Skip to main content
SpringerLink
Log in

Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

Previously undescribed oxygenated heterocyclic metabolites were purified from the ethyl acetate fraction of natural mangrove hybrid Rhizophora annamalayana. The purified metabolites were characterized as 11-(tetrahydro-14α-hydroxy-13β-methylfuran-12-yl)-10β-methylbutyl benzoate (1), 13-(tetrahydro-15β,16α-dimethyl-18-oxo-2H-pyran-14-yl)-10β-methylhept-12(E)-enyl benzoate (2), and dihydro-11-((7E)-2-hydroxy-8β-methyl-2H-chromen-9-yl)-13-methylpent-12(E)-enyl)-17β-methylfuran-19(3H)-one (3) by the combined spectroscopic experiments. These metabolites were assessed for their antioxidant and anti-inflammatory activities, and compared with the commercially available standards. The purified compound 3 exhibited greater antioxidant activities as deduced by 2, 2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid and 2, 2-diphenyl-1-picrylhydrazyl quenching properties (IC50 2.10 and 2.22 mM, respectively) compared to the positive control (α-tocopherol, IC50 1.46 and 1.69 mM, respectively). Consequently, the anti-inflammatory activity of compound 3 with regard to the inhibitory property towards pro-inflammatory 5-lipoxygenase was greater (IC50 2.16 mM) than that exhibited by the synthetic anti-inflammatory drug ibuprofen (IC50 4.51 mM). Electronic and hydrophobic parameters were deduced to find the target bioactivities of the studied compounds. These oxygenated heterocyclic metabolites could be used as potential therapeutic lead compounds in the pharmaceutical applications.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Ajay A, Walters WP, Murcko MA, (1998) Can we learn to distinguish between "drug-like" and "nondrug-like" molecules? J Med Chem 41(18):3314–3324

    Article  PubMed  CAS  Google Scholar 

  • Alikunhi NM, Kandasamy K, Manoharan C, Subramanian M (2012) Insulin-like antigen of mangrove leaves and its anti-diabetic activity in alloxan-induced diabetic rats. Nat Prod Res 26:1161–1166

    Article  PubMed  CAS  Google Scholar 

  • 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

    Article  PubMed  CAS  Google Scholar 

  • Chakraborty K, Raola VK (2017) Two rare antioxidant and anti-inflammatory oleanenes from loop root Asiatic mangrove Rhizophora mucronata. Phytochem 135:160–168

    Article  CAS  Google Scholar 

  • Chakraborty K, Raola VK (2018) Previously undescribed benzoxepins with bioactivities against inducible pro-inflammatory cyclooxygenase and lipoxygenase from Rhizophora annamalayana Kathir. Nat Prod Res 8:1–9. https://doi.org/10.1080/14786419.2018.1446008

    Article  CAS  Google Scholar 

  • Costa FN, da Silva MD, Borges RM, Leitao GG (2014) Isolation of phenolics from Rhizophora mangle by combined counter-current chromatography and gel-filtration. Nat Prod Commun 9:1729–1731

    PubMed  Google Scholar 

  • Hegazy MEF, Mohamed TA, Alhammady MA, Shaheen AM, Reda EH, Elshamy AI, Aziz M, Paré PW (2015) Molecular architecture and biomedical leads of terpenes from red sea marine invertebrates. Mar Drugs 13:3154–3181

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Ishige K, Schubert D, Sagara Y (2001) Flavonids protect neuronal cells from oxidative stress by three distinct mechanisms. Free Radic Biol Med 30:433–446

    Article  PubMed  CAS  Google Scholar 

  • Jameel M, Ali A, Ali M (2015) Isolation of antioxidant phytoconstituents from the seeds of Lens culinaris Medik. Food Chem 175:358–365

    Article  PubMed  CAS  Google Scholar 

  • Kathiresan K,(1999) Rhizophora annamalayana Kathir (Rhizophoraceae), a new nothospecies from Pichavaram mangrove forest in Southeastern peninsular India Environ Ecol 17(2):500–501

    Google Scholar 

  • Kusuma S, Kumar PA, Boopalan K, (2011) Potent antimicrobial activity of Rhizophora mucronata J Ecobiotechnol. 3:40–41

    Google Scholar 

  • Lakshmi M, Parani M, Senthilkumar P, Parida A (2002) Molecular phylogeny of mangroves VIII: Analysis of mitochondrial DNA variation for species identification and relationships in Indian mangrove Rhizophoraceae. Wetl Ecol Manag 10(5):355–362

    Article  CAS  Google Scholar 

  • Laskar S, Brahmachari G (2014) Access to biologically relevant diverse chromene heterocycles via multicomponent reactions (MCRs): Recent advances. J Org Biomol Chem 2:1–50

    Google Scholar 

  • Lim YY, Lim TT, Tee JJ (2007) Antioxidant properties of several tropical fruits: A comparative study. Food Chem 103:1003–1008

    Article  CAS  Google Scholar 

  • Martins JN, Figueiredo FS, Martins GR, Leitão GG, Costa FN (2017) Diterpenes and a new benzaldehyde from the mangrove plant Rhizophora mangle. Rev Bras Farmacogn 27(2):175–178

    Article  CAS  Google Scholar 

  • Moovendhan M, Ramasubburayan R, Vairamani S, Shanmugam A, Palavesam A, Immanuel G (2015) Antibiotic efficacy and characterization of mangrove metabolites against UTI Microbes. J Herbs Spices Med. Plants 21:129–139

    Article  CAS  Google Scholar 

  • Nebula M, Harisankar HS, Chandramohanakumar N (2013) Metabolites and bioactivities of Rhizophoraceae mangroves. Nat Prod Bioprospect 3:207–232

    Article  PubMed Central  CAS  Google Scholar 

  • Parani M, Lakshmi M, Elango S, Ram N, Anuratha CS, Parida A (1997) Molecular phylogeny of mangroves II. Intra and inter-specific variation in Avicennia revealed by RAPD and RFLP markers. Genome 40(4):487–495

    Article  PubMed  CAS  Google Scholar 

  • Ragavan P, Jayaraj RSC, Saxena A, Mohan PM, Ravichandran K (2015) Taxonomical identity of Rhizophora×annamalayana Kathir and Rhizophora×lamarckii Montrouz (Rhizophoraceae) in the Andaman and Nicobar Islands, India. Taiwania 60:183–193

    Google Scholar 

  • Raola VK, Chakraborty K (2017a) Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (Family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase. Nat Prod Res 31(4):418–427

    Article  PubMed  CAS  Google Scholar 

  • Raola VK, Chakraborty K (2017b) Biogenic guaianolide-type sesquiterpene lactones with antioxidative and anti-inflammatory properties from natural mangrove hybrid Rhizophora annamalayana. Nat Prod Res 31(23):2719–2729

    Article  PubMed  CAS  Google Scholar 

  • Rocha-Santos T, Duarte A (2014) Introduction to the analysis of bioactive compounds in marine samples. In: Barcelo D (ed). Comprehensive analytical chemistry: Analysis of marine samples in search of bioactive compounds. vol 65, 1st edn, Elsevier, Portugal, pp. 312.

  • Rohini RM, Das AK (2010) Triterpenoids from the stem bark of Rhizophora mucronata. Nat Prod Res 24:197–202

    Article  PubMed  CAS  Google Scholar 

  • Shin HJ, Pil GB, Heo SJ, Lee HS, Lee JS, Lee YJ, Lee J, Won HS, (2016) Anti-Inflammatory activity of tanzawaic acid derivatives from a marine-derived fungus Penicillium steckii 108YD142 Mar Drugs 14:14

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Tettamanzi MC, Biurrun FN, Cirigliano AM (2007) A new antifeedant withanolide from Jaborosa lanigera. Z Naturforsch 62:573–576

    Article  CAS  Google Scholar 

  • Venkateswarlu Y, Reddy MVR (1994) Three new heptaprenylhydroquinone derivatives from the sponge Ircinia fasciculata. J Nat Prod 57:1286–1289

    Article  CAS  Google Scholar 

  • Wang J, Xiang W, Guo Y (2004) Agallochaols A and B, two new diterpenes from the Chinese mangrove Excoecaria agallocha. Helv Chim Acta 87:2829–2833

    Article  CAS  Google Scholar 

  • Wang J, Xiang W, Guo Y (2005) Secoatisane- and isopimarane-tpye diterpenoids from the Chinese mangrove Excoecaria agallocha L. Helv Chim Acta 88:979–985

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was supported by the Indian Council of Agricultural Research (ICAR) Network Project High-Value Compounds (grant no. HVC/ICAR 2012–2017). We thank the Director, Central Marine Fisheries Research Institute for support. Thanks are due to the Head, Marine Biotechnology Division, Central Marine Fisheries Research Institute for facilitating the research activity. VR wishes to acknowledge ICAR, for the award of a scholarship.

Author information

Authors and Affiliations

  1. Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North P.O., P.B. No. 1603, Cochin, India

    Kajal Chakraborty & Vamshi Krishna Raola

  2. Department of Chemistry, Mangalore University, Mangalagangothri, Mangalore, Karnataka State, 574199, India

    Vamshi Krishna Raola

Authors
  1. Kajal Chakraborty
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vamshi Krishna Raola
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kajal Chakraborty.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chakraborty, K., Raola, V.K. Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana. Med Chem Res 27, 1679–1689 (2018). https://doi.org/10.1007/s00044-018-2182-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-018-2182-0

Keywords

Search

Navigation