NIM : RSA1C110010
MID TEST : NATURAL PRODUCT OF CHEMISTRY
2. jelaskan
bagaimana idenya suatu senyawa BAHAN alam Yang memiliki Potensi biologis
Tinggi, Dan Prospektif untuk kemaslahatan makhluk Hidup dapat disintesis di
labortorium!
3. Jelaskan kaidah-kaidah pokok dalam memilih
pelarut untuk isolasi dan purifikasi
suatu senyawa bahan alam. Berikan dengan contoh untuk 4 golongan senyawa bahan
alam : terpenoid, alkaloid, flavonoid dan steroid !
4. jelaskan dasar titik tolak penentuan struktur
suatu senyawa organic. Bila senyawa bahan alam tersebut adalah kafein misalnya.
Kemukakan gagasan anda tentang hal-hal pokok apa saja yang diperlukan untuk
menentukan struktur secara keseluruhan !
1.
Bioaktifvity by testing it and by doing some
research to synthesize these compounds. Reacting with other compounds that can
produce useful products. Isolation of Active Compounds example Efficacious
Cytotoxic Flavonoids from Leaves Kemuning (Murraya Panicullata L. Jack) 1 gram
fraction of methanol extract yellow leaves, flavonoids derived class of
flavones (apigenin) as light yellow crystals of yellow leaves with a melting
point (195-196o C). From the test results Brine Shrimp Lethality Test against
these compounds are not toxic effect on larvae of Artemia salina Leach with
LC50 194.786 ug / ml.
2.
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 lab,
in my opinion is a way to extract in vivo, such as tea leaf extract as a cancer
drug that can be useful to society. It can also be synthesized in the
laboratory to produce useful products.
For example, quercetin found in
parasites that developed as an anticancer agent:
Parasite plants that had only
known as weeds or parasitic on other plants as anticancer compounds known
abortion will then need to inform the general public of these properties.
Penginformasian in the community also needs to be accompanied by information on
how to utilize the parasite simply as a traditional or herbal medicine, both
its manufacture and its use.
With the data that the parasite
tea (Scurrula oortiana) has entered the list of candidates the opportunity
fitofarmaka other parasites are still one family with tea parasite to develop a
greater fitofarmaka such parasites mango (Dendrophthoe pentandra). It is
supported in terms of toxicity, where both parasites are relatively non-toxic.
In mango parasites obtained by false LD50 16, 0962 g / kg for mice (Khakim,
2000), LD50 of parasite tea> 5 g / kg bw (Winarno, 2000). When viewed from
kuersetinnya levels, the parasite is more promising as mango tea parasite
because fitofarmaka than quercetin levels of parasite mango of 39.8 mg / g higher
than the tea parasite levels reached only 9.6 mg / g (Rosidah, et al. , 1999).
With the content of quercetin are much larger than the parasite mango tea
parasite has its own economic value to be used as fitofarmaka.
Several studies have been
conducted on the parasite mango as a first step towards fitofarmaka include
phytochemical studies to identify the active compound content. From experiments
it is known that the parasite mango contains flavonoids quercetin,
meso-inositol, rutin, and tannins (Lestyorini, 2007). Test selectivity
sitotoksitas mango parasites showed that the concentration of 100 ppm both
ethanolic extracts and water extracts showed no cytotoxic to normal cells (cell
viability B16 <0%) (Artanti, et al., 2003). Acute toxicity test was not obtained
dose mango parasite that causes the death of test animals, so it can only be
found false LD50 for mice of 16.0962 g / kg (Khakim, 2000). Pharmacological
test showed that the parasite isolates mango flavonoids have inhibitory
activity of cancer growth in mice at a dose of 12.2 mg / ml (Sukardiman, 1999).
Pharmacological trials on potential, efficacy, as well as the activity of the
parasite mango quercetin has also been carried out in combination with
chemotherapeutic agents such as mentioned above.
Having conducted a series of
studies, the direction of parasite mango fitofarmaka clearer. However, to
realize the parasite mango as fitofarmaka still needed a long stride. Apart
from having to determine the formula, and the formula confirmation of identity,
must be carried out clinical trials on humans. As a traditional medicine that
will move towards phytopharmaca course required no small cost. The solution
offered is made mango parasite Standardized Herbal Medicines
(OHT) first. If this is done, then it will obviously give a positive value
for the development of fitofarmaka. Costs can be reduced in such a way as some
steps tests have been done, such as the standardization of the content and
clinical trials. In addition to the parasite as OHT maketh the publication of
the public about the benefits of the parasite can also be achieved.
3. Examples of the four classes
of compounds of natural ingredients:
a. flavonoids
For Flavonoids solvent used is
usually n-hexane, methanol. for non-polar flavonoids (eg, isoflavones,
flavanones, flavones and flavonols alcohol) was extracted using non-polar
solvents as well as chloroform, dichloromethane, diethyl ether, or ethyl
acetate. For example Isolation Efficacious Compounds Active Cytotoxic
Flavonoids from Leaves Kemuning (Murraya Panicullata Jack L.) using solvent
n-hexana
b. terpenoids
usually with the solvent
methanol. Election methanol solvent in this process because it has the
properties of materials that will easily dissolve in the solvent extract
Elections and methods appropriate for the purposes of isolation is absolutely
necessary, therefore the choice of solvent is used to determine the success in
isolation. Phenolic compounds are compounds that are polar and soluble in polar
and semipolar solvents, the research will be conducted using the solvent ethyl
acetate is polar. For example extracts ISOLATION OF COMPOUNDS terpenes Aglaia
odorata Lour SKIN STEM (Meliaceae) using the solvent ethyl acetate
c. alkaloids
usually use organic solvents such
as chloroform, ether, etc., eg flavonoids isolated with petroleum ether solvent
d. steroids
commonly used solvents are polar
and semi-polar, it can be used solvent ether or chloroform. Examples of steroid
compounds isolated from the bark of plants maja using the solvent n-hexana.
4. Before the beginning of the
structure determination of spectroscopic techniques are introduced, namely the
first half of the 20th century, the structure determination of organic
compounds based on a comparison with compounds whose structures are known. When
all the physical and chemical properties of compounds identical to compounds
that have been described in the literature, it can be concluded that the
compound under study is identical to the structure snyawa known. This criterion
was adopted until now although the comparison is done may be different. When
the physical and chemical properties of the investigated compounds are not
appropriate with any compound that are well known in the literature, the
possibility of this compound is a new compound, has never been synthesized or
has not been reported. In such cases, new problems may arise. How can one
determine the structure of an entirely new compound? The method for determining
the structure changed dramatically in the mid-20th century. Traditional method,
although simple, is very time consuming and difficult in practice: thus, the
first structure of a newly synthesized compound is assumed, and then a
particular route is designed to convert these compounds into compounds known.
Changing it may require several steps. Throughout the structural changes caused
by each identified stage, the successful conversion to a known compound is a
testament to the assumed structure. It should be added that the reaction to the
change of the selected reaction involves only the functional groups and not the
framework of the molecule.
Spectroscopic methods is a key
tool in modern chemistry for the identification of the molecular structure. In
organic chemistry, spectroscopic methods used to determine and confirm the
molecular structure, to monitor the reaction and to determine the purity of a
compound. The most important method for organic chemistry is a core magetik
resonance spectroscopy: 1H and 13C NMR spectroscopy, mass spectrometry,
infrared spectroscopy and UV / Vis.
example:
IDENTIFICATION OF COMPOUNDS terpenes extract Aglaia odorata Lour SKIN
STEM (Meliaceae)
Phase identification of the
isolated compounds
Determination of molecular
structure by sticher in [17] the determination of molecular structures obtained
through spectroscopic measurement steps to obtain spectral data. After
obtaining the spectral data of new molecular structures determined. The steps
were as follows:
1. To measure the UV-Vis spectra
to determine the chromophore groups
2. To measure the IR spectrum for
the presence of functional groups
3. To measure the mass spectra
(MS) to determine the fragmentation pattern of the compound.
Phase identification of compounds
identification isolat_I
Then on Isolat_I performed
include identification of chemical test, test and test physics spectroscopy.
Chemically test is performed using FeCl3 and Shinoda test. From the test
results it is known that chemical compounds are included into the Isolat_I
Phenolics. That is indicated by the color change to yellow.
While the identification through
a physical test conducted by examining the melting point Isolat_I. From the
test results using Electrothermal Melting Point Apparatus with repetition three
times, known melting point of isolates I, the 120-121oC, 120-121oC, 120-122oC.
From these measurements it can be seen that the measurement of the melting
point at the beginning and end of the show the differences that do not exceed
1.
In the UV-Vis spectroscopy test
the samples were dissolved in methanol obtained maximum absorption at = 278 and
338 nm
Test results on UV-Vis Isolat_I
known that maximum absorption at α = 278 and 338. Predictably a saturated
ketones and aldehydes. Saturated ketones and aldehydes showed a weak symmetry
forbidden bands at 275-295 nm, ε ~ 20, is the result of the excitation of
electrons to oxygen silent anti-bonding orbital of the carbonyl group. Ketones
and aldehydes substituted more strongly absorbed in the upper area. The
existence of weak bands in the 275-295 nm region is indicative of the carbonyl
group of ketones or aldehydes [12]. Ketone α, β-unsaturated show ribbons n
π * little stronger or a series of bands with ε ~ 100 at 300-500 nm. Transition
n π * α-diketon diketon form shows two bands, one in the region near 290
nm, ε ~ 30 and ε 10-30 second tape appeared on the visible region at 340-400
nm.
In IR spectroscopy tests,
measurements Infrared spectra (IR) were prepared by KBr pellet technique has
been shown in Figure 2. IR spectrum of the isolated compounds showed uptake in
the area of 772, 1219, 1650, 2854,
2922, 3435 cm-1. The tops of the show include: aromatic CC absorption of
860-680 cm-1 for the peak 772, uptake of CO 1260-1000 cm-1 for the top of 1219, then C = C aromatic
absorption at 1650 cm-1 peak, at the peak of the aliphatic CH 2854, and at the
height of 2922 showed strong CH absorption from 2850 to 2970, and the last in
3435 showed peak OH absorption at 3200-3600.
From the results of GC-MS
spectroscopy testing Isolat_I consists of 17 dominant peaks (Fig. 3), the
dominant peak of 17 was then carried out the mass spectrometry data retrieval
as much as 3% of the area that has a peak above 4.00% is the peak number 2, 3,
and 6 ..
From the top 2, unknown compounds
can be demonstrated in isolates I-stem molecular ion peak at m / z, namely:
147, 138, 123, 109, 96, 81, 67, 43, 41, 38 with the base peak at m / z 43. From
the results of the study of literature and to help chemoffice compounds with
peaks as mentioned meurpakan characteristic peaks at sesquiterpene compound
[13] that this compound is a compound suspected sesquiterpene epoxy type II
humulen molecular weight 220, can be seen in Figure 4. This compound underwent
termination of m / z 220 produced m / z 149 by releasing C5H11 `. Then proceed
with the loss of C2H2 and CH2 resulting fragment m / z 123 and 109. Further
loss of CO fragments m / z 81 (C6H9 +), the next result in fragment m / z 67
(C5H7 +) with CH2 and final disappearance of fragments m / z 41 (C3H5 +). While
at the height of 3, were found to have molecular ion peaks at m / z 205, 187,
177, 162, 147, 121, 107, 93, 79, 67, and a base peak at m / z 43. The compound
has a bicyclic sesquiterpenes fragmentation peaks at m / z 43, 55, 69, 81, 121,
133, 149, 191, 205 and 234 [M +] with a base peak at m / z 43 [14]. Several
studies cite leteratur isoprenoid compounds give m / z at 69 for isoprene, m /
z 137 for monoterpenes, and m / z 205 for sesquiterpene [15]. This compound has
a molecular weight of 205. From the literature study, this compound was found
in plants Ophiopogon snack Lodd At the top 6, it is known that compounds having
an breakdown fragment at m / z 279, 168, 167, 149, 132, 113, 104, 84, 71, 57,
41 and 39 , with a base peak at m / z 149. From the results of IR spectroscopy,
UV-Vis and GC-MS. Compounds Isolat_I with Mr = 279 is thought to be the
compound α-santalan-type sesquiterpene. It is based on the results of IR
spectroscopy Isolat_I alleged resemblance to the results of IR-santalan
compound α-sesquiterpene [16], can be seen in table 1. In the MS spectrum of
the peak Isolat_I no 6, shows that the m / z of 279 or Mr. Then from that
spectrum MS-sesquiterpene α-santalan also showed m / z or Mr at (279 [M +-CH3],
164, 121, 59). These compounds undergo chain termination epoxy and ether on one
side so as to produce m / z 167 (M +1- C4H7O + - C3H7 +, C11H19O +). Then
followed by the disappearance of the H2O fragment m / z 167 fragments stable at
m / z 149 (C11H17 +). Fragments generated when removing the epoxide and propyl
chain fragments m / z 71 (C4H7O +) and m / z 43 (C3H7 +). In the next fragment
solution if m / z 149 loses CH2 +2 H + will appear fragment m / z 132. This
compound has a molecular weight of 279.
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