Surface flavonoid profiles in forty populations of Artemisia vulgaris L. (Asteraceae) were analyzed. The major constituents observed in the leaf exudates were methylated flavonoid aglycones based mainly on quercetin. Three infraspecific flavonoid chemotypes were determined,
the chrysosplenetin (quercetagetin 3,6,7,3’-tetramethyl ether) chemotype, the artemetin (quercetagetin 3,6,7,3’,4’-pentamethyl ether) chemotype and chemotype without these two compounds. Most of the populations corresponded to these chemotypes

M. Nikolova

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Acta Bot. Croat. 65 (1), 13–18, 2006 CODEN: ABCRA25ISSN 0365–0588Infraspecific variability in the flavonoidcomposition of Artemisia vulgaris L.MILENA NIKOLOVA*Institute of Botany, Bulgarian Academy of Sciences, 23, Acad. G. Bonchev str. 1113Sofia, BulgariaSurface flavonoid profiles in forty populations of Artemisia vulgaris L. (Asteraceae) wereanalyzed. The major constituents observed in the leaf exudates were methylated flavonoidaglycones based mainly on quercetin. Three infraspecific flavonoid chemotypes were de-termined, the chrysosplenetin (quercetagetin 3,6,7,3’-tetramethyl ether) chemotype, theartemetin (quercetagetin 3,6,7,3’,4’-pentamethyl ether) chemotype and chemotype with-out these two compounds. Most of the populations corresponded to these chemotypes.Key words: Artemisia vulgaris, Asteraceae, flavonoid aglycones, chrysosplenetin, arte-metin, chemotypeIntroductionSurface flavonoid aglycones are often used in chemotaxonomic studies on Asteraceaeat the generic and species level (VALANT-VETSCHERA and WOLLENWEBER 1996, WOLLEN-WEBER et al. 1997, STEVENS et al. 1999). Recent articles showed that a flavonoid patterncould also be specific for a chemotype (REP^ÁK et al. 1999, WILLIAMS et al. 2000,MARTONFI et al. 2001, VIEIRA et al. 2003).The species of the genus Artemisia (Asreraceae) have been extensively surveyed fortheir surface flavonoid constituents (WOLLENWEBER et al. 1989, VALANT-VETSCHERA andWOLLENWEBER 1995, WOLLENWEBER and VALANT-VETSCHERA 1996). Artemisia vulgaris L(Asteraceae) is a perennial polymorphic species, widespread in temperate areas (SouthEurope, North Africa, North America and Asia). Simple flavonol methyl ethers have beenreported for West-European populations (VALANT-VETSCHERA et al. 2003) and flavone de-rivatives for Asian populations (LEE et al. 1998) of A. vulgaris.The present paper is concerning with the surface flavonoid aglycones on 40 populationsof Artemisia vulgaris. The sampling of populations from habitats with different conditionsallowed us to assess the influence of environmental conditions on flavonoid synthesis andaccumulation.ACTA BOT. CROAT. 65 (1), 2006 13* Corresponding author, e-mail: milena_n@bio.bas.bgMaterial and methodsPlant material was collected from natural habitats on 40 populations of A. vulgaris fromBulgaria, details of which are given in Table 1. The sampling sites were chosen to cover re-14 ACTA BOT. CROAT. 65 (1), 2006NIKOLOVA M.Tab. 1. Voucher numbers (SOM) and collection sites of A. vulgaris populations. No – numbers ofsamples, m asl – meters above sea levelNo SOMAltitudemasl Origin of material, pollution impact1 155134 800 Sofia region, metal work, industrial polluted2 Co573 500 Sofia region, chemical work, industrial polluted3 Co663 500 Sofia region, there is flying toxic fragments to air, industrial polluted4 Co515 750 Vitosha mountain, background polluted5 155136 500 Sofia, center, traffic crossing, traffic polluted6 Co557 600 Sofia, housing district, traffic polluted7 Co578 800 Vitosha mountain, background polluted8 Co606 750 Lozen mountain, background polluted9 Co577 1000 Vitosha mountain, background polluted10 Co571 600 Sofia, airport, traffic polluted11 Co662 600 Sofia, boulevard main street, traffic polluted12 Co510 600 Railway station between metal work and uranium mine, industrial polluted13 155138 800 Pernic, metal work, industrial polluted14 Co566 600 Sofia, traffic crossing, traffic polluted15 Co570 600 Sofia, bus station »East«, traffic polluted16 Co608 50 Varna, traffic polluted17 Co574 900 Vitosha mountain, background polluted18 Co520 300 Vratza, chemical work, industrial polluted19 Co511 800 Uranium mine, industrial polluted20 Co518 1400 Vitosha mountain, background polluted21 Co519 30 Bourgas, petrol work, industrial polluted22 Co508 550 Sofia, center, traffic polluted23 Co569 600 Sofia, bus station, »South«, traffic polluted24 Co561 600 Sofia, bus station »North«, traffic polluted25 Co568 600 Sofia bus station »West«, traffic polluted26 Co652 800 Trunk-road around Sofia, traffic polluted27 Co565 500 Sofia region, traffic polluted28 Co682 600 Sofia housing district, traffic polluted29 Co694 600 Sofia, Metro station, traffic polluted30 Co562 650 Ljuin mountain, background polluted31 Co558 800 Vitosha mountain, background polluted32 Co609 700 Ljulin mountain, background polluted33 Co556 1440 Vitosha mountain, background polluted34 Co642 1470 Vitosha mountain, background polluted35 155141 1555 Vitosha mountain, background polluted36 Co512 1800 Vitosha mountain, background polluted37 Co560 1300 Vitosha mountain, background polluted38 Co661 350 Strandzha mountain, background polluted39 Co647 550 Sofia region, installation of centralized heating system, industrial polluted40 Co648 500 Sofia region, housing distinctgions with different types and degrees of environmental pollution as well as at different al-titudes. Voucher specimens were deposited at the Herbarium of the Institute of Botany, So-fia (SOM).Plant exudates were prepared from air-dried, not ground aerial parts (2g) by rinsed withacetone 20 mL for 5 min to dissolve the material accumulated on leaf and stem surfaces.After evaporation of acetone, the dried extracts were dissolved in 250 µL methanol. 40 µLfrom each A. vulgaris exudate were applied in triplicate on TLC plates for analysis. TwoTLC systems were used for identification and quantification of flavonoid aglycones. Tolu-ene-dioxan-acetic acid (95:25:4, v/v/v) was used for the development of silica gel platesKiselgel 60 F254 (10x20 cm, 0.2 mm layer). Toluene-methylethylketone-methanol (60:25:15,v/v/v) was used for development on polyamide DC-11 plates (10x20 cm, 0.15 mm layer).Chromatograms were viewed under UV radiation=336 nm before and after spraying with»Naturstoffreagenz A« (a 1% methanolic solution of diphenyl-boric acid –ethanolaminecomplex).Seven flavonoid aglycones were used as reference compounds in the TLC screening,namely, kaempferol 3,7-dimethyl ether (A), quercetin (B), quercetin 3,3’-dimethyl ether(C), quercetin 3,7-dimethyl ether (D), quercetin 3,7,3’-trimethyl ether (E), quercetagetin3,6,7,3’-tetramethyl ether (F), quercetagetin 3,6,7,3’,4’-pentamethyl ether (G) (Fig. 1).Compounds have been isolated and identified from Artemisia vulgaris in a previous study(NIKOLOVA 2002).Variation of flavonoid compounds within populations of the taxa involved was esti-mated by TLC analysis of 3 individuals from populations.ACTA BOT. CROAT. 65 (1), 2006 15FLAVONOID COMPOSITION OF ARTEMISIA VULGARISR5R4R3R2R1OoR6R1=R5=H, R2=R4=OH, R3=R6=OCH3 kaempferol 3,7-dimethyl ether (A)R1=R2=R3=R4=R6=OH, R5=H quercetin (B)R1=R3=OCH3, R2= R4=R6=OH, R5=H quercetin 3,3’-dimethyl ether (C)R1=R4=R6=OH, R3=R6=OCH3, R5=H quercetin 3,7-dimethyl ether (D)R1=R3=R6=OCH3, R1=R4=OH, R5=H quercetin 3,7,3’-trimethyl ether (E)R1=R3=R5=R6=OCH3, R2=R4=OH quercetagetin 3,6,7,3’-tetramethyl ether (F)R1=R2=R3=R5=R6=OCH3, R4=OH quercetagetin 3,6,7,3’,4’-pentamethyl ether (G)Fig. 1. Structures of the flavonoid aglycones found in Artemisia vulgarisResults and discussionA TLC survey of flavonoid profiles on 40 populations of A. vulgaris was performed andthe results are given in Table 2. Methylated free flavonoid aglycones based mainly onquercetin were accumulated in the leaf exudates of the studied populations. Quercetin3,7,3’-trimethyl ether appeared to be the main flavonoid aglycone. The aglycone kaemphe-rol 3,7-dimethyl ether was found only in trace amounts. Quercetin, quercetin 3,7-dimethylether and quercetin 3,3’-dimethyl ether were also detected. The differences in the qualita-tive flavonoid composition among populations related to highly methylated quercetagetinderivatives – quercetagetin 3,6,7,3’-tetramethyl ether and quercetagetin 3,6,7,3’,4’-penta-methyl ether. These compounds were proved only in some populations. The populations(1–9) yielded quercetagetin 3,6,7,3’-tetramethyl ether (chrysosplenetin chemotype). Thelatter compound was not observed in the exudates of populations (10–20) where quercet-agetin 3,6,7,3’,4’-pentamethyl ether was established (artemetin chemotype). In the exudatesof populations (21–40) neither one of these two compounds was (chemotypes withoutquercetagetin derivatives). The latter chemotype appeared to be the most widespread, inapproximately 50% of all studied populations. This is in agreement with a recent publica-tion on the flavonoid content in three populations of A. vulgaris from Austria and Germany(VALANT-VETSCHERA et al., 2003), where only chemotypes without quercetagetin deriva-tives have been established.The presence of chemotypes of the plants in relation to altitudinal gradient has been de-scribed (SEIGLER and WOLLENWEBER 1983, MCDOUGAL and PARKS 1984). Therefore, welooked for a correlation between altitude or environmental pollution and flavonoid compo-sition of A. vulgaris. Only a variability in the quantitative flavonoid composition of A.vulgaris was observed whereas no relation was found between qualitative flavonoid com-position and altitude or type of environmental pollution. This result supports the view thatqualitative flavonoid composition is a suitable marker for chemotaxonomic researches inA. vulgaris.The present results are another example of flavonoid chemotypes in plants. Compara-tive analysis of flavonoid content and other signs of populations (ploidy level) of A.vulgaris will be subject of future investigation.ReferencesLEE, S., CHUNG, H., MAIER, C., WOOD, A., DIXON, R., MABRY, T., 1998: Estrogenicflavonoids from Artemisia vulgaris L. J. Agric. Food Chem. 46, 3325–3329.MARTONFI, P., REP^ÁK, M., CICCARELLI, D., GARBARI, F., 2001: Hypericum perforatum L. –chemotype without rutin from Italy. Biochem. Syst. Ecol. 29, 659–661.MCDOUGAL, K., PARKS, C., 1984: Elevational variation in foliar flavonoids of Quercusrubra L. (Fagaceae). Am. J. Bot. 71, 301–308.NIKOLOVA, M., 2002: Effects of the environmental pollution and altitudinal gradient on theflavonoid content in the species of genera Artemisia L. and Veronica L., PhD Thesis,University of Sofia.REP^ÁK, M., [VEHLIKOVA, V., IMRICH, J., PIHLAJA, K., 1999: Jaceidin and chrysosplenetinchemotypes of Chamomilla recutita (L.) Rauschert. Biochem. Syst. Ecol. 27, 727–732.16 ACTA BOT. CROAT. 65 (1), 2006NIKOLOVA M.ACTA BOT. CROAT. 65 (1), 2006 17FLAVONOID COMPOSITION OF ARTEMISIA VULGARISTab. 2. Distribution of flavonoid aglycones in Artemisia vulgaris populations. A: kaempferol3,7-dimethyl ether, B: quercetin, C: quercetin 3,3’-dimethyl ether, D: quercetin 3,7-dime-thyl ether, E: quercetin 3,7,3’-trimethyl ether, F: quercetagetin 3,6,7,3’-tetramethyl ether,G: quercetagetin 3,6,7,3’,4’-pentamethyl ether; (–) absent; (tr.) present in trace amounts ()present in small amounts; () present in normal amounts () present in large amountsSampleNoFlavonoid aglyconesA B C D E F G1 tr.      –2 tr.      –3 tr.      –4 tr.      –5 tr. tr.    tr. –6 tr.    tr. –7 tr.     tr. –8 tr.     tr. –9 tr.     10 tr.  tr. tr.  – 11 tr.     – 12 tr.     – 13 tr.     – 14 tr.     – 15 tr.     – 16 tr.     – 17 tr.     – 18 tr.     – tr.19 tr.     – tr.20 tr.     – 21 tr.     – –22 tr.     – –23 tr.     – –24 tr.     – –25 tr.     – –26 tr.     – –27 tr.     – –28 tr.     – –29 tr.     – –30 tr.   tr.  – –31 tr.     – –32 tr.     – –33 tr.    tr. – –34 tr.     – –35 –  tr. tr.  – –36 tr.  tr.   – –37   tr. tr.  – –38 tr     – –39 tr     – –40 tr     – –SEIGLER, D., WOLLENWEBER, E., 1983: Chemical variation in Notholaena standleyi. Amer.J. Bot. 70, 790–798.STEVENS, J. F., WOLLENWEBER, E., IVANCIC, M. HSU, V., SUNDBERG, S. DEINZER, M., 1999:Leaf surface flavonoids of Chrysothamnus. Phytochemistry 51, 771–780.VALANT-VETSCHERA, K., WOLLENWEBER, E., 1995: Flavonoid aglycones from the leaf sur-face of some Artemisia sp. Z. Naturforsch. 50, 353–357.VALANT-VETSCHERA, K., WOLLENWEBER, E., 1996: Comparative analysis of leaf exudatesflavonoids in Achillea subsect. Filipendulinae. Biochem. Syst. Ecol. 24, 435–446.VALANT-VETSCHERA, K., FISCHER, R., WOLLENWEBER, E., 2003: Exudate flavonoids in spe-cies of Artemisia (Asteraceae-Anthemideae): new results and chemosystematic inter-pretation. Biochem. Syst. Ecol. 31, 487–498.VIEIRA, R., GRAYER, R., PATON, A., 2003: Chemical profiling of Ocimum amaricanum us-ing external flavonoids. Phytochemistry 63, 555–567.WILLIAMS, C., HARBORNE, J., GREENHAM, J., 2000: Geographical variation in the surfaceflavonoids of Pulicaria dysenterica. Biochem. Syst. Ecol. 28, 679–687.WOLLENWEBER, E., 1990: On the distribution of exudate flavonoids among Anigosperms.Rev. Latinoamer. Quim. 21, 115–121.WOLLENWEBER, E., MAAN, K., VALANT-VETSCHER, K., 1989: External flavonoid aglyconesin Artemisia and some further Anthemideae (Asteraceae). Fitoterapia 60, 460–463.WOLLENWEBER, E., VALANT-VETSCHER, K. 1996: New results with exudate flavonoids inCompositae. Proc. Int. Comp. Conf. Kew, Royal Botanic Gardens, Kew, 169–18518 ACTA BOT. CROAT. 65 (1), 2006NIKOLOVA M.

English

Infraspecific variability in the flavonoid composition of Artemisia vulgaris L.

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Acta Bot. Croat. 65 (1), 13–18, 2006 CODEN:ABCRA25ISSN 0365–0588Infraspecific variability in the flavonoidcomposition of Artemisia vulgaris L.MILENANIKOLOVA*Institute of Botany, Bulgarian Academy of Sciences, 23, Acad. G. Bonchev str. 1113Sofia, BulgariaSurface flavonoid profiles in forty populations of Artemisia vulgaris L. (Asteraceae) wereanalyzed. Themajor constituents observed in the leaf exudates weremethylated flavonoidaglycones based mainly on quercetin. Three infraspecific flavonoid chemotypes were de-termined, the chrysosplenetin (quercetagetin 3,6,7,3’-tetramethyl ether) chemotype, theartemetin (quercetagetin 3,6,7,3’,4’-pentamethyl ether) chemotype and chemotype with-out these two compounds. Most of the populations corresponded to these chemotypes.Key words: Artemisia vulgaris, Asteraceae, flavonoid aglycones, chrysosplenetin, arte-metin, chemotypeIntroductionSurface flavonoid aglycones are often used in chemotaxonomic studies on Asteraceaeat the generic and species level (VALANT-VETSCHERA and WOLLENWEBER 1996, WOLLEN-WEBER et al. 1997, STEVENS et al. 1999). Recent articles showed that a flavonoid patterncould also be specific for a chemotype (REP^ÁK et al. 1999, WILLIAMS et al. 2000,MARTONFI et al. 2001, VIEIRA et al. 2003).The species of the genus Artemisia (Asreraceae) have been extensively surveyed fortheir surface flavonoid constituents (WOLLENWEBER et al. 1989, VALANT-VETSCHERA andWOLLENWEBER 1995, WOLLENWEBER and VALANT-VETSCHERA 1996). Artemisia vulgaris L(Asteraceae) is a perennial polymorphic species, widespread in temperate areas (SouthEurope, North Africa, North America and Asia). Simple flavonol methyl ethers have beenreported for West-European populations (VALANT-VETSCHERA et al. 2003) and flavone de-rivatives for Asian populations (LEE et al. 1998) of A. vulgaris.The present paper is concerningwith the surface flavonoid aglycones on 40 populationsof Artemisia vulgaris. The sampling of populations from habitats with different conditionsallowed us to assess the influence of environmental conditions on flavonoid synthesis andaccumulation.ACTA BOT. CROAT. 65 (1), 2006 13* Corresponding author, e-mail: milena_n@bio.bas.bgMaterial and methodsPlant material was collected from natural habitats on 40 populations of A. vulgaris fromBulgaria, details of which are given in Table 1. The sampling sites were chosen to cover re-14 ACTA BOT. CROAT. 65 (1), 2006NIKOLOVA M.Tab. 1. Voucher numbers (SOM) and collection sites of A. vulgaris populations. No – numbers ofsamples, m asl – meters above sea levelNo SOMAltitudemasl Origin of material, pollution impact1 155134 800 Sofia region, metal work, industrial polluted2 Co573 500 Sofia region, chemical work, industrial polluted3 Co663 500 Sofia region, there is flying toxic fragments to air, industrial polluted4 Co515 750 Vitosha mountain, background polluted5 155136 500 Sofia, center, traffic crossing, traffic polluted6 Co557 600 Sofia, housing district, traffic polluted7 Co578 800 Vitosha mountain, background polluted8 Co606 750 Lozen mountain, background polluted9 Co577 1000 Vitosha mountain, background polluted10 Co571 600 Sofia, airport, traffic polluted11 Co662 600 Sofia, boulevard main street, traffic polluted12 Co510 600 Railway station between metal work and uranium mine, industrial polluted13 155138 800 Pernic, metal work, industrial polluted14 Co566 600 Sofia, traffic crossing, traffic polluted15 Co570 600 Sofia, bus station »East«, traffic polluted16 Co608 50 Varna, traffic polluted17 Co574 900 Vitosha mountain, background polluted18 Co520 300 Vratza, chemical work, industrial polluted19 Co511 800 Uranium mine, industrial polluted20 Co518 1400 Vitosha mountain, background polluted21 Co519 30 Bourgas, petrol work, industrial polluted22 Co508 550 Sofia, center, traffic polluted23 Co569 600 Sofia, bus station, »South«, traffic polluted24 Co561 600 Sofia, bus station »North«, traffic polluted25 Co568 600 Sofia bus station »West«, traffic polluted26 Co652 800 Trunk-road around Sofia, traffic polluted27 Co565 500 Sofia region, traffic polluted28 Co682 600 Sofia housing district, traffic polluted29 Co694 600 Sofia, Metro station, traffic polluted30 Co562 650 Ljuin mountain, background polluted31 Co558 800 Vitosha mountain, background polluted32 Co609 700 Ljulin mountain, background polluted33 Co556 1440 Vitosha mountain, background polluted34 Co642 1470 Vitosha mountain, background polluted35 155141 1555 Vitosha mountain, background polluted36 Co512 1800 Vitosha mountain, background polluted37 Co560 1300 Vitosha mountain, background polluted38 Co661 350 Strandzha mountain, background polluted39 Co647 550 Sofia region, installation of centralized heating system, industrial polluted40 Co648 500 Sofia region, housing distinctgions with different types and degrees of environmental pollution as well as at different al-titudes. Voucher specimens were deposited at the Herbarium of the Institute of Botany, So-fia (SOM).Plant exudates were prepared from air-dried, not ground aerial parts (2g) by rinsed withacetone 20 mL for 5 min to dissolve the material accumulated on leaf and stem surfaces.After evaporation of acetone, the dried extracts were dissolved in 250 µLmethanol. 40 µLfrom each A. vulgaris exudate were applied in triplicate on TLC plates for analysis. TwoTLC systems were used for identification and quantification of flavonoid aglycones. Tolu-ene-dioxan-acetic acid (95:25:4, v/v/v) was used for the development of silica gel platesKiselgel 60 F254 (10x20 cm, 0.2 mm layer). Toluene-methylethylketone-methanol (60:25:15,v/v/v) was used for development on polyamide DC-11 plates (10x20 cm, 0.15 mm layer).Chromatograms were viewed under UV radiation=336 nm before and after spraying with»Naturstoffreagenz A« (a 1% methanolic solution of diphenyl-boric acid –ethanolaminecomplex).Seven flavonoid aglycones were used as reference compounds in the TLC screening,namely, kaempferol 3,7-dimethyl ether (A), quercetin (B), quercetin 3,3’-dimethyl ether(C), quercetin 3,7-dimethyl ether (D), quercetin 3,7,3’-trimethyl ether (E), quercetagetin3,6,7,3’-tetramethyl ether (F), quercetagetin 3,6,7,3’,4’-pentamethyl ether (G) (Fig. 1).Compounds have been isolated and identified from Artemisia vulgaris in a previous study(NIKOLOVA 2002).Variation of flavonoid compounds within populations of the taxa involved was esti-mated by TLC analysis of 3 individuals from populations.ACTA BOT. CROAT. 65 (1), 2006 15FLAVONOID COMPOSITION OF ARTEMISIA VULGARISR5R4R3R2R1OoR6R1=R5=H, R2=R4=OH, R3=R6=OCH3 kaempferol 3,7-dimethyl ether (A)R1=R2=R3=R4=R6=OH, R5=H quercetin (B)R1=R3=OCH3, R2= R4=R6=OH, R5=H quercetin 3,3’-dimethyl ether (C)R1=R4=R6=OH, R3=R6=OCH3, R5=H quercetin 3,7-dimethyl ether (D)R1=R3=R6=OCH3, R1=R4=OH, R5=H quercetin 3,7,3’-trimethyl ether (E)R1=R3=R5=R6=OCH3, R2=R4=OH quercetagetin 3,6,7,3’-tetramethyl ether (F)R1=R2=R3=R5=R6=OCH3, R4=OH quercetagetin 3,6,7,3’,4’-pentamethyl ether (G)Fig. 1. Structures of the flavonoid aglycones found in Artemisia vulgarisResults and discussionATLC survey of flavonoid profiles on 40 populations of A. vulgaris was performed andthe results are given in Table 2. Methylated free flavonoid aglycones based mainly onquercetin were accumulated in the leaf exudates of the studied populations. Quercetin3,7,3’-trimethyl ether appeared to be the main flavonoid aglycone. The aglycone kaemphe-rol 3,7-dimethyl ether was found only in trace amounts. Quercetin, quercetin 3,7-dimethylether and quercetin 3,3’-dimethyl ether were also detected. The differences in the qualita-tive flavonoid composition among populations related to highly methylated quercetagetinderivatives – quercetagetin 3,6,7,3’-tetramethyl ether and quercetagetin 3,6,7,3’,4’-penta-methyl ether. These compounds were proved only in some populations. The populations(1–9) yielded quercetagetin 3,6,7,3’-tetramethyl ether (chrysosplenetin chemotype). Thelatter compound was not observed in the exudates of populations (10–20) where quercet-agetin 3,6,7,3’,4’-pentamethyl ether was established (artemetin chemotype). In the exudatesof populations (21–40) neither one of these two compounds was (chemotypes withoutquercetagetin derivatives). The latter chemotype appeared to be the most widespread, inapproximately 50% of all studied populations. This is in agreement with a recent publica-tion on the flavonoid content in three populations of A. vulgaris fromAustria and Germany(VALANT-VETSCHERA et al., 2003), where only chemotypes without quercetagetin deriva-tives have been established.The presence of chemotypes of the plants in relation to altitudinal gradient has been de-scribed (SEIGLER and WOLLENWEBER 1983, MCDOUGAL and PARKS 1984). Therefore, welooked for a correlation between altitude or environmental pollution and flavonoid compo-sition of A. vulgaris. Only a variability in the quantitative flavonoid composition of A.vulgaris was observed whereas no relation was found between qualitative flavonoid com-position and altitude or type of environmental pollution. This result supports the view thatqualitative flavonoid composition is a suitable marker for chemotaxonomic researches inA. vulgaris.The present results are another example of flavonoid chemotypes in plants. Compara-tive analysis of flavonoid content and other signs of populations (ploidy level) of A.vulgaris will be subject of future investigation.ReferencesLEE, S., CHUNG, H., MAIER, C., WOOD, A., DIXON, R., MABRY, T., 1998: Estrogenicflavonoids from Artemisia vulgaris L. J. Agric. Food Chem. 46, 3325–3329.MARTONFI, P., REP^ÁK,M., CICCARELLI, D., GARBARI, F., 2001: Hypericum perforatum L. –chemotype without rutin from Italy. Biochem. Syst. Ecol. 29, 659–661.MCDOUGAL, K., PARKS, C., 1984: Elevational variation in foliar flavonoids of Quercusrubra L. (Fagaceae). Am. J. Bot. 71, 301–308.NIKOLOVA, M., 2002: Effects of the environmental pollution and altitudinal gradient on theflavonoid content in the species of genera Artemisia L. and Veronica L., PhD Thesis,University of Sofia.REP^ÁK, M., [VEHLIKOVA, V., IMRICH, J., PIHLAJA, K., 1999: Jaceidin and chrysosplenetinchemotypes ofChamomilla recutita (L.) Rauschert. Biochem. Syst. Ecol. 27, 727–732.16 ACTA BOT. CROAT. 65 (1), 2006NIKOLOVA M.ACTA BOT. CROAT. 65 (1), 2006 17FLAVONOID COMPOSITION OF ARTEMISIA VULGARISTab. 2. Distribution of flavonoid aglycones in Artemisia vulgaris populations. A: kaempferol3,7-dimethyl ether, B: quercetin, C: quercetin 3,3’-dimethyl ether, D: quercetin 3,7-dime-thyl ether, E: quercetin 3,7,3’-trimethyl ether, F: quercetagetin 3,6,7,3’-tetramethyl ether,G: quercetagetin 3,6,7,3’,4’-pentamethyl ether; (–) absent; (tr.) present in trace amounts ()present in small amounts; () present in normal amounts () present in large amountsSampleNoFlavonoid aglyconesA B C D E F G1 tr.      –2 tr.      –3 tr.      –4 tr.      –5 tr. tr.    tr. –6 tr.    tr. –7 tr.     tr. –8 tr.     tr. –9 tr.     10 tr.  tr. tr.  – 11 tr.     – 12 tr.     – 13 tr.     – 14 tr.     – 15 tr.     – 16 tr.     – 17 tr.     – 18 tr.     – tr.19 tr.     – tr.20 tr.     – 21 tr.     – –22 tr.     – –23 tr.     – –24 tr.     – –25 tr.     – –26 tr.     – –27 tr.     – –28 tr.     – –29 tr.     – –30 tr.   tr.  – –31 tr.     – –32 tr.     – –33 tr.    tr. – –34 tr.     – –35 –  tr. tr.  – –36 tr.  tr.   – –37   tr. tr.  – –38 tr     – –39 tr     – –40 tr     – –SEIGLER, D., WOLLENWEBER, E., 1983: Chemical variation in Notholaena standleyi. Amer.J. Bot. 70, 790–798.STEVENS, J. F., WOLLENWEBER, E., IVANCIC, M. HSU, V., SUNDBERG, S. DEINZER, M., 1999:Leaf surface flavonoids of Chrysothamnus. Phytochemistry 51, 771–780.VALANT-VETSCHERA, K., WOLLENWEBER, E., 1995: Flavonoid aglycones from the leaf sur-face of some Artemisia sp. Z. Naturforsch. 50, 353–357.VALANT-VETSCHERA, K., WOLLENWEBER, E., 1996: Comparative analysis of leaf exudatesflavonoids in Achillea subsect. Filipendulinae. Biochem. Syst. Ecol. 24, 435–446.VALANT-VETSCHERA, K., FISCHER, R., WOLLENWEBER, E., 2003: Exudate flavonoids in spe-cies of Artemisia (Asteraceae-Anthemideae): new results and chemosystematic inter-pretation. Biochem. Syst. Ecol. 31, 487–498.VIEIRA, R., GRAYER, R., PATON, A., 2003: Chemical profiling of Ocimum amaricanum us-ing external flavonoids. Phytochemistry 63, 555–567.WILLIAMS, C., HARBORNE, J., GREENHAM, J., 2000: Geographical variation in the surfaceflavonoids of Pulicaria dysenterica. Biochem. Syst. 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Infraspecific variability in the flavonoid composition of Artemisia vulgaris L.

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