α-Glucosidase Inhibitory and A Leptospermone Derivative from Rhodomyrtus tomentosa

https://doi.org/10.22146/ijc.40990

Ferlinahayati Ferlinahayati(1*), Daniel Alfarado(2), Eliza Eliza(3), Budi Untari(4)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Sriwijaya, Jl. Raya Palembang Prabumulih Km 32, Ogan Ilir 30622, South Sumatera, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Sriwijaya, Jl. Raya Palembang Prabumulih Km 32, Ogan Ilir 30622, South Sumatera, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Sriwijaya, Jl. Raya Palembang Prabumulih Km 32, Ogan Ilir 30622, South Sumatera, Indonesia
(4) Department of Pharmacy, Faculty of Mathematics and Natural Sciences, University of Sriwijaya, Jl. Raya Palembang Prabumulih Km 32, Ogan Ilir 30622, South Sumatera, Indonesia
(*) Corresponding Author

Abstract


One of the treatments for diabetes mellitus disease is to control blood sugar level using an inhibitor of α-glucosidase enzyme. The methanol extracts of the fruit, stem, and leaves of Rhodomyrtus tomentosa were found significant in inhibiting α-glucosidase with an IC50 value of 20.57, 20.36 and 43.99 μg/mL respectively. The ethyl acetate and n-butanol fractions from the methanol extract of R. tomentosa fruit exhibited the potent inhibition (IC50 13.49 and 19.29 μg/mL) compare to acarbose and n-hexane fraction (IC50 383.68 and 1175.16 μg/mL). A leptospermone derivative, rhodomyrtosone D, was isolated from the ethyl acetate fraction of R. tomentosa fruit. The structure of rhodomyrtosone D was identified based on spectroscopic analysis, as well as comparing with literature data. The α-glucosidase inhibition of rhodomyrtosone D (IC50 110.45 μg/mL) was 3.5 fold more potent than acarbose. Thus, R. tomentosa plant could be potential as a natural resource of α-glucosidase inhibitor.

Keywords


α-glucosidase; Rhodomyrtus tomentosa; antidiabetic; rhodomyrtosone D; ethyl acetate fraction

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References

[1] Yin, Z., Zhang, W., Feng, F., Zhang, Y., and Kang, W., 2014, α-Glucosidase inhibitors isolated from medicinal plants, Food Sci. Hum. Wellness, 3 (3-4), 136–174.

[2] Choudhary, M.I., Adhikari, A., Rasheed, S., Marasini, B.P., Hussain, N., Kaleem, W.A., and Rahman, A., 2011, Cyclopeptyde alkaloid of Ziziphus oxyphylla Edgw as novel inhibitors of α-glucosidase enzyme and protein glycation, Phytochem. Lett., 4 (4), 404–406.

[3] Ortiz-Andrade, R.R., Jimenez, S.G., Castillo-España, P., Ramírez-Ávila, G., Villalobos-Molina, R., and Estrada-Soto, E., 2007, α-Glucosidase inhibitory activity of the methanolic extract from Tournefortia hartwegiana: An anti-hyperglycemic agent, J. Ethnopharmacol., 109 (1), 48–53.

[4] Lam, S.H., Cheng, J.M., Kang, C.J., Chen, C.H., and Lee, S.S., 2008, α-Glucosidase inhibitors from the seed of Syagrus romanzoffiana, Phytochemistry, 69 (5), 1173–1178.

[5] Zhang, A.J., Rimando, A.M., Mizuno, C.S., and Mathews, S.T., 2017, α-Glucosidase inhibitory effect of resveratrol and piceatannol, J. Nutr. Biochem., 47, 86–93.

[6] Kim, J.S., Yang, J., and Kim, M.J., 2011, Alpha glucosidase inhibitory effect, anti-microbial activity and UPLC analysis of Rhus verniciflua under various extract conditions, J. Med. Plants Res., 5 (5), 778–783.

[7] Lavanya, G., Voravuthikunchai, S.P., and Towatana, N.H., 2012, Acetone extract from Rhodomyrtus tomentosa: A potent natural antioxidant, Evid. Based Complement. Alternat. Med., 2012, 535479.

[8] Limsuwan, S., Kayser, O., and Voravuthikunchai, S.P., 2012, Antibacterial activity of Rhodomyrtus tomentosa (Aiton) Hassk. leaf extract against clinical isolates of Streptococcus pyogenes, Evid. Based Complement. Alternat. Med., 2012, 697183.

[9] Lai, T.N.H., Herent, M.F., Quetin-Leclercq, J., Nguyen, T.B.T., Rogez, H., Larondelle, Y., and André, C.M., 2013, Piceatannol, a potent bioactive stilbene, as major phenolic component in Rhodomyrtus tomentosa, Food Chem., 138 (2-3), 1421–1430.

[10] Wu, P., Ma, G., Li, N., Deng, Q., Yin, Y., and Huang, R., 2015, Investigation of in vitro and in vivo antioxidant activities of flavonoids rich extract from the berries of Rhodomyrtus tomentosa (Ait.) Hassk., Food Chem., 173, 194–202.

[11] Hiranrat, A., Mahabusakaram, W., Carrol, A.R., Duffy, S., and Avery, V.M., 2012, Tomentosones A and B, hexacyclic phloroglucinol derivatives from the Thai shrub Rhodomyrtus tomentosa, J. Org. Chem., 77 (1), 680–683.

[12] Limsuwan, S., Trip, E.N., Kouwen, T.R.H.M., Piersma, S., Hiranrat, A., Mahabusakaram, W., Voravuthikunchai, S.P., van Dijl, J.M., and Kayse, O., 2009, Rhodomyrtone, a new candidate as natural antibacterial drug from Rhodomyrtus tomentosa, Phytomedicine, 16 (6-7), 645–651.

[13] Liu, H.X., Zhang, W.M., Xu, Z.F., Chen, Y.C., Tan, H.B., and Qiu, S.X., 2016, Isolation, synthesis and biological activity of tomentosenol A from the leaves of Rhodomyrtus tomentosa, RSC Adv., 6 (31), 25882–25886.

[14] Shou, Q., Smith, J.E., Mon, H., Brkljača, Z., Smith, A.S., Smith, D.M., Griesser, H.J., and Wohlmuth, H., 2014, Rhodomyrtals A-D, four unusual phloroglucinol-sesquiterpene adducts from Rhodomyrtus psidioides, RSC Adv., 4 (26), 13514–13517.

[15] Anisah, L.N., Syafii, W., Pari, G., and Sari, R.K., 2018, Antidiabetic activities and identification of chemical compound from Samama (Anthocephalus macrophyllus (Roxb) Havil), Indones. J. Chem., 18 (1), 66–74.

[16] Yang, Z., Wang, Y., Wang, Y., and Zhang, Y., 2012, Bioassay-guided screening and isolation of a-glucosidase and tyrosinase inhibitors from leaves of Morus alba, Food Chem., 131 (2), 617–625.

[17] You, Q., Chen, F., Wang, X., Luo, P.G., and Jiang, Y., 2011, Inhibitory effect of muscadine anthocyanins on α-glucosidase and pancreatic lipase activities, J. Agric. Food Chem., 59 (17), 9506–9511.

[18] Luo, J.G., Ma, L., and Kong, L.Y., 2008, New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana, Bioorg. Med. Chem., 16 (6), 2912–2920.

[19] Hiranrat, A., and Mahabusakaram, W., 2008, New acylphloroglucinols from the leaves of Rhodomyrtus tomentosa, Tetrahedron, 64 (49), 11193–11197.

[20] Liu, J., Song, J.G., Su, J.C., Huang, X.J., Ye, W.C., and Wang, Y., 2018, Tomentodione E, a new sec-pentyl syncarpic acid-based meroterpenoid from the leaves of Rhodomyrtus tomentosa, J. Asian Nat. Prod. Res., 20 (1), 67–74.

[21] Hui, W.H., and Li, M.M., 1976, Two new triterpenoids from Rhodomyrtus tomentosa, Phytochemistry, 15 (11), 1741–1743.



DOI: https://doi.org/10.22146/ijc.40990

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