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ALKALOIDS

INTRODUCTION

Alkaloids are naturally occurring chemical compounds containing at least one basic
nitrogen atoms in their structure. The word alkaloid is derives from the word alkaline which
was used to describe any nitrogen containing base. Alkaloids are produced by a large variety
of organisms, including bacteria, fungi, plants, and animals which are part of the group of
natural products. Many alkaloids can be purified from crude extracts by acid base
extraction. Many alkaloids are toxic to other organisms. They often have pharmacological
effects and are used as medications, as recreational drugs, or in entheogenic rituals. Some
alkaloids have a bitter taste. The classification of the alkaloids is complex and may be guided
by a set of rules that take into account the structure and other chemical features of the
alkaloid molecule, its biological origin, as well as the biogenetic origin where known. In
plant, alkaloids are generally exists as salts of organic acids, glycosides or sugar. Different
solvent are used to separate alkaloids into different classes and closely related product [7].

Piperine is one of the alkaloids which were classified as piperidine group [4]. Piperine
(C17H19NO3) is an alkaloid found in the fruits and roots of Piper nigrum and Piper longum
(species of Piperaceae family) [5]. This alkaloid is responsible for the pungency of pepper. It
was first isolated from the fruits of Piper nigrum, the source plant of both the black and white
pepper grains [3]. Piperine helps to increase the effect of other nutrients, such as curcumin,
vitamin B6, beta-carotene and selenium. You may also benefit from piperine if you need help
in maintaining a healthy weight or are experiencing short-term stress. Additional reasons to
take piperine include breathing difficulties, problems with digestion, joint discomfort and low
moods [2].

Black and white pepper from Piper nigrum. Piper nigrum palnt with immature pepper corns
Picture taken from Google Image Picture taken by Google Image
Piperine is slightly soluble in water (40mg/L at 80 C) and more so in alcohol (1g/15mL),
ether (1g/36mL) or chloroform (1g/1.7mL) [6]. For extraction of piperine, the black pepper
are crushed into powder and dissolve into the solvent. The solution is filtered to obtain the
precipitate after Piperine is dissolved into the solvent. The precipitate is then left for
evaporation to obtain the mass of the piperine contain the black pepper.

Piperine is an alkaloid that gives black pepper (Piper nigrum) its flavor. Piperine has a
long history of use in some types of traditional medicine. Its primary commercial use is in
modern herbal medicine [2]. The amount of piperine in different parts of the plant are
different. In terms of commercial production, it is crucial to know which part of the piper
nigrum plant contains higher percentage of piperine.

The main objective of this research is to determine the percentage of piperine contain in
the fruits and roots of piper nigrum and compare its solubility in propan-2-ol and ether. We
hypothesize that the fruits of piper nigrum has higher contain of piperine compare to the roots
and it is more soluble in propan-2-ol compare to ether.

THEORY & LITERATURE REVIEW

Piperine is an alkaloid responsible for pungency of black pepper. It is a liphophillic


amide that is soluble in ethanol (ca. 1 g/15 mL) and isopropyl alcohol. It forms needle-like
shaped monoclinic crystals with m. p. 130 C. Ethanolic solutions of the compound have a
sharp taste whereas the crystalline compound is tasteless. Piperine acts as a very weak base
forming salt only with strong minerals acids such as hydrochloric acid (BHCl) or
hexachloroplatinic acid (BH2PtCl6). Dihydrochloride is unstable and spontaneously
decomposes. Piperine can be hydrolyzed with sodium hydroxide to another volatile base
piperidine. The acidic hydrolysis yields piperic acid thus it is confirmed that piperine is the
piperidine amide of piperic acid. Piperine can be extracted from P. nigrum (black pepper) and
also from P. longum (white pepper) and P. clusii (Aschanti). The piperine content in black
pepper varies from 6-9%.
PROBLEM STATEMENT

The phytochemical studies on pepper have been published since 2008. Twenty-two
compounds, mainly isoquinoline type alkaloids were reported on this species and nine known
compounds were isolated from the leaves of A. corneri. From the preliminary screening, the
seeds of this species have high content of alkaloids. Therefore, it is a potential plant for
extraction and isolation followed by structural elucidation of alkaloids especially the new
compound as reference in future.

OBJECTIVES

The objectives of this study are as follows:

i. To extract alkaloid from the seeds of pepper.

ii. To carry out the percentage of alkaloids in pepper.


METHODOLOGY

Preparation of the fruits & roots of piper nigrum (black pepper)


Black pepper is produced from the stillgreen, unripe drupes of the pepper plant. The still-
green, unripe drupes and the roots of the pepper plant from one of our friends garden before
the black pepper is produced.
1. The drupes are cooked briefly in hot water, both to clean them and to prepare them for
drying for 5 days.
2. The heat rupture the cells walls in the pepper, speeding the work of browning
enzymes during drying.
3. The drupes are dried in the sun, the pepper around the seeds shrink and darkened into
a thin, wrinkled black layer. It is called black peppercorn once dried.
4. The roots of the black pepper are also dried under the sun to remove the moisture of
the roots.
5. After the peppercorn and the root of the black pepper are dried, it is then crush into
powder form in order to dissolve in the solvent.
Solvent extraction of piperine
Material:
Ethanol , Black pepper powder, Alcoholic potassium hydroxide solution
Apparatus:
Beaker, Filter funnel, Conical flask

Procedure:

1. 10gm of black pepper powder extracted with 150ml ethanol in conical flask for 2
hours.
2. The solution was filtered and concentrated on the water bath at 70 until the
volume of the solution was reduced to 70ml.
3. 10ml alcoholic potassium hydroxide was added to the solution.
4. A resin that formed immediately after the addition was filtered off.
5. The filtered solution was then transfer into a beaker.
6. The beaker was let to crystallize in fume chamber.
7. Measure the powder left after evaporation with the electronic balance.
8. Calculate the percentage of the alkaloid content by using the formula:
INTERPRETATION/ OBSERVATION & DATA
Experiment Mass of empty Mass of beaker with
beaker (g) alkaloids (g)
1 100.30 100.97
2 100.29 100.97
3 100.31 100.98
Average 100.30 100.97

Mass of alkaloids = Mass of beaker with alkaloids - Mass of empty beaker


= 100.97g - 100.30g
= 0.67g

Percentage of alkaloids = (Mass of alkaloids Mass of raw material ) 100%


= (0.67g 10g) 100%
= 6.70 %

CONCLUSION
1. The percentage of alkaloids from pepper is 6.70 %.
2. The alkaloids present in the pepper is Piperine.

REFERENCES
1. Extraction of piperine from black pepper. Retrieved 1 February 2017 from
htpp://chem.piecesofscience.com/?p=465

2. Health Benefits and Uses of Piperine. Retrieved 16 January 2017 from


http://www.xtend-life.com/information/ingredients/piperine

3. K.Vasavirama, Mahesh Upender (2014) Piperine: A Valuable Alkaloid From Piper


Species, International Journal of Pharmacy and Pharmaceutical Sciences, Vol 6, Issue
4, 34-38.

4. Phar Macognogy (2012) Piperidine Alkaloids. Retrieved 21 January 2017 from


http//www. epharmacognosy.com/2012/07/piperidine-alkaloids.html.

5. Psychology (n.d) In Wikipedia. Retrieved 18 January 2017 from


https://en.wikipedia.org/wiki/Black_pepper.

6. Piperine molecule in Black Pepper. Retrieved 1 February 2017 from


http://www.scienceofcooking.com

7. What Is an Alkaloid? Classification of alkaloids. Retrieved 12 January 2017 from


http://www.plantscience4u.com/2013/02/what-is-alkaloid.html#.WJGSH_ArLIW.