Corresponding author (NCNPR): Fadime Aydoğan, faydogan@olemiss.eduhttps://egrove.olemiss.edu/pharm_annual_posters_2022/1000/thumbnail.jp

Ali, Zulfiqar

Aydoğan, Sophie Fadime

Karaalp, Canan

Khan, Ikhlas A.

Khan, Shabana I.

English

Bedir, Erdal

eGrove (Univ. of Mississippi)

University of Mississippi eGrove Annual Poster Session 2022 Annual Poster Session 10-11-2022 Neo-clerodanes from Teucrium divaricatum and their potential antiinflammatory and antimicrobial activities Sophie Fadime Aydoğan Dicle University; University of Mississippi, faydogan@olemiss.edu Zulfiqar Ali University of Mississippi Shabana I. Khan University of Mississippi Canan Karaalp Ege University Ikhlas A. Khan University of Mississippi Follow this and additional works at: https://egrove.olemiss.edu/pharm_annual_posters_2022 Recommended Citation Aydoğan, Sophie Fadime; Ali, Zulfiqar; Khan, Shabana I.; Karaalp, Canan; and Khan, Ikhlas A., "Neo-clerodanes from Teucrium divaricatum and their potential antiinflammatory and antimicrobial activities" (2022). Annual Poster Session 2022. 1. https://egrove.olemiss.edu/pharm_annual_posters_2022/1 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. Neo-clerodanes from Teucrium divaricatum subsp. divaricatum and their biological activity evaluation Fadime Aydoğan1,2, Zulfiqar. Ali2, Shabana I. Khan2, CananKaraalp3, Ikhlas A. Khan2, Erdal Bedir41Department of Pharmaceutical Botany, Faculty of Pharmacy, Dicle University, 21280, Sur, Turkey. 2National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA. 3Department of Pharmaceutical Botany, Faculty of Pharmacy, Ege University, 35040, Izmir, Turkey, 4 Department of Biotechnology and Bioengineering, Izmir Institute of Technology, 35430, Izmir, TurkeyAbstract: Teucrium L., one of the 245 genera in theLamiaceae family, is represented with approximately 370taxa in the world. Herein, the isolation and structuralidentification of 17 secondary metabolites including twoundescribed neo-clerodane glycosides (1-2), 13 neo-clerodane diterpenoids (3-15), an iridoid glycoside (17),and a phenylpropanoid glycoside (16) from the wholeplant of T. divaricatum subsp. divaricatum is reported.Neo-clerodane diterpenoids were evaluated for theirpotential anti-inflammatory and antimicrobial activities.Figure 1. Structures of compounds 1-17.Table 1: NMR data of compounds 1 and 2.Introduction: Teucrium L. (Lamiaceae) is representedwith approximately 370 taxa of perennial, bushy, shrubsor herbs in the world [1,2]. It’s members are mainlydistributed in the Mediterranean region with aconsiderable number of species occurring in Spain,Algeria, Morocco, Italy, Greece, and Turkey [2]. Çeçenet all described the last taxa as T. turcicum and by lastrevision of the genus, 50 Teucrium taxa (38 species) arefound in the Flora of Turkey and 19 of them areendemics in Turkey [2]. T. divaricatum and T.chamaedrys are familiar and common species known as'germander' worldwide and have traditionally been usedas tonic, carminative, spasmolytic, diuretic, antiseptic,antirheumatic, antipyretic, and anthelmintic [3-8]. Wereport the isolation and structural identification of 15neo-clerodane diterpenoids including two undescribedneo-clerodane glycosides, an iridoid glycoside and aphenylpropanoid glycoside from the whole plant of T.divaricatum subsp. divaricatum. Neo-clerodanediterpenoids were evaluated for their potential anti-inflammatory and antimicrobial activities.Figure 2:  Key COSY and HMBC correlations of compounds 1 and 2.Acknowledgments: The authors are thankful for TUBITAK 2219 Postdoctoral Fellowship. This project was supported by EgeUniversity Scientific Research Project-18-ECZ-013. References: (a) Huang, J. M.; Yang, C. S. J. Nat. Prod. 2002, 65, 527‒531. (b)Song, W. Y.; Ma, Y. B. Planta Med. 2007, 73, 372. [1] Aydoğan F., Anouar E.H., Aygün M., Yusufoglu H., Karaalp C., Bedir E. 2021, J.Mol Struct. 1231,1–12. [2] Çeçen Ö., Özcan T. 2021, Turk. J. Botany. 45, 353–370. [3] Sadeghi Z., [4]Yang J-L., Venditti A., Moridi F.M. 2022, Nat Prod Res. 0, 1–18. [5] Bahramikia S., Yazdanparast R. 2012 Phyther Res 26, 1581–1593. [6] Jaradat NA. 2015, Asian. J.Pharm. Clin. Res. 8, 13–19. [7] Donald G. 2008, Med. Tox. of Nat. Sub. 477–481.[8] Ulubelen A, Topçu G, Sönmez U. 2000, Studies inNatural Products Chemistry. 591–648.Figure 3: ECD spectra of compounds 1, 2, 8, and 9.Figure 4:  Key NOESY correlations of 1 and 2.-641424200 250 300 3506β-hydroxyteuscordin Teucrin-H2Plant Material: Plant material was collectedfrom Göynük Canyon, Antalya, Turkey, altitude574 m and identified by Fadime Aydogan(Ph.D.) and Volkan Eroğlu (Ph.D.). Voucherspecimen was deposited in the Ege UniversityHerbarium of Faculty of Pharmacy (IZEF) (#IZEF 6613).Results and Discussion: The CHCl3 and H2Ofractions of T. divaricatum subsp. divaricatumextract was subjected to column chromatogeaphyon silica gel, Sephadex LH-20, and C-18 semi-preperative HPLC to purify 17 compounds(Figure 1). Structure elucidation of the isolatedcompounds was achieved by analyses of theirNMR and mass spectral data analysis. Chemicalshifts were assigned using HSQC, COSY, andHMBC spectra (Figure 2). Relativestereochemistry at stereogenic centers wasdetermined using CD (Figure 3) and NOESYcorrelations (Figure 4). Two new neo-cleronegylcosides and 13 known neo- and nor-clerodanediterpenoids isolated from the CHCl3 fractionwere identified as teudivaricosides A (1) B (2),teucvidin (3), 2-deoxychamaedroxide (4), teuflin(5), teucrin G (6), teuflidin (7), teucrin H2 (8),6β-hydroxyteuscordin (9), teucrin F (10), 6-epiteucrin A (11), teucrin A (12), isoteuflidin (13),dihydroteugin (14), montanin E (15). Twoknown glycosides isolated from the aqueousextract were identified as leonoside A (16) and 8-O-acetyl-harpagide (17). All neo-clerodanederivatives were screened for in-vitroantimicrobial activity and antiinflammatoryactivities in terms of iNOS and NF-κBinhibition as well as for cytotoxicity. None ofthem showed significant antimicrobial activitiy(upto 20 µg/mL-lower doses) andantiinflammatory activity (upto 50 µM- lowerdoses).1a 2aδC δH (δ ppm, J= Hz) δC δH (δ ppm, J= Hz)1 23.04 1.23 (m)†1.79 (d, J=11.1)21.18 1.90 (t, J=12.4)1.25 (m)†2 25.10 1.95 (m)†1.70 (m)†27.38 2.29 (m)2.18 (p, J=12.4)†3 24.90 1.18 (m)1.51 (m)136.89 6.75 (t, J=4.7)4 44.73 3.36 (dd, J=12.3, 6.4) 149.98 -5 47.68 - 50.36 -6 75.21 3.97 (t, J=2.8) 74.69 4.36 (bs)7 31.59 2.22 (dd, J=12.5,3.9)1.97 (ddd, 18.4, 9.1, 5.2)32.03 2.30 (m)†2.05 (m)†8 33.18 2.33 (m) 34.02 2.24 (m)†9 51.53 - 50.73 -10 42.93 2.20 (m) 43.61 2.86 (dd, 13.2, 1.9)11 41.69 2.15 (d, J=8.3) 41.13 2.30-2.17 (2H, m)†12 72.05 5.43 (t, 8.7) 72.19 5.53 (t, J=8.6)13 126.23 - 125.80 -14 109.13 6.55 (d, J=1.9) 108.97 6.58 (d, J=1.9)15 145.06 7.69 (t, J=1.8) 144.93 7.70 (t, J=1.8)16 140.83 7.78 (s) 140.93 7.82 (s)17 16.97 0.95 (d, J=7.5) 16.46 0.98 (d, J=5.4)18 180.6 - 170.66 -19 71.21 4.73 (d, J=10.9)4.61 (d, J=10.9)72.65 4.79 (dd, J=8.7, 5.4)†4.18 (d, J=8.0) †20 178.0 - 178.16 -1’ 103.05 4.78 (d, J=7.7) 102.79 4.79 (dd, J=8.7, 5.4)†2’ 75.33 4.05 74.88 3.99 (dd, J=9.0, 7.7)3’ 78.61 4.23 (t, J=8.9) 78.26 4.19 (t, J=9.0) †4’ 71.95 4.14 (t, J=9.2) 71.48 4.07 (t, J=9.2)5’ 78.45 3.89 (td, J=6.0, 2.9) 78.00 3.84 (m)6’ 63.46 4.53 (dd, J=12.0, 2.0)4.32 (dd, J=12.2, 6.1)62.80 4.48 (dd, J=12.0, 2.7)4.32 (dd, J=12.0, 2.7)

Neo-clerodanes from Teucrium divaricatum and their potential antiinflammatory and antimicrobial activities

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Neo-clerodanes from Teucrium divaricatum and their potential antiinflammatory and antimicrobial activities

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