Chemical constituents of Swertia longifolia Boiss. with α-amylase inhibitory activity

Soodabeh Saeidnia, Leila Ara, Homa Hajimehdipoor, Roger W. Read, Sattar Arshadi, Marjan Nikan

Abstract


α-Amylase inhibitors play a critical role in the control of diabetes and many of medicinal plants have been found to act as α-amylase inhibitors. Swertia genus, belonging to the family Gentianaceae, comprises different species most of which have been used in traditional medicine of several cultures as antidiabetic, anti-pyretic, analgesic, liver and gastrointestinal tonic. Swertia longifolia Boiss. is the only species of Swertia growing in Iran. In the present investigation, phytochemical study of S. longifolia was performed and α-amylase inhibitory effects of the plant fractions and purified compounds were determined. Aerial parts of the plant were extracted with hexane, chloroform, methanol and water, respectively. The components of the hexane and chloroform fractions were isolated by different chromatographic methods and their structures were determined by 1H NMR and 13C NMR data. α-Amylase inhibitory activity was determined by a colorimetric assay using 3,5-dinitro salysilic acid. During phytochemical examination, α-amyrin, β-amyrin and β-sitosterol were purified from the hexane fraction,while ursolic acid, daucosterol and swertiamarin  were isolated from chloroform fraction. The results of the biochemical assay revealed α-amylase inhibitory activity of hexane, chloroform, methanol and water fractions, of which the chloroform and methanol fractions were more potent (IC50 16.8 and 18.1 mg/ml, respectively). Among examined compounds, daucosterol was found to be the most potent α-amylase inhibitor (57.5% in concentration 10 mg/ml). With regard to α-amylase inhibitory effects of the plant extracts, purified constituents, and antidiabetic application of the species of Swertia genus in traditional medicine of different countries, S. longifolia seems more appropriate species for further mechanistic antidiabetic evaluations.


Full Text:

PDF

References


Rahimi R, Nikfar S, Larijani B, Abdollahi M. A review on the role of antioxidants in the management of diabetes and its complications. Biomed Pharmacother. 2005;59:365-373.

DeRuiter J. Overview of the antidiabetic agents. Endocrine Pharmacotherapy Module. 2003. pp. 1-33. Available at: http://www.auburn.edu/~deruija/endo_ diabetesoralagents. pdf. Jan 2015.

Sales PM, Souza PM, Simeoni LA, Silveira D. α-Amylase inhibitors: a review of raw material and isolated compounds from plant source. J Pharm Pharm Sci. 2012;15:141-183.

Pant N, Jain DC, Bhakuni RS. Phytochemicals from genus Swertia and their biological activities. Indian J Chem. 2000;39B:565-586.

Negi JS, Singh P, Rawat B. Chemical constituents and biological importance of Swertia: A review. Curr Res Chem. 2011;3:1-15.

Bhawana K, Neetu Sh. Phytochemistry, ethnobotany and pharmacology of Swertia chirata. Int Phytomed Relat Indust. 2011;3:261-263.

Tabassum S, Mahmood S, Hanif J, Hinda M, Uzair B. An overview of medicinal importance of Swertia chirayita. Int J App Sci Technol. 2012;2:298-304.

Brahmachari G, Mondal S, Gangopadhyay A, Gorai D, Mukhopadhyay B, Saha S, et al. Swertia (Gentianaceae): chemical and pharmacological aspects. Chem Biodivers. 2004;1:1627-1651.

Jiyangsu College of New Medicine, Dictionary of Chinese Traditional Medicine. Shanghai: People’s Press; 1977. p. 2565.

Mahendran G, Thamotharan G, Sengottuvelu S, Bai VN. Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats. J Ethnopharmacol. 2014;151:1175-1183.

Mozaffarian V. A Dictionary of Iranian Pant Names. Tehran: Farhang Moaser; 2007. p. 530.

Hajimehdipour H, Amanzadeh Y, Sadat-Ebrahimi SE, Mozaffarian V. Three tetraoxygenated xanthones from Swertia longifolia. Pharm Biol. 2003;41:497-499.

Hajimehdipoor H, Dijoux-Franca MG, Mariotte AM, Amanzadeh Y, Sadat-Ebrahimi SE, Ghazi-Khansari M. Two new xanthone diglycosides from Swertia longifolia Boiss. Nat Prod Res. 2006;20:1251-1257.

Hajimehdipoor H, Dijoux-Franca MG, Mariotte AM, Amanzadeh Y, Sadat-Ebrahimi SE, Ghazi-Khansari M, et al. Phytochemical study of Swertia longifolia Boiss. DARU. 2008;16:245-249.

Hajimehdipoor H, Sadeghi Zh, Elmi S, Elmi A, Ghazi-Khansari M, Amanzadeh Y, et al. Protective effects of Swertia longifolia Boiss. and its active compound, swerchirin, on paracetamol-induced hepatotoxicity in mice. J Pharm Pharmacol. 2006;58:277-280.

Hajimehdipoor H, Esmaeili S, Shekarchi M, Emrarian T, Naghibi F. Investigation of some biologic activities of Swertia longifolia. Res Pharm Sci. 2013;8:253-259.

Giancarlo S, Rosa LM, Nadjafi F, Francesco M. Hypoglycaemic activity of two spices extracts: Rhus coriaria L. and Bunium persicum Boiss. Nat Prod Res. 2006;20:882-886.

Nickavar B, Abolhasani L, Izadpanah H. α-Amylase inhibitory activities of six Salvia species. Iran J Pharm Res. 2008;7:297-303.

Migas P, Cisowski W, Dembinska-Migas W. Isoprene derivatives from the leaves and callus cultures of Vaccinium corymbosum var. bluecrop. Acta Pol Pharm. 2005;62:45-51.

Saeidnia S, Manayi A, Gohari AR, Abdollahi M. The story of beta-sitosterol-a review. European J Med Plants. 2014;4:590-609.

Mouffok S, Haba H, Lavaud C, Long Ch, Benkhaled M. Chemical constituents of Centaurea omphalotricha Coss. & Durieu ex Batt. & Trab. Rec Nat Prod. 2012;6:292-295.

Goari AR, Saeidnia S, Shahverdi AR, Yassa N, Malmir M, Mollazade K, et al. Phytochemistry and antimicrobial compounds of Hymenocrater calycinus. Eur Asia J Bio Sci. 2009;3:64-68.

Anwar M, Ahmad M, Aslam M, Aftab Kh. Enicostema littorale: A new source of swertiamarin. Pak J Pharm Sci. 1996;9:29-35.

Chowdhury SS, Islam MN, Jung HA, Choi JS. In vitro antidiabetic potential of the fruits of Crataegus pinnatifida. Res Pharm Sci. 2014;9:11-22.

Andrade-Cetto A, Becerra-Jimenez J, Cardenas-Vazquez R. Alpha-glucosidase inhibiting activity of some Mexican plants used in the treatment of type 2 diabetes. J Ethnopharmacol. 2008;116:27-32.

Nagmoti DM, Juvekar AR. In vitro inhibitory effects of Pithecellobiumdulce (Roxb.) Benth. seeds on intestinal α-glucosidase and pancreatic α-amylase. J Biochem Tech. 2013;4:616-621.

Miller GL. Use of dinitrosalicylic acid reagent fordetermination of reducing sugar. Anal Chem. 1959;31:426-428.

Fuwa H. A new method for microdetermination of amylase activity by the use of amylose as the substrate. J Biochem. 1954;41:583-603.

Saraswathy A, Ariyanathan S. 1, 5, 8-Trihydroxy-3-methoxyxanthone from Swertia corymbosa (Griseb.) Wight ex.C.B.Clarke. Int J Pharm Life Sci. 2011;2:976-977.

Joshi P, Dhawan V. Swertia chirayita – an overview. Curr Sci. 2005;89:635-640.

Dutt B, Srivastava LJ, Singh JM. Swertia spp: a source of bitter compounds for medicinal use. Anc Sci Life. 1996;15:226-229.

Jamwal A. Systematic review on xanthones and other isolates from genus Swertia. Int J Pharm Chem Sci. 2012;1:1464-1482.

Jamaluddin F, Mohamed S, Lajis MN. Hypoglycaemic effect of Parma speciosa seeds due to the synergistic action of β-sitosterol and stigmasterol. Food Chem. 1994;49:339-345.

Radika MK, Viswanathan P, Anuradha CV. Nitric oxide mediates the insulin sensitizing effects of β-sitosterol in high fat diet-fed rats. Nitric Oxide. 2013;32:43-53.

Vivancos M, Moreno JJ. β-Sitosterol modulates antioxidant enzyme response in RAW264.7 macrophages. Free Rad Biol Med. 2005;39:91-97.

Park C, Moon DO, Rhu CH, Choi BT, Lee WH, Kim GY, et al. β-Sitosterol induces antiproliferation and apoptosis in human leukemic U937 cells through activation ofcaspase-3 and induction of Bax/Bcl-2 ratio. Biol Pharm Bull. 2007;30:1317-1323.

Manayi A, Saeidnia S, Ostad SN, Hadjiakhoondi A, Shams Ardekani MR, Vazirian M, et al. Chemical constituents and cytotoxic effect of the main compounds of Lythrum salicaria L. Z Naturforsch C. 2013;68:367-375.

Moon EJ, Lee YM, Lee OH, Lee MJ, Lee SK, Chung MH, et al. A novel angiogenic factor derived from Aloe vera gel: beta-sitosterol, a plant sterol. Angiogenesis. 1999;3:117-123.

Prieto JM, Recio MC, Giner RM. Anti-inflammatory activity of β-sitosterol in a model of oxazolone induced contact-delayed-type hypersensitivity. Bol Latinoam Caribe Plant Med Aromat. 2006;5:57-62.

Villasenor IM, Angelada J, Canlas AP, Echegoyen D. Bioactivity studies on betasitosterol and its glucoside. Phytother Res. 2002;16:417-421.

Rahman AU, Zareen S, Choudhary MI, Akhtar MN, Kah SN. Alpha-glucosidase inhibitory activity of triterpenoids from Cichorium intybus. J Nat Prod. 2008;71:910-913.

Kumar S, Kumar V, Prakash O. Enzymes inhibition and antidiabetic effect of isolated constituents from Dilleniaindica. Bio Med Res Int. 2013;2013:ID 382063.

Rathinavelusamy P, Mazumder PM, Sasmal D, Jayaprakash V. Evaluation of in silico, in vitro α-amylase inhibition potential and antidiabetic activity of Pterospermum acerifolium bark. Pharm Biol. 2014;52:199-207.

Chen B, Zhang Q, Wang W, Huang H, Kang W. Alpha-glucosidase inhibitory active constituents contained in nut shell of Trapaacornis. Zhongguo Zhong Yao Za Zhi. 2012;37:1408-1411.

Sheng Zh, Dai H, Pan S, Wang H, Hu Y, Ma W. Isolation and characterization of an α-glucosidase inhibitor from Musa spp. (Baxijiao) flowers. Molecules. 2014;19:10563-10573.


Refbacks

  • There are currently no refbacks.


Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

Creative Commons LicenseThis work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License which allows users to read, copy, distribute and make derivative works for non-commercial purposes from the material, as long as the author of the original work is cited properly.