Corresponding author (NCNPR): Fadime Aydoğan, faydogan@olemiss.eduhttps://egrove.olemiss.edu/pharm_annual_posters_2022/1001/thumbnail.jp

Ali, Zulfiqar

Aydoğan, Sophie Fadime

Bedir, Erdal

Khan, Ikhlas A.

Khan, Shabana I.

Zhao, Jianping

English

eGrove (Univ. of Mississippi)

University of Mississippi eGrove Annual Poster Session 2022 Annual Poster Session 10-11-2022 Biological and Phytochemical Studies on Six Astragalus Taxa from Anatolia Sophie Fadime Aydoğan Dicle University; University of Mississippi, faydogan@olemiss.edu Zulfiqar Ali University of Mississippi Shabana I. Khan University of Mississippi Jianping Zhao University of Mississippi Ikhlas A. Khan University of Mississippi See next page for additional authors Follow this and additional works at: https://egrove.olemiss.edu/pharm_annual_posters_2022 Recommended Citation Aydoğan, Sophie Fadime; Ali, Zulfiqar; Khan, Shabana I.; Zhao, Jianping; Khan, Ikhlas A.; and Bedir, Erdal, "Biological and Phytochemical Studies on Six Astragalus Taxa from Anatolia" (2022). Annual Poster Session 2022. 2. https://egrove.olemiss.edu/pharm_annual_posters_2022/2 This Book is brought to you for free and open access by the Annual Poster Session at eGrove. It has been accepted for inclusion in Annual Poster Session 2022 by an authorized administrator of eGrove. For more information, please contact egrove@olemiss.edu. Authors Sophie Fadime Aydoğan, Zulfiqar Ali, Shabana I. Khan, Jianping Zhao, Ikhlas A. Khan, and Erdal Bedir This book is available at eGrove: https://egrove.olemiss.edu/pharm_annual_posters_2022/2 Biological and Phytochemical Studies on Astragalus Taxa from Anatolia Fadime Aydoğan1,2, Zulfiqar. Ali2, Shabana I. Khan2, Jianping Zhao2,  Ikhlas A. Khan21 Department of Pharmaceutical Botany, Faculty of Pharmacy, Dicle University, 21280, Sur, Turkey2National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, 38677, Oxford, MS, Abstract: Astragalus L. (Fabaceae), one of the largest genera inAngiosperm, is represented with approximately 2500-3000 taxa. With theaim to study Astragalus taxa in Anatolia, Turkey, that is reported 425-450taxa (endemism ratio 47-50%), we report anti-inflammatory effect ofethanolic extracts of roots from six Astragalus spp. and phytochemicalinvestigation of Astragalus strictispinus Boiss. Phytochemical analysis ofAstragalus strictispinus roots resulted in isolation and structuralidentification of 25 cycloartane type triterpenoids (1-25) including nineundescribed cyloartanes, eleven flavonoids and lignans (26-33), onepterocarbon and one pterocarbon glycoside (34-35), a steroidal glycoside(36).Figure 1. Collected Astragalus spp. from Kumalar MountainIntroduction: Astragalus L. (Fabaceae) is represented with approximately 3000 taxa of annual or perennialstemmed herbs or small shrubs (up to 150–200 cm), leguminose flowers, a legume pod with kidney-shaped seedsin the world [1-3]. It’s members are mainly distributed temperate region in Europe, Asia, and North America [2].Guner et all described 452 taxa in Astragalus genus in Flora of Turkey and 224 of them are endemics in Turkey[2]. Astragalus root has been used for more than two millenniums in folk medicine to prevent and treat differentillnesses as hepatoprotective, antioxidative, immunostimulant, antiviral, antidiabetic, cardioprotective, anti-inflammatory, wounds, leukemia, and anticancer. [3-8]. Many studies reported anticancer, anti-inflammatory,antiaging, immunomodulatory, antiviral, activity of Astragalus extract and main phytochemicals. The majorphytochemicals of Astragalus taxa displaying beneficial properties include saponins, flavonoids, andpolysaccharides [3-10]. Astragalosides are the main cyloartane-type saponins, with astragaloside IV as the qualitycontrol biomarker. Astragalosides IV and VII and cycloastragenol possess antioxidative, antiaging, anti-inflammatory, antiasthma, antidiabetes, and antiatherosclerosis activities, as well as cardioprotective andneuroprotective effects [9-15]. Herein, we report in-vitro anti-inflammatory activities of ethanolic extract of sixAstragalus taxa and detailed investigation of phytoconstituents from roots of Astragalus strictispinus Boiss.Figure 2. Anti-inflammatory activity of ethanolic extracts from Astragalus spp.Acknowledgments: The authors are thankful for TUBITAK 2219 Postdoctoral Fellowship. References:[1] Auyeung, K. K.; Han, Q. bin; Ko, J. K.Am J Chin Med (Gard City NY) 2016, 44 (1), 1–22. [2] G, A.Türkiye Bitkileri Listesi (Damarlı Bitkiler) (1st Ed.); Nezahat Gökyiğit Botanik Bahçesi ve FloraAraştırmaları Derneği, 2012. [3]Z, G.; Uba, A. I.; Ocal, M.; Sharifi-Rad, M.; Caprioli, G.; Angeloni, S.;Altunoglu, Y. C.; Baloglu, M. C.; Yıldıztugay, E. Food Bioscience 2022, 49, 101858. [4] Salehi, B.;Carneiro, J. N. P.; Rocha, J. E.; Coutinho, H. D. M.; Morais Braga, M. F. B.; Sharifi-Rad, J.; Semwal, P.;Painuli, S.; Moujir, L. M.; de Zarate Machado, V.; Janakiram, S.; Anil Kumar, N. V.; Martorell, M.; Cruz-Martins, N.; el Beyrouthy, M.; Sadaka, C. Phytotherapy Research 2021, 35 [5]Çalis, I.; Gazar, H. A.;Piacente, S.; Pizza, C. Journal of Natural Products 2001, 64 (9), 1179–1182. [6] Zheng, Y.; Ren, W.; Zhang,L.; Zhang, Y.; Liu, D.; Liu, Y.. Frontiers in Pharmacology 2020, 11 (3), 1–15. [7] Li, X.; Qu, L.; Dong, Y.;Han, L.; Liu, E.; Fang, S.; Zhang, Y.; Wang, T. Molecules 2014, 19 (11), 18850–18880. [8] Ionkova, I.;Shkondrov, A.; Krasteva, I.; Ionkov, T. Phytochemistry Reviews 2014, 13 (2). [9] Korany, M. A.; Moneeb,M. S.; Asaad, A. M.; El‐Sebakhy, N. A.; El‐Banna, A. A. 2020. [10] Nartop, P.; Gürel, A.; Akgün, I. H.;Bedir, E.Indian Journal of Biotechnology 2015, 14 (4), 540–546. [11] Fu, J.; Wang, Z.; Huang, L.; Zheng,S.; Wang, D.; Chen, S.; Zhang, H.; Yang, S.. Phytotherapy Research 2014, 28 (9), 1275–1283. [12] Yu, Y.;Zhou, L.; Yang, Y.; Liu, Y.. Experimental and Therapeutic Medicine. Spandidos Publications September 1,[13] He, M.; Wang, K.; Che, H.; Wang, H.; Yang, K.; Zhang, G.; Yao, J.; Wang, J.. European Journal ofMedicinal Chemistry Reports 2022, 5, 100060. [14] Yilmaz, S.; Bedir, E.; Ballar Kirmizibayrak, P. FreeRadic Biol Med 2022, 188, 105–116. [15] Tan, Y. Q.; Chen, H. W.; Li, J. Drug Design, Development andTherapy 2020, 14, 3731–3746.Figure 3. Structure of isolated undescribed triterpene derivatives from A. strictispinusResults and Discussion: Air-dried-grounded roots of 10 Astragalus samples (10 g each) were extracted withethanol by Dionex™ ASE™ 350 accelerated solvent extractor. Filtered extracts were dried under the vacuumand freeze dried. Extracts were screened for antiinflammatory activities in terms of iNOS inhibition and NRF-2 activation as well as for cytotoxicity. Only A. strictispinus extract inhibited iNOS with IC50 values of 87µg/mL. The roots of Astragalus strictispinus (1.1 kg) was extracted with MeOH (5L x 24 h x 3) at roomtemperature. The dried MeOH extract (137 g) was subjected to column chromatography on silica gel,Sephadex LH-20, and C18 semi-preperative HPLC to purify 36 compounds. Structure elucidation of theisolated compounds was achieved by analyses of their NMR and mass spectral data. Chemical shifts wereassigned using HSQC, COSY, and HMBC, NOESY spectra (Figure 3). Seven new triterpenes (1-7) (Figures 3and 4), astrastricspins A-G and two new triterpene glycosides (8 and 9): astrastricspinosides I and II together16 known saponins, isolated from the root extract, were identified as cycloastragenol (10), cycloasalgenin(11), 20(R),25-epoxy-3β‚6α,16β,24α-tetrahydroxycycloartane (12), cyclopycnanthogenin (13), 17-epi-cycloasalgenin (14), cycloadsurgenin (15), cycloasgenin C (16), cycloastragenol-6-O-β-D-glucopyranoside(17), cycloastragenol-16-O-β-D-glucopyranoside (18), cycloasgenin-6-O-β-D-glucopyranoside(19),astragaloside IV (20), astragaloside II (21), astragaloside VII (22), astrasieversianin X (23), cyclosieversiosideI (24), astragaloside VI (25), with other phytochemical class known compounds as vestitol (26), sissotrin (27),ononin (28), acacetin (29), artocarpetin (30), isoliquiritigen (31), lariciresinol (32), 3′,4′,7-trihydroxyflavone(33), and maackianin (34), maackianin-3-O β-D-glucopyranoside (35) and sitosterol-3-O-β-D-glucopyranoside(36).Binominal Name NCNPR Cytotoxıcıty iNOS inh NRF2 activation.A. strictispinus 24183 NC NA NAA. angustifolius subsp. pungens 24184 NC NA NAA. creticus 24185 NC NA NAA. creticus 24186 NC NA NAA. flavecens 24187 NC NA NAA. angustifolius subsp. angustifolius 24188 NC NA NAA. ponticus 24189 NC NA NAA. strictispinus 24190 NC NA NAA. strictispinus 24191 NC 87 µg/mL NAA.creticus 24192 NC NA NA24188 24185 2418924184 2418724183 24191 24188Plant Material: Plant materials were collected from Kumalar Mountain,Afyonkarahisar, Turkey, altitude 1500-2000 m and identified by FadimeAydogan (Ph.D.) and Volkan Eroğlu (Ph.D.). Voucher specimens weredeposited in the Ege University Herbarium of Faculty of Pharmacy (IZEF)and all samples were saved at NCNPR, University of Mississippi.Highest tested concentration for extract = 100 µg/mL, Parthenolide for iNOS, Curcumin for NRF2 were used for standard drugOOOHHOOOHOHOHOOOOHOOOOOHOHOHOOHOOHHOOHOOHOHHOOOOHH1 2 34 5 6HHHOH2030405060708090100110120130140150160170180190200210220f1 (ppm)050100150200250300350400450500550FA-2-5-4AS_CARBON_0118.5119.9121.9722.0123.1426.7726.9529.5629.9932.5539.6340.4941.8744.8446.0048.4251.2855.03127.73135.91 Pyridine-d5150.75202.98208.66217.040.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)0102030405060708090100110120130140150160170180190200210220f1 (ppm)FA-2-5-4AS_gHMBCAD_010.51.01.52.02.53.03.54.04.55.05.56.06.57.0f2 (ppm)0.51.01.52.02.53.03.54.04.55.05.56.06.57.0f1 (ppm)FA-2-5-4AS_gCOSY_010.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f2 (ppm)102030405060708090100110120130140150160f1 (ppm)FA-2-5-4AS_HSQCAD_010.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)-100001000200030004000500060007000800090001000011000120001300014000150000.990.536.910.872.854.671.220.821.902.710.901.150.651.270.941.011.000.660.670.680.680.951.061.071.111.121.131.251.261.271.311.341.351.521.531.531.541.551.561.561.571.581.591.611.621.701.711.731.741.771.781.951.992.042.052.072.082.082.092.112.192.202.212.212.242.242.252.302.452.472.492.502.522.632.642.652.842.852.872.872.893.293.296.226.236.246.256.276.286.826.836.846.857.58 Pyridine-d50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f2 (ppm)012345678f1 (ppm)FA-1-34-2AS_NOESY_01Figure 4. 1D  and 2D NMR spectra of Compound 7OOO7234567891112131415161718282930191HNOESYHMBCCOSY

Biological and Phytochemical Studies on Six Astragalus Taxa from Anatolia

https://egrove.olemiss.edu/cgi/viewcontent.cgi?article=1001&context=pharm_annual_posters_2022

Biological and Phytochemical Studies on Six Astragalus Taxa from Anatolia

Abstract

Similar works

Full text

Available Versions

eGrove (Univ. of Mississippi)