Secondary Metabolites

Yıl 2021, Cilt: 35 Sayı: 1, 203 - 215, 01.06.2021

Gülsevim Tiring , Serdar Satar , Okan Özkaya

Öz

Secondary metabolites are organic compounds produced by microorganism or plant which are not
directly involved in the growth, development, or reproduction of the organism. Secondary metabolites play an important role in plant defense against insects and microorganisms defenses. Humans use to secondary
metabolites in medicines, flavorings, pigments, and perfumes. Also, the recent studies can conclude that
secondary metabolites may be considered as effective COVID-19 antiprotease drugs. Plant secondary
metabolites can be divided into three major classes as terpenes, phenolics and alkaloids. Classification of terpene is based on the number of isoprene units present in their structure. Phenolic compounds are structures bearing one or more hydroxyl groups on an aromatic ring structure. These compounds are classified according to number of carbon. Alkaloids are a diverse group of nitrogen-containing compounds.

Anahtar Kelimeler

Natural Plant Products, Terpenes, Alkaloids, Phenolic Compounds

Sekonder Metabolitler

Öz

Sekonder metabolitler, organizmanın büyümesinde, gelişiminde ve çoğalmasında doğrudan yer almayan,
mikroorganizmalar veya bitkiler tarafından üretilen organik bileşiklerdir. Sekonder metabolitler, böceklerin ve
mikroorganizmaların korunmasına karşı bitki savunmasında önemli bir rol oynamaktadır. İnsanlar ilaçlarda,
aromalarda, pigmentlerde ve parfümlerde sekonder metabolitleri kullanmaktadırlar. Ayrıca, son çalışmalar ile sekonder metabolitlerin COVID-19 antiproteaz ilaçları arasında etkili olarak kabul edilebileceği sonucuna da varılmıştır. Bitki sekonder metabolitleri terpenler, fenolikler ve alkaloitler olarak üç ana sınıfa ayrılmaktadır.
Terpen sınıflandırması, yapılarında bulunan izopren birimlerinin sayısına dayanmaktadır. Fenolik bileşikler ise
bir aromatik halka yapısı üzerinde bir veya daha fazla hidroksil grubu taşıyan yapılardır. Bu bileşiklerde karbon sayısına göre sınıflandırılmaktadır. Alkaloitler, bazik bileşikler içeren çeşitli bir azot grubudur.

Anahtar Kelimeler

Doğal Bitki Ürünleri, Terpenler, Alkaloitler, Fenolik Bileşikler

Kaynakça

• Adem, S., Eyupoglu, V., Sarfraz, I., Rasul, A. and Ali, M. 2020. Identification of potent COVID-19 main protease (Mpro) inhibitors from natural polyphenols: An in silico strategy unveils a hope against CORONA.
• Aniszewski, T. 2007. Alkaloids-secrets of life alkaloid chemistry, biological significance, applications and ecological role. Elsevier, Amsterdam, pp 1–316.
• Bal, E. 2012. Hasat sonrası putresin ve salisilik asit uygulamalarının kirazın soğukta muhafazası üzerine etkisi. SDÜ Ziraat Fakültesi Dergisi,7(2), 23-31.
• Boiteau, P., Pasich, B. And Ratsımamanga, R(Les). 1969. Triterpenoides. Gauthier-Villars Paris, p 3-5.
• Brooker, N., Winderski, J. and Blumi, E. 2008.Halogenated Coumarins Derivatives as Novel Seed Protectants.Communication in Agriculture and Applied Biological Sciences, 73(2): 81-89.
• Caldwell, M.M., Robberecht, R. and Flint, S.D. 1983. Internol filters: Prospects for UVacclimation in higher plants. Physiol. Plant 58: 445-450.
• Connolly, J.D. and Hill, R.A. 1991. Dictionary of Terpenoids. (London: Chapman and Hall). Cordell, G. A. (1976). Biosynthesis of sesquiterpenes. Chemical Reviews, 76(4), 425-460.
• Croteau, R., Kutchan, T.M. and Lewis, N.G. 2000. Natural products (secondary metabolites). Biochemistry and molecular biology of plants,24, 1250-1319.
• Dawson, F.A. 1994. The amazing terpenes. Naval Stores Rev. MarchlAprll, 6-12.
• Dewick, P.M. 2002. Medicinal natural products. A biosynthetic approach, 2nd edn. Wiley, New York, p 381.
• Diyoke, O.I. 2014. Antıoxıdant and toxıcologıc propertıes of methanol leaf extract of stephanıa dınklageı ın wıstar albıno rats.
• Fraenkel, G. 1959. The raison d'etre of secondary substances. Science 129: 1466-1470.
• Fox, E.G., Wu, X., Wang, L., Chen, L., Lu, Y.Y. and Xu, Y. 2019. Queen venom isosolenopsin A delivers rapid incapacitation of fire ant competitors. Toxicon,158, 77-83.
• Ebel, J. and Grisebach, H. 1988. Defense strategies of soybean against the fungus Phytophthora megasperma f. sp. glycinea: A molecular analysis. Trends Biochem. Sci. 13: 23-27.
• Gill, S.S. and Tuteja, N. 2010. Polyamines and abiotic stress tolerance in plants.Plant signaling & behavior,5(1), 26-33.
• Gournelis, D.C., Laskaris, G.G. and Verpoorte, R. 1997. Cyclopeptide alkaloids.Natural product reports,14(1), 75- 82.
• Harborne, J.B. 1986, Recent advances in chemical ecology. Nat Prod Rep 3:323-344.
• Harborne, J.B. 1988. Introduction to ecological biochemistry (3rded.). London: Academic Press.
• Harborne, J.B., Simmonds, N.W. (1964). In Biochemistry of Phenolic Compounds, p.79 [J. B. Harborne, editor]. London: Academic Press.
• Karakaya, S. 2004. Bioavailability of phenolic compounds. Critical Reviews in Food Science and Nutrition, 44(6), 453-464.
• Khaerunnisa, S., Kurniawan, H., Awaluddin, R., Suhartati, S. and Soetjipto, S. 2020. Potential Inhibitor of COVID-19 Main Protease (Mpro) From Several Medicinal Plant Compounds by Molecular Docking Study. Prepr. Doi 10.20944/preprints202003. 0226. v1, 1-14. Khalil, A. 2017. Role of Biotechnology in Alkaloids Production. In Catharanthus roseus (pp. 59-70). Springer, Cham.
• Khosroshahi, M.R.Z., Esna-Ashari, M. and Ershadi, A. 2007. Effect of Exogenous Putrescine on Postharvest Life of Strawberry (Fragaria ananassa Duch.) Fruit, Cultivar Selva. Scientia Horticulturae. 114:27-32.
• Langenheim, J.H. 1994. Higher plant terpenoids: a phytocentric overview of their ecological roles. Journal of Chemical Ecology, 20(6), 1223-1280.
• Levin, D.A. 1976). The chemical defenses of plants to pathogens and herbivores. Ann Rev Ecol Syst 7:121-159.
• Levinson, H.Z. 1976. The defensive role of alkaloids in insects and plants. Experientia 32:408-411.
• Liu, J., Honda, C and Moriguchi, T. 2006. Involvement of Polyamine in Floral and Fruit Development. JARQ. 40(1),51-58.
• Ludwiczuk, A., Skalicka-Woźniak, K. and Georgiev, M.I. 2017. Terpenoids. In Pharmacognosy (pp. 233-266). Academic Press.
• Martinez-Romero, D., Serrano, M., Carbonell, A., Burgos, L., Riquelme, F. and Valero, D. 2002. Effects of Postharvest Putrescine Treatment on Extending Shelf Life and Reducing Mechanical Damage in Apricot. J. Food Sci. 67: 1706-1712.
• Mazza, G. and Miniati, E. 1993. Anthocyanins in Fruits, Vegetables and Grains. CRC Press, London. McCrea, K.D., Levy, M. (1983). Photographic visualization of floral colors as perceived by honeybee pollinators. Am. J. Bot. 70: 369-375.
• Mohammadi, N. and Shaghaghi, N. 2020. Inhibitory effect of eight Secondary Metabolites from conventional Medicinal Plants on COVID_19 Virus Protease by Molecular Docking Analysis.
• Moridi Farimani, M., Nejad Ebrahimi, S., Salehi, P., Bahadori, M.B., Sonboli, A., Khavasi, H.R. and Hamburger, M. 2013. Antitrypanosomal triterpenoid with an ε-lactone E-ring from Salvia urmiensis. Journal of Natural Products, 76(9), 1806-1809.
• Mothes, K. 1955. Physiology of alkaloids. Annu Rev Plant Physiol 6: 393-432. Murray, R.D.H., Mendez, J. and Brown, S.A. 1982. Coumarin activity in plants and bioorganism aspects. John Wiley; 2: 45-55.
• Naumann, C., Hartmann, T. and Ober, D. 2002. Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae. Proceedings of the National Academy of Sciences, 99(9), 6085-6090.
• Oates, J.F., Waterman, P.G. and Choo, G.M. 1980. Food selection by the South Indian leaf- monkey, Presbytis johnii, in relation to leaf chemistry, Oecologia 45, 45-56.
• Özeker, E. 1999. Phenolic compounds and their importance. Anadolu Ege Tarımsal Araştırma Enstitüsü Dergisi, 9(2).
• Özkaya, O., Şen, K., Aubert, C., Dündar, Ö. and Gunata, Z. 2018. Characterization of the free and glycosidically bound aroma potential of two important tomato cultivars grown in Turkey. Journal of Food Science and Technology, 55(11), 4440-4449.
• Özkaya, O., Yabaci Karaoglan, S., Incesu, M. and Yesiloglu, T. 2019. The general and volatile properties and the quality of two newly selected Satsuma clones (11/1 Izmir and 30/Izmir) grown under Mediterranean ecological conditions, Food Science and Technology, 39(2),451-457.
• Paech K. 1950. Biochemie und Physiologie der sekundären Pflanzenstoffe. Springer, Berlin Heidelberg. Plemenkov, V.V. 2001. Introduction to Chemistry of Natural Compounds. Kazan, Russia.
• Ramakrishna, A. and Ravishankar, G.A. 2011. Influence of abiotic stress signals on secondary metabolites in plants. Plant Signal. Behav. 6, 1720–1731.
• Raskin, J. 1992. Protein–polyphenol interactions: nutritional aspects, in Proc. 16th Int. Conf. Groupe Polyphenols, 16, Part II, 11–18.
• Rice, E.L. 1987. Allelopathy: An overwiew. In: Waller, G.R. (Ed.) Allelochemicals: Role in agriculture and forestry. ACS Symposium Series No. 330, American Chemical Society, Washington, D. C.
• Rolfe, B.G. and Gresshoff, P.M. 1988. Genetic analysis of legume nodule initiation. Annu. Rev. Plant Physiol. Plant Mol. Biol. 39: 297-319.
• Rosenthal, G.A. and Janzen, D.H. 1979. Herbivores: their interaction with secondary plant metabolites. Academic Press, London New York.
• Schildknecht, H. 1977. Protective substances of arthropods and plants. Pontif Accad Sci 3: 59-107.
• Schuster, B. and Herrmann, K. 1985. Hydroxybenzoic and hydroxycinnamic acid derivatives in soft fruits. Phytochemistry, 24, 2761–2764.
• Seigler, D.S. 1998. Plant Secondary Metabolism. Springer, US.
• Shahidi, F. and Naczk, M. 1995. Methods of analysis and quantification of phenolic compounds. Food phenolic: Sources, chemistry, effects and applications, 287-293.
• Shahidi, F. and Naczk, M. 2003. Phenolics in food and nutraceuticals. CRC press.
• Stahl, E. 1888. Pflanzen und Schnecken. Jena Z Naturwiss 22,557.
• Tiring, G., Satar, S. and Özkaya, O. 2020. Use of Monoterpenes in the Control of Bark Beetles (Coleoptera: Curculionidae, Scolytinae) in Forest Areas. Turkish Journal of Agriculture-Food Science and Technology, 8(7), 1522-1527.
• Vermerris, W. and Nicholson, R. 2007. Phenolic compound biochemistry. Springer Science & Business Media.
• Zheng, Y. and Zhang, Q. 2004. Effects of Polyamines and Salicylic Acid on Postharvest Storage of. 'Ponkan' Mandarin. Acta Horticulturae. 632,317-320.
• Zinkel, D.F. and Russell, J. 1989. Naval Stores: Production, Chemistry, Utilization. (New York: Pulp Chemicals Association).