J. Pharm. Pharmacogn. Res., vol. 12, no. 3, pp. 453-476, May-Jun 2024.
DOI: https://doi.org/10.56499/jppres23.1816_12.3.453
Original Article
Two tetrahydroxyterpenoids and a flavonoid from Xylocarpus moluccensis M.Roem. and their α-glucosidase inhibitory and antioxidant capacity
[Dos tetrahidroxiterpenoides y un flavonoide de Xylocarpus moluccensis M.Roem. y su capacidad inhibidora y antioxidante de la α-glucosidasa]
Berna Elya1*, Fitri S. Budiarso1, Muhammad Hanafi2, Maria A. Gani3, Pekik W. Prasetyaningrum4
1Faculty of Pharmacy, University of Indonesia, Depok, Indonesia.
2Research Center for Pharmaceutical Ingredients and Traditional Medicine, National Research and Innovation Agency, Serpong, Indonesia.
3School of Pharmacy, Bandung Institute of Technology, Bandung, Indonesia.
4Research Center for Genetic Engineering, National Research and Innovation Agency, Cibinong, Indonesia.
*E-mail: berna.elya@farmasi.ui.ac.id
Abstract
Context: Scientific verification of the anti-hyperglycemic potential of Kayu sarampa (Xylocarpus moluccensis), which is popularly used for diabetic medication in North Sulawesi, Indonesia, is strongly important to conduct to avoid inappropriate medication that might cause worse conditions.
Aims: To investigate the anti-hyperglycemic potential of X. moluccensis stem bark ethyl acetate extract and isolated compounds through the α-glucosidase enzyme inhibitory and antioxidant capacity determination.
Methods: The active compound was isolated from ethyl acetate extract of X. moluccensis stem bark. The structures of those compounds were elucidated by infrared spectroscopy, liquid chromatography–mass spectrometry, and nuclear magnetic resonance spectroscopies. To discover the anti-hyperglycemic potency, α-glucosidase enzyme inhibition assay, antioxidant assay (DPPH and FRAP), and in silico study were performed.
Results: Three isolated compounds were obtained and characterized as two tetrahydroxyterpenoids compounds, namely xyloccensin E (1) and ruageanin D (2), and one flavonoid compound, namely 3,5,7,3ʹ,4ʹ-pentahidroxyflavan (catechin) (3). Compounds 1 and 3 inhibited the α-glucosidase enzyme with IC50 values of 118.60 and 55.19 µg/mL, respectively, with a competitive inhibition mechanism. This is also in line with in silico findings, and both compounds showed good binding affinity of α-glucosidase protein, which indicated their anti-hyperglycemic activity potential by inhibiting α-glucosidase enzyme. Moreover, compounds 1 and 3 showed antioxidant capacity through the DPPH method with an IC50 value of 54.69 and 2.87 µg/mL. In addition, 100 µg/mL of compounds 1 and 3 also exhibited antioxidant capacity through the FRAP method with values of 66.35 and 213.82 µmol Fe2+/g, respectively.
Conclusions: The X. moluccensis stem bark ethyl acetate extract, and isolated compounds exhibit α-glucosidase enzyme inhibitory activity and antioxidant capacity, which confirms its potency as an alternative medication for hyperglycemia issues.
Keywords: anti-hyperglycemia; α-glucosidase; antioxidant; natural products.
Resumen
Contexto: La verificación científica del potencial anti-hiperglucémico de Kayu sarampa (Xylocarpus moluccensis), que se utiliza popularmente para la medicación de los diabéticos en el norte de Sulawesi, Indonesia, es muy importante para evitar una medicación inadecuada que podría causar peores condiciones.
Objetivos: Investigar el potencial anti-hiperglucémico del extracto de acetato de etilo de la corteza del tallo de X. moluccensis y de los compuestos aislados mediante la determinación de la capacidad antioxidante e inhibidora de la enzima α-glucosidasa.
Métodos: Se aislaron los compuestos activos del extracto de acetato de etilo de la corteza del tallo de X. moluccensis. Las estructuras de esos compuestos se dilucidaron mediante espectroscopía infrarroja, cromatografía líquida-espectrometría de masas y espectroscopía de resonancia magnética nuclear. Para descubrir la potencia anti-hiperglucémica, fueron realizados un ensayo de inhibición de la enzima α-glucosidasa, un ensayo antioxidante (DPPH y FRAP) y un estudio in silico.
Resultados: Se obtuvieron y caracterizaron tres compuestos aislados: dos compuestos tetrahidroxiterpenoides, a saber, xiloccensina E (1) y ruageanina D (2), y un compuesto flavonoide, a saber, 3,5,7,3ʹ,4ʹ-pentahidroxiflavano (catequina) (3). Los compuestos 1 y 3 inhibieron la enzima α-glucosidasa con valores de IC50 de 118,60 y 55,19 µg/mL, respectivamente, con un mecanismo de inhibición competitiva. Esto también coincide con los hallazgos in silico, y ambos compuestos mostraron una buena afinidad de unión con la proteína α-glucosidasa, lo que indica su potencial actividad anti-hiperglucémica mediante la inhibición de la enzima α-glucosidasa. Además, los compuestos 1 y 3 mostraron capacidad antioxidante mediante el método DPPH con un valor IC50 de 54,69 y 2,87 µg/mL. Además, 100 µg/mL de los compuestos 1 y 3 también mostraron capacidad antioxidante mediante el método FRAP con valores de 66,35 y 213,82 µmol Fe2+/g, respectivamente.
Conclusiones: El extracto de acetato de etilo de corteza de tallo de X. moluccensis y los compuestos aislados exhiben actividad inhibidora de la enzima α-glucosidasa y capacidad antioxidante, lo que confirma su potencia como medicamento alternativo para problemas de hiperglucemia.
Palabras Clave: anti-hiperglucemia; antioxidante; α-glucosidasa; productos naturales.
Citation Format: Elya B, Budiarso FS, Hanafi M, Gani MA, Prasetyaningrum PW (2024) Two tetrahydroxyterpenoids and a flavonoid from Xylocarpus moluccensis M.Roem. and their α-glucosidase inhibitory and antioxidant capacity. J Pharm Pharmacogn Res 12(3): 453–476. https://doi.org/10.56499/jppres23.1816_12.3.453
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