Sains Malaysiana 47(11)(2018): 2693–2698

http://dx.doi.org/10.17576/jsm-2018-4711-12

 

(-)-Glaciantarcin, a New Dipeptide and Some Secondary Metabolites from the Psychrophilic Yeast Glaciozyma antarctica PI12

((-)-Glasiantarsin, satu Dipeptida Terbaharu dan Beberapa Metabolit Sekunder daripada Yis Psikrofilik Glaciozyma antarctica PI12)

 

ANDI R. ROSANDY1, YEOH CHIANN YING3, CHEAH YOKE KQUEEN3, SENG JOE LIM1, JALIFAH LATIP1, A. MUNIR A. MURAD2, MUNTAZ A. BAKAR1 & ROZIDA M. KHALID1*

 

1School of Chemical Science and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

2School of Biosciences and Biotechnology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

3Department of Biomedical Sciences, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor Darul Ehsan, Malaysia

 

Received: 26 March 2018/Accepted: 6 July 2018

 

ABSTRACT

A new dipeptide, (-)-glaciantarcin (1) and three known compounds, cyclo(-Pro-Gly) (2), 1-(2-deoxypentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (3) and vidarabine (Ara-A) (4), were isolated from Glaciozyma antarctica PI12, a cold-adapted yeast. The chemical structures were elucidated by FT-IR, NMR and mass spectrometry. The cytotoxicity and antioxidant activities of compounds 1-4 were evaluated by using the MTT bioassay on MCF-7 (human breast cancer cell line), PC-3 (human prostate cancer cell line) and HEK-293 (normal human embryonic kidney cell line) and DPPH free radical scavenging activity, respectively. At concentration of 400 μM, all compounds showed the highest activity on MCF-7, with compound 1 at 65%, compound 2 (70%), compound 3 (66%) and compound 4 (58%) cell viability. All compounds exhibited weak antioxidant properties. To the best of our knowledge, this is the first report of compounds 1-4 from Glaciozyma antactica.

 

Keywords: Biological activities; dipeptide; (-)-glaciantarcin; Glaciozyma antarctica PI12; psychrophilic yeast

 

ABSTRAK

Satu dipeptida terbaharu iaitu (-)-glasiantarsin (1) dan tiga sebatian yang telah diketahui; siklo (-Pro-Gli) (2), 1- (2-Deoksipentofuranosil) -5-metil-2,4 (1H, 3H) -pirimidinedion (3) dan vidarabin (Ara-A) (4) telah diasingkan daripada Glaciozyma antarctica PI12, yis yang teradaptasi sejuk. Struktur kimia dijelaskan oleh spektroskopi inframerah (IM), ultra lembayung (UL), resonans magnetik nuklear (RMN) dan spektroskopi jisim. Aktiviti kesitotoksikan dan antioksidan daripada sebatian 1-4 dinilai menggunakan bioasai MTT ke atas MCF-7 (sel kanser payudara manusia), PC-3 (sel kanser prostat manusia) dan sel HEK-293 (sel normal) serta aktiviti perencatan radikal bebas DPPH. Pada kepekatan 400 μM, semua sebatian menunjukkan aktiviti tertinggi ke atas MCF-7, iaitu masing-masing: sebatian 1 (62 ± 0.9), 2 (66 ± 1.6), 3 (62 ± 1.3) dan 4 (55 ± 1.7). Kesemua sebatian terpencil menunjukkan sifat antioksidan yang lemah. Sepanjang pengetahuan kami, ini merupakan laporan pertama sebatian 1-4 daripada Glaciozyma antactica.

 

Kata kunci: Aktiviti biologi; dipeptida; (-)-glasiantarsin; Glaciozyma antarctica PI12; yis psikrofilik

REFERENCES

Bergmann, W. & Feeney, R.J. 1951. Contributions to the study of marine products. XXXII. The nucleosides of sponges. I. Journal of Organic Chemistry 16: 981-987.

Brand-Williams, W., Cuvelier, M.E. & Berset, C. 1995. Use of a free radical method to evaluate antioxidant activity. Lebenson Wiss Technol. 28: 25-30.

Connell, L.B., Redman, R., Craig, S., Scorzetti, G., Iszard, M. & Rodriguez, R. 2008. Diversity of soil yeasts isolated from South Victoria Land, Antarctica. Microbial Ecology 56: 448-459.

Di Menna, M.E. 1960. Yeast from Antarctica. Journal of General Microbiology 7: 295-300.

Donachie, S.P. 1995. Ecophysiological description of marine bacteria from Admiralty Bay (Antarctica), and the digestive tracts of selected Euphausiidae. Ph.D. Thesis, Department of Antarctic Biology, Polish Academy of Sciences, Warsaw (Unpublished).

Fell, J.W., Statzell, A., Hunter, I.L. & Phaff, H.J. 1969. Leucosporidium gen. n., the heterobasidiomycetous stage of several yeasts of the genus Candida. Antonie van Leeuwenhoek 35: 433-462.

Furtado, N.A.J.C., Pupo, M.T., Carvalho, I., Campo, V.L., Duarte, M.C.T. & Bastos, J.K. 2005. Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain. Journal of the Brazilian Chemical Society 16: 1448-1453.

Hashim, N.H.F., Bharudin, I., Nguong, D.L.S., Higa, S., Bakar, F.D.A., Nathan, S., Rabu, A., Kawahara, H., Illias, R.M., Najimudin, N., Mahadi, N.M. & Murad, A.M.A. 2013. Characterization of Afp1, an antifreeze protein from the psychrophilic yeast Glaciozyma antarctica PI12. Extremophiles 17: 63-73.

Hashim, N.H.F., Sulaiman, S., Bakar, F.D.A., Illias, R.M., Kawahara, H., Najimudin, N., Mahadi, N.M. & Murad, A.M.A. 2014. Molecular cloning, expression and characterisation of Afp4, an antifreeze protein from Glaciozyma antarctica. Polar Biology 37: 1495-1505.

Ishizu, T., Fujii, A. & Noguchi, S. 1991. Conformational studies of cyclo(L-Phe-L-Pro-Gly-L-Pro)2 by 13C nuclear magnetic resonance. Chemical and Pharmaceutical Bulletin 39: 1617-1619.

Kudo, F., Miyanaga, A. & Eguchi, T. 2014. Biosynthesis of natural products containing β-amino acids. Natural Product Reports 31: 1065-1073.

Lagoja, I.M. 2005. Pyrimidine as constituent of natural biologically active compounds. Chemistry and Biodiversity 2: 1-50.

Lesley-Ann, G. & David, J.N. 2015. Bioactive compounds from terrestrial extremophiles. In Bioactive Compounds from Terrestrial Extremophiles, edited by Giddings, L.A. & Newman, D.J. Springer: Cham.: SpringerBriefs in Microbiology. pp. 1-75.

Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal Immunological Methods 65: 55-63.

Setyowati, E.P., Jenie, U.A., Sudarsono, Kardono, L.B.S. & Rahmat, R. 2008. Identification of cytotoxic constituent of Indonesian Sponge Kaliapsis sp. (Bowerbank). Pakistan Journal of Biological Sciences 11: 2560-2566.

Turchetti, B., Thomas-Hall, S.R., Connell, L.B., Brandam, E., Buzzini, P., Theelen, B., Müller, W.H. & Boekhout, T. 2011. Psychrophilic yeasts from Antarctica and European glaciers: Description of Glaciozyma gen. nov., Glaciozyma martinii sp. nov. and Glaciozyma watsonii sp. nov. Extremophiles 15: 573-586.

Turkiewicz, M., Pazgier, M., Donachie, S.P. & Kalinowska, H. 2005. Invertase and α-glucosidase production by the endemic Antarctic marine yeast Leucosporidium antarcticum. Polar Research 26: 125-136.

Wang, B., Dong, J., Zhou, X., Lee, K.J., Huang, R., Zhang, S. & Liu, Y. 2009. Nucleosides from the marine sponge Haliciona sp. Zeitschrift für Natürforschung 64: 143-148.

*Corresponding author; email: rozidakhalid@ukm.edu.my

 

 

 

 

 

 

previous