Journal of Medicinal and Aromatic Plant Sciences

Volume: 43 Issue: 1

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  • Original Research Article

Bioassay-guided isolation and characterization of potential α-glucosidase inhibitors from the seeds of Quassia indica Gaetrn.

PRABHA B1,#, BIJI M1,2,#, MADHUKRISHNAN M1,2, SHERIN DR3, RESHMITHA TR2,4, SUNIL VARUGHESE1,2, MANOJKUMAR TK3 ,NISHA P2,4, RADHAKRISHNAN KV1,2,*
 

*Corresponding author; E-mail: [email protected]
#These authors contributed equally
1Chemical Sciences and Technology Division, 4Agroprocessing and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram-695019, India
2Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
3Centre for Computational Modeling and Data Engineering, Indian Institute of Information Technology and Management, Thiruvananthapuram- 695581, India

Year: 2021, Page: 25-36, Doi: https://doi.org/10.62029/jmaps.v43i1.B

Received: June 12, 2021 Accepted: June 20, 2021 Published: July 1, 2021

Abstract

Bioactivity-guided isolation afforded 10 compounds from the ethanolic extract of the seeds of Quassia indica including, four novel quassinoids namely; samaderin L (6), samaderin R (7), samaderoside L (9) and samaderoside R (10). The structures were illustrated based on 1D and 2D NMR data, HRESIMS and singlecrystal X-ray analysis. Among the quassinoids, samaderoside R (10) displayed significant α-glucosidase inhibitory activity. Molecular simulation experiments proved that samaderoside R (10) effectively binds to the active sites of Saccharomyces cerevisiae (3A4A) and human maltase glucoamylase (N- and C-terminal: 2QMJ and 3TOP) enzymes.
 

Keywords: Molecular simulation studies, Quassia indica Gaetrn, Quassinoids, -Glucosidase inhibitory activity

References

Adisakwattana S, Lerdsuwankij O, Poputtachai U, Minipun A, Suparpprom C. 2011. Inhibitory activity of cinnamon bark species and their combination effect with acarbose against intestinal α-glucosidase and pancreatic α-amylase. Pl Food Hum Nutr 66:143-148.

Apostolidis E, Kwon YI, Shetty K. 2007. Inhibitory potential of herb, fruit, and fungal- enriched cheese against key enzymes linked to type 2 diabetes and hypertension. Innov. Food Sci Emerg 8: 46-54.

Chougale AD, Ghadyale VA, Panaskar SN, Arvindekar AU.2009. Alpha-glucosidase inhibition by stem extract of Tinospora cordifolia. J Enzyme Inhib Med Chem 24: 998-1001.

De Fronzo RA, Ferrannini E, Groop L, Henry RR, Herman WH, Holst JJ, Hu FB, Kahn CR, Raz I, Shulman GI, Simonson DC, Testa MA, Weiss R.2015. Type 2 diabetes mellitus. Nat Rev Dis Primers 1: 1-22.

Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, Halgren TA, Sanschagrin PC, Mainz DT.2006. Extra Precision Glide: Docking and Scoring Incorporating a Model of Hydrophobic Enclosure for Protein-Ligand Complexes. J Med Chem 49: 6177–6196.

Gopalan G, Prabha B, Joe A, Reshmitha TR, Sherin DR, Sabu M, Manojkumar T K, Radhakrishnan KV, Nisha P. 2019. Antidiabetic properties of apiforol, a potential lead isolated from the seeds of Musa balbisiana. J Sci Food Agric 99: 2521-2529.

Halgren TA, Murphy RB, Friesner RA, Beard HS, Frye LL, Pollard WT, Banks JL.2004. Glide: A new approach for rapid, accurate docking and scoring. 2. enrichment factors in database screening. J Med Chem 47: 1750–1759.

Iasmine ABSA, Henrique MM, Luiz ALS, Karina PR. 2014. Simaroubaceae family: botany, chemical composition and biological activities. Rev Bras Farmacogn 24: 481-501.

International Diabetes Federation. (2017). from http://www.diabetesatlas.org

Isao K, Taifo M, Ko-ichi Y, Shinsaku N, Tadanori M, Motomasa K, Hirotaka S. 1996. Indonesian medicinal plants XVII. Characterization of Quassinoids from the stems of Quassia indica. Chem Pharm Bull 44: 2009-2014.

Kazuo K, Taichi O.1993. Indaquassin A and B: Quassinoids from Quassia indica. Phytochem 34: 505-509.

Kazuo K, Taichi O. 1994. Quassinoids from Quassia indica. Phytochem 35: 459- 463.

Martin AE, Montgomery PA.1996. Acarbose: an alpha-glucosidase inhibitor. Am J Health Syst Pharm 53: 2277-2290.

Prabha B, Neethu S, Lekshmy KS, Sherin DR, Madhukrishnan M, Ananthakrishnan R, Rameshkumar KB, Manojkumar TK, Jayamurthy P, Radhakrishnan KV. 2018. Antidiabetic potential of phytochemicals isolated from the stem bark of Myristica fatua Houtt. var. magnifica (Bedd.) Sinclair, Bioorg Med Chem 26: 3461-3467.

Prabha B, Sini S, Sherin DR, Neethu S, Rameshkumar KB, Manojkumar TK, Jayamurthy P, Radhakrishnan KV.2018. Promalabaricone B from Myristica fatua Houtt. var. magnifica (Bedd.) Sinclair seeds demonstrate antidiabetic potential by inhibiting carbohydrate hydrolyzing enzymes, protein glycation and modulating glucose uptake via the activation of AMPK in L6 myotubes. Nat Prod Res. https://doi.org/ 10.1080/14786419.2019.1607852).

Philip HC, Naidoo D, Mulholland DA, Randrianarivelojosia M. 2005. Quassinoids from the leaves of the Madagascan Simaroubaceae Samadera madagascariensisPhytochem 66: 2734-2739.

Ren L, Qin X, Cao X, Wang L, Bai F, Bai G, Shen Y.2011. Structural insight into substrate specificity of human intestinal maltaseglucoamylase. Prot Cell 2: 827-836.

Sasikumar P, Prabha B, Reshmitha TR, Sheeba V, Pradeep AK, Rohit KR, Dhanya BP, Sivan VV, Jithin MM, Anil KN, Shibi IG, Nisha P, Radhakrishnan KV. 2016. Comparison of antidiabetic potential of (+) and (-) Hopeaphenol, a pair of enantiomers isolated from Ampelocissus indica (L.) and Vateria indica Linn, with respect to inhibition of digestive enzymes and induction of glucose uptake in L6 myotubes. RSC Adv 6: 77075- 77082.

Sasikumar P, Sharathna P, Prabha B, Varughese S, Kumar NA, Sivan VV, Sherin DR, Suresh E, Manojkumar TK, Radhakrishnan KV.2018. Dihydro-ß,- agaro furan sesquiterpenoids from the seeds of Celastrus paniculatus Willd. and their α-glucosidase inhibitory activity. Phytochem Lett 26: 1-8.

Sasikumar P, Lekshmy KS, Sini S, Prabha B, Kumar NA, Sivan VV, Jithin MM, Jayamurthy P, ShibiI G, Radhakrishnan KV. 2019. Isolation and characterization of resveratrol oligomers from the stem bark of Hopea ponga (Dennst.) Mabb. and their antidiabetic effect by modulation of digestive enzymes, protein glycation and glucose uptake in L6 myocytes. J Ethnopharmacol 236: 196-204.

Sim L, Quezada CR, Sterchi EE, Nichols BL, Rose DR. 2008. Human intestinal maltaseglucoamylase: crystal structure of the N-terminal catalytic subunit and basis of inhibition and substrate specificity. J Mol Biol 375: 782-792.

Yamamoto K, Miyake H, Kusunoki M, Osaki S.2010. Crystal structures of isomaltase from Saccharomyces cerevisiae and in complex with its competitive inhibitor maltose. Febs J 277: 4205-4214.

Cite this article

Prabha B, Biji M, Madhukrishnan M, Sherin DR, Reshmitha TR, Sunil Varughese, Manojkumar TK, Nisha P, Radhakrishnan KV. 2021. Bioassay-guided isolation and characterization of potential α-glucosidase inhibitors from the seeds of Quassia indica Gaetrn. J Med Aromat Plant Sci 43: 25-36.

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