Isolation, characterisation, anticancer and anti-oxidant activities of 2-methoxy mucic acid from Rhizophora apiculata: an in vitro and in silico studies

Abstract

The main objective of the present study is to isolate and characterise the novel bioactive molecule, 2-methoxy mucic acid (4) from Rhizophora apiculate Blume under the Rhizophoraceae family. In this study, the 2-methoxy mucic acid (4) was isolated for the first time from the methanolic extract of the leaves of R. apiculata. Anticancer activity of 2-methoxy mucic acid (4) was evaluated against HeLa and MDA-MB-231 cancer cell lines and they displayed promising activity with IC₅₀ values of 22.88283 ± 0.72 µg/ml in HeLa and 2.91925 ± 0.52 µg/ml in the case of MDA-MB-231, respectively. Furthermore, the antioxidant property of 2-methoxy mucic acid (4) was found to be (IC₅₀) 21.361 ± 0.41 µg/ml. Apart from in vitro studies, we also performed extensive in silico studies (molecular docking and molecular dynamics simulation) on four critical antiapoptotic Bcl-2 family members (Bcl-2, Bcl-w, Bcl-xL and Bcl-B) towards 2-methoxy mucic acid (4). The results revealed that this molecule showed higher binding affinity towards Bcl-B protein (ΔG = −5.8 kcal/mol) and the structural stability of this protein was significantly improved upon binding of this molecule. The present study affords vital insights into the importance of 2-methoxy mucic acid (4) from R. apiculata. Furthermore, it opens the therapeutic route for the discovery of anticancer drugs.

Research Highlights

• This is a first report on a bioactive compound identified and characterised; a novel 2-methoxy mucic acid derived from methanolic crude extract from the leaves of R. apiculata from ANI.

• Estimated binding free energy of 2-methoxy mucic acid is found to be −5.8 kcal/mol to the anti-apoptotic Bcl-B protein.

• 2-methoxy mucic acid showed both significant anti-cancer and anti-oxidant activity.

Communicated by Ramaswamy H. Sarma

Keywords:

• Rhizophora apiculata
• 2-methoxy mucic acid
• in vitro and in silico studies
• anticancer and antioxidant activities

Acknowledgements

We thank the Director of the National Centre for Sustainable Coastal Management and the SAIF, IIT-Madras for providing the NMR and HRMS spectra for this study. We earnestly acknowledge our gratitude to the Forest Department, ANI for mangroves collection in ANI and the field survey. JM and MJ thanks Sharda University for support. This study was undertaken as part of the In-house research study “Traditional Knowledge of tribal communities in Islands of India with reference to medicinal plants project ” (NCSCM Contribution number: NCSCM/PUB/2021/0006). Views expressed in this research paper are of the authors only and not necessarily of the affiliated organisations.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This study was financially and technically supported by the Ministry of Environment, Forest and Climate Change, Government of India, and the World Bank under the India ICZM Project (P097985).