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Natural Product Research
Formerly Natural Product Letters
Volume 37, 2023 - Issue 2
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Research Articles

New coumarin glycosides from endemic Prangos heyniae H. Duman & M.F. Watson

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Pages 227-239 | Received 17 Mar 2021, Accepted 20 Jul 2021, Published online: 04 Aug 2021

References

  • Abyshev A. 1974. Structure of some components of the roots of Prangos ferulacea. Chem Nat Compd. 10(5):581–585.
  • Ahmed J, Guvenc A, Kucukboyaci N, Baldemir A, Coskun M. 2011. Total phenolic contents and antioxidant activities of Prangos Lindl. (Umbelliferae) species growing in Konya province (Turkey). Turk J Biol. 35(3):353–360.
  • Altundag E, Ozturk M. 2011. Ethnomedicinal studies on the plant resources of east Anatolia, Turkey. Procedia Soc Behav Sci. 19:756–777.
  • Aytac Z, Duman H. 2016. Prangos abieticola (Apiaceae), a new species from South Anatolia, Turkey. Edinb J Bot. 73(1):125–131.
  • Başer KHC, Özek T, Demirci B, Duman H. 2000. Composition of the essential oil of Prangos heyniae H. Duman et MF Watson, a new endemic from Turkey. Flavour Fragr J. 15(1):47–49.
  • Baytop T. 1999. Türkiye'de bitkiler ile tedavi: geçmişte ve bugün [Phytotherapy in Turkey: past and present]. Istanbul: Nobel Tıp Kitabevleri. Turkish.
  • Behçet L, Yapar Y, Olgun S. 2019. Prangos aricakensis (Apiaceae), a new species from eastern Turkey. Phytotaxa. 401(1):55–63.
  • Bruno M, Ilardi V, Lupidi G, Quassinti L, Bramucci M, Fiorini D, Venditti A, Maggi F. 2019. The nonvolatile and volatile metabolites of Prangos ferulacea and their biological properties. Planta Med. 85(11–12):815–824.
  • Chen C-C, Huang Y-L, Huang F-I, Wang C-W, Ou J-C. 2001. Water-soluble glycosides from Ruta graveolens. J Nat Prod. 64(7):990–992.
  • Dissanayake AA, Ameen BA, Nair MG. 2017. Lipid peroxidation and cyclooxygenase enzyme inhibitory compounds from Prangos haussknechtii. J Nat Prod. 80(9):2472–2477.
  • Duman H, Watson M. 1999. Ekimia, a new genus of Umbelliferae, and two new taxa of Prangos Lindl. (Umbelliferae) from southern Turkey. Edinb J Bot. 56(2):199–209.
  • Elgamal MHA, Shalaby NM, Duddeck H, Hiegemann M. 1993. Coumarins and coumarin glucosides from the fruits of Ammi majus. Phytochemistry. 34(3):819–823.
  • Fan B-Y, He Y, Lu Y, Yang M, Zhu Q, Chen G-T, Li J-L. 2019. Glycosidic acids with unusual aglycone units from Convolvulus arvensis. J Nat Prod. 82(6):1593–1598.
  • Farooq S, Dangroo NA, Priya D, Banday JA, Sangwan PL, Qurishi MA, Koul S, Saxena AK. 2014. Isolation, cytotoxicity evaluation and HPLC-quantification of the chemical constituents from Prangos pabularia. PLoS One. 9(10):e108713.
  • Farozi A, Shah SA, Banday JA. 2016. Structural and optical studies of 7-methoxy-8-(3-metrhylbut-2-enyl)-2-chromenone (osthol), a plant based coumarin. Optik. 127(5):2802–2805.
  • Fujioka T, Furumi K, Fujii H, Okabe H, Mihashi K, Nakano Y, Matsunaga H, Katano M, Mori M. 1999. Antiproliferative constituents from Umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chem Pharm Bull. 47(1):96–100.
  • Gokay O, Kuhner D, Los M, Gotz F, Bertsche U, Albert K. 2010. An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix Imperatoriae. Anal Bioanal Chem. 398(5):2039–2047.
  • Guner A. 2012. In: Guner A, editor. Türkiye bitkileri listesi: (damarlı bitkiler) [A checklist of the Flora of Turkey: Vascular plants]. 1st ed. Istanbul: Nezahat Gökyiğit Botanik Bahçesi Yayınları. Turkish.
  • Henke MT, Kenny DJ, Cassilly CD, Vlamakis H, Xavier RJ, Clardy J. 2019. Ruminococcus gnavus, a member of the human gut microbiome associated with Crohn's disease, produces an inflammatory polysaccharide. Proc Natl Acad Sci U S A. 116(26):12672–12677.
  • Hitotsuyanagi Y, Kojima H, Ikuta H, Takeya K, Itokawa H. 1996. Identification and structure-activity relationship studies of osthol, a cytotoxic principle from Cnidium monnieri. Bioorg Med Chem Lett. 6(15):1791–1794.
  • IPNI. 2021. Prangos heyniae H. Duman & M.F.Watson. [accessed 2021 May 10]. https://www.ipni.org/n/1008210-1.
  • Kaval I, Behcet L, Cakilcioglu U. 2014. Ethnobotanical study on medicinal plants in Gecitli and its surrounding (Hakkari-Turkey). J Ethnopharmacol. 155(1):171–184.
  • Khaikin M, Rakova N. 1968. Ultraviolet spectra of some 6, 7-and 7, 8-dihydroxycoumarins. J Appl Spectrosc. 8(6):640–642.
  • Kim NM, Kim J, Chung HY, Choi JS. 2000. Isolation of luteolin 7-O-rutinoside and esculetin with potential antioxidant activity from the aerial parts of Artemisia montana. Arch Pharm Res. 23(3):237–239.
  • Kogure K, Yamauchi I, Tokumura A, Kondou K, Tanaka N, Takaishi Y, Fukuzawa K. 2004. Novel antioxidants isolated from plants of the genera Ferula, Inula, Prangos and Rheum collected in Uzbekistan. Phytomedicine. 11(7–8):645–651.
  • Lee T-H, Chen Y-C, Hwang T-L, Shu C-W, Sung P-J, Lim Y-P, Kuo W-L, Chen J-J. 2014. New coumarins and anti-inflammatory constituents from the fruits of Cnidium monnieri. Int J Mol Sci. 15(6):9566–9578.
  • Lu Y, He Y, Yang M, Fan B-Y. 2021. Arvensic acids K and L, components of resin glycoside fraction from Convolvulus arvensis. Nat Prod Res. 35(14):2303–2307.
  • Lyskov DF, Degtjareva GV, Samigullin TH, Pimenov MG. 2017. The revision of Prangos subsections Koelzella and Fedtschenkoana (Apiaceae) with some notes to phylogeny and biogeography of the genus: molecular and morphological evidences. Plant Syst Evol. 303(7):815–826.
  • Mah SH, Ee GCL, Teh SS, Sukari MA. 2015. Calophyllum inophyllum and Calophyllum soulattri source of anti-proliferative xanthones and their structure-activity relationships. Nat Prod Res. 29(1):98–101.
  • Massumi MA, Fazeli MR, Alavi SHR, Ajani Y. 2007. Chemical constituents and antibacterial activity of essential oil of Prangos ferulacea (L.) Lindl. fruits. Iran J Pharm Sci. 3(3):171–176.
  • Mottaghipisheh J, Kiss T, Tóth B, Csupor D. 2020. The Prangos genus: a comprehensive review on traditional use, phytochemistry, and pharmacological activities. Phytochem Rev. 19(6):1449–1470.
  • Nematollahi-Mahani S, Rezazadeh-Kermani M, Mehrabani M, Nakhaee N. 2007. Cytotoxic effects of Teucrium polium on some established cell lines. Pharm Biol. 45(4):295–298.
  • Numonov S, Bobakulov K, Numonova M, Sharopov F, Setzer WN, Khalilov Q, Begmatov N, Habasi M, Aisa HA. 2018. New coumarin from the roots of Prangos pabularia. Nat Prod Res. 32(19):2325–2332.
  • Oke-Altuntas F, Aslim B, Duman H, Gulpinar AR, Kartal M. 2015. The relative contributions of chlorogenic acid and rutin to antioxidant activities of two endemic Prangos (Umbelliferae) species (P. heyniae and P. denticulata). J Food Biochem. 39(4):409–416.
  • Özek G, Bedir E, Tabanca N, Ali A, Khan IA, Duran A, Başer KHC, Özek T. 2018. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H. Duman & M.F. Watson essential oil and mosquitocidal activity of the essential oils. Open Chem J. 16(1):453–467.
  • POWO. 2021. Prangos heyniae H. Duman & M.F.Watson. [accessed 2021 May 10]. http://powo.science.kew.org/taxon/1008210-1.
  • Prawat H, Mahidol C, Ruchirawat S, Prawat U, Tuntiwachwut-Tikul P, Tooptakong U, Taylor WC, Pakawatchai C, Skeleton BW, White AH. 1995. Cyanogenic and non-cyanogenic glycosides from Manihot esculenta. Phytochemistry. 40(4):1167–1173.
  • Razavi SM, Nazemiyeh H, Delazar A, Hajiboland R, Rahman MM, Gibbons S, Nahar L, Sarker SD. 2008. Coumarins from the roots of Prangos uloptera. Phytochem Lett. 1(3):159–162.
  • Razavi SM, Zahri S, Nazemiyeh H, Zarrini G, Mohammadi S, Abolghassemi-Fakhri M-A. 2009. A furanocoumarin from Prangos uloptera roots, biological effects. Nat Prod Res. 23(16):1522–1527.
  • Razavi SM, Zarrini G, Rad FG. 2011. Isoarnottinin 4′-glucoside, a glycosylated coumarin from Prangos uloptera, with biological activity. Russ J Bioorg Chem. 37(2):240–243.
  • Sharma RK, Negi DS, Gibbons S, Otsuka H. 2008. Chemical and antibacterial constituents of Skimmia anquetelia. Planta Med. 74(2):175–177.
  • Shikishima Y, Takaishi Y, Honda G, Ito M, Takfda Y, Kodzhimatov OK, Ashurmetov O, Lee KH. 2001. Chemical constituents of Prangos tschiniganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity. Chem Pharm Bull (Tokyo). 49(7):877–880.
  • Shokoohinia Y, Hosseinzadeh L, Alipour M, Mostafaie A, Mohammadi-Motlagh H-R. 2014. Comparative evaluation of cytotoxic and apoptogenic effects of several coumarins on human cancer cell lines: osthole induces apoptosis in p53-deficient H1299 cells. Adv Pharmacol Sci. 2014:847574.
  • Šimčíková D, Kotik M, Weignerová L, Halada P, Pelantová H, Adamcová K, Křen V. 2015. α‐L‐rhamnosyl‐β‐D‐glucosidase (rutinosidase) from Aspergillus niger: characterization and synthetic potential of a novel diglycosidase. Adv Synth Catal. 357(1):107–117.
  • Tada Y, Shikishima Y, Takaishi Y, Shibata H, Higuti T, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O, et al. 2002. Coumarins and gamma-pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release. Phytochemistry. 59(6):649–654.
  • Tan N, Yazıcı-Tütüniş S, Bilgin M, Tan E, Miski M. 2017. Antibacterial activities of pyrenylated coumarins from the roots of Prangos hulusii. Molecules. 22(7):1098.
  • ThePlantList. 2013. Prangos heyniae H. Duman & M.F. Watson. [accessed 2021 May 10]. http://www.theplantlist.org/tpl1.1/record/kew-2404848.
  • Tjahjandarie TS. 2014. Coumarins from the stem bark of Feronia limonia. J Chem Pharm Res. 6:499–504.
  • Ulubelen A, Topcu G, Tan N, Olcal S, Johansson C, Ucer M, Birman H, Tamer S. 1995. Biological activities of a Turkish medicinal plant, Prangos platychlaena. J Ethnopharmacol. 45(3):193–197.
  • WorldFloraOnline. 2021. Prangos heyniae H. Duman & M.F. Watson. [accessed 2021 May 10]. http://www.worldfloraonline.org/taxon/wfo-0000392431.
  • Yang C-P, Shie P-H, Huang G-J, Chien S-C, Kuo Y-H. 2019. New anti-inflammatory flavonol glycosides from Lindera akoensis Hayata. Molecules. 24(3):563.
  • Yang L-L, Wang M-C, Chen L-G, Wang C-C. 2003. Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines. Planta Med. 69(12):1091–1095.

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