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Flavonoid glycosides from Reseda villosa (Resedaceae)
Biochemical Systematics and Ecology 34 (2006) 777e779 www.elsevier.com/locate/biochemsyseco
Flavonoid glycosides from Reseda villosa (Resedaceae) D. Berrahal a, A. Kabouche a, Z. Kabouche a,*, C. Bruneau b a
Laboratoire d’Obtention de Substances The´rapeutiques (LOST), Faculte´ des Sciences, Universite´ Mentouri e Constantine, Campus Chaabet Ersas, 25000 Constantine, Algeria b Universite´ de Rennes 1, U.M.R./C.N.R.S. N 6509, Campus de Beaulieu, 35042 Rennes Cedex, France Received 23 May 2006; accepted 1 June 2006
Keywords: Reseda villosa; Resedaceae; Flavonoid glycosides
1. Subject and source Reseda villosa, an endemic species of the Reseda genus (Resedaceae), was collected from Ghardaia (Septentrional Algerian Sahara) in mars 2002. The plant material was authentified by Prof. Ge´rard De Belair (University of Annaba, Algeria) and a voucher specimen (LOST/ZKAK Rv/03/02) was deposited at the herbarium of the Faculty of Sciences, University Mentouri-Constantine and at the Musee Botanique de la ville d’Angers, France (MBAng2005.12).
2. Previous work There are no reports from the endemic plant R. villosa.
3. Present study We report here from aerial parts of R. villosa five flavonoid glycosides, quercetin-7-O-a-L-rhamnosyl-3-O-b-Dglucoside, isorhamnetin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside, kaempferol-7-O-a-L-rhamnoside, kaemferol-7-Oa-L-rhamnosyl-3-O-b-D-glucoside and kaemferol-3,7-O-a-L-dirhamnoside, the latter is reported for the first time from the Reseda genus. Air-dried and powdered aerial parts (1 kg) of R. villosa were macerated in a methanolic solution (70%), the residue was filtered, concentrated then successively extracted with petroleum ether, dichloromethane, ethyl acetate and n-butanol. The butanolic extract was concentrated under reduced pressure and column chromatographed on polyamid SC6 with a gradient of tolueneeMeOH with increasing polarity. Paper chromatography using AcOH (15%) leaded to kaempferol-7-O-a-L-rhamnoside while preparative TLC on polyamid DC6 using H2Oe MeOHeMethylethylcetoneeAcetylacetone (13:3:3:1) leaded to quercetin-7-O-a-L-rhamnosyl-3-O-b-D-glucoside, * Corresponding author. Tel./fax: þ213 31 81 88 59. E-mail address: [email protected] (Z. Kabouche). 0305-1978/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved. doi:10.1016/j.bse.2006.06.004
778
D. Berrahal et al. / Biochemical Systematics and Ecology 34 (2006) 777e779
isorhamnetin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside, kaemferol-7-O-a-L-rhamnosyl-3-O-b-D-glucoside and kaemferol3,7-O-a-L-dirhamnoside. 4. Chemotaxonomic significance The Resedaceae are represented by six genus, five of them namely, Reseda, Caylusea, Oligomeris, Ochradenus, Randonia are distributed in the Saharian regions (Ozenda, 1958). The Reseda genus is found in the Mediterranean and the South Western Asian areas (Lawrence, 1969). In Algeria, there are 22 species and subspecies, two of them, R. villosa and Reseda arabica, are endemic to the Septentrional Sahara (Quezel and Santa, 1963; Ozenda, 1958). Eight flavones, 15 flavonols and one isoflavone have been reported from the Reseda genus. It appears that flavones, apigenin and its 7-O-glucoside derivative and luteolin and its derivatives, 7-O-glucoside and 30 -O-glucoside are characteristic to the Egyptian species Reseda muricata (El-Sayed et al., 2001) and Reseda pruinosa (Makboul et al., 1989) and the Uzbek species Reseda luteola (Batirov et al., 1979; Geiger and Krumbein, 1973). The diglycoside derivative, luteolin-30 ,7-O-b-D-diglucoside was found in R. luteola (Geiger and Krumbein, 1973) and R. luteola L. (Cristea et al., 2003) while luteolin-7-rutinoside was reported from Reseda gredensis (Granda and Gomez-Serranillos, 1970). Aglycone flavonols, kaempferol and quercetin, were isolated from the Mediterranean species R. muricata (ElSayed et al., 2001), Reseda odorata (Guyonnet, 1973) and Reseda phyteuma (Susplugas et al., 1984), isorhamnetin was reported from the Mediterranean species R. odorata and Reseda lutea (Plouvier, 1966). Flavonol monoglycosides, 7-O-rhamnoside, 7-O-glucoside and 3-O-glucoside were found in three Reseda species. Kaempferol-7-O-a-L-rhamnoside was reported from R. pruinosa (Makboul et al., 1989), kaempferol-7-O-b-D-glucoside, kaempferol-3-O-a-L-rhamnoside and quercetin-7-O-b-D-glucoside were found in R. muricata which is the single species containing a 7-O-coumaroylglucoside and a kaempferol trioside (El-Sayed et al., 2001). Flavonol diglycosides of kaempferol, quercetin and isorhamnetin, were reported from four species. Kaempferol-7-O-a-L-rhamno-3-O-b-D-glucoside was found in R. luteola (Yuldashev et al., 1996), quercetin-7-O-a-Lrhamnosyl-3-O-b-D-glucoside was isolated from the species R. lutea (Rzadkowska-Bodalska, 1969). Isorhamnetin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside (Plouvier, 1970) was reported from R. lutea and R. odorata, which contained isorhamnetin-3-O-b-D-glucosyl-40 -a-L-rhamnoside also reported from R. gredensis (Granda and Gomez-Serranillos, 1970). Isorhamnetin-3-O-rutinoside was reported only from R. pruinosa del. (Makboul et al., 1989). The single isoflavone, daidzein, was found in R. luteola (Yuldashev et al., 1996). We have isolated five flavonol-7-O-rhamnosides from R. villosa. One monoglycoside, Kaemferol-7-O-a-L-rhamnoside, also reported from R. pruinosa (Makboul et al., 1989), and four 3-O-glycosides namely, kaempferol-7-O-a-Lrhamnosyl-3-O-b-D-glucoside, previously reported from R. luteola (Yuldashev et al., 1996), quercetin-7-O-a-L-rhamnosiyl-3-O-a-L-rhamnoside and isorhamnotin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside, also reported from R. lutea (Rzadkowska-Bodalska, 1969), R. luteola (Yuldashev et al., 1996) and R. odorata (Plouvier, 1970), respectively, and kaempferol-3,7-O-a-L-dirhamnoside which is isolated for the first time from the Reseda genus. Acknowledgments The authors would like to thank the National Health Research Agency, Oran Algeria (A.N.D.R.S) for the financial support. References Batirov, E.Kh., Tadzhibaev, M.M., Malikov, V.M., 1979. Khim. Prir. Soedin. 5, 728. Cristea, D., Bareau, I., Vilarem, G., 2003. Dyes and Pigments 57, 267. El-Sayed, N.H., Omara, N.M., Yousef, A.K., Farag, A.M., Mabry, T.J., 2001. Phytochemistry 57, 575. Geiger, H., Krumbein, B., 1973. Z. Naturforsch. Sect. C J. Biosci. 28, 773. Granda, P.E., Gomez-Serranillos, M., 1970. Galen. Acta 23, 205. Guyonnet, C., 1973. C. R. Acad. Sci. Ser. D 277, 1993. Lawrence, G.H., 1969. Classification des plantes. Maison de la pense´e arabe, Beyrouth. Makboul, M.A., Abdel-Baky, A.M., Ramadan, M.A., 1989. Bull. Fac. Sci. 18, 1.
D. Berrahal et al. / Biochemical Systematics and Ecology 34 (2006) 777e779
779
Ozenda, P., 1958. Flore du Sahara Septentrional et Central. Editions CNRS, Paris (in French). Plouvier, V., 1966. C. R. Ser. D 262, 1368. Plouvier, V., 1970. C. R. Acad. Sci. Ser. D 270 (22), 2710. Quezel, P., Santa, S., 1963. Nouvelle flore de l’Alge´rie et des Re´gions De´sertiques et Me´ridionales, Tome II. Editions CNRS, Paris (in French). Rzadkowska-Bodalska, H., 1969. Pharm. Pharmacol. 21, 169. Susplugas, C., Susplugas, P., Masse, J.P., Bertez, C., 1984. Plant. Med. Phytother. 18, 62. Yuldashev, M.P., Batirov, E.Kh., Malikov, V.M., Yuldasheva, N.P., 1996. Khim. Prir. Soedin. 6, 949.
Flavonoid glycosides from Reseda villosa (Resedaceae) D. Berrahal a, A. Kabouche a, Z. Kabouche a,*, C. Bruneau b a
Laboratoire d’Obtention de Substances The´rapeutiques (LOST), Faculte´ des Sciences, Universite´ Mentouri e Constantine, Campus Chaabet Ersas, 25000 Constantine, Algeria b Universite´ de Rennes 1, U.M.R./C.N.R.S. N 6509, Campus de Beaulieu, 35042 Rennes Cedex, France Received 23 May 2006; accepted 1 June 2006
Keywords: Reseda villosa; Resedaceae; Flavonoid glycosides
1. Subject and source Reseda villosa, an endemic species of the Reseda genus (Resedaceae), was collected from Ghardaia (Septentrional Algerian Sahara) in mars 2002. The plant material was authentified by Prof. Ge´rard De Belair (University of Annaba, Algeria) and a voucher specimen (LOST/ZKAK Rv/03/02) was deposited at the herbarium of the Faculty of Sciences, University Mentouri-Constantine and at the Musee Botanique de la ville d’Angers, France (MBAng2005.12).
2. Previous work There are no reports from the endemic plant R. villosa.
3. Present study We report here from aerial parts of R. villosa five flavonoid glycosides, quercetin-7-O-a-L-rhamnosyl-3-O-b-Dglucoside, isorhamnetin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside, kaempferol-7-O-a-L-rhamnoside, kaemferol-7-Oa-L-rhamnosyl-3-O-b-D-glucoside and kaemferol-3,7-O-a-L-dirhamnoside, the latter is reported for the first time from the Reseda genus. Air-dried and powdered aerial parts (1 kg) of R. villosa were macerated in a methanolic solution (70%), the residue was filtered, concentrated then successively extracted with petroleum ether, dichloromethane, ethyl acetate and n-butanol. The butanolic extract was concentrated under reduced pressure and column chromatographed on polyamid SC6 with a gradient of tolueneeMeOH with increasing polarity. Paper chromatography using AcOH (15%) leaded to kaempferol-7-O-a-L-rhamnoside while preparative TLC on polyamid DC6 using H2Oe MeOHeMethylethylcetoneeAcetylacetone (13:3:3:1) leaded to quercetin-7-O-a-L-rhamnosyl-3-O-b-D-glucoside, * Corresponding author. Tel./fax: þ213 31 81 88 59. E-mail address: [email protected] (Z. Kabouche). 0305-1978/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved. doi:10.1016/j.bse.2006.06.004
778
D. Berrahal et al. / Biochemical Systematics and Ecology 34 (2006) 777e779
isorhamnetin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside, kaemferol-7-O-a-L-rhamnosyl-3-O-b-D-glucoside and kaemferol3,7-O-a-L-dirhamnoside. 4. Chemotaxonomic significance The Resedaceae are represented by six genus, five of them namely, Reseda, Caylusea, Oligomeris, Ochradenus, Randonia are distributed in the Saharian regions (Ozenda, 1958). The Reseda genus is found in the Mediterranean and the South Western Asian areas (Lawrence, 1969). In Algeria, there are 22 species and subspecies, two of them, R. villosa and Reseda arabica, are endemic to the Septentrional Sahara (Quezel and Santa, 1963; Ozenda, 1958). Eight flavones, 15 flavonols and one isoflavone have been reported from the Reseda genus. It appears that flavones, apigenin and its 7-O-glucoside derivative and luteolin and its derivatives, 7-O-glucoside and 30 -O-glucoside are characteristic to the Egyptian species Reseda muricata (El-Sayed et al., 2001) and Reseda pruinosa (Makboul et al., 1989) and the Uzbek species Reseda luteola (Batirov et al., 1979; Geiger and Krumbein, 1973). The diglycoside derivative, luteolin-30 ,7-O-b-D-diglucoside was found in R. luteola (Geiger and Krumbein, 1973) and R. luteola L. (Cristea et al., 2003) while luteolin-7-rutinoside was reported from Reseda gredensis (Granda and Gomez-Serranillos, 1970). Aglycone flavonols, kaempferol and quercetin, were isolated from the Mediterranean species R. muricata (ElSayed et al., 2001), Reseda odorata (Guyonnet, 1973) and Reseda phyteuma (Susplugas et al., 1984), isorhamnetin was reported from the Mediterranean species R. odorata and Reseda lutea (Plouvier, 1966). Flavonol monoglycosides, 7-O-rhamnoside, 7-O-glucoside and 3-O-glucoside were found in three Reseda species. Kaempferol-7-O-a-L-rhamnoside was reported from R. pruinosa (Makboul et al., 1989), kaempferol-7-O-b-D-glucoside, kaempferol-3-O-a-L-rhamnoside and quercetin-7-O-b-D-glucoside were found in R. muricata which is the single species containing a 7-O-coumaroylglucoside and a kaempferol trioside (El-Sayed et al., 2001). Flavonol diglycosides of kaempferol, quercetin and isorhamnetin, were reported from four species. Kaempferol-7-O-a-L-rhamno-3-O-b-D-glucoside was found in R. luteola (Yuldashev et al., 1996), quercetin-7-O-a-Lrhamnosyl-3-O-b-D-glucoside was isolated from the species R. lutea (Rzadkowska-Bodalska, 1969). Isorhamnetin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside (Plouvier, 1970) was reported from R. lutea and R. odorata, which contained isorhamnetin-3-O-b-D-glucosyl-40 -a-L-rhamnoside also reported from R. gredensis (Granda and Gomez-Serranillos, 1970). Isorhamnetin-3-O-rutinoside was reported only from R. pruinosa del. (Makboul et al., 1989). The single isoflavone, daidzein, was found in R. luteola (Yuldashev et al., 1996). We have isolated five flavonol-7-O-rhamnosides from R. villosa. One monoglycoside, Kaemferol-7-O-a-L-rhamnoside, also reported from R. pruinosa (Makboul et al., 1989), and four 3-O-glycosides namely, kaempferol-7-O-a-Lrhamnosyl-3-O-b-D-glucoside, previously reported from R. luteola (Yuldashev et al., 1996), quercetin-7-O-a-L-rhamnosiyl-3-O-a-L-rhamnoside and isorhamnotin-3-O-b-D-glucosyl-7-O-a-L-rhamnoside, also reported from R. lutea (Rzadkowska-Bodalska, 1969), R. luteola (Yuldashev et al., 1996) and R. odorata (Plouvier, 1970), respectively, and kaempferol-3,7-O-a-L-dirhamnoside which is isolated for the first time from the Reseda genus. Acknowledgments The authors would like to thank the National Health Research Agency, Oran Algeria (A.N.D.R.S) for the financial support. References Batirov, E.Kh., Tadzhibaev, M.M., Malikov, V.M., 1979. Khim. Prir. Soedin. 5, 728. Cristea, D., Bareau, I., Vilarem, G., 2003. Dyes and Pigments 57, 267. El-Sayed, N.H., Omara, N.M., Yousef, A.K., Farag, A.M., Mabry, T.J., 2001. Phytochemistry 57, 575. Geiger, H., Krumbein, B., 1973. Z. Naturforsch. Sect. C J. Biosci. 28, 773. Granda, P.E., Gomez-Serranillos, M., 1970. Galen. Acta 23, 205. Guyonnet, C., 1973. C. R. Acad. Sci. Ser. D 277, 1993. Lawrence, G.H., 1969. Classification des plantes. Maison de la pense´e arabe, Beyrouth. Makboul, M.A., Abdel-Baky, A.M., Ramadan, M.A., 1989. Bull. Fac. Sci. 18, 1.
D. Berrahal et al. / Biochemical Systematics and Ecology 34 (2006) 777e779
779
Ozenda, P., 1958. Flore du Sahara Septentrional et Central. Editions CNRS, Paris (in French). Plouvier, V., 1966. C. R. Ser. D 262, 1368. Plouvier, V., 1970. C. R. Acad. Sci. Ser. D 270 (22), 2710. Quezel, P., Santa, S., 1963. Nouvelle flore de l’Alge´rie et des Re´gions De´sertiques et Me´ridionales, Tome II. Editions CNRS, Paris (in French). Rzadkowska-Bodalska, H., 1969. Pharm. Pharmacol. 21, 169. Susplugas, C., Susplugas, P., Masse, J.P., Bertez, C., 1984. Plant. Med. Phytother. 18, 62. Yuldashev, M.P., Batirov, E.Kh., Malikov, V.M., Yuldasheva, N.P., 1996. Khim. Prir. Soedin. 6, 949.