Pharmacological and analytical aspects of bergenin: a concise report

1. Pharmacological and analytical aspects of bergenin: a concise report 张 慧 2012213034 Asian Pacific Journal of Tropical Disease (2012) 163–167

2. Abstracts • Present review described the pharmacological activity, analytical methods and isolation techniquesof bergenin, which give an idea about the nature and activity of bergenin. • This review could be helpful to the researchers in the future for the development of new drugs for the treatment of various types of illness. • The data in the present review were collected from the available literature sources.

3. Contents 1. Introduction 2. Pharmacological activity 3. Physicochemical properties of bergenin 4. Chemical derivative of bergenin 5. Isolation of bergenin 6. Analytical techniques 7. Discussion

4. 1. Introduction Structure of bergenin.

5. 1. Introduction

6. Isolated from Bergenial crassifolia Mallotus philippinensis Corylopsis spicata Caesalpinia digyna Mallotus japonicus 1. Introduction • a colourless crystalline polyphenol • It is hydrolyzable tannin and an isocoumarin derivative with • three hydroxyl (OH) groups and two phenolic OH groups

7. 2.2 Antimicrobial activity 2.1 Antiinflammatory activity Bergenin 2. Pharmacological activity modulation of Th1/Th2 cytokine balance show anti-arthritic activity. Norbergenin inhibits the growth of the yeasts C. albicans, C.tropicalis, but presents lower activity against filamentous fungi Aspergillus flavus.

8. 2.3 Antioxidant activity 2.4 Cytotoxic activity 2.5 Effect of bergenin on bioavailability showed antioxidant activity in lipid peroxidation, superoxide and DPPH radical assays. Bergenin showed antiviral activity against herpes simplex virus type-1 in non cytotoxic concentrations. 2. Pharmacological activity bergenin-phospholipid complex(BPC)

9. extensive use 2. Pharmacological activity Bergenin exhibits various biological activities such as antiulcer, antifungal, immunomodulatory and burn wound healing. the lack of a sensitive assay for its determination in biological fluids in human

10. 3. Physicochemical properties of bergenin solid state characteristics octanol/water partition coefficient (Log P) Physicochemical properties solution stability solubility dissociation constant

11. RAE-1 Properties: White granular crystal, easily soluble in DMSO, pyridine, soluble in MeOH, insoluble in P. ether, CH2Cl2 and EtOAc. A dark spot under UV254 nm, no fluorescence under UV365 nm on silica gel TLC. Turn gray-blue in 2% FeCl3-EtOH, and drab yellow in 5% PMA-EtOH. Purity test: GF254 silica gel TLC RAE-1, 11.06 mg, 1H-NMR, in DMSO-d6 .

12. RAE-1 water peak solvent peak

13. RAE-1 5-OH,s 7-OH,s H-4,s

14. RAE-1 12-OH,d,5 Hz 16-OH,t 13-OH,d,5.3Hz H-9,d,10.8 Hz

15. RAE-1 OMe 16-Hb,dd,11.6Hz,4.4Hz H-14,dd,9.8 Hz,9.8 Hz

16. H-12,ddd,8.8 Hz,6 Hz,6 Hz H-13,ddd,8.8 Hz,5.6 Hz,5.6 Hz 16-Ha,ddd,12.4 Hz,6.8 Hz,6.8 Hz H-11,br t,8.8 Hz

17. Table 2-21H-NMR spectroscopic data for RAE-1 (400 MHz, DMSO-d6) and compared with literature Abreu H A, Lago I A, Souza G P et al. Antioxidant activity of (+)-bergenin—a phy- toconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae) [J]. Organic and Biomolecular Chemistry, 2008, 6: 2713-2718.

18. 4. Chemical derivative of bergenin DFT thermodynamic calculations using .H, .OH, .CH3,and .CCl3 Frontier molecular orbital analysis

19. RAE-13 Properties: White amorphous powder, easily soluble in MeOH, insoluble in CH2Cl2. A dark spot under UV254 nm, no fluorescence under UV365 nm on silica gel TLC. Turn blue-black in 2% FeCl3-EtOH, light gray-blue in 5% PMA-EtOH, and light red in 5% H2SO4-EtOH. Purity test: GF254 silica gel TLC Polyamide TLC RAE-13, 7 mg, 1H-NMR, in CD3OD. RAE-13, 30 mg, 13C-NMR, in CD3OD.

20. RAE-13 solvent peak water peak

21. RAE-13 H-2’, H-6’, s H-10b,d,10.8Hz H-7, s H-4,dd,9 Hz,9.6 Hz

22. RAE-13 s, -OCH3 H-4a,t,10.2 Hz H-3,dd,12 Hz H-2,H-11,m,overlapped

23. RAE-13 solvent peak

24. RAE-13 3’,5’ 2’,6’ OMe 4a 2 10b 11 8 7 6a 10 3 4 9 4’ 7’ 6 1’ 10a

25. Table 113C-NMR spectroscopic data for RAE-13(600 MHz, CD3OD) and compared with literature Takashi Y, Kaoru S, Yukiko Tet al. Bergenin derivatives from Mallotus japonicus [J]. Phytochemistry, 1982, 21(5): 1180-1182.

26. Table 1(continue)13C-NMR spectroscopic data for RAE-13(600 MHz, CD3OD) and compared with literature Takashi Y, Kaoru S, Yukiko Tet al. Bergenin derivatives from Mallotus japonicus [J]. Phytochemistry, 1982, 21(5): 1180-1182.

27. 5. Isolation of bergenin

28. 5. Isolation of bergenin

32. 6. Analytical techniques Highest: Rodgersia sambucifolia Hemsl Lowest: Rodgersia aesculifolia Batalin

34. 7. Discussion Bergenia species contain most bergenin, so the most potent plant species is used in herbal formulations and has the strongest desired effect. This review gives an idea about the nature and activity of bergenin which might be used in the future for the development of new drugs for the treatment of various type of illness. Bergenia species are important medicinal plants distributed in South and East Asia and European countries. In India these plants grow at high altitudes in the Himalayas usually in rocky areas and on cliffs.

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