Generic placeholder image

Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Review Article

Secoiridoid Amarogentin from ‘Gentianaceae’ with their Health Promotion, Disease Prevention and Modern Analytical Aspects

Author(s): Kanika Patel and Dinesh K. Patel*

Volume 16, Issue 3, 2020

Page: [191 - 200] Pages: 10

DOI: 10.2174/1573407214666181023115355

Price: $65

Abstract

Background: Plant-based products and their derivatives have been widely used in the medicine, nutraceuticals, and the cosmetic and pharmaceutical field for a very long time. A large number of important drugs of modern medicine have also been derived from the plant's sources. Plant products specifically the pure phytochemical also known as ‘biomarkers’ have been used in the food and pharmaceutical industries. Biomarker compounds are pure phytochemical and they are mainly responsible for various pharmacological activities of plant material and examples of biomarker are Amarogentin, Vasicine, Hyoscyamine and Paclitaxel.

Methods: Various literature databases were searched to collect important information about Amarogentin in this review. Ethnomedicinal uses, pharmacological activities, phytochemical aspects and modern analytical tools of amarogentin were presented and discussed. Further, all the collected information’s were categorized into different section as per the need of the manuscripts. Moreover, data were also presented in the graphical abstract, Figures and Table section too.

Results: Swertia chirata (S. chirata) is a common plant of Gentianaecae family which is mainly known for their bitter taste. Gentiopicroside, amarogentin, swertiamarin, isovitexin and isogentisin are some important phytoconstituents of S. chirata. Decoction, infusion, pastes and juice of S. chirata are basically used in the medicine. Various Pharmacological activities such as hypoglycemic, antimicrobial, antimalarial, antihepatotoxic, anticarcinogenic, antioxidative and anti-inflammatory have been reported in the literature for S. chirata plant. Amarogentin, a bitter secoiridoid glycoside of S. chirata has been well known for antibacterial, anticholinergic anti-lieshmanial, chemopreventive, antihepatitis and anticancer activities.

Conclusion: Information provided in the present paper regarding phytochemistry, pharmacological uses and analytical aspects including bioavailability will be beneficial to various disciplines of biological science. Development of plant tissue culture-based approaches is also needed for the proper conservation of S. chirayita plants in the future.

Keywords: Amarogentin, analytical aspects, medicinal uses, pharmacological activities, S. chirayita, biomarkers.

Graphical Abstract
[1]
Patel, K.; Kumar, V.; Verma, A.; Rahman, M.; Patel, D.K. Health benefits of furanocoumarins ‘Psoralidin’ an active phytochemical of Psoralea Corylifolia: The present, past and future scenario. Curr. Bioact. Compd., 2018, 5(4), 369-376.
[2]
Patel, D.K.; Patel, K.; Duraiswamy, B.; Dhanabal, S.P. Phytochemical analysis and standardization of strychnos nux-vomica extract through HPTLC techniques. Asian Pac. J. Trop. Dis., 2012, 2(Suppl. 1), S56-S60.
[http://dx.doi.org/10.1016/S2222-1808(12)60124-8]
[3]
Patel, D.K.; Patel, K.; Dhanabal, S.P. Development of quality control parameters for the standardization of Gymnema Sylvestre. J. Acute Dis., 2012, 1(2), 141-143.
[http://dx.doi.org/10.1016/S2221-6189(13)60032-3]
[4]
Patel, K.; Patel, D.K. Medicinal importance, pharmacological activities, and analytical aspects of hispidulin: A concise report. J. Tradit. Complement. Med., 2016, 7(3), 360-366.
[http://dx.doi.org/10.1016/j.jtcme.2016.11.003] [PMID: 28725632]
[5]
Harris, R. Trease and Evans’. Pharmacognosy. Int. J. Aromather., 2003, 13(1), 55.
[http://dx.doi.org/10.1016/S0962-4562(03)00051-1]
[6]
Chothani, D.L.; Patel, M.B.; Mishra, S.H. HPTLC fingerprint profile and isolation of marker compound of Ruellia Tuberosa. Chromatogr. Res. Int., 2012, 2012, 1-6.
[http://dx.doi.org/10.1155/2012/180103]
[7]
Gao, J.; Sanchez-Medina, A.; Pendry, B.A.; Hughes, M.J.; Webb, G.P.; Corcoran, O. Validation of a HPLC method for flavonoid biomarkers in skullcap (Scutellaria) and its use to illustrate wide variability in the quality of commercial tinctures. J. Pharm. Pharm. Sci., 2008, 11(1), 77-87.
[http://dx.doi.org/10.18433/J39G6V] [PMID: 18445366]
[8]
Nandanwadkar, S.M.; Mastiholimath, V.S.; Surlaker, S.R. HPTLC method development and validation of antidiabetic marker compound from polyherbal formulation. Indian J. Pharm. Educ. Res., 2016, 50(4), 657-664.
[http://dx.doi.org/10.5530/ijper.50.4.18]
[9]
Khanal, S.; Shakya, N.; Thapa, K.; Pant, D.R. Phytochemical investigation of crude methanol extracts of different species of Swertia from Nepal. BMC Res. Notes, 2015, 8(1), 821.
[http://dx.doi.org/10.1186/s13104-015-1753-0] [PMID: 26708007]
[10]
Shubham; Bhardwaj, U.; Mathur, A. Isolation and identification of amarogentin as an antihelminthic compound in Swertia Chirayta. J. Chem. Pharm. Res., 2016, 8(4), 1374-1381.
[11]
Kavitha, K.; Dattatri, A. An evaluation of antidiabetic potential of methanolic extract of Swertia Chirata in streptozotocin induced diabetic rats. Res. J. Pharm. Biol. Chem. Sci., 2015, 6(1), 620-625.
[12]
Shukla, S.; Bafna, K.; Sundar, D.; Thorat, S.S. The bitter barricading of prostaglandin biosynthesis pathway: understanding the molecular mechanism of selective cyclooxygenase-2 inhibition by amarogentin, a secoiridoid glycoside from Swertia chirayita. PLoS One, 2014, 9(6)e90637
[http://dx.doi.org/10.1371/journal.pone.0090637] [PMID: 24603686]
[13]
Chakraborty, S.; Mukherjee, D.; Baskey, S. Morphological diversity and nomenclature of Swertia Chirayita (Gentianaceae)—Recovery of endangered medicinal plant population in North Eastern Himalaya. Am. J. Plant Sci., 2016, 7, 741-755.
[http://dx.doi.org/10.4236/ajps.2016.76068]
[14]
Kumar, V.; Van Staden, J. A Review of Swertia chirayita (Gentianaceae) as a traditional medicinal plant. Front. Pharmacol., 2016, 6, 308.
[http://dx.doi.org/10.3389/fphar.2015.00308] [PMID: 26793105]
[15]
Shailja. A Mini Review on in vitro Propagation of Swertia Chirayita an endangered medicinal plant. Biosci. Biotechnol. Res. Commun., 2017, 10(1), 6-10.
[http://dx.doi.org/10.21786/bbrc/10.1/2]
[16]
Das, S.C.; Bhadra, S.; Roy, S.; Saha, S.K.; Islam, M.S.; Bachar, S.C. Analgesic and anti-inflammatory activities of ethanolic root extract of Swertia Chirata (Gentianaceae). Jordan J. Biol. Sci., 2012, 5(1), 31-36.
[17]
Kumar, V.; Chandra, S. LC-ESI/MS determination of xanthone and secoiridoid glycosides from in vitro regenerated and in vivo Swertia chirayita. Physiol. Mol. Biol. Plants, 2015, 21(1), 51-60.
[http://dx.doi.org/10.1007/s12298-014-0276-9] [PMID: 25649848]
[18]
Wang, C.Z.; Maier, U.H.; Zenk, M.H. Synthesis of 3,3′,5-trihydroxybiphenyl-2-carboxylic acid, a component of the bitterest natural product amarogentin and its coenzyme A and N-acetyl cysteamine thiol esters. J. Nat. Prod., 2000, 63(3), 371-374.
[http://dx.doi.org/10.1021/np990256m] [PMID: 10757721]
[19]
Niu, H.S.; Chao, P.C.; Ku, P.M.; Niu, C.S.; Lee, K.S.; Cheng, J.T. Amarogentin ameliorates diabetic disorders in animal models. Naunyn Schmiedebergs Arch. Pharmacol., 2016, 389(11), 1215-1223.
[http://dx.doi.org/10.1007/s00210-016-1283-x] [PMID: 27485449]
[20]
Yen, T.L.; Lu, W.J.; Lien, L.M.; Thomas, P.A.; Lee, T.Y.; Chiu, H.C.; Sheu, J.R.; Lin, K.H. Amarogentin, a secoiridoid glycoside, abrogates platelet activation through PLC γ 2-PKC and MAPK pathways. BioMed Res. Int., 2014, 2014 Article ID 728019
[21]
Phoboo, S.; Pinto, Mda.S.; Barbosa, A.C.; Sarkar, D.; Bhowmik, P.C.; Jha, P.K.; Shetty, K. Phenolic-linked biochemical rationale for the anti-diabetic properties of Swertia chirayita (Roxb. ex Flem.) Karst. Phytother. Res., 2013, 27(2), 227-235.
[http://dx.doi.org/10.1002/ptr.4714] [PMID: 22523004]
[22]
Akileshwari, C.; Muthenna, P.; Nastasijevi, B.; Joksi, G.; Petrash, J. M.; Reddy, G. B. Inhibition of aldose reductase by Gentiana Lutea extracts.Exp. Diabetes Res. 2012, 2012.
[23]
Nastasijević, B.; Lazarević-Pašti, T.; Dimitrijević-Branković, S.; Pašti, I.; Vujačić, A.; Joksić, G.; Vasić, V. Inhibition of myeloperoxidase and antioxidative activity of Gentiana lutea extracts. J. Pharm. Biomed. Anal., 2012, 66, 191-196.
[http://dx.doi.org/10.1016/j.jpba.2012.03.052] [PMID: 22521634]
[24]
Roudnitzky, N.; Behrens, M.; Engel, A.; Kohl, S.; Thalmann, S.; Hübner, S.; Lossow, K.; Wooding, S.P.; Meyerhof, W. Receptor polymorphism and genomic structure interact to shape bitter taste perception. PLoS Genet., 2015, 11(9)e1005530
[http://dx.doi.org/10.1371/journal.pgen.1005530] [PMID: 26406243]
[25]
Behrens, M.; Brockhoff, A.; Batram, C.; Kuhn, C.; Appendino, G.; Meyerhof, W. The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin. J. Agric. Food Chem., 2009, 57(21), 9860-9866.
[http://dx.doi.org/10.1021/jf9014334] [PMID: 19817411]
[26]
Wölfle, U.; Elsholz, F.A.; Kersten, A.; Haarhaus, B.; Müller, W.E.; Schempp, C.M. Expression and functional activity of the bitter taste receptors TAS2R1 and TAS2R38 in human keratinocytes. Skin Pharmacol. Physiol., 2015, 28(3), 137-146.
[http://dx.doi.org/10.1159/000367631] [PMID: 25573083]
[27]
Ley, J.P.; Krammer, G.; Reinders, G.; Gatfield, I.L.; Bertram, H.J. Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae). J. Agric. Food Chem., 2005, 53(15), 6061-6066.
[http://dx.doi.org/10.1021/jf0505170] [PMID: 16028996]
[28]
Zhao, J.G.; Zhang, L.; Xiang, X.J.; Yu, F.; Ye, W.L.; Wu, D.P.; Wang, J.F.; Xiong, J.P. Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. J. BUON, 2016, 21(3), 609-617.
[PMID: 27569081]
[29]
Huang, C.; Li, R.; Zhang, Y.; Gong, J. Amarogentin Induces apoptosis of liver cancer Cells via upregulation of p53 and downregulation of human telomerase reverse transcriptase in Mice. Technol. Cancer Res. Treat., 2017, 16(5), 546-558.
[http://dx.doi.org/10.1177/1533034616657976] [PMID: 27402632]
[30]
Sur, S.; Pal, D.; Banerjee, K.; Mandal, S.; Das, A.; Roy, A.; Panda, C.K. Amarogentin regulates self renewal pathways to restrict liver carcinogenesis in experimental mouse model. Mol. Carcinog., 2016, 55(7), 1138-1149.
[http://dx.doi.org/10.1002/mc.22356] [PMID: 26154024]
[31]
Saha, P.; Mandal, S.; Das, A.; Das, S. Amarogentin can reduce hyperproliferation by downregulation of Cox-II and upregulation of apoptosis in mouse skin carcinogenesis model. Cancer Lett., 2006, 244(2), 252-259.
[http://dx.doi.org/10.1016/j.canlet.2005.12.036] [PMID: 16517061]
[32]
Saha, P.; Das, S. Highlighting the anti-carcinogenic potential of an ayurvedic medicinal plant, Swertia Chirata. Asian Pac. J. Cancer Prev., 2010, 11(6), 1445-1449.
[PMID: 21338178]
[33]
Saha, P.; Mandal, S.; Das, A.; Das, P.C.; Das, S. Evaluation of the anticarcinogenic activity of Swertia chirata Buch.Ham, an Indian medicinal plant, on DMBA-induced mouse skin carcinogenesis model. Phytother. Res., 2004, 18(5), 373-378.
[http://dx.doi.org/10.1002/ptr.1436] [PMID: 15173996]
[34]
Wölfle, U.; Haarhaus, B.; Schempp, C.M. Amarogentin displays immunomodulatory effects in human mast cells and keratinocytes. Mediators Inflamm., 2015, 2015
[http://dx.doi.org/10.1155/2015/630128]
[35]
Medda, S.; Mukhopadhyay, S.; Basu, M.K. Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms. J. Antimicrob. Chemother., 1999, 44(6), 791-794.
[http://dx.doi.org/10.1093/jac/44.6.791] [PMID: 10590280]
[36]
Ray, S.; Majumder, H.K.; Chakravarty, A.K.; Mukhopadhyay, S.; Gil, R.R.; Cordell, G.A. Amarogentin, a naturally occurring secoiridoid glycoside and a newly recognized inhibitor of topoisomerase I from Leishmania donovani. J. Nat. Prod., 1996, 59(1), 27-29.
[http://dx.doi.org/10.1021/np960018g] [PMID: 8984149]
[37]
Suryawanshi, S.; Asthana, R.K.; Gupta, R.C. Assessment of systemic interaction between Swertia chirata extract and its Bioactive constituents in rabbits. Phytother. Res., 2009, 23(7), 1036-1038.
[http://dx.doi.org/10.1002/ptr.2738] [PMID: 19140153]
[38]
Koul, S.; Suri, K.A.; Dutt, P.; Sambyal, M.; Ahuja, A.; Kaul, M.K. Protocol for in vitro regeneration and marker glycoside assessment in Swertia chirata Buch-Ham. Methods Mol. Biol., 2009, 547, 139-153.
[http://dx.doi.org/10.1007/978-1-60327-287-2_12] [PMID: 19521842]
[39]
Keil, M.; Härtle, B.; Guillaume, A.; Psiorz, M. Production of amarogentin in root cultures of Swertia chirata. Planta Med., 2000, 66(5), 452-457.
[http://dx.doi.org/10.1055/s-2000-8579] [PMID: 10909267]
[40]
Lad, H.; Bhatnagar, D. Amelioration of oxidative and inflammatory changes by Swertia chirayita leaves in experimental arthritis. Inflammopharmacology, 2016, 24(6), 363-375.
[http://dx.doi.org/10.1007/s10787-016-0290-3] [PMID: 27738917]
[41]
He, K.; Cao, T-W.; Wang, H-L.; Geng, C-A.; Zhang, X-M.; Chen, J-J. [Chemical constituents of Swertia patens]. Zhongguo Zhongyao Zazhi, 2015, 40(20), 4012-4017.
[PMID: 27062819]
[42]
Pan, Y.; Zhang, J.; Zhao, Y-L.; Wang, Y-Z.; Jin, H. Chemotaxonomic studies of nine Gentianaceae species from western china based on liquid chromatography tandem mass spectrometry and fourier transform infrared spectroscopy. Phytochem. Anal., 2016, 27(3-4), 158-167.
[http://dx.doi.org/10.1002/pca.2611] [PMID: 26919544]
[43]
Amakura, Y.; Yoshimura, M.; Morimoto, S.; Yoshida, T.; Tada, A.; Ito, Y.; Yamazaki, T.; Sugimoto, N.; Akiyama, H. Chromatographic evaluation and characterization of components of gentian root extract used as food additives. Chem. Pharm. Bull. (Tokyo), 2016, 64(1), 78-82.
[http://dx.doi.org/10.1248/cpb.c15-00776] [PMID: 26726749]
[44]
Mustafa, A.M.; Caprioli, G.; Ricciutelli, M.; Maggi, F.; Marín, R.; Vittori, S.; Sagratini, G. Comparative HPLC/ESI-MS and HPLC/DAD study of different populations of cultivated, wild and commercial Gentiana lutea L. Food Chem., 2015, 174, 426-433.
[http://dx.doi.org/10.1016/j.foodchem.2014.11.089] [PMID: 25529701]
[45]
Mahendran, G.; Thamotharan, G.; Sengottuvelu, S.; Narmatha Bai, V. RETRACTED: Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats. J. Ethnopharmacol., 2014, 151(3), 1175-1183.
[http://dx.doi.org/10.1016/j.jep.2013.12.032] [PMID: 24378350]
[46]
Singh, P.P.; Ambika, ; Chauhan, S.M. Activity-guided isolation of antioxidant xanthones from Swertia chirayita (Roxb.) H. Karsten (Gentianaceae). Nat. Prod. Res., 2012, 26(18), 1682-1686.
[http://dx.doi.org/10.1080/14786419.2011.592836] [PMID: 21985644]
[47]
Citová, I.; Ganzera, M.; Stuppner, H.; Solich, P. Determination of gentisin, isogentisin, and amarogentin in Gentiana lutea L. by capillary electrophoresis. J. Sep. Sci., 2008, 31(1), 195-200.
[http://dx.doi.org/10.1002/jssc.200700325] [PMID: 18064621]
[48]
Suryawanshi, S.; Asthana, R.K.; Gupta, R.C. Simultaneous estimation of mangiferin and four secoiridoid glycosides in rat plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study of herbal preparation. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2007, 858(1-2), 211-219.
[http://dx.doi.org/10.1016/j.jchromb.2007.08.034] [PMID: 17869193]
[49]
Aberham, A.; Schwaiger, S.; Stuppner, H.; Ganzera, M. Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS. J. Pharm. Biomed. Anal., 2007, 45(3), 437-442.
[http://dx.doi.org/10.1016/j.jpba.2007.07.001] [PMID: 17697760]
[50]
Suryawanshi, S.; Mehrotra, N.; Asthana, R.K.; Gupta, R.C. Liquid chromatography/tandem mass spectrometric study and analysis of xanthone and secoiridoid glycoside composition of Swertia chirata, a potent antidiabetic. Rapid Commun. Mass Spectrom., 2006, 20(24), 3761-3768.
[http://dx.doi.org/10.1002/rcm.2795] [PMID: 17120271]
[51]
Kalamkar, V.; Mahurkar, N.; Gupta, R.C. A Sensitive and Selective LC-MS-MS Method for Simultaneous Determination of Picroside-I and Kutkoside (Active Principles of Herbal Preparation Picroliv) Using Solid Phase Extraction in Rabbit Plasma: Application to Pharmacokinetic Study J. Chromatogr. B. Anal., 2005, 820(2), 221-227.
[http://dx.doi.org/10.1016/j.jchromb.2005.03.032]
[52]
Lacaille-Dubois, M.A.; Galle, K.; Wagner, H. Secoiridoids and xanthones from Gentianella nitida. Planta Med., 1996, 62(4), 365-368.
[http://dx.doi.org/10.1055/s-2006-957908] [PMID: 17252473]
[53]
Kikuzaki, H.; Kawasaki, Y.; Kitamura, S.; Nakatani, N. Secoiridoid glucosides from Swertia mileensis. Planta Med., 1996, 62(1), 35-38.
[http://dx.doi.org/10.1055/s-2006-957792] [PMID: 8720386]
[54]
Zhang, J.S.; Tian, Z.X.; Lou, Z.C. [Simultaneous determination of five bitter secoiridoid glycosides in nine Chinese Gentiana species used as the Chinese drug “long dan” by high performance liquid chromatography]. Yao Xue Xue Bao, 1991, 26(11), 864-870.
[PMID: 1823982]
[55]
Schaufelberger, D.; Domon, B.; Hostettmann, K. Desorption/Chemical ionization mass spectrometry of bitter glycosides from gentiana1. Planta Med., 1984, 50(5), 398-403.
[http://dx.doi.org/10.1055/s-2007-969748] [PMID: 17340340]
[56]
Bricout, J.; Koziet, Y.; de Carpentrie, B. [High-performance liquid-liquid chromatography in beverage analysis]. Ann. Nutr. Aliment., 1978, 32(5), 947-955.
[PMID: 754597]
[57]
Eskandani, M.; Babak Bahadori, M.; Zengin, G.; Dinparast, L.; Bahadori, S. Novel natural agents from Lamiaceae Family: An evaluation on toxicity and enzyme inhibitory potential linked to diabetes mellitus. Curr. Bioact. Compd., 2016, 12(1), 34-38.
[http://dx.doi.org/10.2174/1573407212666151231183118]
[58]
Patel, K.; Kumar, V.; Verma, A.; Rahman, M.; Patel, D.K. β-sitosterol: Bioactive compounds in foods, their role in health promotion and disease prevention “a concise report of its phytopharmaceutical importance”. Curr. Tradit. Med., 2017, 3(3), 168-177.
[http://dx.doi.org/10.2174/2215083803666170615111759]
[59]
Ismail, A.; Lamia, H.; Mohsen, H.; Bassem, J. herbicidal potential of essential oils from three mediterranean trees on different weeds. Curr. Bioact. Compd., 2012, 8, 3-12.
[http://dx.doi.org/10.2174/157340712799828197]
[60]
Habbab, A.; Sekkoum, K.; Belboukhari, N.; Cheriti, A.; Aboul-Enein, H.Y. essential oil chemical composition of vitex Agnus-Castus L. from Southern-West Algeria and its antimicrobial activity. Curr. Bioact. Compd., 2016, 12(1), 51-60.
[http://dx.doi.org/10.2174/1573407212666160330152633]
[61]
Fatah, K.; Belboukhari, N.; Djaradi, H.; Cheriti, A.; Sekkoum, K.; Aboul-Eneinc, H.Y. total antioxidant capacity, reducing power and cyclic voltammetry of Zilla Macroptera (Brassicaceae) aqueous extract. Curr. Bioact. Compd., 2016, 12, 39-43.
[http://dx.doi.org/10.2174/1573407212666160210230707]
[62]
Kumar, V.; Kaithwas, G.; Anwar, F.; Rahman, M.; Patel, D.K.; Singh, Y.; Verma, A. Effect of variable doses of Paederia Foetida L. combat against experimentally- induced systemic and topical inflammation in wistar rats. Curr. Bioact. Compd., 2018, 14(1), 70-79.
[http://dx.doi.org/10.2174/1573407213666161214122912]
[63]
Zhao-yun, L.I.; Zhi-yuan, W.A.N.G. XIAO Huai2, L. L. Chemical constituents of Swertia Nervosa. Nat. Prod. Res. Dev., 2016, 28(2), 232-235.
[64]
Tabassum, S.; Mahmood, S.; Hanif, J.; Hina, M.U.B. An Overview of medicinal importance of Swertia Chirayita. Int. J. Appl. Sci. Technol., 2012, 2(1), 298-304.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy