Some wild-growing plant species from Serbia and Montenegro as the potential source of drugs. Photo: Mountain Orjen, Montenegro Plovdiv, 2013.

Transcription

1 Some wild-growing plant species from Serbia and Montenegro as the potential source of drugs Photo: Mountain rjen, Montenegro Plovdiv, 2013.

2 Project , Ministry of Science and Techological Development, Serbia Bioactive natural products of wild growing, cultivated and edible plants: structure and bioactivity determination Dr. Ljubodrag Vujisić and Dr. Dejan Godjevac Faculty of Chemistry University of Belgrade Center for Chemistry Institute for Chemistry, Technology and Metallurgy Belgrade Department for Instrumental Analysis (founded 1966) former Center for Instrumental Analysis = CIA

3 Tara mountain Srbija & Montenegro Montenegro mountains Šar-Planina (Šara Mountain) Sićevačka klisura (Sićevo gorge) Stara Planina (ld mountain) Deliblatska peščara (Deliblato sand)

4 Asteraceae Tanacetum larvatum (Gris.) Kanitz. Montenegro Photo Šavikin Highland plant species >1500 m, Komovi, Sinjajevina, Babji Zub, Visitor, Prokletije (Montenegro)

5 Karanfili mountains, a view from Grbaja valley (ca m) Kotlovi ca m Tanacetum larvatum

6 Aljančić, I. et al. Parthenolide from the Aerial Parts of Tanacetum larvatum. Biochem. Syst. Ecol. (2001), 29, Extract (aerial parts): MeH : Et 2 : Pet Ether = 1:1:1 o parthenolide: >1% in leaves and flowers minor constituents: H Me H Komovi H Me H H douglanine tricin

7 1 H 200 MHz NMR(CDCl 3 ): crude extract (Petrol ether / Et 2 / MeH = 1:1:1) of the aerial arts of Tanacetum larvatum parthenolide

8 Prophylaxis of migraine headaches српски: Повратић

9 2. Gentianaceae 2.1. Gentiana dinarica Beck Gentianella austriaca (A&J Kerner) Holub 2.3. G. bulgarica (Velen.) Holub 2.4. G. albanica (Jav.) Holub 2.5. G. crispata (Vis.) Holub R 5 H R R 3 R 1 R 8 R7 H Glc H Glc H Xanthones, secoiridoids and flavonoids (C-glucoflavones)

10 Gentiana dinarica Beck. (Gentianaceae) N. Menković Drina canyon A rare perennial plant species growing on carbonate soils in subalpine and alpine regions Plant material (aerial parts and roots) was collected on the mountain Tara (~1300 m), west Serba.

11 Krstić, D. et al. Phytochemical investigation of Gentiana dinarica. Biochem. Syst. Ecol. (2004), 32, R MeH Extraction: 1, 3, 4 8 (roots), 1, 2, 4, 7, 8 (aerial parts) H R H H H H H R 1 1: R = H (sweroside) 2: R = H; R 1 = H (swertiamarin) 3: R = H; R 1 = H (amarogentin) H H H Glc 4 (gentiopicrin) H Glc R H R 1 7: R = H (isoorientin) 8: R = Glc (isoorientin-4 --glucoside) H 5: R = Glc 6 -Xyl; R 1 = H (norswertianin-1--primeveroside) 6: R = H; R 1 = Glc 6 -Xyl (norswertianin-8--primeveroside) The bitter principles (1-3), the usual constituents of the genus, stimulate secretion of gastric juices and bile, thus aiding apetite and digestion. They also exhibit various biological activities. Sweroside (1) is antihepatitic drug. Swertiamarin (2) and also sweroside (1) inhibit the growth of Bacillus cereus, B. subtilis, Citrobacter freundii and Escherichia coli. While 2 is also active against Proteus mirabilis and Serratia marcescens, 1 inhibits the growth of Staphylococcus epidermidis.

12 Genus Gentianella Moench The genus contains about 250 species distributed over all continents. In Serbia and Montenegro one can find six species The main secondary metabolites of the genus are xanthones, flavone-c-glucosides and secoiridoids. G. crispata (Vis.) Holub Hajla, Komovi, Sinjajevina, Prokletije G. albanica (Jav.) Holub Hajla mountain G. bulgarica (Velen.) Holub Hajla, Visitor Kopaonik, Maljen, Povlen, Tara, Jablanik Stara planina (Serbia) G. austriaca (A&J Kerner) Holub)

13 HPLC (Chromatographic column, Zorbax SB-C18 5 mm, 250x4.6 mm i.d. (HP); flow rate 1 ml/min; mobile phase, MeCNC+H 2 (containing 1% 0.1 N H 3 P 4 ); elution, combination of gradient and isocratic modes, DAD 260 nm; Janković et al. 2005) of the MeH extract of G. albanica Aerial parts Roots

14 Janković, T. et al.. Xanthones and C-glucosides from the aerial parts of four species of Gentianella from Serbia and Montenegro. Biochem. Syst. Ecol. (2005), 33(7), R 3 R 4 MeH extracts of the aerial parts of all four species R 5 R 4 Me R 7 R 1 R 8 H R 8 R 1 R 3 R 4 R 5 R 8 1 H H H H H demethylbellidifolin 2 H Me H H H bellidifolin 3 H H Me Me H corymbiferin 4 H H H H Glc demethylbellidifolin-8- -glucoside 5 H Me H H Glc bellidifolin-8-glucoside 6 Glc H Me Me H corymbiferin-1-glucoside R 4 R 7 R 8 7 Me Glc H veratriloside 8 Glc Me H lanceoside H H H Glc 11: campestroside R 3' H H H R 7 Glc H 9: R 7 = H; R 3 = H (isoorientin) 10: R 7 = Me; R 3 = H (swertisin) Glc H 12: mangiferin H

15 Janković, T. et al. Radioprotective effects of Gentianella austriaca fractions and polyphenolic constituents in human lymphocytes. Planta Med. (2008), 74(7), A pharmacological study involving radioprotective effects of Gentianella austriaca ether (EF) and methanolic fractions (MF) and polyphenolic constituents (1, 4, 5, 10) in human lymphocytes was undertaken. EF and MF showed better protection in treatment of human lymphocytes after g- irradiation than isolated compoundes. These results suggest that the antioxidative properties of polyphenols tested may contribute to the radioprotective effects of G. austriaca. H H R 3 Me H R 8 Glc H R 3 R 8 1 H H demethylbellidifolin 4 H Glc demethylbellidifolin-8-glucoside 5 Me Glc bellidifolin-8--glucoside 10 (swertisin)

16 Gentiana lutea Traditional herbal medicinal product used in mild dyseptic/gastrointestinal disorders, and/or in temporary loss of appetite. Eng: Gentian Bg: Тинтява Ser: Линцура

17 Karanfili, Prokletije The End