Some wild-growing plant species from Serbia and Montenegro

as the potential source of drugs

Photo: Mountain Orjen, Montenegro 2006.

Plovdiv, 2013.

Project 172053, 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”

Tara mountain

Montenegro mountains

Šar-Planina

(Šara Mountain)

Stara Planina

(Old mountain)

Deliblatska peščara

(Deliblato sand)

Srbija & Montenegro

Sićevačka klisura

(Sićevo gorge)

Photo Šavikin

Asteraceae

Tanacetum larvatum (Gris.)

Kanitz.

Highland plant species >1500

m, Komovi, Sinjajevina, Babji

Zub, Visitor, Prokletije

(Montenegro)

Montenegro

Karanfili mountains,

a view from Grbaja valley (ca. 1200 m)

Kotlovi ca. 1600 m Tanacetum larvatum

O

O

o

O

O

OH

H

O

O

OMe

OH

OMe

OH

HO

Aljančić, I. et al. Parthenolide from the Aerial Parts of

Tanacetum larvatum. Biochem. Syst. Ecol. (2001), 29, 655-

57.

parthenolide: >1% in leaves

and flowers

Extract (aerial parts): MeOH : Et2O : Pet Ether = 1:1:1

minor constituents:

tricin douglanine

Komovi

1H 200 MHz NMR(CDCl3): crude extract (Petrol ether / Et2O / MeOH

= 1:1:1) of the aerial arts of Tanacetum larvatum

parthenolide

српски: Повратић

Prophylaxis of

migraine headaches

Xanthones, secoiridoids and flavonoids (C-glucoflavones)

O

O

R5

OR8

R3O

OR1

R7

O

O

OGlc

H

O

O

OOH

HO

Glc

OH

OR

2. Gentianaceae

2.1. Gentiana dinarica Beck.

2.2. Gentianella austriaca (A&J Kerner) Holub

2.3. G. bulgarica (Velen.) Holub

2.4. G. albanica (Jav.) Holub

2.5. G. crispata (Vis.) Holub

Gentiana dinarica Beck. (Gentianaceae)

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.

N. Menković

O

O

O

H

R

O

OOR1

HOHO

HO

O

O

OGlc

H

O

O

O OR1OR

OH

HO

O

OH

HOOH

O

OOH

HO

Glc

OH

OR

Krstić, D. et al. Phytochemical investigation of Gentiana dinarica. Biochem. Syst.

Ecol. (2004), 32, 937–941.

1: R = H (sweroside)

2: R = OH; R1 = H (swertiamarin)

3: R = H; R1 =

4 (gentiopicrin)

5: R = Glc6-Xyl; R1 = H (norswertianin-1-O-primeveroside)

6: R = H; R1 = Glc6-Xyl (norswertianin-8-O-primeveroside)

7: R = H (isoorientin)

8: R = Glc (isoorientin-4’-O-glucoside)

MeOH Extraction: 1, 3, 4 – 8 (roots),

1, 2, 4, 7, 8 (aerial parts)

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.

(amarogentin)

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. austriaca (A&J Kerner) Holub)

Kopaonik,

Maljen,

Povlen, Tara,

Jablanik

Stara planina

(Serbia)

G. crispata

(Vis.) Holub

Hajla, Komovi,

Sinjajevina,

Prokletije

G. bulgarica (Velen.) Holub

G. albanica (Jav.) Holub

Hajla mountain

Hajla, Visitor

Genus Gentianella Moench

Aerial parts

HPLC (Chromatographic column, Zorbax SB-C18 5 mm,

250x4.6 mm i.d. (HP); flow rate 1 ml/min; mobile

phase, MeCNC+H2O (containing 1% 0.1 N H3PO4);

elution, combination of gradient and isocratic modes,

DAD 260 nm; Janković et al. 2005) of the MeOH extract of

G. albanica

Roots

MeOH extracts of the aerial parts of all four species

O

O

OR5

OR8

R3O

OR1

R4

R1

R3

R4

R5

R8

1 H H H H H demethylbellidifolin

2 H Me H H H bellidifolin

3 H H OMe Me H corymbiferin

4 H H H H Glc demethylbellidifolin-8-

O-glucoside

5 H Me H H Glc bellidifolin-8-O-

glucoside

6 Glc H OMe Me H corymbiferin-1-O-

glucoside

O

O R8OH

OR7

MeO

OR4

R4

R7

R8

7 Me Glc H veratriloside

8 Glc Me OH lanceoside

O

OOH

R7O

Glc

OH

R3'

9: R7 = H; R3’ = OH (isoorientin)

10: R7 = Me; R3’ = H (swertisin)

O

OOH

HO

OH

OGlc

11: campestroside

12: mangiferin

O

O

HO

OH

OHGlc

OH

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), 729-735.

Janković, T. et al. Radioprotective effects of Gentianella austriaca fractions and

polyphenolic constituents in human lymphocytes. Planta Med. (2008), 74(7), 736-740.

R3

R8

1 H H demethylbellidifolin

4 H Glc demethylbellidifolin-8-O-

glucoside

5 Me Glc bellidifolin-8-O-glucoside

O

OOH

MeO

Glc

OH

10 (swertisin)

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.

O

O

OH

OR8

R3O

OH

Eng: Gentian

Bg: Тинтява

Ser: Линцура

Traditional herbal medicinal product used

in mild dyseptic/gastrointestinal disorders,

and/or in temporary loss of appetite.

Gentiana lutea

Karanfili, Prokletije

The End