UJI AKTIVITAS ANTIJAMUR BEBERAPA SENYAWA MONOKARBONIL ANALOG CURCUMIN HASIL SINTESIS

Ismi Rahmawati, Desi Purwaningsih

Abstract


Antifungal Activity of Some Synthesized Mono-Carbonyl Analogue Compounds of Curcumin


ABSTRACT

Fungal resistance can pose a threat to future fungal infections, therefore studies to find other compounds that have antifungal activity need to be done. The aim of this study was to examine antifungal activity of synthesized curcumin analogue compounds i.e. 2,6-Bis-(2'-furilidin)-cyclohexanone (26FuH); 2,5-Bis-(2'-furilidine)-cyclopentanone (25FuP) and 1,5-Difuril-1,4-pentadien-3-on (15FuA). The curcumin analogue compound was successfully synthesized with Aldol condensation using KOH 7.5% as the catalyst. The compound was purified and characterized by melting point, thin layer chromatography, gas chromatography with mass spectrometry, FTIR spectrophotometry, spectrophotometry 1H-NMR. The results showed pure compounds and have a structure that corresponds to the target compounds. All compound were assayed as antifungal against Candida albicans, Pityrosporum ovale, Aspergillus niger, and Trichophyton mentagrophytes. The activity of each compound represented by inhibitory diameter was analyzed by one-way ANOVA followed by post hoc Tukey (p<0.05). All three compounds showed antifungal activity against Candida albicans, Pityrosporum ovale, and Aspergillus niger. The best antifungal activity was shown by 26FuH against Pityrosporum ovale.

Keywords: antifungal activity, curcumin, monocarbonyl, Pityrosporum ovale, synthesis

 

ABSTRAK

Resistensi jamur dapat menjadi ancaman pada kasus infeksi jamur di masa mendatang, oleh sebab itu penelitian untuk menemukan senyawa lain yang memiliki aktivitas antijamur perlu dilakukan. Penelitian ini bertujuan untuk menguji aktivitas antijamur senyawa analog curcumin hasil sintesis yaitu senyawa 2,6-Bis-(2’-furilidin)-sikloheksanon (26FuH); 2,5-Bis-(2’-furilidin)-siklopentanon (25FuP) dan 1,5-Difuril-1,4-pentadien-3-on (15FuA). Senyawa analog curcumin sudah berhasil disintesis dengan metode kondensasi Aldol menggunakan katalis KOH 7,5%. Senyawa hasil sintesis dimurnikan dan dikarakterisasi dengan menggunakan pemeriksaan organoleptis, titik lebur, kromatografi lapis tipis, kromatografi gas dengan spektrometri massa, spektrofotometri FTIR, spektrofotometri 1H-NMR. Hasil menunjukkan senyawa murni dan struktur sesuai senyawa target. Hasil sintesis diuji aktivitas antijamur terhadap Candida albicans, Pityrosporum ovale, Aspergillus niger dan Trichophyton mentagrophytes. Hasil diameter daya hambat dianalisis dengan ANOVA satu arah dilanjutkan post hoc Tukey (p<0,05). Ketiga senyawa memiliki aktivitas antijamur terhadap jamur Candida albicans, Pityrosporum ovale, dan Aspergillus niger. Aktivitas antijamur terbaik adalah senyawa 26FuH terhadap jamur Pityrosporum ovale.

Kata Kunci: aktivitas antijamur, curcumin, monokarbonil, Pityrosporum ovale, sintesis


Keywords


aktivitas antijamur; curcumin; monokarbonil; Pityrosporum ovale; sintesis

Full Text:

PDF

References


Anggarini DR, Sukanto H, Astari L, Endraswari PD (2015) Uji kepekaan griseofulvin, ketokonasol, itrakonasol, dan terbinafin terhadap spesies dermatofit dengan metode mikrodilusi. BIKKK 27:55-62

Apsari AS, Adiguna MS (2013) Resistensi antijamur dan strategi untuk mengatasi. MDVI 40:89-95

Braga SFP, Alves EVP, Ferreira RS, Fradico JRB, Lage PS, Duarte MC, Ribeiro TG, Júnior PA, Romanha AJ, Tonini ML, Steindel M, Coelho EF, de Oliveira RB (2014) Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones. Eur J Med Chem 71:282-289. doi: 10.1016/j.ejmech.2013.11.011

CLSI (2012) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard. Ninth Edition. CLSI document M07-A9. Clinical and Laboratory, Standards Institute. Wayne, Pennsylvania USA

Heger M, van Golen RF, Broekgaarden M, Michel MC (2014) The Molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancers, Pharmacol Rev 66:222-307. doi: 10.1124/pr.110.004044

Jawetz E, Melnick JL, Adelberg EA (2016) Medical Microbiology, 27th Edition. McGraw-Hill Education

Katsori AM, Chatzopoulou M, Dimas K, Kontogiorgis C, Patsilinakos A, Trangas T, Hadjipavlou-Litina D (2011) Curcumin analogues as possible anti-proliferative & anti-inflammatory agents. Eur J Med Chem 46:2722-2735. doi:10.1016/ j.ejmech.2011.03.060

Kemenkes (2012) Profil Kesehatan Indonesia Tahun 2011. ISBN 978-602-235-106-1. Kementerian Kesehatan Republik Indonesia, Jakarta

Khalil OAK, de Faria Oliveira OMM, Vellosa JCR, de Quadros AU, Dalposso LM, Karam TK, Mainardes RM, Khalil NM (2012) Curcumin antifungal and antioxidant activities are increased in the presence of ascorbic acid. Food Chem 133:1001-1005. doi: 10.1016/ j.foodchem.2012.02.009

Kudo C, Yamakoshi H, Sato A, Nanjo H, Ohori H, Ishioka C, Iwabuchi Y, Shibata H (2011) Synthesis of 86 species of 1,5-diaryl-3-oxo-1,4-pentadienes analogs of curcumin can yield a good lead in vivo. BMC Pharmacol 11:4. doi: 10.1186/1471-2210-11-4

Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X, Yang S (2009) Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents. Bioorg Med Chem 17:2623–2631. doi: 10.1016/j.bmc.2008.10.044

Martins CV, da Silva DL, Neres AT, Magalhaes TF, Watanabe GA, Modolo LV, Sabino AA, de Fatima A, de Resende MA (2008) Curcumin as a promising antifungal of clinical interest. J Antimicrob Chemother 63:337-339. doi: 10.1093/jac/dkn488

Moghadamtousi SZ, Kadir HA, Hassandarvish P, Tajik H, Abubakar S, Zandi K (2014) A Review on antibacterial, antiviral, and antifungal activity of curcumin. BioMed Research International. ID 186864. 12p. doi: 10.1155/2014/186864

Nirwati H, Praseno, Mustofa M (2014) Isolasi Candida sp dan pola kepekaannya terhadap berbagai antijamur di Laboratorium Mikrobiologi Fakultas Kedokteran UGM. Libmed UGM pp:126-136, Yogyakarta

Podunavac-Kuzmanović SO, Cvetković DD (2011) Lipophilicity and antifungal activity of some 2-substituted benzimidazole derivatives. Chemical Industry & Chemical Engineering Quarterly 17:9-15. doi: 10.2298/CICEQ100329044P

Rahmawati I (2009) Sintesis dan uji aktivitas antibakteri senyawa 2,6-bis-(2’-Furilidin)-sikloheksanon; 2,5-bis-(2’-Furilidin)-siklopentanon; 1,5-difuril-1,4-pentadien-3-on, Thesis, Universitas Setia Budi

Sardjiman (2000) Synthesis of some new series of curcumin analogues, antioxidative, antiinflammatory, antibacterial activities and qualitative-structure activity relationship. Thesis, Gadjah Mada University

Thomas G (2003) Fundamentals of Medicinal Chemistry. John Wiley & Sons Ltd, West Sussex, England

Xiao J, Chu Y, Hu K, Wan J, Huang Y, Jiang C, Liang G, Li X (2010) Synthesis and biological analysis of a new curcumin analogue for enhanced anti-tumor activity in HepG 2 cells. Oncol Rep 23:1435-1441. doi: 10.3892/or_00000781

Yugo MR dan Ridhawati (2013) Pola kepekaan Candida albicans terhadap flukonazol dan itrakonazol secara in vitro: Tinjauan pada bahan klinik Laboratorium Mikologi Departemen Parasitologi FKUI Periode 2010-2011. Program Studi Pendidikan Dokter Fakultas Kedokteran, Universitas Indonesia

Zhao F, Dong HH, Wang YH, Wang TY, Yan ZH, Yan F, Zhang DZ, Cao YY, Jin YS (2017) Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant Candida spp. Medchemcomm 8:1093–1102. doi: 10.1039/c6md00649c

 

 




DOI: http://dx.doi.org/10.29122/jbbi.v5i2.2835

Refbacks

  • There are currently no refbacks.


© Copyright: BY-NC-SA