanol, and then evaporated.
b. Ekstrak obtained given inorganic acids to produce a
quaternary garamamonium then extracted again quaternary ammonium
c. Garam obtained reacted with natriumkarbonat to produce
these alkaloids kemudiandiekstraksi free with certain solvents such as ether
and chloroform.
d. Campuran - a mixture of alkaloids obtained finally
separated in various ways, such as chromatographic methods (Tobing, 1989).
There are other ways to get the
alkaloids from the
acid solution by absorption using Lloyd reagent,
and then eluted with
basaencer alkaloids. Alkaloid that is
hydrophobic absorbed by XAD-2 resin and dielusidengan acid or ethanol-water mixture. Many
alkaloids which can
be precipitated by Mayer's
reagent (potassium mercury (II) iodide)
or salt Reineccke. This study used a general
way that the
isolation of alkaloids extracted
with an organic solvent, acidification,
formation of quaternary garamamonium with a base, extraction with organic solvents, and purification using
column chromatography, thin layer chromatography, ataupuninstrumen-electronic instruments (IR, GC-MS, UV -Vis)
4).
Jelaskan keterkaitan diantara biosintesis, metode isolasi dan penentuan
struktur senyawa bahan alam . Berikan contohnya.
Answer :
Biosynthesis (also called biogenesis or
"anabolism") is an enzyme-catalyzed process in cells of living
organisms in which a substrate is converted to more complex products. Biosynthesis
process often consists of several enzymatic steps in which the product of one
step is used as substrate in the following step. An
example for such a multi-step biosynthetic pathways are those for the
production of amino acids, fatty acids, and natural products. Biosynthesis
plays a major role in all cells, and more specifically the metabolic routes
combined constitute general metabolism. Six organelles
within cells that is involved in biosynthesis. Ribosomes,
chloroplasts, smooth endoplasmic reticulum, rough endoplasmic reticulum,
plastids, and Golgi bodies
Basically isolation of chemical compounds from natural
ingredients it is a business how to separate the compounds were mixed so that
we can produce a pure single senayawa. Let's
take just one example, how to isolate compounds from plants. Plants
that contain thousands of compounds, both of which are categorized as primary
metabolites or secondary metabolites. Usually
the isolation of compounds from natural ingredients ni hopes to isolate
secondary metabolites, secondary metabolites due believed and has been shown to
provide benefits for human life. Antaralain
benefits are in the areas of agriculture, health, food, cosmetics etc.
NMR (Nuclear Magnetic Resonance) spectroscopy is a method
that is very important in determining the structure of organic compounds. We
know that all organic compounds metabolite natural products and bioactive both
lacked the NMR, both 1H-and 13C-NMR were expressed by a number of resonance
peaks and prices dimiliki.setiap NMR chemical shifts of carbon atoms in the
molecule has a peak or a shift NMR
chemical which depends on the position of the carbon atoms in the structure of
the molecule. The
position of the carbon atom gives specific conditions that lead to each carbon
atom in an organic molecule has a peak or specific NMR chemical shifts as well.
Trait
that would distinguish one molecule with another molecule. The
number of peaks and NMR price is used as the basis for the determination of a
molecule.
Biosynthesis, isolation and
structure determination methods that
are important to know and mempelajasi compounds
of natural ingredients. The third method is highly
related to one another. In the process
of biosynthesis of us can know the process of formation of compounds of natural ingredients that only lasted in living things. Where in this process we mangetahui that there are certain enzymes that are involved. In
the biosynthesis of these different types of reactions occur to produce a compound.
By studying the biosynthesis
of these compounds produced
as well, then we can know the properties of these compounds are natural materials, so
we can design an isolation
method based on the nature and
reactions of these compounds. For
example, we can choose a suitable solvent and other treatments
to obtain pure
substances. Once isolated,
then the knowledge-knowledge that has been known in advance,
we can carry out
the procedure of determining the structure of the compound, for example by spektoskopi NMR, IR and UV.