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Sığla yağının sinnamik asit ve alkollerinden elde edilen türevler

Yıl 2020, Cilt: 8 Sayı: 3, 285 - 294, 02.10.2020
https://doi.org/10.31195/ejejfs.793765

Öz

Sığla ağacı (Liquidambar orientalis Miller) Türkiye’de yetişen endemik bir ağaç türüdür. Muğla bölgesinde (Köyceğiz, Fethiye) yetişen ağaç dünyada 4 türe sahiptir. Sığla ağacı görünüş olarak çınara benzer fakat yaprakları çınar yaprağından daha küçüktür. Ağaçlar uzun ömürlü (200-300 yıl) ve 25-30 metre uzunluğa sahiptirler. Ağacın çoğalması, tohum, kök ve kütük sürgünlerden olur. Ormanların kesilmesi ve aşırı üretim gibi sebeplerden günümüzde sığla ormanlarının miktarı çok düşmüştür. Sığla yağı ağacın gövdesi kazınarak elde edilir. Bir zamanlar önemli bir ihraç maddesi olan sığla yağı günümüzde bu önemini kaybetmiştir. Kahverengimsi sarı renkte olup yarı sıvıdır. Acı bir tada ve sinnamik aside benzer bir kokuya sahiptir. % 35-40 civarındaki sinnamik asidi serbest ve ester halinde bulundurur. %1 civarında uçucu yağa sahip olan sığla yağı aynı zamanda % 60 civarında sitoresin denilen triterpen asidleri de içerir.
Çalışmamızda sığla yağı, Muğla Orman Bölge Müdürlüğü, Köyceğiz Orman İşletmesinden sağlandı. Yağ içinde bulunan sinnamik asit esterleri alkollü KOH çözeltisi ile hidroliz edildi. Hidroliz sonucu esterler, potasyum sinnamat ve alkollere dönüştürüldü. Potasyum sinnamat asitlendirilerek sinnamik aside sonra metil alkol ve etil alkolle tiyonil klorür varlığında esterlerine çevrildi. Alkoller, asetil klorür ile reaksiyona sokularak asetat türevlerine dönüştürüldü. Bu oluşan esterler, 1H NMR ve IR ve GC/MS gibi değişik teknikler ile karakterize edildi.

Kaynakça

  • Andrikopoulos, N.K., Kaliora, A.C., Assimopoulou, A.N., Papapeorgiou, V.P. (2003). Biological Activity of Some Naturally Occurring Resins, Gums and Pigments Against In Vitro LDL Oxidation. Phytotherapy Research 17: 501–507.
  • Berkel, A., Huş, S. (1945). Sığala Ağacı Ormanları ve Sığala Yağı Üzerine Araştırmalar. Ankara Yüksek Ziraat Enstitüsü Dergisi 3(1):5-10.
  • Charehsaz, M., Reis, R., Helvacıoğlu, S., Sipahi, H., Güzelmeriç, E., Acar, E.T.,, Çiçek, G., Yeşilada, E., Aydın, A. (2016). Safety evaluation of styrax liquidus from the viewpoint of genotoxicity and mutagenicity. Journal of Ethnopharmacology 194:506–512.
  • Fernandez, X., Lizzani-Cuvelier, L., Loiseau, A.M., Perichet, C., Delbecque, C., Arnaudo, J.F. (2005). Chemical composition of the essential oils from Turkish and Honduras Styrax. Flavour And Fragrance Journal 20:70–73.
  • Guo, J., Duan, J., Tang, Y., Li, Y. (2011). Sedative and anticonvulsant activities of styrax after oral and intranasal administration in mice. Pharmaceutical Biology 49(10):1034–1038.
  • Gürbüz, İ., Yeşilada, E., Demirci, B., Sezik, E., Demirci, F., Başer, K.H.C. (2013). Characterization of volatiles and anti-ulcerogenic effect of Turkish sweetgum balsam (Styraxliquidus). Journal of Ethnopharmacology 148:332–336.
  • Hafızoglu, H., Reunanen, M., İstek, A. (1996). Chemical Constituents of Balsam from Liquidambar orientalis. Holzforschung 50:116-117.
  • Honda, G., Yeşilada, E., Tabata, M., Sezik, E., Fujita, T., Takeda, Y., Takaishi, Y., Tanaka. (1996). Traditional medicine in Turkey VI. Folk medicine in West Anatolia: Afyon, Kütahya, Denizli, Muğla, Aydın provinces. Journal of Ethnopharmacology 53:75-87.
  • Hovaneissian, M., Archier, P., Mathe, C., Culioli, G., Vieillescazes, C. (2008). Analytical investigation of styrax and benzoin balsams by HPLC- PAD-fluorimetry and GC-MS. Phytochemical Analysis 19:301–310.
  • Hu, L.H., Zou, H.B., Gong, J.X., Li, H.B., Yang, L.X., Cheng, W., Zhou, C.X., Bai, H., Gue´ritte, F., Zhao, Y. (2005). Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues, Journal of Natural Products 68:342-348.
  • Huneck, S. (1963). Triterpene-IV: Die Triterpensauren des Balsams von Liquidambar orientalis Miller. Tetrahedron 19(3):479-482.
  • İstek, A. (1994). Sığla yağı (Storax)’nın Kimyasal Bileşenleri. [Yüksek Lisans] Karadeniz Teknik Üniversitesi Fen Bilimleri Enstitüsü, Trabzon, TÜRKİYE.
  • Jain, R.K., Piskorz, C.F., Huang, B.G., Locke, R.D., Han, H.L., Koenig, A., Varki, A., Matta, K.L. (1998). Inhibition of L- and P-selectin by a rationally synthesized novel core 2-like branched structure containing GalNAc-Lewisx and Neu5Aca2–3Galb1–3GalNAc sequences. Glycobiology 8(7):707-717.
  • Karadeniz, B., Ülker, Z., Alpsoy, L. (2011). Genotoxic and cytotoxic effects of storax in vitro. Toxicology and Industrial Health 29(2):181–186.
  • Kim, J., Seo, S.M., Lee, S.G., Shin, S.C., Park, I.K. (2008). Nematicidal Activity of Plant Essential Oils andComponents from Coriander (Coriandrum sativum), Oriental Sweetgum (Liquidambar orientalis), and Valerian (Valeriana wallichii) Essential Oils against Pine Wood Nematode (Bursaphelenchus xylophilus). Journal of Agricultural and Food Chemistry 56:7316–7320.
  • Lee, Y.S., Kim, J., Lee, S.G., Oh, E., Shin, S.C., Park, I.K. (2009). Effects of plant essential oils and components from Oriental sweetgum (Liquidambar orientalis) on growth and morphogenesis of three phytopathogenic fungi. Pesticide Biochemistry and Physiology 93:138–143.
  • Nunez, M.T., Martin, V.S. (1990). Efficient Oxidation of Phenyl Groups to Carboxylic Acids with Ruthenium Tetraoxide. A Simple Synthesis of (R )-7-Caprolactone, the Pheromone of Trogoderma granarium. Journal of Organic Chemistry 55:1928-1932.
  • Onaran, A., Bayan, Y. (2016). Antifungal Activity of Liquidambar Orientalis L., and Myrtus Communis L. Against Some Plant Pathogenic Fungi. Scientific Papers. Series A. Agronomy 59:360-364.
  • Öçsel, H., Teke, Z., Sacar, M., Kabay, B., Düzcan, S.E., Kara, İ.G. (2012). Effects of Oriental Sweet Gum Storax on Porcine Wound Healing. Journal of Investigative Surgery 25:262–270.
  • Öztürk, M., Çelik, A., Güvensen, A., Hamzaoğlu, E. (2008). Ecology of tertiary relict endemic Liquidambar orientalis Mill. forests. Forest Ecology and Management 256:510–518.
  • Sağdıç, O., Özkan, G., Özcan, M., Özçelik, S. (2005). A Study on Inhibitory Effects of Sığla Tree (Liquidambar orientalis Mill. var. orientalis) Storax Against Several Bacteria. Phytotherapy Research 19:549–551.
  • Schulz, M.J., Wang, Y., Ghergurovich, J.M. (2010). Prolyl hydoxylase inhibitors, Patent WO 2010/059555
  • Tanker, M., Sayron, E. (1974). Styrax Liquidus Üzerinde Farmakognozik Araştırmalar. Ankara Eczacılık Fakültesi Mecmuası 4:108-148.
  • Topal, Ü., Sasaki, M., Goto, M., Otles, S. (2008). Chemical compositions and antioxidant properties of essential oils from nine species of Turkish plants obtained by supercritical carbon dioxide extraction and steam distillation. International Journal of Food Sciences and Nutrition 59(7-8):619-634.
  • Ürker, O. (2014). Çevre Etiği Bağlamında Anadolu Sığla Ormanları. [Doktora tezi] Ankara Üniversitesi Sosyal Bilimler Enstitüsü, Ankara, TÜRKİYE.
  • Wang, F., Hua, H., Pei, Y., Chen, D., Jing, Y. (2006). Triterpenoids from the Resin of Styrax tonkinensis and Their Antiproliferative and Differentiation Effects in Human Leukemia HL-60 Cells. Journal of Natural Products 69:807-810.

The obtained derivatives from cinnamic acid and alcohols of Turkish sweetgum balsam

Yıl 2020, Cilt: 8 Sayı: 3, 285 - 294, 02.10.2020
https://doi.org/10.31195/ejejfs.793765

Öz

Sweetgum tree (Liquidambar orientalis Miller) is an endemic tree species grown in Turkey. The tree grown in Muğla region (Köyceğiz, Fethiye) has 4 species in the world. The sweetgum tree is similar in appearance to the plane tree but its leaves are smaller than the sycamore leaf. Trees are long lasting (200-300 years) and have a length of 25-30 meters. The multiplication of the trees is from seed, root and billet shoots. Due to the reasons such as cutting of forests and excessive production, the amount of sweetgum tree forests has declined. Turkish sweetgum balsam is obtained by injuring the tree trunk. Turkish sweetgum balsam, which was once an important export item, lost its importance today. It is brownish yellow and semi-liquid. It has a bitter taste and a similar smell to cinnamic acid. It contains about 35-40% cinnamic acid free and ester. Turkish sweetgum balsam, which has an essential oil of about 1%, also contains about 60% of the triterpene acids called storesin.
In our study, Turkish sweetgum balsam was provided from Köyceğiz Forestry Administration, Muğla Forest Regional Directorate. Cinnamic acid esters found in balsam were hydrolyzed with alcoholic KOH solution. By hydrolysis, esters were converted into potassium cinnamates and alcohols. Potassium cinnamate was acidified to cinnamic acid then converted to esters in the presence of thionyl chloride with methyl alcohol and ethyl alcohol. The alcohols were converted to the acetate derivatives by reacting with acetyl chloride. These formed esters were characterized by various techniques such as 1H NMR, IR and GC/MS.

Kaynakça

  • Andrikopoulos, N.K., Kaliora, A.C., Assimopoulou, A.N., Papapeorgiou, V.P. (2003). Biological Activity of Some Naturally Occurring Resins, Gums and Pigments Against In Vitro LDL Oxidation. Phytotherapy Research 17: 501–507.
  • Berkel, A., Huş, S. (1945). Sığala Ağacı Ormanları ve Sığala Yağı Üzerine Araştırmalar. Ankara Yüksek Ziraat Enstitüsü Dergisi 3(1):5-10.
  • Charehsaz, M., Reis, R., Helvacıoğlu, S., Sipahi, H., Güzelmeriç, E., Acar, E.T.,, Çiçek, G., Yeşilada, E., Aydın, A. (2016). Safety evaluation of styrax liquidus from the viewpoint of genotoxicity and mutagenicity. Journal of Ethnopharmacology 194:506–512.
  • Fernandez, X., Lizzani-Cuvelier, L., Loiseau, A.M., Perichet, C., Delbecque, C., Arnaudo, J.F. (2005). Chemical composition of the essential oils from Turkish and Honduras Styrax. Flavour And Fragrance Journal 20:70–73.
  • Guo, J., Duan, J., Tang, Y., Li, Y. (2011). Sedative and anticonvulsant activities of styrax after oral and intranasal administration in mice. Pharmaceutical Biology 49(10):1034–1038.
  • Gürbüz, İ., Yeşilada, E., Demirci, B., Sezik, E., Demirci, F., Başer, K.H.C. (2013). Characterization of volatiles and anti-ulcerogenic effect of Turkish sweetgum balsam (Styraxliquidus). Journal of Ethnopharmacology 148:332–336.
  • Hafızoglu, H., Reunanen, M., İstek, A. (1996). Chemical Constituents of Balsam from Liquidambar orientalis. Holzforschung 50:116-117.
  • Honda, G., Yeşilada, E., Tabata, M., Sezik, E., Fujita, T., Takeda, Y., Takaishi, Y., Tanaka. (1996). Traditional medicine in Turkey VI. Folk medicine in West Anatolia: Afyon, Kütahya, Denizli, Muğla, Aydın provinces. Journal of Ethnopharmacology 53:75-87.
  • Hovaneissian, M., Archier, P., Mathe, C., Culioli, G., Vieillescazes, C. (2008). Analytical investigation of styrax and benzoin balsams by HPLC- PAD-fluorimetry and GC-MS. Phytochemical Analysis 19:301–310.
  • Hu, L.H., Zou, H.B., Gong, J.X., Li, H.B., Yang, L.X., Cheng, W., Zhou, C.X., Bai, H., Gue´ritte, F., Zhao, Y. (2005). Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues, Journal of Natural Products 68:342-348.
  • Huneck, S. (1963). Triterpene-IV: Die Triterpensauren des Balsams von Liquidambar orientalis Miller. Tetrahedron 19(3):479-482.
  • İstek, A. (1994). Sığla yağı (Storax)’nın Kimyasal Bileşenleri. [Yüksek Lisans] Karadeniz Teknik Üniversitesi Fen Bilimleri Enstitüsü, Trabzon, TÜRKİYE.
  • Jain, R.K., Piskorz, C.F., Huang, B.G., Locke, R.D., Han, H.L., Koenig, A., Varki, A., Matta, K.L. (1998). Inhibition of L- and P-selectin by a rationally synthesized novel core 2-like branched structure containing GalNAc-Lewisx and Neu5Aca2–3Galb1–3GalNAc sequences. Glycobiology 8(7):707-717.
  • Karadeniz, B., Ülker, Z., Alpsoy, L. (2011). Genotoxic and cytotoxic effects of storax in vitro. Toxicology and Industrial Health 29(2):181–186.
  • Kim, J., Seo, S.M., Lee, S.G., Shin, S.C., Park, I.K. (2008). Nematicidal Activity of Plant Essential Oils andComponents from Coriander (Coriandrum sativum), Oriental Sweetgum (Liquidambar orientalis), and Valerian (Valeriana wallichii) Essential Oils against Pine Wood Nematode (Bursaphelenchus xylophilus). Journal of Agricultural and Food Chemistry 56:7316–7320.
  • Lee, Y.S., Kim, J., Lee, S.G., Oh, E., Shin, S.C., Park, I.K. (2009). Effects of plant essential oils and components from Oriental sweetgum (Liquidambar orientalis) on growth and morphogenesis of three phytopathogenic fungi. Pesticide Biochemistry and Physiology 93:138–143.
  • Nunez, M.T., Martin, V.S. (1990). Efficient Oxidation of Phenyl Groups to Carboxylic Acids with Ruthenium Tetraoxide. A Simple Synthesis of (R )-7-Caprolactone, the Pheromone of Trogoderma granarium. Journal of Organic Chemistry 55:1928-1932.
  • Onaran, A., Bayan, Y. (2016). Antifungal Activity of Liquidambar Orientalis L., and Myrtus Communis L. Against Some Plant Pathogenic Fungi. Scientific Papers. Series A. Agronomy 59:360-364.
  • Öçsel, H., Teke, Z., Sacar, M., Kabay, B., Düzcan, S.E., Kara, İ.G. (2012). Effects of Oriental Sweet Gum Storax on Porcine Wound Healing. Journal of Investigative Surgery 25:262–270.
  • Öztürk, M., Çelik, A., Güvensen, A., Hamzaoğlu, E. (2008). Ecology of tertiary relict endemic Liquidambar orientalis Mill. forests. Forest Ecology and Management 256:510–518.
  • Sağdıç, O., Özkan, G., Özcan, M., Özçelik, S. (2005). A Study on Inhibitory Effects of Sığla Tree (Liquidambar orientalis Mill. var. orientalis) Storax Against Several Bacteria. Phytotherapy Research 19:549–551.
  • Schulz, M.J., Wang, Y., Ghergurovich, J.M. (2010). Prolyl hydoxylase inhibitors, Patent WO 2010/059555
  • Tanker, M., Sayron, E. (1974). Styrax Liquidus Üzerinde Farmakognozik Araştırmalar. Ankara Eczacılık Fakültesi Mecmuası 4:108-148.
  • Topal, Ü., Sasaki, M., Goto, M., Otles, S. (2008). Chemical compositions and antioxidant properties of essential oils from nine species of Turkish plants obtained by supercritical carbon dioxide extraction and steam distillation. International Journal of Food Sciences and Nutrition 59(7-8):619-634.
  • Ürker, O. (2014). Çevre Etiği Bağlamında Anadolu Sığla Ormanları. [Doktora tezi] Ankara Üniversitesi Sosyal Bilimler Enstitüsü, Ankara, TÜRKİYE.
  • Wang, F., Hua, H., Pei, Y., Chen, D., Jing, Y. (2006). Triterpenoids from the Resin of Styrax tonkinensis and Their Antiproliferative and Differentiation Effects in Human Leukemia HL-60 Cells. Journal of Natural Products 69:807-810.
Toplam 26 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Orman Endüstri Mühendisliği
Bölüm Articles
Yazarlar

Nilay Teker 0000-0002-0540-7497

Hakan Kolancılar 0000-0002-2901-0064

Yayımlanma Tarihi 2 Ekim 2020
Gönderilme Tarihi 11 Eylül 2020
Yayımlandığı Sayı Yıl 2020 Cilt: 8 Sayı: 3

Kaynak Göster

APA Teker, N., & Kolancılar, H. (2020). Sığla yağının sinnamik asit ve alkollerinden elde edilen türevler. Eurasian Journal of Forest Science, 8(3), 285-294. https://doi.org/10.31195/ejejfs.793765

 

E-posta: hbarist@gmail.com 

 

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