Abstract
Three antioxidant and anti-inflammatory oxygenated meroterpenoids, 1-(3-methoxypropyl)-2-propylcyclohexane (C13) (1), 3-(methoxymethyl)heptyl 3-(cyclohex-3-enyl) propanoate (C18) (2), and 2-ethyl-6-(4-methoxy-2-((2-oxotetrahydro-2H-pyran-4-yl)methyl)butoxy)-6-oxohexyl 5-ethyloct-4-enoate (C29) (3) were purified from the methanol:ethyl acetate fraction of red seaweed Kappaphycus alvarezii (family Solieriaceae) collected from the Gulf-of-Mannar on the southeast coast of peninsular India. The highly oxygenated C29 meroterpenoid 3 displayed potential antioxidative activities (IC50 < 0.35 mg/mL) as evaluated by 2, 2’-azino-bis (3-ethylbenzothiazoline)-6-sulphonic acid and 1, 1-diphenyl-2-picryl-hydrazil free radical scavenging assays. The compound 3 displayed potential in vitro inhibitory activities towards pro-inflammatory 5-lipoxidase (IC50 1.04 mg/mL), which indicated its potential anti-inflammatory properties against inducible inflammatory mediators causing an inflammatory response. Structure-activity relationship analyses displayed the functional roles of lipophilic-hydrophobic characteristics and electronic parameter to determine its potential anti-inflammatory activity in terms of inhibiting inducible inflammatory cyclooxygenase and lipoxidase.
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References
Areche C, Benites J, Cornejo A, Ruiz LM, García-Beltrán O, Simirgiotis MJ, Sepúlveda B (2015) Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model. Mar Drugs 13:1726–1738
Ask EI, Azanza RV (2002) Advances in cultivation technology of commercial eucheumatoid species: a review with suggestions for future research. Aquacult 206:257–277
Baylac S, Racine P (2003) Inhibition of 5-lipoxygenase by essential oils and other natural fragment extracts. Int J Aromather 13:138–142
Cai YZ, Mei S, Jie X, Luo Q, Corke H (2006) Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Life Sci 78:2872–2888
Chakraborty K, Joseph D, Joy M, Raola VK (2016) Characterization of substituted aryl meroterpenoids from red seaweed Hypnea musciformis as potential antioxidants. Food Chem 212:778–788
Chandrasekaran S, Nagendran AN, Pandiaraja D, Krishnankutty N, Kamalakannan B (2008) Bioinvasion of Kappaphycus alvarezii on corals in the Gulf of Mannar, India. Curr Sci 94:1167–1172
Ebada SS, Lin WH, Proksch P (2010) Bioactive sesterterpenes and triterpenes from marine sponges: occurrence and pharmacological significance. Mar Drugs 8:313–346
Gershenzon J, Dudareva N (2007) The function of terpene natural products in the natural world. Nat Chem Biol 3:408–414
Larsen LN, Dahl E, Bremer J (1996) Peroxidative oxidation of leuco-dichloroluorescein by prostaglandin H synthase in prostaglandin biosynthesis from polyunsaturated fatty acids. BBA Lipid Met 1299:47–53
Liebgott T, Miollan M, Berchadsky Y, Drieu K, Culcasi M, Pietri S (2000) Complementary cardioprotective effects of flavonoid metabolites and terpenoid constituents of Ginkgo biloba extract (EGb 761) during ischemia and reperfusion. Basic Res Cardiol 95:368–377
Lipinski C, Hopkins A (2004) Navigating chemical space for biology and medicine. Nature 432:855–861
Makkar F, Chakraborty K (2017a) Unprecedented antioxidative cyclic ether from the red seaweed Kappaphycus alvarezii with anti-cyclooxygenase and lipoxidase activities Nat Prod Res 31(10):1131–1141
Makkar F, Chakraborty K (2017b) Antidiabetic and anti-inflammatory potential of sulphated polygalactans from red seaweeds Kappaphycus alvarezii and Gracilaria opuntia Int J Food Prop 20(6):1326–1337
Makkar F, Chakraborty K (2017c) Antioxidative sulfated polygalactans from marine macroalgae as angiotensin-I converting enzyme inhibitors. Nat Prod Res. https://doi.org/10.1080/14786419.2017.1363756.
Makkar F, Chakraborty K (2017d) Previously undescribed antioxidative azonicyl morpholinone alkaloid from red seaweed Gracilaria opuntia with anti-cyclooxygenase and lipoxidase properties. Nat Prod Res 32(10):1150–1160
Parshikov IA, Netrusov AI, Sutherland JB (2012) Microbial transformation of antimalarial terpenoids. Biotechnol Adv 30:1516–1523
Pietta PG (2000) Flavonoids as antioxidants. J Nat Prod 63:1035–1042
Reis VM, Oliveira LS, Passos RMF, Viana NB, Mermelstein C, Sant’Anna C, Pereira RC, Paradas WC, Thompson FL, Amado-Filho GM, Salgado LT (2013) Traffic of secondary metabolites to cell surface in the red alga Laurencia dendroidea depends on a two-step transport by the cytoskeleton. PLoS One 8:63929
Zbakh H, Talero E, Avila J, Alcaide A, de los Reyes C, Zubía E, Motilva V (2016) The algal meroterpene 11-hydroxy-11-O-methylamentadione ameloriates dextran sulfate sodium-induced colitis in mice. Mar Drugs 14:149
Acknowledgements
Financial support 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. The authors 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. FM acknowledges Department of Science and Technology, for the award of fellowship.
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These authors contributed equally: Fasina Makkar and Kajal Chakraborty
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Makkar, F., Chakraborty, K. Antioxidant and anti-inflammatory oxygenated meroterpenoids from the thalli of red seaweed Kappaphycus alvarezii. Med Chem Res 27, 2016–2026 (2018). https://doi.org/10.1007/s00044-018-2210-0
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DOI: https://doi.org/10.1007/s00044-018-2210-0