PREPARATION OF MODIFIED CARBOHYDRATES WITH BIOLOGICAL ACTIVITY

, *, *,
GEORGY MATEV, NADEZHDA PETKOVA*, PANTELEY DENEV*, VENELINA POPOVA , STEPAN AKTERIAN

* UNIVERSITY OF FOOD TECHNOLOGIES - PLOVDIV, DEPARTMENT OF ORGANIC CHEMISTRY AND MICROBIOLOGY, Bul. Maritza 26,
Plovdiv, Bulgaria petkovanadejda@abv.bg

Abstract

Sugar and oligofructoses esters with saturated fatty acids (6 to 18) and
10-unsaturated undecylenic acid 11 have been obtained. A new method
for synthesis with the ultrasonic influence has been developed and applied.
Prepared carbohydrate esters have been characterized by measurement of
melting point, thin layer chromatography (TLC) and IR-FT. The antimicrobial
activity of the syntheses sugar esters has been investigated. Sucrolaurate is
characterized by well pronounced bacteriostatic activity against fungi
Aspergillus and Penicillium, Gram positive bacteria: Bacillus subtilis and
Staphylococcus aureus.

(6 18) 10- 11.
, .

, TLC IR-FT.
.

Aspergillus Penicillium - Bacillus
subtilis Staphylococcus aureus.

O
CH2
O

CH2
O

CH 2

1,2
1,1

- ,
. ,
,
[3] [2].
,
[1,3,5].
Nicotiana sp., Solanum sp., Datura sp. .,

6-12 ( ) [3,4].

:
,
. ,
[5,6].

O
O

OH
OH

0,6
0,5

HO
0,4
0,3

NP6
CLR

NP6-1

0,2

CH2

0,1
0
3500

.3.

3000

2500

2000

1500

1000

500

O O

Wavenumbers [1/cm]

.4. IR-FT

. 1.

CH2

186-188

135

84-87

120-123

147-150

163-167

Sisterna SP70

145-147

CLR

154 -157

CLR

110 -115

CLR

72-74

CLR

80 ( 105 )

.2. 0,1% ( -)

Bacillus St. aureus

Listeria
subtilis
monocytogenes

Penicillium
sp.

Aspergillus
sp.

/
ml

/
ml

/
ml

/
ml

./
ml

./
ml

1,3.109

1,8.108

1,2.1010

9,2.1010

2.105

1.105

-*
15*
11*
17*
8**
9**
, mm
* 24 ; ** 48

CH2
O

HO

x eq.CH3OCOR

OH

OH

OH

CH 2O

HO

O
H2C

CH 2OH

O
HO

O
n

n=0,2,4,6,8,10,12
n

O
O
OH

R=C5H11,C7H15, C9H19, C10H20,

C11H23, C13H27, C15H31, C17H35

CH 2OH
OH

.1.

CH2

. 5. 24 h () 48 h ()

OH

NaOMe

OH

CH2O

OH
C

O
CH2

n
O

OH

CH 2

OCH2

HO
HO

HO
HO

O
CH2

135
75 ( 105 )

E. coli

O
CH2

CLR

CH2

HO

CH 2

0,7

O
OH

CH 2OH

0,8

CLR

OH

CH 2OH

CH2O
O

. o
, (Sigma Aldrich) Frutafit CLR (Rosendaal, the Netherlands),
BOECO MSH 300, SIEL UST 5.7-150
. LC Kieselgel G60 F254(20x20), Merck
(Darmstadt), // (17:2:1 v/v) 10%
H2SO4 [6] :
- /// (12:5:4,5:0,2)
[3]. BCHI
510. IR IR-FT Avatar Nicolet
TermoScience Br.
.
1 ml
Thoma.

HO

O
OH

OH

CH2

CH 2O

Transmittance

OCH2

,
.
:
1.
6 18.
2. 10- .
3.
.
4. - .
5. .

OH

1745 cm-1

0,9

3080 cm-1

. 2.

(10-) . IR-FT
C-O
1745 cm-1, .
, .

Listeria monocytogenes, Bacillus subtilis, Staphylococcus aureus
Aspergillus Penicillium,
-
E. coli.

O
O
CH2
O

CH 2

02/28/2010 . " " ,

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Arch. Boil. Techol. v. 51, n. 6, Nov/Dec 2008, 1115-1119
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CH2
O

CH2OH