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
Diserahkan: 26 Mac 2018/Diterima:
6 Julai 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
RUJUKAN
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.
*Pengarang
untuk surat-menyurat;
email: rozidakhalid@ukm.edu.my