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Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity a
ab
d
e
c
Katarzyna Szewczyk , Tadeusz Krzaczek , Tomasz Łopatyński , Urszula Gawlik-Dziki & Christian Zidorn a
Department of Pharmaceutical Botany, Medical University of Lublin, Chodźki 1 St, 20-093 Lublin, Poland b
Institute of Medicine, The State Higher School of Computer Science and Business Administration in Lomza, Akademicka 14 St, 18-400 Łomża, Poland c
Chair and Department of Trauma Surgery and Emergency Medicine, Medical University of Lublin, Staszica 16 St, 20-081 Lublin, Poland d
Department of Biochemistry and Food Chemistry, University of Life Sciences, Skromna 8, Lublin, Poland e
Institut für Pharmazie der Universität Innsbruck, Abteilung Pharmakognosie, Innrain 80/82, A-6020 Innsbruck, Austria Published online: 17 Jul 2014. To cite this article: Katarzyna Szewczyk, Tadeusz Krzaczek, Tomasz Łopatyński, Urszula GawlikDziki & Christian Zidorn (2014): Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.938335 To link to this article: http://dx.doi.org/10.1080/14786419.2014.938335
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.
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This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions
Natural Product Research, 2014 http://dx.doi.org/10.1080/14786419.2014.938335
SHORT COMMUNICATION Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity Katarzyna Szewczyka*, Tadeusz Krzaczekab, Tomasz Łopatyn´skic, Urszula Gawlik-Dzikid and Christian Zidorne
Downloaded by [Florida International University] at 11:42 01 September 2014
a
Department of Pharmaceutical Botany, Medical University of Lublin, Chodz´ki 1 St, 20-093 Lublin, Poland; bInstitute of Medicine, The State Higher School of Computer Science and Business Administration in Lomza, Akademicka 14 St, 18-400 Łomz˙a, Poland; cChair and Department of Trauma Surgery and Emergency Medicine, Medical University of Lublin, Staszica 16 St, 20-081 Lublin, Poland; dDepartment of Biochemistry and Food Chemistry, University of Life Sciences, Skromna 8, Lublin, Poland; eInstitut fu¨r Pharmazie der Universita¨t Innsbruck, Abteilung Pharmakognosie, Innrain 80/82, A-6020 Innsbruck, Austria (Received 24 November 2013; final version received 22 June 2014) Seven flavonoids new for the genus Jovibarba, kaempferol 1, kaempferol 3-Ogalactopyranosyl-(1 ! 2)-O-a-L -rhamnopyranoside 2, kaempferol 3-O-b-D -glucoside 3, kaempferol 3-O-a-L -rhamnopyranosyl-7-O-a-D -glucofuranosyl-(1 ! 2)-O-a-L rhamnopyranoside 4, kaempferol 3-O-b-D -glucopyranoside-7-O-a-L -rhamnopyranoside 5, kaempferol 3,7,40 -O-trimethyl ether 6 and quercetin 7, were isolated from fresh and dried leaves of J. ovibarba globifera subsp. globifera. The structures of these compounds were established by analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. All of the flavonoids are reported for the first time from the investigated taxon. In addition the antioxidant activities in DPPH test of selected compounds were evaluated. Keywords: Jovibarba globifera; Jovibarba sobolifera; Sempervivum; Crassulaceae; flavonoids; antioxidant activity
1. Introduction Jovibarba globifera (L.) J. Parnell subsp. globifera [Jovibarba sobolifera (Sims) Opiz] is a calcifuge succulent perennial rosette herb occurring from central and south-east Europe southwards to north Albania, and extending to the south-west Alps and to north-west and central Russia (Parnell & Favarager 1993). Species from the genus Jovibarba were previously included in the genus Sempervivum L.; and studies on J. sobolifera have been stimulated by the biological activity of Sempervivum species (Stevens et al. 1996). Sempervivum species are used in folk medicine for the treatment of ear inflammations (Ke´ry et al. 1993). Moreover, tea prepared from leaves of Sempervivum tectorum L. is recommended for the treatment of ulcers. S. tectorum extract reduced lipid levels in rats and showed antimicrobial and in vitro antioxidant properties (Stevens et al. 1996; Abram & Donko 1999; Sˇentjurc et al. 2003). In earlier publications, we reported about phenolic acids, polysaccharides, phytosterols and triterpenoids from J. globifera subsp. globifera [as J. sobolifera ] (Szewczyk & Krzaczek 2004a, ` . Lo¨ve & 2004b). Apart from one report on flavonoid aglycones of Jovibarba heuffelii (Schott) A
*Corresponding author. Email: [email protected] q 2014 Taylor & Francis
2
K. Szewczyk et al.
D. Lo¨ve (Stevens et al. 1996) and a report on TLC analytics of triterpenoids in J. globifera (Szewczyk et al. 2009), there are no additional reports on the phytochemistry of the genus Jovibarba.
Downloaded by [Florida International University] at 11:42 01 September 2014
2. Results and discussion 2.1. Identification of isolated flavonoids In the course of a phytochemical study of the methanolic extracts from fresh and dried leaves of J. sobolifera, seven flavonoids were isolated. Kaempferol 1 (391.4 mg) (Lin et al. 2000), kaempferol 3-O-galactopyranosyl-(1 ! 2)-O-a-L -rhamnopyranoside 2 (5.9 mg) (Harborne 1999), kaempferol 3-O-b-D -glucoside 3 (27.1 mg) (Lee et al. 2004; Demirezer et al. 2006), kaempferol 3-O-a-L -rhamnopyranosyl-7-O-a-D -glucofuranosyl-(1 ! 2)-O-a-L -rhamnopyranoside 4 (41.7 mg) (Ku¨c u¨kislamog˘lu et al. 2000), kaempferol 3-O-b-D -glucopyranoside-7-O¨ zden et al. 1998), kaempferol 3,7,40 -O-trimethyl ether 6 a-L -rhamnopyranoside 5 (21.3 mg) (O (16.9 mg) (Stevens et al. 1995) and quercetin 7 (13.4 mg) (Stevens et al. 1996; Lee et al. 2004) OH
OH HO
O
HO
OH OH
OH OH
O
O
O
H
O
H OH
H
H
OH
1
O
H
CH2
H OH OH H
HO H 3C
H
OH
CH3 H
O
O H
H
OH O
OH OH
HO HO
O
CH3 OH
O
O
H OH
O
OH
H H
O
HC3
O
O OH H
OH
OH
5
O O
CH3 6
OH OH
O
O
H
H
OH OH
H
4
OH
HO
OH
O
H
O
O
O OH H
O
OH
H
OH
O
CH3
OH
O
3
OH
H
O-GLC
HO
OH O
OH
H
2
O
HO
H
OH
O 7
Figure 1. Structures of the isolated compounds 1– 7 from J. globifera.
CH3
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were isolated using standard chromatographic techniques (column and paper chromatography, TLC and HPLC) and their structures were determined based on NMR and MS data as well as by comparison with literature data of the above and related compounds. The structures of all isolated compounds are shown in Figure 1.
Downloaded by [Florida International University] at 11:42 01 September 2014
2.2. Antioxidant activities The antioxidant activities of the five isolated compounds were determined employing the DPPH (2.2-diphenyl-1-picryl-hydrazyl) assay. The obtained results are presented in Supplementary Table S1. Among the analysed flavonoids, kaempferol 1 (IC50 ¼ 3.97 ^ 0.10 mg/mL) and quercetin 7 (IC50 ¼ 4.53 ^ 0.10 mg/mL) exhibited similar antioxidant activity comparable to L ascorbic acid (IC50 ¼ 2.13 ^ 0.08 mg/mL) which was used as a positive control. The activity of compound 5 (IC50 ¼ 7.35 ^ 0.20 mg/mL) was also high. Compounds 3 and 4 showed weak antioxidant activities. These results showed that among compounds obtained from J. sobolifera leaves, flavonoid aglycones had comparatively higher antioxidant activity than their derivatives. The activity of compound 5 is in accordance with results reported for kaempferol 3-O-b-D glucopyranoside-7-O-a-L -rhamnopyranoside isolated from Bryophyllum pinnatum (Lam.) Kurz (IC50 ¼ 2.28 mg/mL) in comparison to L -ascorbic acid (IC50 ¼ 0.96 mg/mL) by Tatsimo et al. (2012). In an earlier publication, we reported the antioxidant properties of crude methanolic extracts from different parts of J. sobolifera (Szewczyk et al. 2012). 3. Conclusion All of the flavonoids are described for the first time from the investigated species. After acidic hydrolysis, kaempferol and myricetin were identified in extracts of J. heuffelii (Stevens et al. 1996); this is currently the only report also dealing with flavonoids in the genus Jovibarba. Stevens et al. (1996) moreover reported (also after acidic hydrolysis) kaempferol, herbacetin, quercetin and myricetin in various species of the closely related genus Sempervivum. Interestingly, kaempferol 3-O-b-D -glucopyranoside-7-O-a-L -rhamnopyranoside 5 has been recently also identified as the main flavonoid of S. tectorum leaf juice. This is the first report about the antioxidant activity of flavonoids isolated from J. sobolifera. The results obtained in this study indicate that flavonoid aglycones exhibit a stronger activity against DPPHz radicals than the isolated flavonoid glycosides and that compounds from J. sobolifera have pronounced antioxidant activity. Supplementary material Supplementary material relating to this article is available online, alongside Table S1. References Abram V, Donko M. 1999. Tentative identification of polyphenols in Sempervivum tectorum and assessment of the antimicrobial activity of Sempervivum L. J Agri Food Chem. 47:485–489. ¨ , Gu¨rbu¨z F, Gu¨venalp Z, Stro¨ch K, Zeeck A. 2006. Iridoids, flavonoids and monoterpene glycosides from Demirezer LO Galium verum subsp. verum. Turk J Chem. 30:525–534. Harborne JB. 1999. The flavonoids: advances in research since 1986. New York: Chapman & Hall. Ke´ry A, Petri G, Bla´zovics A, Pro´nai L, Fehe´r J. 1993. A natural antioxidant extract from Sempervivum tectorum. Phythother Res. 7:95– 97. Ku¨c u¨kislamog˘lu M, Yayli N, S¸entu¨rk HB, Genc H. 2000. Flavonol glycosides from Consolida armeniaca. Turk J Chem. 24:191–197. Lee JH, Ku CH, Baek NJ, Kim SH, Park HW, Kim DK. 2004. Phytochemical constituents from Diodia teres. Archiv Pharm Res. 27:40–43.
Downloaded by [Florida International University] at 11:42 01 September 2014
4
K. Szewczyk et al.
Lin YL, Wang WY, Kuo YH, Chen CF. 2000. J Chin Soc. 47:247–251. ¨ zden S, Drut N, Toki K, Saito N, Honda T. 1998. Acylated kaempferol glycosides from the flowers of Delphinium O formosum. Phytochemistry. 49:241–245. Parnell J, Favarger C. 1993. Jovibarba Opiz. In: Tutin TG, Burges NA, Chater AO, Edmondoson JR, Heywood VH, Moore DM, Valentine DH, Walters SM, Webb DA, editors. Flora Europaea. 2nd, Vol. 1. Cambridge: Cambridge University Press; p. 428–429. Sˇentjurc M, Nemec M, Connor HD, Abram V. 2003. Antioxidant activity of Sempervivum tectorum and its components. J Agric Food Chem. 51:2766–2771. Stevens JF, Hart H, Wollenweber E. 1995. The systematic and evolutionary significance of exudate flavonoids in Aeonium. Phytochemistry. 39:805– 813. Stevens JF, Hart H, Elema ET, Bolck A. 1996. Flavonoid variation in Eurasian Sedum and Sempervivum. Phytochemistry. 41:503–512. Szewczyk K, Komsta L, Skalska-Kamin´ska A. 2009. Densitometric HPTLC method for analysis of triterpenoids in the leaves of Jovibarba sobolifera (Sims.) Opiz (hen and chickens houseleek). J Planar Chromatogr - Modern TLC. 22:371–373. Szewczyk K, Krzaczek T. 2004a. Sterols in leaves and roots of Jovibarba sobolifera (Sims.) Opiz (hen and chickens houseleek). Herb Polon. 50:28–32. Szewczyk K, Krzaczek T. 2004b. Phenolic acids in leaves and roots from Jovibarba sobolifera (Sims.) Opiz. Herb Polon. 50:37–41. Szewczyk K, Smolarz HD, Gawlik-Dziki U. 2012. Antioxidant properties of three species from Crassulaceae family. Int J Pharm Pharma Sci. 4:107–108. Tatsimo SJN, Tamokou JD, Havyarimana L, Csupor D, Forgo P, Hohmann J, Kuiate JR, Tane P. 2012. Antimicrobial and antioxidant activity of kaempferol rhamnoside derivatives from Bryophyllum pinnatum. BMC Res Notes. 5:158–163.
Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20
Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity a
ab
d
e
c
Katarzyna Szewczyk , Tadeusz Krzaczek , Tomasz Łopatyński , Urszula Gawlik-Dziki & Christian Zidorn a
Department of Pharmaceutical Botany, Medical University of Lublin, Chodźki 1 St, 20-093 Lublin, Poland b
Institute of Medicine, The State Higher School of Computer Science and Business Administration in Lomza, Akademicka 14 St, 18-400 Łomża, Poland c
Chair and Department of Trauma Surgery and Emergency Medicine, Medical University of Lublin, Staszica 16 St, 20-081 Lublin, Poland d
Department of Biochemistry and Food Chemistry, University of Life Sciences, Skromna 8, Lublin, Poland e
Institut für Pharmazie der Universität Innsbruck, Abteilung Pharmakognosie, Innrain 80/82, A-6020 Innsbruck, Austria Published online: 17 Jul 2014. To cite this article: Katarzyna Szewczyk, Tadeusz Krzaczek, Tomasz Łopatyński, Urszula GawlikDziki & Christian Zidorn (2014): Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.938335 To link to this article: http://dx.doi.org/10.1080/14786419.2014.938335
PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.
Downloaded by [Florida International University] at 11:42 01 September 2014
This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions
Natural Product Research, 2014 http://dx.doi.org/10.1080/14786419.2014.938335
SHORT COMMUNICATION Flavonoids from Jovibarba globifera (Crassulaceae) rosette leaves and their antioxidant activity Katarzyna Szewczyka*, Tadeusz Krzaczekab, Tomasz Łopatyn´skic, Urszula Gawlik-Dzikid and Christian Zidorne
Downloaded by [Florida International University] at 11:42 01 September 2014
a
Department of Pharmaceutical Botany, Medical University of Lublin, Chodz´ki 1 St, 20-093 Lublin, Poland; bInstitute of Medicine, The State Higher School of Computer Science and Business Administration in Lomza, Akademicka 14 St, 18-400 Łomz˙a, Poland; cChair and Department of Trauma Surgery and Emergency Medicine, Medical University of Lublin, Staszica 16 St, 20-081 Lublin, Poland; dDepartment of Biochemistry and Food Chemistry, University of Life Sciences, Skromna 8, Lublin, Poland; eInstitut fu¨r Pharmazie der Universita¨t Innsbruck, Abteilung Pharmakognosie, Innrain 80/82, A-6020 Innsbruck, Austria (Received 24 November 2013; final version received 22 June 2014) Seven flavonoids new for the genus Jovibarba, kaempferol 1, kaempferol 3-Ogalactopyranosyl-(1 ! 2)-O-a-L -rhamnopyranoside 2, kaempferol 3-O-b-D -glucoside 3, kaempferol 3-O-a-L -rhamnopyranosyl-7-O-a-D -glucofuranosyl-(1 ! 2)-O-a-L rhamnopyranoside 4, kaempferol 3-O-b-D -glucopyranoside-7-O-a-L -rhamnopyranoside 5, kaempferol 3,7,40 -O-trimethyl ether 6 and quercetin 7, were isolated from fresh and dried leaves of J. ovibarba globifera subsp. globifera. The structures of these compounds were established by analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. All of the flavonoids are reported for the first time from the investigated taxon. In addition the antioxidant activities in DPPH test of selected compounds were evaluated. Keywords: Jovibarba globifera; Jovibarba sobolifera; Sempervivum; Crassulaceae; flavonoids; antioxidant activity
1. Introduction Jovibarba globifera (L.) J. Parnell subsp. globifera [Jovibarba sobolifera (Sims) Opiz] is a calcifuge succulent perennial rosette herb occurring from central and south-east Europe southwards to north Albania, and extending to the south-west Alps and to north-west and central Russia (Parnell & Favarager 1993). Species from the genus Jovibarba were previously included in the genus Sempervivum L.; and studies on J. sobolifera have been stimulated by the biological activity of Sempervivum species (Stevens et al. 1996). Sempervivum species are used in folk medicine for the treatment of ear inflammations (Ke´ry et al. 1993). Moreover, tea prepared from leaves of Sempervivum tectorum L. is recommended for the treatment of ulcers. S. tectorum extract reduced lipid levels in rats and showed antimicrobial and in vitro antioxidant properties (Stevens et al. 1996; Abram & Donko 1999; Sˇentjurc et al. 2003). In earlier publications, we reported about phenolic acids, polysaccharides, phytosterols and triterpenoids from J. globifera subsp. globifera [as J. sobolifera ] (Szewczyk & Krzaczek 2004a, ` . Lo¨ve & 2004b). Apart from one report on flavonoid aglycones of Jovibarba heuffelii (Schott) A
*Corresponding author. Email: [email protected] q 2014 Taylor & Francis
2
K. Szewczyk et al.
D. Lo¨ve (Stevens et al. 1996) and a report on TLC analytics of triterpenoids in J. globifera (Szewczyk et al. 2009), there are no additional reports on the phytochemistry of the genus Jovibarba.
Downloaded by [Florida International University] at 11:42 01 September 2014
2. Results and discussion 2.1. Identification of isolated flavonoids In the course of a phytochemical study of the methanolic extracts from fresh and dried leaves of J. sobolifera, seven flavonoids were isolated. Kaempferol 1 (391.4 mg) (Lin et al. 2000), kaempferol 3-O-galactopyranosyl-(1 ! 2)-O-a-L -rhamnopyranoside 2 (5.9 mg) (Harborne 1999), kaempferol 3-O-b-D -glucoside 3 (27.1 mg) (Lee et al. 2004; Demirezer et al. 2006), kaempferol 3-O-a-L -rhamnopyranosyl-7-O-a-D -glucofuranosyl-(1 ! 2)-O-a-L -rhamnopyranoside 4 (41.7 mg) (Ku¨c u¨kislamog˘lu et al. 2000), kaempferol 3-O-b-D -glucopyranoside-7-O¨ zden et al. 1998), kaempferol 3,7,40 -O-trimethyl ether 6 a-L -rhamnopyranoside 5 (21.3 mg) (O (16.9 mg) (Stevens et al. 1995) and quercetin 7 (13.4 mg) (Stevens et al. 1996; Lee et al. 2004) OH
OH HO
O
HO
OH OH
OH OH
O
O
O
H
O
H OH
H
H
OH
1
O
H
CH2
H OH OH H
HO H 3C
H
OH
CH3 H
O
O H
H
OH O
OH OH
HO HO
O
CH3 OH
O
O
H OH
O
OH
H H
O
HC3
O
O OH H
OH
OH
5
O O
CH3 6
OH OH
O
O
H
H
OH OH
H
4
OH
HO
OH
O
H
O
O
O OH H
O
OH
H
OH
O
CH3
OH
O
3
OH
H
O-GLC
HO
OH O
OH
H
2
O
HO
H
OH
O 7
Figure 1. Structures of the isolated compounds 1– 7 from J. globifera.
CH3
Natural Product Research
3
were isolated using standard chromatographic techniques (column and paper chromatography, TLC and HPLC) and their structures were determined based on NMR and MS data as well as by comparison with literature data of the above and related compounds. The structures of all isolated compounds are shown in Figure 1.
Downloaded by [Florida International University] at 11:42 01 September 2014
2.2. Antioxidant activities The antioxidant activities of the five isolated compounds were determined employing the DPPH (2.2-diphenyl-1-picryl-hydrazyl) assay. The obtained results are presented in Supplementary Table S1. Among the analysed flavonoids, kaempferol 1 (IC50 ¼ 3.97 ^ 0.10 mg/mL) and quercetin 7 (IC50 ¼ 4.53 ^ 0.10 mg/mL) exhibited similar antioxidant activity comparable to L ascorbic acid (IC50 ¼ 2.13 ^ 0.08 mg/mL) which was used as a positive control. The activity of compound 5 (IC50 ¼ 7.35 ^ 0.20 mg/mL) was also high. Compounds 3 and 4 showed weak antioxidant activities. These results showed that among compounds obtained from J. sobolifera leaves, flavonoid aglycones had comparatively higher antioxidant activity than their derivatives. The activity of compound 5 is in accordance with results reported for kaempferol 3-O-b-D glucopyranoside-7-O-a-L -rhamnopyranoside isolated from Bryophyllum pinnatum (Lam.) Kurz (IC50 ¼ 2.28 mg/mL) in comparison to L -ascorbic acid (IC50 ¼ 0.96 mg/mL) by Tatsimo et al. (2012). In an earlier publication, we reported the antioxidant properties of crude methanolic extracts from different parts of J. sobolifera (Szewczyk et al. 2012). 3. Conclusion All of the flavonoids are described for the first time from the investigated species. After acidic hydrolysis, kaempferol and myricetin were identified in extracts of J. heuffelii (Stevens et al. 1996); this is currently the only report also dealing with flavonoids in the genus Jovibarba. Stevens et al. (1996) moreover reported (also after acidic hydrolysis) kaempferol, herbacetin, quercetin and myricetin in various species of the closely related genus Sempervivum. Interestingly, kaempferol 3-O-b-D -glucopyranoside-7-O-a-L -rhamnopyranoside 5 has been recently also identified as the main flavonoid of S. tectorum leaf juice. This is the first report about the antioxidant activity of flavonoids isolated from J. sobolifera. The results obtained in this study indicate that flavonoid aglycones exhibit a stronger activity against DPPHz radicals than the isolated flavonoid glycosides and that compounds from J. sobolifera have pronounced antioxidant activity. Supplementary material Supplementary material relating to this article is available online, alongside Table S1. References Abram V, Donko M. 1999. Tentative identification of polyphenols in Sempervivum tectorum and assessment of the antimicrobial activity of Sempervivum L. J Agri Food Chem. 47:485–489. ¨ , Gu¨rbu¨z F, Gu¨venalp Z, Stro¨ch K, Zeeck A. 2006. Iridoids, flavonoids and monoterpene glycosides from Demirezer LO Galium verum subsp. verum. Turk J Chem. 30:525–534. Harborne JB. 1999. The flavonoids: advances in research since 1986. New York: Chapman & Hall. Ke´ry A, Petri G, Bla´zovics A, Pro´nai L, Fehe´r J. 1993. A natural antioxidant extract from Sempervivum tectorum. Phythother Res. 7:95– 97. Ku¨c u¨kislamog˘lu M, Yayli N, S¸entu¨rk HB, Genc H. 2000. Flavonol glycosides from Consolida armeniaca. Turk J Chem. 24:191–197. Lee JH, Ku CH, Baek NJ, Kim SH, Park HW, Kim DK. 2004. Phytochemical constituents from Diodia teres. Archiv Pharm Res. 27:40–43.
Downloaded by [Florida International University] at 11:42 01 September 2014
4
K. Szewczyk et al.
Lin YL, Wang WY, Kuo YH, Chen CF. 2000. J Chin Soc. 47:247–251. ¨ zden S, Drut N, Toki K, Saito N, Honda T. 1998. Acylated kaempferol glycosides from the flowers of Delphinium O formosum. Phytochemistry. 49:241–245. Parnell J, Favarger C. 1993. Jovibarba Opiz. In: Tutin TG, Burges NA, Chater AO, Edmondoson JR, Heywood VH, Moore DM, Valentine DH, Walters SM, Webb DA, editors. Flora Europaea. 2nd, Vol. 1. Cambridge: Cambridge University Press; p. 428–429. Sˇentjurc M, Nemec M, Connor HD, Abram V. 2003. Antioxidant activity of Sempervivum tectorum and its components. J Agric Food Chem. 51:2766–2771. Stevens JF, Hart H, Wollenweber E. 1995. The systematic and evolutionary significance of exudate flavonoids in Aeonium. Phytochemistry. 39:805– 813. Stevens JF, Hart H, Elema ET, Bolck A. 1996. Flavonoid variation in Eurasian Sedum and Sempervivum. Phytochemistry. 41:503–512. Szewczyk K, Komsta L, Skalska-Kamin´ska A. 2009. Densitometric HPTLC method for analysis of triterpenoids in the leaves of Jovibarba sobolifera (Sims.) Opiz (hen and chickens houseleek). J Planar Chromatogr - Modern TLC. 22:371–373. Szewczyk K, Krzaczek T. 2004a. Sterols in leaves and roots of Jovibarba sobolifera (Sims.) Opiz (hen and chickens houseleek). Herb Polon. 50:28–32. Szewczyk K, Krzaczek T. 2004b. Phenolic acids in leaves and roots from Jovibarba sobolifera (Sims.) Opiz. Herb Polon. 50:37–41. Szewczyk K, Smolarz HD, Gawlik-Dziki U. 2012. Antioxidant properties of three species from Crassulaceae family. Int J Pharm Pharma Sci. 4:107–108. Tatsimo SJN, Tamokou JD, Havyarimana L, Csupor D, Forgo P, Hohmann J, Kuiate JR, Tane P. 2012. Antimicrobial and antioxidant activity of kaempferol rhamnoside derivatives from Bryophyllum pinnatum. BMC Res Notes. 5:158–163.
