Mid
Semester Exam
Subject : Natural Products Chemistry
Credit : 2 credits
Lecturer : Dr. Syamsurizal, M.Si
Day / Date : Saturday, 24 november 2012
Time : 15:30 till 09:00 am (26 november 2012)
Subject : Natural Products Chemistry
Credit : 2 credits
Lecturer : Dr. Syamsurizal, M.Si
Day / Date : Saturday, 24 november 2012
Time : 15:30 till 09:00 am (26 november 2012)
1.
Put forward
your ideas how to
convert a compound of natural ingredients that do not have the potential (inactive)
can be made into superior compounds that have a
high potential for biological
activity. Give the
example.
Answer:
compounds of natural ingredients that
have no potential (inactive) such as bagasse and rice husks or shells can be
made into activated carbon compounds.
Activated carbon is carbon with amorphous or microcrystalline structure
that the special treatment can have a surface area in a very
between the 300 - 2000 m2/gram. produced from materials containing carbon with warming
at high temperatures. As heating progresses, sought to avoid
warm indoor air leaks so that materials containing
Carbon is only carbonized and not teroksidasi.Pada There are basically two types of activated carbon are
liquid phase activated carbon produced from material with a low density,
such as rice husk charcoal granules form fragile and easily
destroyed, has a high ash content in the form of silica and is usually used
to eliminate the odor, taste, color and other organic contaminants,
while the gas-phase activated carbon produced from a material with a high density. Despite that its benefits have not been too concerned to biological problems.
addition compounds of natural ingredients that have no potemsi (inactive) his missal on mangosteen rind, but when the fruit is extracted, it can be in the womb extraordinary benefits contained in the mangosteen rind
Mangosteen rind and almost all parts of the plant containing mangosteen xanthone tree. Among the powerful phytonutrients found in the skin of the mangosteen, xanthones stand alone can provide benefits that are very impressive. Scientific studies show that the xanthone can promote wellness to the body functions. Xanthones are natural mangosteen rind, may help:
- Maintain intestinal health
- Supports the immune system
- Neutralize free radicals
- Support cartilage and joint function
- Promoting a healthy seasonal respiratory system
Researchers have identified dozens of biologically active xanthones in the mangosteen fruit. Today, researchers are just beginning to uncover the powerful scientific properties behind the mangosteen fruit.
What Xanthones?
Xanthones are a unique class of biologically active compounds with bioactive capability (such as antioxidant properties). A restricted group of plant polyphenols, biosynthetically related to the flavonoids.
Polyphenols are a group of plant chemical substances characterized by the presence of more than one phenolic group. Polyphenols are responsible for the color of some plants and are considered strong antioxidants with potential health benefits.
Flavonoids, more than 5,000 naturally occurring flavonoids have been characterized from
Activated carbon is carbon with amorphous or microcrystalline structure
that the special treatment can have a surface area in a very
between the 300 - 2000 m2/gram. produced from materials containing carbon with warming
at high temperatures. As heating progresses, sought to avoid
warm indoor air leaks so that materials containing
Carbon is only carbonized and not teroksidasi.Pada There are basically two types of activated carbon are
liquid phase activated carbon produced from material with a low density,
such as rice husk charcoal granules form fragile and easily
destroyed, has a high ash content in the form of silica and is usually used
to eliminate the odor, taste, color and other organic contaminants,
while the gas-phase activated carbon produced from a material with a high density. Despite that its benefits have not been too concerned to biological problems.
addition compounds of natural ingredients that have no potemsi (inactive) his missal on mangosteen rind, but when the fruit is extracted, it can be in the womb extraordinary benefits contained in the mangosteen rind
Mangosteen rind and almost all parts of the plant containing mangosteen xanthone tree. Among the powerful phytonutrients found in the skin of the mangosteen, xanthones stand alone can provide benefits that are very impressive. Scientific studies show that the xanthone can promote wellness to the body functions. Xanthones are natural mangosteen rind, may help:
- Maintain intestinal health
- Supports the immune system
- Neutralize free radicals
- Support cartilage and joint function
- Promoting a healthy seasonal respiratory system
Researchers have identified dozens of biologically active xanthones in the mangosteen fruit. Today, researchers are just beginning to uncover the powerful scientific properties behind the mangosteen fruit.
What Xanthones?
Xanthones are a unique class of biologically active compounds with bioactive capability (such as antioxidant properties). A restricted group of plant polyphenols, biosynthetically related to the flavonoids.
Polyphenols are a group of plant chemical substances characterized by the presence of more than one phenolic group. Polyphenols are responsible for the color of some plants and are considered strong antioxidants with potential health benefits.
Flavonoids, more than 5,000 naturally occurring flavonoids have been characterized from
various plants. The beneficial effects of plant foods that are often
associated with flavonoid compounds, rather than known nutrients, as they show
a variety of biological effects.
Planar-six carbon molecules in a conjugated ring system consisting of a backbone molecule and various chemical groups attached. The backbone consists of two benzene rings bridged through a carbonyl group and oxygen. Each ring is connected in a fused formation not allowing free rotation about the carbon-carbon bonds. This unique backbone along with type and position of the attached chemical groups define the specific function of the nature of xanthone.
Planar-six carbon molecules in a conjugated ring system consisting of a backbone molecule and various chemical groups attached. The backbone consists of two benzene rings bridged through a carbonyl group and oxygen. Each ring is connected in a fused formation not allowing free rotation about the carbon-carbon bonds. This unique backbone along with type and position of the attached chemical groups define the specific function of the nature of xanthone.
2.
Explain
how the idea of a
compound of natural ingredients that have a high biological
potency and prospective
for the benefit of sentient beings
can be synthesized in the laboratory.
Jawab:
A compound
of natural ingredients that have a high biological potency and prospective for kemaslatan
living things: in compound bibenzil
bibenzil compounds that have biological activity, and availability is limited in nature, then
need to synthesize compounds bibenzil the starting materials are easily available, inexpensive, and easy method performed in the laboratory.
Compounds bibenzil (dihidrostilbena) is an important natural ingredient products and
attract attention, this is caused by biological activity possessed. A number of compounds
bibenzil reported to have antimitotic activity, antileukimia, and is being done
research use bibenzil compounds as cytotoxic agents in cancer cells (Wang, et al.,
2004: 467)
The presence of compounds bibenzil very limited in nature. Because the compounds have bibenzil
important biological activities, the procurement efforts of the synthesis of compounds bibenzil
developed in the laboratory. Bibenzil compounds can be obtained from the catalytic hydrogenation reaction
stilbena compounds. Stilbena compound composed of two benzene rings connected to each other
bibenzil compounds that have biological activity, and availability is limited in nature, then
need to synthesize compounds bibenzil the starting materials are easily available, inexpensive, and easy method performed in the laboratory.
Compounds bibenzil (dihidrostilbena) is an important natural ingredient products and
attract attention, this is caused by biological activity possessed. A number of compounds
bibenzil reported to have antimitotic activity, antileukimia, and is being done
research use bibenzil compounds as cytotoxic agents in cancer cells (Wang, et al.,
2004: 467)
The presence of compounds bibenzil very limited in nature. Because the compounds have bibenzil
important biological activities, the procurement efforts of the synthesis of compounds bibenzil
developed in the laboratory. Bibenzil compounds can be obtained from the catalytic hydrogenation reaction
stilbena compounds. Stilbena compound composed of two benzene rings connected to each other
by group C = C olefinic (alkene). Alkene compounds
can be synthesized through Wittig reaction
using carbonyl compounds and phosphonium Ilida.
using carbonyl compounds and phosphonium Ilida.
Contains
vanillin aldehyde carbonyl functional groups that may be subject to Wittig
reaction. Phosphonium Ilida can be made through
the substitution reaction
nucleophilic (SN2) of a tertiary alkyl halides with Phosphine. In the synthesis of the alkyl compounds stilbena
halides can be used are benzylic alkyl halides. Vanillin can be converted into alkyl compounds
benzylic halides. Vanillin first reduced with reducing agents such as LiAlH4 in THF, will
vanilil alcohol derived compounds, further substitution reactions with PBr3 in CH2Cl2,
will be obtained vanilil bromide compounds. Vanilil bromide when treated with
triphenylphosphine be obtained phosphonium salt, which is a phosphonium salt when reacted with
strong bases such as n-butyl lithium, sodium amide or sodium hydride compounds will be obtained
phosphonium Ilida. Carbon negative on subsequent Ilida can attack the carbonyl group of compounds
vanillin. Adduct between Ilida with vanillin was a betaine. Betaine then undergoes
cyclization and elimination of triphenylphosphine, and will get stilbena substituted compounds. when
stilbena substituted compounds are catalytic hydrogenation reactions, you will get a compound
bibenzil.
nucleophilic (SN2) of a tertiary alkyl halides with Phosphine. In the synthesis of the alkyl compounds stilbena
halides can be used are benzylic alkyl halides. Vanillin can be converted into alkyl compounds
benzylic halides. Vanillin first reduced with reducing agents such as LiAlH4 in THF, will
vanilil alcohol derived compounds, further substitution reactions with PBr3 in CH2Cl2,
will be obtained vanilil bromide compounds. Vanilil bromide when treated with
triphenylphosphine be obtained phosphonium salt, which is a phosphonium salt when reacted with
strong bases such as n-butyl lithium, sodium amide or sodium hydride compounds will be obtained
phosphonium Ilida. Carbon negative on subsequent Ilida can attack the carbonyl group of compounds
vanillin. Adduct between Ilida with vanillin was a betaine. Betaine then undergoes
cyclization and elimination of triphenylphosphine, and will get stilbena substituted compounds. when
stilbena substituted compounds are catalytic hydrogenation reactions, you will get a compound
bibenzil.
3.
Explain the basic rules in choosing a
solvent for the isolation and purification of a compound of natural
ingredients. Give the example for 4 classes of compounds of natural products:
terpenoids, alkaloids, flavonoids, and steroids.
Answer:
Basic
rules in choosing a solvent for the isolation and purification of a compound
ingredient is a natural solvent that meets the following requirements:
a.
Dissolves perfect solvent component of the natural compound material contained
in plants.
b.
Having a low boiling point solvents.
c.
solvents are mixed with water and the liquid extracted.
d.
Inert, does not react with the components of a compound of natural ingredients.
e.
Having the solvent boiling point, when evaporated leaving no residue.
f.
solvents at low cost or easy it can be.
g.
expected non-flammable solvent.
h.
Easy to separate the solvent from the solute
i. solvent according to the compound to be in
isolation (polar or non-polar)
the example from 4
classes compounds of natural product: alkaloid, terpenoid, flavonoid, and
steroid:
v Isolation
of
alkaloids from plant
roots Anamirta cocculus (L.) W. & A. (Tuba seeds) done by continuous extraction
using ethanol solvent
v Isolation
terpenoid compounds in herbs meniran
using solvent n-hexane and methanol.
v Isolation
from the roots and
stems of plants Fragrant Root (Polygala paniculata
L.) flavonoids extracted
by maceration using solvents methanol, and
fractionated by solvent n-hexane and ethyl acetate.
v isolation
of
steroids from the leaves of Mimosa Invisa by
maceration method using n-hexane solvent
4.
Explain the basic starting point for the
determination of the structure of an organic compound. When the compounds of
natural ingredients such as caffeine tersebuat is. Put forward your ideas
matter - whatever the subject matter is required in determining the overall
structure.
Answer:
Analysis of these
compounds usually involves the use of
of various
high-performance liquid chromatography (HPLC)
systems with a
detection range of absorbance or diode with each
The system is designed
for the separation of only a limited number of
many phenolic
components in tea (3, 14-19). There are several
studies in which both
flavan-3-ols and flavonol profiles
in tea have been
examined simultaneously and in depth (20).
Current paper describes
two resolutions, high gradient elution
reverse-phased HPLC
separation systems for more than 30
flavonols, flavan-3-ols
and related compounds in green tea and black, and their identification with
diode array detection and
electrospray mass
spectrometry (MS) using an ion trap instrument
with MSN facilities.
Gradient elution two
systems
used for reversed-phase
HPLC analysis of phenolics in tea
infusion. Although most
studies reported in the literature to make
the use of a single
long gradient, this approach can lead to
complete resolution of
some phenolic components with
small peaks are often
covered by more prominent component
that the elution
nearby. To solve this problem, two 60 min gradient
used as follows: 4-25%
acetonitrile gradient optimized
to separate catechins,
gallocatechins and gallate ester, and
10-30% acetonitrile
gradient was designed to address the flavonol
conjugation and
theaflavins. HPLC absorbance traces
obtained when the
gradient is used to analyze and green
black tea is
illustrated in Figures 1 and 2.
During HPLC
analysis, and
quantitative estimates of individual phenolic
purine alkaloids in green
and black tea infusions are
obtained from the
response of the diode array detector while
identity and purity of
the peaks was determined by analysis MSN
However, this would
involve not only extensive sample
purification but also a
requirement for some orders
magnitude more than the
amount of analyte low nanogram
needed for HPLC-MSN
and, as a result, will
very time consuming and
are not suitable approaches
for routine
quantitative analysis.
