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Short Report

Antibacterial furofuran lignans from Canary Islandspropolis

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

aInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Bl.

9, Acad. G. Bonchestr., 1113 Sofia, BulgariabInstitute of Microbiology, Bulgarian Academy of Sciences, Bl. 9, Acad. G. Bonchestr., 1113

Sofia, Bulgaria

cAsociacion 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 1 .

Previously isolated constituents. Flavonoids, aromatic alcohols, aldehydes, acidsand esters, aliphatic acids and esters, hydrocarbons, terpenoids mainly sesquiter-

. penoids , amino acids, sugars 13 , one benzofurane lignan 4 .

. . . .New-isolated constituents. Sesamin 1 5 0.8% , aschantin 2 5 1.0 , sesartemin

. . . .3 6 0.9 , yangambin 4 5 1.3 .

Corresponding author. Fax: 359 2700225; e-mail: iochnp@bgcict.acad.bg

0367-326X99$ - see front matter 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

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R R R R R R1 2 3 4 5 6

1 OCH O H OCH O H2 22 OMe OMe OMe OCH O H23 OMe OMe OMe OCH O OMe24 OMe OMe OMe OMe OMe OMe

. . . . . .Sesamin 1 . EIMS mz rel. int : 354 M , 19 , 161 24 , 149 100 , 135 39 ;13 . . .C-NMR 62.9 MHz, CDCl : 147.9 C-3 and C-3 , 147.0 C-4 and C-4 ,3

. . . 135.0 C-1 and C-1 , 119.3 C-5 and C-5 , 108.1 6 and 6 , 106.4 C-2 and. . . . .C-2 , 101.0 two OCH O , 85.7 C-2 and C-6 , 71.6 C-4, C-8 , 54.2 C-1 and C-5 .2

. . . . . .Aschantin 2 . EIMS mz rel. int : 400 M , 84 , 207 31 , 195 42 , 181 54 , 149 . . 13 . .100 , 135 63 ; C-NMR 62.9 MHz, CDCl : 153.3 C-3 and C-5 , 147.93 . . . . . .C-3, 147.0 C-4 , 137.3 C-4 , 136.7 C-1 , 134.9 C-1, 119.3 C-5 , 109.0 . . . . .C-6 , 108.1 C-2 , 102.5 C-2 and C-6 , 71.9 C-4 or C-8 , 71.6 C-4 or C-8 , 60.8 . . . .4-OCH , 56.1 3-OCH and 5-OCH , 54.3 C-1 or C-5 , 54.2 C-1 or C-5 .3 3 3

. . . . . .Seartemin 3 . EIMS mz rel. int : 430 M , 69 , 207 46 , 195 44 , 191 35 , 181 . . . 13 . .67 , 179 100 , 165 70 ; C-NMR 62.9 MHz, CDCl : 153.4 C-3 and C-5 ,3

. . . . . .149.1 C-3 , 143.6 C-5, 137.4 C-4 , 136.7 C-1 , 135.7 C-1 , 134.6 C-4 , . . . . .105.6 C-2 , 102.8 C-2 and C-6 , 101.4 OCH O , 100.0 C-6, 85.9 C-4 or C-8 ,2

. . . .85.7 C-4 or C-8 , 60.8 4-OCH , 56.7 5-OCH , 56.1 3- and 5-OCH , 54.33 3 3 .C-1 and C-5 .

. . . . . .Yangambin 4 . EIMS mz rel. int. : 446 M , 53 , 207 60 , 195 62 , 181 100 ;13 . . C-NMR 62.9 MHz, CDCl : 153.3 C-3, C-3, C-5and C-5 , 148.5 C-4and3

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

.spot

.Substance Zone of inhibition mm

S. aureus E. coli

Propolis extract 9 1 71 .Sesamin 1 8 1 0

.Aschantin 2 8.3 0.6 0 .Sesartenin 3 7 1 8.3 0.6

.Yangambin 4 8.3 0.6 8.3 0.6aStreptomycin 28 1 0

a One hundred micrograms on the spot.Tests were done in triplicate, values are mean S.D.

. . .C-4 137.3 C-1 and C-1 , 102.4 C-2, C-2, C-6 and C-6 , 77.5 C-2 and C-6 . . . 71.9 C-4 and C-8 , 60.8 4-, 4-OCH , 56.1 3-, 3-, 5-, 5-OCH , 54.4 C-1 and3 3

.C-5 .

.Tested materials. Propolis extract with 70% ethanol 1:10 wv, yield 42% andisolated compounds 1 4.

Studied activity. Antimicrobial activity by the modified diffusion method 7 .

Used organisms. Staphylococcus aureus 209, obtained from the Bulgarian TypeCulture Collection. Institute for State Control of Drugs, Sofia; and Escherichia coli

WF 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 isolatedfurofuran lignans, showed weak activity against both test microorganisms. Sesamin ) .1 and aschantin 2 were inactive against E. coli. Our results confirmed onceagain the well-known fact that no single constituent has larger antibacterial activitythan the whole propolis extract. Canary Islands propolis reveals a totally differentchemical composition, compared to European and other tropical samples. Never-theless, its antibacterial activity remains almost the same as that of propolis from

other geographic locations 8,9 .

Acknowledgements

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

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

References

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International Conference on Chem. Biotechnol. Biologically Active Nat. Subst., Varna 1997, vol. 2.Sofia: Bulg. Acad. Sci. Press, 1989:239.

9 Bankova V, Christov R, Kujumgiev A, Marcucci MC, Popov S. Z Naturforsch 1995;50:167.