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Novel furanyl derivatives from the red seaweed Gracilaria opuntia with pharmacological activities using different in vitro models

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Relation http://eprints.cmfri.org.in/12662/
https://link.springer.com/article/10.1007/s00044-018-2144-6
 
Title Novel furanyl derivatives from the
red seaweed Gracilaria opuntia with
pharmacological activities using different in
vitro models
 
Creator Makkar, Fasina
Chakraborty, Kajal
 
Subject Bioactive compound
Biochemistry
Seaweed
 
Description Two previously undescribed furanyl compounds, characterized as 5-(7-(5-ethyl-3,4-dimethoxycyclooctyl) benzofuran-6-yl)-
7-methyl-3,4,7,8-tetrahydro-2H-oxocin-2-one (compound 1) and 2-(3-ethyl-9-(2-methoxyethoxy)-1-oxo-2,3,4,9-tetrahydro1H-xanthen-2-yl)
ethyl-5-hydroxy-9-methoxy-7,8-dimethyl-8-(5-methylfuran-2-yl) nona-3,6-dienoate (compound 2) were
derived from the ethyl acetate–methanol (EtOAc:MeOH) crude extract of red seaweed Gracilaria opuntia. The isolated
compounds are the first furanyl natural products featuring methoxycyclooctyl benzofuran with tetrahydro-2H-oxocin
framework and tetrahydro-1H-xanthenyl methoxy methylfuran skeletons. These compounds were assessed for antiinflammatory
activities against pro-inflammatory cyclooxygenase-2/5-lipoxygenase (COX-1, 2, and 5-LOX) and
antioxidative effects in various in vitro models. The methylfuran derivative exhibited comparable inhibitory activities
towards 5 LOX (IC50 0.209 × 10−2 M) with synthetic non-steroidal anti-inflammatory drugs (NSAID) ibuprofen (IC50
0.451 × 10−2 M, P < 0.05), which indicated its potential anti-inflammatory properties. The antioxidative properties of the
furanyl derivatives as resolved by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2ʹ-azino-bis (3-ethylbenzothiazoline-6-
sulfonic acid (ABTS) free radical scavenging activities were found to be significantly greater (IC50 ~0.051–0.055 × 10−2 M)
than those exhibited by α-tocopherol (IC50 > 0.146 × 10−2 M), and were similar to those displayed by the synthetic
antioxidants (butylated hydroxytoluene (BHT)/ butylated hydroxyanisole (BHA) (IC50 ~0.144–0.189 × 10−2 M, P < 0.05).
The anti-inflammatory selectivity indices of the isolated compounds recorded significantly greater values (SI: anti-COX1IC50/anti-COX-2IC50
~1.08–1.09) than NSAIDs (aspirin, and ibuprofen, SI: 0.02 and 0.44, respectively, P < 0.05), and
consequently, appeared to be safer. The isolated compounds showed significant anti-diabetic properties as determined by α-
amylase/α-glucosidase (IC50 < 0.052 × 10−2 M) and dipeptidyl peptidase-4 (DPP-4, IC50 < 0.002 × 10−2 M) inhibitory
activities. The angiotensin converting enzyme-I (ACE-I) inhibitory activity of the compounds (IC50 0.023–0.024 × 10−2 M)
was found to be comparable with that recorded by commercial ACE inhibitor, captopril (IC50 0.037 × 10−2 M).
 
Date 2018
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/12662/1/Kajal%20Chakraborty_Fasina%20Makkar_2018_Novel%20furanyl%20derivatives%20from%20the%20red%20seaweed%20Gracilaria%20opuntia_Medicinal%20Chemistry%20Research.pdf
Makkar, Fasina and Chakraborty, Kajal (2018) Novel furanyl derivatives from the red seaweed Gracilaria opuntia with pharmacological activities using different in vitro models. Medicinal Chemistry Research, 27. pp. 1245-1259.