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Medicinal Chemistry Research

, Volume 27, Issue 4, pp 1245–1259 | Cite as

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

  • Fasina Makkar
  • Kajal ChakrabortyEmail author
Original Research

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-tetrahydro-1H-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 anti-inflammatory 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-COX-1IC50/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).

Keywords

Gracilaria opuntia Red seaweed Furanyl natural products Furanyl methyloxepinyl Pharmacological activities Anti-inflammatory selectivity indices 

Notes

Acknowledgements

This work is financially supported from the Science and Engineering Research Board (SERB) of Department of Science and Technology, Ministry of Science and Technology in the form of research grant (SR/S1/OC-96/2012 SERB) is gratefully acknowledged. We thank the Director, Central Marine Fisheries Research Institute, for his guidance and support. Thanks are due to the Head, Marine Biotechnology Division, Central Marine Fisheries Research Institute for facilitating the research activity. F.M. acknowledges Department of Science and Technology, for the award of fellowship.

Compliance with ethical standards

Conflict of interest

The authors declare no conflicts of interest in this work.

Ethical standards

This article does not contain any studies with human participants or animals performed by any of the authors.

Supplementary material

44_2018_2144_MOESM1_ESM.doc (1.7 mb)
Supplementary Information

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Marine Bioprospecting Section of Marine Biotechnology DivisionCentral Marine Fisheries Research InstituteCochinIndia

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