Application of Xanten and Its Derivatives in Human and Veterinary Medicine

Öz

Xanthene derivatives represent cyclic, organic compounds that can be natural, semi-synthetic and synthetic origin. These compounds become very interesting because of various pharmacological activities such as antibacterial, antiviral and anti-inflammatory properties. Furthermore, they have been utilized as antagonists for drug-resistant leukemia lines and in photodynamic therapy. They are also applied as dyes in laser technology and pH sensitive fluorescent materials for visualization of biomolecules. Because of new diseases in veterinary medicine, application of these compounds can be very useful and literature describes activity of similar compunds in veterinary research field. In this review the most important activity of xanthen derivatives such as antibacterial, antifungal, antihelmintic, antiprotozoal, anticancerogenic and antidiabetic activity and mechanism of their action are presented.

Anahtar Kelimeler

• Xanthene derivatives,Pharmacology activities,Veterinary medicine

Xanten ve türevlerinin insan ve veteriner hekimlikte kullanımı

Öz

Ksanten türevleri, doğal, yarı sentetik ve sentetik kökenli olabilen siklik, organik bileşikleri temsil eder. Bu bileşikler, antibakteriyel, antiviral ve antienflamatuar özellikler gibi çeşitli farmakolojik aktiviteler nedeniyle dikkat çekmektedirler. Ayrıca, ilaca dirençli lösemi hatları için ve fotodinamik tedavide antagonistler olarak kullanılmaktadırlar. Ayrıca lazer teknolojisinde boyalar ve biyomoleküllerin görselleştirilmesi için pH'a duyarlı floresan malzemeler olarak uygulanırlar. Veteriner hekimlik alanında yeni hastalıklar nedeniyle, bu bileşiklerin uygulanması çok faydalı olabilir ve literatürde Veteriner araştırma alanındaki benzer bileşiklerin aktivitesi açıklanmaktadır. Bu derlemede ksanten türevlerinin antibakteriyel, antifungal, antihelmintik, antiprotozoal, antikanserojenik ve antidiyabetik aktivite gibi en önemli aktiviteleri ve etki mekanizmaları sunulmuştur.

Anahtar Kelimeler

• Ksanten türevleri,Farmakolojik aktiviteler,Veterinerlik

Kaynakça

1. 1. Cai K., Wang Y., Guo Z., Xu X., Li H., Zhang Q., 2018. Clinical characteristics and antimicrobial resistance of pneumococcal isolates of pediatric invasive pneumococcal disease in China. Infect Drug Resist, 11, 2461-2469. 2. Fotie J., Bohle DS., 2006. Pharmacological and biological activities of xanthones. Anti-Infect Agent Med Chem, 5, 15-31. 3. Negi JS., Bisht VK., Singh P., Rawat MSM., Joshi GP., 2013. Naturally occurring canthones: chemistry and biology. J App Chem, 1, 1-9. 4. Marona H., Szkaradek N., Karczewska E., Trojanowska D., Budak A., Bober P., Przepiorka W., Cegla M., Szneler E., 2009. Antifungal and Antibacterial Activity of the Newly Synthesized 2-Xanthone Derivates. Arch Pharm (Weinheim), 342, 9-18. 5. Garcia D., Escalante M., Delgado R., Ubeira FM., Leiro J., 2003. Anthelminthic and antiallergic activities of Mangifera indica L. stem bark components Vimang and mangiferin. Phytother Res, 17, 1203-1208. 6. Veljovic E., Spirtovic-Halilovic S., Muratovic S., Valek Zulj L., Roca S., Trifunovic S., Osmanovic A., Davorka Z., 2015. 9-Aryl substituted hydroxylated xanthen-3-ones: Synthesis, structure and antioxidant potency evaluation. Croat Chem Acta, 88, 121-127. 7. Mariano LN., Da Silva LM., De Souza P., Boeing T., Somensi LB., Bonomini TJ., Delle Monache F., Cechinel Filho V., de Andrade SF., Niero R., 2016. Gastroprotective xanthones isolated from Garcinia achachairu: Study on mucosal defensive factors and H (+), K(+)-ATPase activity. Chem Biol Interact, 258, 30-39. 8. Irondi EA., Oboh G., Akindahunsi AA., 2016. Antidiabetic effects of Mangifera indica Kernel Flour-supplemented diet in streptozotocin-induced type 2 diabetes in rats. Food Sci Nutr, 4, 828-839. 9. Peres V., Nagem TJ., 1997. Naturally occurring, pentaoxygenated, hexaoxygenated and dimeric xanthones: A literature survey. Quimica Nova, 20, 388-397. 10. Veljovic E., Spirtovic-Halilovic S., Muratovic S., Osmanovic A., Haveric S., Haveric A., Hadzic M., Salihovic M., Malenica M., Sapcanin A., Zavrsnik D., 2019. Antiproliferative and genotoxic potential of xanthen-3-one derivatives. Acta Pharm, 69, 683-694. 11. Tantapakul C., Maneerat W., Sripisut T., Ritthiwigrom T., Andersen RJ., Cheng P., Cheenpracha S., Raksat A., Laphookhieo S., 2016. New Benzophenones and Xanthones from Cratoxylum sumatranum ssp. neriifolium and Their Antibacterial and Antioxidant Activities. J Agric Food Chem, 64, 8755-8762. 12. Stoilova I., Gargova S., Stoyanova A., Ho I., 2005. Antimicrobial and antioxidant activity of the polyphenol mangiferin. Herba Polonica, 51, 1-2. 13. Iinuma M., Tosa H., Tanaka T., Asai F., Kobayashi Y., Shimano R., Miyauchi K., 1996. Antibacterial activity of xanthones from guttiferaeous plants against methicillin-resistant Staphylococcus aureus. Pharm Pharmacol, 48, 861-865. 14. Sakagami Y., Iinuma M., Piyasena KG., Dharmaratne HR., 2005. Antibacterial activity of alpha-mangostin against vancomycin resistant Enterococci (VRE) and synergism with antibiotics. Phytomedicine, 12, 203-208. 15. Szkaradek N., Stachura K., Waszkielewicz AM., Cegla M., Szneler E., Marona H., 2008. Synthesis and antimycobacterial assay of some xanthone derivatives. Acta Polon pharm, 65, 21-28. 16. Guzman-Beltran S., Rubio-Badillo MA., Juarez E., Hernandez-Sanchez F., Torres M., 2016. Nordihydroguaiaretic acid (NDGA) and α-mangostin inhibit the growth of Mycobacterium tuberculosis by inducing autophagy. Int Immunopharm, 31, 149-157. 17. Sudta P., Jiarawapi P., Suksamrarn A., Hongmanee P., Suksamrarn S., 2013. Potent activity against multidrug-resistant Mycobacterium tuberculosis of α-mangostin analogs. Chem Pharm Bull, 61, 194-203. 18. Veljovic E., Spirtovic-Halilovic S., Muratovic S., Salihovic M., Novakovic I., Osmanovic A., Zavrsnik D., 2018. Antimicrobial activity and docking study of synthesized xanthen-3-on derivatives. RJPBCS, 9, 777-783. 19. Veljovic E., Spirtovic-Halilovic S., Kahrovic E., Roca S., Novakovic I., Osmanovic A., Salihovic M., Alagic D., Benjamin H., Dzenana L., Zavrsnik D., 2016. Solvent-free Synthesis and Antibacterial Activity of 14-Aryl Substituted Dibenzoxanthene Derivatives. Bull Chem Tech Bosnia and Herzegovina, 46, 33-38. 20. Futuro DO., Ferreira PG., Nicoletti CD., Borbasantos LP., Da Silva F., Rozental S., Ferreira VF., 2018. The antifungal activity of naphthoquinones: An integrative review. Ann Acad Bras Cienc, 1, 90. 21. Moro P. and Schantz M.P., 2009. Echinococcosis: a review. International Journal of Infectious Diseases, 13, 125-133. 22. Zuko A., 1999. Parasites and parasitoses in ruminants in the upland regions in Bosnia and Herzegovina. Veterinaria, 48, 95-120. 23. Keiser J., Vargas M., Winter R., 2012. Anthelminthic properties of mangostin and mangostin diacetate. Parasitol Int, 61, 369-371. 24. Ondeyka JG., Dombrowski AW., Polishook JP., Felcetto T., Shoop WL., Guan Z., Singh SB., 2006. Isolation and insecticidal/anthelmintic activity of xanthonol, a novel bis-xanthone, from a Non-sporulating fungal species. J Antibiotics, 59, 288-292. 25. Aukkanimart R., Boonmars T., Sriraj P., Songsri J., Laummaunwai P., Waraasawapati S., Boonyarat C., Rattanasuwan P., Boonjaraspinyo S., 2015. Anthelmintic, anti-inflammatory and antioxidant effects of Garcinia mangostana extract in hamster opisthorchiasis. Exp Parasitol, 154, 5-13. 26. Garcia-Bustos JF., Sleebs BE., Gasser RB., 2019. An appraisal of natural products active against parasitic nematodes of animals. Parasit Vectors, 12, 306. 27. Scott H., Ralf W., 2007. One-pot synthesis of new symmetric and asymmetric xanthene dyes. Tetrahedron Lett, 48, 4383-4385. 28. Shao-liang Z., Philp C., 2005 Synthesis, structures, photoluminescence and theoretical studies of xanthone in crystalline resorcinarene-based inclusion complexes. Chem Eur J, 11, 3583-3590. 29. Sousa E., Correia da Silva M., Pinto M., 2009. In: Natural Products Chemistry, Biochemistry and Pharmacology, Ed., Narosa Publishing House PVT. LTD., 392-416, West Bengal, India. 30. Eunice MT., 2006. Antiprotozoal activity against plasmodium falciparum and trypanosoma cruzi of xanthones isolated from chrysochlamys tenuis. Pharm Biol, 7, 550-553. 31. Fotie J., Bohle S., 2006. Pharmacological and biological activities of xanthones. Curr Med Chem-Anti-Infect Agents, 5, 15-31. 32. Pinto M., Castanheiro R., 2009. In: Natural Products Chemistry, Biochemistry and Pharmacology, Ed., Narosa Publishing House PVT. LTD., 520-675, West Bengal, India. 33. Kaiser M., Maser P., Tadoori LP., Loset JR., Brun R., 2015. Antiprotozoal activity profiling of approved drugs: A starting point toward drug repositioning. PLOS ONE, 10, 8. 34. Fukai T., Yonekawa M., Hou AJ., Nomura T., Sun HD., Uno J., 2003. Antifungal agents from the roots of Cudrania cochinchinensis against Candida, Cryptococcus, and Aspergillus species. J Nat Prod, 66, 1118-1120. 35. Jean F., Scott B., 2003. Pharmacological activities of xanthones. Anti-Inf Agents in Med Chem, 3, 11-17.