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

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.

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Abstract

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).

Item Type:	Article
Uncontrolled Keywords:	Gracilaria opuntia ; Red seaweed ; Furanyl natural products ; Furanyl methyloxepinyl ; Pharmacological activities; Anti-inflammatory selectivity indices
Subjects:	Fish Biotechnology > Bioactive compound Biochemistry Algae > Seaweed
Divisions:	CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division Subject Area > CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division
Depositing User:	Arun Surendran
Date Deposited:	03 Apr 2018 06:46
Last Modified:	03 Apr 2018 06:46
URI:	http://eprints.cmfri.org.in/id/eprint/12662

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