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C-Glikozitlere Genel Bakış

Year 2010, Volume 6, Issue 1, 33 - 44, 01.03.2010

Abstract

-

References

  • Levy, D. E., Tang, C., The Chemistry of CGlycoside, Pergamon, USA (1995).
  • Du, Y., Linhardt, R. J., Vlahov, I. R., Recent Advances in Stereoselective C-glycoside Synthesis, Tetrahedron, 54 (33): 9913-9959 (1998).
  • Tomiyama, H., Kobayashi, Y., Atsushi, N., Tomiyama, A., Tomiyama, N., C-Glycosides and Preparation of Thereof as Antidiabetic Agents, United States Patent No. US 6,627,611 B2 (2003).
  • Gervay, J., Flaherty, T. M., Holmes, D., Studies on the Synthesis of C-glycoside Sulfones as Potential Glycosyl Transferase Inhibitors, Tetrahedron, 53 (48): 16355-16364 (1997).
  • Wellington, K. W., Benner, S. A., A Review: Synthesis of Aryl C-glycosides Via the Heck Coupling Reaction, Nucleosides, Nucleotides, and Nucleic Acids, 25 (12):1309-1333 (2006).
  • Hacksell, U., Daves, G. D. Jr., Edt: Ellis, G.P., West, G. B., The chemistry and biochemistry of C-nucleosides and C-arylglycosides, Progress in Medicinal Chemistry, 22: 1-65 (1985).
  • Darnall, K. R., Townsend, L. B., Robins, R. K., The Structure of Showdomycin, a Novel Carbon-Linked Nucleoside Antibiotic Related to Uridine, Proceedings of the National Academy of Sciences of the United States of America, 57: 548553 (1967).
  • Salem, P. A., Bodey, G. P., Burgess, M. A., Murphy, W. K., Freireich, E. J., A Phase I Study of Pyrazofurin. Cancer (Phila.), 40: 2806-2809 (1977).
  • Westhead, J. E., Price, H. D., Quantitative Assay of Pyrazofurin a New Antiviral, Antitumor, Antibiotic, Antimicrobial Agent and Chemotherapy, 5 (1): 90-91 (1974).
  • Bernardo, S. D., Weigele, M., C-nucleoside antibiotics. 2. Synthesis of Oxazinomycin (minimycin), Journal of Organic Chemistry, 42 (1):109-112 (1977).
  • Cai, D. M., Li M. J., Li, D. L., Synthesis of C-Nucleoside Analogues: 2-[2-(hydroxymethyl)-1,3-dioxolan-5-yl]1,3-thiazole-4-carboxamide and 2-[2-(mercaptometh-yl)-1,3-dioxolan-5-yl]1,3-thiazole-4-carboxamide, Chinese Chemical Letters, 15 (2): 163-166 (2004).
  • Tricot, G., Jayaram, H. N., Weber, G., Hoffman, R., Tiazofurin - Biological Effects and Clinical Uses, International Journal of Cell Cloning, 8 (3): 161-170 (1990).
  • Ramasamy, K. S., Averett, D., A Modified Synthesis of Tiazofurin, Nucleosides & Nucleotides, 18 (11-12): 2425-2431 (1999).
  • Tatar, A., Özkurt, Z., Kiki, İ., Genotoxic Effect of Ribavirin in Patients with CrimeanCongo Hemorrhagic Fever, Japanese Journal of Infectious Diseases, 58 (5): 313-315 (2005).
  • Uchananal, J. G., Stobie, A., Wightman, R., C-Nucleoside Studies. Part XI. Cine-substitution in 1,4-Dinitropyrazoles; Application to the Synthesis of Formycin via Nitropyrazole Derivatives, Canadian Journal of Chemistry, 58 (23):26242627 (1980).
  • Okuda, S., Herbicides. In The Search for Bioactive Compounds from Microorganisms; Omura, S., Ed.; Springer-Verlag: New York, 224-236 (1992).
  • Sağıroglu, A., Özcan, H. M., Bitki Ekstraktlarındaki Flavonoid Aglikonlarının Tayini, 21. Ulusal Kimya Kongresi, İnönü Üniversitesi, Malatya (2007).
  • Granados, E. H., Maldonado, L., A Wacker–Cook Synthesis of Isoflavones: Formononetine, Tetrahedron Letters, 50 (14): 1542-1545 (2009).
  • Delazar, A., Kosarı, A. R., Nazemiyeh, H., Modaresi, M., Gibbons, S., Nahar L., Sarker, S. D., Flavone C-Glycosides and Cucurbitacin Glycosides from Citrullus colocynthis, DARU, 14 (3):109-114 (2006).
  • Grotewold, E., The Science of Flavonoids, Springer, USA (2006).
  • Kim, Y., Jun, M., Jeong, W., Chung, S., Antioxidant Properties of Flavone C-glycosides from Atractylodes Japonica Leaves in Human Low-density Lipoprotein Oxidation, Journal of Food Science, 70 (9): S575-580 (2005).
  • Morsch, M., Girardi, L. G. J., Cechinel-Filho W., Meyre-Silva C., Rodrigues C. A., Separation of C-glycoside Flavonoids from Aleurites moluccana Using Chitin and Full N-Acetylated Chitin, Verlag der Zeitschrift für Naturforschung, 57c: 957-959 (2002).
  • Mishra, B. B., Yadav, S. B., Rakesh, K. S., Tripathi, V., A Novel Flavonoid C-Glycoside from Sphaeranthus indicus L. (Family Compositae), Molecules, 12 (10): 2288-2291 (2007).
  • Yaylı, N., Seyman, H., Baltacı, C., Flavone C-Glycosides from Scleranthus uncinatus, Phytochemistry, 58 (4): 607-610 (2001).
  • Leong, C. N. A, Takao, M., Hanashiro, I., Tamaki, H., Antioxidant Flavonoid Glycosides from the Leaves of Ficus pumila L., Food Chemistry, 109 (2): 415-420 (2008).
  • Martin, F. S., Unified Strategy for the Synthesis of C-Aryl Glycosides, Pure Applied Chemistry, 75 (1): 63-70 (2003).
  • The Merck Index, 11 th Edition, 1850.
  • Allevi, P., Anastasia, M., Ciuffreda, P., Fiecchi, A., Scala, A., Bingham, S., Muir, M., Tyman, J., The First Total Synthesis of Carminic Acid, Journal of the Chemical Society-Chemical Communications, 18: 1319-1320 (1991).
  • Balitz, D. M., O’Herron, F. A., Bush, J., Vyas, D. M., Nettleton, D. E., Grulich, R. E., Bradner, W. T., Doyle, T. W., Arnold, E., Clardy, J., Antitumor Agents from Streptomyces Anandii: Gilvocarcins V, M and E., The Journal of Antibiotics, 34 (12): 1544-1555 (1981).
  • Koyama, Y., Yamaguchi, R., and Suzuki, K., Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin, Angewandte Chemie, 120 (6): 1100-1103 (2008).
  • Kimura, Y., Sumiyoshi, M., Taniguchi, M., Baba, K., Antitumor and Antimetastatic Actions of Anthrone C-Glycoside, Cassialoin Isolated from Cassia garrettiana Heartwood in Colon 26-bearing mice, Japanese Cancer Association, 99 (11): 2336-2348 (2008).
  • Tewtrakul, S., Subhadhirasakul, S., Rattanasuwan, P., HIV-1 Protease Inhibitory Effects of Some Selected Plants in Caesalpiniaceae and Papilionaceae Families, Songklanakarin Journal of Science and Technology, 25 (4): 509-514 (2003).
  • Krenn, L., Pradhan, R., Presser, A., Reznicek, G., Anthrone C-Glycosides from Rheum emodi, Chemical and Pharmaceutical Bulletin 52 (4): 391-393 (2004).
  • Diaz, F., Chai, H-B., Mi, Q., Su, B., Schunke Vigo, J., Graham, J. G., Cabieses, F., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Swanson, S. M., Kinghorn, A. D., Anthrone and Oxanthrone CGlycosides from Picramnia latifolia Collected in Peru, Journal of Natural Products, 67 (3):352–356 (2004).
  • The Merck Index, 12 th Edition, 314.
  • Grün, M., Franz, G., In vitro Biosynthesis of the C-Glycosidic Bond in Aloin, Planta, 152 (6):562–564 (1981).
  • Nakatsuka, T., Tomimori, Y., Fukuda, Y., Nukaya, H., First Total Synthesis of Structurally Unique Flavonoids and Their Strong Anti inflammatory Effect, Bioorganic and Medicinal Chemistry Letters, 14 (12): 3201- (2004).
  • Futura, T., Kimura, T., Kondo, S., Mihara, H., Wakimoto, T., Nukaya, H., Tsuji, K., Tanaka, K., Concise Total Synthesis of Flavone CGlycoside Having Potent Anti-inflammatory Activity, Tetrahedron, 60 (42): 9375-9379 (2004).
  • Lin, L., He, X. P., Xu, Q., Chen, G. R., Xie, J., Synthesis of β-C-Glycopyranosyl-1,4-Naphthoquinone Derivatives and Their Cytotoxic Activity, Carbohydrate Research, 343 (4):773-779 (2008).
  • Cavezza, A., Boulle, C., Guéguiniat, A., Pichaud, P., Trouille, S., Ricard, L., Dalko-Csiba, M., Synthesis of Pro-Xylane TM : A New Biologically Active C-Glycoside in Aqueous Media, Bioorganic and Medicinal Chemistry Letters, 19 (3): 845-849 (2009).
  • Lin, L., Shen Q, Xie, J., Chen, G.-R., Synthesis of Triazole-linked beta-C-Glycosyl Dimers as Inhibitors of PTP1B, Bioorganic and Medicinal Chemistry, 16 (22): 9757-9763 (2008).

C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES

Year 2010, Volume 6, Issue 1, 33 - 44, 01.03.2010

Abstract

C-GLİKOZİTLERE GENEL BAKIŞ

Bu derlemede, doğada bolca bulunan ve önemli farmakolojik özelliklere sahip olan bazı C-glikozit
birimlerinden bahsedilmiş ve pek çok türevi olduğu bilinen C-glikozitlerin son yıllarda üzerinde çok
çalışılmış ve önemli biyolojik aktivite gösteren türevlerinin sınıflandırılması yapılmıştır. Bu çalışmada ayrıca
biyolojik aktivite gösteren bazı sentetik C-glikozit birimlerinden ve bunlarla ilgili literatür bilgilerinden
bahsedilmiştir.

GENERAL VIEW TO C-GLYCOSIDES

In this review, C-glycoside units that are abundantly exist on nature and have important
pharmacological are considered, and they are classified regarding to their important biological activities
reported in the recent studies. Some synthetic C-glycoside units having biological activity are further
described based on the literature information in this study.

References

  • Levy, D. E., Tang, C., The Chemistry of CGlycoside, Pergamon, USA (1995).
  • Du, Y., Linhardt, R. J., Vlahov, I. R., Recent Advances in Stereoselective C-glycoside Synthesis, Tetrahedron, 54 (33): 9913-9959 (1998).
  • Tomiyama, H., Kobayashi, Y., Atsushi, N., Tomiyama, A., Tomiyama, N., C-Glycosides and Preparation of Thereof as Antidiabetic Agents, United States Patent No. US 6,627,611 B2 (2003).
  • Gervay, J., Flaherty, T. M., Holmes, D., Studies on the Synthesis of C-glycoside Sulfones as Potential Glycosyl Transferase Inhibitors, Tetrahedron, 53 (48): 16355-16364 (1997).
  • Wellington, K. W., Benner, S. A., A Review: Synthesis of Aryl C-glycosides Via the Heck Coupling Reaction, Nucleosides, Nucleotides, and Nucleic Acids, 25 (12):1309-1333 (2006).
  • Hacksell, U., Daves, G. D. Jr., Edt: Ellis, G.P., West, G. B., The chemistry and biochemistry of C-nucleosides and C-arylglycosides, Progress in Medicinal Chemistry, 22: 1-65 (1985).
  • Darnall, K. R., Townsend, L. B., Robins, R. K., The Structure of Showdomycin, a Novel Carbon-Linked Nucleoside Antibiotic Related to Uridine, Proceedings of the National Academy of Sciences of the United States of America, 57: 548553 (1967).
  • Salem, P. A., Bodey, G. P., Burgess, M. A., Murphy, W. K., Freireich, E. J., A Phase I Study of Pyrazofurin. Cancer (Phila.), 40: 2806-2809 (1977).
  • Westhead, J. E., Price, H. D., Quantitative Assay of Pyrazofurin a New Antiviral, Antitumor, Antibiotic, Antimicrobial Agent and Chemotherapy, 5 (1): 90-91 (1974).
  • Bernardo, S. D., Weigele, M., C-nucleoside antibiotics. 2. Synthesis of Oxazinomycin (minimycin), Journal of Organic Chemistry, 42 (1):109-112 (1977).
  • Cai, D. M., Li M. J., Li, D. L., Synthesis of C-Nucleoside Analogues: 2-[2-(hydroxymethyl)-1,3-dioxolan-5-yl]1,3-thiazole-4-carboxamide and 2-[2-(mercaptometh-yl)-1,3-dioxolan-5-yl]1,3-thiazole-4-carboxamide, Chinese Chemical Letters, 15 (2): 163-166 (2004).
  • Tricot, G., Jayaram, H. N., Weber, G., Hoffman, R., Tiazofurin - Biological Effects and Clinical Uses, International Journal of Cell Cloning, 8 (3): 161-170 (1990).
  • Ramasamy, K. S., Averett, D., A Modified Synthesis of Tiazofurin, Nucleosides & Nucleotides, 18 (11-12): 2425-2431 (1999).
  • Tatar, A., Özkurt, Z., Kiki, İ., Genotoxic Effect of Ribavirin in Patients with CrimeanCongo Hemorrhagic Fever, Japanese Journal of Infectious Diseases, 58 (5): 313-315 (2005).
  • Uchananal, J. G., Stobie, A., Wightman, R., C-Nucleoside Studies. Part XI. Cine-substitution in 1,4-Dinitropyrazoles; Application to the Synthesis of Formycin via Nitropyrazole Derivatives, Canadian Journal of Chemistry, 58 (23):26242627 (1980).
  • Okuda, S., Herbicides. In The Search for Bioactive Compounds from Microorganisms; Omura, S., Ed.; Springer-Verlag: New York, 224-236 (1992).
  • Sağıroglu, A., Özcan, H. M., Bitki Ekstraktlarındaki Flavonoid Aglikonlarının Tayini, 21. Ulusal Kimya Kongresi, İnönü Üniversitesi, Malatya (2007).
  • Granados, E. H., Maldonado, L., A Wacker–Cook Synthesis of Isoflavones: Formononetine, Tetrahedron Letters, 50 (14): 1542-1545 (2009).
  • Delazar, A., Kosarı, A. R., Nazemiyeh, H., Modaresi, M., Gibbons, S., Nahar L., Sarker, S. D., Flavone C-Glycosides and Cucurbitacin Glycosides from Citrullus colocynthis, DARU, 14 (3):109-114 (2006).
  • Grotewold, E., The Science of Flavonoids, Springer, USA (2006).
  • Kim, Y., Jun, M., Jeong, W., Chung, S., Antioxidant Properties of Flavone C-glycosides from Atractylodes Japonica Leaves in Human Low-density Lipoprotein Oxidation, Journal of Food Science, 70 (9): S575-580 (2005).
  • Morsch, M., Girardi, L. G. J., Cechinel-Filho W., Meyre-Silva C., Rodrigues C. A., Separation of C-glycoside Flavonoids from Aleurites moluccana Using Chitin and Full N-Acetylated Chitin, Verlag der Zeitschrift für Naturforschung, 57c: 957-959 (2002).
  • Mishra, B. B., Yadav, S. B., Rakesh, K. S., Tripathi, V., A Novel Flavonoid C-Glycoside from Sphaeranthus indicus L. (Family Compositae), Molecules, 12 (10): 2288-2291 (2007).
  • Yaylı, N., Seyman, H., Baltacı, C., Flavone C-Glycosides from Scleranthus uncinatus, Phytochemistry, 58 (4): 607-610 (2001).
  • Leong, C. N. A, Takao, M., Hanashiro, I., Tamaki, H., Antioxidant Flavonoid Glycosides from the Leaves of Ficus pumila L., Food Chemistry, 109 (2): 415-420 (2008).
  • Martin, F. S., Unified Strategy for the Synthesis of C-Aryl Glycosides, Pure Applied Chemistry, 75 (1): 63-70 (2003).
  • The Merck Index, 11 th Edition, 1850.
  • Allevi, P., Anastasia, M., Ciuffreda, P., Fiecchi, A., Scala, A., Bingham, S., Muir, M., Tyman, J., The First Total Synthesis of Carminic Acid, Journal of the Chemical Society-Chemical Communications, 18: 1319-1320 (1991).
  • Balitz, D. M., O’Herron, F. A., Bush, J., Vyas, D. M., Nettleton, D. E., Grulich, R. E., Bradner, W. T., Doyle, T. W., Arnold, E., Clardy, J., Antitumor Agents from Streptomyces Anandii: Gilvocarcins V, M and E., The Journal of Antibiotics, 34 (12): 1544-1555 (1981).
  • Koyama, Y., Yamaguchi, R., and Suzuki, K., Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin, Angewandte Chemie, 120 (6): 1100-1103 (2008).
  • Kimura, Y., Sumiyoshi, M., Taniguchi, M., Baba, K., Antitumor and Antimetastatic Actions of Anthrone C-Glycoside, Cassialoin Isolated from Cassia garrettiana Heartwood in Colon 26-bearing mice, Japanese Cancer Association, 99 (11): 2336-2348 (2008).
  • Tewtrakul, S., Subhadhirasakul, S., Rattanasuwan, P., HIV-1 Protease Inhibitory Effects of Some Selected Plants in Caesalpiniaceae and Papilionaceae Families, Songklanakarin Journal of Science and Technology, 25 (4): 509-514 (2003).
  • Krenn, L., Pradhan, R., Presser, A., Reznicek, G., Anthrone C-Glycosides from Rheum emodi, Chemical and Pharmaceutical Bulletin 52 (4): 391-393 (2004).
  • Diaz, F., Chai, H-B., Mi, Q., Su, B., Schunke Vigo, J., Graham, J. G., Cabieses, F., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Swanson, S. M., Kinghorn, A. D., Anthrone and Oxanthrone CGlycosides from Picramnia latifolia Collected in Peru, Journal of Natural Products, 67 (3):352–356 (2004).
  • The Merck Index, 12 th Edition, 314.
  • Grün, M., Franz, G., In vitro Biosynthesis of the C-Glycosidic Bond in Aloin, Planta, 152 (6):562–564 (1981).
  • Nakatsuka, T., Tomimori, Y., Fukuda, Y., Nukaya, H., First Total Synthesis of Structurally Unique Flavonoids and Their Strong Anti inflammatory Effect, Bioorganic and Medicinal Chemistry Letters, 14 (12): 3201- (2004).
  • Futura, T., Kimura, T., Kondo, S., Mihara, H., Wakimoto, T., Nukaya, H., Tsuji, K., Tanaka, K., Concise Total Synthesis of Flavone CGlycoside Having Potent Anti-inflammatory Activity, Tetrahedron, 60 (42): 9375-9379 (2004).
  • Lin, L., He, X. P., Xu, Q., Chen, G. R., Xie, J., Synthesis of β-C-Glycopyranosyl-1,4-Naphthoquinone Derivatives and Their Cytotoxic Activity, Carbohydrate Research, 343 (4):773-779 (2008).
  • Cavezza, A., Boulle, C., Guéguiniat, A., Pichaud, P., Trouille, S., Ricard, L., Dalko-Csiba, M., Synthesis of Pro-Xylane TM : A New Biologically Active C-Glycoside in Aqueous Media, Bioorganic and Medicinal Chemistry Letters, 19 (3): 845-849 (2009).
  • Lin, L., Shen Q, Xie, J., Chen, G.-R., Synthesis of Triazole-linked beta-C-Glycosyl Dimers as Inhibitors of PTP1B, Bioorganic and Medicinal Chemistry, 16 (22): 9757-9763 (2008).

Details

Primary Language Turkish
Journal Section Articles
Authors

Nilgün YENİL This is me


Selda KUZU This is me


Emriye AY This is me


Kadir AY This is me

Publication Date March 1, 2010
Acceptance Date
Published in Issue Year 2010, Volume 6, Issue 1

Cite

Bibtex @ { cbayarfbe53372, journal = {Celal Bayar University Journal of Science}, issn = {1305-130X}, eissn = {1305-1385}, address = {}, publisher = {Celal Bayar University}, year = {2010}, volume = {6}, number = {1}, pages = {33 - 44}, title = {C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES}, key = {cite}, author = {Yenil, Nilgün and Kuzu, Selda and Ay, Emriye and Ay, Kadir} }
APA Yenil, N. , Kuzu, S. , Ay, E. & Ay, K. (2010). C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES . Celal Bayar University Journal of Science , 6 (1) , 33-44 . Retrieved from https://dergipark.org.tr/en/pub/cbayarfbe/issue/4049/53372
MLA Yenil, N. , Kuzu, S. , Ay, E. , Ay, K. "C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES" . Celal Bayar University Journal of Science 6 (2010 ): 33-44 <https://dergipark.org.tr/en/pub/cbayarfbe/issue/4049/53372>
Chicago Yenil, N. , Kuzu, S. , Ay, E. , Ay, K. "C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES". Celal Bayar University Journal of Science 6 (2010 ): 33-44
RIS TY - JOUR T1 - C-Glikozitlere Genel Bakış AU - NilgünYenil, SeldaKuzu, EmriyeAy, KadirAy Y1 - 2010 PY - 2010 N1 - DO - T2 - Celal Bayar University Journal of Science JF - Journal JO - JOR SP - 33 EP - 44 VL - 6 IS - 1 SN - 1305-130X-1305-1385 M3 - UR - Y2 - 2022 ER -
EndNote %0 Celal Bayar University Journal of Science C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES %A Nilgün Yenil , Selda Kuzu , Emriye Ay , Kadir Ay %T C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES %D 2010 %J Celal Bayar University Journal of Science %P 1305-130X-1305-1385 %V 6 %N 1 %R %U
ISNAD Yenil, Nilgün , Kuzu, Selda , Ay, Emriye , Ay, Kadir . "C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES". Celal Bayar University Journal of Science 6 / 1 (March 2010): 33-44 .
AMA Yenil N. , Kuzu S. , Ay E. , Ay K. C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES. CBUJOS. 2010; 6(1): 33-44.
Vancouver Yenil N. , Kuzu S. , Ay E. , Ay K. C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES. Celal Bayar University Journal of Science. 2010; 6(1): 33-44.
IEEE N. Yenil , S. Kuzu , E. Ay and K. Ay , "C-GLİKOZİTLERE GENEL BAKIŞ -GENERAL VIEW TO C-GLYCOSIDES", Celal Bayar University Journal of Science, vol. 6, no. 1, pp. 33-44, Mar. 2010