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