Fitoterapia 70 1999.

89]92

Short Report

Antibacterial furofuran lignans from Canary Islands

propolis
R. Christov a , V. Bankovaa,U , I. Tsvetkovab, A. Kujumgiev b,
A. Delgado Tejerac
a

Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Bl.
9, Acad. G. Bonche str., 1113 Sofia, Bulgaria
b
Institute of Microbiology, Bulgarian Academy of Sciences, Bl. 9, Acad. G. Bonche str., 1113
Sofia, Bulgaria
c
Asociacion de Apicultores de Gran Canaria, Las Palmas de Gran Canaria, Spain

Received 29 June 1998; accepted 29 September 1998

Keywords: Propolis; Lignans; Antibacterial activity

Material. Propolis was collected at the Canary Islands, island of Gran Canaria,
near Telde, in October 1995.
Uses in traditional medicine. Propolis is used in folk medicine of Eastern Europe
as an antiseptic and anti-inflammatory agent, for healing wounds and burns w1x.
Previously isolated constituents. Flavonoids, aromatic alcohols, aldehydes, acids
and esters, aliphatic acids and esters, hydrocarbons, terpenoids mainly sesquiterpenoids., amino acids, sugars w1]3x, one benzofurane lignan w4x.
New-isolated constituents. Sesamin 1. w5x 0.8%., aschantin 2. w5x 1.0., sesartemin
3. w6x 0.9., yangambin 4. w5x 1.3..
U

Corresponding author. Fax: q359 2700225; e-mail: iochnp@bgcict.acad.bg

0367-326Xr99r$ - see front matter Q 1999 Elsevier Science B.V. All rights reserved.
PII: S 0 3 6 7 - 3 2 6 X 9 8 . 0 0 0 4 4 - 6

R. Christo et al. r Fitoterapia 70 (1999) 89]92

90

R1
1
2
3
4

R2

R3

OMe
OMe
OMe

H
OMe
OMe
OMe

OCH2 O
OMe
OMe
OMe

R4

R5

R6

OMe

H
H
OMe
OMe

OCH2 O
OCH2 O
OCH2 O
OMe

Sesamin 1.. EIMS m r z rel. int.: 354 Mq, 19., 161 24., 149 100., 135 39.;
13
C-NMR 62.9 MHz, CDCl 3 .: d 147.9 C-39 and C-30 ., 147.0 C-49 and C-40 .,
135.0 C-19 and C-10 ., 119.3 C-59 and C-50 ., 108.1 69 and 60 ., 106.4 C-29 and
C-20 ., 101.0 two OCH 2 O., 85.7 C-2 and C-6., 71.6 C-4, C-8., 54.2 C-1 and C-5..
Aschantin 2.. EIMS m r z rel. int.: 400 Mq, 84., 207 31., 195 42., 181 54., 149
100., 135 63.; 13 C-NMR 62.9 MHz, CDCl 3 .: d 153.3 C-39 and C-50 ., 147.9
C-39., 147.0 C-49., 137.3 C-40 ., 136.7 C-10 ., 134.9 C-19., 119.3 C-59., 109.0
C-69., 108.1 C-29., 102.5 C-20 and C-60 ., 71.9 C-4 or C-8., 71.6 C-4 or C-8., 60.8
40-OCH 3 ., 56.1 30-OCH 3 and 50-OCH 3 ., 54.3 C-1 or C-5., 54.2 C-1 or C-5..
Seartemin 3.. EIMS m r z rel. int.: 430 Mq, 69., 207 46., 195 44., 191 35., 181
67., 179 100., 165 70.; 13 C-NMR 62.9 MHz, CDCl 3 .: d 153.4 C-30 and C-50 .,
149.1 C-39., 143.6 C-59., 137.4 C-40 ., 136.7 C-10 ., 135.7 C-19., 134.6 C-49.,
105.6 C-29., 102.8 C-20 and C-60 ., 101.4 OCH 2 O., 100.0 C-69., 85.9 C-4 or C-8.,
85.7 C-4 or C-8., 60.8 400-OCH 3 ., 56.7 59-OCH 3 ., 56.1 30- and 50-OCH 3 ., 54.3
C-1 and C-5..
Yangambin 4.. EIMS m r z rel. int..: 446 Mq, 53., 207 60., 195 62., 181 100.;
13
C-NMR 62.9 MHz, CDCl 3 .: d 153.3 C-39, C-30, C-59 and C-50 ., 148.5 C-49 and

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91

Table 1
Antibacterial activity of Canary Islands propolis and therefrom isolated compounds at 400 m g on the
spot.
Substance

Propolis extract
Sesamin 1.
Aschantin 2.
Sesartenin 3.
Yangambin 4.
Streptomycina

Zone of inhibition mm.

S. aureus

E. coli

9"1
8"1
8.3 " 0.6
7"1
8.3 " 0.6
28 " 1

7 "1
0
0
8.3 " 0.6
8.3 " 0.6
0

One hundred micrograms on the spot.

Tests were done in triplicate, values are mean " S.D.

C-40 137.3 C-19 and C-10 ., 102.4 C-29, C-20, C-69 and C-60 ., 77.5 C-2 and C-6.
71.9 C-4 and C-8., 60.8 49-, 40-OCH 3 ., 56.1 39-, 30-, 59-, 50-OCH 3 ., 54.4 C-1 and
C-5..
Tested materials. Propolis extract with 70% ethanol 1:10 wrv, yield 42%. and
isolated compounds 14.
Studied activity. Antimicrobial activity by the modified diffusion method w7x.
Used organisms. Staphylococcus aureus 209, obtained from the Bulgarian Type
Culture Collection. Institute for State Control of Drugs, Sofia; and Escherichia coli
WF q obtained from the Collection of ZIMET Central Institute for Microbiology
and Experimental Therapy., Jena.
Results. Reported in Table 1.
Conclusions. The propolis sample from the Canary Islands, as well as the isolated
furofuran lignans, showed weak activity against both test microorganisms. Sesamin
1) and aschantin 2. were inactive against E. coli. Our results confirmed once
again the well-known fact that no single constituent has larger antibacterial activity
than the whole propolis extract. Canary Islands propolis reveals a totally different
chemical composition, compared to European and other tropical samples. Nevertheless, its antibacterial activity remains almost the same as that of propolis from
other geographic locations w8,9x.

Acknowledgements
The authors are thankful to Dr Hector Mendoza and Dr Georgi Petkov for help

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R. Christo et al. r Fitoterapia 70 (1999) 89]92

in sample collection. Partial support of this work by the National Foundation for
Scientific Research Contract X-715. is gratefully acknowledged.

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w2x
w3x
w4x
w5x
w6x
w7x
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