Malaysian Journal of Analytical Sciences Vol 21 No 6 (2017):
1243 - 1249
DOI:
10.17576/mjas-2017-2106-05
DIKETOPIPERAZINE PRODUCED BY PSYCHROPHILIC
YEAST Glaciozyma antarctica PI12
(Diketopiperazin Dihasilkan oleh Yis
Psikropilik Glaciozyma antarctica
PI12)
Andi Rifki Rosandy1,
Muntaz Abu Bakar1, Nurul Nadiah Abdul Rahman1, Abdul
Munir Abdul Murad2,
Azira Muhamad3, Rozida Mohd.
Khalid1*
1School of Chemical Science and Food Technology, Faculty of Science and
Technology
2School of Biosciences and Biotechnology, Faculty of Science and Technology
Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia
3Malaysia Genome Institute
(MGI),
National Institute of Biotechnology Malaysia, Jalan Bangi, 43000 Kajang, Selangor, Malaysia
*Corresponding author: rozidakhalid@ukm.edu.my
Received: 7
June 2017; Accepted: 1 November 2017
Abstract
Four diketopiperazine derivatives;
cyclo(-Pro-Val) (1), (-)-cyclo(-Pro-Tyr) (2), (-)-cyclo(-Pro-Phe) (3)
and (+)-cyclo(-Pro-Leu) (4) were isolated from the ethyl acetate
extract of Glaciozyma antarctica PI12, a cold-adapted yeast that belongs
to family Kriegeriales. The compounds were isolated by radial chromatography
and thin layer chromatography techniques and the chemical structures were
elucidated by infrared (IR), ultraviolet (UV), nuclear magnetic resonance (NMR)
spectroscopy and mass spectrometry.
Keywords: Glaciozyma antarctica PI12, diketopiperazine, Kriegeriales
Abstrak
Empat terbitan
diketopiperazin; siklo(-Pro-Val) (1),
(-)-siklo(-Pro-Tir) (2), (-)-siklo(-Pro-Phe)
(3) and (+)-siklo(-Pro-Leu) (4) yang dipencilkan daripada ektrak
etil asetat Glaciozyma antarctica
PI12, merupakan yis adaptasi sejuk yang terdiri dari famili Kriegeriales.
Sebatian – sebatian terpencil telah diasingkan menggunakan teknik kromatografi
pepejal dan kromatografi lapisan nipis dan struktur kimia dijelaskan oleh
spektroskopi infra merah (IM), ultra lembayung (UL), resonans magnetik nuklear
(RMN) dan spektrometri jisim.
Kata kunci: Glaciozyma antarctica PI12, diketopiperazin, Kriegeriales
References
1.
Ruisi, S., Barreca, D., Selbmann, L., Zucconi, L. and Onofri,
S. (2007). Fungi in Antarctica. Reviews
in Environmental Science and Biotechnology, 6: 127 – 141.
2.
Nienow, J. A. and Friedmann, E. I. (1993). Terrestrial
litophytic (rock) communities. In: Friedmann, E. I. (ed). Antarctica
microbiology. Wiley-Liss, New York, pp. 343 – 412.
3.
Friedmann, E. I. (1993). Antarctic microbiology. Wiley-Liss, New York, pp.
634.
4.
Morgan-Kiss, R. M., Priscu, J. C., Pocock, T., Gudynaite-Savitch, L. and
Humer, N. P. (2006). Adaptation and acclimation of photosynthetic
microorganisms to permanently cold environments. Microbiology and Molecular Biology Reviews, 70: 222 – 252.
5.
Morgan, R. Y. (1975). Psychrophilic bacteria. Bacteriological Reviews, 39: 144 – 167.
6.
Giddings, L. A. and Newman, D. J. (2015). Bioactive compounds
from terrestrial extremophiles. Springer, New York, pp. 1.
7.
Sewald, N. and Jakubke, H. D. (2002). Peptides: Chemistry and
biology. NJ: Wiley, Berlin, pp. 119 –124.
8.
Di Menna, M. E. (1960). Yeast from Antarctica. Journal of
General Microbiology, 7:
295 – 300.
9.
Fell, J. W., Statzell, A., Hunter,
I. L. and Phaff, H. J. (1969). Leucosporidium gen. n., the
heterobasidiomycetous stage of several yeasts of the genus Candida. Antonie van Leeuwenhoek, 35: 433 – 462.
10.
Turchetti, B., Thomas-Hall, S. R., Connell, L. B., Branda. E.,
Buzzini, P., Theelen, B., Müller, W. H. and 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.
11.
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.
12.
Connell, L. B., Redman, R., Craig, S., Scorzetti, G., Iszard,
M. and Rodriguez, R. (2008). Diversity of soil yeasts isolated from South
Victoria Land, Antarctica. Microbial
Ecology, 56: 448 – 459.
13.
Pazgier, M., Turkiewicz, M., Kalinowska, H. and Bielecki, S. 2003. The
unique cold-adapted extracellular subtilase from psychrophilic yeast Leucosporidium antarcticum. Journal of Molecular Catalysis B: Enzymatic,
21: 39 – 42.
14.
Hashim, N. H. F., Sulaiman, S., Bakar, F. D. A., Illias, R.
M., Kawahara, H., Najimudin, N., Mahadi, N. M. and Murad, A. M. A. (2014).
Molecular cloning, expression and characterisation of Afp4, an antifreeze
protein from Glaciozyma antarctica. Polar Biology, 37: 1495 – 1505.
15.
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. and Murad, A. M. A. (2013). Characterization of Afp1, an
antifreeze protein from the psychrophilic yeast Glaciozyma antarctica PI12. Extremophiles,
17: 63 – 73.
16.
Lee, H. B., Choi, Y. C. and Kim, S. U. (1994). Isolation and
identification of Maculosins from Streptomyces
rochei 87051-3. Agricultural Chemistry and Biotechnology,
37(5): 339 – 342.
17.
Furtado, N. A. J. C., Pupo, M. T., Carvalho, I., Campo, V.
L., Duarte, M. C. T., and Bastos, J. K. (2005). Diketopiperazines produced by
an Aspergillus fumigatus Brazilian strain. Journal of the Brazilian Chemical Society,
16(6B): 1448 – 1453.
18.
Vasquez-Rivera, D., González, O., Guzmán-Rodríguez, J., Diaz-Pérez,
A. L., Ochoa-Zarzosa, A., Lopez-Bucio, J., Meza-Carmen, V. and Campos-García, G.
(2015). Cytotoxicity of cyclodipeptides from Pseudomonas aeruginosa PAO1 leads to apoptosis in human cancer cell lines. BioMed Research International, 2015: 1 – 9.
19.
Jermnak, U., Chinaphuti, A., Poapolathep, A., Kawai, R., Nagasawa, H. and
Sakuda, S. (2013). Prevention of aflatoxin contamination by a soil bacterium of
Stenotrophomonas sp. that produces
aflatoxin production inhibitors. Microbiology,
159: 902 – 912.
20.
Laatsch, H. (2010). AntiBase a data base for rapid
dereplication and structure determination of microbial natural products. Wiley-VCH.
Germany, Wein-heim.
21.
Guo, Q., Guo, D., Zhao, B., Xu, J. and Li, R. (2007). Two cyclic dipeptides from Pseudomonas
fluorescens GcM5-1A carried by the pine wood nematode and their toxicities
to Japanese black pine suspension cells and seedlings in vitro. Journal of Nematology, 39(3): 243 – 247.
22.
Cheenpracha,
S., Borris, R. P., Tran, T. T., Jee, J. M., Seow, H. F., Cheah, H. Y., Ho, C.
C. and Chang, L. C. (2011). Three new
amides from Streptomyces sp.
H7372. Journal of the Brazilian Chemical Society, 22(2): 223 – 229.
23.
Munekata, M. and Tamura, G. (1981). Selective inhibition of
SV40-transformed cell growth by diketopiperazines. Agricultural and Biological Chemistry, 45(11): 2613 – 2618.
24.
Puopolo, G., Cimmino, A., Palmieri, M. C., Giovannini, O., Evidente, A.
and I. Pertot, I. (2014). Lysobacter
capsici AZ78 produces cyclo(L-Pro-L-Tyr), a 2,5-diketopiperazine with toxic
activity against sporangia of Phytophthora
infestans and Plasmopara viticola.
Journal of Applied Microbiology, 117:
1168-1180.
25.
Hamza, A. A., Ali, H. A., Clark, B. R., Murphy, C. D. and Elobied, E. A. (2013).
Cyclo (L-phenyl, L-prolyl).
Diketopiperazines from a newly isolated Streptomyces sudanensis. A4.4. Journal of
Biotechnology and Pharmaceutical Research,
4(1): 1 – 7.
26.
Wang, Y., Mueller, U. G. and Clardy, J. (1999). Antifungal
diketopiperazines from symbiotic fungus of fungus-growing ant Cyphomyrmex minitus. Journal of Chemical Ecology, 25(4): 935
– 941.
27.
Stierle, A. C., Cardellina, J. H. and Strobelt, G. A. (1988). Maculosin, a
host-specific phytotoxin for spotted knapweed from Alternaria Alternata. Proceedings
of the National Academy of Sciences of the United States of America, 85:
8008 – 8011.
28.
Yap, A. C., Kok-Gan Chan, K. G. and Choo, Y. M. (2016).
Isolation and identification of metabolites from the Gram-negative proteobacteria
of Burkholderia cenocepacia and Serratia marcescens. Sains Malaysiana, 45(7): 1073 – 1077.
29.
Musetti, R., Polizzotto, R., Vecchione, A., Borselli, S., Zulini, L.,
D’Ambrosio , M., di Toppi, L. S. and Pertot, I. (2007). Antifungal activity of diketopiperazines
extracted from Alternaria alternata
against Plasmopara viticola: An
ultrastructural study. Micron, 38:
643 – 650.
30.
Luis, S. M., Ballesteros, J. and Gutiérrez, M. (2011). Antibacterial
constituents from the octocoral associated bacterium Pseudoalteromonas sp.
Revista Latinoamericana
de Química, 39: 1 – 2.
31.
Wang, X., Huang, Y., Sheng, Y., Su, P., Qiu, Y., Ke, C. and Feng, D.
(2017). Antifouling activity towards mussel by small-molecule compounds from a
strain of Vibrio alginolyticus bacterium
associated with Sea Anemone Haliplanella
sp. Journal of Microbiology and
Biotechnology, 27(3): 460–470.