Kedikulağı (Ophrys sphegodes subsp. mammosa, Orchidaceae) Yumrularındaki Fenollerin Tespiti

Yıl 2023, Cilt: 28 Sayı: 3, 818 - 829, 29.12.2023

Mehmet Aybeke

https://doi.org/10.53433/yyufbed.1230023

Öz

Fenolik bileşiklerin birçok antioksidan, antimikrobiyal, antienflamatuar, antioksidan, antitümör, kardiyoprotektif, nöroprotektif ve antidiyabetik aktiviteleri vardır. Orkidelerde fenoliklerle ilgili bilgiler çok azdır ve orkide yumruları önemli droglardan biridir. Bu nedenle çalışmada; hazır materyal olarak elimizde bulunan Orchidaceae familyasından Ophrys sphegodes Mill. subsp. mammosa (Desf.) Soó ex E. Nelson (Kedikulağı) taksonuna ait yumrularda fenolik bileşiklerin tespiti amaçlanmıştır. Bunun için çiçeklenme aşamasında bitkilerden yumrular alınmış, bu yumrulardan LC-MS/MS ile fenolik bileşik analizi yapılmıştır. Yumru örneklerinde 27 değişik fenol taranmış ve 12 fenole rastlanmıştır. Yapılan analiz sonucunda O. sphegodes subsp. mammosa yumrularında Gallik Asit, Protokatekuik Asit, 2,5-Dihidroksibenzoik Asit, Klorogenik Asit, P-kumarik asit, Rutin, Trans Ferrulik Asit, Propil Gallate, Kersetin, Lutolein, Kamferol, Izoramnetin tespit edilmiştir. En fazla fenol 901.6510 ng/gr ile Kamferol olurken, en az fenol ise 1,0168 ng/gr ile Propil Gallat’dır. Nicelik olarak ikinci sırada en fazla olan fenol 392.7265 ng/gr ile P-kumarik asit, üçüncü sırada 375.0809 ng/gr ile Trans Ferrulik Asit, dördüncü sırada 69.4946 ng/gr ile Rutin’dir. Diğer kalan fenollerin miktarları 20 ng/gr’ın altındadır. Sonuçlar, yakın ve uzak taksonlarla yapılan güncel çalışmalarla karşılaştırılmış ve incelenen taksonun olası güçlü antioksidan ve antibakteriyel etkileri ile ilaç endüstrisi ve sürdürülebilir orkide tarımsal üretim için iyi bir potansiyele sahip olduğu vurgulanmıştır.

Anahtar Kelimeler

Fenol, Ophrys, Orkide, Yumru

Detection of Phenols in Tubers of Ophrys sphegodes subsp. mammosa (Orchidaceae)

Öz

Phenolic compounds have many antioxidant, antimicrobial, anti-inflammatory, antioxidant, antitumor, cardioprotective, neuroprotective and antidiabetic activities. There is very little information about phenolics in orchids and orchid tubers are one of the important drugs. Therefore, in the study; It was aimed to detect phenolic compounds in tubers of Ophrys sphegodes Mill. subsp. mammosa (Desf.) Soó ex E. Nelson (Kitten ear) from the Orchidaceae family, which we have as ready-made material. For this, tubers were taken from the plants at the flowering stage, and phenolic compounds were analyzed by LC-MS/MS from these tubers. 27 different phenols were screened in tuber samples and 12 phenols were found. As a result of the analysis, O. sphegodes subsp. mammosa Gallic Acid, Protocatechuic Acid, 2,5-Dihydroxybenzoic Acid, Chlorogenic Acid, P-coumaric acid, Rutin, Trans Ferulic Acid, Propyl Gallate, Quercetin, Luteolin, Kaempferol, Isorhamnetin were detected in tubers. The highest phenol is Kampferol with 901.6510 ng/gr, while the least phenol is Propyl Gallate with 1.0168 ng/gr. P-coumaric acid with 392.7265 ng/gr is the second highest in quantity, Trans Ferrulic Acid is at the third place with 375.0809 ng/gr, and Rutin is at the fourth place with 69.4946 ng/gr. The amounts of other remaining phenols are below 20 ng/gr. The results were compared with the most recent similar studies with close and distant taxa, and it was emphasized that the examined taxon has a good potential for the pharmaceutical industry and sustainable orchid agricultural production with its possible strong antioxidant and antibacterial effects.

Anahtar Kelimeler

Ophrys, Orchid, Phenol, Tuber

Kaynakça

• Ali, F., Rahul, S., Jyoti, F., Naz, M., Ashafaq, M., Shahid, M. & Siddique, Y.H. (2019). Therapeutic potential of luteolin in transgenic Drosophila model of Alzheimer’s disease. Neuroscience Letters, 692, 90-99. doi:10.1016/j.neulet.2018.10.053
• Aliyazıcıoğlu, R., Korkmaz, N., Akkaya, Ş., Şener, S. Ö., Özgen, U., & Karaoğlu Ş. A. (2018). Dactylorhiza osmanica’nın topraküstü kısımlarında antioksidan, antimikrobiyal ve tirozinaz inhibitör aktivitelerinin araştırılması. Fırat Tıp Dergisi, 23, 2, 50-57.
• Attri, L. K., Bhanwra, R. K., & Nayyar, H. (2020). Pollination induced embryology studies in Aerides multiflora (ROXB.). International Journal of Botanical Studies, 5, 4, 211–215. doi:10.1016/j.scienta.2008.01.009
• Babbar, S. B., & Singh, D. K. (2016). Protocols for In Vitro Mass Multiplication and Analysis of Medicinally Important Phenolics of a Salep orchid, Satyrium nepalense D. Don (“Salam Mishri”). In S. M. Jain (Ed), Protocols for In Vitro Cultures and Secondary Metabolite Analysis of Aromatic and Medicinal Plants. (pp 1-11). Berlin, Germany: Springer verlag. doi:10.1007/978-1-4939-3332-7_1
• Baghel, S. S., Shrivastava, N., Baghel, R. S., Agrawal, P., & Rajput, S. (2012). A review of Quercetin: Antıoxidant and anticancer properties. World Journal of Pharmacy and Pharmaceutıcal Scıences, 1, 1, 146-160. doi:10.1007/s00606-012-2541-9
• Ballabh, B., Chaurasia, O. P., Ahmed, Z., & Singh, S. B. (2008). Traditional medicinal plants of cold desert Ladakh-Used against kidney and urinary disorders. Journal of Ethnopharmacology, 118, 331 - 339. doi:10.1016/j.jep.2008.04.022
• Barone, E., Calabrese, V., & Mancuso, C. (2009). Ferulic acid and its therapeutic potential as a hormetin for age-related diseases. Biogerontology, 10, 97-108. doi:10.1007/s10522-008-9160-8
• Bayram, N. E., Canlı, D., Gerçek, Y. C., Bayram, S., Çelik, S., Güzel, F., Morgil, H., & Öz, G. C. (2020). Monofloral bal örneklerinin makrobesin ve mikrobesin seviyeleri ve fenolik bileşik özellikleri. Gıda ve Beslenme Araştırmaları Dergisi, 1, 311-322. doi:10.1007/s00606-012-2541-9
• Bulpitt, C. J., Li, Y., Bulpitt, P. F., & Wang, J. (2007). The use of orchids in Chinese medicine. Journal of Royal Society of Medicine, 100, 558 - 563. doi:10.1258/jrsm.100.12.558
• Celińska-Janowicz, K., Zaręba, I., Lazarek, U., Teul, J., Tomczyk, M., Pałka, J., & Miltyk, W. (2018). Constituents of propolis: chrysin, caffeic acid, p-coumaric acid, and ferulic acid induce PRODH/POX-dependent apoptosis in human tongue squamous cell carcinoma cell (CAL-27). Frontiers in Pharmacology, 9, 336. doi:10.3389/fphar.2018.00336
• Chimsook, T. (2016). Phytochemical screening, total phenolic content, antioxidant activities and cytotoxicity of Dendrobium signatum Leaves. MATEC Web of Conferences, 62, 03005, Geneve. doi:10.1051/matecconf/20166203005
• Cozzolino, S., & Widmer, A. (2005). Orchid diversity: an evolutionary consequence of deception? Trends in Ecology & Evolution, 20, 487-494. doi:10.1016/j.tree.2005.06.004
• Dalar, A., Guo, Y., Esim, N., Bengu, A. S., & Konczak, I. (2015). Health attributes of an endemic orchid from Eastern Anatolia, Dactylorhiza chuhensis Renz&Taub. – In vitro investigations. Journal of Herbal Medicine, 5, 77-85. doi:10.1016/j.hermed.2015.02.001
• Dan, Y., Liang-Yan, L., Zhong-Quan, C., Feng-Qing, X., Wei-Wei, F., Cheng-Ting, Z., Fa-Wu, D., Jun, Z., Zhong-Tao, D., & Jiang-Miao, H. (2015). Five new phenolic compounds from Dendrobium aphyllum. Fitoterapia, 100, 11-18. doi:10.1016/j.fitote.2014.11.004
• Deniz, İ. G. (2022). Ophrys L., Orchidaceae. In A. Güner, A. Kandemir, Y. Menemen, H. Yıldırım, S. Aslan, A. Ö. Çimen, I. Güner, G. Bona Eksi & F. Şen Gökmen (Eds). Resimli Türkiye Florası, Cilt 3a (ss 361-365) İstanbul, Türkiye: Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği Basımı, 1.baskı.
• EuroMed PlantBase. (2011). Ophrys sphegodes subsp. mammosa. http://ww2.bgbm.org/EuroPlusMed/PTaxonDetail.asp?NameCache=Ophrys%20mammosa&PTRefFk=8000000 Erişim tarihi: 16.10.2022.
• Di Ferdinando, M., Brunetti, C., Agati, G., & Tattini, M. (2014). Multiple functions of polyphenols in plants inhabiting unfavorable Mediterranean areas. Environmental and Experimental Botany, 103, 107-116. doi:10.1016/j.envexpbot.2013.09.012
• Ganesan, K., & Xu, B. (2017). A critical review on polyphenols and health benefits of black soybeans. Nutrients, 9(5), 455. doi:10.3390/nu9050455
• Garrido, J., Garrido, E. M., & Borges, F. (2012). Studies on the food additive propyl gallate: Synthesis, structural characterization, and evaluation of the antioxidant activity. Journal of Chemical Education, 89, 130-133. doi:10.1021/ed900025s
• Gong, G., Ying-Yun, G., Zhong-Lin, Z., Rahman, K., Su-Juan, W., Zhoug, S., Luana, X., & Zhang, H. (2020). Isorhamnetin: A review of pharmacological effects. Biomedicine & Pharmacotherapy, 128, 110301. doi:10.1016/j.biopha.2020.110301
• Gutiérrez-Sánchez, A., Monribot-Villanueva, J. L., Cocotle-Ronzón, Y., Martínez-Cruz, N. S., & Guerrero-Analco, J. A. (2020). Phenolic profile and antioxidant activity from wild and in vitro cultivated Rhynchostele rossii (Orchidaceae). Acta Botanica Mexicana, 127, e1665. doi:10.21829/abm127.2020.1665
• Güner, A., Aslan, S., Ekim, T., Vural, M., & Babaç, M. T. (2012). Türkiye Bitkileri Listesi (Damarlı Bitkiler). İstanbul, Türkiye: Nezahat Gökyiğit Botanik Bahçesi Yayınları Flora Dizisi 1.
• Hossain, M. M. (2011). Therapeutic orchids: traditional uses and recent advances – an overview. Fitoterapia, 82, 102-140. doi:10.1016/j.fitote.2010.09.007
• Hürkan, K., Ballı, Y. M., Hürkan, K. Y., & Demir, N. (2019). Bazı önemli salep orkidesi türlerinin toplam fenolik ve flavonoit içeriklerinin antioksidan ve antimikrobiyal aktivitelerinin belirlenmesi. Eskişehir Teknik Üniversitesi Bilim ve Teknoloji Dergisi, 191-202. doi:10.18036/estubtdc.598852
• Imran, M., Salehi, B., Sharifi-Rad, J., Gondal, T. A., Saeed, F., … & Estevinho, L. M. (2019). Kaempferol: A key emphasis to its anticancer potential. Molecules, 24, 2277. doi:10.3390/molecules24122277
• Kanski, J., Aksenova, M., Stoyanova, A., & Butterfield, D. A. (2002). Ferulic acid antioxidant protection against hydroxyl and peroxyl radical oxidation in synaptosomal and neuronal cell culture systems in vitro: structure-activity studies. Journal of Nutritional Biochemistry, 13, 273-281. doi:10.1016/s0955-2863(01)00215-7
• Kızıltaş, H., Ekin, S., Yıldız, D., & Pınar, S. M. (2019). Evaluation of antioxidant properties, trace element and mineral composition of Dactylorhiza umbrosa (Kar. & Kir.) Nevski (Orchidaceae). Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 9(4), 2148-2156. doi:10.21597/jist.532647
• Kim, B., Jung, J. W., Jung, J., Han, Y., Suh, D. H., Kim, H. S., Dhanasekaran, D. N., & Song, Y. S. (2017). PGC1alpha induced by reactive oxygen species contributes to chemoresistance of ovarian cancer cells. Oncotarget, 8, 60299–60311. doi:10.18632/oncotarget.19140
• Kotiloğlu, D., Acet, T., & Özcan, K. (2020). Phytochemical profile and biological activity of a therapeutic orchid from Anatolia: Dactylorhiza romana subsp. georgica. Journal of Food Measurement and Characterization, 14, 3310-3318. doi:10.1007/s11694-020-00566-2
• Kumar, B., Vijayakumar, M., Govindarajan, R., & Pushpangadan, P. (2007). Ethnopharmacological approaches to wound healing–Exploring medicinal plants of India. Journal of Ethnopharmacology, 114, 103-113. doi:10.1016/j.jep.2007.08.010
• Leake, J. R. (2005). Plants parasitic on fungi: Unearthing the fungi in myco-heterotrophs and debunking the ‘saprophytic’ plant myth. Mycologist, 19, 113-122. doi:10.1017/S0269-915X(05)00304-6
• Li, X., Wang, X., Chen, D., & Chen, S. (2011). Antioxidant activity and mechanism of protocatechuic acid in vitro. Functional Foods in Health and Disease, 1(7), 232-244. doi:10.31989/ffhd.v1i7.127
• Lisov, A., Vrublevskaya, V., Lisova, Z., Leontievsky, A., & Morenkov, O. (2015). A 2,5-Dihydroxybenzoic acid–gelatin conjugate: The synthesis, antiviral activity and mechanism of antiviral action against two alphaherpesviruses. Viruses, 7, 5343–5360 doi:10.3390%2Fv7102878
• Louw, C. A. M., Regnier, T. J. C., & Korsten, L. (2002). Medicinal bulbous plants of South Africa and their traditional relevance in the control of infectious diseases. Journal of Ethnopharmacology, 82, 147-154. doi:10.1016/s0378-8741(02)00184-8
• Minh, T. N., Khang, D. T., Tuyen, P. T., Minh, L. M., Anh, L. H., … & Xuan, T.D. (2016). Phenolic compounds and antioxidant activity of Phalaenopsis Orchid Hybrids. Antioxidants, 5(3), 31. doi:10.3390/antiox5030031
• Mishra, A. P., Saklani, S., Salehi, B., Parcha, V., Sharifi-Rad, M., … & Srivastava, M. (2018). Satyrium nepalense, a high altitude medicinal orchid of Indian Himalayan region: chemical profile and biological activities of tuber extracts. Cellular and Molecular Biology (Noisy le Grand), 64(8), 35-43. doi:10.14715/cmb/2018.64.8.6
• Naveed, M., Hejazic, V., Abbas, M., Kamboh, A. A., Khan, G. J., … & XiaoHui, Z. (2018). Chlorogenic acid (CGA): A pharmacological review and call for further research. Biomedicine & Pharmacotherapy, 97, 67-74. doi:10.1016/j.biopha.2017.10.064
• Negahdari, R., Bohlouli, S., Sharifi, S., Dizaj, S. M., Saadat, Y. R., … & Raeesi, S. (2021). Therapeutic benefits of rutin and its nanoformulations. Phytotherapy Research, 35, 1719-1738. doi:10.1002/ptr.6904
• Oğuz, B., Sarı, A. O., & Bilgiç, A. (2005). Ege Bölgesinde Yayılış Gösteren Bazı Salep Orkidelerinin Üretim Olanaklarının Araştırılması. TAGEM Araştırma Projesi. Ege Tarımsal Araştırma Enstitüsü. Menemen, İZMİR.
• Rasouli, H., Farzaei, M. H., & Khodarahmi, R. (2017). Polyphenols and their benefits: A review. International Journal of Food Properties, 20(2), 1700-1741. doi:10.1080/10942912.2017.1354017
• Ren, J., Lu, Y., Qian, Y., Chen, B., Wu, T., & Ji, G. (2019). Recent progress regarding kaempferol for the treatment of various diseases (Review). Experimental and Therapeutic Medicine, 18, 2759-2776. doi:10.3892/etm.2019.7886
• Renz, J., & Taubenheim, G. (1984). Ophrys L. (Orchidaceae). In P. H. Davis (Ed.), Flora of Turkey and the East Aegean Islands vol. 8, (pp. 483-484). Edinburgh, UK: Edinburgh University Press.
• Sağlam, A. (2021). Phytolacca americana L. bitkisinin farklı habitatlardaki bazı ekolojik ve kimyasal parametrelerinin karşılaştırılması. (Yükseklisans tezi), Ordu üniversitesi, Fen Bilimleri Enstitüsü, Türkiye.
• T. C. Orman ve Su İşleri Bakanlığı Orman Genel Müdürlüğü. (2014). Salep Eylem Planı 2014-2018. https://silo.tips/download/tc-orman-ve-su-ler-bakanlii-orman-genel-mdrl-salep Erişim tarihi: 28.11.2023.
• Sezik, E. (1984). Orkidelerimiz, Türkiye’nin Orkideleri. İstanbul, Türkiye: Sandoz Kültür Yayınları, No: 6.
• Sezik, E. (2012). Salep mi? Orkideler mi?. 2. Orkide ve Salep Çalıştayı, İzmir.
• Sharifi‐Rad, J., Hoseini‐Alfatemi, S. M., Sharifi‐Rad, M., & Setzer, W. N. (2015). Chemical composition, antifungal and antibacterial activities of essential oil from Lallemantia royleana (Benth. In Wall.) Benth. Journal of Food Safety, 35(1), 19-25. doi:10.1111/jfs.12139
• Steenkamp, V. (2003). Traditional herbal remedies used by South African women for gynaecological complaints. J. Ethnopharmacol, 86, 97-108. doi:10.1016/S0378-8741(03)00053-9
• Sut, S., Maggi, F., & Dall’Acqua, S. (2017). Bioactive secondary metabolites from Orchids (Orchidaceae). Chemistry & Biodiversity, 14, e1700172. doi:10.1002/cbdv.201700172
• Verma, S., Singh, A., & Mishra, A. (2013). Gallic acid: Molecular rival of cancer. Environmetal toxicology and pharmacology, 35, 473-485. doi:10.1016/j.etap.2013.02.011
• Yi, X., Zuo J., Tan, C., Xian, S., Luo, C., Chen, S., Yu, L., & Luo, Y. (2016). Kaempferol, a flavonoid compound from gynura medica induced apoptosis and growth inhibition in mcf-7 breast cancer cell. African Journal of Traditional, Complementary, and Alternative Medicines, 13, 210-215. doi:10.21010/ajtcam.v13i4.27
• Yong, L., Ranxin, S., Wang, X., & Han-Ming, S. (2008). Luteolin, a flavonoid with potential for cancer prevention and therapy. Current Cancer Drug Targets, 8(7), 634-646. doi:10.2174/156800908786241050
• Zhang, G. N., Bi, Z. M., Wang, Z. T., Xu, L. S., & Xu, G. J. (1994). Advances in studies on chemical constituents from plants of Dendrobium Sw. Chinese Traditional and Herbal Drugs, 0(6), 41-44.