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Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities

Yıl 2023, Cilt: 27 Sayı: 3, 1202 - 1212, 28.06.2025

Rima Konya Konuk , Rengin Reis , Hande Sipahi , Anita Barta Judit Hohmann Hasan Kırmızıbekmez

Öz

Using various chromatographic methods, seven compounds, including two secoiridoid glycosides;
depressine (1) and gentiopicroside (2), one iridoid glycoside; loganic acid (3), two flavone-C-glycosides; isoorientin (4)
and isovitexin (5), one xanthone-C-glycoside, mangiferin (6) as well as a nucleoside; adenosine (7) were isolated from
the MeOH extract prepared from the aerial parts of Gentiana asclepiadea L. Their structures were elucidated
unambiguously by spectroscopic methods such as 1D and 2D NMR as well as HRESIMS. The anti-inflammatory and
analgesic activities of the isolated compounds were also evaluated in vitro. Among the tested compounds, 1, 2, and 4
showed potent anti-inflammatory activity through both nitrite and IL-6 pathways at 200 µM. Besides, compound 1
exhibited the highest decrease in PGE2 level, with a higher inhibition rate compared to positive control indomethacin.

Anahtar Kelimeler

Gentiana asclepiadea Gentianaceae secoiridoid depressine anti-inflammatory and analgesic activity

Kaynakça

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Yıl 2023, Cilt: 27 Sayı: 3, 1202 - 1212, 28.06.2025

Rima Konya Konuk , Rengin Reis , Hande Sipahi , Anita Barta Judit Hohmann Hasan Kırmızıbekmez

Öz

Kaynakça

  • Jiang M, Cui BW, Wu YL, Nan JX, Lian LH. Genus Gentiana: A review on phytochemistry, pharmacology and molecular mechanism. J Ethnopharmacol. 2021; 264:113391 https://doi.org/10.1016/j.jep.2020.113391
  • Wang YM, Xu M, Wang D, Yang CR, Zeng Y, Zhang YJ. Anti-inflammatory compounds of “qin-Jiao”, the roots of Gentiana dahurica (Gentianaceae). J Ethnopharmacol. 2013; 147(2): 341–348. https://doi.org/10.1016/j.jep.2013.03.016
  • Guo K, Zhou TT, Ren X, Li D, Hu H, Liu YC, Liu Y, Li SH. Secoiridoids and triterpenoids from the traditional Tibetan medicine Gentiana veitchiorum and their immunosuppressive activity. Phytochemistry. 2021; 192:112961. https://doi.org/10.1016/j.phytochem.2021.112961
  • Nastasijević B, Lazarević-Pašti T, Dimitrijević-Branković S, Pašti I, Vujačić A, Joksić G, Vasic V. Inhibition of myeloperoxidase and antioxidative activity of Gentiana lutea extracts. J Pharm Biomed Anal. 2012; 66: 191–196. https://doi.org/10.1016/j.jpba.2012.03.052
  • Mustafa AM, Caprioli G, Dikmen M, Kaya E, Maggi F, Sagratini G, Vittori S, Öztürk Y. Evaluation of neuritogenic activity of cultivated, wild and commercial roots of Gentiana lutea L. J Funct Foods. 2015; 19:164–173. https://doi.org/10.1016/j.jff.2015.09.018
  • Davis PH, Flora of Turkey and the East Aegean Islands, sixth ed., Edinburgh University Press, Edinburgh, United Kingdom 1979; 183-191.
  • Baytop T, Türkiye’de Bitkilerle Tedavi (Geçmişte ve Bugün), ilaveli ikinci baskı. Nobel Tıp Kitabevleri 1999; 174–175. Matejić JS, Stefanović N, Ivković M, Živanović N, Marin PD, Džamić AM. Traditional uses of autochthonous medicinal and ritual plants and other remedies for health in Eastern and South-Eastern Serbia. J Ethnopharmacol. 2020; 261:113186. https://doi.org/10.1016/j.jep.2020.113186
  • Menković N, Šavikin K, Tasić S, Zdunić G, Stešević D, Milosavljević S, Vincek D. Ethnobotanical study on traditional uses of wild medicinal plants in Prokletije Mountains (Montenegro). J Ethnopharmacol. 2011; 133(1): 97–107. https://doi.org/10.1016/j.jep.2010.09.008
  • Nićiforović N, Mihailović V, Mašković P, Solujić S, Stojković A, Muratspahić DP. Antioxidant activity of selected plant species; potential new sources of natural antioxidants. Food Chem Toxicol. 2010; 48: 3125–3130. https://doi.org/10.1016/j.fct.2010.08.007
  • Šarić-Kundalić B, Dobeš C, Klatte-Asselmeyer V, Saukel J. Ethnobotanical survey of traditionally used plants in human therapy of east, north and north-east Bosnia and Herzegovina. J Ethnopharmacol. 2011; 133: 1051–1076. https://doi.org/10.1016/j.jep.2010.11.033
  • Hudecová A, Kusznierewicz B, Hašplová K, Huk A, Magdolenová Z, Miadoková E, Gálová E, Dušinská M. Gentiana asclepiadea exerts antioxidant activity and enhances DNA repair of hydrogen peroxide- and silver nanoparticles- induced DNA damage. Food Chem Toxicol. 2012; 50: 3352–3359. https://doi.org/10.1016/j.fct.2012.06.017
  • Mihailović V, Mihailović M, Uskoković A, Arambašić J, Mišić D, Stanković V, Katanić J, Mladenović M, Solujić S, Matić S. Hepatoprotective effects of Gentiana asclepiadea L. extracts against carbon tetrachloride-induced liver injury in rats. Food Chem Toxicol. 2013; 52: 83–90. https://doi.org/10.1016/j.fct.2012.10.034
  • Buza V, Niculae M, Hanganu D, Pall E, Burtescu RF, Olah NK, Matei-Lațiu MC, Vlasiuc I, Iozon I, Szakacs AR, Ielciu I, Ștefănuț LC. Biological activities and chemical profile of Gentiana asclepiadea and Inula helenium ethanolic extracts. Molecules 2022; 27: 3560. https://doi.org/10.3390/molecules27113560
  • Stefanović O, Ličina B, Vasić S, Radojević I, Čomić L. Bioactive extracts of Gentiana asclepiadea: Antioxidant, antimicrobial, and antibiofilm activity. Bot Serb. 2018; 42(2) :223–229. https://doi.org/10.5281/zenodo.1468319
  • Goetz M, Jacot-Guillarmod A. Contribution à la phytochimie du genre Gentiana . XXII. Identification de nouveaux O- glucosides de la mangiférine dans Gentiana asclepiadea L. Helv Chim Acta. 1977; 60: 2104–2106. https://doi.org/10.1002/hlca.19770600633
  • Kitanov GM, Spassov SL. A naphthodipyranodione from Gentiana asclepiadea. Phytochemistry. 1992; 31: 1067–1068. https://doi.org/10.1016/0031-9422(92)80080-X
  • Kitanov GM, Van DT, Asenov I. Chemical composition of the roots of Gentiana asclepiadea. Chem Nat Compd. 1991; 27: 369–370. https://doi.org/10.1007/BF00630332
  • Goetz M, Jacot-Guillarmod A. Contribution à la phytochimie de genre Gentiana. XXIV. Nouveaux C-glycosides flavoniques dans les feuilles de Gentiana asclepiadea L. Helv Chim Acta. 1978; 61: 1373–1375. https://doi.org/10.1002/hlca.19780610420
  • Santos ES, Oliveira CDdM, Menezes IRA, do Nascimento EP, Correia DB, de Alencar CDC, Sousa MdF, Lima CNF, Monteiro ÁB, de Souza CPE, Delmondes GdA, Bezerra DS, Garcia FAdO, Boligon AA, da Costa JGM, Coutinho HDM, Felipe CFB, Kerntopf MR. Anti-inflammatory activity of herb products from Licania rigida Benth. Complement Ther Med. 2019; 45: 254–261. https://doi.org/10.1016/j.ctim.2019.06.001
  • Zhao H, Wu L, Yan G, Chen Y, Zhou M, Wu Y, Li Y. Inflammation and tumor progression: signaling pathways and targeted intervention. Signal Transduct Target Ther. 2021; 6(1):263. https://doi.org/10.1038/s41392-021-00658-5
  • Schini-Kerth VB. Vascular biosynthesis of nitric oxide: effect on hemostasis and fibrinolysis. Transfus Clin Biol. 1999; 6(6): 355–363. https://doi.org/10.1016/S1246-7820(00)88980-6
  • Uciechowski P, Dempke WCM. Interleukin-6: A masterplayer in the cytokine network. Oncology. 2020; 98: 131–137. https://doi.org/10.1159/000505099
  • Ricciotti E, FitzGerald GA. Prostaglandins and Inflammation. Arterioscler Thromb Vasc Biol. 2011; 31: 986–1000. https://doi.org/10.1161/ATVBAHA.110.207449
  • Konya R, Reis R, Sipahi H, Barta A, Hohmann J, Kırmızıbekmez H. Secondary metabolites from Gentiana cruciata L. and their anti-inflammatory and analgesic activities. Nat Prod Res. 2022: 1–8. https://doi.org/10.1080/14786419.2022.2144301
  • Kırmızıbekmez H, Tatar D, Erdoğan M, Kúsz N, Hohmann J. A new depside and a new secoiridoid from the aerial parts of Gentiana olivieri from flora of Turkey. Nat Prod Res. 2022; 36: 2208–2214. https://doi.org/10.1080/14786419.2020.1825429
  • Chulia AJ, Vercauteren J, Mariotte AM. Iridoids and flavones from Gentiana depressa. Phytochemistry. 1996; 42: 139– 143. https://doi.org/10.1016/0031-9422(95)00900-0Mpondo-Mpondo E, Chulia AJ. 6′ -O-β-D-Glucosyl Gentiopicroside: A New secoiridoid from Gentiana asclepiadea. Planta Med. 1988; 54: 185–186. https://doi.org/10.1055/s-2006-962394
  • Calis I, Lahloub MF, Sticher O. Loganin, loganic acid and periclymenoside, a new biosidic ester iridoid glucoside from Lonicera periclymenum L. (Caprifoliaceae). Helv Chim Acta. 1984; 67(1): 160–165. https://doi.org/10.1002/hlca.19840670119
  • Kuo SH, Yen MH, Chung MI, Lin CN. A flavone C-glycoside and an aromatic glucoside from Gentiana species. Phytochemistry. 1996; 41(1): 309–312. https://doi.org/10.1016/0031-9422(95)00528-5
  • Ramarathnam N, Osawa T, Namiki M, Kawakishi S. Chemical studies on novel rice hull antioxidants. 2. Identification of isovitexin, a C-glycosyl flavonoid. J Agric Food Chem. 1989; 37: 316–319. https://doi.org/10.1021/jf00086a009
  • Djemgou PC, Hussien TA, Hegazy MEF, Ngandeu F, Neguim G, Tane P, Mohamed AEHH. C-Glucoside xanthone from the stem bark extract of Bersama engleriana. Pharmacognosy Res. 2010; 2: 229. https://doi.org/10.4103/0974- 8490.69110
  • Huang R, Wang X, Liu H, Hu HM, Hu WY, Chen G. Chemical constituents from Gentiana crassicaulis Duthie ex Burk. Biochem Syst Ecol 2020; 92:104115. https://doi.org/10.1016/j.bse.2020.104115
  • Popović Z, Krstić-Milošević D, Marković M, Vidaković V, Bojović S. Gentiana asclepiadea L. from two high mountainous habitats: inter- and intrapopulation variability based on species’ phytochemistry. Plants (Basel). 2021;10:140. https://doi.org/10.3390/plants10010140
  • Szucs Z, Dános B, Nyiredy Sz. Comparative analysis of the underground parts of Gentiana species by HPLC with diode-array and mass spectrometric detection. Chromatographia 2002; 56(1): S19–S23. https://doi.org/10.1007/BF02494108
  • Hudecová A, Kusznierewicz B, Runden-Pran E, Magdolenova Z, Hasplova K, Rinna A, Fjellsbo LM, Kruszewski M, Lankoff A, Sandberg WJ, Refsnes M, Skuland T, Schwarze P, Brunborg, G, Bjoras M, Collins A, Miadokova E, Galova E, Dusinska M. Silver nanoparticles induce premutagenic DNA oxidation that can be prevented by phytochemicals from Gentiana asclepiadea. Mutagenesis 2012; 27(6): 759-769. https://doi.org/10.1093/mutage/ges046
  • Goetz M, Hostettmann K, Jacot-Guillarmod A. A new C-glycosylflavone from Gentiana asclepiadea. Phytochemistry 1976;15: 2014. https://doi.org/10.1016/S0031-9422(00)88886-X
  • Çalis I, Ersöz T, Chulia AJ, Rüedi P. Sleptemfidoside: a new bis-iridoid diglucoside from Gentiana septemfida. J Nat Prod. 1992; 55(3): 385–388. https://doi.org/10.1021/np50081a018
  • Fu L, Gu R, Zhang CH, Li F, Zhong SH, Ma YY, Deng W. Chemical constituents of n-butanol fraction from Tibetan medicine Gentianae szechenyii Spray. Chin Tradit Herb Drugs. 2018; 49: 1002–1006.
  • Bahiense JB, Marques FM, Figueira MM, Vargas TS, Kondratyuk TP, Endringer DC, Scherer R, Fronza M. Potential anti-inflammatory, antioxidant and antimicrobial activities of Sambucus australis. Pharm Biol. 2017; 55: 991–997. https://doi.org/10.1080/13880209.2017.1285324
  • Piknova B, Schechter AN. Measurement of nitrite in blood samples using the ferricyanide-based hemoglobin oxidation assay. Methods Mol Biol. 2011; 704: 39–56. https://doi.org/10.1007/978-1-61737-964-2_4
  • Giustarini D, Rossi R, Milzani A, Dalle‐Donne I. Nitrite and nitrate measurement by Griess reagent in human plasma: evaluation of interferences and standardization. Methods Enzymol. 2008; 440: 361–380. https://doi.org/10.1016/S0076-6879(07)00823-3
  • Tanaka T, Narazaki M, Kishimoto T. IL-6 in inflammation, immunity, and disease. Cold Spring Harb Perspect Biol. 2014; 6: a016295–a016295. https://doi.org/10.1101/cshperspect.a016295
  • Lee AJ, Cho KJ, Kim JH. MyD88–BLT2-dependent cascade contributes to LPS-induced interleukin-6 production in mouse macrophage. Exp Mol Med. 2015; 47: e156–e156. 1-9. https://doi.org/10.1038/emm.2015.8
  • Kawabata A. Prostaglandin E2 and pain-an update. Biol Pharm Bull. 2011; 34: 1170–1173. https://doi.org/10.1248/bpb.34.1170
  • Wang M, Li H, Wang Y, Hao Y, Huang Y, Wang X, Lu Y, Du Y, Fu F, Xin W, Zhang L. Anti-rheumatic properties of gentiopicroside are associated with suppression of ROS-NF-κB-NLRP3 axis in fibroblast-like synoviocytes and NF- κB pathway in adjuvant-induced arthritis. Front Pharmacol. 2020;11:515. https://doi.org/10.3389/fphar.2020.00515
  • He M, Hu C, Chen M, Gao Q, Li L, Tian W. Effects of gentiopicroside on activation of NLRP3 inflammasome in acute gouty arthritis mice induced by MSU. J Nat Med. 2022; 76: 178–187. https://doi.org/10.1007/s11418-021-01571-5
  • Wang Q, Zhou X, Yang L, Luo M, Han L, Lu Y, Shi Q, Wang Y, Liang Q. Gentiopicroside (GENT) protects against sepsis induced by lipopolysaccharide (LPS) through the NF-κB signaling pathway. Ann Transl Med. 2019; 7(23): 731. https://doi.org/10.21037/atm.2019.11.126
  • Zhang Q, Zhang J, Xia P, Peng X, Li H, Jin H, Li Y, Yang J, Zhao L. Anti-inflammatory activities of gentiopicroside against iNOS and COX-2 targets. Chin Herb Med. 2019; 11: 108–112. https://doi.org/10.1016/j.chmed.2018.10.004
  • Dzydzan O, Brodyak I, Sokół-Łętowska A, Kucharska AZ, Sybirna N. Loganic acid, an iridoid glycoside extracted from Cornus mas l. fruits, reduces of carbonyl/oxidative stress biomarkers in plasma and restores antioxidant balance in leukocytes of rats with streptozotocin-induced diabetes mellitus. Life(Basel). 2020; 10(12): 349. https://doi.org/10.3390/life10120349
  • Kim B, Lee KY, Park B. Isoorientin inhibits amyloid β25–35-induced neuronal inflammation in BV2 cells by blocking the NF-κB signaling pathway. Molecules. 2021;26:7056. https://doi.org/10.3390/molecules26227056
  • Lin CM, Huang ST, Liang YC, Lin MS, Shih CM, Chang YC, Chen TY, Chen CT. Isovitexin suppresses lipopolysaccharide-mediated inducible nitric oxide synthase through inhibition of NF-kappa B in mouse macrophages. Planta Med. 2005; 71: 748–753. https://doi.org/10.1055/s-2005-871287
  • Sozański T, Kucharska AZ, Rapak A, Szumny D, Trocha M, Merwid-Ląd A, Dzimira S, Piasecki T, Piórecki N, Magdalan J, Szeląg A. Iridoid–loganic acid versus anthocyanins from the Cornus mas fruits (cornelian cherry): Common and different effects on diet-induced atherosclerosis, PPARs expression and inflammation. Atherosclerosis 2016; 254: 151–160. https://doi.org/10.1016/j.atherosclerosis.2016.10.001
  • Anilkumar K, Reddy GV, Azad R, Yarla NS, Dharmapuri G, Srivastava A, Kamal MA, Pallu R. Evaluation of Anti- Inflammatory Properties of Isoorientin Isolated from Tubers of Pueraria tuberosa. Oxid Med Cell Longev. 2017; 2017:5498054. https://doi.org/10.1155/2017/5498054
  • Lv H, Yu Z, Zheng Y, Wang L, Qin X, Cheng G, Ci X. Isovitexin exerts anti-inflammatory and anti-oxidant activities on lipopolysaccharide-induced acute lung injury by ınhibiting MAPK and NF-κB and activating HO-1/Nrf2 pathways. Int J Biol Sci. 2016;12:72–86. https://doi.org/10.7150/ijbs.13188
  • Shin JS, Noh YS, Kim DH, Cho YW, Lee KT. Mangiferin isolated from the rhizome of Anemarrhena asphodeloides inhibits the LPS-induced nitric oxide and prostagladin E2 via the NF-κB inactivation in inflammatory macrophages. Nat Prod Sci. 2008; 14: 206–213.
  • Sipahi H, Orak D, Reis R, Yalman K, Şenol O, Palabiyik-Yücelik SS, Deniz İ, Algül D, Guzelmeric, E, Celep ME, Argin S, Özkan F, Halıcı Z, Aydın A, Yesilada E. A comprehensive study to evaluate the wound healing potential of okra (Abelmoschus esculentus) fruit. J Ethnopharmacol. 2022; 287:114843 https://doi.org/10.1016/j.jep.2021.114843
Toplam 55 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmakognozi
Bölüm Articles
Yazarlar

Rima Konya Konuk 0000-0001-6228-4369

Rengin Reis 0000-0002-3484-2201

Hande Sipahi 0000-0001-6482-3143

Anita Barta

Judit Hohmann 0000-0002-2887-6392

Hasan Kırmızıbekmez 0000-0002-6118-8225

Yayımlanma Tarihi 28 Haziran 2025
Yayımlandığı Sayı Yıl 2023 Cilt: 27 Sayı: 3

Kaynak Göster

APA Konya Konuk, R., Reis, R., Sipahi, H., Barta, A., vd. (2025). Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities. Journal of Research in Pharmacy, 27(3), 1202-1212.
AMA Konya Konuk R, Reis R, Sipahi H, Barta A, Hohmann J, Kırmızıbekmez H. Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities. J. Res. Pharm. Haziran 2025;27(3):1202-1212.
Chicago Konya Konuk, Rima, Rengin Reis, Hande Sipahi, Anita Barta, Judit Hohmann, ve Hasan Kırmızıbekmez. “Iridoids and Flavonoids from the Aerial Parts of Gentiana Asclepiadea L. With Anti-Inflammatory and Analgesic Activities”. Journal of Research in Pharmacy 27, sy. 3 (Haziran 2025): 1202-12.
EndNote Konya Konuk R, Reis R, Sipahi H, Barta A, Hohmann J, Kırmızıbekmez H (01 Haziran 2025) Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities. Journal of Research in Pharmacy 27 3 1202–1212.
IEEE R. Konya Konuk, R. Reis, H. Sipahi, A. Barta, J. Hohmann, ve H. Kırmızıbekmez, “Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities”, J. Res. Pharm., c. 27, sy. 3, ss. 1202–1212, 2025.
ISNAD Konya Konuk, Rima vd. “Iridoids and Flavonoids from the Aerial Parts of Gentiana Asclepiadea L. With Anti-Inflammatory and Analgesic Activities”. Journal of Research in Pharmacy 27/3 (Haziran 2025), 1202-1212.
JAMA Konya Konuk R, Reis R, Sipahi H, Barta A, Hohmann J, Kırmızıbekmez H. Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities. J. Res. Pharm. 2025;27:1202–1212.
MLA Konya Konuk, Rima vd. “Iridoids and Flavonoids from the Aerial Parts of Gentiana Asclepiadea L. With Anti-Inflammatory and Analgesic Activities”. Journal of Research in Pharmacy, c. 27, sy. 3, 2025, ss. 1202-1.
Vancouver Konya Konuk R, Reis R, Sipahi H, Barta A, Hohmann J, Kırmızıbekmez H. Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities. J. Res. Pharm. 2025;27(3):1202-1.