Czytelnia Medyczna » Postępy Fitoterapii » 2/2006 » On the phytochemical investigation of the genus Gentiana used for the treatment of liver diseases in Mongolian Traditional Medicine¹

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Dencmaa Dungerdorj, S. Tsetsegmaa, S. Purevsuren, B. Bayasgalan

On the phytochemical investigation of the genus Gentiana used for the treatment of liver diseases in Mongolian Traditional Medicine¹

Medical University of Ulaan Baatar, Mongolia
Head of Department: Dencmaa Dungerdorj, M.D., DSc.

Summary
On the result of phytochemical investigation of 8 species of the genus Gentiana growing in Mongolia 27 xanthons, 15 flavonoids, 11 secoiridoids, 3 organic acids, totally more than 50 compounds were isolated and identified. From Gentiana barbata 8 xanthons, 2 secoiridoids, 2 flavonoids; from G. macrophylla 1 secoiridoid, 2 flavonoids; from G. decumbens 2 secoiridoids, 4 flavonoids; from G. algida 1 secoiridoid, 3 flavonoids; from G. acuta 6 xanthons, 1 secoiridoid, 3 flavonoids, 1 organic acid; from G. uniflora 2 xanthons, 1 organic acid; from G. azurium 6 xanthons, 3 secoiridoids, 1 flavonoid; from G. pulmonaria 5 xanthons, 1 secoiridoid were isolated. 7-O-β-D-glucopiranosyl-1-hydroxy-3,8-dimethoxyxanthon from Gentiana barbata, 1,3,5-trihydroxy-8-methoxyxanthon from G. azurium, 1-O-β-D-glucopiranosyl-3,5-dihydroxy-8-methoxyxanthon, 1-hydroxy-3-methoxy-5-acetoxy-8-acetyl-O-β-D-fructofurano-sylxanthon from G. pulmonaria were novel compounds found in nature for the first time and their structures were elucidated by spectral analysis.

Key words: genus gentiana, chemical composition, liver diseases.

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According to the last 10 years research, digestive organ system are on the second places illnesses of total population of Mongolia and viral hepatitis of liver tumor are very common in the country. Statistic data show that 35.3% of cancer is liver cancer and 29% of contagious disease is liver viral hepatitis. From ancient times Mongolians treated liver diseases and the liver diseases were classified into 18 types in traditional medical books and 26 kind of prescriptions included about 101 raw materials which are prepared from mineral, plant and animal resources used in traditional treatment.

Many species of the genus Gentiana takes the main position among the raw materials of medicines used for the treatment of liver diseases.

There are more than 20 species of the genus Gentiana ( Gentianaceae), growing in Mongolian territory and 8 species of Gentiana, including Gentiana barbata (Froel), G. decumbens (L), G. macrophylla (Pall), G. algida (Pall), G. acuta (Michx), G. uniflora (Georgi), G. azurium Bunge, G. pulmonaria Turz have been phytochemically and pharmacologically investigated.

Gentiana species contain bio-active compounds such as alkaloids, tannins, flavonoids, organic acids, terpenoids and Mongolian researchers have extensively studied chemical composition of these plants since 1980. Flavonoid isoorientin was isolated from G. algida on the result of the chemical investigation done by Zorig et al. for the first time (1) and up to now more than 50 compounds, including 27 xanthons, 11 iridoids, 15 flavonoids, 3 organic acids have been isolated and identified by researchers of Chemical Institute, MAS, Institute of Traditional Medicine, and other institutes in Mongolia (Table 1).

Table 1. Isolated compounds from Gentiana species growing in Mongolia.

Investigatede species	Xanthons		Secoiridois	Flavonoids		Organic acids
Investigatede species	aglycons	glucosides	Secoiridois	aglycons	glucosides	Organic acids
Gentiana barbata	2	6	2	2	-	1
Gentiana macrophylla	-	-	1	-	2	-
Gentiana decumbens	-	-	2	-	4	-
Gentiana algida	-	-	1	1	2	-
Gentiana acuta	3	3	1	-	3	1
Gentiana uniflora	1	1	-	-	-	1
Gentiana azurium	4	2	3	-	1	-
Gentiana pulmonaria	2	3	1	-	-	-
Total	12	15	11	3	12	3
Total	27		11	15		3

Among these isolated compounds, xanthons are the main components and have attracted considerable attention and 27 xanthons isolated from above mentioned Gentiana apecies are shown in Table 2.

Table 2. Xanthons from Gentiana species.

Compounds	*G. barbata*	*G. acuta*	*G. uniflora*	*G. azurium*	*G. pulmonaria*
1-Hydroxy-3,7,8-trimethoxyxanthon	+				+
1,7-Dihydroxy-3,8-dimethoxyxanthon	+		+		+
1,3,5-Trihydroxy-8-methoxyxanthon				+
1,3,5,8-Tetramethoxyxanthon		+
1,5,8-Trihydroxy-3-methoxyxanthon		+		+
1,3,8-Trihydroxy-4,5-dimethoxyxanthon		+
7-O-β-D-Glucopiranosyl-1-hydroxy-3,8-dimethoxyxanthon	+
1-O-β-D-Glucopiranosyl-3,7,8-trimethoxyxanthon	+				+
1-O-β-D-Primverosyl-3,7,8-dimethoxyxanthon	+
1-O-Primverosyl-7-hydroxy-3,8-dimethoxyxanthon	+		+
2-C-β-D-Glucopiranosyl-1,3,6,7-tetramethoxyxanthon		+
8-O-β-D-Glucopiranosyl-1,5-dihydroxy-3-methoxyxanthon		+
8-O-β-D-Glucopiranosyl-1,3,5-trihydroxyxanthon		+
1-O-β-D-Glucopiranosyl-7-hydroxy-3,8-dimethoxyxanthon	+
1-O-β-Glucopiranosylxanthon	+
1,3,5-Trihydroxy-5-methoxyxanthon				+
1-O-β-D-Glucopiranosyl-3,5-dihydroxy-8-methoxyxanthon				+
1,3,5-Trihydroxy-8-methoxy-1-O-β-D-glucopiranosylxanthon	+			+
1-Hydroxy-3-methoxy-5-acetoxy-8-acetyl-O-β-D-fructofuranosylxanthon					+
1-Gentiobiosid-3,7,8-trimethoxyxanthon					+
Total	9	6	2	5	5

7-O-β-D-Glucopiranosyl-1-hydroxy-3,8-dimethoxyxanthon (I) from Gentiana barbata (Froel), 1,3,5-trihydroxy-8-methoxyxanthon (II), 1,O-β-D-glucopiranosyl-3,5-dihydroxy-8-methoxyxanthon (III) from G. azurium, 1-hydroxy-3-methoxy-5-acetoxy-8-acetyl-O-β-D-fructofuranosylxanthon (IV) from G. pulmonaria were novel compounds found in nature for the first time and their structures were elucidated by spectral analysis.

Although most of xanthon glycosides from Gentiana were O-glucosides, in which β-D-glucose and primeros (β-D-xylopiranosyl-(1-6)-β=D-glucopiranose) linked at C-1, two C-glycosides, each with β-D-glucose moiety at C-2 were isolated from G. acuta. All xanthous had substituents at C-3 and in connection with these substituents xanthons possess some pharmacological activities (2).

Secoiridoids isolated from the genus Gentiana, especially gentiopicrosid and svertiamarin in three species of it, give us a possibility to make a conclusion that secoiridoids might be a specific compound for this genus and further investigation to clarify it is very important.

Flavonoids are also main components of many species of the genus Gentiana and flavonoids shown in Table 3 were isolated from G. barbata, G. macrophylla, G. decumbens, G. algida and G. acuta.

Table 3. Flavonoids from Gentiana species.

Compounds	*G. barbata*	*G. macrophylla*	*G. decumbens*	*G. algida*	*G. azurium*	*G. acuta*
5,7,3´,4-Tetrahydroxyflavon	+					+
8-C-β-D-Glycopiranosyl-5,7,3´,4´-tetrahydroxyflavon						+
6-O-β-D-Glycopiranosyl-5,7,3´,4´-tetrahydroxyflavon		+	+	+		+
7-O-β-D-Glucopiranosyl-5,3´,4´-trihydroxyflavon						+
6-O-β-D-Glucopiranosyl-5,7,4´-trihydroxyflavon		+	+	+
4´-O-β-D-glucopiranosyl-6-C-β-D-glucopiranosyl-3,5,7-trimethoxyflavon			+
4´-O-β-D-glucopiranosyl-6-C-β-D-glucopiranosyl-3,7-dimethoxyflavon			+
5,7,3´,4´-Tetrahydroxy-6-C-β-D-glucopiranosylflavon					+
5,7,3´-Trihydroxy-4´-methoxyflavon	+
5,7,3´-Trihydroxyflavon				+

11 secoiridoids were isolated and identified from Gentiana species (Table 4).

Table 4. Secoiridoids from Gentiana species.

Gentiana species	Gentiopicrosid	Svertiamarin	Amarogentin	Amaropanin	Sverosid
G. barbata	+	+
G. macrophylla			+
G. decumbens	+		+
G. algida				+
G. acuta	+
G. azurium	+	+			+
G. uniflora		+

Anti-inflammatory, hepatoprotective, cholaretic, antioxidant activities of G. decumbens, G. macrophylla, G. acuta were determined by Mongolian researches and Gentsichol, Gepachol, Silodin preparations from them are successfully used for the treatmant of liver diseases (3-5).

¹Praca wygłoszona na Pierwszym Światowym Forum Naukowym pt. Etnomedycyna odpowiedzią na potrzeby XXI wieku, w Warszawie, w dniu 27 listopada 2004 r.
¹The paper was presented during the First World Forum of Science „Etnomedicine – an answer to the needy of 21st century” on 27.112004 held in Warsaw, Poland.

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Piśmiennictwo

1. Zorig O., Ouyngerel Z., Maslo O.: Isoorientin from Gentiana algida, Chem. Prir. Soed. 1980, 2, 253. 2. Chun-Nan-Lin: Synthesis and anti-inflammatory effects of xanthone deriatives. J. Pharm. Pharmacol. 1996, 48. 532. 3. Khishgee D.: Phytochemical investigation of 2 species of Gentiana used in Mongolian Traditional Medicine. Doctor Thesis, Med Univ. Ullan Baatar, Mongolia 1995, 36. 4. Tserendulam L.: Chemical and chemico-technological investigation of some species of the genus Bupleurum L. Doctor Thesis, Med Univ. Ullan Baatar, 1996. 5. Ouyngerel Z., Tserendulam L., Ambaga M., Dolgorsuren T.: Investigation of some hepatoprotective compounds. Conference Raport 27, Ullan Baatar, 1993, 90.

otrzymano: 2004-02-10
zaakceptowano do druku: 2006-06-02

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On the phytochemical investigation of the genus Gentiana used for the treatment of liver diseases in Mongolian Traditional Medicine1

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On the phytochemical investigation of the genus Gentiana used for the treatment of liver diseases in Mongolian Traditional Medicine¹