Deafness and Parenthood: A Case of Five Families in Addis Ababa

53 Pages·2007·0.64 MB·English

CHEMICAL COMPOSITION
OF
Humex abyssinicus Jacg.
.
A thesis
Presented to the
School of Graduate Studies
Addis Ababa University
In Partial fulfillment
of the recuirements of the Decree
Paster of Science in Chemistry
py
Alemu Bezabih
June 1982
J
TAgtEOT* CONSENTS
Acknowledgements
1
List of figures of illustration ii
List of Tables ii
iv
Abstract
1.0 Introduction 1
2.0 Back-ground 2
2.1 Anthraglucoside 2
2,11 Properties of anthraglucosides 3
2.2 Anthraciuinones 4
2.21 Nomenclature 4
2.22 Preparation 5
2.221 Oxidation of anthracene 5
2.222 From benzoic acid 5
2.223 From phthalic anhydride 6
2.224 From phthalic anhydride and
benzene 7
2.23 Chemical properties 7
2.231 Sulphonation 7
2.232 Nitration 8
2.233 Halogenation 8
2.234 Amidation 9
2.235 Hydroxylation 9
I
2.24 Spectral pronerties 12
2.241 Infrared snectra 12
2.242 uv spectra 15
2.243 Mass spectra 15
2.25 The Biosynthesis of anthraouinones 20
2.26 Isolation and characterization 23
3,0 Results and Biscussion 27
3.1 Extraction and fractionation of Rumex
abyssinicus 27
3.2 Characterization of compound A-4 28
3';3 Characterization of compound A-6 30
3.4 Characterization of compound A-7 43
4.0 Experimental 46
4.1 Column extraction of R. abyssinicus 46
4.2 Column chromate \phv of A-l 47
4.3 Column chroma \ A-3 48
,
...
4.4 Acetlation of c. 48
'/, (cid:127)' ;(cid:127) <'’4
- \h
t ,c ..;..7e;;mocr-: ':V
=
X
ACKNOWLEDGEMENTS
I wish to express my profound gratitude to my
research adviser Dr, Rerhanu Abegaz for sustained interest
and for his guidance, and encouragment during the course
of this investigation. I wish to express my sincere
appreciation to faculty staffs and fellow graduate
-
students at Addis Ababa University. Special thanks .no
.
given to Dr Ermias Danne for his helpful suggestion and
encouragement and Dr. Kleinpeter for the interrelation
13
of the C nmr spectra of the project. I would like to
. .
thank V/o Kongit Kebede who did the typing I am
; r ‘teful for the financial assistance from the Swedish
.
Agency for Research Co-operation with Developing Countries
(SAREC) obtained through the Ethiopian science and
Techneology -Commission and from Addis Ababa University
that was used to cover the expenses incurred in this
research and in the preparation of this thesis.
= ii =
LIST OF FIGURES
PAGE
FIGURE
1. Reaction souence of anthraciuinone
18
fragmentation
2. Illustration of Polvacetate rule 21
3. Fxtraction and fractionation of
of R. abyssinicus 28
4. Pass spectrum of A-4 50
5. nmr spectrum of A-4 51
6. Infrared spectrum of A-4 52
7. uv spectrum of A-4 53
8. Visible spectrum of A-4 54
9. 1'30 nmr spectrum of A-4 55
4
10. Pass spectrum of A-G 56
11. nmr spectrum of A-6 57
12. Infrared spectrum of A-G 58
13. uv spectrum of A-G 59
14. Visible spectrum of A-G GO
15. Mass spectrum of A-7 61
16. nmr spectrum of A-7 62
17. Infrared spectrum of A-7 63
18. uv spectrum of A-7 64
.
19. Visible spectrum of A-7 65
/
iV
ABSTRACT
Chemical Composition of
Rumex abyssinicus
by
Alemu Bezabih
.
Research Advisor: Dr Berhanu Abegaz
Rumex abyssinicus, family polygonaceae is a plant
.
used traditionally for colouring textiles and food It
has several medicinal application such as purgative, anti-
diabetic, and taencide. l'he powdered root of R abyssi-
0
nicus was packed on a column and extracted using acetone.
The sticky brownish mass(A-l)which was produced on
evaporation was further separated by column chromato-
graphy and showed to consist of anthraquinone derivatives
- - -
A 4, A 6 and A 7 which were latter identified as emodin
- -
(1,3,8 trihydroxy 6 methylanthraquinone), chrysopyanvl
(1,8 dihydroxyT3-methylanthraquinone, and physicone
(1,8 dihydroxy-3-methoxy-6-raethylanth-raquinone)respe-
.
ctively The structural ilucidation of emodin, chryso~
phanol and physicone are based on their ultraviolet,
visible, infrared, nuclear magnetic resonance and mass
.
spectras
INTRODUCTION
Filmex aUy^sinlQUs Jacq is atl indiaeneous v ild flowering
/
plant used traditionally tor colouring textiles and food. The
root of Rumex species has several medicinal applications. It
is used as taencide, purgative, antidiabetic, and as a cough
,
.1 2
remedy ’
On the genus Rumex, the following biological activities
have been reported. Extracts of roots and rhizomes of
.
R hydrolaphtlunf have bacteriostatic activity against
.
Staphylococeus ajbus, Staphytococus aures, and Bacillus subtile
R. acetosa and R. andreaeanus were found effective against
^
pathogenic fungi inclusing Trichophyton purpureum, T. gypseum
and T. granulosum. Antiseptic tannins and polyphenol components
which are both bacteriostatic and bacteriocidal to Elexner type
and other dysentry bacteria were isolated from R.confertus and
.
R feriicus . The roots of Rumex species' were used as laxatives,
but the presence of reduced aglycones in these plants causes
undesirable side effect, like vomiting and cramps. The extracts
of roots and rhizomes of R, alptnus* has 30# the purgative effect
of 1,8 dihydroxyanthraquinone. Substances With antioxidant
/
properties for fats, food and dyes were isolated from Rumex
^
species . Extract of R. confertus^ root is a heart stimulant
in frogs and mice and it is also a vasconstrictor to isolated
= 2
.
frogs, rabit and cat obgarts Asdobbic acid combihed with
^
polyphenols from Rumex species normalized the inbreased
activity of senittl ceriiioplashiift, decrease blood peroxidase and
cytochrome osidaSd activities and reduce liver glycogen level
which were caused by vitamin C and vitamin P dificiencies in
.
pigs
With regard to the chemical composition of Rumex
p
abysslnicus two compounds of oxalic acid' and chrysonhanic t
acid have been reported. However, for the Rumex1 1'IP- species \
flavonoids, ascorbic acid, carotenes, proteins, fats, cellulose\
)
free anthraquinone(chrysophanol, rheumemodin and rheochrysidin)
./
anthraglucosides(chrysophanein, rheochrysin, rheumemodin
glucoside), tannins and tannoglucosides were identified .
2.0 BACKGROUND
The genus Rumex is found to contain many
hydroxyanthraquinones, both unsubstituted and substituted.
These compounds occur both in the free state and as
*^
anthraglucosides'' .
2.1 ANTBRAOLUCOSIDE
The existanoe of anthraglucoside in plants, has been
known for more than a century and it occurs to a greater or
35
lesser extent in most parts of the plant .
35 3
2.11 PROPERTIES OF ANfrpnAGLflCOSIDfcS
.
Ahthraglucosides are optically active compounds w
which are readily hydrolysed by dilute mineral acids, dilute
alkali, or suitable enzyme. The naturally occur!nig'
anthraglucosides have the general structure shown in (1).
The glycosidic linkage is almdst invariable/rJ-witli a D-sugar
. .
and cMvith I-sugar
1
CHR
O
\
4 Cft(OH) H—C — 0 —-R2
\
CH(OH) *- CF(OH)
*4-
1
1
Where R CHJJOH, IT, Me or COgft
2
R(cid:127) Aryl (anthraquinone derivative)
The glycone moiety of the anthraglucoside can be
D-glucose, P-galactose, D-fructpSe, L-rhamanose, D-xylose,
L-arabinose or D-glucuronic acid16. D-glucose is the most
common in the natural glycosides, where as D-f ructose and
D-glucuronic acids are rare.
17
The aglycones of natural glycosides may contain
condensed ring system such as hydroxyanthraquinones.
#
4
st
2.2 ANTHRAOUIMQNES
The synthesis of alizarin from anthracene''18’19 in
1868 and the elucidatioh <if thb generic relationship between
\
anthfacenb, anthraculindhe itnd alizarin, may be said to mark
the beginning of a he\V eha in the study of the chemistry of
anthraquinone and its derivatives.
The quinone-like character of anthraquinone was
first clearly recognized by Graebe and Liebermann?^0 who
showed that it bore the same structural relationship to
anthracene as benzoquinone did to benzene. The generally
accepted diketo formula for this compounds was suggested
21.
by Fitting
2.21 NOMENCLATURE
The ten position, in anthracene are numbered as
indicated below,
r
8 9 1
; YY
2
J
3
\Aj
5 10 4