By employing crude peroxidases extracted from sawi hijau (Brassica juncea) as biocatalyst, licarin A was synthesized from isoeugenol. The structure was elucidated and confirmed by mass spectrometer (MS) and nuclear magnetic resonance (NMR) analysis. This compound displayed moderate cytotoxicity effect on MCF-7 breast cancer cell with IC50 = 59.95±1.87 µg/mL, compared to doxorubicin with IC50 value of 0.88±0.34 µg/mL as the positive control. These results are indirectly in line with our previously published in silico tests which indicated that licarin A was not a potent ligand for estrogen receptor alpha (ERα), but either a non-ligand or a moderate ligand for ERα.
REFERENCES
1.
Ferlay
, J.
; Shin
, H.R.
; Bray
, F.
; Forman
, D.
; Mathers
, C.
; Parkin
, M.
2010
. Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008
. Int. J. Cancer
, 127
, 2893
–2917
.2.
Thambi
, D.
, Bharat
, B.A.
2004
. Role of chemopreventive agents in cancer theraphy
., Cancer Letters
, 215
, 129
–140
.3.
Murakami
, Y.
;Shoji
, M.
;Hirata
, A.
;Tanaka
, S.
;Yokoe
, I.
;Fujisawa
, S.
2004
. Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages
. Archives of Biochemistry and Biophysics
, 434
, 326
–332
.4.
Findik
, E.
; Ceylan
, M.
; Elmastas
, M.
2011
. Isoeugenol-based novel potent antioxidants: Synthesis and reactivity
. European Journal of Medicinal Chemistry
, 46
, 4618
–4624
.5.
Anita
, Y.
; Radifar
, M.
; Kardono
, L.B.S.
; Hanafi
, M.
; Istyastono
, EP
. 2012
. Structure-based design of eugenol analogs as potential estrogen receptor antagonists
. Journal of Bioinformation
, 8
(19
), 901
–906
6.
Llevot
, A.
; Grau
, E.
; Carlotti
, S.
; Grelier
, S.
; Cramail
, H.
2016
. Selective laccase-catalyzed dimerization of phenolic compounds derived from lignin: Towards original symmetrical bio-based (bis) aromatic monomers
. Journal of Molecular Catalysis B: Enzymatic
, 125
, 34
–41
.7.
8.
Camoutsis
C.
; Sambani
C.
; Trafalis
D.T.P.
; Peristeris
P.
1999
. On the formation of steroidal amidoesters of 4-[N,N-bis(2-chloroethyl)amino]benzoic acid and their cytotoxic activity
. Eur J Med Chem
, 34
, 645
–649
.9.
De Farias Dias
A.
1988
. An improved high yield synthesis of dehydrodieugenol
. Phytochemistry
, 27
, 3008
–9
.10.
Sjoblad
, R.D.
, Minard
R.D.
, Bollag
J-M.
1976
. Polymerization of I-naphthol and related phenolic compounds by an extracellular fungal enzyme
. Pesticide Biochemistry and Physiology
, 6
, 457
–63
.11.
Van Deurzen
M.P.J.
, Van Rantjiwk
F.
, Sheldon
R.A.
1997
. Selective oxidations catalyzed by peroxidases
. Tetrahedron
, 53
, 13183
–13220
.12.
Tzeng
S.C.
, Liu
Y.C.
2004
. Peroxidase-catalyzed synthesis of neolignan and its anti-inflammatory activity
. Journal of Molecular Catalysis B: Enzymatic
, 32
, 7
–13
.13.
Giraud
M.
, Bernad
N.
, Martinez
J.
, Cavelier
F.
2001
. New general strategy of dimerization of bioactive molecules
. Tetrahedron Letters, 42, 1895 –1897.
14.
Venables
, W.N.
; Smith
, D.M. R.
2008
. Development Core Team: An Introduction to R: Notes on R, A Programming Environment for Data Analysis and Graphics
., Electronic edition.
15.
Istyastono
, E. P.
2015
. Employing Recursive Partition and Regression Tree Method to Increase the Quality of Structure-Based Virtual Screening in the Estrogen Receptor Alpha Ligands Identification
. Asian J. Pharm. Clin. Res
, 8
(6
), 21
–24
.16.
Huang
, N.
; Shoichet
, B. K.
; Irwin
, J. J.
2006
. Benchmarking Sets for Molecular Docking
. J. Med. Chem
, 49
(23
), 6789
–6801
.17.
Mysinger
, M. M.
; Carchia
, M.
; Irwin
, J. J.
; Shoichet
, B. K.
2012
. Directory of Useful Decoys, Enhanced (DUD-E): Better Ligands and Decoys for Better Benchmarking
. J. Med. Chem,
55
(14
), 6582
–6594
.18.
Brooks
, SC.
; Locke
, ER.
; Soule
, HD
. 1973
. Estrogen receptor in a human cell line (MCF-7) from breast carcinoma
. J. Biol. Chem.
, 248
(10
), 6251
–6253
.19.
Istyastono
, E. P.
; Riswanto
, F. D. O.
; Yuliani
, S. H.
2015
. Computer-Aided Drug Repurposing: A Cyclooxygenase-2 Inhibitor Celecoxib as a Ligand for Estrogen Receptor Alpha
. Indones. J. Chem
, 15
(3
), 274
–280
.20.
Setiawati
, A.
; Riswanto
, F. D. O.
; Yuliani
, S. H.
; Istyastono
, E. P.
2014
. Retrospective Validation of a Structure-Based Virtual Screening Protocol to Identify Ligands for Estrogen Receptor Alpha and Its Application to Identify the Alpha-Mangostin Binding Pose
. Indo. J. Chem
, 14
(2
), 103
–108
.21.
Radifar
, M.
; Yuniarti
, N.
; Istyastono
, E. P.
2013
b. PyPLIF: Python-Based Protein-Ligand Interaction Fingerprinting
. Bioinformation
, 9
(6
), 325
–328
.22.
Radifar
, M.
; Yuniarti
, N.
; Istyastono
, E. P.
2013
a. PyPLIF-Assisted Redocking Indomethacin-(R)-Alpha-Ethyl-Ethanolamide into Cyclooxygenase-1
. Indones. J. Chem,
13
(3
), 283
–286
.
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